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#$Date: 2024-04-04 18:30:56 +0300 (Thu, 04 Apr 2024) $
#$Revision: 290787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159869.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_7159869
loop_
_publ_author_name
'Shaikh, Aijaz'
'Sahoo, Satyajit'
'Marder, Seth R.'
'Barlow, Stephen'
'Mohapatra, Swagat K.'
_publ_section_title
;
 Reductive dimerization of benzothiazolium salts.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2115
_journal_page_last               2123
_journal_paper_doi               10.1039/d3ob01871g
_journal_volume                  22
_journal_year                    2024
_chemical_formula_sum            'C30 H28 N2 S2'
_chemical_formula_weight         480.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-09-08 deposited with the CCDC.	2024-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.559(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7804(15)
_cell_length_b                   9.5679(8)
_cell_length_c                   15.6535(11)
_cell_measurement_reflns_used    3990
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.39
_cell_volume                     2552.5(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22934
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_min         2.441
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0545
_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)+(0.1000P)²+0.4349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1994
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1819
_reflns_number_total             2939
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01871g2.cif
_cod_data_source_block           T_MBT2
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7159869
_shelx_shelxl_version_number     2019/1
_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   0.934
_shelx_estimated_absorpt_t_max   0.958
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
S1 S 0.39719(4) 0.35751(8) 0.62727(5) 0.0483(3) Uani 1 1 d . . . . .
N1 N 0.43440(13) 0.4809(2) 0.78436(14) 0.0418(6) Uani 1 1 d . . . . .
C6 C 0.40638(15) 0.5843(3) 0.72166(18) 0.0404(6) Uani 1 1 d . . . . .
C7 C 0.45523(16) 0.3483(3) 0.74792(18) 0.0408(6) Uani 1 1 d . . . . .
C8 C 0.42699(16) 0.2246(3) 0.79321(17) 0.0410(6) Uani 1 1 d . . . . .
C13 C 0.47557(17) 0.1202(3) 0.83961(18) 0.0428(7) Uani 1 1 d . . . . .
H13 H 0.528390 0.120001 0.841786 0.051 Uiso 1 1 calc R U . . .
C11 C 0.36832(18) 0.0115(3) 0.88119(19) 0.0484(7) Uani 1 1 d . . . . .
C1 C 0.38355(16) 0.5382(3) 0.63353(17) 0.0431(7) Uani 1 1 d . . . . .
C12 C 0.44637(18) 0.0152(3) 0.88318(18) 0.0454(7) Uani 1 1 d . . . . .
H12 H 0.480167 -0.053753 0.914158 0.055 Uiso 1 1 calc R U . . .
C9 C 0.34818(18) 0.2192(3) 0.7909(2) 0.0515(7) Uani 1 1 d . . . . .
H9 H 0.313980 0.287428 0.759792 0.062 Uiso 1 1 calc R U . . .
C10 C 0.31987(18) 0.1145(3) 0.8339(2) 0.0531(8) Uani 1 1 d . . . . .
H10 H 0.266868 0.113385 0.830824 0.064 Uiso 1 1 calc R U . . .
C5 C 0.39851(18) 0.7244(3) 0.7397(2) 0.0507(7) Uani 1 1 d . . . . .
H5 H 0.413423 0.756547 0.798239 0.061 Uiso 1 1 calc R U . . .
C2 C 0.35367(18) 0.6295(3) 0.5642(2) 0.0529(8) Uani 1 1 d . . . . .
H2 H 0.338534 0.597813 0.505581 0.064 Uiso 1 1 calc R U . . .
C15 C 0.4343(2) 0.5011(3) 0.87542(19) 0.0553(8) Uani 1 1 d . . . . .
H15A H 0.471338 0.572756 0.902161 0.083 Uiso 1 1 calc R U . . .
H15B H 0.448630 0.415418 0.907842 0.083 Uiso 1 1 calc R U . . .
H15C H 0.382790 0.528771 0.877008 0.083 Uiso 1 1 calc R U . . .
C3 C 0.3465(2) 0.7709(4) 0.5835(2) 0.0625(9) Uani 1 1 d . . . . .
H3 H 0.326868 0.834215 0.537498 0.075 Uiso 1 1 calc R U . . .
C4 C 0.3683(2) 0.8161(3) 0.6702(3) 0.0600(9) Uani 1 1 d . . . . .
H4 H 0.362749 0.910059 0.682359 0.072 Uiso 1 1 calc R U . . .
C14 C 0.3375(2) -0.1020(4) 0.9295(2) 0.0660(9) Uani 1 1 d . . . . .
H14A H 0.380462 -0.157292 0.964039 0.099 Uiso 1 1 calc R U . . .
H14B H 0.301743 -0.160518 0.886786 0.099 Uiso 1 1 calc R U . . .
H14C H 0.310592 -0.060174 0.968232 0.099 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 0.0033 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
C1 S1 C7 92.01(12) . . ?
C6 N1 C15 120.3(2) . . ?
C6 N1 C7 114.8(2) . . ?
C15 N1 C7 124.6(2) . . ?
N1 C6 C5 125.8(2) . . ?
N1 C6 C1 114.8(2) . . ?
C5 C6 C1 119.4(3) . . ?
N1 C7 C8 109.4(2) . . ?
N1 C7 C7 110.19(16) . 2_656 ?
C8 C7 C7 116.14(19) . 2_656 ?
N1 C7 S1 102.78(17) . . ?
C8 C7 S1 109.99(18) . . ?
C7 C7 S1 107.5(2) 2_656 . ?
C13 C8 C9 117.4(3) . . ?
C13 C8 C7 124.2(2) . . ?
C9 C8 C7 118.4(2) . . ?
C8 C13 C12 120.9(3) . . ?
C10 C11 C12 117.7(3) . . ?
C10 C11 C14 121.4(3) . . ?
C12 C11 C14 120.8(3) . . ?
C2 C1 C6 121.2(3) . . ?
C2 C1 S1 127.6(2) . . ?
C6 C1 S1 111.2(2) . . ?
C11 C12 C13 121.3(3) . . ?
C10 C9 C8 121.3(3) . . ?
C11 C10 C9 121.5(3) . . ?
C4 C5 C6 119.5(3) . . ?
C1 C2 C3 118.7(3) . . ?
C4 C3 C2 120.1(3) . . ?
C3 C4 C5 121.1(3) . . ?
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 C1 1.752(3) . ?
S1 C7 1.878(3) . ?
N1 C6 1.383(3) . ?
N1 C15 1.439(3) . ?
N1 C7 1.480(3) . ?
C6 C5 1.385(4) . ?
C6 C1 1.394(4) . ?
C7 C8 1.536(4) . ?
C7 C7 1.575(5) 2_656 ?
C8 C13 1.383(4) . ?
C8 C9 1.392(4) . ?
C13 C12 1.395(4) . ?
C11 C10 1.378(4) . ?
C11 C12 1.380(4) . ?
C11 C14 1.513(4) . ?
C1 C2 1.376(4) . ?
C9 C10 1.379(4) . ?
C5 C4 1.382(4) . ?
C2 C3 1.400(5) . ?
C3 C4 1.370(5) . ?
