#------------------------------------------------------------------------------
#$Date: 2024-04-04 18:30:56 +0300 (Thu, 04 Apr 2024) $
#$Revision: 290787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159872.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_7159872
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            'C32 H34 N4 S2'
_chemical_formula_weight         538.75
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                99.778(3)
_cell_angle_beta                 108.497(3)
_cell_angle_gamma                113.542(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0557(11)
_cell_length_b                   11.7243(12)
_cell_length_c                   13.4222(14)
_cell_measurement_reflns_used    5519
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      2.22
_cell_volume                     1421.9(3)
_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 0.997
_diffrn_measured_fraction_theta_max 0.994
_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  0.0809
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31189
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.551
_diffrn_reflns_theta_min         2.905
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.947
_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            Yellow
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       Block
_exptl_crystal_F_000             572.0
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         6534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1299
_refine_ls_R_factor_gt           0.0597
_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+0.5914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.2129
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3659
_reflns_number_total             6572
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01871g2.cif
_cod_data_source_block           N_MBT2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7159872
_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.
;
loop_
_space_group_symop_operation_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_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
S2 S 0.14229(9) 0.09183(8) 0.64264(7) 0.0485(2) Uani 1 1 d . . . . .
S1 S 0.59140(9) 0.38113(9) 0.71148(7) 0.0578(3) Uani 1 1 d . . . . .
N1 N 0.3754(3) 0.3148(2) 0.80916(19) 0.0450(6) Uani 1 1 d . . . . .
N2 N 0.4332(3) 0.1181(3) 0.6758(2) 0.0502(6) Uani 1 1 d . . . . .
C24 C 0.2576(3) 0.3401(3) 0.6310(2) 0.0435(7) Uani 1 1 d . . . . .
N3 N 0.1523(4) 0.5853(3) 0.4636(3) 0.0693(9) Uani 1 1 d . . . . .
C23 C 0.3083(3) 0.2547(3) 0.6870(2) 0.0412(7) Uani 1 1 d . . . . .
C6 C 0.3703(4) 0.0494(3) 0.7363(2) 0.0489(8) Uani 1 1 d . . . . .
C1 C 0.2316(4) 0.0252(3) 0.7264(3) 0.0475(7) Uani 1 1 d . . . . .
C29 C 0.3313(3) 0.4771(3) 0.6808(3) 0.0472(7) Uani 1 1 d . . . . .
H29 H 0.405774 0.515572 0.752689 0.057 Uiso 1 1 calc R U . . .
C7 C 0.4118(3) 0.2241(3) 0.6435(2) 0.0441(7) Uani 1 1 d . . . . .
C22 C 0.5126(3) 0.3379(3) 0.8797(3) 0.0479(7) Uani 1 1 d . . . . .
C32 C 0.2756(4) 0.3161(3) 0.8587(3) 0.0570(8) Uani 1 1 d . . . . .
H32A H 0.234442 0.234884 0.872971 0.085 Uiso 1 1 calc R U . . .
H32B H 0.198826 0.324981 0.808041 0.085 Uiso 1 1 calc R U . . .
H32C H 0.327884 0.389320 0.927649 0.085 Uiso 1 1 calc R U . . .
C8 C 0.3602(4) 0.1919(3) 0.5173(3) 0.0497(8) Uani 1 1 d . . . . .
C27 C 0.1855(4) 0.5052(3) 0.5184(3) 0.0498(8) Uani 1 1 d . . . . .
C25 C 0.1433(4) 0.2877(3) 0.5246(3) 0.0503(8) Uani 1 1 d . . . . .
H25 H 0.089380 0.196322 0.489652 0.060 Uiso 1 1 calc R U . . .
C28 C 0.2971(4) 0.5575(3) 0.6267(3) 0.0516(8) Uani 1 1 d . . . . .
H28 H 0.349402 0.648653 0.662973 0.062 Uiso 1 1 calc R U . . .
C26 C 0.1077(4) 0.3664(3) 0.4697(3) 0.0526(8) Uani 1 1 d . . . . .
H26 H 0.030705 0.327233 0.398890 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4413(4) -0.0030(3) 0.8058(3) 0.0632(9) Uani 1 1 d . . . . .
H5 H 0.535434 0.015229 0.816767 0.076 Uiso 1 1 calc R U . . .
C17 C 0.6269(4) 0.3750(3) 0.8468(3) 0.0544(8) Uani 1 1 d . . . . .
C21 C 0.5444(4) 0.3314(3) 0.9880(3) 0.0566(8) Uani 1 1 d . . . . .
H21 H 0.470540 0.304870 1.011924 0.068 Uiso 1 1 calc R U . . .
C2 C 0.1647(5) -0.0515(3) 0.7814(3) 0.0641(10) Uani 1 1 d . . . . .
H2 H 0.073173 -0.065826 0.775072 0.077 Uiso 1 1 calc R U . . .
C9 C 0.2675(4) 0.0615(4) 0.4460(3) 0.0569(8) Uani 1 1 d . . . . .
H9 H 0.240877 -0.005069 0.476490 0.068 Uiso 1 1 calc R U . . .
C16 C 0.5492(4) 0.1002(4) 0.6579(3) 0.0674(10) Uani 1 1 d . . . . .
H16A H 0.638863 0.152282 0.724357 0.101 Uiso 1 1 calc R U . . .
H16B H 0.561124 0.128151 0.596798 0.101 Uiso 1 1 calc R U . . .
H16C H 0.523852 0.008520 0.640708 0.101 Uiso 1 1 calc R U . . .
C4 C 0.3725(6) -0.0810(4) 0.8576(3) 0.0762(12) Uani 1 1 d . . . . .
H4 H 0.420097 -0.116881 0.901439 0.091 Uiso 1 1 calc R U . . .
C13 C 0.3981(4) 0.2878(4) 0.4683(3) 0.0630(9) Uani 1 1 d . . . . .
H13 H 0.460227 0.375977 0.513648 0.076 Uiso 1 1 calc R U . . .
C20 C 0.6841(5) 0.3639(4) 1.0595(3) 0.0687(11) Uani 1 1 d . . . . .
H20 H 0.703366 0.361480 1.131575 0.082 Uiso 1 1 calc R U . . .
C10 C 0.2136(4) 0.0279(4) 0.3311(3) 0.0680(10) Uani 1 1 d . . . . .
H10 H 0.150627 -0.060178 0.285804 0.082 Uiso 1 1 calc R U . . .
C18 C 0.7656(4) 0.4041(4) 0.9188(3) 0.0741(11) Uani 1 1 d . . . . .
H18 H 0.839733 0.426865 0.895061 0.089 Uiso 1 1 calc R U . . .
N4 N 0.1977(5) 0.0909(6) 0.1656(3) 0.1162(16) Uani 1 1 d . . . . .
C11 C 0.2525(4) 0.1247(5) 0.2825(3) 0.0782(12) Uani 1 1 d . . . . .
C3 C 0.2353(6) -0.1069(4) 0.8458(3) 0.0767(12) Uani 1 1 d . . . . .
H3 H 0.189835 -0.160900 0.880532 0.092 Uiso 1 1 calc R U . . .
C12 C 0.3460(4) 0.2554(5) 0.3540(3) 0.0809(13) Uani 1 1 d . . . . .
H12 H 0.373721 0.322200 0.323848 0.097 Uiso 1 1 calc R U . . .
C19 C 0.7940(5) 0.3994(4) 1.0256(4) 0.0815(12) Uani 1 1 d . . . . .
H19 H 0.887286 0.420312 1.074086 0.098 Uiso 1 1 calc R U . . .
C30 C 0.0514(5) 0.5308(4) 0.3466(3) 0.0786(12) Uani 1 1 d . . . . .
H30A H 0.089939 0.494683 0.302977 0.118 Uiso 1 1 calc R U . . .
H30B H 0.037971 0.599363 0.322966 0.118 Uiso 1 1 calc R U . . .
H30C H -0.040663 0.462061 0.336289 0.118 Uiso 1 1 calc R U . . .
C31 C 0.2363(5) 0.7271(4) 0.5151(4) 0.0801(12) Uani 1 1 d . . . . .
H31A H 0.225375 0.753467 0.582055 0.120 Uiso 1 1 calc R U . . .
H31B H 0.202198 0.767506 0.464259 0.120 Uiso 1 1 calc R U . . .
H31C H 0.337286 0.754875 0.533400 0.120 Uiso 1 1 calc R U . . .
C14 C 0.1236(7) -0.0490(8) 0.0974(4) 0.137(3) Uani 1 1 d . . . . .
H14A H 0.092102 -0.057874 0.019794 0.205 Uiso 1 1 calc R U . . .
H14B H 0.040557 -0.097171 0.110936 0.205 Uiso 1 1 calc R U . . .
H14C H 0.189693 -0.083873 0.116767 0.205 Uiso 1 1 calc R U . . .
C15 C 0.2670(7) 0.1817(9) 0.1202(4) 0.207(5) Uani 1 1 d . . . . .
H15A H 0.240359 0.250223 0.126543 0.311 Uiso 1 1 calc R U . . .
H15B H 0.237382 0.137071 0.042883 0.311 Uiso 1 1 calc R U . . .
H15C H 0.370742 0.219956 0.160094 0.311 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 S2 C23 95.57(14) . . ?
C17 S1 C7 94.50(14) . . ?
C22 N1 C32 117.8(3) . . ?
C22 N1 C23 124.6(2) . . ?
C32 N1 C23 115.5(2) . . ?
C6 N2 C16 118.0(3) . . ?
C6 N2 C7 125.7(3) . . ?
C16 N2 C7 115.5(3) . . ?
C29 C24 C25 116.4(3) . . ?
C29 C24 C23 120.9(3) . . ?
C25 C24 C23 122.5(3) . . ?
C27 N3 C31 120.4(3) . . ?
C27 N3 C30 120.6(3) . . ?
C31 N3 C30 118.1(3) . . ?
N1 C23 C24 111.1(2) . . ?
N1 C23 C7 112.1(2) . . ?
C24 C23 C7 111.5(2) . . ?
N1 C23 S2 109.26(19) . . ?
C24 C23 S2 106.7(2) . . ?
C7 C23 S2 105.97(19) . . ?
N2 C6 C1 121.1(3) . . ?
N2 C6 C5 120.9(3) . . ?
C1 C6 C5 118.0(3) . . ?
C2 C1 C6 120.8(3) . . ?
C2 C1 S2 120.3(3) . . ?
C6 C1 S2 118.9(2) . . ?
C28 C29 C24 122.0(3) . . ?
N2 C7 C8 110.2(2) . . ?
N2 C7 C23 111.9(2) . . ?
C8 C7 C23 112.9(2) . . ?
N2 C7 S1 109.0(2) . . ?
C8 C7 S1 106.9(2) . . ?
C23 C7 S1 105.70(19) . . ?
N1 C22 C17 120.8(3) . . ?
N1 C22 C21 122.0(3) . . ?
C17 C22 C21 117.2(3) . . ?
C13 C8 C9 117.1(3) . . ?
C13 C8 C7 123.1(3) . . ?
C9 C8 C7 119.8(3) . . ?
N3 C27 C28 121.8(3) . . ?
N3 C27 C26 121.9(3) . . ?
C28 C27 C26 116.3(3) . . ?
C26 C25 C24 122.3(3) . . ?
C29 C28 C27 121.6(3) . . ?
C25 C26 C27 121.3(3) . . ?
C4 C5 C6 120.5(4) . . ?
C18 C17 C22 121.0(3) . . ?
C18 C17 S1 120.2(3) . . ?
C22 C17 S1 118.8(2) . . ?
C20 C21 C22 121.0(4) . . ?
C1 C2 C3 119.9(4) . . ?
C10 C9 C8 121.9(4) . . ?
C3 C4 C5 121.4(4) . . ?
C12 C13 C8 121.5(4) . . ?
C19 C20 C21 120.9(4) . . ?
C9 C10 C11 120.7(4) . . ?
C19 C18 C17 120.4(4) . . ?
C15 N4 C11 119.1(5) . . ?
C15 N4 C14 116.2(5) . . ?
C11 N4 C14 118.2(5) . . ?
C10 C11 C12 117.4(3) . . ?
C10 C11 N4 120.8(5) . . ?
C12 C11 N4 121.8(4) . . ?
C4 C3 C2 119.4(4) . . ?
C13 C12 C11 121.4(4) . . ?
C20 C19 C18 119.5(4) . . ?
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
S2 C1 1.749(3) . ?
S2 C23 1.868(3) . ?
S1 C17 1.753(3) . ?
S1 C7 1.877(3) . ?
N1 C22 1.395(4) . ?
N1 C32 1.461(4) . ?
N1 C23 1.467(4) . ?
N2 C6 1.388(4) . ?
N2 C16 1.463(4) . ?
N2 C7 1.464(4) . ?
C24 C29 1.390(4) . ?
C24 C25 1.397(4) . ?
C24 C23 1.523(4) . ?
N3 C27 1.378(4) . ?
N3 C31 1.440(5) . ?
N3 C30 1.448(5) . ?
C23 C7 1.569(4) . ?
C6 C1 1.400(5) . ?
C6 C5 1.406(4) . ?
C1 C2 1.392(5) . ?
C29 C28 1.378(4) . ?
C7 C8 1.529(4) . ?
C22 C17 1.400(5) . ?
C22 C21 1.406(4) . ?
C8 C13 1.387(5) . ?
C8 C9 1.389(5) . ?
C27 C28 1.402(4) . ?
C27 C26 1.406(4) . ?
C25 C26 1.373(4) . ?
C5 C4 1.376(5) . ?
C17 C18 1.390(5) . ?
C21 C20 1.384(5) . ?
C2 C3 1.396(6) . ?
C9 C10 1.383(5) . ?
C4 C3 1.372(6) . ?
C13 C12 1.377(5) . ?
C20 C19 1.367(6) . ?
C10 C11 1.392(6) . ?
C18 C19 1.382(6) . ?
N4 C15 1.398(7) . ?
N4 C11 1.406(5) . ?
N4 C14 1.464(8) . ?
C11 C12 1.394(6) . ?
