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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/7/15/98/7159874.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_7159874
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            'C28 H24 N2 S2'
_chemical_formula_weight         452.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-10-14 deposited with the CCDC.	2024-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.947(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.936(2)
_cell_length_b                   7.9150(11)
_cell_length_c                   20.365(3)
_cell_measurement_reflns_used    4232
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.78
_cell_volume                     2263.1(6)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(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  0.1099
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            29482
_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         27.531
_diffrn_reflns_theta_min         2.785
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5592
_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    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             952.0
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.223
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.223
_refine_ls_R_factor_all          0.1691
_refine_ls_R_factor_gt           0.0775
_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+0.4089P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1883
_refine_ls_wR_factor_ref         0.2531
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2569
_reflns_number_total             5213
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01871g2.cif
_cod_data_source_block           '[Ph_MBTiazine]2'
_cod_original_cell_volume        2263.2(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159874
_shelx_shelxl_version_number     2018/3
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.33025(8) 0.11686(13) 0.69501(5) 0.0548(3) Uani 1 1 d . . . . .
S2 S 0.40904(8) 0.40670(17) 0.53744(6) 0.0710(4) Uani 1 1 d . . . . .
N1 N 0.2652(2) 0.3872(4) 0.60811(17) 0.0532(8) Uani 1 1 d . . . . .
N2 N 0.3463(2) 0.0895(5) 0.55310(18) 0.0588(9) Uani 1 1 d . . . . .
C8 C 0.4208(3) 0.4143(5) 0.7026(2) 0.0503(10) Uani 1 1 d . . . . .
C7 C 0.3548(3) 0.3004(5) 0.64646(19) 0.0490(9) Uani 1 1 d . . . . .
C6 C 0.2264(3) 0.4040(5) 0.5362(2) 0.0524(10) Uani 1 1 d . . . . .
C28 C 0.4024(3) 0.2253(5) 0.5950(2) 0.0527(10) Uani 1 1 d . . . . .
C14 C 0.2461(3) 0.0242(5) 0.6228(2) 0.0533(10) Uani 1 1 d . . . . .
C20 C 0.5052(3) 0.1676(6) 0.6309(2) 0.0552(10) Uani 1 1 d . . . . .
C19 C 0.2629(3) 0.0213(5) 0.5587(2) 0.0533(10) Uani 1 1 d . . . . .
C5 C 0.1292(3) 0.4145(5) 0.5016(2) 0.0607(11) Uani 1 1 d . . . . .
H5 H 0.087948 0.401434 0.526575 0.073 Uiso 1 1 calc R U . . .
C13 C 0.4918(3) 0.3477(5) 0.7611(2) 0.0577(11) Uani 1 1 d . . . . .
H13 H 0.499578 0.231194 0.765206 0.069 Uiso 1 1 calc R U . . .
C1 C 0.2854(3) 0.4204(5) 0.4952(2) 0.0584(11) Uani 1 1 d . . . . .
C4 C 0.0921(3) 0.4442(5) 0.4300(3) 0.0670(12) Uani 1 1 d . . . . .
H4 H 0.026491 0.453295 0.408343 0.080 Uiso 1 1 calc R U . . .
C9 C 0.4109(3) 0.5906(5) 0.6988(2) 0.0633(12) Uani 1 1 d . . . . .
H9 H 0.365043 0.639800 0.660447 0.076 Uiso 1 1 calc R U . . .
C12 C 0.5505(3) 0.4497(6) 0.8127(2) 0.0639(12) Uani 1 1 d . . . . .
H12 H 0.598110 0.402144 0.850439 0.077 Uiso 1 1 calc R U . . .
C21 C 0.5238(3) -0.0016(6) 0.6477(2) 0.0636(12) Uani 1 1 d . . . . .
H21 H 0.473367 -0.077574 0.637648 0.076 Uiso 1 1 calc R U . . .
C18 C 0.1951(3) -0.0581(5) 0.5021(2) 0.0636(12) Uani 1 1 d . . . . .
H18 H 0.205218 -0.065506 0.459566 0.076 Uiso 1 1 calc R U . . .
C26 C 0.2036(3) 0.4260(6) 0.6486(2) 0.0709(13) Uani 1 1 d . . . . .
H26A H 0.173368 0.533355 0.634108 0.106 Uiso 1 1 calc R U . . .
H26B H 0.241013 0.430196 0.697328 0.106 Uiso 1 1 calc R U . . .
H26C H 0.155795 0.339845 0.640781 0.106 Uiso 1 1 calc R U . . .
C3 C 0.1504(4) 0.4605(6) 0.3907(3) 0.0737(13) Uani 1 1 d . . . . .
H3 H 0.125349 0.481274 0.342946 0.088 Uiso 1 1 calc R U . . .
C15 C 0.1625(3) -0.0420(6) 0.6276(3) 0.0657(12) Uani 1 1 d . . . . .
H15 H 0.150794 -0.034672 0.669586 0.079 Uiso 1 1 calc R U . . .
C25 C 0.5829(3) 0.2770(6) 0.6453(2) 0.0683(12) Uani 1 1 d . . . . .
H25 H 0.572581 0.391035 0.634355 0.082 Uiso 1 1 calc R U . . .
C2 C 0.2475(4) 0.4449(6) 0.4244(3) 0.0724(13) Uani 1 1 d . . . . .
H2 H 0.288002 0.451164 0.398540 0.087 Uiso 1 1 calc R U . . .
C11 C 0.5385(4) 0.6230(6) 0.8083(3) 0.0729(13) Uani 1 1 d . . . . .
H11 H 0.577401 0.692080 0.843435 0.087 Uiso 1 1 calc R U . . .
C10 C 0.4694(4) 0.6928(6) 0.7522(3) 0.0729(13) Uani 1 1 d . . . . .
H10 H 0.461269 0.809424 0.749649 0.088 Uiso 1 1 calc R U . . .
C17 C 0.1131(4) -0.1260(6) 0.5086(3) 0.0750(14) Uani 1 1 d . . . . .
H17 H 0.068356 -0.177529 0.470364 0.090 Uiso 1 1 calc R U . . .
C16 C 0.0971(4) -0.1180(6) 0.5711(3) 0.0741(14) Uani 1 1 d . . . . .
H16 H 0.041921 -0.164256 0.575034 0.089 Uiso 1 1 calc R U . . .
C24 C 0.6748(3) 0.2178(8) 0.6757(2) 0.0770(14) Uani 1 1 d . . . . .
H24 H 0.725737 0.292329 0.684441 0.092 Uiso 1 1 calc R U . . .
C22 C 0.6164(4) -0.0595(6) 0.6795(2) 0.0721(13) Uani 1 1 d . . . . .
H22 H 0.627562 -0.172872 0.691596 0.087 Uiso 1 1 calc R U . . .
C23 C 0.6919(4) 0.0517(8) 0.6931(3) 0.0806(15) Uani 1 1 d . . . . .
H23 H 0.754063 0.013361 0.714019 0.097 Uiso 1 1 calc R U . . .
C27 C 0.3712(4) 0.0359(7) 0.4925(2) 0.0812(15) Uani 1 1 d . . . . .
H27A H 0.364626 -0.084440 0.487270 0.122 Uiso 1 1 calc R U . . .
H27B H 0.435873 0.067343 0.499352 0.122 Uiso 1 1 calc R U . . .
H27C H 0.329454 0.089893 0.451140 0.122 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
C14 S1 C7 95.57(18) . . ?
C1 S2 C28 94.72(18) . . ?
C6 N1 C26 117.3(3) . . ?
C6 N1 C7 125.7(3) . . ?
C26 N1 C7 115.7(3) . . ?
C19 N2 C28 126.3(3) . . ?
C19 N2 C27 116.5(4) . . ?
C28 N2 C27 116.6(3) . . ?
C13 C8 C9 117.2(4) . . ?
C13 C8 C7 121.6(4) . . ?
C9 C8 C7 121.2(4) . . ?
N1 C7 C8 111.1(3) . . ?
N1 C7 C28 111.1(3) . . ?
C8 C7 C28 113.6(3) . . ?
N1 C7 S1 109.7(2) . . ?
C8 C7 S1 104.9(2) . . ?
C28 C7 S1 106.0(3) . . ?
C5 C6 N1 122.2(4) . . ?
C5 C6 C1 116.8(4) . . ?
N1 C6 C1 120.9(4) . . ?
N2 C28 C20 110.2(3) . . ?
N2 C28 C7 111.8(3) . . ?
C20 C28 C7 113.8(3) . . ?
N2 C28 S2 110.1(3) . . ?
C20 C28 S2 105.6(3) . . ?
C7 C28 S2 105.1(3) . . ?
C15 C14 C19 120.5(4) . . ?
C15 C14 S1 120.5(3) . . ?
C19 C14 S1 118.9(3) . . ?
C21 C20 C25 117.7(4) . . ?
C21 C20 C28 119.4(4) . . ?
C25 C20 C28 122.9(4) . . ?
N2 C19 C18 121.4(4) . . ?
N2 C19 C14 121.0(4) . . ?
C18 C19 C14 117.6(4) . . ?
C6 C5 C4 121.3(4) . . ?
C12 C13 C8 122.0(4) . . ?
C2 C1 C6 121.2(4) . . ?
C2 C1 S2 120.8(4) . . ?
C6 C1 S2 118.0(3) . . ?
C3 C4 C5 121.3(4) . . ?
C10 C9 C8 120.4(4) . . ?
C13 C12 C11 119.8(4) . . ?
C20 C21 C22 121.1(5) . . ?
C17 C18 C19 120.7(4) . . ?
C4 C3 C2 117.9(5) . . ?
C16 C15 C14 120.5(4) . . ?
C24 C25 C20 120.8(5) . . ?
C1 C2 C3 121.5(5) . . ?
C10 C11 C12 120.0(4) . . ?
C11 C10 C9 120.6(4) . . ?
C16 C17 C18 120.7(5) . . ?
C15 C16 C17 120.0(4) . . ?
C23 C24 C25 120.8(5) . . ?
C23 C22 C21 119.8(5) . . ?
C24 C23 C22 119.7(5) . . ?
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 C14 1.738(4) . ?
S1 C7 1.863(4) . ?
S2 C1 1.755(5) . ?
S2 C28 1.877(4) . ?
N1 C6 1.386(5) . ?
N1 C26 1.462(5) . ?
N1 C7 1.470(5) . ?
N2 C19 1.398(5) . ?
N2 C28 1.448(5) . ?
N2 C27 1.469(5) . ?
C8 C13 1.400(6) . ?
C8 C9 1.402(6) . ?
C8 C7 1.524(5) . ?
C7 C28 1.570(5) . ?
C6 C5 1.383(6) . ?
C6 C1 1.411(6) . ?
C28 C20 1.528(6) . ?
C14 C15 1.388(6) . ?
C14 C19 1.411(6) . ?
C20 C21 1.387(6) . ?
C20 C25 1.396(6) . ?
C19 C18 1.398(6) . ?
C5 C4 1.390(6) . ?
C13 C12 1.377(6) . ?
C1 C2 1.371(6) . ?
C4 C3 1.376(7) . ?
C9 C10 1.398(6) . ?
C12 C11 1.382(6) . ?
C21 C22 1.391(6) . ?
C18 C17 1.386(6) . ?
C3 C2 1.381(7) . ?
C15 C16 1.368(6) . ?
C25 C24 1.382(6) . ?
C11 C10 1.368(7) . ?
C17 C16 1.374(6) . ?
C24 C23 1.363(7) . ?
C22 C23 1.382(7) . ?
