#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/47/4024797.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024797
loop_
_publ_author_name
'Guillaume Lessene'
'Brian J. Smith'
'Robert W. Gable'
'Jonathan B. Baell'
_publ_section_title
;
Characterization of the Two Fundamental Conformations of Benzoylureas and
Elucidation of the Factors That Facilitate Their Conformational Interchange
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6511
_journal_page_last               6525
_journal_paper_doi               10.1021/jo900871a
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C15 H22 N2 O2'
_chemical_formula_sum            'C15 H22 N2 O2'
_chemical_formula_weight         262.35
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.918(9)
_cell_angle_beta                 92.653(7)
_cell_angle_gamma                111.225(5)
_cell_formula_units_Z            2
_cell_length_a                   8.6456(5)
_cell_length_b                   9.0647(8)
_cell_length_c                   10.9868(12)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      33.2
_cell_measurement_theta_min      21.2
_cell_volume                     766.22(12)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'PROCESS_DATA (Gable et al. 1993)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4MachS diffractometer'
_diffrn_measurement_method       ω:2θ
_diffrn_radiation_monochromator  'Ni filter'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6185
_diffrn_reflns_theta_full        74.88
_diffrn_reflns_theta_max         74.88
_diffrn_reflns_theta_min         4.22
_diffrn_standards_decay_%        5
_diffrn_standards_interval_time  160
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  0.9716
_exptl_absorpt_correction_T_min  0.8562
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'Sheldrick, 1976 (modified for Intensity)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0294(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0550P)²+0.1275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                2490
_reflns_number_total             3148
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo900871a_si_002.cif
_cod_data_source_block           jb_18
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4024797
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.16148(15) 0.62556(16) 0.21800(12) 0.0422(3) Uani 1 1 d . . .
C2 C 0.17660(19) 0.6621(2) 0.35005(14) 0.0546(4) Uani 1 1 d . . .
C3 C 0.2606(2) 0.8231(2) 0.42565(16) 0.0669(5) Uani 1 1 d . . .
C4 C 0.3291(2) 0.9482(2) 0.37129(17) 0.0662(4) Uani 1 1 d . . .
C5 C 0.3159(2) 0.91338(19) 0.24075(17) 0.0591(4) Uani 1 1 d . . .
C6 C 0.23404(18) 0.75211(18) 0.16433(15) 0.0499(3) Uani 1 1 d . . .
C7 C 0.08476(16) 0.45189(16) 0.13200(12) 0.0422(3) Uani 1 1 d . . .
O1 O 0.14750(13) 0.40843(13) 0.03879(10) 0.0562(3) Uani 1 1 d . . .
N1 N -0.05084(14) 0.34047(13) 0.16508(10) 0.0439(3) Uani 1 1 d . . .
C8 C -0.08123(19) 0.16153(17) 0.11986(15) 0.0519(4) Uani 1 1 d . . .
C9 C -0.2658(2) 0.0509(2) 0.09568(18) 0.0707(5) Uani 1 1 d . . .
H9A H -0.2812 -0.0594 0.0474 0.104(7) Uiso 1 1 calc R . .
H9B H -0.3278 0.0928 0.0486 0.081(6) Uiso 1 1 calc R . .
H9C H -0.3055 0.0490 0.1756 0.087(6) Uiso 1 1 calc R . .
C10 C 0.0185(2) 0.1181(2) 0.2115(2) 0.0741(5) Uani 1 1 d . . .
H10A H -0.0192 0.1362 0.2928 0.087(7) Uiso 1 1 calc R . .
H10B H 0.1355 0.1866 0.2212 0.109(8) Uiso 1 1 calc R . .
H10C H 0.0025 0.0038 0.1787 0.085(6) Uiso 1 1 calc R . .
C11 C -0.15898(17) 0.38813(17) 0.24789(13) 0.0465(3) Uani 1 1 d . . .
O2 O -0.19298(17) 0.33223(16) 0.33672(12) 0.0725(4) Uani 1 1 d . . .
N2 N -0.22025(14) 0.48895(14) 0.21291(12) 0.0457(3) Uani 1 1 d . . .
C12 C -0.32871(19) 0.56183(19) 0.28430(16) 0.0572(4) Uani 1 1 d . . .
C13 C -0.3592(3) 0.6749(3) 0.2152(2) 0.0923(7) Uani 1 1 d . . .
H13A H -0.4195 0.6109 0.1311 0.118(5) Uiso 1 1 calc R . .
H13B H -0.2535 0.7556 0.2090 0.118(5) Uiso 1 1 calc R . .
H13C H -0.4240 0.7302 0.2614 0.118(5) Uiso 1 1 calc R . .
C14 C -0.4952(3) 0.4259(3) 0.2840(3) 0.1076(9) Uani 1 1 d . . .
H14A H -0.4759 0.3514 0.3252 0.140(6) Uiso 1 1 calc R . .
H14B H -0.5490 0.3662 0.1977 0.140(6) Uiso 1 1 calc R . .
H14C H -0.5661 0.4742 0.3289 0.140(6) Uiso 1 1 calc R . .
C15 C -0.2404(4) 0.6590(4) 0.4193(2) 0.1103(9) Uani 1 1 d . . .
H15A H -0.1386 0.7479 0.4174 0.139(6) Uiso 1 1 calc R . .
H15B H -0.2142 0.5871 0.4599 0.139(6) Uiso 1 1 calc R . .
H15C H -0.3125 0.7036 0.4662 0.139(6) Uiso 1 1 calc R . .
H2 H 0.130(2) 0.574(2) 0.3891(16) 0.062(5) Uiso 1 1 d . . .
H3 H 0.269(3) 0.848(2) 0.516(2) 0.090(6) Uiso 1 1 d . . .
H4 H 0.389(3) 1.061(3) 0.4253(19) 0.081(6) Uiso 1 1 d . . .
H5 H 0.362(2) 1.001(2) 0.2010(17) 0.074(5) Uiso 1 1 d . . .
H6 H 0.227(2) 0.7246(19) 0.0735(16) 0.055(4) Uiso 1 1 d . . .
H8 H -0.039(2) 0.152(2) 0.0392(17) 0.067(5) Uiso 1 1 d . . .
H2N H -0.198(2) 0.511(2) 0.1437(16) 0.055(4) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.19(13) . . ?
C6 C1 C7 118.35(12) . . ?
C2 C1 C7 122.16(12) . . ?
C3 C2 C1 119.96(15) . . ?
C3 C2 H2 120.0(10) . . ?
C1 C2 H2 120.1(10) . . ?
C4 C3 C2 120.36(16) . . ?
C4 C3 H3 119.9(12) . . ?
C2 C3 H3 119.7(12) . . ?
C3 C4 C5 120.18(16) . . ?
C3 C4 H4 119.9(11) . . ?
C5 C4 H4 119.9(12) . . ?
C4 C5 C6 119.85(16) . . ?
C4 C5 H5 121.0(11) . . ?
C6 C5 H5 119.2(11) . . ?
C5 C6 C1 120.43(15) . . ?
C5 C6 H6 121.2(9) . . ?
C1 C6 H6 118.3(9) . . ?
O1 C7 N1 121.21(12) . . ?
O1 C7 C1 120.38(12) . . ?
N1 C7 C1 118.28(11) . . ?
C7 N1 C11 123.59(11) . . ?
C7 N1 C8 118.62(11) . . ?
C11 N1 C8 117.67(11) . . ?
N1 C8 C10 110.40(13) . . ?
N1 C8 C9 112.67(13) . . ?
C10 C8 C9 111.69(14) . . ?
N1 C8 H8 102.6(10) . . ?
C10 C8 H8 110.2(10) . . ?
C9 C8 H8 108.9(10) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 N2 125.73(13) . . ?
O2 C11 N1 120.53(12) . . ?
N2 C11 N1 113.66(11) . . ?
C11 N2 C12 124.66(12) . . ?
C11 N2 H2N 117.8(11) . . ?
C12 N2 H2N 117.5(11) . . ?
N2 C12 C13 106.65(13) . . ?
N2 C12 C15 109.66(14) . . ?
C13 C12 C15 110.45(19) . . ?
N2 C12 C14 109.85(14) . . ?
C13 C12 C14 109.25(18) . . ?
C15 C12 C14 110.89(19) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3852(19) . ?
C1 C2 1.391(2) . ?
C1 C7 1.4937(19) . ?
C2 C3 1.378(2) . ?
C2 H2 0.973(18) . ?
C3 C4 1.375(3) . ?
C3 H3 0.95(2) . ?
C4 C5 1.377(2) . ?
C4 H4 0.97(2) . ?
C5 C6 1.381(2) . ?
C5 H5 0.974(19) . ?
C6 H6 0.958(16) . ?
C7 O1 1.2234(15) . ?
C7 N1 1.3776(16) . ?
N1 C11 1.4343(16) . ?
N1 C8 1.4871(17) . ?
C8 C10 1.510(2) . ?
C8 C9 1.512(2) . ?
C8 H8 0.971(17) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O2 1.2121(16) . ?
C11 N2 1.3327(18) . ?
N2 C12 1.4767(17) . ?
N2 H2N 0.846(17) . ?
C12 C13 1.508(2) . ?
C12 C15 1.514(3) . ?
C12 C14 1.517(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2N O1 0.846(17) 2.315(18) 3.1575(16) 174.0(15) 2_565 ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.1(2) . . . . ?
C7 C1 C2 C3 174.68(14) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 1.6(2) . . . . ?
C2 C1 C6 C5 -2.0(2) . . . . ?
C7 C1 C6 C5 -175.84(13) . . . . ?
C6 C1 C7 O1 35.26(18) . . . . ?
C2 C1 C7 O1 -138.39(14) . . . . ?
C6 C1 C7 N1 -148.88(12) . . . . ?
C2 C1 C7 N1 37.47(18) . . . . ?
O1 C7 N1 C11 -161.44(13) . . . . ?
C1 C7 N1 C11 22.73(18) . . . . ?
O1 C7 N1 C8 22.73(19) . . . . ?
C1 C7 N1 C8 -153.10(12) . . . . ?
C7 N1 C8 C10 86.39(16) . . . . ?
C11 N1 C8 C10 -89.68(16) . . . . ?
C7 N1 C8 C9 -147.96(13) . . . . ?
C11 N1 C8 C9 35.96(18) . . . . ?
C7 N1 C11 O2 -130.52(16) . . . . ?
C8 N1 C11 O2 45.3(2) . . . . ?
C7 N1 C11 N2 52.52(18) . . . . ?
C8 N1 C11 N2 -131.61(13) . . . . ?
O2 C11 N2 C12 5.9(2) . . . . ?
N1 C11 N2 C12 -177.34(12) . . . . ?
C11 N2 C12 C13 176.63(16) . . . . ?
C11 N2 C12 C15 57.0(2) . . . . ?
C11 N2 C12 C14 -65.1(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659031
