#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/66/2226624.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226624
loop_
_publ_author_name
'Zheng, Xi'
'Li, Bo'
'Wang, Qiang'
'Guo, Li'
_publ_section_title
;
 N-Benzylcarbamothioyl-2-chlorobenzamide
;
_journal_coeditor_code           PK2248
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1774
_journal_paper_doi               10.1107/S1600536810023822
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H13 Cl N2 O S'
_chemical_formula_moiety         'C15 H13 Cl N2 O S'
_chemical_formula_sum            'C15 H13 Cl N2 O S'
_chemical_formula_weight         304.78
_chemical_name_systematic
;
N-Benzylcarbamothioyl-2-chlorobenzamide
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                110.150(5)
_cell_angle_beta                 90.767(3)
_cell_angle_gamma                104.058(3)
_cell_formula_units_Z            2
_cell_length_a                   7.347(2)
_cell_length_b                   9.658(3)
_cell_length_c                   11.003(3)
_cell_measurement_reflns_used    2259
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.19
_cell_volume                     707.0(4)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 28.6
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Rigaku AFC10/Saturn724+'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_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            5691
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         3.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.886
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0286
_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)+(0.0368P)²+0.2650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0731
_reflns_number_gt                2194
_reflns_number_total             2481
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2248.cif
_cod_data_source_block           I
_cod_database_code               2226624
_cod_database_fobs_code          2226624
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
Cl Cl1 0.69955(6) 0.10088(5) 0.08296(4) 0.03365(14) Uani d . 1 . .
S S1 0.81096(6) 0.64421(5) 0.00524(4) 0.02590(13) Uani d . 1 . .
O O1 0.71779(16) 0.46704(14) 0.34073(11) 0.0283(3) Uani d . 1 . .
N N1 0.84005(19) 0.48399(15) 0.15434(13) 0.0203(3) Uani d . 1 . .
N N2 0.62797(19) 0.63073(16) 0.20842(13) 0.0219(3) Uani d . 1 . .
C C1 0.9133(2) 0.18430(18) 0.18156(14) 0.0202(3) Uani d . 1 . .
C C2 1.0373(2) 0.09656(19) 0.18009(15) 0.0243(4) Uani d . 1 . .
H H2 1.0062 -0.0087 0.1267 0.029 Uiso calc R 1 . .
C C3 1.2074(2) 0.1651(2) 0.25780(16) 0.0264(4) Uani d . 1 . .
H H3 1.2953 0.1069 0.2562 0.032 Uiso calc R 1 . .
C C4 1.2512(2) 0.3177(2) 0.33806(16) 0.0261(4) Uani d . 1 . .
H H4 1.3678 0.3632 0.3919 0.031 Uiso calc R 1 . .
C C5 1.1247(2) 0.40367(18) 0.33975(15) 0.0226(3) Uani d . 1 . .
H H5 1.1539 0.5079 0.3956 0.027 Uiso calc R 1 . .
C C6 0.9550(2) 0.33762(17) 0.25978(14) 0.0181(3) Uani d . 1 . .
C C7 0.8239(2) 0.43410(17) 0.25728(15) 0.0192(3) Uani d . 1 . .
C C8 0.7526(2) 0.58559(17) 0.12955(14) 0.0193(3) Uani d . 1 . .
C C9 0.5298(2) 0.74124(19) 0.19805(16) 0.0254(4) Uani d . 1 . .
H H9A 0.4528 0.6995 0.1126 0.030 Uiso calc R 1 . .
H H9B 0.6234 0.8366 0.2031 0.030 Uiso calc R 1 . .
C C10 0.4041(2) 0.77650(17) 0.30540(15) 0.0201(3) Uani d . 1 . .
C C11 0.4601(2) 0.79494(18) 0.43245(15) 0.0227(3) Uani d . 1 . .
H H11 0.5805 0.7838 0.4530 0.027 Uiso calc R 1 . .
C C12 0.3419(2) 0.82945(18) 0.52955(16) 0.0253(4) Uani d . 1 . .
H H12 0.3805 0.8400 0.6158 0.030 Uiso calc R 1 . .
C C13 0.1679(2) 0.84838(18) 0.50053(17) 0.0279(4) Uani d . 1 . .
H H13 0.0868 0.8722 0.5668 0.033 Uiso calc R 1 . .
C C14 0.1120(2) 0.83262(19) 0.37480(17) 0.0285(4) Uani d . 1 . .
H H14 -0.0065 0.8474 0.3552 0.034 Uiso calc R 1 . .
C C15 0.2287(2) 0.79521(19) 0.27727(16) 0.0248(4) Uani d . 1 . .
H H15 0.1884 0.7823 0.1907 0.030 Uiso calc R 1 . .
H H1N 0.924(3) 0.459(2) 0.1044(18) 0.030(5) Uiso d . 1 . .
H H2N 0.605(3) 0.593(2) 0.2644(19) 0.032(5) Uiso d . 1 . .
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'
S S 0.1246 0.1234 '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'
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
C7 N1 C8 . . 127.85(13) ?
C7 N1 H1N . . 116.5(13) ?
C8 N1 H1N . . 115.2(13) ?
C8 N2 C9 . . 122.95(14) ?
C8 N2 H2N . . 117.3(13) ?
C9 N2 H2N . . 119.8(13) ?
C2 C1 C6 . . 121.61(15) ?
C2 C1 Cl1 . . 119.44(13) ?
C6 C1 Cl1 . . 118.95(12) ?
C3 C2 C1 . . 118.67(15) ?
C3 C2 H2 . . 120.7 ?
C1 C2 H2 . . 120.7 ?
C2 C3 C4 . . 120.76(15) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C5 C4 C3 . . 119.94(15) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.07(15) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C1 C6 C5 . . 118.92(14) ?
C1 C6 C7 . . 121.51(14) ?
C5 C6 C7 . . 119.54(14) ?
O1 C7 N1 . . 124.11(14) ?
O1 C7 C6 . . 122.83(13) ?
N1 C7 C6 . . 113.03(13) ?
N2 C8 N1 . . 116.48(14) ?
N2 C8 S1 . . 124.11(12) ?
N1 C8 S1 . . 119.41(11) ?
N2 C9 C10 . . 110.88(13) ?
N2 C9 H9A . . 109.5 ?
C10 C9 H9A . . 109.5 ?
N2 C9 H9B . . 109.5 ?
C10 C9 H9B . . 109.5 ?
H9A C9 H9B . . 108.1 ?
C15 C10 C11 . . 118.98(14) ?
C15 C10 C9 . . 118.94(14) ?
C11 C10 C9 . . 122.06(14) ?
C12 C11 C10 . . 120.64(15) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C13 C12 C11 . . 119.88(16) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C12 C13 C14 . . 119.91(15) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C13 C14 C15 . . 120.18(15) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C14 C15 C10 . . 120.39(15) ?
C14 C15 H15 . . 119.8 ?
C10 C15 H15 . . 119.8 ?
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
Cl1 C1 . 1.7409(16) ?
S1 C8 . 1.6752(16) ?
O1 C7 . 1.2207(19) ?
N1 C7 . 1.371(2) ?
N1 C8 . 1.3913(19) ?
N1 H1N . 0.85(2) ?
N2 C8 . 1.318(2) ?
N2 C9 . 1.459(2) ?
N2 H2N . 0.82(2) ?
C1 C2 . 1.383(2) ?
C1 C6 . 1.386(2) ?
C2 C3 . 1.382(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.386(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.385(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.390(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.500(2) ?
C9 C10 . 1.506(2) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C15 . 1.389(2) ?
C10 C11 . 1.390(2) ?
C11 C12 . 1.388(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.383(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.384(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.387(2) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
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 H1N S1 2_765 0.86(2) 2.53(2) 3.3698(18) 166.2(18)
N2 H2N O1 . 0.82(2) 2.01(2) 2.669(2) 137(2)
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
C6 C1 C2 C3 . . . . -0.7(2) ?
Cl1 C1 C2 C3 . . . . 179.23(12) ?
C1 C2 C3 C4 . . . . 1.6(2) ?
C2 C3 C4 C5 . . . . -0.8(2) ?
C3 C4 C5 C6 . . . . -0.8(2) ?
C2 C1 C6 C5 . . . . -0.9(2) ?
Cl1 C1 C6 C5 . . . . 179.18(11) ?
C2 C1 C6 C7 . . . . 177.52(14) ?
Cl1 C1 C6 C7 . . . . -2.4(2) ?
C4 C5 C6 C1 . . . . 1.6(2) ?
C4 C5 C6 C7 . . . . -176.77(14) ?
C8 N1 C7 O1 . . . . 4.5(3) ?
C8 N1 C7 C6 . . . . -173.81(14) ?
C1 C6 C7 O1 . . . . 101.52(19) ?
C5 C6 C7 O1 . . . . -80.1(2) ?
C1 C6 C7 N1 . . . . -80.19(18) ?
C5 C6 C7 N1 . . . . 98.18(17) ?
C9 N2 C8 N1 . . . . 177.65(14) ?
C9 N2 C8 S1 . . . . -1.7(2) ?
C7 N1 C8 N2 . . . . -5.7(2) ?
C7 N1 C8 S1 . . . . 173.68(13) ?
C8 N2 C9 C10 . . . . -177.02(15) ?
N2 C9 C10 C15 . . . . -141.11(15) ?
N2 C9 C10 C11 . . . . 40.6(2) ?
C15 C10 C11 C12 . . . . 0.9(2) ?
C9 C10 C11 C12 . . . . 179.12(15) ?
C10 C11 C12 C13 . . . . -1.1(2) ?
C11 C12 C13 C14 . . . . 0.1(2) ?
C12 C13 C14 C15 . . . . 1.1(3) ?
C13 C14 C15 C10 . . . . -1.4(3) ?
C11 C10 C15 C14 . . . . 0.4(2) ?
C9 C10 C15 C14 . . . . -177.92(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2071531
2 PubChem 2792217
