#------------------------------------------------------------------------------
#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/27/8102748.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_8102748
loop_
_publ_author_name
'Wen-Bo Guo'
'Pu-Zhou Hu'
'Shao-Bin Miao'
'Bang-Tun Zhao'
_publ_section_title
;
 Crystal structure of
 1-azonia-1-(2-mercaptobenzothiazolyl)ethyl-2-thiolato-1,3-benzothiazole,
 C16H12N2S4
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              469
_journal_volume                  225
_journal_year                    2010
_chemical_formula_sum            'C16 H12 N2 S4'
_chemical_formula_weight         360.52
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.565(2)
_cell_angle_beta                 105.498(2)
_cell_angle_gamma                98.481(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5938(7)
_cell_length_b                   10.0494(9)
_cell_length_c                   11.5670(11)
_cell_measurement_reflns_used    2341
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.44
_cell_volume                     810.17(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0088
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4406
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.44
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.582
_exptl_absorpt_correction_T_max  0.8870
_exptl_absorpt_correction_T_min  0.7916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0397P)²+0.2361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0817
_reflns_number_gt                2541
_reflns_number_total             2947
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3037.cff
_cod_data_source_block           00
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        810.16(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8102748
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.36077(7) 1.08055(5) 0.90553(4) 0.04677(14) Uani 1 1 d . . .
S2 S 0.38748(8) 0.80918(5) 0.74750(4) 0.05096(15) Uani 1 1 d . . .
S3 S 0.17938(8) 0.56369(7) 0.15175(5) 0.06186(18) Uani 1 1 d . . .
S4 S 0.19657(10) 0.41849(6) 0.35250(7) 0.0741(2) Uani 1 1 d . . .
N1 N 0.3432(2) 1.04275(15) 0.67244(13) 0.0411(3) Uani 1 1 d . . .
N2 N 0.1819(2) 0.68849(15) 0.36825(13) 0.0395(3) Uani 1 1 d . . .
C1 C 0.3290(2) 1.17998(18) 0.71585(16) 0.0385(4) Uani 1 1 d . . .
C2 C 0.3089(3) 1.27614(19) 0.64568(18) 0.0470(4) Uani 1 1 d . . .
H2 H 0.3053 1.2517 0.5627 0.056 Uiso 1 1 calc R . .
C3 C 0.2943(3) 1.4083(2) 0.7013(2) 0.0551(5) Uani 1 1 d . . .
H3 H 0.2807 1.4732 0.6550 0.066 Uiso 1 1 calc R . .
C4 C 0.2994(3) 1.4460(2) 0.8246(2) 0.0584(5) Uani 1 1 d . . .
H4 H 0.2887 1.5358 0.8596 0.070 Uiso 1 1 calc R . .
C5 C 0.3201(3) 1.3536(2) 0.89650(19) 0.0522(5) Uani 1 1 d . . .
H5 H 0.3245 1.3798 0.9796 0.063 Uiso 1 1 calc R . .
C6 C 0.3345(2) 1.21974(19) 0.84115(16) 0.0409(4) Uani 1 1 d . . .
C7 C 0.3610(2) 0.98111(18) 0.76083(16) 0.0397(4) Uani 1 1 d . . .
C8 C 0.3823(3) 0.75935(19) 0.58658(16) 0.0426(4) Uani 1 1 d . . .
H8A H 0.4509 0.8372 0.5681 0.051 Uiso 1 1 calc R . .
H8B H 0.4439 0.6819 0.5737 0.051 Uiso 1 1 calc R . .
C9 C 0.1828(2) 0.71678(19) 0.49811(16) 0.0410(4) Uani 1 1 d . . .
H9A H 0.1172 0.6338 0.5113 0.049 Uiso 1 1 calc R . .
H9B H 0.1175 0.7910 0.5155 0.049 Uiso 1 1 calc R . .
C10 C 0.1715(2) 0.79078(19) 0.30273(16) 0.0407(4) Uani 1 1 d . . .
C11 C 0.1635(3) 0.9282(2) 0.34766(19) 0.0498(5) Uani 1 1 d . . .
H11 H 0.1671 0.9631 0.4298 0.060 Uiso 1 1 calc R . .
C12 C 0.1499(3) 1.0123(2) 0.2670(2) 0.0645(6) Uani 1 1 d . . .
H12 H 0.1435 1.1049 0.2954 0.077 Uiso 1 1 calc R . .
C13 C 0.1456(3) 0.9613(3) 0.1454(2) 0.0717(7) Uani 1 1 d . . .
H13 H 0.1368 1.0203 0.0932 0.086 Uiso 1 1 calc R . .
C14 C 0.1541(3) 0.8253(3) 0.0997(2) 0.0690(7) Uani 1 1 d . . .
H14 H 0.1512 0.7916 0.0175 0.083 Uiso 1 1 calc R . .
C15 C 0.1674(3) 0.7386(2) 0.18010(18) 0.0509(5) Uani 1 1 d . . .
C16 C 0.1872(3) 0.5604(2) 0.30260(18) 0.0477(5) 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'
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'
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
_geom_angle_publ_flag
C6 S1 C7 88.55(8) . . ?
C7 S2 C8 99.68(8) . . ?
C15 S3 C16 92.55(9) . . ?
C7 N1 C1 110.16(15) . . ?
C16 N2 C10 115.58(15) . . ?
C16 N2 C9 122.03(15) . . ?
C10 N2 C9 122.38(15) . . ?
C2 C1 N1 125.47(16) . . ?
C2 C1 C6 119.41(17) . . ?
N1 C1 C6 115.12(15) . . ?
C3 C2 C1 118.88(18) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 121.15(19) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 121.36(19) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 117.95(19) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C5 C6 C1 121.25(18) . . ?
C5 C6 S1 129.17(15) . . ?
C1 C6 S1 109.58(13) . . ?
N1 C7 S2 125.32(14) . . ?
N1 C7 S1 116.59(13) . . ?
S2 C7 S1 118.09(10) . . ?
C9 C8 S2 111.68(13) . . ?
C9 C8 H8A 109.3 . . ?
S2 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
S2 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N2 C9 C8 110.84(14) . . ?
N2 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C15 121.02(17) . . ?
C11 C10 N2 126.96(17) . . ?
C15 C10 N2 112.02(17) . . ?
C10 C11 C12 118.1(2) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C12 121.3(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 118.2(2) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C10 C15 C14 120.1(2) . . ?
C10 C15 S3 110.20(15) . . ?
C14 C15 S3 129.66(18) . . ?
N2 C16 S4 127.16(15) . . ?
N2 C16 S3 109.66(14) . . ?
S4 C16 S3 123.18(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.7342(19) . ?
S1 C7 1.7534(18) . ?
S2 C7 1.7471(18) . ?
S2 C8 1.8072(18) . ?
S3 C15 1.737(2) . ?
S3 C16 1.738(2) . ?
S4 C16 1.655(2) . ?
N1 C7 1.294(2) . ?
N1 C1 1.392(2) . ?
N2 C16 1.357(2) . ?
N2 C10 1.403(2) . ?
N2 C9 1.465(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.405(2) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C8 C9 1.521(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.382(3) . ?
C10 C15 1.391(3) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.401(3) . ?
C14 H14 0.9300 . ?
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
_geom_torsion_publ_flag
C7 N1 C1 C2 179.83(17) . . . . ?
C7 N1 C1 C6 -0.7(2) . . . . ?
N1 C1 C2 C3 179.23(17) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 S1 -179.82(15) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
N1 C1 C6 C5 -179.47(16) . . . . ?
C2 C1 C6 S1 -179.89(14) . . . . ?
N1 C1 C6 S1 0.66(19) . . . . ?
C7 S1 C6 C5 179.84(18) . . . . ?
C7 S1 C6 C1 -0.30(13) . . . . ?
C1 N1 C7 S2 -178.78(13) . . . . ?
C1 N1 C7 S1 0.5(2) . . . . ?
C8 S2 C7 N1 0.26(18) . . . . ?
C8 S2 C7 S1 -179.01(11) . . . . ?
C6 S1 C7 N1 -0.12(15) . . . . ?
C6 S1 C7 S2 179.21(11) . . . . ?
C7 S2 C8 C9 -81.69(14) . . . . ?
C16 N2 C9 C8 87.86(19) . . . . ?
C10 N2 C9 C8 -93.52(19) . . . . ?
S2 C8 C9 N2 175.09(12) . . . . ?
C16 N2 C10 C11 179.63(18) . . . . ?
C9 N2 C10 C11 0.9(3) . . . . ?
C16 N2 C10 C15 0.4(2) . . . . ?
C9 N2 C10 C15 -178.32(15) . . . . ?
C15 C10 C11 C12 0.5(3) . . . . ?
N2 C10 C11 C12 -178.73(17) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C11 C10 C15 C14 -0.3(3) . . . . ?
N2 C10 C15 C14 179.00(17) . . . . ?
C11 C10 C15 S3 -179.95(14) . . . . ?
N2 C10 C15 S3 -0.64(19) . . . . ?
C13 C14 C15 C10 0.1(3) . . . . ?
C13 C14 C15 S3 179.64(17) . . . . ?
C16 S3 C15 C10 0.59(15) . . . . ?
C16 S3 C15 C14 -179.0(2) . . . . ?
C10 N2 C16 S4 -179.09(14) . . . . ?
C9 N2 C16 S4 -0.4(3) . . . . ?
C10 N2 C16 S3 0.08(19) . . . . ?
C9 N2 C16 S3 178.78(13) . . . . ?
C15 S3 C16 N2 -0.38(14) . . . . ?
C15 S3 C16 S4 178.83(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 940498
2 PubChem 1103390
