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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/7/15/98/7159868.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_7159868
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_moiety         'C28 H36 N2 S2'
_chemical_formula_sum            'C28 H36 N2 S2'
_chemical_formula_weight         464.71
_chemical_name_common            '[Cy-MBT]2'
_chemical_name_systematic
2,2'-dicyclohexyl-3,3'-dimethyl-2,2',3,3'-tetrahydro-2,2'-bibenzo[d]thiazole
_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'
_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                 114.621(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.587(4)
_cell_length_b                   9.745(3)
_cell_length_c                   12.647(4)
_cell_measurement_reflns_used    4617
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.97
_cell_volume                     1186.2(7)
_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      295(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.981
_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  0.0443
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10637
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.759
_diffrn_reflns_theta_min         2.975
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5819
_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    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0391
_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)+(0.0362P)²+0.4952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1052
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2241
_reflns_number_total             2795
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01871g2.cif
_cod_data_source_block           '[Cy-MBT]2'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159868
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.48225(5) 0.27931(4) 0.44151(4) 0.03763(14) Uani 1 1 d . . . . .
N1 N 0.43844(14) 0.41083(13) 0.60453(11) 0.0323(3) Uani 1 1 d . . . . .
C1 C 0.36659(17) 0.21142(16) 0.49318(13) 0.0345(3) Uani 1 1 d . . . . .
C2 C 0.35469(16) 0.29609(15) 0.57761(13) 0.0319(3) Uani 1 1 d . . . . .
C3 C 0.26272(17) 0.26045(18) 0.62528(15) 0.0391(4) Uani 1 1 d . . . . .
H3 H 0.251243 0.316967 0.679886 0.047 Uiso 1 1 calc R U . . .
C4 C 0.18791(19) 0.1390(2) 0.59029(16) 0.0483(4) Uani 1 1 d . . . . .
H4 H 0.125498 0.115106 0.621552 0.058 Uiso 1 1 calc R U . . .
C5 C 0.2042(2) 0.0536(2) 0.51050(17) 0.0536(5) Uani 1 1 d . . . . .
H5 H 0.155330 -0.028576 0.490032 0.064 Uiso 1 1 calc R U . . .
C6 C 0.2937(2) 0.09005(18) 0.46050(16) 0.0461(4) Uani 1 1 d . . . . .
H6 H 0.304356 0.033353 0.405636 0.055 Uiso 1 1 calc R U . . .
C7 C 0.52396(16) 0.43161(14) 0.53950(12) 0.0302(3) Uani 1 1 d . . . . .
C8 C 0.68246(16) 0.42375(16) 0.62376(14) 0.0352(3) Uani 1 1 d . . . . .
H8 H 0.706870 0.508638 0.669433 0.042 Uiso 1 1 calc R U . . .
C9 C 0.70764(19) 0.30326(19) 0.70919(15) 0.0449(4) Uani 1 1 d . . . . .
H9A H 0.653464 0.318235 0.753941 0.054 Uiso 1 1 calc R U . . .
H9B H 0.674552 0.219348 0.664984 0.054 Uiso 1 1 calc R U . . .
C10 C 0.8594(2) 0.2846(2) 0.79272(16) 0.0538(5) Uani 1 1 d . . . . .
H10A H 0.889376 0.363079 0.844459 0.065 Uiso 1 1 calc R U . . .
H10B H 0.868297 0.203538 0.839832 0.065 Uiso 1 1 calc R U . . .
C11 C 0.9521(2) 0.2699(2) 0.72994(18) 0.0533(5) Uani 1 1 d . . . . .
H11A H 0.929401 0.185980 0.684591 0.064 Uiso 1 1 calc R U . . .
H11B H 1.048280 0.264565 0.785946 0.064 Uiso 1 1 calc R U . . .
C12 C 0.9328(2) 0.3916(2) 0.6506(2) 0.0560(5) Uani 1 1 d . . . . .
H12A H 0.990319 0.379621 0.608346 0.067 Uiso 1 1 calc R U . . .
H12B H 0.963279 0.474203 0.697144 0.067 Uiso 1 1 calc R U . . .
C13 C 0.78193(18) 0.4087(2) 0.56415(17) 0.0458(4) Uani 1 1 d . . . . .
H13A H 0.754351 0.329582 0.512961 0.055 Uiso 1 1 calc R U . . .
H13B H 0.774087 0.489200 0.516737 0.055 Uiso 1 1 calc R U . . .
C14 C 0.45532(19) 0.49138(18) 0.70624(14) 0.0407(4) Uani 1 1 d . . . . .
H14A H 0.536843 0.547603 0.728623 0.061 Uiso 1 1 calc R U . . .
H14B H 0.464972 0.430974 0.769110 0.061 Uiso 1 1 calc R U . . .
H14C H 0.375300 0.548788 0.688171 0.061 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 93.54(7) . . ?
C2 N1 C14 119.08(13) . . ?
C2 N1 C7 117.16(12) . . ?
C14 N1 C7 122.96(13) . . ?
C6 C1 C2 121.25(16) . . ?
C6 C1 S1 127.39(14) . . ?
C2 C1 S1 111.36(12) . . ?
N1 C2 C3 126.28(15) . . ?
N1 C2 C1 114.49(14) . . ?
C3 C2 C1 119.22(15) . . ?
C2 C3 C4 119.03(16) . . ?
C5 C4 C3 121.37(17) . . ?
C4 C5 C6 119.92(17) . . ?
C1 C6 C5 119.13(17) . . ?
N1 C7 C8 110.30(12) . . ?
N1 C7 C7 110.62(15) . 3_666 ?
C8 C7 C7 115.54(15) . 3_666 ?
N1 C7 S1 103.41(9) . . ?
C8 C7 S1 107.60(10) . . ?
C7 C7 S1 108.62(13) 3_666 . ?
C13 C8 C9 108.50(14) . . ?
C13 C8 C7 115.39(14) . . ?
C9 C8 C7 109.66(13) . . ?
C10 C9 C8 113.70(16) . . ?
C11 C10 C9 112.15(16) . . ?
C10 C11 C12 109.79(16) . . ?
C11 C12 C13 111.93(16) . . ?
C12 C13 C8 112.74(16) . . ?
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 1.7409(17) . ?
S1 C7 1.8649(15) . ?
N1 C2 1.3787(19) . ?
N1 C14 1.4530(19) . ?
N1 C7 1.4687(19) . ?
C1 C6 1.378(2) . ?
C1 C2 1.396(2) . ?
C2 C3 1.386(2) . ?
C3 C4 1.390(3) . ?
C4 C5 1.373(3) . ?
C5 C6 1.386(3) . ?
C7 C8 1.571(2) . ?
C7 C7 1.616(3) 3_666 ?
C8 C13 1.536(2) . ?
C8 C9 1.542(2) . ?
C9 C10 1.522(3) . ?
C10 C11 1.504(3) . ?
C11 C12 1.511(3) . ?
C12 C13 1.523(3) . ?
