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openbabel/scripts/python/examples/hashizume.cif
Geoffrey Hutchison 858f8a39f9 * Merged in changes from 2.1.x branch.
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##############################################################################
# #
# This CIF contains the data in a paper accepted for publication in Acta #
# Crystallographica Section B. It has been peer reviewed under the auspices #
# of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary may be obtained from #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1. #
# #
# Software is freely available for graphical display of the structure(s) in #
# this CIF. For information consult the CIF home page http://www.iucr.org/ #
# cif/home.html #
# #
# Copyright International Union of Crystallography #
# #
##############################################################################
data_global
_audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic 2002-11-14
_journal_date_accepted 2003-03-12
_journal_name_full 'Acta Crystallographica, Section B'
_journal_year 2003
_journal_volume 59
_journal_issue 3
_journal_page_first 404
_journal_page_last 415
_journal_paper_category FA
_publ_contact_author_name 'Dr. Daisuke Hashizume'
_publ_contact_author_address
;
Molecular Characterization Division
RIKEN (The Institute of Physical and Chemical Research
2-1, Hirosawa, Wako, Saitama 351-0198, Japan
;
_publ_contact_author_email 'hashi@postman.riken.go.jp'
_publ_contact_author_fax '81(48462)4628'
_publ_contact_author_phone '81(48467)9363'
_publ_section_title
;
Mechanism of First Order Phase Transition of Acylurea Derivative Crystal:
Observation of Intermediate Stages of Transformation
with a Detailed Temperature Resolved Single Crystal Diffraction Method
;
loop_
_publ_author_name
_publ_author_address
'Hashizume, Daisuke'
;
Department of Applied Physics and Chemistry
The University of Electro-Communications
Chofugaoka, Chofu, Tokyo 182-8585
Japan
;
'Miki, Naoko'
;
Department of Applied Physics and Chemistry
The University of Electro-Communications
Chofugaoka, Chofu, Tokyo 182-8585
Japan
;
'Yamazaki, Toshiyuki'
;
Department of Applied Physics and Chemistry
The University of Electro-Communications
Chofugaoka, Chofu, Tokyo 182-8585
Japan
;
'Aoyagi, Yosuke'
;
Department of Applied Physics and Chemistry
The University of Electro-Communications
Chofugaoka, Chofu, Tokyo 182-8585
Japan
;
'Tomokuni, Arisato'
;
Department of Chemistry
Aoyama Gakuin University
Chitosedai, Setagaya, Tokyo 157-8572
Japan
;
'Hiroki, Uchiyama'
;
Department of Chemistry
Aoyama Gakuin University
Chitosedai, Setagaya, Tokyo 157-8572
Japan
;
'Tadashi, Endo'
;
Department of Chemistry
Aoyama Gakuin University
Chitosedai, Setagaya, Tokyo 157-8572
Japan
;
'Yasui, Masanori'
;
Department of Applied Physics and Chemistry
The University of Electro-Communications
Chofugaoka, Chofu, Tokyo 182-8585
Japan
;
'Iwasaki, Fujiko'
;
Department of Applied Physics and Chemistry
The University of Electro-Communications
Chofugaoka, Chofu, Tokyo 182-8585
Japan
;
_publ_section_synopsis
; ?
;
data_ethyl98K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.7038(14)
_cell_length_b 12.204(3)
_cell_length_c 4.9747(10)
_cell_angle_alpha 93.021(11)
_cell_angle_beta 90.616(7)
_cell_angle_gamma 90.319(10)
_cell_volume 527.64(19)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 4199
_cell_measurement_theta_min 2.34
_cell_measurement_theta_max 27.485
_cell_measurement_temperature 98
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 0.80
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.172
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.083
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal is being low temperature phase.
;
_diffrn_ambient_temperature 98
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 6068
_diffrn_reflns_av_R_equivalents 0.035
_diffrn_reflns_av_sigmaI/netI 0.0133
_diffrn_reflns_theta_min 2.34
_diffrn_reflns_theta_max 27.48
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measured_fraction_theta_full 0.857
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 2076
_reflns_number_gt 1992
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0468
_refine_ls_R_factor_gt 0.0453
_refine_ls_wR_factor_gt 0.1263
_refine_ls_wR_factor_ref 0.1282
_refine_ls_goodness_of_fit_ref 1.101
_refine_ls_restrained_S_all 1.101
_refine_ls_number_reflns 2076
_refine_ls_number_parameters 190
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment refall
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0769P)^2^+0.1768P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.272
_refine_diff_density_min -0.236
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution 'SIR-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.44032(10) 0.57459(7) 0.24164(18) 0.0197(2) Uani d . 1 . . O
O2 0.02166(10) 0.40706(7) 0.22035(18) 0.0195(2) Uani d . 1 . . O
N1 0.19696(12) 0.53547(8) 0.3825(2) 0.0165(3) Uani d . 1 . . N
H11 0.128(2) 0.5538(14) 0.506(4) 0.021(4) Uiso d . 1 . . H
N2 0.25049(12) 0.41607(8) 0.0069(2) 0.0167(2) Uani d . 1 . . N
H21 0.338(2) 0.4465(14) 0.003(4) 0.023(4) Uiso d . 1 . . H
C1 0.33545(14) 0.59050(9) 0.4018(2) 0.0158(3) Uani d . 1 . . C
C2 0.15101(14) 0.44889(9) 0.1958(2) 0.0162(3) Uani d . 1 . . C
C11 0.35090(15) 0.67433(10) 0.6398(2) 0.0178(3) Uani d . 1 . . C
H111 0.439(2) 0.6487(13) 0.745(3) 0.021(4) Uiso d . 1 . . H
H112 0.2602(19) 0.6735(13) 0.748(3) 0.018(4) Uiso d . 1 . . H
C12 0.38521(15) 0.79070(10) 0.5489(3) 0.0198(3) Uani d . 1 . . C
H121 0.405(2) 0.8406(15) 0.712(4) 0.027(4) Uiso d . 1 . . H
H122 0.4770(19) 0.7875(13) 0.445(3) 0.018(4) Uiso d . 1 . . H
C13 0.25484(18) 0.84117(10) 0.3886(3) 0.0260(3) Uani d . 1 . . C
H131 0.232(2) 0.7902(16) 0.225(4) 0.033(5) Uiso d . 1 . . H
C14 0.3084(3) 0.95237(12) 0.2891(3) 0.0387(4) Uani d . 1 . . C
H141 0.332(2) 1.0040(17) 0.440(4) 0.040(5) Uiso d . 1 . . H
H142 0.397(3) 0.9434(18) 0.175(5) 0.047(6) Uiso d . 1 . . H
H143 0.224(3) 0.9838(19) 0.185(5) 0.053(6) Uiso d . 1 . . H
C15 0.10882(18) 0.85613(13) 0.5535(4) 0.0354(4) Uani d . 1 . . C
H151 0.131(2) 0.9070(17) 0.722(4) 0.041(5) Uiso d . 1 . . H
H152 0.065(3) 0.7830(19) 0.622(5) 0.050(6) Uiso d . 1 . . H
H153 0.026(3) 0.8914(19) 0.445(5) 0.052(6) Uiso d . 1 . . H
C21 0.21377(14) 0.32246(10) -0.1823(2) 0.0181(3) Uani d . 1 . . C
H211 0.2767(18) 0.3308(13) -0.340(3) 0.017(4) Uiso d . 1 . . H
H212 0.107(2) 0.3260(13) -0.231(3) 0.019(4) Uiso d . 1 . . H
C22 0.24513(17) 0.21233(11) -0.0605(3) 0.0252(3) Uani d . 1 . . C
H221 0.355(2) 0.2097(16) -0.005(4) 0.039(5) Uiso d . 1 . . H
H222 0.179(2) 0.2045(15) 0.100(4) 0.033(5) Uiso d . 1 . . H
H223 0.221(2) 0.1502(16) -0.196(4) 0.037(5) Uiso d . 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0159(4) 0.0238(5) 0.0191(4) -0.0018(3) 0.0033(4) -0.0007(3)
O2 0.0150(4) 0.0237(5) 0.0195(4) -0.0031(3) 0.0032(3) -0.0011(3)
N1 0.0139(5) 0.0198(5) 0.0155(5) -0.0004(4) 0.0037(4) -0.0015(4)
N2 0.0136(5) 0.0197(5) 0.0164(5) -0.0017(4) 0.0012(4) -0.0018(4)
C1 0.0158(6) 0.0165(5) 0.0154(6) 0.0006(4) -0.0010(5) 0.0030(4)
C2 0.0165(6) 0.0171(5) 0.0151(5) 0.0006(4) -0.0008(4) 0.0024(4)
C11 0.0169(6) 0.0210(6) 0.0153(6) -0.0003(4) 0.0001(5) -0.0010(4)
C12 0.0192(6) 0.0196(6) 0.0204(6) -0.0026(4) 0.0016(5) -0.0018(4)
C13 0.0374(8) 0.0186(6) 0.0215(6) 0.0000(5) -0.0086(6) -0.0014(5)
C14 0.0656(12) 0.0217(7) 0.0289(8) -0.0009(7) -0.0022(8) 0.0029(6)
C15 0.0244(7) 0.0270(7) 0.0544(10) 0.0034(5) -0.0106(7) -0.0002(7)
C21 0.0170(6) 0.0214(6) 0.0156(6) -0.0004(4) -0.0001(5) -0.0030(4)
C22 0.0274(7) 0.0213(6) 0.0267(7) 0.0014(5) 0.0014(6) -0.0010(5)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.2275(15) ?
O2 C2 . 1.2435(15) ?
N1 C1 . 1.3766(15) ?
N1 C2 . 1.4224(15) ?
N1 H11 . 0.880(19) ?
N2 C2 . 1.3321(16) ?
N2 C21 . 1.4730(15) ?
N2 H21 . 0.846(18) ?
C1 C11 . 1.5280(16) ?
C11 C12 . 1.5417(17) ?
C11 H111 . 0.984(18) ?
C11 H112 . 0.961(17) ?
C12 C13 . 1.5304(19) ?
C12 H121 . 1.003(18) ?
C12 H122 . 0.955(17) ?
C13 C15 . 1.527(2) ?
C13 C14 . 1.540(2) ?
C13 H131 . 1.01(2) ?
C14 H141 . 0.98(2) ?
C14 H142 . 0.97(2) ?
C14 H143 . 0.99(2) ?
C15 H151 . 1.03(2) ?
C15 H152 . 1.04(2) ?
C15 H153 . 1.01(3) ?
C21 C22 . 1.5280(18) ?
C21 H211 . 0.971(16) ?
C21 H212 . 0.959(17) ?
C22 H221 . 0.99(2) ?
C22 H222 . 0.997(19) ?
C22 H223 . 1.01(2) ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 128.59(10) ?
C1 N1 H11 . . 116.4(11) ?
C2 N1 H11 . . 114.9(11) ?
C2 N2 C21 . . 120.62(11) ?
C2 N2 H21 . . 119.6(12) ?
C21 N2 H21 . . 119.6(12) ?
O1 C1 N1 . . 123.40(11) ?
O1 C1 C11 . . 121.49(11) ?
N1 C1 C11 . . 115.11(10) ?
O2 C2 N2 . . 123.75(11) ?
O2 C2 N1 . . 118.33(11) ?
N2 C2 N1 . . 117.90(11) ?
C1 C11 C12 . . 112.12(10) ?
C1 C11 H111 . . 104.6(10) ?
C12 C11 H111 . . 109.3(9) ?
C1 C11 H112 . . 110.2(10) ?
C12 C11 H112 . . 111.1(10) ?
H111 C11 H112 . . 109.3(14) ?
C13 C12 C11 . . 114.44(11) ?
C13 C12 H121 . . 107.3(10) ?
C11 C12 H121 . . 108.8(10) ?
C13 C12 H122 . . 110.3(10) ?
C11 C12 H122 . . 107.9(9) ?
H121 C12 H122 . . 107.8(14) ?
C15 C13 C12 . . 112.30(12) ?
C15 C13 C14 . . 110.07(13) ?
C12 C13 C14 . . 109.30(13) ?
C15 C13 H131 . . 109.2(11) ?
C12 C13 H131 . . 107.8(11) ?
C14 C13 H131 . . 108.1(11) ?
C13 C14 H141 . . 110.9(12) ?
C13 C14 H142 . . 110.9(13) ?
H141 C14 H142 . . 109.8(18) ?
C13 C14 H143 . . 108.6(13) ?
H141 C14 H143 . . 107.5(18) ?
H142 C14 H143 . . 109.1(19) ?
C13 C15 H151 . . 109.7(11) ?
C13 C15 H152 . . 113.7(13) ?
H151 C15 H152 . . 106.7(17) ?
C13 C15 H153 . . 110.8(13) ?
H151 C15 H153 . . 107.7(18) ?
H152 C15 H153 . . 108.0(18) ?
N2 C21 C22 . . 112.23(10) ?
N2 C21 H211 . . 106.7(9) ?
C22 C21 H211 . . 110.5(9) ?
N2 C21 H212 . . 108.5(10) ?
C22 C21 H212 . . 109.0(10) ?
H211 C21 H212 . . 109.9(14) ?
C21 C22 H221 . . 108.9(12) ?
C21 C22 H222 . . 109.5(11) ?
H221 C22 H222 . . 109.7(17) ?
C21 C22 H223 . . 110.3(12) ?
H221 C22 H223 . . 109.7(17) ?
H222 C22 H223 . . 108.7(15) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 4.1(2) ?
C2 N1 C1 C11 . . . . -175.84(11) ?
C21 N2 C2 O2 . . . . -2.54(18) ?
C21 N2 C2 N1 . . . . 176.29(10) ?
C1 N1 C2 O2 . . . . 177.05(11) ?
C1 N1 C2 N2 . . . . -1.85(19) ?
O1 C1 C11 C12 . . . . 58.34(15) ?
N1 C1 C11 C12 . . . . -121.68(12) ?
C1 C11 C12 C13 . . . . 65.93(14) ?
C11 C12 C13 C15 . . . . 62.45(15) ?
C11 C12 C13 C14 . . . . -175.11(12) ?
C2 N2 C21 C22 . . . . -81.62(14) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.846(18) 2.300(18) 2.9778(15) 137.4(16)
N1 H11 O2 2_566 0.880(19) 1.942(19) 2.8222(14) 179.3(17)
data_ethyl298K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.8173(5)
_cell_length_b 12.4339(12)
_cell_length_c 5.09630(10)
_cell_angle_alpha 92.912(12)
_cell_angle_beta 89.876(3)
_cell_angle_gamma 90.152(10)
_cell_volume 558.00(6)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 3690
_cell_measurement_theta_min 2.31
_cell_measurement_theta_max 27.485
_cell_measurement_temperature 298
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 0.80
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.109
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.078
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being low temperature phase.
;
_diffrn_ambient_temperature 298
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 6494
_diffrn_reflns_av_R_equivalents 0.026
_diffrn_reflns_av_sigmaI/netI 0.0128
_diffrn_reflns_theta_min 2.31
_diffrn_reflns_theta_max 27.48
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measured_fraction_theta_full 0.890
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 2292
_reflns_number_gt 2041
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0623
_refine_ls_R_factor_gt 0.0572
_refine_ls_wR_factor_gt 0.1642
_refine_ls_wR_factor_ref 0.1709
_refine_ls_goodness_of_fit_ref 1.090
_refine_ls_restrained_S_all 1.090
_refine_ls_number_reflns 2292
_refine_ls_number_parameters 118
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0925P)^2^+0.1104P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.161
_refine_diff_density_min -0.205
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 98K was used as an initial model.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.43498(13) 0.57527(10) 0.2374(2) 0.0566(3) Uani d . 1 . . O
O2 0.02574(12) 0.40870(10) 0.2301(2) 0.0559(3) Uani d . 1 . . O
N1 0.19711(14) 0.53487(11) 0.3806(3) 0.0458(3) Uani d . 1 . . N
H11 0.1303 0.5546 0.4964 0.055 Uiso calc R 1 . . H
N2 0.25183(14) 0.41611(11) 0.0194(3) 0.0467(3) Uani d . 1 . . N
H21 0.3377 0.4486 0.0081 0.056 Uiso calc R 1 . . H
C1 0.33136(17) 0.59074(12) 0.3945(3) 0.0434(3) Uani d . 1 . . C
C2 0.15267(17) 0.44949(12) 0.2036(3) 0.0435(3) Uani d . 1 . . C
C11 0.34433(19) 0.67384(13) 0.6232(3) 0.0506(4) Uani d . 1 . . C
H111 0.4235 0.6518 0.7407 0.061 Uiso calc R 1 . . H
H112 0.2497 0.6756 0.7206 0.061 Uiso calc R 1 . . H
C12 0.3802(2) 0.78742(14) 0.5365(4) 0.0593(5) Uani d . 1 . . C
H122 0.4721 0.7845 0.4314 0.071 Uiso calc R 1 . . H
H121 0.4003 0.8337 0.6917 0.071 Uiso calc R 1 . . H
C13 0.2540(3) 0.83858(16) 0.3773(4) 0.0796(7) Uani d . 1 . . C
H131 0.2317 0.7905 0.2237 0.096 Uiso calc R 1 . . H
C14 0.3089(5) 0.9478(2) 0.2795(6) 0.1270(14) Uani d . 1 . . C
H142 0.4010 0.9374 0.1807 0.152 Uiso calc R 1 . . H
H141 0.3273 0.9970 0.4276 0.152 Uiso calc R 1 . . H
H143 0.2326 0.9770 0.1696 0.152 Uiso calc R 1 . . H
C15 0.1085(3) 0.8545(2) 0.5371(8) 0.1137(11) Uani d . 1 . . C
H152 0.0752 0.7865 0.5975 0.136 Uiso calc R 1 . . H
H153 0.0313 0.8837 0.4289 0.136 Uiso calc R 1 . . H
H151 0.1275 0.9034 0.6853 0.136 Uiso calc R 1 . . H
C21 0.21680(19) 0.32495(14) -0.1641(3) 0.0521(4) Uani d . 1 . . C
H211 0.2769 0.3309 -0.3224 0.062 Uiso calc R 1 . . H
H212 0.1107 0.3281 -0.2130 0.062 Uiso calc R 1 . . H
C22 0.2482(3) 0.21723(17) -0.0493(5) 0.0752(6) Uani d . 1 . . C
H223 0.2233 0.1603 -0.1764 0.090 Uiso calc R 1 . . H
H222 0.1875 0.2102 0.1056 0.090 Uiso calc R 1 . . H
H221 0.3536 0.2129 -0.0045 0.090 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0431(6) 0.0655(7) 0.0603(7) -0.0078(5) 0.0161(5) -0.0055(5)
O2 0.0417(6) 0.0639(7) 0.0611(7) -0.0104(5) 0.0151(5) -0.0057(5)
N1 0.0388(6) 0.0504(7) 0.0478(7) -0.0021(5) 0.0119(5) -0.0017(5)
N2 0.0373(6) 0.0524(7) 0.0500(7) -0.0035(5) 0.0094(5) -0.0028(5)
C1 0.0393(7) 0.0459(7) 0.0454(7) 0.0009(6) 0.0040(6) 0.0075(6)
C2 0.0375(7) 0.0473(8) 0.0459(8) 0.0003(5) 0.0075(6) 0.0044(6)
C11 0.0484(8) 0.0565(9) 0.0464(8) -0.0022(7) 0.0016(7) -0.0007(7)
C12 0.0574(10) 0.0546(9) 0.0648(10) -0.0081(7) 0.0072(8) -0.0070(8)
C13 0.1154(19) 0.0504(10) 0.0725(13) 0.0025(11) -0.0222(13) -0.0023(9)
C14 0.222(4) 0.0612(14) 0.099(2) 0.0031(19) 0.000(2) 0.0182(14)
C15 0.0764(17) 0.0853(18) 0.179(3) 0.0166(13) -0.027(2) 0.0036(19)
C21 0.0456(8) 0.0586(9) 0.0512(9) 0.0001(7) 0.0038(7) -0.0056(7)
C22 0.0866(15) 0.0569(11) 0.0815(14) 0.0030(10) 0.0070(12) -0.0040(9)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.2227(19) ?
O2 C2 . 1.2375(18) ?
N1 C1 . 1.3710(19) ?
N1 C2 . 1.413(2) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.3328(19) ?
N2 C21 . 1.465(2) ?
N2 H21 . 0.8600 ?
C1 C11 . 1.522(2) ?
C11 C12 . 1.533(2) ?
C11 H111 . 0.9700 ?
C11 H112 . 0.9700 ?
C12 C13 . 1.537(3) ?
C12 H122 . 0.9700 ?
C12 H121 . 0.9700 ?
C13 C15 . 1.526(4) ?
C13 C14 . 1.547(3) ?
C13 H131 . 0.9800 ?
C14 H142 . 0.9600 ?
C14 H141 . 0.9600 ?
C14 H143 . 0.9600 ?
C15 H152 . 0.9600 ?
C15 H153 . 0.9600 ?
C15 H151 . 0.9600 ?
C21 C22 . 1.515(3) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 H223 . 0.9600 ?
C22 H222 . 0.9600 ?
C22 H221 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 129.32(13) ?
C1 N1 H11 . . 115.3 ?
C2 N1 H11 . . 115.3 ?
C2 N2 C21 . . 121.00(13) ?
C2 N2 H21 . . 119.5 ?
C21 N2 H21 . . 119.5 ?
O1 C1 N1 . . 123.17(15) ?
O1 C1 C11 . . 121.57(14) ?
N1 C1 C11 . . 115.25(13) ?
O2 C2 N2 . . 123.65(15) ?
O2 C2 N1 . . 118.60(13) ?
N2 C2 N1 . . 117.74(13) ?
C1 C11 C12 . . 113.22(13) ?
C1 C11 H111 . . 108.9 ?
C12 C11 H111 . . 108.9 ?
C1 C11 H112 . . 108.9 ?
C12 C11 H112 . . 108.9 ?
H111 C11 H112 . . 107.7 ?
C11 C12 C13 . . 114.62(16) ?
C11 C12 H122 . . 108.6 ?
C13 C12 H122 . . 108.6 ?
C11 C12 H121 . . 108.6 ?
C13 C12 H121 . . 108.6 ?
H122 C12 H121 . . 107.6 ?
C15 C13 C12 . . 112.0(2) ?
C15 C13 C14 . . 109.9(2) ?
C12 C13 C14 . . 109.8(2) ?
C15 C13 H131 . . 108.4 ?
C12 C13 H131 . . 108.4 ?
C14 C13 H131 . . 108.4 ?
C13 C14 H142 . . 109.5 ?
C13 C14 H141 . . 109.5 ?
H142 C14 H141 . . 109.5 ?
C13 C14 H143 . . 109.5 ?
H142 C14 H143 . . 109.5 ?
H141 C14 H143 . . 109.5 ?
C13 C15 H152 . . 109.5 ?
C13 C15 H153 . . 109.5 ?
H152 C15 H153 . . 109.5 ?
C13 C15 H151 . . 109.5 ?
H152 C15 H151 . . 109.5 ?
H153 C15 H151 . . 109.5 ?
N2 C21 C22 . . 112.64(15) ?
N2 C21 H211 . . 109.1 ?
C22 C21 H211 . . 109.1 ?
N2 C21 H212 . . 109.1 ?
C22 C21 H212 . . 109.1 ?
H211 C21 H212 . . 107.8 ?
C21 C22 H223 . . 109.5 ?
C21 C22 H222 . . 109.5 ?
H223 C22 H222 . . 109.5 ?
C21 C22 H221 . . 109.5 ?
H223 C22 H221 . . 109.5 ?
H222 C22 H221 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 3.1(3) ?
C2 N1 C1 C11 . . . . -176.24(14) ?
C21 N2 C2 O2 . . . . -1.4(2) ?
C21 N2 C2 N1 . . . . 177.30(13) ?
C1 N1 C2 O2 . . . . 178.47(14) ?
C1 N1 C2 N2 . . . . -0.3(2) ?
O1 C1 C11 C12 . . . . 56.7(2) ?
N1 C1 C11 C12 . . . . -123.93(15) ?
C1 C11 C12 C13 . . . . 66.0(2) ?
C11 C12 C13 C15 . . . . 62.9(2) ?
C11 C12 C13 C14 . . . . -174.74(19) ?
C2 N2 C21 C22 . . . . -82.8(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.86 2.37 3.0573(17) 136.9
N1 H11 O2 2_566 0.86 1.99 2.8525(17) 176.6
data_ethyl328K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.7817(18)
_cell_length_b 12.381(2)
_cell_length_c 5.1113(11)
_cell_angle_alpha 92.491(8)
_cell_angle_beta 90.164(9)
_cell_angle_gamma 89.589(9)
_cell_volume 555.17(19)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 3475
_cell_measurement_theta_min 2.31
_cell_measurement_theta_max 27.47
_cell_measurement_temperature 328
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 0.80
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.114
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.079
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being low temperature phase.
;
_diffrn_ambient_temperature 328
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 7578
_diffrn_reflns_av_R_equivalents 0.026
_diffrn_reflns_av_sigmaI/netI 0.0148
_diffrn_reflns_theta_min 2.32
_diffrn_reflns_theta_max 27.48
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measured_fraction_theta_full 0.849
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 2169
_reflns_number_gt 1728
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0738
_refine_ls_R_factor_gt 0.0599
_refine_ls_wR_factor_gt 0.1475
_refine_ls_wR_factor_ref 0.1621
_refine_ls_goodness_of_fit_ref 1.077
_refine_ls_restrained_S_all 1.077
_refine_ls_number_reflns 2169
_refine_ls_number_parameters 166
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+0.1725P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.174
_refine_diff_density_min -0.177
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 298K was used as an initial model.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.43409(16) 0.57524(13) 0.2348(3) 0.0691(5) Uani d . 1 . . O
O2 0.02639(15) 0.40900(13) 0.2335(3) 0.0688(5) Uani d . 1 . . O
N1 0.19755(18) 0.53428(14) 0.3789(4) 0.0565(4) Uani d . 1 . . N
H11 0.134(3) 0.5526(18) 0.491(5) 0.063(6) Uiso d . 1 . . H
N2 0.25155(19) 0.41618(14) 0.0232(3) 0.0589(5) Uani d . 1 . . N
H21 0.331(3) 0.4469(19) 0.017(5) 0.070(7) Uiso d . 1 . . H
C1 0.3307(2) 0.59059(15) 0.3924(4) 0.0537(5) Uani d . 1 . . C
C2 0.1534(2) 0.44946(16) 0.2065(4) 0.0543(5) Uani d . 1 . . C
C11 0.3432(3) 0.67318(18) 0.6154(5) 0.0641(5) Uani d . 1 . . C
H112 0.252(3) 0.676(2) 0.715(5) 0.081(7) Uiso d . 1 . . H
H111 0.427(3) 0.650(2) 0.729(6) 0.097(9) Uiso d . 1 . . H
C12 0.3788(3) 0.7864(2) 0.5310(6) 0.0760(7) Uani d . 1 . . C
H121 0.400(3) 0.842(2) 0.704(6) 0.101(9) Uiso d . 1 . . H
H122 0.480(4) 0.782(2) 0.415(6) 0.103(9) Uiso d . 1 . . H
C13 0.2550(4) 0.8377(2) 0.3726(7) 0.0996(10) Uani d . 1 . . C
H131 0.234(4) 0.790(3) 0.224(8) 0.131(12) Uiso d . 1 . . H
C14 0.3084(7) 0.9468(3) 0.2766(9) 0.1566(19) Uani d . 1 . . C
H143 0.2285 0.9790 0.1770 0.188 Uiso calc R 1 . . H
H142 0.3968 0.9359 0.1683 0.188 Uiso calc R 1 . . H
H141 0.3333 0.9939 0.4245 0.188 Uiso calc R 1 . . H
C15 0.1083(4) 0.8540(3) 0.5295(11) 0.1496(18) Uani d . 1 . . C
H153 0.0324 0.8869 0.4228 0.179 Uiso calc R 1 . . H
H151 0.1279 0.9000 0.6817 0.179 Uiso calc R 1 . . H
H152 0.0725 0.7852 0.5827 0.179 Uiso calc R 1 . . H
C21 0.2176(3) 0.32596(19) -0.1566(5) 0.0652(6) Uani d . 1 . . C
H212 0.111(3) 0.3305(18) -0.210(5) 0.069(6) Uiso d . 1 . . H
H211 0.279(3) 0.3354(19) -0.316(5) 0.078(7) Uiso d . 1 . . H
C22 0.2497(5) 0.2186(2) -0.0422(8) 0.0929(9) Uani d . 1 . . C
H223 0.229(4) 0.161(3) -0.165(7) 0.110(10) Uiso d . 1 . . H
H222 0.188(4) 0.209(2) 0.100(7) 0.104(10) Uiso d . 1 . . H
H221 0.363(4) 0.214(3) 0.001(6) 0.114(11) Uiso d . 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0488(7) 0.0798(10) 0.0782(10) -0.0104(6) 0.0217(7) -0.0042(8)
O2 0.0478(8) 0.0781(10) 0.0802(10) -0.0124(7) 0.0188(7) -0.0034(8)
N1 0.0449(8) 0.0618(10) 0.0630(10) -0.0027(7) 0.0163(7) 0.0010(8)
N2 0.0429(8) 0.0654(10) 0.0683(11) -0.0045(7) 0.0120(7) 0.0013(8)
C1 0.0434(9) 0.0560(10) 0.0625(11) 0.0012(7) 0.0067(8) 0.0122(9)
C2 0.0422(9) 0.0583(11) 0.0631(11) 0.0002(7) 0.0106(8) 0.0099(9)
C11 0.0565(12) 0.0684(13) 0.0673(13) -0.0027(10) 0.0054(10) 0.0014(10)
C12 0.0675(14) 0.0705(14) 0.0896(17) -0.0082(11) 0.0109(12) -0.0023(13)
C13 0.133(3) 0.0673(16) 0.098(2) 0.0028(16) -0.0226(19) 0.0039(15)
C14 0.258(6) 0.080(2) 0.135(3) 0.004(3) 0.005(4) 0.030(2)
C15 0.089(2) 0.113(3) 0.247(6) 0.024(2) -0.025(3) 0.011(3)
C21 0.0526(11) 0.0728(14) 0.0698(14) -0.0016(9) 0.0059(10) -0.0026(11)
C22 0.102(2) 0.0703(17) 0.106(2) 0.0013(15) 0.0101(19) -0.0013(16)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.224(2) ?
O2 C2 . 1.236(2) ?
N1 C1 . 1.366(2) ?
N1 C2 . 1.398(3) ?
N1 H11 . 0.82(3) ?
N2 C2 . 1.325(2) ?
N2 C21 . 1.448(3) ?
N2 H21 . 0.80(2) ?
C1 C11 . 1.502(3) ?
C11 C12 . 1.519(3) ?
C11 H112 . 0.95(3) ?
C11 H111 . 0.98(3) ?
C12 C13 . 1.507(4) ?
C12 H121 . 1.12(3) ?
C12 H122 . 1.07(3) ?
C13 C15 . 1.527(5) ?
C13 C14 . 1.534(5) ?
C13 H131 . 0.96(4) ?
C14 H143 . 0.9600 ?
C14 H142 . 0.9600 ?
C14 H141 . 0.9600 ?
C15 H153 . 0.9600 ?
C15 H151 . 0.9600 ?
C15 H152 . 0.9600 ?
C21 C22 . 1.500(4) ?
C21 H212 . 0.98(2) ?
C21 H211 . 0.99(3) ?
C22 H223 . 0.95(3) ?
C22 H222 . 0.92(3) ?
C22 H221 . 1.02(4) ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 129.89(17) ?
C1 N1 H11 . . 115.1(16) ?
C2 N1 H11 . . 115.0(16) ?
C2 N2 C21 . . 121.34(18) ?
C2 N2 H21 . . 117.7(18) ?
C21 N2 H21 . . 120.9(18) ?
O1 C1 N1 . . 122.75(19) ?
O1 C1 C11 . . 121.63(18) ?
N1 C1 C11 . . 115.62(17) ?
O2 C2 N2 . . 123.54(19) ?
O2 C2 N1 . . 118.75(17) ?
N2 C2 N1 . . 117.71(17) ?
C1 C11 C12 . . 114.0(2) ?
C1 C11 H112 . . 110.6(15) ?
C12 C11 H112 . . 108.5(16) ?
C1 C11 H111 . . 107.6(17) ?
C12 C11 H111 . . 107.6(16) ?
H112 C11 H111 . . 108(2) ?
C13 C12 C11 . . 114.6(2) ?
C13 C12 H121 . . 106.5(15) ?
C11 C12 H121 . . 111.0(15) ?
C13 C12 H122 . . 108.0(16) ?
C11 C12 H122 . . 108.2(16) ?
H121 C12 H122 . . 108(2) ?
C12 C13 C15 . . 111.8(3) ?
C12 C13 C14 . . 110.2(3) ?
C15 C13 C14 . . 109.5(3) ?
C12 C13 H131 . . 108(2) ?
C15 C13 H131 . . 108(2) ?
C14 C13 H131 . . 109(2) ?
C13 C14 H143 . . 109.5 ?
C13 C14 H142 . . 109.5 ?
H143 C14 H142 . . 109.5 ?
C13 C14 H141 . . 109.5 ?
H143 C14 H141 . . 109.5 ?
H142 C14 H141 . . 109.5 ?
C13 C15 H153 . . 109.5 ?
C13 C15 H151 . . 109.5 ?
H153 C15 H151 . . 109.5 ?
C13 C15 H152 . . 109.5 ?
H153 C15 H152 . . 109.5 ?
H151 C15 H152 . . 109.5 ?
N2 C21 C22 . . 112.8(2) ?
N2 C21 H212 . . 109.0(13) ?
C22 C21 H212 . . 110.1(13) ?
N2 C21 H211 . . 107.1(14) ?
C22 C21 H211 . . 111.2(14) ?
H212 C21 H211 . . 106(2) ?
C21 C22 H223 . . 111(2) ?
C21 C22 H222 . . 110(2) ?
H223 C22 H222 . . 107(3) ?
C21 C22 H221 . . 108.9(18) ?
H223 C22 H221 . . 106(3) ?
H222 C22 H221 . . 113(3) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 3.4(3) ?
C2 N1 C1 C11 . . . . -176.41(19) ?
C21 N2 C2 O2 . . . . -2.0(3) ?
C21 N2 C2 N1 . . . . 177.44(18) ?
C1 N1 C2 O2 . . . . 178.90(19) ?
C1 N1 C2 N2 . . . . -0.5(3) ?
O1 C1 C11 C12 . . . . 55.6(3) ?
N1 C1 C11 C12 . . . . -124.7(2) ?
C1 C11 C12 C13 . . . . 65.7(3) ?
C11 C12 C13 C15 . . . . 63.1(4) ?
C11 C12 C13 C14 . . . . -174.8(3) ?
C2 N2 C21 C22 . . . . -82.2(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.80(2) 2.44(3) 3.067(2) 136(2)
N1 H11 O2 2_566 0.82(3) 2.04(3) 2.858(2) 177(2)
data_ethyl348K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.740(2)
_cell_length_b 12.357(2)
_cell_length_c 5.1473(12)
_cell_angle_alpha 91.509(8)
_cell_angle_beta 90.236(11)
_cell_angle_gamma 89.525(13)
_cell_volume 555.7(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2704
_cell_measurement_theta_min 1.65
_cell_measurement_theta_max 26.93
_cell_measurement_temperature 348
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 0.80
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.113
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.079
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being low temperature phase.
;
_diffrn_ambient_temperature 348
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 6205
_diffrn_reflns_av_R_equivalents 0.036
_diffrn_reflns_av_sigmaI/netI 0.0177
_diffrn_reflns_theta_min 2.33
_diffrn_reflns_theta_max 27.46
_diffrn_reflns_theta_full 27.46
_diffrn_measured_fraction_theta_max 0.760
_diffrn_measured_fraction_theta_full 0.760
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 1939
_reflns_number_gt 1418
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1003
_refine_ls_R_factor_gt 0.0816
_refine_ls_wR_factor_gt 0.2314
_refine_ls_wR_factor_ref 0.2549
_refine_ls_goodness_of_fit_ref 1.059
_refine_ls_restrained_S_all 1.065
_refine_ls_number_reflns 1939
_refine_ls_number_parameters 118
_refine_ls_number_restraints 5
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1229P)^2^+0.2315P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.269
_refine_diff_density_min -0.211
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 328K was used as an initial model.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.4329(2) 0.5747(2) 0.2314(5) 0.0846(7) Uani d . 1 . . O
O2 0.0266(2) 0.4099(2) 0.2382(5) 0.0837(7) Uani d . 1 . . O
N1 0.1972(3) 0.5337(2) 0.3770(5) 0.0701(7) Uani d . 1 . . N
H11 0.1302 0.5530 0.4913 0.084 Uiso calc R 1 . . H
N2 0.2522(3) 0.4162(2) 0.0286(5) 0.0732(7) Uani d . 1 . . N
H21 0.3388 0.4483 0.0170 0.088 Uiso calc R 1 . . H
C1 0.3299(3) 0.5903(2) 0.3881(6) 0.0684(8) Uani d . 1 . . C
C2 0.1534(3) 0.4499(3) 0.2098(6) 0.0689(8) Uani d . 1 . . C
C11 0.3418(4) 0.6722(3) 0.6063(7) 0.0805(9) Uani d D 1 . . C
H112 0.4210 0.6488 0.7254 0.097 Uiso calc R 1 . . H
H111 0.2459 0.6740 0.7005 0.097 Uiso calc R 1 . . H
C12 0.3776(5) 0.7849(3) 0.5237(9) 0.1003(12) Uani d D 1 . . C
H122 0.4711 0.7827 0.4229 0.120 Uiso calc R 1 . . H
H121 0.3961 0.8299 0.6777 0.120 Uiso calc R 1 . . H
C13 0.2532(6) 0.8367(4) 0.3649(10) 0.1236(17) Uani d D 1 . . C
H131 0.2302 0.7897 0.2137 0.148 Uiso calc R 1 . . H
C14 0.3071(11) 0.9462(5) 0.2717(15) 0.196(4) Uani d D 1 . . C
H143 0.2280 0.9787 0.1692 0.235 Uiso calc R 1 . . H
H142 0.3975 0.9361 0.1682 0.235 Uiso calc R 1 . . H
H141 0.3298 0.9926 0.4192 0.235 Uiso calc R 1 . . H
C15 0.1075(6) 0.8540(5) 0.5253(17) 0.185(3) Uani d D 1 . . C
H152 0.0729 0.7856 0.5861 0.222 Uiso calc R 1 . . H
H153 0.0294 0.8857 0.4191 0.222 Uiso calc R 1 . . H
H151 0.1287 0.9015 0.6714 0.222 Uiso calc R 1 . . H
C21 0.2180(4) 0.3277(3) -0.1486(7) 0.0808(9) Uani d D 1 . . C
H211 0.2786 0.3345 -0.3046 0.097 Uiso calc R 1 . . H
H212 0.1109 0.3317 -0.1981 0.097 Uiso calc R 1 . . H
C22 0.2497(6) 0.2198(3) -0.0343(10) 0.1109(14) Uani d D 1 . . C
H223 0.2247 0.1635 -0.1591 0.133 Uiso calc R 1 . . H
H222 0.1887 0.2120 0.1187 0.133 Uiso calc R 1 . . H
H221 0.3561 0.2145 0.0110 0.133 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0539(12) 0.0981(16) 0.1021(16) -0.0133(10) 0.0244(11) -0.0008(13)
O2 0.0553(13) 0.0932(15) 0.1029(17) -0.0144(10) 0.0238(11) -0.0022(13)
N1 0.0513(13) 0.0771(15) 0.0822(16) -0.0061(11) 0.0199(11) 0.0039(13)
N2 0.0508(13) 0.0810(16) 0.0878(17) -0.0061(11) 0.0168(12) 0.0008(14)
C1 0.0514(15) 0.0752(17) 0.0796(19) -0.0018(12) 0.0091(13) 0.0186(15)
C2 0.0480(15) 0.0787(18) 0.0809(19) -0.0023(12) 0.0141(13) 0.0139(15)
C11 0.0653(19) 0.084(2) 0.092(2) -0.0069(15) 0.0076(16) 0.0038(18)
C12 0.085(3) 0.095(3) 0.121(3) -0.013(2) 0.016(2) -0.004(2)
C13 0.157(5) 0.094(3) 0.120(4) 0.001(3) -0.020(3) 0.011(3)
C14 0.299(11) 0.105(4) 0.186(7) -0.006(5) 0.006(7) 0.048(4)
C15 0.102(4) 0.143(5) 0.312(10) 0.027(3) -0.020(5) 0.028(6)
C21 0.0619(19) 0.092(2) 0.089(2) -0.0042(15) 0.0082(16) 0.0021(18)
C22 0.115(3) 0.086(3) 0.131(4) 0.001(2) 0.007(3) 0.004(2)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.222(4) ?
O2 C2 . 1.228(3) ?
N1 C1 . 1.359(4) ?
N1 C2 . 1.385(4) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.330(4) ?
N2 C21 . 1.439(4) ?
N2 H21 . 0.8600 ?
C1 C11 . 1.496(5) ?
C11 C12 . 1.503(5) ?
C11 H112 . 0.9700 ?
C11 H111 . 0.9700 ?
C12 C13 . 1.506(7) ?
C12 H122 . 0.9700 ?
C12 H121 . 0.9700 ?
C13 C14 . 1.526(8) ?
C13 C15 . 1.531(9) ?
C13 H131 . 0.9800 ?
C14 H143 . 0.9600 ?
C14 H142 . 0.9600 ?
C14 H141 . 0.9600 ?
C15 H152 . 0.9600 ?
C15 H153 . 0.9600 ?
C15 H151 . 0.9600 ?
C21 C22 . 1.495(5) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 H223 . 0.9600 ?
C22 H222 . 0.9600 ?
C22 H221 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 129.9(3) ?
C1 N1 H11 . . 115.1 ?
C2 N1 H11 . . 115.1 ?
C2 N2 C21 . . 121.7(3) ?
C2 N2 H21 . . 119.2 ?
C21 N2 H21 . . 119.2 ?
O1 C1 N1 . . 122.3(3) ?
O1 C1 C11 . . 122.2(3) ?
N1 C1 C11 . . 115.5(3) ?
O2 C2 N2 . . 123.6(3) ?
O2 C2 N1 . . 118.4(3) ?
N2 C2 N1 . . 118.0(3) ?
C1 C11 C12 . . 114.6(3) ?
C1 C11 H112 . . 108.6 ?
C12 C11 H112 . . 108.6 ?
C1 C11 H111 . . 108.6 ?
C12 C11 H111 . . 108.6 ?
H112 C11 H111 . . 107.6 ?
C11 C12 C13 . . 114.1(3) ?
C11 C12 H122 . . 108.7 ?
C13 C12 H122 . . 108.7 ?
C11 C12 H121 . . 108.7 ?
C13 C12 H121 . . 108.7 ?
H122 C12 H121 . . 107.6 ?
C12 C13 C14 . . 109.6(5) ?
C12 C13 C15 . . 111.0(4) ?
C14 C13 C15 . . 108.8(5) ?
C12 C13 H131 . . 109.1 ?
C14 C13 H131 . . 109.1 ?
C15 C13 H131 . . 109.1 ?
C13 C14 H143 . . 109.5 ?
C13 C14 H142 . . 109.5 ?
H143 C14 H142 . . 109.5 ?
C13 C14 H141 . . 109.5 ?
H143 C14 H141 . . 109.5 ?
H142 C14 H141 . . 109.5 ?
C13 C15 H152 . . 109.5 ?
C13 C15 H153 . . 109.5 ?
H152 C15 H153 . . 109.5 ?
C13 C15 H151 . . 109.5 ?
H152 C15 H151 . . 109.5 ?
H153 C15 H151 . . 109.5 ?
N2 C21 C22 . . 112.6(3) ?
N2 C21 H211 . . 109.1 ?
C22 C21 H211 . . 109.1 ?
N2 C21 H212 . . 109.1 ?
C22 C21 H212 . . 109.1 ?
H211 C21 H212 . . 107.8 ?
C21 C22 H223 . . 109.5 ?
C21 C22 H222 . . 109.5 ?
H223 C22 H222 . . 109.5 ?
C21 C22 H221 . . 109.5 ?
H223 C22 H221 . . 109.5 ?
H222 C22 H221 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 3.0(5) ?
C2 N1 C1 C11 . . . . -176.5(3) ?
C21 N2 C2 O2 . . . . -1.0(5) ?
C21 N2 C2 N1 . . . . 178.3(3) ?
C1 N1 C2 O2 . . . . 179.3(3) ?
C1 N1 C2 N2 . . . . 0.1(5) ?
O1 C1 C11 C12 . . . . 55.3(4) ?
N1 C1 C11 C12 . . . . -125.3(3) ?
C1 C11 C12 C13 . . . . 65.7(5) ?
C11 C12 C13 C14 . . . . -175.0(4) ?
C11 C12 C13 C15 . . . . 64.8(6) ?
C2 N2 C21 C22 . . . . -82.8(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.86 2.39 3.069(3) 136.8
N1 H11 O2 2_566 0.86 2.00 2.859(3) 177.2
data_ethyl350K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.7514(15)
_cell_length_b 12.460(2)
_cell_length_c 5.1254(9)
_cell_angle_alpha 91.510(5)
_cell_angle_beta 90.273(9)
_cell_angle_gamma 89.642(8)
_cell_volume 558.69(16)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 4431
_cell_measurement_theta_min 2.855
_cell_measurement_theta_max 27.425
_cell_measurement_temperature 350
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 0.80
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.107
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.078
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being low temperature phase.
;
_diffrn_ambient_temperature 350
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 6495
_diffrn_reflns_av_R_equivalents 0.021
_diffrn_reflns_av_sigmaI/netI 0.0130
_diffrn_reflns_theta_min 2.33
_diffrn_reflns_theta_max 27.48
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_max 0.826
_diffrn_measured_fraction_theta_full 0.826
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 2118
_reflns_number_gt 1790
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1347
_refine_ls_R_factor_gt 0.1195
_refine_ls_wR_factor_gt 0.2409
_refine_ls_wR_factor_ref 0.2498
_refine_ls_goodness_of_fit_ref 1.344
_refine_ls_restrained_S_all 1.348
_refine_ls_number_reflns 2118
_refine_ls_number_parameters 118
_refine_ls_number_restraints 6
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+0.4679P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.201
_refine_diff_density_min -0.217
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 348K was used as an initial model.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.4331(3) 0.5744(2) 0.2313(6) 0.0800(9) Uani d . 1 . . O
O2 0.0270(3) 0.4095(2) 0.2386(6) 0.0797(9) Uani d . 1 . . O
N1 0.1970(3) 0.5338(3) 0.3786(7) 0.0657(9) Uani d . 1 . . N
H11 0.1304 0.5529 0.4939 0.079 Uiso calc R 1 . . H
N2 0.2526(4) 0.4162(3) 0.0302(7) 0.0683(9) Uani d D 1 . . N
H12 0.3392 0.4478 0.0190 0.082 Uiso calc R 1 . . H
C1 0.3300(4) 0.5901(3) 0.3871(8) 0.0623(10) Uani d . 1 . . C
C2 0.1535(4) 0.4499(3) 0.2105(8) 0.0633(10) Uani d D 1 . . C
C11 0.3413(5) 0.6722(3) 0.6048(9) 0.0775(12) Uani d D 1 . . C
H112 0.4203 0.6496 0.7252 0.093 Uiso calc R 1 . . H
H111 0.2453 0.6739 0.6988 0.093 Uiso calc R 1 . . H
C12 0.3767(6) 0.7844(4) 0.5202(11) 0.1012(17) Uani d D 1 . . C
H122 0.3968 0.8289 0.6746 0.121 Uiso calc R 1 . . H
H121 0.4694 0.7820 0.4172 0.121 Uiso calc R 1 . . H
C13 0.2530(8) 0.8371(5) 0.3637(13) 0.123(2) Uani d D 1 . . C
H131 0.2292 0.7913 0.2107 0.148 Uiso calc R 1 . . H
C14 0.3071(13) 0.9459(5) 0.2724(18) 0.201(5) Uani d D 1 . . C
H143 0.2277 0.9788 0.1718 0.242 Uiso calc R 1 . . H
H142 0.3966 0.9362 0.1666 0.242 Uiso calc R 1 . . H
H141 0.3310 0.9911 0.4214 0.242 Uiso calc R 1 . . H
C15 0.1083(8) 0.8548(7) 0.523(2) 0.192(4) Uani d D 1 . . C
H152 0.0741 0.7873 0.5872 0.230 Uiso calc R 1 . . H
H153 0.0301 0.8852 0.4154 0.230 Uiso calc R 1 . . H
H151 0.1294 0.9030 0.6681 0.230 Uiso calc R 1 . . H
C21 0.2183(5) 0.3279(4) -0.1466(9) 0.0788(12) Uani d D 1 . . C
H211 0.2785 0.3348 -0.3037 0.095 Uiso calc R 1 . . H
H212 0.1113 0.3317 -0.1959 0.095 Uiso calc R 1 . . H
C22 0.2505(7) 0.2204(4) -0.0324(12) 0.1091(18) Uani d D 1 . . C
H223 0.2262 0.1647 -0.1586 0.131 Uiso calc R 1 . . H
H222 0.1891 0.2121 0.1205 0.131 Uiso calc R 1 . . H
H221 0.3567 0.2155 0.0141 0.131 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0511(15) 0.095(2) 0.094(2) -0.0123(14) 0.0241(15) -0.0030(17)
O2 0.0525(16) 0.092(2) 0.095(2) -0.0142(14) 0.0228(14) -0.0050(17)
N1 0.0484(17) 0.073(2) 0.076(2) -0.0032(14) 0.0209(15) -0.0020(17)
N2 0.0504(17) 0.074(2) 0.080(2) -0.0057(15) 0.0134(16) -0.0016(18)
C1 0.049(2) 0.067(2) 0.072(2) 0.0016(17) 0.0082(18) 0.0141(19)
C2 0.0451(19) 0.071(2) 0.075(3) 0.0033(17) 0.0150(18) 0.010(2)
C11 0.064(3) 0.082(3) 0.087(3) -0.006(2) 0.010(2) 0.004(2)
C12 0.087(4) 0.097(4) 0.120(4) -0.012(3) 0.026(3) -0.005(3)
C13 0.145(6) 0.105(4) 0.120(5) 0.005(4) -0.020(4) 0.015(4)
C14 0.316(14) 0.098(5) 0.192(9) -0.006(7) 0.019(9) 0.047(6)
C15 0.109(6) 0.147(7) 0.321(14) 0.029(5) -0.021(7) 0.029(8)
C21 0.060(2) 0.092(3) 0.084(3) -0.003(2) 0.010(2) -0.001(3)
C22 0.114(4) 0.086(4) 0.127(5) 0.002(3) 0.010(4) -0.001(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.219(4) ?
O2 C2 . 1.230(4) ?
N1 C1 . 1.362(5) ?
N1 C2 . 1.391(5) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.329(5) ?
N2 C21 . 1.438(5) ?
N2 H12 . 0.8600 ?
C1 C11 . 1.496(6) ?
C11 C12 . 1.510(7) ?
C11 H112 . 0.9700 ?
C11 H111 . 0.9700 ?
C12 C13 . 1.502(9) ?
C12 H122 . 0.9700 ?
C12 H121 . 0.9700 ?
C13 C15 . 1.523(11) ?
C13 C14 . 1.524(10) ?
C13 H131 . 0.9800 ?
C14 H143 . 0.9600 ?
C14 H142 . 0.9600 ?
C14 H141 . 0.9600 ?
C15 H152 . 0.9600 ?
C15 H153 . 0.9600 ?
C15 H151 . 0.9600 ?
C21 C22 . 1.501(7) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 H223 . 0.9600 ?
C22 H222 . 0.9600 ?
C22 H221 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 129.3(3) ?
C1 N1 H11 . . 115.3 ?
C2 N1 H11 . . 115.3 ?
C2 N2 C21 . . 121.6(3) ?
C2 N2 H12 . . 119.2 ?
C21 N2 H12 . . 119.2 ?
O1 C1 N1 . . 122.8(4) ?
O1 C1 C11 . . 122.3(4) ?
N1 C1 C11 . . 115.0(3) ?
O2 C2 N2 . . 123.3(4) ?
O2 C2 N1 . . 118.7(3) ?
N2 C2 N1 . . 118.0(3) ?
C1 C11 C12 . . 114.8(4) ?
C1 C11 H112 . . 108.6 ?
C12 C11 H112 . . 108.6 ?
C1 C11 H111 . . 108.6 ?
C12 C11 H111 . . 108.6 ?
H112 C11 H111 . . 107.5 ?
C13 C12 C11 . . 115.0(4) ?
C13 C12 H122 . . 108.5 ?
C11 C12 H122 . . 108.5 ?
C13 C12 H121 . . 108.5 ?
C11 C12 H121 . . 108.5 ?
H122 C12 H121 . . 107.5 ?
C12 C13 C15 . . 111.6(6) ?
C12 C13 C14 . . 110.0(6) ?
C15 C13 C14 . . 108.2(7) ?
C12 C13 H131 . . 109.0 ?
C15 C13 H131 . . 109.0 ?
C14 C13 H131 . . 109.0 ?
C13 C14 H143 . . 109.5 ?
C13 C14 H142 . . 109.5 ?
H143 C14 H142 . . 109.5 ?
C13 C14 H141 . . 109.5 ?
H143 C14 H141 . . 109.5 ?
H142 C14 H141 . . 109.5 ?
C13 C15 H152 . . 109.5 ?
C13 C15 H153 . . 109.5 ?
H152 C15 H153 . . 109.5 ?
C13 C15 H151 . . 109.5 ?
H152 C15 H151 . . 109.5 ?
H153 C15 H151 . . 109.5 ?
N2 C21 C22 . . 113.1(4) ?
N2 C21 H211 . . 109.0 ?
C22 C21 H211 . . 109.0 ?
N2 C21 H212 . . 109.0 ?
C22 C21 H212 . . 109.0 ?
H211 C21 H212 . . 107.8 ?
C21 C22 H223 . . 109.5 ?
C21 C22 H222 . . 109.5 ?
H223 C22 H222 . . 109.5 ?
C21 C22 H221 . . 109.5 ?
H223 C22 H221 . . 109.5 ?
H222 C22 H221 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 2.3(7) ?
C2 N1 C1 C11 . . . . -176.9(4) ?
C21 N2 C2 O2 . . . . -0.4(6) ?
C21 N2 C2 N1 . . . . 178.3(4) ?
C1 N1 C2 O2 . . . . 179.4(4) ?
C1 N1 C2 N2 . . . . 0.7(6) ?
O1 C1 C11 C12 . . . . 55.4(6) ?
N1 C1 C11 C12 . . . . -125.3(4) ?
C1 C11 C12 C13 . . . . 66.8(6) ?
C11 C12 C13 C15 . . . . 64.3(7) ?
C11 C12 C13 C14 . . . . -175.6(5) ?
C2 N2 C21 C22 . . . . -83.5(5) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H12 O1 2_665 0.86 2.39 3.070(4) 136.9
N1 H11 O2 2_566 0.86 1.99 2.853(4) 177.5
data_ethyl352K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.7503(15)
_cell_length_b 12.4205(13)
_cell_length_c 5.0998(3)
_cell_angle_alpha 90.921(8)
_cell_angle_beta 89.723(12)
_cell_angle_gamma 89.714(10)
_cell_volume 554.18(12)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2561
_cell_measurement_theta_min 1.64
_cell_measurement_theta_max 27.165
_cell_measurement_temperature 352
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 0.80
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.116
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.079
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being low temperature phase.
;
_diffrn_ambient_temperature 352
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 6495
_diffrn_reflns_av_R_equivalents 0.043
_diffrn_reflns_av_sigmaI/netI 0.0258
_diffrn_reflns_theta_min 2.84
_diffrn_reflns_theta_max 27.48
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_max 0.773
_diffrn_measured_fraction_theta_full 0.773
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 1968
_reflns_number_gt 1242
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1531
_refine_ls_R_factor_gt 0.1090
_refine_ls_wR_factor_gt 0.3116
_refine_ls_wR_factor_ref 0.3573
_refine_ls_goodness_of_fit_ref 2.279
_refine_ls_restrained_S_all 2.288
_refine_ls_number_reflns 1968
_refine_ls_number_parameters 118
_refine_ls_number_restraints 5
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.245
_refine_diff_density_min -0.272
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 350K was used as an initial model.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.4334(3) 0.5747(3) 0.2302(6) 0.0916(10) Uani d . 1 . . O
O2 0.0271(3) 0.4095(2) 0.2407(6) 0.0884(10) Uani d . 1 . . O
N1 0.1975(4) 0.5334(3) 0.3774(6) 0.0736(10) Uani d . 1 . . N
H11 0.1306 0.5514 0.4943 0.088 Uiso calc R 1 . . H
N2 0.2528(4) 0.4164(3) 0.0297(6) 0.0762(10) Uani d . 1 . . N
H21 0.3397 0.4480 0.0171 0.091 Uiso calc R 1 . . H
C1 0.3279(4) 0.5905(3) 0.3858(8) 0.0713(10) Uani d . 1 . . C
C2 0.1544(5) 0.4503(3) 0.2098(8) 0.0745(10) Uani d . 1 . . C
C11 0.3418(5) 0.6719(3) 0.6031(9) 0.0841(12) Uani d D 1 . . C
H112 0.4200 0.6475 0.7228 0.101 Uiso calc R 1 . . H
H111 0.2460 0.6746 0.6992 0.101 Uiso calc R 1 . . H
C12 0.3806(6) 0.7842(4) 0.5206(11) 0.1075(17) Uani d D 1 . . C
H122 0.4733 0.7820 0.4156 0.129 Uiso calc R 1 . . H
H121 0.4004 0.8281 0.6756 0.129 Uiso calc R 1 . . H
C13 0.2535(8) 0.8365(5) 0.3631(12) 0.131(2) Uani d D 1 . . C
H131 0.2308 0.7903 0.2109 0.157 Uiso calc R 1 . . H
C14 0.3088(15) 0.9449(6) 0.2663(19) 0.220(6) Uani d D 1 . . C
H142 0.4007 0.9348 0.1651 0.264 Uiso calc R 1 . . H
H141 0.3291 0.9916 0.4139 0.264 Uiso calc R 1 . . H
H143 0.2315 0.9768 0.1589 0.264 Uiso calc R 1 . . H
C15 0.1084(8) 0.8520(7) 0.524(2) 0.188(4) Uani d D 1 . . C
H152 0.0739 0.7835 0.5849 0.225 Uiso calc R 1 . . H
H153 0.0308 0.8839 0.4178 0.225 Uiso calc R 1 . . H
H151 0.1289 0.8984 0.6722 0.225 Uiso calc R 1 . . H
C21 0.2191(5) 0.3275(4) -0.1474(9) 0.0883(13) Uani d D 1 . . C
H211 0.2798 0.3347 -0.3057 0.106 Uiso calc R 1 . . H
H212 0.1122 0.3313 -0.1964 0.106 Uiso calc R 1 . . H
C22 0.2506(8) 0.2200(4) -0.0318(13) 0.1205(19) Uani d D 1 . . C
H223 0.2263 0.1644 -0.1575 0.145 Uiso calc R 1 . . H
H222 0.1890 0.2115 0.1227 0.145 Uiso calc R 1 . . H
H221 0.3567 0.2150 0.0136 0.145 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0625(17) 0.104(2) 0.108(2) -0.0180(14) 0.0261(15) -0.0071(17)
O2 0.0576(17) 0.101(2) 0.106(2) -0.0170(13) 0.0298(14) -0.0096(16)
N1 0.0580(18) 0.081(2) 0.0813(19) -0.0088(14) 0.0220(14) -0.0016(16)
N2 0.0542(18) 0.085(2) 0.089(2) -0.0068(14) 0.0168(15) -0.0017(17)
C1 0.0460(18) 0.081(2) 0.087(2) 0.0021(15) 0.0141(15) 0.017(2)
C2 0.055(2) 0.082(2) 0.086(2) -0.0021(16) 0.0158(17) 0.010(2)
C11 0.071(3) 0.082(2) 0.098(3) -0.0082(19) 0.010(2) 0.004(2)
C12 0.084(3) 0.103(4) 0.135(4) -0.012(3) 0.024(3) -0.009(3)
C13 0.162(7) 0.108(4) 0.123(5) 0.003(4) -0.011(4) 0.011(3)
C14 0.34(2) 0.125(6) 0.193(9) 0.002(7) 0.005(10) 0.047(6)
C15 0.105(6) 0.165(7) 0.294(12) 0.022(5) -0.012(7) 0.029(7)
C21 0.067(3) 0.096(3) 0.101(3) -0.008(2) 0.018(2) -0.005(2)
C22 0.133(5) 0.098(4) 0.130(5) 0.008(3) 0.007(4) -0.003(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.228(4) ?
O2 C2 . 1.237(5) ?
N1 C1 . 1.346(5) ?
N1 C2 . 1.384(5) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.319(5) ?
N2 C21 . 1.448(5) ?
N2 H21 . 0.8600 ?
C1 C11 . 1.494(6) ?
C11 C12 . 1.503(6) ?
C11 H112 . 0.9700 ?
C11 H111 . 0.9700 ?
C12 C13 . 1.524(8) ?
C12 H122 . 0.9700 ?
C12 H121 . 0.9700 ?
C13 C15 . 1.519(11) ?
C13 C14 . 1.522(10) ?
C13 H131 . 0.9800 ?
C14 H142 . 0.9600 ?
C14 H141 . 0.9600 ?
C14 H143 . 0.9600 ?
C15 H152 . 0.9600 ?
C15 H153 . 0.9600 ?
C15 H151 . 0.9600 ?
C21 C22 . 1.493(7) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 H223 . 0.9600 ?
C22 H222 . 0.9600 ?
C22 H221 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 130.1(3) ?
C1 N1 H11 . . 114.9 ?
C2 N1 H11 . . 114.9 ?
C2 N2 C21 . . 122.0(4) ?
C2 N2 H21 . . 119.0 ?
C21 N2 H21 . . 119.0 ?
O1 C1 N1 . . 122.4(4) ?
O1 C1 C11 . . 120.8(4) ?
N1 C1 C11 . . 116.7(3) ?
O2 C2 N2 . . 123.1(4) ?
O2 C2 N1 . . 118.5(3) ?
N2 C2 N1 . . 118.4(4) ?
C1 C11 C12 . . 115.6(4) ?
C1 C11 H112 . . 108.4 ?
C12 C11 H112 . . 108.4 ?
C1 C11 H111 . . 108.4 ?
C12 C11 H111 . . 108.4 ?
H112 C11 H111 . . 107.4 ?
C11 C12 C13 . . 112.7(4) ?
C11 C12 H122 . . 109.1 ?
C13 C12 H122 . . 109.1 ?
C11 C12 H121 . . 109.1 ?
C13 C12 H121 . . 109.1 ?
H122 C12 H121 . . 107.8 ?
C15 C13 C14 . . 109.7(8) ?
C15 C13 C12 . . 112.0(5) ?
C14 C13 C12 . . 108.9(6) ?
C15 C13 H131 . . 108.7 ?
C14 C13 H131 . . 108.7 ?
C12 C13 H131 . . 108.7 ?
C13 C14 H142 . . 109.5 ?
C13 C14 H141 . . 109.5 ?
H142 C14 H141 . . 109.5 ?
C13 C14 H143 . . 109.5 ?
H142 C14 H143 . . 109.5 ?
H141 C14 H143 . . 109.5 ?
C13 C15 H152 . . 109.5 ?
C13 C15 H153 . . 109.5 ?
H152 C15 H153 . . 109.5 ?
C13 C15 H151 . . 109.5 ?
H152 C15 H151 . . 109.5 ?
H153 C15 H151 . . 109.5 ?
N2 C21 C22 . . 113.2(4) ?
N2 C21 H211 . . 108.9 ?
C22 C21 H211 . . 108.9 ?
N2 C21 H212 . . 108.9 ?
C22 C21 H212 . . 108.9 ?
H211 C21 H212 . . 107.8 ?
C21 C22 H223 . . 109.5 ?
C21 C22 H222 . . 109.5 ?
H223 C22 H222 . . 109.5 ?
C21 C22 H221 . . 109.5 ?
H223 C22 H221 . . 109.5 ?
H222 C22 H221 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 0.6(6) ?
C2 N1 C1 C11 . . . . -176.8(3) ?
C21 N2 C2 O2 . . . . -0.2(6) ?
C21 N2 C2 N1 . . . . 177.8(3) ?
C1 N1 C2 O2 . . . . 179.9(4) ?
C1 N1 C2 N2 . . . . 1.8(6) ?
O1 C1 C11 C12 . . . . 55.9(5) ?
N1 C1 C11 C12 . . . . -126.7(4) ?
C1 C11 C12 C13 . . . . 66.3(6) ?
C11 C12 C13 C15 . . . . 63.9(8) ?
C11 C12 C13 C14 . . . . -174.6(6) ?
C2 N2 C21 C22 . . . . -83.5(5) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.86 2.36 3.047(4) 137.0
N1 H11 O2 2_566 0.86 1.98 2.840(4) 178.6
data_ethyl354K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.7270(4)
_cell_length_b 12.6010(13)
_cell_length_c 5.1459(3)
_cell_angle_alpha 91.317(9)
_cell_angle_beta 90.331(11)
_cell_angle_gamma 89.001(9)
_cell_volume 565.65(7)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 4364
_cell_measurement_theta_min 2.865
_cell_measurement_theta_max 27.455
_cell_measurement_temperature 354
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 0.80
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.094
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.077
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being low temperature phase.
;
_diffrn_ambient_temperature 354
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 6513
_diffrn_reflns_av_R_equivalents 0.026
_diffrn_reflns_av_sigmaI/netI 0.0175
_diffrn_reflns_theta_min 2.33
_diffrn_reflns_theta_max 27.48
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_max 0.815
_diffrn_measured_fraction_theta_full 0.815
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 2122
_reflns_number_gt 1551
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1465
_refine_ls_R_factor_gt 0.1175
_refine_ls_wR_factor_gt 0.2594
_refine_ls_wR_factor_ref 0.2768
_refine_ls_goodness_of_fit_ref 1.305
_refine_ls_restrained_S_all 1.309
_refine_ls_number_reflns 2122
_refine_ls_number_parameters 118
_refine_ls_number_restraints 5
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0663P)^2^+0.4317P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.221
_refine_diff_density_min -0.222
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 352K was used as an initial model.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.4326(3) 0.5747(3) 0.2307(7) 0.0861(10) Uani d . 1 . . O
O2 0.0267(3) 0.4098(3) 0.2401(7) 0.0852(10) Uani d . 1 . . O
N1 0.1973(4) 0.5339(3) 0.3778(7) 0.0709(10) Uani d . 1 . . N
H11 0.1303 0.5531 0.4923 0.085 Uiso calc R 1 . . H
N2 0.2522(4) 0.4164(3) 0.0306(7) 0.0712(10) Uani d . 1 . . N
H21 0.3383 0.4480 0.0169 0.085 Uiso calc R 1 . . H
C1 0.3297(4) 0.5903(3) 0.3861(9) 0.0666(11) Uani d . 1 . . C
C2 0.1532(4) 0.4496(3) 0.2123(9) 0.0661(11) Uani d . 1 . . C
C11 0.3404(5) 0.6721(4) 0.6014(10) 0.0811(13) Uani d D 1 . . C
H112 0.4189 0.6492 0.7229 0.097 Uiso calc R 1 . . H
H111 0.2437 0.6747 0.6937 0.097 Uiso calc R 1 . . H
C12 0.3767(7) 0.7834(4) 0.5180(13) 0.112(2) Uani d D 1 . . C
H121 0.3964 0.8268 0.6723 0.134 Uiso calc R 1 . . H
H122 0.4702 0.7803 0.4168 0.134 Uiso calc R 1 . . H
C13 0.2538(8) 0.8369(5) 0.3608(14) 0.131(2) Uani d D 1 . . C
H131 0.2307 0.7922 0.2078 0.157 Uiso calc R 1 . . H
C14 0.3074(14) 0.9447(6) 0.271(2) 0.219(5) Uani d D 1 . . C
H143 0.2279 0.9777 0.1698 0.262 Uiso calc R 1 . . H
H142 0.3976 0.9350 0.1663 0.262 Uiso calc R 1 . . H
H141 0.3305 0.9890 0.4195 0.262 Uiso calc R 1 . . H
C15 0.1081(9) 0.8545(7) 0.518(2) 0.209(5) Uani d D 1 . . C
H152 0.0748 0.7879 0.5821 0.250 Uiso calc R 1 . . H
H153 0.0296 0.8843 0.4088 0.250 Uiso calc R 1 . . H
H151 0.1280 0.9024 0.6613 0.250 Uiso calc R 1 . . H
C21 0.2180(5) 0.3283(4) -0.1443(10) 0.0819(13) Uani d D 1 . . C
H211 0.2783 0.3345 -0.3009 0.098 Uiso calc R 1 . . H
H212 0.1107 0.3328 -0.1938 0.098 Uiso calc R 1 . . H
C22 0.2503(8) 0.2210(4) -0.0295(13) 0.116(2) Uani d D 1 . . C
H223 0.2251 0.1663 -0.1547 0.140 Uiso calc R 1 . . H
H222 0.1893 0.2134 0.1234 0.140 Uiso calc R 1 . . H
H221 0.3569 0.2150 0.0157 0.140 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0583(17) 0.102(2) 0.098(2) -0.0109(15) 0.0267(16) -0.0047(19)
O2 0.0544(16) 0.100(2) 0.102(2) -0.0142(15) 0.0237(15) -0.0063(18)
N1 0.0523(18) 0.079(2) 0.082(2) -0.0025(16) 0.0237(17) 0.001(2)
N2 0.0510(18) 0.082(2) 0.081(2) -0.0032(16) 0.0158(16) -0.0026(19)
C1 0.053(2) 0.071(3) 0.077(3) 0.0035(18) 0.0116(19) 0.016(2)
C2 0.049(2) 0.074(3) 0.076(3) 0.0056(18) 0.0106(19) 0.014(2)
C11 0.068(3) 0.083(3) 0.092(3) -0.003(2) 0.014(2) 0.005(3)
C12 0.098(4) 0.106(4) 0.132(5) -0.011(3) 0.028(4) -0.010(4)
C13 0.151(7) 0.113(5) 0.129(6) 0.014(5) -0.017(5) 0.025(4)
C14 0.342(16) 0.108(6) 0.208(10) -0.001(8) 0.033(10) 0.045(6)
C15 0.120(7) 0.166(8) 0.340(16) 0.035(6) -0.023(9) 0.032(9)
C21 0.062(2) 0.098(3) 0.086(3) -0.002(2) 0.012(2) 0.000(3)
C22 0.121(5) 0.092(4) 0.136(5) 0.003(3) 0.012(4) -0.001(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.217(5) ?
O2 C2 . 1.232(5) ?
N1 C1 . 1.367(5) ?
N1 C2 . 1.403(6) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.332(5) ?
N2 C21 . 1.447(6) ?
N2 H21 . 0.8600 ?
C1 C11 . 1.499(6) ?
C11 C12 . 1.516(7) ?
C11 H112 . 0.9700 ?
C11 H111 . 0.9700 ?
C12 C13 . 1.500(9) ?
C12 H121 . 0.9700 ?
C12 H122 . 0.9700 ?
C13 C15 . 1.520(11) ?
C13 C14 . 1.527(11) ?
C13 H131 . 0.9800 ?
C14 H143 . 0.9600 ?
C14 H142 . 0.9600 ?
C14 H141 . 0.9600 ?
C15 H152 . 0.9600 ?
C15 H153 . 0.9600 ?
C15 H151 . 0.9600 ?
C21 C22 . 1.510(8) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 H223 . 0.9600 ?
C22 H222 . 0.9600 ?
C22 H221 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 130.3(3) ?
C1 N1 H11 . . 114.9 ?
C2 N1 H11 . . 114.9 ?
C2 N2 C21 . . 121.4(4) ?
C2 N2 H21 . . 119.3 ?
C21 N2 H21 . . 119.3 ?
O1 C1 N1 . . 122.4(4) ?
O1 C1 C11 . . 122.1(4) ?
N1 C1 C11 . . 115.5(4) ?
O2 C2 N2 . . 123.0(4) ?
O2 C2 N1 . . 119.4(4) ?
N2 C2 N1 . . 117.6(3) ?
C1 C11 C12 . . 115.6(4) ?
C1 C11 H112 . . 108.4 ?
C12 C11 H112 . . 108.4 ?
C1 C11 H111 . . 108.4 ?
C12 C11 H111 . . 108.4 ?
H112 C11 H111 . . 107.4 ?
C13 C12 C11 . . 115.0(5) ?
C13 C12 H121 . . 108.5 ?
C11 C12 H121 . . 108.5 ?
C13 C12 H122 . . 108.5 ?
C11 C12 H122 . . 108.5 ?
H121 C12 H122 . . 107.5 ?
C12 C13 C15 . . 111.4(6) ?
C12 C13 C14 . . 110.5(7) ?
C15 C13 C14 . . 108.2(8) ?
C12 C13 H131 . . 108.9 ?
C15 C13 H131 . . 108.9 ?
C14 C13 H131 . . 108.9 ?
C13 C14 H143 . . 109.5 ?
C13 C14 H142 . . 109.5 ?
H143 C14 H142 . . 109.5 ?
C13 C14 H141 . . 109.5 ?
H143 C14 H141 . . 109.5 ?
H142 C14 H141 . . 109.5 ?
C13 C15 H152 . . 109.5 ?
C13 C15 H153 . . 109.5 ?
H152 C15 H153 . . 109.5 ?
C13 C15 H151 . . 109.5 ?
H152 C15 H151 . . 109.5 ?
H153 C15 H151 . . 109.5 ?
N2 C21 C22 . . 113.7(4) ?
N2 C21 H211 . . 108.8 ?
C22 C21 H211 . . 108.8 ?
N2 C21 H212 . . 108.8 ?
C22 C21 H212 . . 108.8 ?
H211 C21 H212 . . 107.7 ?
C21 C22 H223 . . 109.5 ?
C21 C22 H222 . . 109.5 ?
H223 C22 H222 . . 109.5 ?
C21 C22 H221 . . 109.5 ?
H223 C22 H221 . . 109.5 ?
H222 C22 H221 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 2.7(7) ?
C2 N1 C1 C11 . . . . -176.8(4) ?
C21 N2 C2 O2 . . . . -1.5(7) ?
C21 N2 C2 N1 . . . . 178.4(4) ?
C1 N1 C2 O2 . . . . 179.8(4) ?
C1 N1 C2 N2 . . . . -0.1(6) ?
O1 C1 C11 C12 . . . . 54.2(6) ?
N1 C1 C11 C12 . . . . -126.4(4) ?
C1 C11 C12 C13 . . . . 66.9(6) ?
C11 C12 C13 C15 . . . . 64.0(8) ?
C11 C12 C13 C14 . . . . -175.8(6) ?
C2 N2 C21 C22 . . . . -82.3(5) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.86 2.39 3.073(4) 137.1
N1 H11 O2 2_566 0.86 1.99 2.850(5) 177.3
data_ethyl356K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.726(3)
_cell_length_b 12.460(3)
_cell_length_c 5.1382(12)
_cell_angle_alpha 91.423(6)
_cell_angle_beta 90.143(10)
_cell_angle_gamma 89.297(11)
_cell_volume 558.5(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2070
_cell_measurement_theta_min 2.335
_cell_measurement_theta_max 27.48
_cell_measurement_temperature 356
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 0.80
_exptl_crystal_size_mid 0.80
_exptl_crystal_size_min 0.20
_exptl_crystal_density_diffrn 1.108
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.078
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being low temperature phase.
;
_diffrn_ambient_temperature 356
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 6409
_diffrn_reflns_av_R_equivalents 0.035
_diffrn_reflns_av_sigmaI/netI 0.0210
_diffrn_reflns_theta_min 2.33
_diffrn_reflns_theta_max 27.47
_diffrn_reflns_theta_full 27.47
_diffrn_measured_fraction_theta_max 0.668
_diffrn_measured_fraction_theta_full 0.668
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 1713
_reflns_number_gt 1306
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0991
_refine_ls_R_factor_gt 0.0792
_refine_ls_wR_factor_gt 0.2200
_refine_ls_wR_factor_ref 0.2495
_refine_ls_goodness_of_fit_ref 1.081
_refine_ls_restrained_S_all 1.087
_refine_ls_number_reflns 1713
_refine_ls_number_parameters 118
_refine_ls_number_restraints 5
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1254P)^2^+0.2162P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.228
_refine_diff_density_min -0.243
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 354K was used as an initial model.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.4321(3) 0.5743(2) 0.2297(5) 0.0906(8) Uani d . 1 . . O
O2 0.0271(3) 0.4103(2) 0.2409(5) 0.0873(8) Uani d . 1 . . O
N1 0.1970(3) 0.5337(2) 0.3769(5) 0.0726(8) Uani d . 1 . . N
H11 0.1302 0.5527 0.4923 0.087 Uiso calc R 1 . . H
N2 0.2523(3) 0.4164(2) 0.0323(5) 0.0759(8) Uani d . 1 . . N
H21 0.3390 0.4479 0.0207 0.091 Uiso calc R 1 . . H
C1 0.3290(4) 0.5900(3) 0.3840(6) 0.0721(9) Uani d . 1 . . C
C2 0.1537(4) 0.4496(3) 0.2106(6) 0.0708(8) Uani d . 1 . . C
C11 0.3411(4) 0.6720(3) 0.5999(7) 0.0851(10) Uani d D 1 . . C
H112 0.4200 0.6487 0.7200 0.102 Uiso calc R 1 . . H
H111 0.2448 0.6746 0.6940 0.102 Uiso calc R 1 . . H
C12 0.3775(5) 0.7834(3) 0.5164(10) 0.1125(14) Uani d D 1 . . C
H122 0.4708 0.7803 0.4140 0.135 Uiso calc R 1 . . H
H121 0.3975 0.8276 0.6705 0.135 Uiso calc R 1 . . H
C13 0.2533(7) 0.8369(4) 0.3592(11) 0.138(2) Uani d D 1 . . C
H131 0.2304 0.7911 0.2066 0.165 Uiso calc R 1 . . H
C14 0.3084(12) 0.9448(5) 0.2669(17) 0.217(4) Uani d D 1 . . C
H143 0.2299 0.9777 0.1636 0.260 Uiso calc R 1 . . H
H142 0.3993 0.9343 0.1639 0.260 Uiso calc R 1 . . H
H141 0.3309 0.9905 0.4149 0.260 Uiso calc R 1 . . H
C15 0.1063(8) 0.8539(6) 0.5178(19) 0.205(4) Uani d D 1 . . C
H152 0.0722 0.7861 0.5793 0.246 Uiso calc R 1 . . H
H153 0.0283 0.8849 0.4100 0.246 Uiso calc R 1 . . H
H151 0.1262 0.9014 0.6637 0.246 Uiso calc R 1 . . H
C21 0.2181(4) 0.3286(3) -0.1433(7) 0.0846(10) Uani d D 1 . . C
H211 0.2787 0.3350 -0.3000 0.102 Uiso calc R 1 . . H
H212 0.1109 0.3328 -0.1926 0.102 Uiso calc R 1 . . H
C22 0.2501(7) 0.2215(3) -0.0277(10) 0.1194(15) Uani d D 1 . . C
H223 0.2260 0.1656 -0.1528 0.143 Uiso calc R 1 . . H
H222 0.1882 0.2137 0.1248 0.143 Uiso calc R 1 . . H
H221 0.3564 0.2163 0.0189 0.143 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0631(14) 0.1048(18) 0.1040(17) -0.0101(12) 0.0276(13) -0.0024(14)
O2 0.0605(15) 0.0961(16) 0.1052(18) -0.0090(11) 0.0257(12) -0.0039(13)
N1 0.0594(15) 0.0782(17) 0.0803(16) -0.0007(12) 0.0216(12) 0.0030(13)
N2 0.0572(15) 0.0836(18) 0.0868(18) -0.0003(12) 0.0171(12) 0.0004(14)
C1 0.0579(18) 0.0747(19) 0.085(2) 0.0035(14) 0.0125(15) 0.0196(16)
C2 0.0550(17) 0.0787(19) 0.079(2) 0.0058(14) 0.0136(14) 0.0123(16)
C11 0.078(2) 0.082(2) 0.095(2) -0.0011(17) 0.0099(18) 0.0000(18)
C12 0.100(3) 0.103(3) 0.135(4) -0.010(2) 0.025(3) -0.006(3)
C13 0.165(6) 0.107(3) 0.142(4) 0.012(3) -0.021(4) 0.016(3)
C14 0.333(14) 0.110(4) 0.210(8) -0.003(6) 0.015(8) 0.047(5)
C15 0.122(6) 0.162(6) 0.331(12) 0.038(4) -0.011(7) 0.022(7)
C21 0.065(2) 0.097(2) 0.091(2) 0.0017(17) 0.0127(16) -0.0025(19)
C22 0.134(4) 0.092(3) 0.132(4) 0.007(3) 0.007(3) 0.003(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.211(4) ?
O2 C2 . 1.225(4) ?
N1 C1 . 1.357(4) ?
N1 C2 . 1.390(4) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.314(4) ?
N2 C21 . 1.435(4) ?
N2 H21 . 0.8600 ?
C1 C11 . 1.494(5) ?
C11 C12 . 1.501(6) ?
C11 H112 . 0.9700 ?
C11 H111 . 0.9700 ?
C12 C13 . 1.509(8) ?
C12 H122 . 0.9700 ?
C12 H121 . 0.9700 ?
C13 C14 . 1.520(9) ?
C13 C15 . 1.532(10) ?
C13 H131 . 0.9800 ?
C14 H143 . 0.9600 ?
C14 H142 . 0.9600 ?
C14 H141 . 0.9600 ?
C15 H152 . 0.9600 ?
C15 H153 . 0.9600 ?
C15 H151 . 0.9600 ?
C21 C22 . 1.497(6) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 H223 . 0.9600 ?
C22 H222 . 0.9600 ?
C22 H221 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 129.6(3) ?
C1 N1 H11 . . 115.2 ?
C2 N1 H11 . . 115.2 ?
C2 N2 C21 . . 121.3(3) ?
C2 N2 H21 . . 119.3 ?
C21 N2 H21 . . 119.3 ?
O1 C1 N1 . . 122.9(3) ?
O1 C1 C11 . . 121.7(3) ?
N1 C1 C11 . . 115.5(3) ?
O2 C2 N2 . . 124.1(3) ?
O2 C2 N1 . . 118.2(3) ?
N2 C2 N1 . . 117.7(3) ?
C1 C11 C12 . . 115.1(3) ?
C1 C11 H112 . . 108.5 ?
C12 C11 H112 . . 108.5 ?
C1 C11 H111 . . 108.5 ?
C12 C11 H111 . . 108.5 ?
H112 C11 H111 . . 107.5 ?
C11 C12 C13 . . 114.7(4) ?
C11 C12 H122 . . 108.6 ?
C13 C12 H122 . . 108.6 ?
C11 C12 H121 . . 108.6 ?
C13 C12 H121 . . 108.6 ?
H122 C12 H121 . . 107.6 ?
C12 C13 C14 . . 109.9(6) ?
C12 C13 C15 . . 111.6(5) ?
C14 C13 C15 . . 109.2(6) ?
C12 C13 H131 . . 108.7 ?
C14 C13 H131 . . 108.7 ?
C15 C13 H131 . . 108.7 ?
C13 C14 H143 . . 109.5 ?
C13 C14 H142 . . 109.5 ?
H143 C14 H142 . . 109.5 ?
C13 C14 H141 . . 109.5 ?
H143 C14 H141 . . 109.5 ?
H142 C14 H141 . . 109.5 ?
C13 C15 H152 . . 109.5 ?
C13 C15 H153 . . 109.5 ?
H152 C15 H153 . . 109.5 ?
C13 C15 H151 . . 109.5 ?
H152 C15 H151 . . 109.5 ?
H153 C15 H151 . . 109.5 ?
N2 C21 C22 . . 112.7(3) ?
N2 C21 H211 . . 109.0 ?
C22 C21 H211 . . 109.0 ?
N2 C21 H212 . . 109.0 ?
C22 C21 H212 . . 109.0 ?
H211 C21 H212 . . 107.8 ?
C21 C22 H223 . . 109.5 ?
C21 C22 H222 . . 109.5 ?
H223 C22 H222 . . 109.5 ?
C21 C22 H221 . . 109.5 ?
H223 C22 H221 . . 109.5 ?
H222 C22 H221 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 2.0(5) ?
C2 N1 C1 C11 . . . . -176.7(3) ?
C21 N2 C2 O2 . . . . -0.5(5) ?
C21 N2 C2 N1 . . . . 178.6(3) ?
C1 N1 C2 O2 . . . . 180.0(3) ?
C1 N1 C2 N2 . . . . 0.8(5) ?
O1 C1 C11 C12 . . . . 55.1(5) ?
N1 C1 C11 C12 . . . . -126.2(3) ?
C1 C11 C12 C13 . . . . 66.6(5) ?
C11 C12 C13 C14 . . . . -175.2(5) ?
C11 C12 C13 C15 . . . . 63.5(6) ?
C2 N2 C21 C22 . . . . -83.1(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.86 2.39 3.073(4) 137.0
N1 H11 O2 2_566 0.86 1.98 2.844(4) 177.3
data_ethyl358K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.7438(6)
_cell_length_b 12.5269(10)
_cell_length_c 5.1573(4)
_cell_angle_alpha 90.802(6)
_cell_angle_beta 90.388(7)
_cell_angle_gamma 89.224(3)
_cell_volume 564.77(7)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2719
_cell_measurement_theta_min 3.95
_cell_measurement_theta_max 27.385
_cell_measurement_temperature 358
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 1.00
_exptl_crystal_size_mid 1.00
_exptl_crystal_size_min 0.20
_exptl_crystal_density_diffrn 1.095
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.078
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being low temperature phase.
;
_diffrn_ambient_temperature 358
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 6499
_diffrn_reflns_av_R_equivalents 0.058
_diffrn_reflns_av_sigmaI/netI 0.0351
_diffrn_reflns_theta_min 2.33
_diffrn_reflns_theta_max 27.41
_diffrn_reflns_theta_full 27.41
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.931
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 2397
_reflns_number_gt 1516
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1360
_refine_ls_R_factor_gt 0.1033
_refine_ls_wR_factor_gt 0.2800
_refine_ls_wR_factor_ref 0.2975
_refine_ls_goodness_of_fit_ref 1.829
_refine_ls_restrained_S_all 1.839
_refine_ls_number_reflns 2397
_refine_ls_number_parameters 118
_refine_ls_number_restraints 5
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.360
_refine_diff_density_min -0.278
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 356K was used as an initial model.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.4322(2) 0.57411(19) 0.2289(5) 0.0866(7) Uani d . 1 . . O
O2 0.0270(2) 0.40995(18) 0.2426(5) 0.0839(7) Uani d . 1 . . O
N1 0.1973(2) 0.53358(18) 0.3763(5) 0.0685(7) Uani d . 1 . . N
H11 0.1306 0.5524 0.4905 0.082 Uiso calc R 1 . . H
N2 0.2522(3) 0.4163(2) 0.0331(5) 0.0731(7) Uani d . 1 . . N
H21 0.3389 0.4474 0.0215 0.088 Uiso calc R 1 . . H
C1 0.3293(3) 0.5898(2) 0.3831(6) 0.0685(8) Uani d . 1 . . C
C2 0.1542(3) 0.4499(2) 0.2113(6) 0.0677(7) Uani d . 1 . . C
C11 0.3410(4) 0.6723(2) 0.6002(7) 0.0828(9) Uani d D 1 . . C
H112 0.2446 0.6749 0.6923 0.099 Uiso calc R 1 . . H
H111 0.4194 0.6489 0.7215 0.099 Uiso calc R 1 . . H
C12 0.3775(5) 0.7827(3) 0.5155(9) 0.1082(13) Uani d D 1 . . C
H122 0.4706 0.7795 0.4142 0.130 Uiso calc R 1 . . H
H121 0.3976 0.8264 0.6683 0.130 Uiso calc R 1 . . H
C13 0.2537(6) 0.8362(4) 0.3571(10) 0.1355(18) Uani d D 1 . . C
H131 0.2316 0.7911 0.2050 0.163 Uiso calc R 1 . . H
C14 0.3083(11) 0.9447(5) 0.2640(17) 0.222(4) Uani d D 1 . . C
H143 0.2295 0.9776 0.1607 0.267 Uiso calc R 1 . . H
H142 0.3988 0.9349 0.1619 0.267 Uiso calc R 1 . . H
H141 0.3306 0.9897 0.4113 0.267 Uiso calc R 1 . . H
C15 0.1067(7) 0.8530(6) 0.5095(17) 0.204(4) Uani d D 1 . . C
H153 0.0307 0.8861 0.4009 0.244 Uiso calc R 1 . . H
H151 0.1263 0.8981 0.6577 0.244 Uiso calc R 1 . . H
H152 0.0704 0.7852 0.5662 0.244 Uiso calc R 1 . . H
C21 0.2184(4) 0.3287(3) -0.1431(7) 0.0823(9) Uani d D 1 . . C
H211 0.2797 0.3354 -0.2980 0.099 Uiso calc R 1 . . H
H212 0.1117 0.3333 -0.1946 0.099 Uiso calc R 1 . . H
C22 0.2493(5) 0.2215(3) -0.0267(10) 0.1145(14) Uani d D 1 . . C
H223 0.2248 0.1665 -0.1510 0.137 Uiso calc R 1 . . H
H222 0.1876 0.2138 0.1249 0.137 Uiso calc R 1 . . H
H221 0.3555 0.2157 0.0205 0.137 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0643(12) 0.0974(15) 0.0986(16) -0.0124(10) 0.0275(11) -0.0013(12)
O2 0.0601(12) 0.0913(14) 0.1009(16) -0.0127(9) 0.0233(10) -0.0026(12)
N1 0.0559(12) 0.0734(14) 0.0766(15) -0.0013(10) 0.0194(10) 0.0026(12)
N2 0.0567(13) 0.0770(15) 0.0859(17) -0.0015(10) 0.0183(11) -0.0011(12)
C1 0.0560(14) 0.0729(16) 0.0771(18) 0.0034(11) 0.0139(12) 0.0141(13)
C2 0.0534(13) 0.0737(16) 0.0764(18) 0.0043(11) 0.0155(12) 0.0136(14)
C11 0.0733(18) 0.0785(19) 0.097(2) 0.0010(14) 0.0112(16) 0.0006(17)
C12 0.104(3) 0.094(3) 0.127(3) -0.011(2) 0.027(2) -0.009(2)
C13 0.163(5) 0.101(3) 0.142(4) 0.008(3) -0.022(4) 0.014(3)
C14 0.351(13) 0.109(4) 0.208(8) -0.010(5) 0.035(8) 0.048(5)
C15 0.132(5) 0.145(5) 0.332(11) 0.029(4) -0.038(7) 0.009(6)
C21 0.0658(17) 0.091(2) 0.090(2) 0.0008(14) 0.0127(15) -0.0019(17)
C22 0.120(3) 0.089(3) 0.134(3) 0.006(2) 0.009(3) 0.004(2)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.217(3) ?
O2 C2 . 1.238(3) ?
N1 C1 . 1.361(4) ?
N1 C2 . 1.395(4) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.322(4) ?
N2 C21 . 1.447(4) ?
N2 H21 . 0.8600 ?
C1 C11 . 1.516(5) ?
C11 C12 . 1.495(5) ?
C11 H112 . 0.9700 ?
C11 H111 . 0.9700 ?
C12 C13 . 1.508(7) ?
C12 H122 . 0.9700 ?
C12 H121 . 0.9700 ?
C13 C15 . 1.522(9) ?
C13 C14 . 1.531(8) ?
C13 H131 . 0.9800 ?
C14 H143 . 0.9600 ?
C14 H142 . 0.9600 ?
C14 H141 . 0.9600 ?
C15 H153 . 0.9600 ?
C15 H151 . 0.9600 ?
C15 H152 . 0.9600 ?
C21 C22 . 1.498(5) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 H223 . 0.9600 ?
C22 H222 . 0.9600 ?
C22 H221 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 129.5(2) ?
C1 N1 H11 . . 115.2 ?
C2 N1 H11 . . 115.2 ?
C2 N2 C21 . . 122.1(2) ?
C2 N2 H21 . . 118.9 ?
C21 N2 H21 . . 118.9 ?
O1 C1 N1 . . 122.6(3) ?
O1 C1 C11 . . 122.1(3) ?
N1 C1 C11 . . 115.3(2) ?
O2 C2 N2 . . 123.5(3) ?
O2 C2 N1 . . 118.2(3) ?
N2 C2 N1 . . 118.3(2) ?
C12 C11 C1 . . 115.1(3) ?
C12 C11 H112 . . 108.5 ?
C1 C11 H112 . . 108.5 ?
C12 C11 H111 . . 108.5 ?
C1 C11 H111 . . 108.5 ?
H112 C11 H111 . . 107.5 ?
C11 C12 C13 . . 114.6(3) ?
C11 C12 H122 . . 108.6 ?
C13 C12 H122 . . 108.6 ?
C11 C12 H121 . . 108.6 ?
C13 C12 H121 . . 108.6 ?
H122 C12 H121 . . 107.6 ?
C12 C13 C15 . . 112.2(5) ?
C12 C13 C14 . . 110.0(5) ?
C15 C13 C14 . . 108.7(6) ?
C12 C13 H131 . . 108.6 ?
C15 C13 H131 . . 108.6 ?
C14 C13 H131 . . 108.6 ?
C13 C14 H143 . . 109.5 ?
C13 C14 H142 . . 109.5 ?
H143 C14 H142 . . 109.5 ?
C13 C14 H141 . . 109.5 ?
H143 C14 H141 . . 109.5 ?
H142 C14 H141 . . 109.5 ?
C13 C15 H153 . . 109.5 ?
C13 C15 H151 . . 109.5 ?
H153 C15 H151 . . 109.5 ?
C13 C15 H152 . . 109.5 ?
H153 C15 H152 . . 109.5 ?
H151 C15 H152 . . 109.5 ?
N2 C21 C22 . . 112.9(3) ?
N2 C21 H211 . . 109.0 ?
C22 C21 H211 . . 109.0 ?
N2 C21 H212 . . 109.0 ?
C22 C21 H212 . . 109.0 ?
H211 C21 H212 . . 107.8 ?
C21 C22 H223 . . 109.5 ?
C21 C22 H222 . . 109.5 ?
H223 C22 H222 . . 109.5 ?
C21 C22 H221 . . 109.5 ?
H223 C22 H221 . . 109.5 ?
H222 C22 H221 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 2.1(5) ?
C2 N1 C1 C11 . . . . -176.8(3) ?
C21 N2 C2 O2 . . . . 0.1(4) ?
C21 N2 C2 N1 . . . . 178.8(2) ?
C1 N1 C2 O2 . . . . 179.5(3) ?
C1 N1 C2 N2 . . . . 0.8(4) ?
O1 C1 C11 C12 . . . . 54.6(4) ?
N1 C1 C11 C12 . . . . -126.5(3) ?
C1 C11 C12 C13 . . . . 66.9(5) ?
C11 C12 C13 C15 . . . . 63.1(6) ?
C11 C12 C13 C14 . . . . -175.7(5) ?
C2 N2 C21 C22 . . . . -82.7(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.86 2.40 3.085(3) 137.1
N1 H11 O2 2_566 0.86 2.00 2.861(3) 177.7
data_ethyl360K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.7564(14)
_cell_length_b 12.5792(14)
_cell_length_c 5.1472(6)
_cell_angle_alpha 90.683(10)
_cell_angle_beta 90.707(6)
_cell_angle_gamma 89.216(6)
_cell_volume 566.82(13)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2770
_cell_measurement_theta_min 2.815
_cell_measurement_theta_max 27.3
_cell_measurement_temperature 360
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 1.00
_exptl_crystal_size_mid 1.00
_exptl_crystal_size_min 0.20
_exptl_crystal_density_diffrn 1.091
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.077
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being low temperature phase.
;
_diffrn_ambient_temperature 360
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 6442
_diffrn_reflns_av_R_equivalents 0.055
_diffrn_reflns_av_sigmaI/netI 0.0305
_diffrn_reflns_theta_min 2.33
_diffrn_reflns_theta_max 27.43
_diffrn_reflns_theta_full 27.43
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.923
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 2389
_reflns_number_gt 1518
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1332
_refine_ls_R_factor_gt 0.0998
_refine_ls_wR_factor_gt 0.2768
_refine_ls_wR_factor_ref 0.3155
_refine_ls_goodness_of_fit_ref 1.039
_refine_ls_restrained_S_all 1.043
_refine_ls_number_reflns 2389
_refine_ls_number_parameters 118
_refine_ls_number_restraints 5
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1605P)^2^+0.2211P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.305
_refine_diff_density_min -0.286
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 358K was used as an initial model.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.4323(3) 0.5741(2) 0.2286(6) 0.0901(8) Uani d . 1 . . O
O2 0.0268(3) 0.4099(2) 0.2428(5) 0.0870(8) Uani d . 1 . . O
N1 0.1970(3) 0.5334(2) 0.3761(6) 0.0710(8) Uani d . 1 . . N
H11 0.1304 0.5521 0.4898 0.085 Uiso calc R 1 . . H
N2 0.2524(3) 0.4167(2) 0.0336(6) 0.0747(8) Uani d . 1 . . N
H21 0.3385 0.4483 0.0205 0.090 Uiso calc R 1 . . H
C1 0.3288(4) 0.5898(3) 0.3835(7) 0.0698(9) Uani d . 1 . . C
C2 0.1541(4) 0.4501(3) 0.2124(7) 0.0712(9) Uani d . 1 . . C
C11 0.3405(5) 0.6718(3) 0.5965(8) 0.0845(10) Uani d D 1 . . C
H112 0.4188 0.6486 0.7190 0.101 Uiso calc R 1 . . H
H111 0.2443 0.6743 0.6881 0.101 Uiso calc R 1 . . H
C12 0.3769(6) 0.7824(4) 0.5126(11) 0.1170(16) Uani d D 1 . . C
H121 0.4692 0.7795 0.4104 0.140 Uiso calc R 1 . . H
H122 0.3979 0.8254 0.6662 0.140 Uiso calc R 1 . . H
C13 0.2526(7) 0.8365(4) 0.3553(13) 0.140(2) Uani d D 1 . . C
H131 0.2293 0.7922 0.2024 0.168 Uiso calc R 1 . . H
C14 0.3085(14) 0.9442(5) 0.264(2) 0.233(5) Uani d D 1 . . C
H143 0.2299 0.9782 0.1622 0.279 Uiso calc R 1 . . H
H142 0.3982 0.9340 0.1610 0.279 Uiso calc R 1 . . H
H141 0.3327 0.9881 0.4127 0.279 Uiso calc R 1 . . H
C15 0.1069(8) 0.8536(7) 0.509(2) 0.218(5) Uani d D 1 . . C
H153 0.0310 0.8877 0.4020 0.261 Uiso calc R 1 . . H
H151 0.1281 0.8977 0.6588 0.261 Uiso calc R 1 . . H
H152 0.0699 0.7862 0.5650 0.261 Uiso calc R 1 . . H
C21 0.2183(4) 0.3289(3) -0.1393(8) 0.0845(10) Uani d D 1 . . C
H211 0.2780 0.3356 -0.2956 0.101 Uiso calc R 1 . . H
H212 0.1113 0.3331 -0.1895 0.101 Uiso calc R 1 . . H
C22 0.2504(7) 0.2222(4) -0.0241(11) 0.1191(16) Uani d D 1 . . C
H223 0.2252 0.1676 -0.1486 0.143 Uiso calc R 1 . . H
H222 0.1899 0.2141 0.1285 0.143 Uiso calc R 1 . . H
H221 0.3567 0.2165 0.0220 0.143 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0673(14) 0.1010(18) 0.1031(18) -0.0140(12) 0.0296(13) -0.0023(14)
O2 0.0617(14) 0.0968(17) 0.1034(19) -0.0135(11) 0.0254(12) -0.0052(14)
N1 0.0581(14) 0.0739(16) 0.0816(17) -0.0041(11) 0.0225(12) 0.0009(13)
N2 0.0576(14) 0.0799(17) 0.0870(19) -0.0035(12) 0.0198(13) -0.0010(14)
C1 0.0573(16) 0.0748(19) 0.078(2) -0.0007(13) 0.0135(14) 0.0148(15)
C2 0.0556(16) 0.0758(19) 0.083(2) 0.0048(13) 0.0173(14) 0.0131(16)
C11 0.079(2) 0.080(2) 0.095(3) 0.0000(17) 0.0101(19) 0.0035(19)
C12 0.110(3) 0.106(3) 0.135(4) -0.014(3) 0.026(3) -0.008(3)
C13 0.162(6) 0.111(4) 0.148(5) 0.011(4) -0.020(4) 0.018(3)
C14 0.371(16) 0.107(5) 0.222(9) -0.005(6) 0.024(10) 0.049(5)
C15 0.125(6) 0.169(7) 0.357(14) 0.028(5) -0.041(8) 0.009(8)
C21 0.068(2) 0.093(2) 0.093(2) -0.0001(17) 0.0115(18) -0.004(2)
C22 0.129(4) 0.089(3) 0.139(4) 0.004(3) 0.012(3) -0.004(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.227(4) ?
O2 C2 . 1.243(4) ?
N1 C1 . 1.363(4) ?
N1 C2 . 1.390(5) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.328(4) ?
N2 C21 . 1.443(5) ?
N2 H21 . 0.8600 ?
C1 C11 . 1.499(5) ?
C11 C12 . 1.502(6) ?
C11 H112 . 0.9700 ?
C11 H111 . 0.9700 ?
C12 C13 . 1.508(8) ?
C12 H121 . 0.9700 ?
C12 H122 . 0.9700 ?
C13 C15 . 1.522(11) ?
C13 C14 . 1.527(10) ?
C13 H131 . 0.9800 ?
C14 H143 . 0.9600 ?
C14 H142 . 0.9600 ?
C14 H141 . 0.9600 ?
C15 H153 . 0.9600 ?
C15 H151 . 0.9600 ?
C15 H152 . 0.9600 ?
C21 C22 . 1.495(6) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 H223 . 0.9600 ?
C22 H222 . 0.9600 ?
C22 H221 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 129.7(3) ?
C1 N1 H11 . . 115.2 ?
C2 N1 H11 . . 115.2 ?
C2 N2 C21 . . 121.6(3) ?
C2 N2 H21 . . 119.2 ?
C21 N2 H21 . . 119.2 ?
O1 C1 N1 . . 122.5(3) ?
O1 C1 C11 . . 121.9(3) ?
N1 C1 C11 . . 115.6(3) ?
O2 C2 N2 . . 123.4(3) ?
O2 C2 N1 . . 118.4(3) ?
N2 C2 N1 . . 118.2(3) ?
C1 C11 C12 . . 115.9(3) ?
C1 C11 H112 . . 108.3 ?
C12 C11 H112 . . 108.3 ?
C1 C11 H111 . . 108.3 ?
C12 C11 H111 . . 108.3 ?
H112 C11 H111 . . 107.4 ?
C11 C12 C13 . . 114.7(4) ?
C11 C12 H121 . . 108.6 ?
C13 C12 H121 . . 108.6 ?
C11 C12 H122 . . 108.6 ?
C13 C12 H122 . . 108.6 ?
H121 C12 H122 . . 107.6 ?
C12 C13 C15 . . 112.3(6) ?
C12 C13 C14 . . 109.5(6) ?
C15 C13 C14 . . 108.9(7) ?
C12 C13 H131 . . 108.7 ?
C15 C13 H131 . . 108.7 ?
C14 C13 H131 . . 108.7 ?
C13 C14 H143 . . 109.5 ?
C13 C14 H142 . . 109.5 ?
H143 C14 H142 . . 109.5 ?
C13 C14 H141 . . 109.5 ?
H143 C14 H141 . . 109.5 ?
H142 C14 H141 . . 109.5 ?
C13 C15 H153 . . 109.5 ?
C13 C15 H151 . . 109.5 ?
H153 C15 H151 . . 109.5 ?
C13 C15 H152 . . 109.5 ?
H153 C15 H152 . . 109.5 ?
H151 C15 H152 . . 109.5 ?
N2 C21 C22 . . 113.8(4) ?
N2 C21 H211 . . 108.8 ?
C22 C21 H211 . . 108.8 ?
N2 C21 H212 . . 108.8 ?
C22 C21 H212 . . 108.8 ?
H211 C21 H212 . . 107.7 ?
C21 C22 H223 . . 109.5 ?
C21 C22 H222 . . 109.5 ?
H223 C22 H222 . . 109.5 ?
C21 C22 H221 . . 109.5 ?
H223 C22 H221 . . 109.5 ?
H222 C22 H221 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 2.1(6) ?
C2 N1 C1 C11 . . . . -177.0(3) ?
C21 N2 C2 O2 . . . . -0.7(5) ?
C21 N2 C2 N1 . . . . 178.3(3) ?
C1 N1 C2 O2 . . . . 179.6(3) ?
C1 N1 C2 N2 . . . . 0.5(5) ?
O1 C1 C11 C12 . . . . 54.4(5) ?
N1 C1 C11 C12 . . . . -126.5(4) ?
C1 C11 C12 C13 . . . . 67.5(6) ?
C11 C12 C13 C15 . . . . 63.5(7) ?
C11 C12 C13 C14 . . . . -175.5(6) ?
C2 N2 C21 C22 . . . . -82.8(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.86 2.41 3.092(4) 137.0
N1 H11 O2 2_566 0.86 2.01 2.867(3) 177.9
data_ethyl362K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.6700(10)
_cell_length_b 12.5515(9)
_cell_length_c 5.1490(5)
_cell_angle_alpha 90.036(7)
_cell_angle_beta 91.078(4)
_cell_angle_gamma 88.834(4)
_cell_volume 560.11(9)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2412
_cell_measurement_theta_min 2.83
_cell_measurement_theta_max 27.425
_cell_measurement_temperature 362
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 1.00
_exptl_crystal_size_mid 1.00
_exptl_crystal_size_min 0.20
_exptl_crystal_density_diffrn 1.104
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.078
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being low temperature phase.
;
_diffrn_ambient_temperature 362
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 6484
_diffrn_reflns_av_R_equivalents 0.032
_diffrn_reflns_av_sigmaI/netI 0.0197
_diffrn_reflns_theta_min 2.35
_diffrn_reflns_theta_max 27.47
_diffrn_reflns_theta_full 27.47
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.920
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 2361
_reflns_number_gt 1478
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1277
_refine_ls_R_factor_gt 0.0938
_refine_ls_wR_factor_gt 0.2883
_refine_ls_wR_factor_ref 0.3316
_refine_ls_goodness_of_fit_ref 1.056
_refine_ls_restrained_S_all 1.064
_refine_ls_number_reflns 2361
_refine_ls_number_parameters 118
_refine_ls_number_restraints 5
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1819P)^2^+0.1580P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.367
_refine_diff_density_min -0.341
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 360K was used as an initial model.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.4317(3) 0.5740(2) 0.2258(5) 0.0949(9) Uani d . 1 . . O
O2 0.0275(3) 0.4100(2) 0.2453(5) 0.0914(9) Uani d . 1 . . O
N1 0.1969(3) 0.5334(2) 0.3743(6) 0.0748(8) Uani d . 1 . . N
H11 0.1295 0.5524 0.4868 0.090 Uiso calc R 1 . . H
N2 0.2531(3) 0.4165(2) 0.0370(6) 0.0797(9) Uani d . 1 . . N
H21 0.3405 0.4471 0.0254 0.096 Uiso calc R 1 . . H
C1 0.3285(3) 0.5898(3) 0.3805(7) 0.0746(9) Uani d . 1 . . C
C2 0.1545(4) 0.4502(3) 0.2152(7) 0.0743(9) Uani d . 1 . . C
C11 0.3404(5) 0.6710(3) 0.5935(8) 0.0920(11) Uani d D 1 . . C
H112 0.4198 0.6471 0.7166 0.110 Uiso calc R 1 . . H
H111 0.2434 0.6736 0.6845 0.110 Uiso calc R 1 . . H
C12 0.3768(6) 0.7819(4) 0.5084(11) 0.1242(17) Uani d D 1 . . C
H121 0.3985 0.8246 0.6615 0.149 Uiso calc R 1 . . H
H122 0.4697 0.7789 0.4064 0.149 Uiso calc R 1 . . H
C13 0.2523(8) 0.8363(4) 0.3527(13) 0.152(2) Uani d D 1 . . C
H131 0.2281 0.7923 0.2006 0.183 Uiso calc R 1 . . H
C14 0.3107(14) 0.9435(6) 0.260(2) 0.251(6) Uani d D 1 . . C
H143 0.2318 0.9787 0.1563 0.301 Uiso calc R 1 . . H
H142 0.4010 0.9322 0.1577 0.301 Uiso calc R 1 . . H
H141 0.3358 0.9870 0.4075 0.301 Uiso calc R 1 . . H
C15 0.1059(8) 0.8539(7) 0.507(2) 0.227(5) Uani d D 1 . . C
H153 0.0287 0.8887 0.3991 0.273 Uiso calc R 1 . . H
H151 0.1280 0.8976 0.6555 0.273 Uiso calc R 1 . . H
H152 0.0686 0.7864 0.5635 0.273 Uiso calc R 1 . . H
C21 0.2176(4) 0.3298(3) -0.1379(8) 0.0913(11) Uani d D 1 . . C
H211 0.2779 0.3365 -0.2936 0.110 Uiso calc R 1 . . H
H212 0.1094 0.3346 -0.1887 0.110 Uiso calc R 1 . . H
C22 0.2508(6) 0.2234(4) -0.0178(11) 0.1232(16) Uani d D 1 . . C
H223 0.2254 0.1684 -0.1399 0.148 Uiso calc R 1 . . H
H222 0.1900 0.2159 0.1348 0.148 Uiso calc R 1 . . H
H221 0.3583 0.2176 0.0291 0.148 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0658(13) 0.1088(19) 0.1116(19) -0.0130(12) 0.0314(13) -0.0022(14)
O2 0.0629(13) 0.0996(17) 0.1131(19) -0.0112(11) 0.0291(12) -0.0031(14)
N1 0.0582(14) 0.0805(17) 0.0866(17) -0.0030(11) 0.0229(12) 0.0022(13)
N2 0.0590(14) 0.0865(18) 0.0943(19) 0.0009(12) 0.0211(13) 0.0013(15)
C1 0.0584(15) 0.0772(19) 0.089(2) 0.0043(13) 0.0159(14) 0.0167(16)
C2 0.0570(15) 0.0818(19) 0.085(2) 0.0020(13) 0.0165(14) 0.0119(16)
C11 0.080(2) 0.089(2) 0.107(3) -0.0002(18) 0.0159(19) 0.000(2)
C12 0.117(4) 0.109(3) 0.148(4) -0.010(3) 0.034(3) -0.007(3)
C13 0.177(6) 0.112(4) 0.166(6) 0.012(4) -0.020(5) 0.023(4)
C14 0.389(17) 0.115(5) 0.250(11) -0.002(7) 0.047(11) 0.062(6)
C15 0.129(6) 0.163(7) 0.387(15) 0.039(5) -0.026(8) 0.019(8)
C21 0.072(2) 0.100(3) 0.102(3) 0.0020(18) 0.0164(18) -0.004(2)
C22 0.129(4) 0.096(3) 0.144(4) 0.005(3) 0.010(3) 0.003(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.222(4) ?
O2 C2 . 1.232(4) ?
N1 C1 . 1.355(4) ?
N1 C2 . 1.378(5) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.329(4) ?
N2 C21 . 1.447(5) ?
N2 H21 . 0.8600 ?
C1 C11 . 1.500(5) ?
C11 C12 . 1.501(6) ?
C11 H112 . 0.9700 ?
C11 H111 . 0.9700 ?
C12 C13 . 1.487(8) ?
C12 H121 . 0.9700 ?
C12 H122 . 0.9700 ?
C13 C15 . 1.522(11) ?
C13 C14 . 1.527(11) ?
C13 H131 . 0.9800 ?
C14 H143 . 0.9600 ?
C14 H142 . 0.9600 ?
C14 H141 . 0.9600 ?
C15 H153 . 0.9600 ?
C15 H151 . 0.9600 ?
C15 H152 . 0.9600 ?
C21 C22 . 1.492(6) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 H223 . 0.9600 ?
C22 H222 . 0.9600 ?
C22 H221 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 129.8(3) ?
C1 N1 H11 . . 115.1 ?
C2 N1 H11 . . 115.1 ?
C2 N2 C21 . . 121.9(3) ?
C2 N2 H21 . . 119.0 ?
C21 N2 H21 . . 119.0 ?
O1 C1 N1 . . 122.1(4) ?
O1 C1 C11 . . 122.4(3) ?
N1 C1 C11 . . 115.5(3) ?
O2 C2 N2 . . 122.9(4) ?
O2 C2 N1 . . 118.7(3) ?
N2 C2 N1 . . 118.4(3) ?
C1 C11 C12 . . 115.6(4) ?
C1 C11 H112 . . 108.4 ?
C12 C11 H112 . . 108.4 ?
C1 C11 H111 . . 108.4 ?
C12 C11 H111 . . 108.4 ?
H112 C11 H111 . . 107.4 ?
C13 C12 C11 . . 114.7(4) ?
C13 C12 H121 . . 108.6 ?
C11 C12 H121 . . 108.6 ?
C13 C12 H122 . . 108.6 ?
C11 C12 H122 . . 108.6 ?
H121 C12 H122 . . 107.6 ?
C12 C13 C15 . . 112.3(6) ?
C12 C13 C14 . . 108.8(7) ?
C15 C13 C14 . . 109.5(7) ?
C12 C13 H131 . . 108.7 ?
C15 C13 H131 . . 108.7 ?
C14 C13 H131 . . 108.7 ?
C13 C14 H143 . . 109.5 ?
C13 C14 H142 . . 109.5 ?
H143 C14 H142 . . 109.5 ?
C13 C14 H141 . . 109.5 ?
H143 C14 H141 . . 109.5 ?
H142 C14 H141 . . 109.5 ?
C13 C15 H153 . . 109.5 ?
C13 C15 H151 . . 109.5 ?
H153 C15 H151 . . 109.5 ?
C13 C15 H152 . . 109.5 ?
H153 C15 H152 . . 109.5 ?
H151 C15 H152 . . 109.5 ?
N2 C21 C22 . . 112.2(4) ?
N2 C21 H211 . . 109.2 ?
C22 C21 H211 . . 109.2 ?
N2 C21 H212 . . 109.2 ?
C22 C21 H212 . . 109.2 ?
H211 C21 H212 . . 107.9 ?
C21 C22 H223 . . 109.5 ?
C21 C22 H222 . . 109.5 ?
H223 C22 H222 . . 109.5 ?
C21 C22 H221 . . 109.5 ?
H223 C22 H221 . . 109.5 ?
H222 C22 H221 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 2.6(5) ?
C2 N1 C1 C11 . . . . -175.9(3) ?
C21 N2 C2 O2 . . . . 0.6(5) ?
C21 N2 C2 N1 . . . . -179.9(3) ?
C1 N1 C2 O2 . . . . 179.7(3) ?
C1 N1 C2 N2 . . . . 0.2(5) ?
O1 C1 C11 C12 . . . . 54.3(5) ?
N1 C1 C11 C12 . . . . -127.2(4) ?
C1 C11 C12 C13 . . . . 67.6(6) ?
C11 C12 C13 C15 . . . . 63.7(8) ?
C11 C12 C13 C14 . . . . -175.0(6) ?
C2 N2 C21 C22 . . . . -83.2(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.86 2.39 3.077(4) 137.0
N1 H11 O2 2_566 0.86 2.01 2.866(3) 177.5
data_ethyl364K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.7109(12)
_cell_length_b 12.6454(10)
_cell_length_c 5.1787(6)
_cell_angle_alpha 90.134(7)
_cell_angle_beta 90.557(4)
_cell_angle_gamma 88.953(4)
_cell_volume 570.32(11)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2832
_cell_measurement_theta_min 2.815
_cell_measurement_theta_max 27.465
_cell_measurement_temperature 364
_exptl_crystal_description 'triclinic'
_exptl_crystal_colour 'P -1'
_exptl_crystal_size_max 1.00
_exptl_crystal_size_mid 1.00
_exptl_crystal_size_min 0.20
_exptl_crystal_density_diffrn 1.085
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.077
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being low temperature phase.
;
_diffrn_ambient_temperature 364
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 7726
_diffrn_reflns_av_R_equivalents 0.028
_diffrn_reflns_av_sigmaI/netI 0.0248
_diffrn_reflns_theta_min 2.34
_diffrn_reflns_theta_max 27.48
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 2503
_reflns_number_gt 1474
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1327
_refine_ls_R_factor_gt 0.0914
_refine_ls_wR_factor_gt 0.2586
_refine_ls_wR_factor_ref 0.3005
_refine_ls_goodness_of_fit_ref 1.054
_refine_ls_restrained_S_all 1.061
_refine_ls_number_reflns 2503
_refine_ls_number_parameters 118
_refine_ls_number_restraints 5
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1424P)^2^+0.1845P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.327
_refine_diff_density_min -0.335
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 362K was used as an initial model.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.4319(3) 0.5736(2) 0.2249(5) 0.0986(9) Uani d . 1 . . O
O2 0.0272(2) 0.4103(2) 0.2467(5) 0.0946(8) Uani d . 1 . . O
N1 0.1969(3) 0.5332(2) 0.3748(5) 0.0782(8) Uani d . 1 . . N
H11 0.1299 0.5519 0.4879 0.094 Uiso calc R 1 . . H
N2 0.2527(3) 0.4164(2) 0.0378(5) 0.0816(8) Uani d . 1 . . N
H21 0.3394 0.4473 0.0241 0.098 Uiso calc R 1 . . H
C1 0.3282(3) 0.5898(3) 0.3795(7) 0.0773(9) Uani d . 1 . . C
C2 0.1543(3) 0.4501(3) 0.2157(7) 0.0770(9) Uani d . 1 . . C
C11 0.3393(4) 0.6712(3) 0.5878(8) 0.0947(11) Uani d D 1 . . C
H112 0.4174 0.6478 0.7108 0.114 Uiso calc R 1 . . H
H111 0.2423 0.6741 0.6781 0.114 Uiso calc R 1 . . H
C12 0.3765(6) 0.7815(4) 0.5040(12) 0.1366(19) Uani d D 1 . . C
H121 0.3983 0.8236 0.6563 0.164 Uiso calc R 1 . . H
H122 0.4690 0.7784 0.4012 0.164 Uiso calc R 1 . . H
C13 0.2526(8) 0.8360(5) 0.3510(13) 0.164(2) Uani d D 1 . . C
H131 0.2278 0.7921 0.2005 0.197 Uiso calc R 1 . . H
C14 0.3093(14) 0.9432(6) 0.256(2) 0.268(6) Uani d D 1 . . C
H143 0.2300 0.9774 0.1545 0.321 Uiso calc R 1 . . H
H142 0.3988 0.9324 0.1516 0.321 Uiso calc R 1 . . H
H141 0.3345 0.9869 0.4013 0.321 Uiso calc R 1 . . H
C15 0.1066(9) 0.8549(7) 0.506(2) 0.254(5) Uani d D 1 . . C
H153 0.0311 0.8906 0.3998 0.305 Uiso calc R 1 . . H
H151 0.1294 0.8977 0.6542 0.305 Uiso calc R 1 . . H
H152 0.0674 0.7882 0.5612 0.305 Uiso calc R 1 . . H
C21 0.2184(4) 0.3296(3) -0.1327(8) 0.0941(11) Uani d D 1 . . C
H211 0.2785 0.3363 -0.2883 0.113 Uiso calc R 1 . . H
H212 0.1108 0.3342 -0.1821 0.113 Uiso calc R 1 . . H
C22 0.2509(6) 0.2236(4) -0.0161(11) 0.1308(17) Uani d D 1 . . C
H223 0.2256 0.1694 -0.1385 0.157 Uiso calc R 1 . . H
H222 0.1902 0.2157 0.1362 0.157 Uiso calc R 1 . . H
H221 0.3579 0.2177 0.0291 0.157 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0688(13) 0.1134(18) 0.1148(19) -0.0135(12) 0.0318(13) -0.0016(14)
O2 0.0659(13) 0.1035(17) 0.1153(19) -0.0122(11) 0.0291(12) -0.0042(14)
N1 0.0613(14) 0.0823(16) 0.0916(18) -0.0019(11) 0.0244(12) 0.0028(14)
N2 0.0597(14) 0.0895(18) 0.0961(19) -0.0029(12) 0.0200(13) 0.0002(15)
C1 0.0602(16) 0.0814(19) 0.090(2) 0.0025(13) 0.0160(14) 0.0168(16)
C2 0.0569(15) 0.086(2) 0.088(2) 0.0057(14) 0.0179(14) 0.0129(17)
C11 0.083(2) 0.087(2) 0.115(3) -0.0018(17) 0.0169(19) 0.002(2)
C12 0.124(4) 0.118(4) 0.169(5) -0.011(3) 0.040(3) -0.007(3)
C13 0.175(6) 0.133(4) 0.183(6) 0.019(4) -0.013(5) 0.039(4)
C14 0.416(18) 0.120(5) 0.268(11) -0.021(7) 0.024(11) 0.065(6)
C15 0.138(6) 0.191(8) 0.432(16) 0.044(5) -0.026(8) 0.027(9)
C21 0.073(2) 0.103(3) 0.106(3) 0.0018(17) 0.0162(18) -0.001(2)
C22 0.135(4) 0.100(3) 0.157(4) 0.007(3) 0.013(3) 0.001(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.226(4) ?
O2 C2 . 1.236(4) ?
N1 C1 . 1.360(4) ?
N1 C2 . 1.388(5) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.329(4) ?
N2 C21 . 1.440(5) ?
N2 H21 . 0.8600 ?
C1 C11 . 1.494(5) ?
C11 C12 . 1.503(6) ?
C11 H112 . 0.9700 ?
C11 H111 . 0.9700 ?
C12 C13 . 1.492(8) ?
C12 H121 . 0.9700 ?
C12 H122 . 0.9700 ?
C13 C15 . 1.525(11) ?
C13 C14 . 1.536(10) ?
C13 H131 . 0.9800 ?
C14 H143 . 0.9600 ?
C14 H142 . 0.9600 ?
C14 H141 . 0.9600 ?
C15 H153 . 0.9600 ?
C15 H151 . 0.9600 ?
C15 H152 . 0.9600 ?
C21 C22 . 1.493(6) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 H223 . 0.9600 ?
C22 H222 . 0.9600 ?
C22 H221 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 129.9(3) ?
C1 N1 H11 . . 115.0 ?
C2 N1 H11 . . 115.0 ?
C2 N2 C21 . . 121.9(3) ?
C2 N2 H21 . . 119.1 ?
C21 N2 H21 . . 119.1 ?
O1 C1 N1 . . 122.0(3) ?
O1 C1 C11 . . 122.3(3) ?
N1 C1 C11 . . 115.7(3) ?
O2 C2 N2 . . 123.0(3) ?
O2 C2 N1 . . 118.7(3) ?
N2 C2 N1 . . 118.3(3) ?
C1 C11 C12 . . 116.5(4) ?
C1 C11 H112 . . 108.2 ?
C12 C11 H112 . . 108.2 ?
C1 C11 H111 . . 108.2 ?
C12 C11 H111 . . 108.2 ?
H112 C11 H111 . . 107.3 ?
C13 C12 C11 . . 114.6(4) ?
C13 C12 H121 . . 108.6 ?
C11 C12 H121 . . 108.6 ?
C13 C12 H122 . . 108.6 ?
C11 C12 H122 . . 108.6 ?
H121 C12 H122 . . 107.6 ?
C12 C13 C15 . . 112.7(6) ?
C12 C13 C14 . . 109.7(6) ?
C15 C13 C14 . . 108.4(7) ?
C12 C13 H131 . . 108.6 ?
C15 C13 H131 . . 108.6 ?
C14 C13 H131 . . 108.6 ?
C13 C14 H143 . . 109.5 ?
C13 C14 H142 . . 109.5 ?
H143 C14 H142 . . 109.5 ?
C13 C14 H141 . . 109.5 ?
H143 C14 H141 . . 109.5 ?
H142 C14 H141 . . 109.5 ?
C13 C15 H153 . . 109.5 ?
C13 C15 H151 . . 109.5 ?
H153 C15 H151 . . 109.5 ?
C13 C15 H152 . . 109.5 ?
H153 C15 H152 . . 109.5 ?
H151 C15 H152 . . 109.5 ?
N2 C21 C22 . . 113.5(4) ?
N2 C21 H211 . . 108.9 ?
C22 C21 H211 . . 108.9 ?
N2 C21 H212 . . 108.9 ?
C22 C21 H212 . . 108.9 ?
H211 C21 H212 . . 107.7 ?
C21 C22 H223 . . 109.5 ?
C21 C22 H222 . . 109.5 ?
H223 C22 H222 . . 109.5 ?
C21 C22 H221 . . 109.5 ?
H223 C22 H221 . . 109.5 ?
H222 C22 H221 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 1.9(5) ?
C2 N1 C1 C11 . . . . -176.9(3) ?
C21 N2 C2 O2 . . . . -0.4(5) ?
C21 N2 C2 N1 . . . . 179.1(3) ?
C1 N1 C2 O2 . . . . -179.9(3) ?
C1 N1 C2 N2 . . . . 0.6(5) ?
O1 C1 C11 C12 . . . . 53.8(5) ?
N1 C1 C11 C12 . . . . -127.3(4) ?
C1 C11 C12 C13 . . . . 68.3(6) ?
C11 C12 C13 C15 . . . . 64.2(8) ?
C11 C12 C13 C14 . . . . -174.8(6) ?
C2 N2 C21 C22 . . . . -83.0(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.86 2.39 3.083(3) 137.4
N1 H11 O2 2_566 0.86 2.00 2.860(3) 177.9
data_ethyl366K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.7157(12)
_cell_length_b 12.6307(7)
_cell_length_c 5.1642(7)
_cell_angle_alpha 89.780(10)
_cell_angle_beta 90.522(6)
_cell_angle_gamma 88.757(5)
_cell_volume 568.34(11)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2373
_cell_measurement_theta_min 2.81
_cell_measurement_theta_max 27.39
_cell_measurement_temperature 366
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 1.00
_exptl_crystal_size_mid 1.00
_exptl_crystal_size_min 0.20
_exptl_crystal_density_diffrn 1.088
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.077
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being low temperature phase.
;
_diffrn_ambient_temperature 366
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 6593
_diffrn_reflns_av_R_equivalents 0.033
_diffrn_reflns_av_sigmaI/netI 0.0237
_diffrn_reflns_theta_min 2.34
_diffrn_reflns_theta_max 27.47
_diffrn_reflns_theta_full 27.47
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measured_fraction_theta_full 0.912
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 2383
_reflns_number_gt 1377
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1455
_refine_ls_R_factor_gt 0.1004
_refine_ls_wR_factor_gt 0.2914
_refine_ls_wR_factor_ref 0.3424
_refine_ls_goodness_of_fit_ref 1.051
_refine_ls_restrained_S_all 1.058
_refine_ls_number_reflns 2383
_refine_ls_number_parameters 118
_refine_ls_number_restraints 5
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1637P)^2^+0.2294P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.319
_refine_diff_density_min -0.351
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 364K was used as an initial model.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.4312(3) 0.5736(2) 0.2226(6) 0.1031(10) Uani d . 1 . . O
O2 0.0275(3) 0.4105(2) 0.2482(6) 0.0982(10) Uani d . 1 . . O
N1 0.1970(3) 0.5329(2) 0.3746(6) 0.0805(9) Uani d . 1 . . N
H11 0.1307 0.5513 0.4892 0.097 Uiso calc R 1 . . H
N2 0.2532(3) 0.4167(2) 0.0410(7) 0.0849(10) Uani d . 1 . . N
H21 0.3401 0.4471 0.0282 0.102 Uiso calc R 1 . . H
C1 0.3274(4) 0.5894(3) 0.3763(8) 0.0797(10) Uani d . 1 . . C
C2 0.1540(4) 0.4501(3) 0.2168(8) 0.0822(11) Uani d . 1 . . C
C11 0.3390(5) 0.6702(3) 0.5821(10) 0.1012(13) Uani d D 1 . . C
H111 0.4173 0.6465 0.7051 0.121 Uiso calc R 1 . . H
H112 0.2423 0.6733 0.6734 0.121 Uiso calc R 1 . . H
C12 0.3760(7) 0.7804(4) 0.4976(15) 0.154(3) Uani d D 1 . . C
H121 0.3992 0.8220 0.6500 0.185 Uiso calc R 1 . . H
H122 0.4675 0.7773 0.3922 0.185 Uiso calc R 1 . . H
C13 0.2512(9) 0.8357(6) 0.3477(17) 0.176(3) Uani d D 1 . . C
H131 0.2261 0.7926 0.1964 0.212 Uiso calc R 1 . . H
C14 0.3096(17) 0.9424(7) 0.252(3) 0.299(8) Uani d D 1 . . C
H143 0.2313 0.9775 0.1498 0.358 Uiso calc R 1 . . H
H142 0.3994 0.9309 0.1489 0.358 Uiso calc R 1 . . H
H141 0.3349 0.9857 0.3983 0.358 Uiso calc R 1 . . H
C15 0.1057(10) 0.8541(9) 0.503(3) 0.271(6) Uani d D 1 . . C
H153 0.0293 0.8889 0.3954 0.325 Uiso calc R 1 . . H
H151 0.1278 0.8977 0.6496 0.325 Uiso calc R 1 . . H
H152 0.0680 0.7874 0.5609 0.325 Uiso calc R 1 . . H
C21 0.2180(5) 0.3301(4) -0.1300(9) 0.1003(13) Uani d D 1 . . C
H211 0.2777 0.3365 -0.2867 0.120 Uiso calc R 1 . . H
H212 0.1102 0.3348 -0.1785 0.120 Uiso calc R 1 . . H
C22 0.2515(7) 0.2241(4) -0.0079(13) 0.135(2) Uani d D 1 . . C
H223 0.2260 0.1692 -0.1277 0.162 Uiso calc R 1 . . H
H222 0.1915 0.2169 0.1459 0.162 Uiso calc R 1 . . H
H221 0.3586 0.2183 0.0363 0.162 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0734(16) 0.117(2) 0.120(2) -0.0134(14) 0.0366(15) -0.0011(17)
O2 0.0680(15) 0.107(2) 0.121(2) -0.0110(13) 0.0309(14) -0.0051(16)
N1 0.0627(16) 0.0837(19) 0.096(2) -0.0030(13) 0.0232(14) -0.0002(16)
N2 0.0622(16) 0.092(2) 0.101(2) -0.0023(14) 0.0219(15) -0.0020(17)
C1 0.0637(18) 0.082(2) 0.093(2) 0.0011(15) 0.0165(17) 0.0163(18)
C2 0.0587(17) 0.091(2) 0.097(3) 0.0060(16) 0.0196(17) 0.016(2)
C11 0.089(3) 0.089(3) 0.126(4) -0.001(2) 0.020(2) 0.004(2)
C12 0.145(5) 0.119(4) 0.201(7) -0.007(4) 0.053(5) -0.008(4)
C13 0.181(7) 0.140(5) 0.207(8) 0.017(5) -0.013(6) 0.043(5)
C14 0.47(2) 0.117(6) 0.308(15) -0.035(9) 0.053(15) 0.050(7)
C15 0.140(8) 0.223(10) 0.45(2) 0.056(7) -0.018(10) 0.008(11)
C21 0.077(2) 0.113(3) 0.112(3) 0.000(2) 0.018(2) -0.004(3)
C22 0.138(5) 0.102(3) 0.166(5) 0.004(3) 0.013(4) 0.004(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.222(4) ?
O2 C2 . 1.233(4) ?
N1 C1 . 1.355(5) ?
N1 C2 . 1.385(5) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.323(5) ?
N2 C21 . 1.445(5) ?
N2 H21 . 0.8600 ?
C1 C11 . 1.481(6) ?
C11 C12 . 1.499(7) ?
C11 H111 . 0.9700 ?
C11 H112 . 0.9700 ?
C12 C13 . 1.490(10) ?
C12 H121 . 0.9700 ?
C12 H122 . 0.9700 ?
C13 C15 . 1.520(13) ?
C13 C14 . 1.532(13) ?
C13 H131 . 0.9800 ?
C14 H143 . 0.9600 ?
C14 H142 . 0.9600 ?
C14 H141 . 0.9600 ?
C15 H153 . 0.9600 ?
C15 H151 . 0.9600 ?
C15 H152 . 0.9600 ?
C21 C22 . 1.500(7) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 H223 . 0.9600 ?
C22 H222 . 0.9600 ?
C22 H221 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 129.9(3) ?
C1 N1 H11 . . 115.0 ?
C2 N1 H11 . . 115.0 ?
C2 N2 C21 . . 121.2(3) ?
C2 N2 H21 . . 119.4 ?
C21 N2 H21 . . 119.4 ?
O1 C1 N1 . . 122.6(4) ?
O1 C1 C11 . . 121.6(4) ?
N1 C1 C11 . . 115.7(3) ?
O2 C2 N2 . . 123.4(4) ?
O2 C2 N1 . . 118.9(3) ?
N2 C2 N1 . . 117.6(3) ?
C1 C11 C12 . . 116.8(5) ?
C1 C11 H111 . . 108.1 ?
C12 C11 H111 . . 108.1 ?
C1 C11 H112 . . 108.1 ?
C12 C11 H112 . . 108.1 ?
H111 C11 H112 . . 107.3 ?
C13 C12 C11 . . 114.5(5) ?
C13 C12 H121 . . 108.6 ?
C11 C12 H121 . . 108.6 ?
C13 C12 H122 . . 108.6 ?
C11 C12 H122 . . 108.6 ?
H121 C12 H122 . . 107.6 ?
C12 C13 C15 . . 113.4(7) ?
C12 C13 C14 . . 108.9(8) ?
C15 C13 C14 . . 109.2(9) ?
C12 C13 H131 . . 108.4 ?
C15 C13 H131 . . 108.4 ?
C14 C13 H131 . . 108.4 ?
C13 C14 H143 . . 109.5 ?
C13 C14 H142 . . 109.5 ?
H143 C14 H142 . . 109.5 ?
C13 C14 H141 . . 109.5 ?
H143 C14 H141 . . 109.5 ?
H142 C14 H141 . . 109.5 ?
C13 C15 H153 . . 109.5 ?
C13 C15 H151 . . 109.5 ?
H153 C15 H151 . . 109.5 ?
C13 C15 H152 . . 109.5 ?
H153 C15 H152 . . 109.5 ?
H151 C15 H152 . . 109.5 ?
N2 C21 C22 . . 112.4(4) ?
N2 C21 H211 . . 109.1 ?
C22 C21 H211 . . 109.1 ?
N2 C21 H212 . . 109.1 ?
C22 C21 H212 . . 109.1 ?
H211 C21 H212 . . 107.9 ?
C21 C22 H223 . . 109.5 ?
C21 C22 H222 . . 109.5 ?
H223 C22 H222 . . 109.5 ?
C21 C22 H221 . . 109.5 ?
H223 C22 H221 . . 109.5 ?
H222 C22 H221 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 1.1(6) ?
C2 N1 C1 C11 . . . . -177.2(4) ?
C21 N2 C2 O2 . . . . 0.4(6) ?
C21 N2 C2 N1 . . . . 179.5(3) ?
C1 N1 C2 O2 . . . . -179.3(3) ?
C1 N1 C2 N2 . . . . 1.6(6) ?
O1 C1 C11 C12 . . . . 53.9(6) ?
N1 C1 C11 C12 . . . . -127.7(4) ?
C1 C11 C12 C13 . . . . 69.0(7) ?
C11 C12 C13 C15 . . . . 63.5(10) ?
C11 C12 C13 C14 . . . . -174.6(7) ?
C2 N2 C21 C22 . . . . -83.6(5) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.86 2.40 3.085(4) 137.3
N1 H11 O2 2_566 0.86 2.00 2.855(4) 177.9
data_ethyl368K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.6912(5)
_cell_length_b 12.7757(6)
_cell_length_c 5.15870(10)
_cell_angle_alpha 88.386(2)
_cell_angle_beta 91.168(6)
_cell_angle_gamma 88.4630(19)
_cell_volume 572.24(4)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2775
_cell_measurement_theta_min 2.8
_cell_measurement_theta_max 27.465
_cell_measurement_temperature 368
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 1.00
_exptl_crystal_size_mid 1.00
_exptl_crystal_size_min 0.20
_exptl_crystal_density_diffrn 1.081
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.077
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being high temperature phase.
;
_diffrn_ambient_temperature 368
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 7417
_diffrn_reflns_av_R_equivalents 0.021
_diffrn_reflns_av_sigmaI/netI 0.0210
_diffrn_reflns_theta_min 2.34
_diffrn_reflns_theta_max 27.47
_diffrn_reflns_theta_full 27.47
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measured_fraction_theta_full 0.868
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 2283
_reflns_number_gt 1212
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1569
_refine_ls_R_factor_gt 0.0989
_refine_ls_wR_factor_gt 0.2561
_refine_ls_wR_factor_ref 0.3081
_refine_ls_goodness_of_fit_ref 1.067
_refine_ls_restrained_S_all 1.069
_refine_ls_number_reflns 2283
_refine_ls_number_parameters 131
_refine_ls_number_restraints 17
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1263P)^2^+0.2311P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.241
_refine_diff_density_min -0.276
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 366K was used as an initial model.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.4310(3) 0.5728(2) 0.2201(6) 0.1095(11) Uani d . 1 A . O
O2 0.0279(3) 0.4107(2) 0.2539(6) 0.1050(10) Uani d . 1 A . O
N1 0.1966(3) 0.5326(2) 0.3729(6) 0.0858(10) Uani d . 1 A . N
H11 0.1302 0.5513 0.4852 0.103 Uiso calc R 1 . . H
N2 0.2532(3) 0.4167(3) 0.0458(7) 0.0928(10) Uani d D 1 A . N
H21 0.3403 0.4466 0.0329 0.111 Uiso calc R 1 . . H
C1 0.3272(4) 0.5884(3) 0.3710(7) 0.0866(11) Uani d D 1 . . C
C2 0.1542(4) 0.4496(3) 0.2198(8) 0.0861(11) Uani d . 1 . . C
C11A 0.3370(5) 0.6696(3) 0.5749(9) 0.1098(14) Uani d PD 0.874(6) A 1 C
H111 0.4138 0.6454 0.7035 0.132 Uiso calc PR 0.874(6) A 1 H
H112 0.2388 0.6729 0.6609 0.132 Uiso calc PR 0.874(6) A 1 H
C12A 0.3760(7) 0.7806(4) 0.4893(15) 0.158(3) Uani d PD 0.874(6) A 1 C
H121 0.4671 0.7782 0.3839 0.190 Uiso calc PR 0.874(6) A 1 H
H122 0.3993 0.8208 0.6412 0.190 Uiso calc PR 0.874(6) A 1 H
C13A 0.2445(9) 0.8353(6) 0.3344(16) 0.179(4) Uani d PD 0.874(6) A 1 C
H131 0.2167 0.7941 0.1839 0.214 Uiso calc PR 0.874(6) A 1 H
C14A 0.3006(18) 0.9430(6) 0.245(3) 0.288(8) Uani d PD 0.874(6) A 1 C
H142 0.3886 0.9340 0.1373 0.433 Uiso calc PR 0.874(6) A 1 H
H141 0.3286 0.9824 0.3935 0.433 Uiso calc PR 0.874(6) A 1 H
H143 0.2198 0.9799 0.1477 0.433 Uiso calc PR 0.874(6) A 1 H
C15A 0.1029(11) 0.8553(9) 0.500(3) 0.265(6) Uani d PD 0.874(6) A 1 C
H153 0.0226 0.8887 0.3940 0.397 Uiso calc PR 0.874(6) A 1 H
H151 0.1296 0.8998 0.6394 0.397 Uiso calc PR 0.874(6) A 1 H
H152 0.0678 0.7898 0.5688 0.397 Uiso calc PR 0.874(6) A 1 H
C11B 0.3370(5) 0.6696(3) 0.5749(9) 0.1098(14) Uani d PD 0.126(6) A 2 C
H113 0.4414 0.6943 0.5864 0.132 Uiso calc PR 0.126(6) A 2 H
H114 0.3120 0.6385 0.7419 0.132 Uiso calc PR 0.126(6) A 2 H
C12B 0.226(2) 0.7623(11) 0.511(5) 0.158(3) Uani d PD 0.126(6) A 2 C
H123 0.1857 0.7549 0.3363 0.190 Uiso calc PR 0.126(6) A 2 H
H124 0.1400 0.7581 0.6276 0.190 Uiso calc PR 0.126(6) A 2 H
C13B 0.293(4) 0.8711(8) 0.531(7) 0.179(4) Uani d PD 0.126(6) A 2 C
H132 0.2095 0.9233 0.5035 0.214 Uiso calc PR 0.126(6) A 2 H
C14B 0.411(8) 0.888(4) 0.317(11) 0.288(8) Uani d PD 0.126(6) A 2 C
H144 0.4524 0.9566 0.3303 0.433 Uiso calc PR 0.126(6) A 2 H
H145 0.3611 0.8819 0.1507 0.433 Uiso calc PR 0.126(6) A 2 H
H146 0.4925 0.8361 0.3371 0.433 Uiso calc PR 0.126(6) A 2 H
C15B 0.368(6) 0.888(3) 0.797(10) 0.265(6) Uani d PD 0.126(6) A 2 C
H154 0.3793 0.9611 0.8222 0.397 Uiso calc PR 0.126(6) A 2 H
H155 0.4667 0.8526 0.8076 0.397 Uiso calc PR 0.126(6) A 2 H
H156 0.3031 0.8593 0.9295 0.397 Uiso calc PR 0.126(6) A 2 H
C21 0.2181(5) 0.3309(3) -0.1245(9) 0.1067(14) Uani d D 1 . . C
H211 0.2772 0.3384 -0.2811 0.128 Uiso calc R 1 A . H
H212 0.1099 0.3358 -0.1742 0.128 Uiso calc R 1 . . H
C22 0.2527(7) 0.2252(4) -0.0027(12) 0.145(2) Uani d D 1 A . C
H223 0.2259 0.1722 -0.1225 0.174 Uiso calc R 1 . . H
H222 0.1940 0.2169 0.1517 0.174 Uiso calc R 1 . . H
H221 0.3605 0.2187 0.0409 0.174 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0768(16) 0.125(2) 0.129(2) -0.0137(14) 0.0384(16) -0.0026(18)
O2 0.0712(16) 0.116(2) 0.129(2) -0.0131(14) 0.0339(15) -0.0055(17)
N1 0.0638(16) 0.091(2) 0.103(2) -0.0010(14) 0.0245(15) 0.0014(18)
N2 0.0661(17) 0.104(2) 0.109(2) -0.0023(15) 0.0234(16) -0.0014(19)
C1 0.068(2) 0.085(2) 0.106(3) 0.0029(17) 0.0175(19) 0.017(2)
C2 0.0628(19) 0.092(2) 0.102(3) 0.0040(17) 0.0193(19) 0.016(2)
C11A 0.092(3) 0.099(3) 0.139(4) 0.001(2) 0.022(3) 0.004(3)
C12A 0.151(6) 0.120(5) 0.209(8) -0.018(4) 0.075(6) -0.013(5)
C13A 0.201(9) 0.152(7) 0.178(8) 0.009(6) -0.019(7) 0.049(6)
C14A 0.48(2) 0.098(6) 0.287(14) -0.008(8) 0.042(14) 0.056(7)
C15A 0.151(8) 0.209(10) 0.432(19) 0.052(7) 0.029(10) -0.005(11)
C11B 0.092(3) 0.099(3) 0.139(4) 0.001(2) 0.022(3) 0.004(3)
C12B 0.151(6) 0.120(5) 0.209(8) -0.018(4) 0.075(6) -0.013(5)
C13B 0.201(9) 0.152(7) 0.178(8) 0.009(6) -0.019(7) 0.049(6)
C14B 0.48(2) 0.098(6) 0.287(14) -0.008(8) 0.042(14) 0.056(7)
C15B 0.151(8) 0.209(10) 0.432(19) 0.052(7) 0.029(10) -0.005(11)
C21 0.085(3) 0.113(3) 0.123(3) 0.002(2) 0.021(2) 0.000(3)
C22 0.150(5) 0.115(4) 0.169(5) 0.005(3) 0.017(4) 0.000(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.219(4) ?
O2 C2 . 1.231(4) ?
N1 C1 . 1.356(5) ?
N1 C2 . 1.393(5) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.326(5) ?
N2 C21 . 1.459(6) ?
N2 H21 . 0.8600 ?
C1 C11A . 1.501(6) ?
C11A C12A . 1.522(6) ?
C11A H111 . 0.9700 ?
C11A H112 . 0.9700 ?
C11A C12B . 1.530(18) ?
C12A C13A . 1.524(10) ?
C12A H121 . 0.9700 ?
C12A H122 . 0.9700 ?
C13A C15A . 1.531(14) ?
C13A C14A . 1.533(12) ?
C13A H131 . 0.9800 ?
C14A H142 . 0.9600 ?
C14A H141 . 0.9600 ?
C14A H143 . 0.9600 ?
C15A H153 . 0.9600 ?
C15A H151 . 0.9600 ?
C15A H152 . 0.9600 ?
C12B C13B . 1.53(2) ?
C12B H123 . 0.9700 ?
C12B H124 . 0.9700 ?
C13B C15B . 1.53(6) ?
C13B C14B . 1.53(7) ?
C13B H132 . 0.9800 ?
C14B H144 . 0.9600 ?
C14B H145 . 0.9600 ?
C14B H146 . 0.9600 ?
C15B H154 . 0.9600 ?
C15B H155 . 0.9600 ?
C15B H156 . 0.9600 ?
C21 C22 . 1.493(7) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 H223 . 0.9600 ?
C22 H222 . 0.9600 ?
C22 H221 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 129.5(3) ?
C1 N1 H11 . . 115.2 ?
C2 N1 H11 . . 115.2 ?
C2 N2 C21 . . 121.6(3) ?
C2 N2 H21 . . 119.2 ?
C21 N2 H21 . . 119.2 ?
O1 C1 N1 . . 123.1(4) ?
O1 C1 C11A . . 122.0(4) ?
N1 C1 C11A . . 114.8(3) ?
O2 C2 N2 . . 123.7(4) ?
O2 C2 N1 . . 118.5(3) ?
N2 C2 N1 . . 117.8(3) ?
C1 C11A C12A . . 118.0(4) ?
C1 C11A H111 . . 107.8 ?
C12A C11A H111 . . 107.8 ?
C1 C11A H112 . . 107.8 ?
C12A C11A H112 . . 107.8 ?
H111 C11A H112 . . 107.2 ?
C11A C12A C13A . . 112.2(5) ?
C11A C12A H121 . . 109.2 ?
C13A C12A H121 . . 109.2 ?
C11A C12A H122 . . 109.2 ?
C13A C12A H122 . . 109.2 ?
H121 C12A H122 . . 107.9 ?
C12A C13A C15A . . 112.2(7) ?
C12A C13A C14A . . 107.4(7) ?
C15A C13A C14A . . 106.7(10) ?
C12A C13A H131 . . 110.1 ?
C15A C13A H131 . . 110.1 ?
C14A C13A H131 . . 110.1 ?
C13A C14A H142 . . 109.5 ?
C13A C14A H141 . . 109.5 ?
H142 C14A H141 . . 109.5 ?
C13A C14A H143 . . 109.5 ?
H142 C14A H143 . . 109.5 ?
H141 C14A H143 . . 109.5 ?
C13A C15A H153 . . 109.5 ?
C13A C15A H151 . . 109.5 ?
H153 C15A H151 . . 109.5 ?
C13A C15A H152 . . 109.5 ?
H153 C15A H152 . . 109.5 ?
H151 C15A H152 . . 109.5 ?
C13B C12B H123 . . 108.3 ?
C13B C12B H124 . . 108.3 ?
H123 C12B H124 . . 107.4 ?
C12B C13B C15B . . 111.8(7) ?
C12B C13B C14B . . 109.9(7) ?
C15B C13B C14B . . 110.4(7) ?
C12B C13B H132 . . 108.2 ?
C15B C13B H132 . . 108.2 ?
C14B C13B H132 . . 108.2 ?
C13B C14B H144 . . 109.5 ?
C13B C14B H145 . . 109.5 ?
H144 C14B H145 . . 109.5 ?
C13B C14B H146 . . 109.5 ?
H144 C14B H146 . . 109.5 ?
H145 C14B H146 . . 109.5 ?
C13B C15B H154 . . 109.5 ?
C13B C15B H155 . . 109.5 ?
H154 C15B H155 . . 109.5 ?
C13B C15B H156 . . 109.5 ?
H154 C15B H156 . . 109.5 ?
H155 C15B H156 . . 109.5 ?
N2 C21 C22 . . 113.3(4) ?
N2 C21 H211 . . 108.9 ?
C22 C21 H211 . . 108.9 ?
N2 C21 H212 . . 108.9 ?
C22 C21 H212 . . 108.9 ?
H211 C21 H212 . . 107.7 ?
C21 C22 H223 . . 109.5 ?
C21 C22 H222 . . 109.5 ?
H223 C22 H222 . . 109.5 ?
C21 C22 H221 . . 109.5 ?
H223 C22 H221 . . 109.5 ?
H222 C22 H221 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 1.4(6) ?
C2 N1 C1 C11A . . . . -177.0(4) ?
C21 N2 C2 O2 . . . . 0.9(6) ?
C21 N2 C2 N1 . . . . -179.4(3) ?
C1 N1 C2 O2 . . . . -179.4(4) ?
C1 N1 C2 N2 . . . . 0.9(6) ?
O1 C1 C11A C12A . . . . 52.5(6) ?
N1 C1 C11A C12A . . . . -129.1(5) ?
C1 C11A C12A C13A . . . . 70.6(7) ?
C11A C12A C13A C15A . . . . 66.5(9) ?
C11A C12A C13A C14A . . . . -176.5(7) ?
C2 N2 C21 C22 . . . . -84.0(5) ?
C2 N1 C1 C11B . . . . -177.0(4) ?
O1 C1 C11B C12B . . . . 109.5(13) ?
N1 C1 C11B C12B . . . . -72.0(13) ?
C1 C11B C12B C13B . . . . -132.0(18) ?
C11B C12B C13B C15B . . . . -55(3) ?
C11B C12B C13B C14B . . . . 68(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.86 2.41 3.098(4) 137.1
N1 H11 O2 2_566 0.86 2.00 2.863(4) 177.8
data_ethyl370K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.605(2)
_cell_length_b 12.855(2)
_cell_length_c 5.1699(10)
_cell_angle_alpha 87.263(16)
_cell_angle_beta 92.266(9)
_cell_angle_gamma 88.060(8)
_cell_volume 570.39(19)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2605
_cell_measurement_theta_min 2.895
_cell_measurement_theta_max 27.445
_cell_measurement_temperature 370
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 1.00
_exptl_crystal_size_mid 1.00
_exptl_crystal_size_min 0.20
_exptl_crystal_density_diffrn 1.084
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.077
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being high temperature phase.
;
_diffrn_ambient_temperature 370
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 9055
_diffrn_reflns_av_R_equivalents 0.031
_diffrn_reflns_av_sigmaI/netI 0.0325
_diffrn_reflns_theta_min 2.37
_diffrn_reflns_theta_max 27.48
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measured_fraction_theta_full 0.863
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 2263
_reflns_number_gt 1016
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1977
_refine_ls_R_factor_gt 0.1160
_refine_ls_wR_factor_gt 0.3094
_refine_ls_wR_factor_ref 0.3859
_refine_ls_goodness_of_fit_ref 1.065
_refine_ls_restrained_S_all 1.065
_refine_ls_number_reflns 2263
_refine_ls_number_parameters 131
_refine_ls_number_restraints 17
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1627P)^2^+0.2588P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.278
_refine_diff_density_min -0.271
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 368K was used as an initial model.
The minor part of the disordered 3-methylbutyl group was
deleted to avoid some viases for disorder analysis.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.4305(4) 0.5716(3) 0.2153(8) 0.1207(14) Uani d . 1 A . O
O2 0.0278(4) 0.4110(3) 0.2582(8) 0.1167(14) Uani d . 1 A . O
N1 0.1965(4) 0.5326(3) 0.3720(8) 0.0955(13) Uani d . 1 A . N
H11 0.1305 0.5508 0.4836 0.115 Uiso calc R 1 . . H
N2 0.2530(4) 0.4165(3) 0.0519(8) 0.1012(14) Uani d D 1 A . N
H21 0.3406 0.4461 0.0375 0.121 Uiso calc R 1 . . H
C1 0.3268(5) 0.5873(4) 0.3646(10) 0.0971(15) Uani d D 1 . . C
C2 0.1552(5) 0.4504(4) 0.2223(11) 0.0985(15) Uani d . 1 . . C
C11A 0.3352(7) 0.6690(4) 0.5612(11) 0.124(2) Uani d PD 0.813(8) A 1 C
H111 0.4121 0.6450 0.6949 0.148 Uiso calc PR 0.813(8) A 1 H
H112 0.2355 0.6728 0.6420 0.148 Uiso calc PR 0.813(8) A 1 H
C12A 0.3745(11) 0.7794(5) 0.472(2) 0.177(4) Uani d PD 0.813(8) A 1 C
H121 0.4654 0.7767 0.3666 0.212 Uiso calc PR 0.813(8) A 1 H
H122 0.3997 0.8191 0.6216 0.212 Uiso calc PR 0.813(8) A 1 H
C13A 0.2393(13) 0.8341(8) 0.314(2) 0.190(5) Uani d PD 0.813(8) A 1 C
H131 0.2089 0.7940 0.1649 0.228 Uiso calc PR 0.813(8) A 1 H
C14A 0.292(3) 0.9422(9) 0.226(4) 0.333(12) Uani d PD 0.813(8) A 1 C
H142 0.3805 0.9348 0.1191 0.499 Uiso calc PR 0.813(8) A 1 H
H141 0.3210 0.9802 0.3748 0.499 Uiso calc PR 0.813(8) A 1 H
H143 0.2090 0.9793 0.1283 0.499 Uiso calc PR 0.813(8) A 1 H
C15A 0.0990(16) 0.8579(13) 0.477(4) 0.307(10) Uani d PD 0.813(8) A 1 C
H153 0.0174 0.8920 0.3691 0.461 Uiso calc PR 0.813(8) A 1 H
H151 0.1291 0.9026 0.6126 0.461 Uiso calc PR 0.813(8) A 1 H
H152 0.0623 0.7940 0.5525 0.461 Uiso calc PR 0.813(8) A 1 H
C11B 0.3352(7) 0.6690(4) 0.5612(11) 0.124(2) Uani d PD 0.187(8) A 2 C
H113 0.4408 0.6926 0.5774 0.148 Uiso calc PR 0.187(8) A 2 H
H114 0.3077 0.6393 0.7286 0.148 Uiso calc PR 0.187(8) A 2 H
C12B 0.224(2) 0.7617(10) 0.482(5) 0.177(4) Uani d PD 0.187(8) A 2 C
H123 0.1895 0.7551 0.3029 0.212 Uiso calc PR 0.187(8) A 2 H
H124 0.1336 0.7572 0.5866 0.212 Uiso calc PR 0.187(8) A 2 H
C13B 0.290(4) 0.8698(8) 0.507(7) 0.190(5) Uani d PD 0.187(8) A 2 C
H132 0.2034 0.9212 0.4914 0.228 Uiso calc PR 0.187(8) A 2 H
C14B 0.399(8) 0.893(4) 0.286(10) 0.333(12) Uani d PD 0.187(8) A 2 C
H144 0.4386 0.9616 0.3013 0.499 Uiso calc PR 0.187(8) A 2 H
H145 0.3428 0.8897 0.1230 0.499 Uiso calc PR 0.187(8) A 2 H
H146 0.4843 0.8427 0.2957 0.499 Uiso calc PR 0.187(8) A 2 H
C15B 0.376(5) 0.881(3) 0.769(9) 0.307(10) Uani d PD 0.187(8) A 2 C
H154 0.3904 0.9533 0.7959 0.461 Uiso calc PR 0.187(8) A 2 H
H155 0.4749 0.8445 0.7707 0.461 Uiso calc PR 0.187(8) A 2 H
H156 0.3148 0.8518 0.9044 0.461 Uiso calc PR 0.187(8) A 2 H
C21 0.2180(6) 0.3318(4) -0.1106(12) 0.1171(19) Uani d D 1 . . C
H211 0.2776 0.3384 -0.2656 0.140 Uiso calc R 1 A . H
H212 0.1085 0.3371 -0.1638 0.140 Uiso calc R 1 . . H
C22 0.2534(9) 0.2264(5) 0.0197(17) 0.167(3) Uani d D 1 A . C
H223 0.2272 0.1734 -0.0975 0.200 Uiso calc R 1 . . H
H222 0.1934 0.2187 0.1717 0.200 Uiso calc R 1 . . H
H221 0.3622 0.2198 0.0684 0.200 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.080(2) 0.146(3) 0.139(3) -0.0148(19) 0.037(2) -0.006(2)
O2 0.077(2) 0.129(3) 0.147(3) -0.0122(18) 0.034(2) -0.011(2)
N1 0.070(2) 0.100(3) 0.117(3) -0.0018(19) 0.025(2) -0.001(2)
N2 0.071(2) 0.114(3) 0.120(3) -0.003(2) 0.023(2) -0.004(3)
C1 0.070(3) 0.098(3) 0.123(4) 0.000(2) 0.017(3) 0.008(3)
C2 0.062(2) 0.114(4) 0.119(4) 0.005(2) 0.027(2) 0.016(3)
C11A 0.095(4) 0.110(4) 0.166(6) -0.002(3) 0.021(3) 0.002(4)
C12A 0.168(9) 0.138(7) 0.231(11) -0.024(6) 0.088(9) 0.000(7)
C13A 0.191(11) 0.173(9) 0.197(12) -0.007(8) -0.029(9) 0.054(9)
C14A 0.54(4) 0.117(9) 0.34(2) 0.007(13) 0.04(2) 0.053(11)
C15A 0.143(11) 0.246(16) 0.53(3) 0.046(10) 0.048(14) -0.045(17)
C11B 0.095(4) 0.110(4) 0.166(6) -0.002(3) 0.021(3) 0.002(4)
C12B 0.168(9) 0.138(7) 0.231(11) -0.024(6) 0.088(9) 0.000(7)
C13B 0.191(11) 0.173(9) 0.197(12) -0.007(8) -0.029(9) 0.054(9)
C14B 0.54(4) 0.117(9) 0.34(2) 0.007(13) 0.04(2) 0.053(11)
C15B 0.143(11) 0.246(16) 0.53(3) 0.046(10) 0.048(14) -0.045(17)
C21 0.088(3) 0.125(4) 0.138(5) 0.006(3) 0.016(3) -0.004(4)
C22 0.153(7) 0.126(5) 0.222(9) 0.008(5) 0.020(6) -0.018(6)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.221(6) ?
O2 C2 . 1.241(6) ?
N1 C1 . 1.345(6) ?
N1 C2 . 1.386(7) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.321(6) ?
N2 C21 . 1.440(7) ?
N2 H21 . 0.8600 ?
C1 C11A . 1.497(7) ?
C11A C12A . 1.525(9) ?
C11A H111 . 0.9700 ?
C11A H112 . 0.9700 ?
C11A C12B . 1.530(17) ?
C12A C13A . 1.526(14) ?
C12A H121 . 0.9700 ?
C12A H122 . 0.9700 ?
C13A C15A . 1.53(2) ?
C13A C14A . 1.532(18) ?
C13A H131 . 0.9800 ?
C14A H142 . 0.9600 ?
C14A H141 . 0.9600 ?
C14A H143 . 0.9600 ?
C15A H153 . 0.9600 ?
C15A H151 . 0.9600 ?
C15A H152 . 0.9600 ?
C12B C13B . 1.53(2) ?
C12B H123 . 0.9700 ?
C12B H124 . 0.9700 ?
C13B C15B . 1.53(6) ?
C13B C14B . 1.53(7) ?
C13B H132 . 0.9800 ?
C14B H144 . 0.9600 ?
C14B H145 . 0.9600 ?
C14B H146 . 0.9600 ?
C15B H154 . 0.9600 ?
C15B H155 . 0.9600 ?
C15B H156 . 0.9600 ?
C21 C22 . 1.500(9) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 H223 . 0.9600 ?
C22 H222 . 0.9600 ?
C22 H221 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 128.1(4) ?
C1 N1 H11 . . 115.9 ?
C2 N1 H11 . . 115.9 ?
C2 N2 C21 . . 122.3(4) ?
C2 N2 H21 . . 118.9 ?
C21 N2 H21 . . 118.9 ?
O1 C1 N1 . . 123.7(5) ?
O1 C1 C11A . . 122.6(5) ?
N1 C1 C11A . . 113.7(4) ?
O2 C2 N2 . . 122.9(6) ?
O2 C2 N1 . . 117.9(4) ?
N2 C2 N1 . . 119.2(4) ?
C1 C11A C12A . . 118.6(6) ?
C1 C11A H111 . . 107.7 ?
C12A C11A H111 . . 107.7 ?
C1 C11A H112 . . 107.7 ?
C12A C11A H112 . . 107.7 ?
H111 C11A H112 . . 107.1 ?
C11A C12A C13A . . 111.5(7) ?
C11A C12A H121 . . 109.3 ?
C13A C12A H121 . . 109.3 ?
C11A C12A H122 . . 109.3 ?
C13A C12A H122 . . 109.3 ?
H121 C12A H122 . . 108.0 ?
C12A C13A C15A . . 112.9(10) ?
C12A C13A C14A . . 107.4(11) ?
C15A C13A C14A . . 103.6(14) ?
C12A C13A H131 . . 110.9 ?
C15A C13A H131 . . 110.9 ?
C14A C13A H131 . . 110.9 ?
C13A C14A H142 . . 109.5 ?
C13A C14A H141 . . 109.5 ?
H142 C14A H141 . . 109.5 ?
C13A C14A H143 . . 109.5 ?
H142 C14A H143 . . 109.5 ?
H141 C14A H143 . . 109.5 ?
C13A C15A H153 . . 109.5 ?
C13A C15A H151 . . 109.5 ?
H153 C15A H151 . . 109.5 ?
C13A C15A H152 . . 109.5 ?
H153 C15A H152 . . 109.5 ?
H151 C15A H152 . . 109.5 ?
C13B C12B H123 . . 108.2 ?
C13B C12B H124 . . 108.2 ?
H123 C12B H124 . . 107.4 ?
C12B C13B C15B . . 112.2(7) ?
C12B C13B C14B . . 109.9(7) ?
C15B C13B C14B . . 110.3(7) ?
C12B C13B H132 . . 108.1 ?
C15B C13B H132 . . 108.1 ?
C14B C13B H132 . . 108.1 ?
C13B C14B H144 . . 109.5 ?
C13B C14B H145 . . 109.5 ?
H144 C14B H145 . . 109.5 ?
C13B C14B H146 . . 109.5 ?
H144 C14B H146 . . 109.5 ?
H145 C14B H146 . . 109.5 ?
C13B C15B H154 . . 109.5 ?
C13B C15B H155 . . 109.5 ?
H154 C15B H155 . . 109.5 ?
C13B C15B H156 . . 109.5 ?
H154 C15B H156 . . 109.5 ?
H155 C15B H156 . . 109.5 ?
N2 C21 C22 . . 113.4(5) ?
N2 C21 H211 . . 108.9 ?
C22 C21 H211 . . 108.9 ?
N2 C21 H212 . . 108.9 ?
C22 C21 H212 . . 108.9 ?
H211 C21 H212 . . 107.7 ?
C21 C22 H223 . . 109.5 ?
C21 C22 H222 . . 109.5 ?
H223 C22 H222 . . 109.5 ?
C21 C22 H221 . . 109.5 ?
H223 C22 H221 . . 109.5 ?
H222 C22 H221 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 0.7(8) ?
C2 N1 C1 C11A . . . . -178.1(5) ?
C21 N2 C2 O2 . . . . 1.3(8) ?
C21 N2 C2 N1 . . . . -179.8(5) ?
C1 N1 C2 O2 . . . . -179.2(4) ?
C1 N1 C2 N2 . . . . 1.8(8) ?
O1 C1 C11A C12A . . . . 50.8(8) ?
N1 C1 C11A C12A . . . . -130.3(6) ?
C1 C11A C12A C13A . . . . 72.2(10) ?
C11A C12A C13A C15A . . . . 68.4(13) ?
C11A C12A C13A C14A . . . . -178.0(11) ?
C2 N2 C21 C22 . . . . -83.3(6) ?
C2 N1 C1 C11B . . . . -178.1(5) ?
O1 C1 C11B C12B . . . . 107.1(13) ?
N1 C1 C11B C12B . . . . -74.1(12) ?
C1 C11B C12B C13B . . . . -134.6(18) ?
C11B C12B C13B C15B . . . . -47(3) ?
C11B C12B C13B C14B . . . . 76(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.86 2.42 3.107(5) 137.7
N1 H11 O2 2_566 0.86 2.01 2.870(5) 178.0
data_ethyl372K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.6137(18)
_cell_length_b 12.994(3)
_cell_length_c 5.1906(11)
_cell_angle_alpha 86.197(10)
_cell_angle_beta 91.616(12)
_cell_angle_gamma 88.099(6)
_cell_volume 579.1(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2962
_cell_measurement_theta_min 2.79
_cell_measurement_theta_max 27.48
_cell_measurement_temperature 372
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 1.00
_exptl_crystal_size_mid 0.60
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.068
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.076
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being high temperature phase.
;
_diffrn_ambient_temperature 372
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 8178
_diffrn_reflns_av_R_equivalents 0.040
_diffrn_reflns_av_sigmaI/netI 0.0291
_diffrn_reflns_theta_min 2.80
_diffrn_reflns_theta_max 27.48
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measured_fraction_theta_full 0.868
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 2312
_reflns_number_gt 1114
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1865
_refine_ls_R_factor_gt 0.1244
_refine_ls_wR_factor_gt 0.3045
_refine_ls_wR_factor_ref 0.3336
_refine_ls_goodness_of_fit_ref 1.753
_refine_ls_restrained_S_all 1.772
_refine_ls_number_reflns 2312
_refine_ls_number_parameters 131
_refine_ls_number_restraints 17
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.387
_refine_diff_density_min -0.293
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 370K was used as an initial model.
The minor part of the disordered 3-methylbutyl group was
deleted to avoid some viases for disorder analysis.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.4299(3) 0.5710(2) 0.2076(6) 0.1290(10) Uani d . 1 A . O
O2 0.0275(2) 0.41152(19) 0.2663(5) 0.1204(9) Uani d . 1 A . O
N1 0.1962(3) 0.5315(2) 0.3685(6) 0.1017(9) Uani d . 1 A . N
H11 0.1302 0.5501 0.4793 0.122 Uiso calc R 1 . . H
N2 0.2536(3) 0.4159(2) 0.0604(6) 0.1066(10) Uani d D 1 A . N
H21 0.3419 0.4445 0.0464 0.128 Uiso calc R 1 . . H
C1 0.3266(4) 0.5868(2) 0.3546(7) 0.1013(11) Uani d D 1 . . C
C2 0.1551(4) 0.4493(3) 0.2288(7) 0.1005(10) Uani d . 1 . . C
C11A 0.3342(5) 0.6684(2) 0.5442(8) 0.1283(14) Uani d PD 0.774(6) A 1 C
H111 0.4095 0.6449 0.6797 0.154 Uiso calc PR 0.774(6) A 1 H
H112 0.2338 0.6734 0.6235 0.154 Uiso calc PR 0.774(6) A 1 H
C12A 0.3760(7) 0.7768(3) 0.4458(17) 0.203(4) Uani d PD 0.774(6) A 1 C
H121 0.4117 0.8143 0.5903 0.243 Uiso calc PR 0.774(6) A 1 H
H122 0.4606 0.7720 0.3273 0.243 Uiso calc PR 0.774(6) A 1 H
C13A 0.2389(8) 0.8363(6) 0.3087(18) 0.219(5) Uani d PD 0.774(6) A 1 C
H131 0.2028 0.7964 0.1663 0.263 Uiso calc PR 0.774(6) A 1 H
C14A 0.284(2) 0.9425(7) 0.195(3) 0.382(11) Uani d PD 0.774(6) A 1 C
H142 0.3715 0.9348 0.0870 0.574 Uiso calc PR 0.774(6) A 1 H
H141 0.3097 0.9854 0.3320 0.574 Uiso calc PR 0.774(6) A 1 H
H143 0.1976 0.9739 0.0932 0.574 Uiso calc PR 0.774(6) A 1 H
C15A 0.0997(13) 0.8609(12) 0.471(3) 0.343(8) Uani d PD 0.774(6) A 1 C
H153 0.0187 0.8947 0.3623 0.515 Uiso calc PR 0.774(6) A 1 H
H151 0.1302 0.9055 0.6023 0.515 Uiso calc PR 0.774(6) A 1 H
H152 0.0623 0.7981 0.5506 0.515 Uiso calc PR 0.774(6) A 1 H
C11B 0.3342(5) 0.6684(2) 0.5442(8) 0.1283(14) Uani d PD 0.226(6) A 2 C
H113 0.4411 0.6872 0.5726 0.154 Uiso calc PR 0.226(6) A 2 H
H114 0.2940 0.6429 0.7082 0.154 Uiso calc PR 0.226(6) A 2 H
C12B 0.2364(14) 0.7629(5) 0.434(3) 0.203(4) Uani d PD 0.226(6) A 2 C
H123 0.2284 0.7604 0.2479 0.243 Uiso calc PR 0.226(6) A 2 H
H124 0.1322 0.7575 0.4991 0.243 Uiso calc PR 0.226(6) A 2 H
C13B 0.2968(16) 0.8678(6) 0.495(2) 0.219(5) Uani d PD 0.226(6) A 2 C
H132 0.2084 0.9173 0.4930 0.263 Uiso calc PR 0.226(6) A 2 H
C14B 0.408(3) 0.904(2) 0.287(4) 0.382(11) Uani d PD 0.226(6) A 2 C
H144 0.4415 0.9723 0.3196 0.574 Uiso calc PR 0.226(6) A 2 H
H145 0.3566 0.9061 0.1206 0.574 Uiso calc PR 0.226(6) A 2 H
H146 0.4974 0.8577 0.2904 0.574 Uiso calc PR 0.226(6) A 2 H
C15B 0.378(3) 0.8645(19) 0.761(3) 0.343(8) Uani d PD 0.226(6) A 2 C
H154 0.3968 0.9336 0.8066 0.515 Uiso calc PR 0.226(6) A 2 H
H155 0.4755 0.8264 0.7572 0.515 Uiso calc PR 0.226(6) A 2 H
H156 0.3137 0.8314 0.8874 0.515 Uiso calc PR 0.226(6) A 2 H
C21 0.2183(4) 0.3335(3) -0.1002(8) 0.1250(14) Uani d D 1 . . C
H211 0.2782 0.3406 -0.2555 0.150 Uiso calc R 1 A . H
H212 0.1091 0.3391 -0.1519 0.150 Uiso calc R 1 . . H
C22 0.2530(7) 0.2286(4) 0.0324(12) 0.171(2) Uani d D 1 A . C
H223 0.2273 0.1765 -0.0827 0.205 Uiso calc R 1 . . H
H222 0.1925 0.2205 0.1845 0.205 Uiso calc R 1 . . H
H221 0.3615 0.2219 0.0803 0.205 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0883(14) 0.142(2) 0.160(2) -0.0232(14) 0.0507(15) -0.0064(17)
O2 0.0841(14) 0.1289(19) 0.153(2) -0.0235(13) 0.0434(14) -0.0172(16)
N1 0.0761(14) 0.110(2) 0.121(2) -0.0094(14) 0.0330(14) -0.0047(17)
N2 0.0749(15) 0.114(2) 0.134(2) -0.0090(14) 0.0292(16) -0.0123(18)
C1 0.0783(18) 0.100(2) 0.124(3) -0.0042(16) 0.0224(18) 0.017(2)
C2 0.0698(17) 0.112(2) 0.118(3) -0.0006(17) 0.0233(18) 0.007(2)
C11A 0.104(3) 0.111(3) 0.171(4) -0.009(2) 0.025(3) -0.006(3)
C12A 0.182(7) 0.128(5) 0.304(10) -0.031(5) 0.103(8) -0.009(5)
C13A 0.230(9) 0.173(7) 0.241(11) -0.039(6) -0.060(8) 0.074(7)
C14A 0.63(3) 0.120(7) 0.385(19) -0.002(10) 0.07(2) 0.054(8)
C15A 0.177(9) 0.357(17) 0.51(2) 0.045(10) 0.075(12) -0.105(15)
C11B 0.104(3) 0.111(3) 0.171(4) -0.009(2) 0.025(3) -0.006(3)
C12B 0.182(7) 0.128(5) 0.304(10) -0.031(5) 0.103(8) -0.009(5)
C13B 0.230(9) 0.173(7) 0.241(11) -0.039(6) -0.060(8) 0.074(7)
C14B 0.63(3) 0.120(7) 0.385(19) -0.002(10) 0.07(2) 0.054(8)
C15B 0.177(9) 0.357(17) 0.51(2) 0.045(10) 0.075(12) -0.105(15)
C21 0.101(2) 0.131(3) 0.144(4) -0.004(2) 0.031(2) -0.008(3)
C22 0.178(5) 0.141(4) 0.193(5) 0.007(3) 0.006(4) -0.014(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.210(4) ?
O2 C2 . 1.233(4) ?
N1 C1 . 1.354(4) ?
N1 C2 . 1.381(5) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.319(4) ?
N2 C21 . 1.436(5) ?
N2 H21 . 0.8600 ?
C1 C11A . 1.496(5) ?
C11A C12A . 1.523(6) ?
C11A H111 . 0.9700 ?
C11A H112 . 0.9700 ?
C11A C12B . 1.534(10) ?
C12A C13A . 1.522(9) ?
C12A H121 . 0.9700 ?
C12A H122 . 0.9700 ?
C13A C15A . 1.522(16) ?
C13A C14A . 1.530(14) ?
C13A H131 . 0.9800 ?
C14A H142 . 0.9600 ?
C14A H141 . 0.9600 ?
C14A H143 . 0.9600 ?
C15A H153 . 0.9600 ?
C15A H151 . 0.9600 ?
C15A H152 . 0.9600 ?
C12B C13B . 1.525(12) ?
C12B H123 . 0.9700 ?
C12B H124 . 0.9700 ?
C13B C15B . 1.53(2) ?
C13B C14B . 1.53(3) ?
C13B H132 . 0.9800 ?
C14B H144 . 0.9600 ?
C14B H145 . 0.9600 ?
C14B H146 . 0.9600 ?
C15B H154 . 0.9600 ?
C15B H155 . 0.9600 ?
C15B H156 . 0.9600 ?
C21 C22 . 1.502(6) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 H223 . 0.9600 ?
C22 H222 . 0.9600 ?
C22 H221 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 128.7(3) ?
C1 N1 H11 . . 115.7 ?
C2 N1 H11 . . 115.7 ?
C2 N2 C21 . . 122.2(3) ?
C2 N2 H21 . . 118.9 ?
C21 N2 H21 . . 118.9 ?
O1 C1 N1 . . 123.8(3) ?
O1 C1 C11A . . 122.4(3) ?
N1 C1 C11A . . 113.8(3) ?
O2 C2 N2 . . 123.4(4) ?
O2 C2 N1 . . 118.3(3) ?
N2 C2 N1 . . 118.3(3) ?
C1 C11A C12A . . 118.2(4) ?
C1 C11A H111 . . 107.8 ?
C12A C11A H111 . . 107.8 ?
C1 C11A H112 . . 107.8 ?
C12A C11A H112 . . 107.8 ?
H111 C11A H112 . . 107.1 ?
C13A C12A C11A . . 112.3(5) ?
C13A C12A H121 . . 109.1 ?
C11A C12A H121 . . 109.1 ?
C13A C12A H122 . . 109.1 ?
C11A C12A H122 . . 109.1 ?
H121 C12A H122 . . 107.9 ?
C12A C13A C15A . . 117.0(8) ?
C12A C13A C14A . . 112.3(9) ?
C15A C13A C14A . . 103.3(11) ?
C12A C13A H131 . . 108.0 ?
C15A C13A H131 . . 108.0 ?
C14A C13A H131 . . 108.0 ?
C13A C14A H142 . . 109.5 ?
C13A C14A H141 . . 109.5 ?
H142 C14A H141 . . 109.5 ?
C13A C14A H143 . . 109.5 ?
H142 C14A H143 . . 109.5 ?
H141 C14A H143 . . 109.5 ?
C13A C15A H153 . . 109.5 ?
C13A C15A H151 . . 109.5 ?
H153 C15A H151 . . 109.5 ?
C13A C15A H152 . . 109.5 ?
H153 C15A H152 . . 109.5 ?
H151 C15A H152 . . 109.5 ?
C13B C12B H123 . . 108.3 ?
C13B C12B H124 . . 108.3 ?
H123 C12B H124 . . 107.4 ?
C12B C13B C15B . . 112.0(7) ?
C12B C13B C14B . . 109.5(7) ?
C15B C13B C14B . . 109.9(7) ?
C12B C13B H132 . . 108.4 ?
C15B C13B H132 . . 108.4 ?
C14B C13B H132 . . 108.4 ?
C13B C14B H144 . . 109.5 ?
C13B C14B H145 . . 109.5 ?
H144 C14B H145 . . 109.5 ?
C13B C14B H146 . . 109.5 ?
H144 C14B H146 . . 109.5 ?
H145 C14B H146 . . 109.5 ?
C13B C15B H154 . . 109.5 ?
C13B C15B H155 . . 109.5 ?
H154 C15B H155 . . 109.5 ?
C13B C15B H156 . . 109.5 ?
H154 C15B H156 . . 109.5 ?
H155 C15B H156 . . 109.5 ?
N2 C21 C22 . . 112.8(4) ?
N2 C21 H211 . . 109.0 ?
C22 C21 H211 . . 109.0 ?
N2 C21 H212 . . 109.0 ?
C22 C21 H212 . . 109.0 ?
H211 C21 H212 . . 107.8 ?
C21 C22 H223 . . 109.5 ?
C21 C22 H222 . . 109.5 ?
H223 C22 H222 . . 109.5 ?
C21 C22 H221 . . 109.5 ?
H223 C22 H221 . . 109.5 ?
H222 C22 H221 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 0.6(6) ?
C2 N1 C1 C11A . . . . -177.8(3) ?
C21 N2 C2 O2 . . . . 1.7(5) ?
C21 N2 C2 N1 . . . . -177.6(3) ?
C1 N1 C2 O2 . . . . -177.8(3) ?
C1 N1 C2 N2 . . . . 1.6(5) ?
O1 C1 C11A C12A . . . . 49.9(5) ?
N1 C1 C11A C12A . . . . -131.7(4) ?
C1 C11A C12A C13A . . . . 78.5(7) ?
C11A C12A C13A C15A . . . . 64.5(11) ?
C11A C12A C13A C14A . . . . -176.3(9) ?
C2 N2 C21 C22 . . . . -84.1(5) ?
C2 N1 C1 C11B . . . . -177.8(3) ?
O1 C1 C11B C12B . . . . 100.4(7) ?
N1 C1 C11B C12B . . . . -81.1(7) ?
C1 C11B C12B C13B . . . . -145.1(10) ?
C11B C12B C13B C15B . . . . -33.4(17) ?
C11B C12B C13B C14B . . . . 88.8(17) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.86 2.41 3.100(3) 137.9
N1 H11 O2 2_566 0.86 2.00 2.855(4) 177.8
data_ethyl374K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-ethyl-3-(4-methylpentanoyl)urea
;
_chemical_name_common ?
_chemical_formula_moiety 'C9 H18 N2 O2'
_chemical_formula_sum 'C9 H18 N2 O2'
_chemical_formula_weight 186.25
_chemical_melting_point 375
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.6337(14)
_cell_length_b 13.1782(16)
_cell_length_c 5.2242(18)
_cell_angle_alpha 85.948(12)
_cell_angle_beta 91.71(2)
_cell_angle_gamma 88.030(13)
_cell_volume 592.2(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 1921
_cell_measurement_theta_min 1.55
_cell_measurement_theta_max 27.435
_cell_measurement_temperature 374
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 1.00
_exptl_crystal_size_mid 0.60
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.044
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 204
_exptl_absorpt_coefficient_mu 0.074
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
The crystal was being high temperature phase.
;
_diffrn_ambient_temperature 374
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 8267
_diffrn_reflns_av_R_equivalents 0.041
_diffrn_reflns_av_sigmaI/netI 0.0369
_diffrn_reflns_theta_min 2.36
_diffrn_reflns_theta_max 27.47
_diffrn_reflns_theta_full 27.47
_diffrn_measured_fraction_theta_max 0.724
_diffrn_measured_fraction_theta_full 0.724
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 1962
_reflns_number_gt 826
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.2397
_refine_ls_R_factor_gt 0.1519
_refine_ls_wR_factor_gt 0.3442
_refine_ls_wR_factor_ref 0.3786
_refine_ls_goodness_of_fit_ref 1.846
_refine_ls_restrained_S_all 1.846
_refine_ls_number_reflns 1962
_refine_ls_number_parameters 131
_refine_ls_number_restraints 17
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.220
_refine_diff_density_min -0.222
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 372K was used as an initial model.
The minor part of the disordered 3-methylbutyl group was
deleted to avoid some viases for disorder analysis.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.4309(4) 0.5705(3) 0.2056(8) 0.1487(15) Uani d . 1 A . O
O2 0.0265(4) 0.4115(2) 0.2684(8) 0.1411(15) Uani d . 1 A . O
N1 0.1966(4) 0.5311(3) 0.3691(9) 0.1209(14) Uani d . 1 A . N
H11 0.1319 0.5483 0.4816 0.145 Uiso calc R 1 . . H
N2 0.2533(4) 0.4162(3) 0.0625(9) 0.1289(16) Uani d D 1 A . N
H21 0.3412 0.4442 0.0446 0.155 Uiso calc R 1 . . H
C1 0.3248(5) 0.5871(3) 0.3521(10) 0.1222(18) Uani d D 1 . . C
C2 0.1557(5) 0.4510(4) 0.2330(11) 0.1156(17) Uani d . 1 . . C
C11A 0.3332(6) 0.6684(3) 0.5374(11) 0.148(2) Uani d PD 0.765(6) A 1 C
H111 0.4093 0.6458 0.6715 0.178 Uiso calc PR 0.765(6) A 1 H
H112 0.2335 0.6734 0.6174 0.178 Uiso calc PR 0.765(6) A 1 H
C12A 0.3736(9) 0.7748(5) 0.435(2) 0.227(5) Uani d PD 0.765(6) A 1 C
H122 0.4541 0.7692 0.3107 0.272 Uiso calc PR 0.765(6) A 1 H
H121 0.4154 0.8108 0.5758 0.272 Uiso calc PR 0.765(6) A 1 H
C13A 0.2368(10) 0.8371(7) 0.309(2) 0.248(7) Uani d PD 0.765(6) A 1 C
H131 0.2004 0.7995 0.1650 0.298 Uiso calc PR 0.765(6) A 1 H
C14A 0.277(2) 0.9430(8) 0.194(3) 0.366(14) Uani d PD 0.765(6) A 1 C
H142 0.3645 0.9369 0.0865 0.549 Uiso calc PR 0.765(6) A 1 H
H141 0.3021 0.9855 0.3304 0.549 Uiso calc PR 0.765(6) A 1 H
H143 0.1898 0.9728 0.0944 0.549 Uiso calc PR 0.765(6) A 1 H
C15A 0.0940(18) 0.8608(14) 0.463(5) 0.396(14) Uani d PD 0.765(6) A 1 C
H153 0.0151 0.8944 0.3507 0.594 Uiso calc PR 0.765(6) A 1 H
H151 0.1215 0.9043 0.5954 0.594 Uiso calc PR 0.765(6) A 1 H
H152 0.0556 0.7985 0.5390 0.594 Uiso calc PR 0.765(6) A 1 H
C11B 0.3332(6) 0.6684(3) 0.5374(11) 0.148(2) Uani d PD 0.235(6) A 2 C
H113 0.4389 0.6904 0.5526 0.178 Uiso calc PR 0.235(6) A 2 H
H114 0.3028 0.6415 0.7054 0.178 Uiso calc PR 0.235(6) A 2 H
C12B 0.2253(14) 0.7593(6) 0.444(3) 0.227(5) Uani d PD 0.235(6) A 2 C
H123 0.2134 0.7607 0.2588 0.272 Uiso calc PR 0.235(6) A 2 H
H124 0.1240 0.7490 0.5149 0.272 Uiso calc PR 0.235(6) A 2 H
C13B 0.2811(16) 0.8627(6) 0.517(2) 0.248(7) Uani d PD 0.235(6) A 2 C
H132 0.1928 0.9117 0.5045 0.298 Uiso calc PR 0.235(6) A 2 H
C14B 0.403(3) 0.900(2) 0.328(4) 0.366(14) Uani d PD 0.235(6) A 2 C
H144 0.4330 0.9665 0.3660 0.549 Uiso calc PR 0.235(6) A 2 H
H145 0.3604 0.9014 0.1562 0.549 Uiso calc PR 0.235(6) A 2 H
H146 0.4923 0.8537 0.3447 0.549 Uiso calc PR 0.235(6) A 2 H
C15B 0.350(4) 0.856(2) 0.791(3) 0.396(14) Uani d PD 0.235(6) A 2 C
H154 0.3691 0.9235 0.8409 0.594 Uiso calc PR 0.235(6) A 2 H
H155 0.4452 0.8164 0.7993 0.594 Uiso calc PR 0.235(6) A 2 H
H156 0.2777 0.8247 0.9059 0.594 Uiso calc PR 0.235(6) A 2 H
C21 0.2164(6) 0.3329(4) -0.0932(10) 0.143(2) Uani d D 1 . . C
H211 0.2718 0.3396 -0.2520 0.172 Uiso calc R 1 A . H
H212 0.1062 0.3359 -0.1364 0.172 Uiso calc R 1 . . H
C22 0.2604(9) 0.2311(4) 0.0485(16) 0.204(4) Uani d D 1 A . C
H223 0.2366 0.1772 -0.0590 0.245 Uiso calc R 1 . . H
H222 0.2031 0.2235 0.2029 0.245 Uiso calc R 1 . . H
H221 0.3695 0.2281 0.0914 0.245 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.102(2) 0.168(3) 0.182(3) -0.029(2) 0.051(2) -0.024(3)
O2 0.094(2) 0.140(3) 0.196(4) -0.0257(18) 0.052(2) -0.027(2)
N1 0.083(2) 0.124(3) 0.160(4) -0.021(2) 0.039(3) -0.018(3)
N2 0.087(2) 0.132(3) 0.173(4) -0.013(2) 0.039(3) -0.026(3)
C1 0.084(3) 0.116(3) 0.165(5) 0.003(3) 0.027(3) 0.007(3)
C2 0.064(2) 0.138(4) 0.142(5) 0.003(3) 0.015(3) 0.010(3)
C11A 0.115(4) 0.119(4) 0.213(6) -0.017(3) 0.030(4) -0.018(4)
C12A 0.187(9) 0.172(7) 0.325(14) -0.015(7) 0.108(11) 0.005(8)
C13A 0.204(11) 0.269(12) 0.248(14) -0.030(10) -0.074(11) 0.118(12)
C14A 0.62(4) 0.131(9) 0.34(2) -0.042(13) -0.03(2) 0.072(10)
C15A 0.181(13) 0.35(2) 0.68(4) 0.033(13) 0.10(2) -0.17(2)
C11B 0.115(4) 0.119(4) 0.213(6) -0.017(3) 0.030(4) -0.018(4)
C12B 0.187(9) 0.172(7) 0.325(14) -0.015(7) 0.108(11) 0.005(8)
C13B 0.204(11) 0.269(12) 0.248(14) -0.030(10) -0.074(11) 0.118(12)
C14B 0.62(4) 0.131(9) 0.34(2) -0.042(13) -0.03(2) 0.072(10)
C15B 0.181(13) 0.35(2) 0.68(4) 0.033(13) 0.10(2) -0.17(2)
C21 0.103(4) 0.149(4) 0.178(6) 0.000(3) 0.037(4) -0.007(4)
C22 0.192(7) 0.147(5) 0.278(10) -0.009(5) 0.043(8) -0.039(6)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.234(6) ?
O2 C2 . 1.261(6) ?
N1 C1 . 1.353(6) ?
N1 C2 . 1.364(7) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.338(6) ?
N2 C21 . 1.450(7) ?
N2 H21 . 0.8600 ?
C1 C11A . 1.496(7) ?
C11A C12A . 1.521(9) ?
C11A H111 . 0.9700 ?
C11A H112 . 0.9700 ?
C11A C12B . 1.53(11) ?
C12A C13A . 1.521(12) ?
C12A H122 . 0.9700 ?
C12A H121 . 0.9700 ?
C13A C15A . 1.53(2) ?
C13A C14A . 1.534(16) ?
C13A H131 . 0.9800 ?
C14A H142 . 0.9600 ?
C14A H141 . 0.9600 ?
C14A H143 . 0.9600 ?
C15A H153 . 0.9600 ?
C15A H151 . 0.9600 ?
C15A H152 . 0.9600 ?
C12B C13B . 1.530(13) ?
C12B H123 . 0.9700 ?
C12B H124 . 0.9700 ?
C13B C15B . 1.53(2) ?
C13B C14B . 1.53(3) ?
C13B H132 . 0.9800 ?
C14B H144 . 0.9600 ?
C14B H145 . 0.9600 ?
C14B H146 . 0.9600 ?
C15B H154 . 0.9600 ?
C15B H155 . 0.9600 ?
C15B H156 . 0.9600 ?
C21 C22 . 1.517(8) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 H223 . 0.9600 ?
C22 H222 . 0.9600 ?
C22 H221 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 129.1(4) ?
C1 N1 H11 . . 115.5 ?
C2 N1 H11 . . 115.5 ?
C2 N2 C21 . . 122.5(4) ?
C2 N2 H21 . . 118.8 ?
C21 N2 H21 . . 118.8 ?
O1 C1 N1 . . 123.6(4) ?
O1 C1 C11A . . 121.8(4) ?
N1 C1 C11A . . 114.5(4) ?
O2 C2 N2 . . 121.1(6) ?
O2 C2 N1 . . 119.6(4) ?
N2 C2 N1 . . 119.3(4) ?
C1 C11A C12A . . 118.1(6) ?
C1 C11A H111 . . 107.8 ?
C12A C11A H111 . . 107.8 ?
C1 C11A H112 . . 107.8 ?
C12A C11A H112 . . 107.8 ?
H111 C11A H112 . . 107.1 ?
C11A C12A C13A . . 113.9(6) ?
C11A C12A H122 . . 108.8 ?
C13A C12A H122 . . 108.8 ?
C11A C12A H121 . . 108.8 ?
C13A C12A H121 . . 108.8 ?
H122 C12A H121 . . 107.7 ?
C12A C13A C15A . . 120.4(12) ?
C12A C13A C14A . . 114.5(10) ?
C15A C13A C14A . . 102.2(13) ?
C12A C13A H131 . . 106.3 ?
C15A C13A H131 . . 106.3 ?
C14A C13A H131 . . 106.3 ?
C13A C14A H142 . . 109.5 ?
C13A C14A H141 . . 109.5 ?
H142 C14A H141 . . 109.5 ?
C13A C14A H143 . . 109.5 ?
H142 C14A H143 . . 109.5 ?
H141 C14A H143 . . 109.5 ?
C13A C15A H153 . . 109.5 ?
C13A C15A H151 . . 109.5 ?
H153 C15A H151 . . 109.5 ?
C13A C15A H152 . . 109.5 ?
H153 C15A H152 . . 109.5 ?
H151 C15A H152 . . 109.5 ?
C13B C12B H123 . . 108.6 ?
C13B C12B H124 . . 108.6 ?
H123 C12B H124 . . 107.6 ?
C12B C13B C15B . . 111.2(7) ?
C12B C13B C14B . . 109.3(7) ?
C15B C13B C14B . . 109.9(7) ?
C12B C13B H132 . . 108.8 ?
C15B C13B H132 . . 108.8 ?
C14B C13B H132 . . 108.8 ?
C13B C14B H144 . . 109.5 ?
C13B C14B H145 . . 109.5 ?
H144 C14B H145 . . 109.5 ?
C13B C14B H146 . . 109.5 ?
H144 C14B H146 . . 109.5 ?
H145 C14B H146 . . 109.5 ?
C13B C15B H154 . . 109.5 ?
C13B C15B H155 . . 109.5 ?
H154 C15B H155 . . 109.5 ?
C13B C15B H156 . . 109.5 ?
H154 C15B H156 . . 109.5 ?
H155 C15B H156 . . 109.5 ?
N2 C21 C22 . . 110.9(5) ?
N2 C21 H211 . . 109.5 ?
C22 C21 H211 . . 109.5 ?
N2 C21 H212 . . 109.5 ?
C22 C21 H212 . . 109.5 ?
H211 C21 H212 . . 108.0 ?
C21 C22 H223 . . 109.5 ?
C21 C22 H222 . . 109.5 ?
H223 C22 H222 . . 109.5 ?
C21 C22 H221 . . 109.5 ?
H223 C22 H221 . . 109.5 ?
H222 C22 H221 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . -2.0(9) ?
C2 N1 C1 C11A . . . . -178.7(5) ?
C21 N2 C2 O2 . . . . 1.0(7) ?
C21 N2 C2 N1 . . . . -178.6(5) ?
C1 N1 C2 O2 . . . . -176.5(5) ?
C1 N1 C2 N2 . . . . 3.1(8) ?
O1 C1 C11A C12A . . . . 51.0(7) ?
N1 C1 C11A C12A . . . . -132.3(6) ?
C1 C11A C12A C13A . . . . 81.4(10) ?
C11A C12A C13A C15A . . . . 60.1(16) ?
C11A C12A C13A C14A . . . . -177.4(11) ?
C2 N2 C21 C22 . . . . -86.2(6) ?
C2 N1 C1 C11B . . . . -178.7(5) ?
O1 C1 C11B C12B . . . . 106.2(9) ?
N1 C1 C11B C12B . . . . -77.1(8) ?
C1 C11B C12B C13B . . . . -148.3(10) ?
C11B C12B C13B C15B . . . . -40.8(18) ?
C11B C12B C13B C14B . . . . 80.6(18) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O1 2_665 0.86 2.40 3.107(5) 139.2
N1 H11 O2 2_566 0.86 2.00 2.862(5) 177.5
data_propyl98K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-(4-methylpentanoyl)-3-propylurea
;
_chemical_name_common ?
_chemical_formula_moiety 'C10 H20 N2 O2'
_chemical_formula_sum 'C10 H20 N2 O2'
_chemical_formula_weight 200.28
_chemical_melting_point 381
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.5437(19)
_cell_length_b 13.205(4)
_cell_length_c 4.8457(13)
_cell_angle_alpha 92.029(14)
_cell_angle_beta 98.767(9)
_cell_angle_gamma 78.875(17)
_cell_volume 592.2(3)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 3224
_cell_measurement_theta_min 2.45
_cell_measurement_theta_max 27.48
_cell_measurement_temperature 98
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 0.50
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.123
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 220
_exptl_absorpt_coefficient_mu 0.078
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 98
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 6949
_diffrn_reflns_av_R_equivalents 0.051
_diffrn_reflns_av_sigmaI/netI 0.0282
_diffrn_reflns_theta_min 2.20
_diffrn_reflns_theta_max 27.47
_diffrn_reflns_theta_full 27.47
_diffrn_measured_fraction_theta_max 0.797
_diffrn_measured_fraction_theta_full 0.797
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 2162
_reflns_number_gt 1775
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0772
_refine_ls_R_factor_gt 0.0619
_refine_ls_wR_factor_gt 0.1534
_refine_ls_wR_factor_ref 0.1677
_refine_ls_goodness_of_fit_ref 1.059
_refine_ls_restrained_S_all 1.059
_refine_ls_number_reflns 2162
_refine_ls_number_parameters 207
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment refall
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+0.7784P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.308
_refine_diff_density_min -0.251
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution 'SIR-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.11921(18) 0.55649(14) -0.0569(4) 0.0314(4) Uani d . 1 . . O
O2 0.40312(18) 0.41157(13) 0.6112(3) 0.0297(4) Uani d . 1 . . O
N1 0.3321(2) 0.52101(15) 0.2434(4) 0.0245(4) Uani d . 1 . . N
H11 0.422(4) 0.542(2) 0.292(6) 0.042(8) Uiso d . 1 . . H
N2 0.1782(2) 0.41817(16) 0.3633(4) 0.0271(5) Uani d . 1 . . N
H21 0.115(4) 0.445(2) 0.224(7) 0.041(8) Uiso d . 1 . . H
C1 0.2423(2) 0.57155(18) 0.0234(5) 0.0248(5) Uani d . 1 . . C
C2 0.3061(2) 0.44630(17) 0.4180(5) 0.0246(5) Uani d . 1 . . C
C11 0.3039(3) 0.65149(18) -0.1090(5) 0.0252(5) Uani d . 1 . . C
H111 0.414(3) 0.626(2) -0.111(6) 0.042(8) Uiso d . 1 . . H
H112 0.255(3) 0.662(2) -0.304(6) 0.029(7) Uiso d . 1 . . H
C12 0.2811(3) 0.75336(19) 0.0561(5) 0.0296(5) Uani d . 1 . . C
H121 0.336(3) 0.744(2) 0.247(6) 0.034(7) Uiso d . 1 . . H
H122 0.174(4) 0.773(2) 0.079(7) 0.049(9) Uiso d . 1 . . H
C13 0.3259(3) 0.84217(19) -0.0817(6) 0.0318(6) Uani d . 1 . . C
H131 0.268(3) 0.851(2) -0.267(6) 0.037(8) Uiso d . 1 . . H
C14 0.2853(4) 0.9422(2) 0.0804(8) 0.0484(8) Uani d . 1 . . C
H141 0.177(4) 0.960(3) 0.084(7) 0.059(10) Uiso d . 1 . . H
H142 0.308(4) 1.002(3) -0.020(8) 0.064(11) Uiso d . 1 . . H
H143 0.336(4) 0.935(3) 0.277(9) 0.070(11) Uiso d . 1 . . H
C15 0.4853(3) 0.8202(3) -0.1093(8) 0.0471(8) Uani d . 1 . . C
H151 0.512(5) 0.880(3) -0.185(8) 0.079(13) Uiso d . 1 . . H
H152 0.539(4) 0.809(3) 0.077(7) 0.051(10) Uiso d . 1 . . H
H153 0.510(4) 0.755(3) -0.239(7) 0.061(10) Uiso d . 1 . . H
C21 0.1370(3) 0.34246(19) 0.5315(5) 0.0270(5) Uani d . 1 . . C
H211 0.204(3) 0.333(2) 0.707(6) 0.032(7) Uiso d . 1 . . H
H212 0.037(3) 0.369(2) 0.581(6) 0.032(7) Uiso d . 1 . . H
C22 0.1387(3) 0.2395(2) 0.3795(6) 0.0338(6) Uani d . 1 . . C
H221 0.241(4) 0.210(2) 0.341(7) 0.045(8) Uiso d . 1 . . H
H222 0.080(4) 0.252(3) 0.189(7) 0.057(10) Uiso d . 1 . . H
C23 0.0812(4) 0.1644(2) 0.5410(7) 0.0403(7) Uani d . 1 . . C
H231 0.136(4) 0.153(3) 0.729(7) 0.049(9) Uiso d . 1 . . H
H232 0.084(4) 0.096(3) 0.456(7) 0.063(11) Uiso d . 1 . . H
H233 -0.019(4) 0.195(3) 0.572(7) 0.053(10) Uiso d . 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0236(9) 0.0398(10) 0.0299(9) -0.0107(7) -0.0062(7) 0.0047(7)
O2 0.0252(9) 0.0352(9) 0.0268(9) -0.0087(7) -0.0067(7) 0.0045(7)
N1 0.0221(10) 0.0286(10) 0.0233(10) -0.0094(8) -0.0014(8) 0.0010(7)
N2 0.0236(11) 0.0332(11) 0.0244(10) -0.0108(8) -0.0041(8) 0.0038(8)
C1 0.0228(12) 0.0285(12) 0.0220(11) -0.0052(9) 0.0005(9) -0.0030(9)
C2 0.0241(12) 0.0287(11) 0.0207(11) -0.0082(9) -0.0010(9) -0.0036(8)
C11 0.0259(12) 0.0287(11) 0.0209(11) -0.0068(9) 0.0002(9) 0.0006(8)
C12 0.0344(14) 0.0294(12) 0.0263(12) -0.0087(10) 0.0061(10) -0.0019(9)
C13 0.0337(14) 0.0298(13) 0.0320(13) -0.0092(10) 0.0008(11) 0.0021(10)
C14 0.062(2) 0.0305(15) 0.0533(19) -0.0095(14) 0.0100(17) -0.0029(13)
C15 0.0377(17) 0.0450(17) 0.064(2) -0.0187(13) 0.0093(15) 0.0040(15)
C21 0.0249(12) 0.0323(12) 0.0243(11) -0.0099(9) -0.0009(10) 0.0029(9)
C22 0.0367(15) 0.0318(13) 0.0360(14) -0.0095(11) 0.0122(12) -0.0016(10)
C23 0.0489(18) 0.0333(14) 0.0438(17) -0.0143(12) 0.0148(14) -0.0007(12)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.231(3) ?
O2 C2 . 1.244(3) ?
N1 C1 . 1.367(3) ?
N1 C2 . 1.403(3) ?
N1 H11 . 0.95(3) ?
N2 C2 . 1.329(3) ?
N2 C21 . 1.458(3) ?
N2 H21 . 0.87(3) ?
C1 C11 . 1.508(3) ?
C11 C12 . 1.537(3) ?
C11 H111 . 1.04(3) ?
C11 H112 . 0.99(3) ?
C12 C13 . 1.530(3) ?
C12 H121 . 0.99(3) ?
C12 H122 . 1.03(3) ?
C13 C15 . 1.518(4) ?
C13 C14 . 1.528(4) ?
C13 H131 . 0.98(3) ?
C14 H141 . 1.01(4) ?
C14 H142 . 1.02(4) ?
C14 H143 . 1.00(4) ?
C15 H151 . 0.97(4) ?
C15 H152 . 0.97(4) ?
C15 H153 . 1.06(4) ?
C21 C22 . 1.522(4) ?
C21 H211 . 0.98(3) ?
C21 H212 . 1.01(3) ?
C22 C23 . 1.515(4) ?
C22 H221 . 1.03(3) ?
C22 H222 . 1.00(4) ?
C23 H231 . 0.98(3) ?
C23 H232 . 0.98(4) ?
C23 H233 . 1.00(4) ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 128.9(2) ?
C1 N1 H11 . . 116.0(18) ?
C2 N1 H11 . . 115.0(18) ?
C2 N2 C21 . . 122.3(2) ?
C2 N2 H21 . . 120(2) ?
C21 N2 H21 . . 117(2) ?
O1 C1 N1 . . 123.6(2) ?
O1 C1 C11 . . 122.0(2) ?
N1 C1 C11 . . 114.4(2) ?
O2 C2 N2 . . 125.0(2) ?
O2 C2 N1 . . 118.1(2) ?
N2 C2 N1 . . 116.9(2) ?
C1 C11 C12 . . 110.1(2) ?
C1 C11 H111 . . 110.4(17) ?
C12 C11 H111 . . 108.8(17) ?
C1 C11 H112 . . 108.5(15) ?
C12 C11 H112 . . 110.3(16) ?
H111 C11 H112 . . 109(2) ?
C13 C12 C11 . . 113.5(2) ?
C13 C12 H121 . . 108.4(16) ?
C11 C12 H121 . . 110.0(16) ?
C13 C12 H122 . . 109.8(18) ?
C11 C12 H122 . . 108.3(18) ?
H121 C12 H122 . . 107(2) ?
C15 C13 C14 . . 111.3(3) ?
C15 C13 C12 . . 112.3(2) ?
C14 C13 C12 . . 109.7(2) ?
C15 C13 H131 . . 109.7(17) ?
C14 C13 H131 . . 107.0(17) ?
C12 C13 H131 . . 106.6(17) ?
C13 C14 H141 . . 111(2) ?
C13 C14 H142 . . 110(2) ?
H141 C14 H142 . . 105(3) ?
C13 C14 H143 . . 110(2) ?
H141 C14 H143 . . 109(3) ?
H142 C14 H143 . . 113(3) ?
C13 C15 H151 . . 110(3) ?
C13 C15 H152 . . 107(2) ?
H151 C15 H152 . . 108(3) ?
C13 C15 H153 . . 111(2) ?
H151 C15 H153 . . 110(3) ?
H152 C15 H153 . . 111(3) ?
N2 C21 C22 . . 111.7(2) ?
N2 C21 H211 . . 108.6(16) ?
C22 C21 H211 . . 110.1(16) ?
N2 C21 H212 . . 110.0(16) ?
C22 C21 H212 . . 109.3(16) ?
H211 C21 H212 . . 107(2) ?
C23 C22 C21 . . 111.7(2) ?
C23 C22 H221 . . 111.5(17) ?
C21 C22 H221 . . 109.3(17) ?
C23 C22 H222 . . 111(2) ?
C21 C22 H222 . . 109(2) ?
H221 C22 H222 . . 104(3) ?
C22 C23 H231 . . 111.7(19) ?
C22 C23 H232 . . 115(2) ?
H231 C23 H232 . . 106(3) ?
C22 C23 H233 . . 109.7(19) ?
H231 C23 H233 . . 104(3) ?
H232 C23 H233 . . 110(3) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . -0.7(4) ?
C2 N1 C1 C11 . . . . 177.0(2) ?
C21 N2 C2 O2 . . . . 0.8(4) ?
C21 N2 C2 N1 . . . . -179.1(2) ?
C1 N1 C2 O2 . . . . -178.6(2) ?
C1 N1 C2 N2 . . . . 1.3(4) ?
O1 C1 C11 C12 . . . . 94.6(3) ?
N1 C1 C11 C12 . . . . -83.1(3) ?
C1 C11 C12 C13 . . . . -173.8(2) ?
C11 C12 C13 C15 . . . . -61.3(3) ?
C11 C12 C13 C14 . . . . 174.3(2) ?
C2 N2 C21 C22 . . . . -106.1(3) ?
N2 C21 C22 C23 . . . . -174.1(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H11 O2 2_666 0.95(3) 1.88(3) 2.820(3) 178(3)
N2 H21 O1 2_565 0.87(3) 2.26(3) 2.959(3) 137(3)
data_propyl298K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-(4-methylpentanoyl)-3-propylurea
;
_chemical_name_common ?
_chemical_formula_moiety 'C10 H20 N2 O2'
_chemical_formula_sum 'C10 H20 N2 O2'
_chemical_formula_weight 200.28
_chemical_melting_point 381
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.547(4)
_cell_length_b 13.688(6)
_cell_length_c 5.1166(16)
_cell_angle_alpha 90.902(14)
_cell_angle_beta 97.109(8)
_cell_angle_gamma 80.47(2)
_cell_volume 654.3(4)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 3480
_cell_measurement_theta_min 1.51
_cell_measurement_theta_max 27.23
_cell_measurement_temperature 298
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 0.50
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.017
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 220
_exptl_absorpt_coefficient_mu 0.071
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 298
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 10255
_diffrn_reflns_av_R_equivalents 0.071
_diffrn_reflns_av_sigmaI/netI 0.0579
_diffrn_reflns_theta_min 2.18
_diffrn_reflns_theta_max 27.48
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measured_fraction_theta_full 0.827
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 6
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 2485
_reflns_number_gt 1178
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1872
_refine_ls_R_factor_gt 0.1166
_refine_ls_wR_factor_gt 0.3131
_refine_ls_wR_factor_ref 0.3767
_refine_ls_goodness_of_fit_ref 1.972
_refine_ls_restrained_S_all 1.975
_refine_ls_number_reflns 2485
_refine_ls_number_parameters 127
_refine_ls_number_restraints 6
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.335
_refine_diff_density_min -0.319
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 98K was used as an initial model.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.1236(3) 0.5584(3) -0.0332(6) 0.1050(12) Uani d . 1 . . O
O2 0.3975(3) 0.4154(2) 0.5961(6) 0.0975(11) Uani d . 1 . . O
N1 0.3307(3) 0.5232(2) 0.2512(6) 0.0836(11) Uani d . 1 . . N
H11 0.4137 0.5401 0.2863 0.100 Uiso calc R 1 . . H
N2 0.1742(3) 0.4212(3) 0.3621(7) 0.0911(12) Uani d . 1 . . N
H21 0.1154 0.4484 0.2325 0.109 Uiso calc R 1 . . H
C1 0.2437(4) 0.5731(3) 0.0441(8) 0.0811(11) Uani d . 1 . . C
C2 0.3029(4) 0.4485(3) 0.4130(8) 0.0808(11) Uani d . 1 . . C
C11 0.3108(4) 0.6517(3) -0.0726(8) 0.0900(13) Uani d D 1 . . C
H111 0.2751 0.6597 -0.2582 0.108 Uiso calc R 1 . . H
H112 0.4137 0.6310 -0.0575 0.108 Uiso calc R 1 . . H
C12 0.2772(5) 0.7513(3) 0.0675(10) 0.1093(16) Uani d D 1 . . C
H121 0.1747 0.7661 0.0737 0.131 Uiso calc R 1 . . H
H122 0.3230 0.7439 0.2478 0.131 Uiso calc R 1 . . H
C13 0.3234(6) 0.8397(3) -0.0551(13) 0.134(2) Uani d D 1 . . C
H131 0.2810 0.8447 -0.2399 0.160 Uiso calc R 1 . . H
C14 0.2702(10) 0.9370(4) 0.0806(19) 0.217(5) Uani d D 1 . . C
H141 0.1681 0.9456 0.0758 0.261 Uiso calc R 1 . . H
H143 0.2956 0.9914 -0.0094 0.261 Uiso calc R 1 . . H
H142 0.3137 0.9351 0.2604 0.261 Uiso calc R 1 . . H
C15 0.4856(6) 0.8229(6) -0.049(2) 0.209(4) Uani d D 1 . . C
H151 0.5138 0.8783 -0.1293 0.251 Uiso calc R 1 . . H
H152 0.5156 0.7636 -0.1440 0.251 Uiso calc R 1 . . H
H153 0.5297 0.8161 0.1304 0.251 Uiso calc R 1 . . H
C21 0.1313(4) 0.3472(3) 0.5193(8) 0.0930(14) Uani d D 1 . . C
H211 0.0317 0.3671 0.5449 0.112 Uiso calc R 1 . . H
H212 0.1878 0.3433 0.6910 0.112 Uiso calc R 1 . . H
C22 0.1503(6) 0.2446(3) 0.3913(11) 0.1219(18) Uani d D 1 . . C
H221 0.0991 0.2492 0.2148 0.146 Uiso calc R 1 . . H
H222 0.2510 0.2224 0.3769 0.146 Uiso calc R 1 . . H
C23 0.0952(7) 0.1689(4) 0.5501(15) 0.150(2) Uani d D 1 . . C
H232 0.1068 0.1061 0.4624 0.180 Uiso calc R 1 . . H
H231 -0.0043 0.1908 0.5653 0.180 Uiso calc R 1 . . H
H233 0.1485 0.1622 0.7225 0.180 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0711(15) 0.133(3) 0.109(2) -0.0320(15) -0.0182(15) 0.031(2)
O2 0.0768(16) 0.109(2) 0.104(2) -0.0281(15) -0.0173(16) 0.0273(17)
N1 0.0662(16) 0.100(3) 0.085(2) -0.0257(16) -0.0085(15) 0.0091(18)
N2 0.0703(17) 0.112(3) 0.093(2) -0.0310(17) -0.0100(16) 0.0215(19)
C1 0.0654(17) 0.098(3) 0.080(2) -0.0186(18) -0.0014(17) 0.002(2)
C2 0.0667(19) 0.091(3) 0.085(2) -0.0214(18) -0.0011(19) 0.006(2)
C11 0.087(2) 0.099(3) 0.086(2) -0.019(2) 0.011(2) 0.009(2)
C12 0.111(3) 0.100(4) 0.124(4) -0.023(3) 0.036(3) 0.007(3)
C13 0.147(5) 0.102(4) 0.160(5) -0.031(3) 0.037(4) 0.018(4)
C14 0.271(12) 0.101(5) 0.298(11) -0.032(6) 0.105(10) 0.005(6)
C15 0.153(6) 0.157(6) 0.347(13) -0.075(5) 0.080(8) 0.006(8)
C21 0.080(2) 0.105(3) 0.096(3) -0.027(2) 0.003(2) 0.017(3)
C22 0.122(4) 0.106(4) 0.144(4) -0.024(3) 0.035(4) 0.006(3)
C23 0.165(6) 0.110(4) 0.183(6) -0.029(4) 0.045(5) 0.016(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.213(5) ?
O2 C2 . 1.252(4) ?
N1 C1 . 1.377(5) ?
N1 C2 . 1.404(6) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.337(5) ?
N2 C21 . 1.444(6) ?
N2 H21 . 0.8600 ?
C1 C11 . 1.506(6) ?
C11 C12 . 1.534(6) ?
C11 H111 . 0.9700 ?
C11 H112 . 0.9700 ?
C12 C13 . 1.524(7) ?
C12 H121 . 0.9700 ?
C12 H122 . 0.9700 ?
C13 C15 . 1.524(8) ?
C13 C14 . 1.532(9) ?
C13 H131 . 0.9800 ?
C14 H141 . 0.9600 ?
C14 H143 . 0.9600 ?
C14 H142 . 0.9600 ?
C15 H151 . 0.9600 ?
C15 H152 . 0.9600 ?
C15 H153 . 0.9600 ?
C21 C22 . 1.533(6) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 C23 . 1.524(9) ?
C22 H221 . 0.9700 ?
C22 H222 . 0.9700 ?
C23 H232 . 0.9600 ?
C23 H231 . 0.9600 ?
C23 H233 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 129.2(3) ?
C1 N1 H11 . . 115.4 ?
C2 N1 H11 . . 115.4 ?
C2 N2 C21 . . 121.7(3) ?
C2 N2 H21 . . 119.2 ?
C21 N2 H21 . . 119.2 ?
O1 C1 N1 . . 124.3(4) ?
O1 C1 C11 . . 122.7(4) ?
N1 C1 C11 . . 112.9(3) ?
O2 C2 N2 . . 125.5(4) ?
O2 C2 N1 . . 118.1(3) ?
N2 C2 N1 . . 116.4(3) ?
C1 C11 C12 . . 111.3(3) ?
C1 C11 H111 . . 109.4 ?
C12 C11 H111 . . 109.4 ?
C1 C11 H112 . . 109.4 ?
C12 C11 H112 . . 109.4 ?
H111 C11 H112 . . 108.0 ?
C13 C12 C11 . . 116.1(4) ?
C13 C12 H121 . . 108.3 ?
C11 C12 H121 . . 108.3 ?
C13 C12 H122 . . 108.3 ?
C11 C12 H122 . . 108.3 ?
H121 C12 H122 . . 107.4 ?
C12 C13 C15 . . 109.9(4) ?
C12 C13 C14 . . 111.9(4) ?
C15 C13 C14 . . 111.1(6) ?
C12 C13 H131 . . 107.9 ?
C15 C13 H131 . . 107.9 ?
C14 C13 H131 . . 107.9 ?
C13 C14 H141 . . 109.5 ?
C13 C14 H143 . . 109.5 ?
H141 C14 H143 . . 109.5 ?
C13 C14 H142 . . 109.5 ?
H141 C14 H142 . . 109.5 ?
H143 C14 H142 . . 109.5 ?
C13 C15 H151 . . 109.5 ?
C13 C15 H152 . . 109.5 ?
H151 C15 H152 . . 109.5 ?
C13 C15 H153 . . 109.5 ?
H151 C15 H153 . . 109.5 ?
H152 C15 H153 . . 109.5 ?
N2 C21 C22 . . 112.4(3) ?
N2 C21 H211 . . 109.1 ?
C22 C21 H211 . . 109.1 ?
N2 C21 H212 . . 109.1 ?
C22 C21 H212 . . 109.1 ?
H211 C21 H212 . . 107.9 ?
C23 C22 C21 . . 111.7(4) ?
C23 C22 H221 . . 109.3 ?
C21 C22 H221 . . 109.3 ?
C23 C22 H222 . . 109.3 ?
C21 C22 H222 . . 109.3 ?
H221 C22 H222 . . 107.9 ?
C22 C23 H232 . . 109.5 ?
C22 C23 H231 . . 109.5 ?
H232 C23 H231 . . 109.5 ?
C22 C23 H233 . . 109.5 ?
H232 C23 H233 . . 109.5 ?
H231 C23 H233 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . -0.4(7) ?
C2 N1 C1 C11 . . . . 177.4(4) ?
C21 N2 C2 O2 . . . . -0.5(7) ?
C21 N2 C2 N1 . . . . -178.3(4) ?
C1 N1 C2 O2 . . . . -178.0(4) ?
C1 N1 C2 N2 . . . . -0.1(6) ?
O1 C1 C11 C12 . . . . 89.0(5) ?
N1 C1 C11 C12 . . . . -88.8(5) ?
C1 C11 C12 C13 . . . . -172.6(4) ?
C11 C12 C13 C15 . . . . -62.5(8) ?
C11 C12 C13 C14 . . . . 173.6(6) ?
C2 N2 C21 C22 . . . . -98.4(5) ?
N2 C21 C22 C23 . . . . -176.1(5) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H11 O2 2_666 0.86 2.02 2.873(4) 174.2
N2 H21 O1 2_565 0.86 2.40 3.092(4) 138.2
data_propyl348K
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-(4-methylpentanoyl)-3-propylurea
;
_chemical_name_common ?
_chemical_formula_moiety 'C10 H20 N2 O2'
_chemical_formula_sum 'C10 H20 N2 O2'
_chemical_formula_weight 200.28
_chemical_melting_point 381
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.405(2)
_cell_length_b 13.3600(19)
_cell_length_c 5.1686(8)
_cell_angle_alpha 93.609(13)
_cell_angle_beta 98.144(12)
_cell_angle_gamma 79.387(10)
_cell_volume 631.46(19)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 1956
_cell_measurement_theta_min 2.215
_cell_measurement_theta_max 25.73
_cell_measurement_temperature 348
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 0.50
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.053
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 220
_exptl_absorpt_coefficient_mu 0.073
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 348
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'RIGAKU RAXIS-RAPID'
_diffrn_measurement_method 'Oscillation method'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number 10152
_diffrn_reflns_av_R_equivalents 0.078
_diffrn_reflns_av_sigmaI/netI 0.0527
_diffrn_reflns_theta_min 2.22
_diffrn_reflns_theta_max 27.48
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_max 0.543
_diffrn_measured_fraction_theta_full 0.543
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_limit_l_max 5
_diffrn_standards_number 0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 1576
_reflns_number_gt 861
_reflns_threshold_expression >2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.2108
_refine_ls_R_factor_gt 0.1401
_refine_ls_wR_factor_gt 0.3401
_refine_ls_wR_factor_ref 0.3910
_refine_ls_goodness_of_fit_ref 2.045
_refine_ls_restrained_S_all 2.046
_refine_ls_number_reflns 1576
_refine_ls_number_parameters 127
_refine_ls_number_restraints 6
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.229
_refine_diff_density_min -0.183
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_structure_solution
;
The final structure at 298K was used as an initial model.
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.1244(5) 0.5604(4) -0.0247(11) 0.123(2) Uani d . 1 . . O
O2 0.3953(5) 0.4151(4) 0.5898(11) 0.118(2) Uani d . 1 . . O
N1 0.3332(5) 0.5239(4) 0.2559(12) 0.0920(18) Uani d . 1 . . N
H11 0.4181 0.5404 0.2946 0.110 Uiso calc R 1 . . H
N2 0.1729(6) 0.4231(4) 0.3557(12) 0.105(2) Uani d . 1 . . N
H21 0.1135 0.4495 0.2256 0.126 Uiso calc R 1 . . H
C1 0.2465(7) 0.5732(5) 0.0567(14) 0.089(2) Uani d . 1 . . C
C2 0.3033(7) 0.4487(5) 0.4096(16) 0.095(2) Uani d . 1 . . C
C11 0.3133(8) 0.6498(5) -0.0617(16) 0.110(2) Uani d D 1 . . C
H111 0.2753 0.6552 -0.2458 0.132 Uiso calc R 1 . . H
H112 0.4183 0.6279 -0.0472 0.132 Uiso calc R 1 . . H
C12 0.2778(9) 0.7532(5) 0.0799(19) 0.138(3) Uani d D 1 . . C
H121 0.3301 0.7499 0.2558 0.166 Uiso calc R 1 . . H
H122 0.1741 0.7682 0.0937 0.166 Uiso calc R 1 . . H
C13 0.3184(12) 0.8392(6) -0.060(2) 0.170(4) Uani d D 1 . . C
H131 0.2765 0.8399 -0.2447 0.204 Uiso calc R 1 . . H
C14 0.267(2) 0.9396(8) 0.084(4) 0.308(11) Uani d D 1 . . C
H141 0.1620 0.9515 0.0729 0.370 Uiso calc R 1 . . H
H142 0.2964 0.9943 0.0063 0.370 Uiso calc R 1 . . H
H143 0.3085 0.9361 0.2648 0.370 Uiso calc R 1 . . H
C15 0.4845(12) 0.8228(9) -0.028(3) 0.266(9) Uani d D 1 . . C
H151 0.5149 0.8774 -0.1057 0.319 Uiso calc R 1 . . H
H152 0.5213 0.7592 -0.1127 0.319 Uiso calc R 1 . . H
H153 0.5220 0.8215 0.1548 0.319 Uiso calc R 1 . . H
C21 0.1277(8) 0.3497(5) 0.5162(16) 0.118(3) Uani d D 1 . . C
H211 0.0241 0.3686 0.5281 0.141 Uiso calc R 1 . . H
H212 0.1800 0.3513 0.6917 0.141 Uiso calc R 1 . . H
C22 0.1598(12) 0.2423(5) 0.393(2) 0.162(4) Uani d D 1 . . C
H221 0.2640 0.2210 0.3921 0.194 Uiso calc R 1 . . H
H222 0.1121 0.2410 0.2142 0.194 Uiso calc R 1 . . H
C23 0.1023(15) 0.1705(7) 0.556(2) 0.192(5) Uani d D 1 . . C
H231 0.1530 0.1702 0.7306 0.231 Uiso calc R 1 . . H
H232 0.1181 0.1028 0.4782 0.231 Uiso calc R 1 . . H
H233 -0.0003 0.1935 0.5604 0.231 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.079(3) 0.154(5) 0.132(4) -0.029(3) -0.020(3) 0.023(3)
O2 0.090(3) 0.129(4) 0.131(4) -0.038(3) -0.031(3) 0.030(3)
N1 0.068(3) 0.103(4) 0.106(4) -0.030(3) -0.005(3) 0.007(4)
N2 0.079(3) 0.118(4) 0.122(5) -0.039(3) -0.009(3) 0.022(4)
C1 0.068(4) 0.106(5) 0.088(5) -0.014(3) -0.007(4) 0.007(4)
C2 0.067(4) 0.101(5) 0.114(6) -0.024(4) -0.007(4) -0.006(4)
C11 0.102(5) 0.121(6) 0.110(6) -0.028(4) 0.013(5) 0.005(5)
C12 0.121(6) 0.128(7) 0.180(9) -0.039(5) 0.049(6) 0.001(7)
C13 0.173(10) 0.123(7) 0.227(13) -0.043(7) 0.048(9) 0.006(8)
C14 0.39(2) 0.117(9) 0.46(3) -0.067(11) 0.16(2) 0.018(13)
C15 0.194(14) 0.175(11) 0.46(3) -0.078(10) 0.069(16) 0.046(15)
C21 0.081(4) 0.150(7) 0.122(6) -0.037(4) -0.004(4) 0.001(6)
C22 0.195(10) 0.124(7) 0.181(11) -0.063(7) 0.036(9) -0.015(8)
C23 0.255(14) 0.126(7) 0.216(13) -0.063(8) 0.062(11) 0.011(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.206(8) ?
O2 C2 . 1.224(9) ?
N1 C1 . 1.345(8) ?
N1 C2 . 1.410(10) ?
N1 H11 . 0.8600 ?
N2 C2 . 1.320(9) ?
N2 C21 . 1.479(11) ?
N2 H21 . 0.8600 ?
C1 C11 . 1.496(11) ?
C11 C12 . 1.526(10) ?
C11 H111 . 0.9700 ?
C11 H112 . 0.9700 ?
C12 C13 . 1.528(14) ?
C12 H121 . 0.9700 ?
C12 H122 . 0.9700 ?
C13 C15 . 1.524(15) ?
C13 C14 . 1.526(16) ?
C13 H131 . 0.9800 ?
C14 H141 . 0.9600 ?
C14 H142 . 0.9600 ?
C14 H143 . 0.9600 ?
C15 H151 . 0.9600 ?
C15 H152 . 0.9600 ?
C15 H153 . 0.9600 ?
C21 C22 . 1.528(10) ?
C21 H211 . 0.9700 ?
C21 H212 . 0.9700 ?
C22 C23 . 1.529(17) ?
C22 H221 . 0.9700 ?
C22 H222 . 0.9700 ?
C23 H231 . 0.9600 ?
C23 H232 . 0.9600 ?
C23 H233 . 0.9600 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 128.5(5) ?
C1 N1 H11 . . 115.7 ?
C2 N1 H11 . . 115.7 ?
C2 N2 C21 . . 120.9(7) ?
C2 N2 H21 . . 119.6 ?
C21 N2 H21 . . 119.6 ?
O1 C1 N1 . . 125.1(7) ?
O1 C1 C11 . . 120.6(7) ?
N1 C1 C11 . . 114.3(6) ?
O2 C2 N2 . . 124.4(8) ?
O2 C2 N1 . . 118.8(6) ?
N2 C2 N1 . . 116.8(7) ?
C1 C11 C12 . . 109.5(6) ?
C1 C11 H111 . . 109.8 ?
C12 C11 H111 . . 109.8 ?
C1 C11 H112 . . 109.8 ?
C12 C11 H112 . . 109.8 ?
H111 C11 H112 . . 108.2 ?
C11 C12 C13 . . 112.5(7) ?
C11 C12 H121 . . 109.1 ?
C13 C12 H121 . . 109.1 ?
C11 C12 H122 . . 109.1 ?
C13 C12 H122 . . 109.1 ?
H121 C12 H122 . . 107.8 ?
C15 C13 C14 . . 107.1(11) ?
C15 C13 C12 . . 106.7(7) ?
C14 C13 C12 . . 108.1(7) ?
C15 C13 H131 . . 111.6 ?
C14 C13 H131 . . 111.6 ?
C12 C13 H131 . . 111.6 ?
C13 C14 H141 . . 109.5 ?
C13 C14 H142 . . 109.5 ?
H141 C14 H142 . . 109.5 ?
C13 C14 H143 . . 109.5 ?
H141 C14 H143 . . 109.5 ?
H142 C14 H143 . . 109.5 ?
C13 C15 H151 . . 109.5 ?
C13 C15 H152 . . 109.5 ?
H151 C15 H152 . . 109.5 ?
C13 C15 H153 . . 109.5 ?
H151 C15 H153 . . 109.5 ?
H152 C15 H153 . . 109.5 ?
N2 C21 C22 . . 110.0(6) ?
N2 C21 H211 . . 109.7 ?
C22 C21 H211 . . 109.7 ?
N2 C21 H212 . . 109.7 ?
C22 C21 H212 . . 109.7 ?
H211 C21 H212 . . 108.2 ?
C21 C22 C23 . . 108.0(7) ?
C21 C22 H221 . . 110.1 ?
C23 C22 H221 . . 110.1 ?
C21 C22 H222 . . 110.1 ?
C23 C22 H222 . . 110.1 ?
H221 C22 H222 . . 108.4 ?
C22 C23 H231 . . 109.5 ?
C22 C23 H232 . . 109.5 ?
H231 C23 H232 . . 109.5 ?
C22 C23 H233 . . 109.5 ?
H231 C23 H233 . . 109.5 ?
H232 C23 H233 . . 109.5 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 0.1(11) ?
C2 N1 C1 C11 . . . . 179.4(6) ?
C21 N2 C2 O2 . . . . 0.2(11) ?
C21 N2 C2 N1 . . . . -176.2(6) ?
C1 N1 C2 O2 . . . . -177.4(6) ?
C1 N1 C2 N2 . . . . -0.8(10) ?
O1 C1 C11 C12 . . . . 89.5(9) ?
N1 C1 C11 C12 . . . . -89.8(8) ?
C1 C11 C12 C13 . . . . -169.7(8) ?
C11 C12 C13 C15 . . . . -69.9(11) ?
C11 C12 C13 C14 . . . . 175.2(11) ?
C2 N2 C21 C22 . . . . -93.9(8) ?
N2 C21 C22 C23 . . . . -176.4(8) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H11 O2 2_666 0.86 1.96 2.815(7) 174.8
N2 H21 O1 2_565 0.86 2.35 3.043(8) 137.5
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