#------------------------------------------------------------------------------
#$Date: 2023-06-05 23:53:50 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284357 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/92/1569282.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_1569282
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         'C6 H Br N4 S2'
_chemical_formula_sum            'C6 H Br N4 S2'
_chemical_formula_weight         273.14
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-01-18
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.562(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5976(3)
_cell_length_b                   9.2941(2)
_cell_length_c                   6.9912(2)
_cell_measurement_reflns_used    10519
_cell_measurement_temperature    99.97(18)
_cell_measurement_theta_max      35.7150
_cell_measurement_theta_min      2.7300
_cell_volume                     795.73(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_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)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(18)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.914
_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   9.00   0.50    8.00    --  -17.65  95.00   7.00  114
  2  ω    -31.00  48.00   0.50    8.00    --   17.96 -95.00-102.00  158
  3  ω    -28.00  55.00   0.50    8.00    --  -17.65  38.00-150.00  166
  4  ω      4.00  90.00   0.50    8.00    --   17.96  57.00   0.00  172
  5  ω    -56.00   5.00   0.50    8.00    --   17.96 -19.00-180.00  122
  6  ω    -56.00   5.00   0.50    8.00    --   17.96 -19.00 -60.00  122
  7  ω     -4.00  90.00   0.50    8.00    --   17.96  77.00 120.00  188
  8  ω     42.00  73.00   0.50    8.00    --   17.96 178.00-150.00   62
  9  ω      7.00  90.00   0.50    8.00    --   17.96  38.00 -90.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0438338000
_diffrn_orient_matrix_UB_12      0.0480339000
_diffrn_orient_matrix_UB_13      0.0005976000
_diffrn_orient_matrix_UB_21      0.0375680000
_diffrn_orient_matrix_UB_22      -0.0526701000
_diffrn_orient_matrix_UB_23      0.0484324000
_diffrn_orient_matrix_UB_31      0.0046575000
_diffrn_orient_matrix_UB_32      -0.0272748000
_diffrn_orient_matrix_UB_33      -0.0924293000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19591
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.819
_diffrn_reflns_theta_min         2.751
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0286
_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)+(0.0338P)²+0.6678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0675
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2983
_reflns_number_total             3403
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            2256390.cif
_cod_data_source_block           tim-47
_cod_database_code               1569282
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C6HBrN4S2
_chemical_oxdiff_usercomment     Tim-47
_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.
;
_olex2_refinement_description
;
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.689
_oxdiff_exptl_absorpt_empirical_full_min 0.485
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
Br1 Br 0.46883(2) 0.35845(2) 0.71135(3) 0.01600(5) Uani 1 1 d . . . . .
S1 S 0.13471(3) 0.00005(4) 0.41981(6) 0.01131(7) Uani 1 1 d . . . . .
S2 S 0.28444(3) 0.63021(4) 0.54488(6) 0.01243(8) Uani 1 1 d . . . . .
N1 N 0.32744(11) 0.06597(15) 0.5930(2) 0.0128(2) Uani 1 1 d . . . . .
N2 N 0.26554(11) -0.04278(15) 0.5403(2) 0.0133(2) Uani 1 1 d . . . . .
N3 N 0.09080(11) 0.56411(14) 0.3782(2) 0.0128(2) Uani 1 1 d . . . . .
N4 N 0.15236(12) 0.67301(15) 0.4320(2) 0.0140(3) Uani 1 1 d . . . . .
C1 C 0.32328(13) 0.33167(16) 0.5810(2) 0.0107(3) Uani 1 1 d . . . . .
C2 C 0.27466(12) 0.19626(16) 0.5408(2) 0.0105(2) Uani 1 1 d . . . . .
C3 C 0.16297(13) 0.18137(16) 0.4413(2) 0.0098(2) Uani 1 1 d . . . . .
C4 C 0.09519(12) 0.29826(16) 0.3811(2) 0.0103(2) Uani 1 1 d . . . . .
H4 H 0.0208(17) 0.285(2) 0.317(3) 0.008(5) Uiso 1 1 d . . . . .
C5 C 0.14437(12) 0.43339(16) 0.4237(2) 0.0108(3) Uani 1 1 d . . . . .
C6 C 0.25603(12) 0.44967(16) 0.5196(2) 0.0105(2) 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
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'
Br Br -0.2901 2.4595 '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 C3 91.67(7) . . ?
N4 S2 C6 91.32(7) . . ?
N2 N1 C2 113.09(13) . . ?
N1 N2 S1 114.20(11) . . ?
N4 N3 C5 113.37(14) . . ?
N3 N4 S2 114.14(11) . . ?
C2 C1 Br1 123.56(11) . . ?
C6 C1 Br1 120.27(11) . . ?
C6 C1 C2 116.17(14) . . ?
N1 C2 C1 124.86(14) . . ?
N1 C2 C3 113.67(14) . . ?
C1 C2 C3 121.47(14) . . ?
C2 C3 S1 107.36(11) . . ?
C4 C3 S1 129.89(12) . . ?
C4 C3 C2 122.74(14) . . ?
C3 C4 H4 120.7(14) . . ?
C3 C4 C5 115.36(14) . . ?
C5 C4 H4 123.9(14) . . ?
N3 C5 C4 124.62(14) . . ?
N3 C5 C6 112.93(14) . . ?
C4 C5 C6 122.45(14) . . ?
C1 C6 S2 129.94(12) . . ?
C1 C6 C5 121.80(14) . . ?
C5 C6 S2 108.24(11) . . ?
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 C1 1.8630(16) . ?
S1 N2 1.7127(14) . ?
S1 C3 1.7217(15) . ?
S2 N4 1.7128(15) . ?
S2 C6 1.7161(15) . ?
N1 N2 1.277(2) . ?
N1 C2 1.388(2) . ?
N3 N4 1.2769(19) . ?
N3 C5 1.390(2) . ?
C1 C2 1.399(2) . ?
C1 C6 1.391(2) . ?
C2 C3 1.423(2) . ?
C3 C4 1.385(2) . ?
C4 H4 0.95(2) . ?
C4 C5 1.401(2) . ?
C5 C6 1.417(2) . ?
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 C1 C2 N1 0.4(2) . . . . ?
Br1 C1 C2 C3 179.79(12) . . . . ?
Br1 C1 C6 S2 -0.4(2) . . . . ?
Br1 C1 C6 C5 -178.68(12) . . . . ?
S1 C3 C4 C5 179.26(12) . . . . ?
N1 C2 C3 S1 -0.71(17) . . . . ?
N1 C2 C3 C4 178.32(14) . . . . ?
N2 S1 C3 C2 0.61(12) . . . . ?
N2 S1 C3 C4 -178.33(16) . . . . ?
N2 N1 C2 C1 179.84(16) . . . . ?
N2 N1 C2 C3 0.45(19) . . . . ?
N3 C5 C6 S2 0.04(17) . . . . ?
N3 C5 C6 C1 178.67(14) . . . . ?
N4 S2 C6 C1 -178.40(16) . . . . ?
N4 S2 C6 C5 0.08(12) . . . . ?
N4 N3 C5 C4 179.76(15) . . . . ?
N4 N3 C5 C6 -0.2(2) . . . . ?
C1 C2 C3 S1 179.87(13) . . . . ?
C1 C2 C3 C4 -1.1(2) . . . . ?
C2 N1 N2 S1 0.05(17) . . . . ?
C2 C1 C6 S2 178.93(13) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 S1 N2 N1 -0.41(13) . . . . ?
C3 C4 C5 N3 -179.25(15) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C4 C5 C6 S2 -179.91(12) . . . . ?
C4 C5 C6 C1 -1.3(2) . . . . ?
C5 N3 N4 S2 0.25(18) . . . . ?
C6 S2 N4 N3 -0.19(13) . . . . ?
C6 C1 C2 N1 -178.84(15) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
