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#$Date: 2023-06-15 10:57:31 +0300 (Thu, 15 Jun 2023) $
#$Revision: 284474 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107369.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_8107369
loop_
_publ_author_name
'Gao, Kai'
'Zha, Su-E.'
'Liu, Chang-Ying'
'Wang, Qiao-Juan'
'Wang, Er-Qiang'
_publ_section_title
;
 The crystal structure of 1-(4-bromophenyl)-3-cycloheptylurea, C14H19BrN2O
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              117
_journal_page_last               118
_journal_paper_doi               10.1515/ncrs-2022-0486
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C14 H19 Br N2 O'
_chemical_formula_sum            'C14 H19 Br N2 O'
_chemical_formula_weight         311.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 98.214(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9782(8)
_cell_length_b                   9.1447(6)
_cell_length_c                   11.8842(8)
_cell_measurement_reflns_used    3195
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.110
_cell_measurement_theta_min      3.356
_cell_volume                     1395.97(16)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009) [4]'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018) [3]'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018) [2]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6259
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.110
_diffrn_reflns_theta_min         3.356
_diffrn_standards_decay_%        -
_diffrn_standards_interval_count -
_diffrn_standards_interval_time  -
_diffrn_standards_number         -
_exptl_absorpt_coefficient_mu    2.935
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       Block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         3195
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0764P)²+1.2590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1876
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1764
_reflns_number_total             3195
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0486_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107369
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.93111(5) 0.55708(7) 0.66584(5) 0.0780(3) Uani 1 1 d . . . . .
O1 O 0.4812(2) 0.5093(3) 0.2848(3) 0.0467(8) Uani 1 1 d . . . . .
N1 N 0.5693(3) 0.7236(4) 0.3071(3) 0.0482(10) Uani 1 1 d . . . . .
H1 H 0.569925 0.813551 0.286069 0.058 Uiso 1 1 calc R U . . .
N2 N 0.4201(3) 0.7091(4) 0.1839(4) 0.0598(13) Uani 1 1 d . . . . .
H2 H 0.425169 0.802615 0.179387 0.072 Uiso 1 1 calc R U . . .
C1 C 0.8181(4) 0.6020(5) 0.5504(4) 0.0466(11) Uani 1 1 d . . . . .
C2 C 0.7180(4) 0.5717(5) 0.5697(4) 0.0472(12) Uani 1 1 d . . . . .
H2A H 0.706415 0.526000 0.636641 0.057 Uiso 1 1 calc R U . . .
C3 C 0.6356(4) 0.6094(5) 0.4894(4) 0.0446(11) Uani 1 1 d . . . . .
H3 H 0.567939 0.590659 0.502593 0.054 Uiso 1 1 calc R U . . .
C4 C 0.6525(3) 0.6750(4) 0.3892(4) 0.0368(10) Uani 1 1 d . . . . .
C5 C 0.7535(4) 0.7005(5) 0.3702(4) 0.0475(12) Uani 1 1 d . . . . .
H5 H 0.765578 0.742311 0.301989 0.057 Uiso 1 1 calc R U . . .
C6 C 0.8373(4) 0.6644(5) 0.4517(4) 0.0506(12) Uani 1 1 d . . . . .
H6 H 0.905160 0.682569 0.439012 0.061 Uiso 1 1 calc R U . . .
C7 C 0.4892(3) 0.6395(5) 0.2594(4) 0.0375(10) Uani 1 1 d . . . . .
C8 C 0.3362(3) 0.6374(5) 0.1083(4) 0.0452(11) Uani 1 1 d D . . . .
H8 H 0.332020 0.535983 0.133979 0.054 Uiso 1 1 calc R U . . .
C9 C 0.3605(4) 0.6337(6) -0.0123(5) 0.0670(15) Uani 1 1 d D . . . .
H9A H 0.434403 0.615305 -0.009914 0.080 Uiso 1 1 calc R U . . .
H9B H 0.346181 0.729594 -0.045803 0.080 Uiso 1 1 calc R U . . .
C10 C 0.3009(5) 0.5206(7) -0.0899(5) 0.0795(19) Uani 1 1 d D . . . .
H10A H 0.332229 0.517646 -0.159306 0.095 Uiso 1 1 calc R U . . .
H10B H 0.313570 0.426116 -0.053502 0.095 Uiso 1 1 calc R U . . .
C11 C 0.1861(6) 0.5347(10) -0.1239(7) 0.115(2) Uani 1 1 d D . . . .
H11A H 0.174742 0.563075 -0.203332 0.138 Uiso 1 1 calc R U . . .
H11B H 0.156640 0.437659 -0.119741 0.138 Uiso 1 1 calc R U . . .
C12 C 0.1262(6) 0.6301(10) -0.0658(6) 0.115(2) Uani 1 1 d D . . . .
H12A H 0.053913 0.604707 -0.090368 0.138 Uiso 1 1 calc R U . . .
H12B H 0.136009 0.727347 -0.095216 0.138 Uiso 1 1 calc R U . . .
C13 C 0.1377(4) 0.6439(9) 0.0551(5) 0.0892(15) Uani 1 1 d D . . . .
H13A H 0.130907 0.546512 0.085466 0.107 Uiso 1 1 calc R U . . .
H13B H 0.078556 0.699919 0.072692 0.107 Uiso 1 1 calc R U . . .
C14 C 0.2344(4) 0.7117(8) 0.1221(6) 0.0892(15) Uani 1 1 d D . . . .
H14A H 0.238377 0.813089 0.099162 0.107 Uiso 1 1 calc R U . . .
H14B H 0.226613 0.710753 0.202026 0.107 Uiso 1 1 calc R U . . .
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'
Br Br -0.2901 2.4595 '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'
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
C7 N1 C4 125.1(4) . .
C7 N1 H1 117.5 . .
C4 N1 H1 117.5 . .
C7 N2 C8 124.6(4) . .
C7 N2 H2 117.7 . .
C8 N2 H2 117.7 . .
C6 C1 C2 121.4(4) . .
C6 C1 Br1 119.7(4) . .
C2 C1 Br1 118.9(4) . .
C3 C2 C1 119.6(5) . .
C3 C2 H2A 120.2 . .
C1 C2 H2A 120.2 . .
C2 C3 C4 120.4(5) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
C3 C4 C5 119.1(4) . .
C3 C4 N1 122.1(4) . .
C5 C4 N1 118.8(4) . .
C4 C5 C6 120.8(5) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C1 C6 C5 118.7(5) . .
C1 C6 H6 120.6 . .
C5 C6 H6 120.6 . .
O1 C7 N2 123.4(4) . .
O1 C7 N1 122.2(4) . .
N2 C7 N1 114.4(4) . .
N2 C8 C9 110.8(4) . .
N2 C8 C14 108.4(4) . .
C9 C8 C14 114.5(4) . .
N2 C8 H8 107.6 . .
C9 C8 H8 107.6 . .
C14 C8 H8 107.6 . .
C8 C9 C10 115.7(5) . .
C8 C9 H9A 108.4 . .
C10 C9 H9A 108.4 . .
C8 C9 H9B 108.4 . .
C10 C9 H9B 108.4 . .
H9A C9 H9B 107.4 . .
C11 C10 C9 120.4(5) . .
C11 C10 H10A 107.2 . .
C9 C10 H10A 107.2 . .
C11 C10 H10B 107.2 . .
C9 C10 H10B 107.2 . .
H10A C10 H10B 106.9 . .
C12 C11 C10 121.3(6) . .
C12 C11 H11A 107.0 . .
C10 C11 H11A 107.0 . .
C12 C11 H11B 107.0 . .
C10 C11 H11B 107.0 . .
H11A C11 H11B 106.8 . .
C11 C12 C13 124.1(7) . .
C11 C12 H12A 106.3 . .
C13 C12 H12A 106.3 . .
C11 C12 H12B 106.3 . .
C13 C12 H12B 106.3 . .
H12A C12 H12B 106.4 . .
C12 C13 C14 121.5(6) . .
C12 C13 H13A 106.9 . .
C14 C13 H13A 106.9 . .
C12 C13 H13B 106.9 . .
C14 C13 H13B 106.9 . .
H13A C13 H13B 106.7 . .
C8 C14 C13 115.4(5) . .
C8 C14 H14A 108.4 . .
C13 C14 H14A 108.4 . .
C8 C14 H14B 108.4 . .
C13 C14 H14B 108.4 . .
H14A C14 H14B 107.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.904(5) .
O1 C7 1.237(5) .
N1 C7 1.351(5) .
N1 C4 1.420(5) .
N1 H1 0.8600 .
N2 C7 1.336(5) .
N2 C8 1.463(5) .
N2 H2 0.8600 .
C1 C6 1.359(7) .
C1 C2 1.379(7) .
C2 C3 1.372(6) .
C2 H2A 0.9300 .
C3 C4 1.378(6) .
C3 H3 0.9300 .
C4 C5 1.382(6) .
C5 C6 1.388(6) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C8 C9 1.512(7) .
C8 C14 1.515(7) .
C8 H8 0.9800 .
C9 C10 1.521(7) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.493(9) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.412(9) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.429(8) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.519(7) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
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
C6 C1 C2 C3 -2.2(7) . . . .
Br1 C1 C2 C3 177.1(3) . . . .
C1 C2 C3 C4 1.1(7) . . . .
C2 C3 C4 C5 0.8(7) . . . .
C2 C3 C4 N1 -176.1(4) . . . .
C7 N1 C4 C3 -55.0(6) . . . .
C7 N1 C4 C5 128.1(5) . . . .
C3 C4 C5 C6 -1.7(7) . . . .
N1 C4 C5 C6 175.3(4) . . . .
C2 C1 C6 C5 1.3(7) . . . .
Br1 C1 C6 C5 -178.0(3) . . . .
C4 C5 C6 C1 0.6(7) . . . .
C8 N2 C7 O1 -10.5(8) . . . .
C8 N2 C7 N1 170.0(5) . . . .
C4 N1 C7 O1 0.6(7) . . . .
C4 N1 C7 N2 -179.9(5) . . . .
C7 N2 C8 C9 -106.1(5) . . . .
C7 N2 C8 C14 127.4(6) . . . .
N2 C8 C9 C10 160.1(5) . . . .
C14 C8 C9 C10 -76.9(6) . . . .
C8 C9 C10 C11 67.2(8) . . . .
C9 C10 C11 C12 -15.0(13) . . . .
C10 C11 C12 C13 -43.8(15) . . . .
C11 C12 C13 C14 68.8(13) . . . .
N2 C8 C14 C13 -176.1(5) . . . .
C9 C8 C14 C13 59.6(8) . . . .
C12 C13 C14 C8 -58.3(10) . . . .
