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#$Date: 2022-03-05 00:18:01 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273383 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/12/7061217.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_7061217
loop_
_publ_author_name
'Makarov, Alexander Yu.'
'Volkova, Yulia M.'
'Zikirin, Samat B.'
'Irtegova, Irina G.'
'Bagryanskaya, Irina Yu.'
'Gatilov, Yuri V.'
'Nefedov, Andrey A.'
'Zibarev, Andrey V.'
_publ_section_title
;
 New 3,1,2,4-benzothiaselenadiazines, related π-heterocycles including
 Herz cations, radicals and molecular complexes, and Bunte salts
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3687
_journal_page_last               3696
_journal_paper_doi               10.1039/D1NJ05979C
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C14 H20 N S2, Cl'
_chemical_formula_sum            'C14 H20 Cl N S2'
_chemical_formula_weight         301.88
_chemical_name_systematic
;
  4,7-Di-tert-butyl-1,2,3-benzodithiazolium chloride 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-10-15 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.119(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6876(18)
_cell_length_b                   7.0309(14)
_cell_length_c                   20.882(6)
_cell_measurement_reflns_used    1962
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.66
_cell_measurement_theta_min      3.47
_cell_volume                     1562.9(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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_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  0.1021
_diffrn_reflns_av_unetI/netI     0.1549
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12917
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.022
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         0.979
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.495
_exptl_absorpt_correction_T_max  0.9280
_exptl_absorpt_correction_T_min  0.7702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1502
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0931
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0665P)²+8.8056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2361
_refine_ls_wR_factor_ref         0.2457
_reflns_Friedel_coverage         0.000
_reflns_number_gt                857
_reflns_number_total             1502
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj05979c2.cif
_cod_data_source_block           25_vim225
_cod_depositor_comments
'Adding full bibliography for 7061215--7061218.cif.'
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7061217
_shelx_shelxl_version_number     2014/7
_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
S1 S 0.0988(2) 0.0000 0.20798(13) 0.0417(8) Uani 1 2 d S T P . .
S2 S 0.1705(2) 0.0000 0.29990(14) 0.0443(9) Uani 1 2 d S T P . .
N3 N 0.0441(7) 0.0000 0.3337(4) 0.044(2) Uani 1 2 d S TU P . .
C10 C -0.0914(12) 0.1768(16) 0.0873(4) 0.103(4) Uani 1 1 d . . . . .
H10C H -0.0896 0.1743 0.0414 0.154 Uiso 1 1 calc R U . . .
H10B H -0.1347 0.2889 0.0995 0.154 Uiso 1 1 calc R U . . .
H10A H -0.0070 0.1780 0.1073 0.154 Uiso 1 1 calc R U . . .
C8 C -0.1598(12) 0.0000 0.1090(5) 0.053(3) Uani 1 2 d S T P . .
C7 C -0.1641(10) 0.0000 0.1808(5) 0.038(3) Uani 1 2 d S T P . .
C6 C -0.2749(8) 0.0000 0.2094(4) 0.030(2) Uani 1 2 d S T P . .
H6 H -0.3487 0.0000 0.1822 0.036 Uiso 1 2 calc R U P . .
C5 C -0.2874(9) 0.0000 0.2754(5) 0.041(3) Uani 1 2 d S T P . .
H5 H -0.3673 0.0000 0.2898 0.049 Uiso 1 2 calc R U P . .
C4 C -0.1823(8) 0.0000 0.3202(5) 0.035(2) Uani 1 2 d S TU P . .
C11 C -0.1962(10) 0.0000 0.3936(5) 0.042(3) Uani 1 2 d S T P . .
C12 C -0.3352(12) 0.0000 0.4073(7) 0.058(4) Uani 1 2 d S T P . .
H12B H -0.340(12) 0.0000 0.453(6) 0.087 Uiso 1 2 d S U P . .
H12A H -0.375(8) 0.097(13) 0.382(4) 0.087 Uiso 1 1 d . U . . .
C13 C -0.1356(8) -0.1772(13) 0.4246(4) 0.062(2) Uani 1 1 d . . . . .
H13C H -0.1743 -0.2883 0.4048 0.093 Uiso 1 1 calc R U . . .
H13B H -0.0475 -0.1776 0.4188 0.093 Uiso 1 1 calc R U . . .
H13A H -0.1468 -0.1776 0.4697 0.093 Uiso 1 1 calc R U . . .
C7A C -0.0572(8) 0.0000 0.2271(5) 0.027(2) Uani 1 2 d S TU P . .
C9 C -0.2900(19) 0.0000 0.0726(8) 0.100(7) Uani 1 2 d S T P . .
H9B H -0.299(13) -0.12(2) 0.084(6) 0.150 Uiso 1 1 d . U . . .
H9A H -0.280(18) 0.0000 0.030(9) 0.150 Uiso 1 2 d S U P . .
C3A C -0.0668(7) 0.0000 0.2950(5) 0.0271(19) Uani 1 2 d S TU P . .
Cl1 Cl -0.1120(3) 0.5000 0.23332(17) 0.0656(11) Uani 1 2 d S T P . .
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'
Cl Cl 0.1484 0.1585 '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
C7A S1 S2 94.1(3) . . ?
N3 S2 S1 99.2(3) . . ?
C3A N3 S2 117.7(7) . . ?
C8 C10 H10C 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10C C10 H10B 109.5 . . ?
C8 C10 H10A 109.5 . . ?
H10C C10 H10A 109.5 . . ?
H10B C10 H10A 109.5 . . ?
C7 C8 C9 113.0(11) . . ?
C7 C8 C10 110.7(7) . 6 ?
C9 C8 C10 106.9(8) . 6 ?
C7 C8 C10 110.7(7) . . ?
C9 C8 C10 106.9(8) . . ?
C10 C8 C10 108.5(12) 6 . ?
C6 C7 C7A 112.0(8) . . ?
C6 C7 C8 122.5(9) . . ?
C7A C7 C8 125.5(9) . . ?
C7 C6 C5 126.2(9) . . ?
C7 C6 H6 116.9 . . ?
C5 C6 H6 116.9 . . ?
C6 C5 C4 121.3(8) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C3A C4 C5 115.9(9) . . ?
C3A C4 C11 122.8(8) . . ?
C5 C4 C11 121.3(8) . . ?
C13 C11 C13 110.0(10) 6 . ?
C13 C11 C4 110.2(6) 6 . ?
C13 C11 C4 110.2(6) . . ?
C13 C11 C12 107.6(6) 6 . ?
C13 C11 C12 107.6(6) . . ?
C4 C11 C12 111.2(9) . . ?
C11 C12 H12B 109(8) . . ?
C11 C12 H12A 107(6) . . ?
H12B C12 H12A 120(7) . . ?
C11 C13 H13C 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13C C13 H13B 109.5 . . ?
C11 C13 H13A 109.5 . . ?
H13C C13 H13A 109.5 . . ?
H13B C13 H13A 109.5 . . ?
C3A C7A C7 123.1(8) . . ?
C3A C7A S1 112.4(6) . . ?
C7 C7A S1 124.5(7) . . ?
C8 C9 H9B 89(10) . . ?
C8 C9 H9A 108(10) . . ?
H9B C9 H9A 107(9) . . ?
N3 C3A C4 121.9(9) . . ?
N3 C3A C7A 116.6(7) . . ?
C4 C3A C7A 121.5(8) . . ?
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 C7A 1.749(9) . ?
S1 S2 2.002(4) . ?
S2 N3 1.579(8) . ?
N3 C3A 1.374(12) . ?
C10 C8 1.532(12) . ?
C10 H10C 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10A 0.9600 . ?
C8 C7 1.505(14) . ?
C8 C9 1.53(2) . ?
C8 C10 1.532(12) 6 ?
C7 C6 1.373(13) . ?
C7 C7A 1.429(13) . ?
C6 C5 1.398(13) . ?
C6 H6 0.9300 . ?
C5 C4 1.396(14) . ?
C5 H5 0.9300 . ?
C4 C3A 1.384(12) . ?
C4 C11 1.554(14) . ?
C11 C13 1.521(10) 6 ?
C11 C13 1.521(10) . ?
C11 C12 1.538(16) . ?
C12 H12B 0.96(12) . ?
C12 H12A 0.95(9) . ?
C13 H13C 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13A 0.9600 . ?
C7A C3A 1.430(13) . ?
C9 H9B 0.89(14) . ?
C9 H9A 0.91(17) . ?
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
S1 S2 N3 C3A 0.000(1) . . . . ?
C9 C8 C7 C6 0.000(1) . . . . ?
C10 C8 C7 C6 -119.8(8) 6 . . . ?
C10 C8 C7 C6 119.8(8) . . . . ?
C9 C8 C7 C7A 180.000(1) . . . . ?
C10 C8 C7 C7A 60.2(8) 6 . . . ?
C10 C8 C7 C7A -60.2(8) . . . . ?
C7A C7 C6 C5 0.000(1) . . . . ?
C8 C7 C6 C5 180.000(1) . . . . ?
C7 C6 C5 C4 0.000(2) . . . . ?
C6 C5 C4 C3A 0.000(2) . . . . ?
C6 C5 C4 C11 180.000(2) . . . . ?
C3A C4 C11 C13 60.8(6) . . . 6 ?
C5 C4 C11 C13 -119.2(6) . . . 6 ?
C3A C4 C11 C13 -60.8(6) . . . . ?
C5 C4 C11 C13 119.2(6) . . . . ?
C3A C4 C11 C12 180.000(2) . . . . ?
C5 C4 C11 C12 0.000(3) . . . . ?
C6 C7 C7A C3A 0.000(1) . . . . ?
C8 C7 C7A C3A 180.000(1) . . . . ?
C6 C7 C7A S1 180.000(1) . . . . ?
C8 C7 C7A S1 0.000(1) . . . . ?
S2 S1 C7A C3A 0.000(1) . . . . ?
S2 S1 C7A C7 180.000(1) . . . . ?
S2 N3 C3A C4 180.000(1) . . . . ?
S2 N3 C3A C7A 0.000(2) . . . . ?
C5 C4 C3A N3 180.000(1) . . . . ?
C11 C4 C3A N3 0.000(2) . . . . ?
C5 C4 C3A C7A 0.000(2) . . . . ?
C11 C4 C3A C7A 180.000(2) . . . . ?
C7 C7A C3A N3 180.000(1) . . . . ?
S1 C7A C3A N3 0.000(1) . . . . ?
C7 C7A C3A C4 0.000(2) . . . . ?
S1 C7A C3A C4 180.000(1) . . . . ?
