#------------------------------------------------------------------------------
#$Date: 2023-06-05 23:53:02 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284355 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/92/1569280.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_1569280
loop_
_publ_author_name
'Chmovzh, Timofey N.'
'Alekhina, Daria A.'
'Kudryashev, Timofey A.'
'Aysin, Rinat R.'
'Korlyukov, Alexander A.'
'Rakitin, Oleg A.'
_publ_section_title
;
 Benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole) and Its Bromo
 Derivatives: Molecular Structure and Reactivity.
;
_journal_issue                   10
_journal_name_full               'International journal of molecular sciences'
_journal_page_first              8835
_journal_paper_doi               10.3390/ijms24108835
_journal_volume                  24
_journal_year                    2023
_chemical_formula_moiety         '2(Br C3 N2 S)'
_chemical_formula_sum            'C6 Br2 N4 S2'
_chemical_formula_weight         352.04
_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'
_audit_creation_date             2023-05-08
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                90
_cell_angle_beta                 119.312(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1779(4)
_cell_length_b                   3.88730(10)
_cell_length_c                   16.1804(4)
_cell_measurement_reflns_used    22563
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      35.5890
_cell_measurement_theta_min      2.8630
_cell_volume                     887.28(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -48.00   6.25   0.35    3.00    --  -17.87  96.00 -89.00  155
  2  ω    -29.00  48.00   0.35    3.00    --   18.03 -96.00 161.00  220
  3  ω    -29.00  55.70   0.35    3.00    --  -17.87  19.00-120.00  242
  4  ω    -90.00  -8.10   0.35    3.00    --  -17.87 -38.00 -30.00  234
  5  ω    -90.00  -5.30   0.35    3.00    --  -17.87 -57.00-120.00  242
  6  ω    -56.00   4.20   0.35    3.00    --   18.03 -19.00 120.00  172
  7  ω     -4.00  89.10   0.35    3.00    --   18.03  77.00 150.00  266
  8  ω     39.00  88.70   0.35    3.00    --   18.03-178.00  60.00  142
  9  ω      4.00  88.70   0.35    3.00    --   18.03  57.00  60.00  242
 10  ω    -56.00   4.20   0.35    3.00    --   18.03 -19.00-150.00  172
 11  ω    -32.00  52.70   0.35    3.00    --  -17.87  57.00  30.00  242
 12  ω      7.00  88.90   0.35    3.00    --   18.03  38.00-180.00  234
 13  ω    -23.00  49.10   0.35    3.00    --   18.03 -99.00-150.00  206
 14  ω    -23.00  49.10   0.35    3.00    --   18.03 -99.00 -90.00  206
 15  ω      4.00  88.70   0.35    3.00    --   18.03  57.00 -90.00  242
 16  ω    -23.00   2.20   0.35    3.00    --   18.03 -99.00  30.00   72
 17  ω    -54.00  21.25   0.35    3.00    --   18.03 -38.00  60.00  215
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28713
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_min         2.492
_exptl_absorpt_coefficient_mu    9.562
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.635
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         2.192
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0390
_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)+(0.0786P)²+0.9573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1906
_reflns_number_total             1924
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            2210625.cif
_cod_data_source_block           tim-31
_cod_original_cell_volume        887.28(4)
_cod_database_code               1569280
_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.
;
_shelx_estimated_absorpt_t_max   0.251
_shelx_estimated_absorpt_t_min   0.075
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.521(3)
 0.479(3)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
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
Br1 Br 0.86029(4) 0.7653(2) 0.28005(3) 0.01395(17) Uani 1 1 d . . . . .
Br2 Br 0.28025(3) 1.27244(16) 0.36306(4) 0.01523(17) Uani 1 1 d . . . . .
S1 S 0.89112(9) 0.1730(3) 0.59135(9) 0.0187(3) Uani 1 1 d . . . . .
S2 S 0.59219(10) 0.7061(5) 0.38832(10) 0.0196(4) Uani 1 1 d . . . . .
N1 N 0.8070(3) 0.3973(11) 0.4245(3) 0.0192(9) Uani 1 1 d . . . . .
N2 N 0.7913(4) 0.2493(10) 0.4867(4) 0.0160(9) Uani 1 1 d . . . . .
N3 N 0.4254(3) 0.9313(11) 0.3067(3) 0.0231(9) Uani 1 1 d . . . . .
N4 N 0.4856(4) 0.7866(10) 0.2892(3) 0.0205(9) Uani 1 1 d . . . . .
C1 C 1.0383(3) 0.6560(12) 0.4491(3) 0.0171(9) Uani 1 1 d . . . . .
C2 C 0.9397(3) 0.6142(12) 0.4043(3) 0.0171(9) Uani 1 1 d . . . . .
C3 C 0.9029(3) 0.4577(12) 0.4567(3) 0.0168(8) Uani 1 1 d . . . . .
C4 C 0.4473(3) 1.1429(13) 0.5376(4) 0.0207(10) Uani 1 1 d . . . . .
C5 C 0.4036(3) 1.1163(12) 0.4405(3) 0.0192(9) Uani 1 1 d . . . . .
C6 C 0.4569(3) 0.9738(12) 0.4022(3) 0.0192(9) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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
N2 S1 C1 92.2(3) . 3_766 ?
N4 S2 C4 92.5(3) . 3_676 ?
N2 N1 C3 113.1(4) . . ?
N1 N2 S1 113.7(4) . . ?
N4 N3 C6 113.5(4) . . ?
N3 N4 S2 113.8(4) . . ?
C2 C1 S1 130.8(4) . 3_766 ?
C2 C1 C3 121.0(4) . 3_766 ?
C3 C1 S1 108.2(3) 3_766 3_766 ?
C1 C2 Br1 121.8(3) . . ?
C3 C2 Br1 121.2(3) . . ?
C3 C2 C1 117.0(4) . . ?
N1 C3 C1 112.8(4) . 3_766 ?
C2 C3 N1 125.2(4) . . ?
C2 C3 C1 122.0(4) . 3_766 ?
C5 C4 S2 131.7(4) . 3_676 ?
C5 C4 C6 121.9(4) . 3_676 ?
C6 C4 S2 106.4(4) 3_676 3_676 ?
C4 C5 Br2 121.7(3) . . ?
C4 C5 C6 116.9(4) . . ?
C6 C5 Br2 121.4(4) . . ?
N3 C6 C4 113.8(4) . 3_676 ?
N3 C6 C5 125.0(4) . . ?
C5 C6 C4 121.2(4) . 3_676 ?
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
Br1 C2 1.873(4) . ?
Br2 C5 1.864(5) . ?
S1 N2 1.699(5) . ?
S1 C1 1.704(5) 3_766 ?
S2 N4 1.713(5) . ?
S2 C4 1.714(5) 3_676 ?
N1 N2 1.288(6) . ?
N1 C3 1.394(5) . ?
N3 N4 1.270(7) . ?
N3 C6 1.381(6) . ?
C1 C2 1.402(6) . ?
C1 C3 1.415(6) 3_766 ?
C2 C3 1.393(5) . ?
C4 C5 1.376(7) . ?
C4 C6 1.441(6) 3_676 ?
C5 C6 1.399(6) . ?
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
Br1 C2 C3 N1 0.0(6) . . . . ?
Br1 C2 C3 C1 -179.5(3) . . . 3_766 ?
Br2 C5 C6 N3 -0.6(7) . . . . ?
Br2 C5 C6 C4 179.3(4) . . . 3_676 ?
S1 C1 C2 Br1 -1.6(6) 3_766 . . . ?
S1 C1 C2 C3 179.0(4) 3_766 . . . ?
S2 C4 C5 Br2 2.4(7) 3_676 . . . ?
S2 C4 C5 C6 -179.1(4) 3_676 . . . ?
N2 N1 C3 C1 -0.3(6) . . . 3_766 ?
N2 N1 C3 C2 -179.9(4) . . . . ?
N4 N3 C6 C4 2.1(6) . . . 3_676 ?
N4 N3 C6 C5 -178.0(5) . . . . ?
C1 S1 N2 N1 -0.9(4) 3_766 . . . ?
C1 C2 C3 N1 179.4(4) . . . . ?
C1 C2 C3 C1 -0.2(7) . . . 3_766 ?
C3 N1 N2 S1 0.9(5) . . . . ?
C3 C1 C2 Br1 179.5(3) 3_766 . . . ?
C3 C1 C2 C3 0.2(7) 3_766 . . . ?
C4 S2 N4 N3 3.3(4) 3_676 . . . ?
C4 C5 C6 N3 -179.1(5) . . . . ?
C4 C5 C6 C4 0.8(8) . . . 3_676 ?
C6 N3 N4 S2 -3.7(6) . . . . ?
C6 C4 C5 Br2 -179.3(4) 3_676 . . . ?
C6 C4 C5 C6 -0.8(8) 3_676 . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.521(3)
2 0.479(3)
