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#$Date: 2022-10-21 09:43:29 +0300 (Fri, 21 Oct 2022) $
#$Revision: 278681 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/59/8105914.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_8105914
loop_
_publ_author_name
'Yeo, Chien Ing'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of 1-(4-chlorophenyl)-3-[methyl(phenyl)amino]thiourea,
 C14H14ClN3S
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              989
_journal_page_last               990
_journal_paper_doi               10.1515/ncrs-2019-0205
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C14 H14 Cl N3 S'
_chemical_formula_sum            'C14 H14 Cl N3 S'
_chemical_formula_weight         291.79
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.4000(2)
_cell_length_b                   11.5622(2)
_cell_length_c                   23.4776(4)
_cell_measurement_reflns_used    10188
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.4570
_cell_measurement_theta_min      3.7670
_cell_volume                     2823.11(9)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2014/7 [3]'
_computing_structure_refinement  'SHELXL-2014/7 [3]'
_computing_structure_solution    'SHELXT 2014/5 [2]'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17794
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         3.765
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.683
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2528
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0447P)²+1.2694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0774
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2339
_reflns_number_total             2528
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0205_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8105914
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.650
_shelx_estimated_absorpt_t_max   0.870
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'
'-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
Cl1 Cl 1.10565(4) 0.53817(4) 0.22483(2) 0.03176(13) Uani 1 1 d . . . . .
S1 S 0.65724(3) 0.44069(3) 0.44029(2) 0.01886(12) Uani 1 1 d . . . . .
N1 N 0.73050(11) 0.65576(10) 0.40536(5) 0.0156(2) Uani 1 1 d D . . . .
H1N H 0.7099(16) 0.7287(9) 0.4054(7) 0.019 Uiso 1 1 d D U . . .
N2 N 0.55180(11) 0.64007(10) 0.46063(5) 0.0170(3) Uani 1 1 d D . . . .
H2N H 0.5015(14) 0.6021(14) 0.4843(6) 0.020 Uiso 1 1 d D U . . .
N3 N 0.53154(11) 0.76010(10) 0.45575(5) 0.0164(2) Uani 1 1 d . . . . .
C1 C 0.64935(13) 0.58614(13) 0.43432(6) 0.0150(3) Uani 1 1 d . . . . .
C2 C 0.82739(12) 0.62659(12) 0.36539(6) 0.0149(3) Uani 1 1 d . . . . .
C3 C 0.85227(13) 0.70651(12) 0.32236(6) 0.0188(3) Uani 1 1 d . . . . .
H3 H 0.8088 0.7788 0.3222 0.023 Uiso 1 1 calc R U . . .
C4 C 0.93989(14) 0.68124(13) 0.27983(6) 0.0217(3) Uani 1 1 d . . . . .
H4 H 0.9571 0.7359 0.2506 0.026 Uiso 1 1 calc R U . . .
C5 C 1.00250(14) 0.57522(14) 0.28030(6) 0.0205(3) Uani 1 1 d . . . . .
C6 C 0.98471(14) 0.49808(13) 0.32446(6) 0.0203(3) Uani 1 1 d . . . . .
H6 H 1.0316 0.4276 0.3254 0.024 Uiso 1 1 calc R U . . .
C7 C 0.89759(13) 0.52412(13) 0.36765(6) 0.0183(3) Uani 1 1 d . . . . .
H7 H 0.8861 0.4721 0.3986 0.022 Uiso 1 1 calc R U . . .
C8 C 0.41299(13) 0.78552(12) 0.42717(6) 0.0162(3) Uani 1 1 d . . . . .
C9 C 0.37541(14) 0.71855(13) 0.38050(6) 0.0205(3) Uani 1 1 d . . . . .
H9 H 0.4257 0.6538 0.3694 0.025 Uiso 1 1 calc R U . . .
C10 C 0.26488(15) 0.74629(15) 0.35031(7) 0.0266(3) Uani 1 1 d . . . . .
H10 H 0.2393 0.6996 0.3190 0.032 Uiso 1 1 calc R U . . .
C11 C 0.19132(15) 0.84168(15) 0.36549(7) 0.0281(4) Uani 1 1 d . . . . .
H11 H 0.1166 0.8613 0.3443 0.034 Uiso 1 1 calc R U . . .
C12 C 0.22811(14) 0.90769(13) 0.41173(7) 0.0253(3) Uani 1 1 d . . . . .
H12 H 0.1782 0.9731 0.4222 0.030 Uiso 1 1 calc R U . . .
C13 C 0.33736(14) 0.87961(13) 0.44315(6) 0.0197(3) Uani 1 1 d . . . . .
H13 H 0.3603 0.9246 0.4755 0.024 Uiso 1 1 calc R U . . .
C14 C 0.55625(14) 0.81815(12) 0.51024(6) 0.0214(3) Uani 1 1 d . . . . .
H14A H 0.4890 0.7972 0.5376 0.032 Uiso 1 1 calc R U . . .
H14B H 0.5560 0.9021 0.5045 0.032 Uiso 1 1 calc R U . . .
H14C H 0.6402 0.7939 0.5250 0.032 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 0.0181 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'
Cl Cl 0.3639 0.7018 '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'
S S 0.3331 0.5567 '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
C1 N1 C2 129.48(12) . .
C1 N1 H1N 115.1(11) . .
C2 N1 H1N 114.0(11) . .
C1 N2 N3 122.25(12) . .
C1 N2 H2N 120.5(11) . .
N3 N2 H2N 117.0(11) . .
N2 N3 C8 111.63(11) . .
N2 N3 C14 110.70(11) . .
C8 N3 C14 117.69(11) . .
N2 C1 N1 115.31(12) . .
N2 C1 S1 117.46(10) . .
N1 C1 S1 127.23(11) . .
C3 C2 C7 119.63(13) . .
C3 C2 N1 117.01(12) . .
C7 C2 N1 123.36(13) . .
C4 C3 C2 120.39(13) . .
C4 C3 H3 119.8 . .
C2 C3 H3 119.8 . .
C3 C4 C5 119.33(13) . .
C3 C4 H4 120.3 . .
C5 C4 H4 120.3 . .
C6 C5 C4 120.92(13) . .
C6 C5 Cl1 119.05(12) . .
C4 C5 Cl1 120.03(11) . .
C5 C6 C7 119.63(13) . .
C5 C6 H6 120.2 . .
C7 C6 H6 120.2 . .
C6 C7 C2 119.82(13) . .
C6 C7 H7 120.1 . .
C2 C7 H7 120.1 . .
C13 C8 C9 119.05(13) . .
C13 C8 N3 121.28(13) . .
C9 C8 N3 119.59(12) . .
C10 C9 C8 120.27(14) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
C9 C10 C11 120.57(15) . .
C9 C10 H10 119.7 . .
C11 C10 H10 119.7 . .
C12 C11 C10 119.21(14) . .
C12 C11 H11 120.4 . .
C10 C11 H11 120.4 . .
C11 C12 C13 120.89(14) . .
C11 C12 H12 119.6 . .
C13 C12 H12 119.6 . .
C12 C13 C8 119.97(14) . .
C12 C13 H13 120.0 . .
C8 C13 H13 120.0 . .
N3 C14 H14A 109.5 . .
N3 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
N3 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C5 1.7408(14) .
S1 C1 1.6896(15) .
N1 C1 1.3499(18) .
N1 C2 1.4176(18) .
N1 H1N 0.870(9) .
N2 C1 1.3415(18) .
N2 N3 1.4084(16) .
N2 H2N 0.880(9) .
N3 C8 1.4341(18) .
N3 C14 1.4675(18) .
C2 C3 1.393(2) .
C2 C7 1.393(2) .
C3 C4 1.383(2) .
C3 H3 0.9500 .
C4 C5 1.388(2) .
C4 H4 0.9500 .
C5 C6 1.380(2) .
C6 C7 1.393(2) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 C13 1.394(2) .
C8 C9 1.398(2) .
C9 C10 1.388(2) .
C9 H9 0.9500 .
C10 C11 1.389(2) .
C10 H10 0.9500 .
C11 C12 1.381(2) .
C11 H11 0.9500 .
C12 C13 1.393(2) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
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 N2 N3 C8 115.07(14) . . . .
C1 N2 N3 C14 -111.75(14) . . . .
N3 N2 C1 N1 3.38(19) . . . .
N3 N2 C1 S1 -176.19(10) . . . .
C2 N1 C1 N2 -167.48(13) . . . .
C2 N1 C1 S1 12.0(2) . . . .
C1 N1 C2 C3 148.75(14) . . . .
C1 N1 C2 C7 -31.7(2) . . . .
C7 C2 C3 C4 4.4(2) . . . .
N1 C2 C3 C4 -176.10(13) . . . .
C2 C3 C4 C5 0.3(2) . . . .
C3 C4 C5 C6 -4.2(2) . . . .
C3 C4 C5 Cl1 176.06(11) . . . .
C4 C5 C6 C7 3.5(2) . . . .
Cl1 C5 C6 C7 -176.80(11) . . . .
C5 C6 C7 C2 1.2(2) . . . .
C3 C2 C7 C6 -5.1(2) . . . .
N1 C2 C7 C6 175.40(13) . . . .
N2 N3 C8 C13 143.68(13) . . . .
C14 N3 C8 C13 14.07(19) . . . .
N2 N3 C8 C9 -39.67(17) . . . .
C14 N3 C8 C9 -169.28(12) . . . .
C13 C8 C9 C10 0.6(2) . . . .
N3 C8 C9 C10 -176.17(13) . . . .
C8 C9 C10 C11 1.0(2) . . . .
C9 C10 C11 C12 -1.2(2) . . . .
C10 C11 C12 C13 -0.1(2) . . . .
C11 C12 C13 C8 1.6(2) . . . .
C9 C8 C13 C12 -1.8(2) . . . .
N3 C8 C13 C12 174.82(13) . . . .
