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#$Date: 2023-07-11 10:14:02 +0300 (Tue, 11 Jul 2023) $
#$Revision: 285141 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/74/8107458.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_8107458
loop_
_publ_author_name
'Li, Yingju'
'Yang, Zhimao'
_publ_section_title
;
 The crystal structure of 1-(2-chlorobenzyl)-3-(3,5-dichlorophenyl)urea,
 C14H11Cl3N2O
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              421
_journal_page_last               423
_journal_paper_doi               10.1515/ncrs-2022-0549
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C14 H11 Cl3 N2 O'
_chemical_formula_sum            'C14 H11 Cl3 N2 O'
_chemical_formula_weight         329.60
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3600(4)
_cell_length_b                   12.0085(8)
_cell_length_c                   14.3665(6)
_cell_measurement_reflns_used    1994
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7640
_cell_measurement_theta_min      4.1690
_cell_volume                     1442.27(13)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4927
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.764
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.420
_diffrn_reflns_theta_min         3.290
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 742 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0460
_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)+(0.0358P)²+0.1166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.551
_reflns_Friedel_fraction_full    0.857
_reflns_Friedel_fraction_max     0.632
_reflns_number_gt                2492
_reflns_number_total             3047
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0549_suppl.cif
_cod_data_source_block           0916e-2
_cod_database_code               8107458
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), N1(H1), N2(H2A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_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
C1 C 0.4442(4) 0.6117(3) 0.3845(2) 0.0315(8) Uani 1 1 d . . . . .
C2 C 0.4787(4) 0.6263(3) 0.2910(3) 0.0361(9) Uani 1 1 d . . . . .
H2 H 0.540130 0.686415 0.271430 0.043 Uiso 1 1 calc R U . . .
C3 C 0.4210(4) 0.5507(4) 0.2276(2) 0.0398(9) Uani 1 1 d . . . . .
C4 C 0.3314(4) 0.4589(3) 0.2538(3) 0.0424(9) Uani 1 1 d . . . . .
H4 H 0.292799 0.408309 0.210297 0.051 Uiso 1 1 calc R U . . .
C5 C 0.3021(4) 0.4463(3) 0.3477(2) 0.0365(8) Uani 1 1 d . . . . .
C6 C 0.3555(4) 0.5210(3) 0.4139(2) 0.0345(8) Uani 1 1 d . . . . .
H6 H 0.332361 0.510622 0.476584 0.041 Uiso 1 1 calc R U . . .
C7 C 0.4461(4) 0.7219(3) 0.5305(2) 0.0292(8) Uani 1 1 d . . . . .
C8 C 0.4978(4) 0.8333(3) 0.6707(2) 0.0377(9) Uani 1 1 d . . . . .
H8A H 0.595255 0.845309 0.705951 0.045 Uiso 1 1 calc R U . . .
H8B H 0.435791 0.777121 0.703027 0.045 Uiso 1 1 calc R U . . .
C9 C 0.4038(4) 0.9400(3) 0.6695(2) 0.0326(8) Uani 1 1 d . . . . .
C10 C 0.3756(4) 0.9994(4) 0.7512(3) 0.0450(10) Uani 1 1 d . . . . .
C11 C 0.2898(5) 1.0976(4) 0.7520(4) 0.0615(13) Uani 1 1 d . . . . .
H11 H 0.271136 1.134634 0.807874 0.074 Uiso 1 1 calc R U . . .
C12 C 0.2324(5) 1.1403(4) 0.6703(4) 0.0656(14) Uani 1 1 d . . . . .
H12 H 0.176199 1.207092 0.670272 0.079 Uiso 1 1 calc R U . . .
C13 C 0.2578(5) 1.0847(4) 0.5885(3) 0.0574(12) Uani 1 1 d . . . . .
H13 H 0.218513 1.113586 0.533000 0.069 Uiso 1 1 calc R U . . .
C14 C 0.3423(4) 0.9849(3) 0.5884(3) 0.0408(9) Uani 1 1 d . . . . .
H14 H 0.357759 0.947533 0.532476 0.049 Uiso 1 1 calc R U . . .
Cl1 Cl 0.46236(15) 0.56963(12) 0.11033(7) 0.0693(4) Uani 1 1 d . . . . .
Cl2 Cl 0.19757(14) 0.32855(9) 0.38288(8) 0.0596(3) Uani 1 1 d . . . . .
Cl3 Cl 0.45331(16) 0.94840(12) 0.85574(7) 0.0698(4) Uani 1 1 d . . . . .
N1 N 0.5093(3) 0.6892(3) 0.4472(2) 0.0370(8) Uani 1 1 d . . . . .
H1 H 0.598534 0.719357 0.431414 0.044 Uiso 1 1 calc R U . . .
N2 N 0.5402(3) 0.7909(2) 0.5797(2) 0.0369(7) Uani 1 1 d . . . . .
H2A H 0.630185 0.810793 0.555855 0.044 Uiso 1 1 calc R U . . .
O1 O 0.3121(2) 0.6907(2) 0.55759(16) 0.0337(6) Uani 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 N1 117.3(3) . .
C6 C1 C2 120.4(3) . .
C6 C1 N1 122.2(3) . .
C1 C2 H2 120.4 . .
C3 C2 C1 119.2(4) . .
C3 C2 H2 120.4 . .
C2 C3 C4 122.3(3) . .
C2 C3 Cl1 119.2(3) . .
C4 C3 Cl1 118.5(3) . .
C3 C4 H4 121.6 . .
C5 C4 C3 116.8(4) . .
C5 C4 H4 121.6 . .
C4 C5 C6 123.0(4) . .
C4 C5 Cl2 117.6(3) . .
C6 C5 Cl2 119.4(3) . .
C1 C6 H6 120.8 . .
C5 C6 C1 118.3(3) . .
C5 C6 H6 120.8 . .
N2 C7 N1 114.3(3) . .
O1 C7 N1 122.4(3) . .
O1 C7 N2 123.3(3) . .
H8A C8 H8B 107.6 . .
C9 C8 H8A 108.6 . .
C9 C8 H8B 108.6 . .
N2 C8 H8A 108.6 . .
N2 C8 H8B 108.6 . .
N2 C8 C9 114.7(3) . .
C10 C9 C8 121.0(3) . .
C14 C9 C8 122.5(3) . .
C14 C9 C10 116.5(4) . .
C9 C10 Cl3 118.8(3) . .
C11 C10 C9 122.2(4) . .
C11 C10 Cl3 119.0(3) . .
C10 C11 H11 120.2 . .
C12 C11 C10 119.6(4) . .
C12 C11 H11 120.2 . .
C11 C12 H12 120.0 . .
C13 C12 C11 120.0(4) . .
C13 C12 H12 120.0 . .
C12 C13 H13 120.0 . .
C12 C13 C14 120.0(5) . .
C14 C13 H13 120.0 . .
C9 C14 C13 121.6(4) . .
C9 C14 H14 119.2 . .
C13 C14 H14 119.2 . .
C1 N1 H1 116.5 . .
C7 N1 C1 127.1(3) . .
C7 N1 H1 116.5 . .
C7 N2 C8 123.3(3) . .
C7 N2 H2A 118.4 . .
C8 N2 H2A 118.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.385(5) .
C1 C6 1.384(5) .
C1 N1 1.405(4) .
C2 H2 0.9300 .
C2 C3 1.373(5) .
C3 C4 1.385(5) .
C3 Cl1 1.734(4) .
C4 H4 0.9300 .
C4 C5 1.378(5) .
C5 C6 1.382(5) .
C5 Cl2 1.737(4) .
C6 H6 0.9300 .
C7 N1 1.366(4) .
C7 N2 1.343(4) .
C7 O1 1.243(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C8 C9 1.503(5) .
C8 N2 1.447(4) .
C9 C10 1.394(5) .
C9 C14 1.382(5) .
C10 C11 1.380(6) .
C10 Cl3 1.747(4) .
C11 H11 0.9300 .
C11 C12 1.368(7) .
C12 H12 0.9300 .
C12 C13 1.367(7) .
C13 H13 0.9300 .
C13 C14 1.390(6) .
C14 H14 0.9300 .
N1 H1 0.8600 .
N2 H2A 0.8600 .
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
C1 C2 C3 C4 -1.1(5) . . . .
C1 C2 C3 Cl1 179.3(3) . . . .
C2 C1 C6 C5 -0.3(5) . . . .
C2 C1 N1 C7 150.7(3) . . . .
C2 C3 C4 C5 0.0(5) . . . .
C3 C4 C5 C6 1.1(5) . . . .
C3 C4 C5 Cl2 -177.2(2) . . . .
C4 C5 C6 C1 -0.9(5) . . . .
C6 C1 C2 C3 1.3(5) . . . .
C6 C1 N1 C7 -32.4(5) . . . .
C8 C9 C10 C11 179.9(3) . . . .
C8 C9 C10 Cl3 0.6(5) . . . .
C8 C9 C14 C13 -178.9(3) . . . .
C9 C8 N2 C7 -88.8(4) . . . .
C9 C10 C11 C12 -1.3(6) . . . .
C10 C9 C14 C13 0.5(5) . . . .
C10 C11 C12 C13 1.1(7) . . . .
C11 C12 C13 C14 -0.2(7) . . . .
C12 C13 C14 C9 -0.7(6) . . . .
C14 C9 C10 C11 0.5(5) . . . .
C14 C9 C10 Cl3 -178.8(3) . . . .
Cl1 C3 C4 C5 179.5(3) . . . .
Cl2 C5 C6 C1 177.3(2) . . . .
Cl3 C10 C11 C12 178.0(3) . . . .
N1 C1 C2 C3 178.3(3) . . . .
N1 C1 C6 C5 -177.2(3) . . . .
N1 C7 N2 C8 -178.5(3) . . . .
N2 C7 N1 C1 175.0(3) . . . .
N2 C8 C9 C10 -170.2(3) . . . .
N2 C8 C9 C14 9.2(5) . . . .
O1 C7 N1 C1 -5.6(5) . . . .
O1 C7 N2 C8 2.1(5) . . . .
