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#$Date: 2025-08-21 04:34:05 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/05/4510567.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_4510567
loop_
_publ_author_name
'Eccles, Kevin S.'
'Morrison, Robin E.'
'Maguire, Anita R.'
'Lawrence, Simon E.'
_publ_section_title
;
 Crystal Landscape of Primary Aromatic Thioamides
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2753
_journal_paper_doi               10.1021/cg401891f
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C7 H6 Cl N S'
_chemical_formula_weight         171.64
_chemical_name_common            '4-Chlorothiobenzamide '
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 100.382(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.121(5)
_cell_length_b                   10.546(2)
_cell_length_c                   7.6632(18)
_cell_measurement_reflns_used    2201
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      26.0698
_cell_measurement_theta_min      2.9022
_cell_volume                     1520.0(6)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection
;
'Bruker Instrument Service v2009, 3, 0, 0'
;
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'Mercury 3.0 (Macrae et al, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX II DUO'
_diffrn_measurement_method       'φ & ω  scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10910
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Plate '
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.875
_refine_diff_density_min         -0.523
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0615
_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)+(0.0839P)²+2.9390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1677
_refine_ls_wR_factor_ref         0.1792
_reflns_number_gt                2342
_reflns_number_total             3094
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401891f_si_003.cif
_cod_data_source_block           Compound_14_Beta
_cod_depositor_comments
'Adding full bibliography for 4510565--4510578.cif.'
_cod_database_code               4510567
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_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
C C1 0.5808(2) 0.8845(4) 0.3369(5) 0.0167(9) Uani d . 1
C C2 0.6139(3) 0.9679(4) 0.2345(6) 0.0220(10) Uani d . 1
H H2 0.5861 1.0276 0.159 0.026 Uiso calc R 1
C C3 0.6867(3) 0.9638(4) 0.2426(6) 0.0223(10) Uani d . 1
H H3 0.709 1.0216 0.175 0.027 Uiso calc R 1
C C4 0.7270(2) 0.8744(4) 0.3504(6) 0.0202(9) Uani d . 1
C C5 0.6951(2) 0.7903(4) 0.4505(6) 0.0216(10) Uani d . 1
H H5 0.7229 0.7291 0.5231 0.026 Uiso calc R 1
C C6 0.6228(2) 0.7960(4) 0.4442(6) 0.0208(9) Uani d . 1
H H6 0.601 0.7388 0.5138 0.025 Uiso calc R 1
C C7 0.5027(2) 0.8874(4) 0.3298(5) 0.0174(9) Uani d . 1
S S8 0.46066(6) 0.76264(10) 0.40176(15) 0.0211(3) Uani d . 1
H H9A 0.488(3) 1.055(6) 0.238(7) 0.031(15) Uiso d . 1
H H9B 0.4213(18) 1.002(5) 0.267(7) 0.022(13) Uiso d D 1
N N9 0.4666(2) 0.9904(4) 0.2684(5) 0.0206(8) Uani d D 1
Cl Cl10 0.81807(6) 0.86680(11) 0.36061(16) 0.0282(3) Uani d . 1
C C11 0.1854(2) 0.8328(4) 1.0264(6) 0.0198(9) Uani d . 1
C C12 0.1419(3) 0.9394(4) 0.9857(6) 0.0247(10) Uani d . 1
H H12 0.1602 1.0212 1.0195 0.03 Uiso calc R 1
C C13 0.0732(3) 0.9272(5) 0.8979(6) 0.0278(11) Uani d . 1
H H13 0.044 1.0001 0.8719 0.033 Uiso calc R 1
C C14 0.0464(2) 0.8080(5) 0.8471(6) 0.0266(10) Uani d . 1
C C15 0.0874(3) 0.7004(4) 0.8888(6) 0.0274(11) Uani d . 1
H H15 0.068 0.6189 0.8574 0.033 Uiso calc R 1
C C16 0.1568(2) 0.7125(4) 0.9763(6) 0.0240(10) Uani d . 1
H H16 0.1855 0.639 1.0029 0.029 Uiso calc R 1
C C17 0.2600(2) 0.8481(4) 1.1194(6) 0.0202(9) Uani d . 1
S S18 0.28467(6) 0.97292(10) 1.25301(15) 0.0215(3) Uani d . 1
H H19A 0.297(3) 0.707(7) 1.019(9) 0.05(2) Uiso d . 1
H H19B 0.3497(18) 0.759(4) 1.145(6) 0.011(11) Uiso d D 1
N N19 0.3063(2) 0.7601(4) 1.0916(6) 0.0230(9) Uani d D 1
Cl Cl20 -0.04029(6) 0.79439(14) 0.73227(18) 0.0372(4) Uani 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'
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
C6 C1 C2 118.6(4)
C6 C1 C7 120.2(4)
C2 C1 C7 121.2(4)
C3 C2 C1 120.5(4)
C3 C2 H2 119.8
C1 C2 H2 119.8
C2 C3 C4 119.5(4)
C2 C3 H3 120.2
C4 C3 H3 120.2
C5 C4 C3 120.7(4)
C5 C4 Cl10 119.0(3)
C3 C4 Cl10 120.2(3)
C6 C5 C4 119.5(4)
C6 C5 H5 120.2
C4 C5 H5 120.2
C5 C6 C1 121.1(4)
C5 C6 H6 119.4
C1 C6 H6 119.4
N9 C7 C1 119.0(4)
N9 C7 S8 120.5(4)
C1 C7 S8 120.5(3)
C7 N9 H9A 120.(4)
C7 N9 H9B 125.(3)
H9A N9 H9B 114.(5)
C12 C11 C16 118.6(4)
C12 C11 C17 120.0(4)
C16 C11 C17 121.4(4)
C13 C12 C11 120.9(4)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C14 119.7(4)
C12 C13 H13 120.2
C14 C13 H13 120.2
C15 C14 C13 120.9(4)
C15 C14 Cl20 119.9(4)
C13 C14 Cl20 119.2(4)
C16 C15 C14 119.4(4)
C16 C15 H15 120.3
C14 C15 H15 120.3
C15 C16 C11 120.5(4)
C15 C16 H16 119.8
C11 C16 H16 119.8
N19 C17 C11 117.3(4)
N19 C17 S18 121.6(4)
C11 C17 S18 121.1(3)
C17 N19 H19A 122.(5)
C17 N19 H19B 123.(3)
H19A N19 H19B 114.(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.397(6)
C1 C2 1.403(6)
C1 C7 1.486(6)
C2 C3 1.382(7)
C2 H2 0.95
C3 C4 1.391(6)
C3 H3 0.95
C4 C5 1.384(6)
C4 Cl10 1.731(5)
C5 C6 1.376(6)
C5 H5 0.95
C6 H6 0.95
C7 N9 1.326(5)
C7 S8 1.686(4)
N9 H9A 0.85(6)
N9 H9B 0.87(3)
C11 C12 1.399(6)
C11 C16 1.407(6)
C11 C17 1.485(6)
C12 C13 1.370(7)
C12 H12 0.95
C13 C14 1.386(7)
C13 H13 0.95
C14 C15 1.383(7)
C14 Cl20 1.737(5)
C15 C16 1.381(7)
C15 H15 0.95
C16 H16 0.95
C17 N19 1.326(6)
C17 S18 1.682(5)
N19 H19A 0.79(7)
N19 H19B 0.86(3)
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
N9 H9A S8 2_655 0.85(6) 2.70(6) 3.540(4) 171.(5)
N9 H9B S18 1_554 0.87(3) 2.61(3) 3.465(4) 165.(4)
N19 H19A S18 4_575 0.79(7) 2.76(7) 3.543(5) 171.(6)
N19 H19B S8 1_556 0.86(3) 2.62(3) 3.440(5) 161.(4)
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
C6 C1 C2 C3 -1.2(6)
C7 C1 C2 C3 -179.9(4)
C1 C2 C3 C4 1.4(6)
C2 C3 C4 C5 -0.5(7)
C2 C3 C4 Cl10 179.4(3)
C3 C4 C5 C6 -0.5(7)
Cl10 C4 C5 C6 179.7(3)
C4 C5 C6 C1 0.6(7)
C2 C1 C6 C5 0.3(6)
C7 C1 C6 C5 178.9(4)
C6 C1 C7 N9 161.9(4)
C2 C1 C7 N9 -19.5(6)
C6 C1 C7 S8 -17.1(5)
C2 C1 C7 S8 161.5(3)
C16 C11 C12 C13 -0.5(7)
C17 C11 C12 C13 179.1(4)
C11 C12 C13 C14 -0.6(7)
C12 C13 C14 C15 2.1(7)
C12 C13 C14 Cl20 -178.8(4)
C13 C14 C15 C16 -2.5(7)
Cl20 C14 C15 C16 178.5(4)
C14 C15 C16 C11 1.4(7)
C12 C11 C16 C15 0.1(7)
C17 C11 C16 C15 -179.5(4)
C12 C11 C17 N19 -152.8(4)
C16 C11 C17 N19 26.8(6)
C12 C11 C17 S18 26.8(6)
C16 C11 C17 S18 -153.7(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139147258
