# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ishii2002b
_database_code_depnum_ccdc_archive 'CCDC 2234914'
loop_
_audit_author_name
_audit_author_address
'Tsutomu Ishi-i'
;National Institute of Technology, Kurume College
Japan
;
_audit_update_record             
;
2023-01-07 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_audit_creation_date             2020-02-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 Br2 N2 O2 S'
_chemical_formula_sum            'C8 H6 Br2 N2 O2 S'
_chemical_formula_weight         354.03
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
O O 0.0106 0.0060 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   13.7002(7)
_cell_length_b                   4.3371(2)
_cell_length_c                   17.9709(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.883(4)
_cell_angle_gamma                90
_cell_volume                     1067.69(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4760
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.2830
_cell_measurement_theta_min      2.2320
_shelx_estimated_absorpt_T_max   0.860
_shelx_estimated_absorpt_T_min   0.204
_exptl_absorpt_coefficient_mu    7.767
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8878
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.267
_diffrn_ambient_temperature      100
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00  94.00   0.50    0.50    --    5.00  45.00 150.00  124
  2  ω    -61.00 -35.00   0.50    0.50    --    5.00  45.00 150.00   52
  3  ω     59.00  85.00   0.50    0.50    --    5.00  45.00   0.00   52
  4  ω    -98.00  80.00   0.50    0.50    --   -8.70  45.00  60.00  356
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0265957000
_diffrn_orient_matrix_UB_12      -0.0029902000
_diffrn_orient_matrix_UB_13      0.0335401000
_diffrn_orient_matrix_UB_21      0.0444236000
_diffrn_orient_matrix_UB_22      -0.0011580000
_diffrn_orient_matrix_UB_23      0.0208225000
_diffrn_orient_matrix_UB_31      -0.0003452000
_diffrn_orient_matrix_UB_32      0.1634615000
_diffrn_orient_matrix_UB_33      0.0008813000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2170
_reflns_number_total             2420
_reflns_odcompleteness_completeness 98.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.784
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2420
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²+0.4850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0718
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.91130(2) 0.99975(6) 0.28995(2) 0.01826(10) Uani 1 1 d . . . . .
Br2 Br 0.61475(2) 0.14467(6) 0.48865(2) 0.01887(10) Uani 1 1 d . . . . .
S1 S 0.90585(5) 0.71758(18) 0.54665(4) 0.02179(17) Uani 1 1 d . . . . .
O1 O 0.71098(15) 0.7214(4) 0.24475(10) 0.0169(4) Uani 1 1 d . . . . .
O2 O 0.59478(14) 0.3393(4) 0.32399(11) 0.0172(4) Uani 1 1 d . . . . .
N1 N 0.91762(18) 0.8415(5) 0.46224(13) 0.0191(5) Uani 1 1 d . . . . .
N2 N 0.80869(19) 0.5060(5) 0.53788(14) 0.0196(5) Uani 1 1 d . . . . .
C1 C 0.7811(2) 0.5281(6) 0.46605(15) 0.0154(6) Uani 1 1 d . . . . .
C2 C 0.8436(2) 0.7188(6) 0.42294(15) 0.0163(6) Uani 1 1 d . . . . .
C3 C 0.8229(2) 0.7709(6) 0.34621(15) 0.0149(5) Uani 1 1 d . . . . .
C4 C 0.7390(2) 0.6485(6) 0.31567(15) 0.0142(6) Uani 1 1 d . . . . .
C5 C 0.6758(2) 0.4575(6) 0.35922(15) 0.0151(6) Uani 1 1 d . . . . .
C6 C 0.6971(2) 0.3933(6) 0.43189(15) 0.0158(6) Uani 1 1 d . . . . .
C7 C 0.7291(2) 0.4881(7) 0.18947(16) 0.0215(7) Uani 1 1 d . . . . .
H7A H 0.702698 0.556172 0.141215 0.032 Uiso 1 1 calc GR . . . .
H7B H 0.697354 0.295291 0.203997 0.032 Uiso 1 1 calc GR . . . .
H7C H 0.799581 0.454444 0.185637 0.032 Uiso 1 1 calc GR . . . .
C8 C 0.5088(2) 0.5248(7) 0.33488(17) 0.0205(6) Uani 1 1 d . . . . .
H8A H 0.455160 0.445493 0.303649 0.031 Uiso 1 1 calc GR . . . .
H8B H 0.522568 0.738841 0.321109 0.031 Uiso 1 1 calc GR . . . .
H8C H 0.490231 0.515973 0.387284 0.031 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C3 1.874(3) . ?
Br2 C6 1.874(3) . ?
S1 N1 1.620(3) . ?
S1 N2 1.622(3) . ?
O1 C4 1.362(3) . ?
O1 C7 1.442(3) . ?
O2 C5 1.369(3) . ?
O2 C8 1.442(3) . ?
N1 C2 1.337(4) . ?
N2 C1 1.343(4) . ?
C1 C2 1.427(4) . ?
C1 C6 1.422(4) . ?
C2 C3 1.422(4) . ?
C3 C4 1.372(4) . ?
C4 C5 1.439(4) . ?
C5 C6 1.362(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
N1 S1 N2 100.95(13) . . ?
C4 O1 C7 115.6(2) . . ?
C5 O2 C8 112.7(2) . . ?
C2 N1 S1 106.1(2) . . ?
C1 N2 S1 105.8(2) . . ?
N2 C1 C2 113.6(2) . . ?
N2 C1 C6 126.9(3) . . ?
C6 C1 C2 119.5(2) . . ?
N1 C2 C1 113.6(2) . . ?
N1 C2 C3 126.0(3) . . ?
C3 C2 C1 120.4(2) . . ?
C2 C3 Br1 119.1(2) . . ?
C4 C3 Br1 122.2(2) . . ?
C4 C3 C2 118.7(3) . . ?
O1 C4 C3 120.4(2) . . ?
O1 C4 C5 118.6(2) . . ?
C3 C4 C5 120.8(2) . . ?
O2 C5 C4 117.0(2) . . ?
C6 C5 O2 121.8(3) . . ?
C6 C5 C4 121.2(3) . . ?
C1 C6 Br2 119.5(2) . . ?
C5 C6 Br2 121.2(2) . . ?
C5 C6 C1 119.3(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.979
_oxdiff_exptl_absorpt_empirical_full_min 0.778
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_it2108b_t_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2234915'
loop_
_audit_author_name
_audit_author_address
'Tsutomu Ishi-i'
;National Institute of Technology, Kurume College
Japan
;
_audit_update_record             
;
2023-01-07 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_audit_creation_date             2022-01-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br2 C6 F2 N2 S'
_chemical_formula_sum            'C6 Br2 F2 N2 S'
_chemical_formula_weight         329.96
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.0701(2)
_cell_length_b                   12.7597(6)
_cell_length_c                   17.0263(9)
_cell_angle_alpha                72.084(4)
_cell_angle_beta                 89.411(4)
_cell_angle_gamma                89.426(4)
_cell_volume                     841.29(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5167
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.6990
_cell_measurement_theta_min      2.3090
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.220
_exptl_absorpt_coefficient_mu    9.863
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.605
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3887
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.749
_diffrn_reflns_theta_min         2.386
_diffrn_ambient_temperature      100
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00  64.00   0.25    8.00    --  -25.30  45.00 120.00  712
  2  ω   -114.00  64.00   0.25    8.00    --  -25.30  45.00 178.96  712
  3  ω   -114.00  64.00   0.25    8.00    --  -25.30  45.00  30.00  712
  4  ω   -114.00  64.00   0.25    8.00    --  -25.30  45.00  90.00  712
  5  ω   -114.00  64.00   0.25    8.00    --  -25.30  45.00 150.00  712
  6  ω   -114.00  64.00   0.25    8.00    --  -25.30  45.00 -12.46  712
  7  ω    -84.00  94.00   0.25    8.00    --    5.00  45.00  73.10  712
  8  ω   -114.00   4.00   0.25    8.00    --  -25.30  45.00 -19.94  472
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0197049000
_diffrn_orient_matrix_UB_12      0.0307127000
_diffrn_orient_matrix_UB_13      0.0279925000
_diffrn_orient_matrix_UB_21      -0.0404047000
_diffrn_orient_matrix_UB_22      0.0491249000
_diffrn_orient_matrix_UB_23      -0.0317700000
_diffrn_orient_matrix_UB_31      -0.1684221000
_diffrn_orient_matrix_UB_32      -0.0077720000
_diffrn_orient_matrix_UB_33      0.0112206000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3438
_reflns_number_total             3887
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.672
_refine_diff_density_min         -1.388
_refine_diff_density_rms         0.378
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.252
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3887
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.252
_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)+(0.0592P)²+14.8303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1655
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.91382
 0.08618
2. Restrained distances
 C12-C11 \\sim C10-C9 \\sim C8-C7
 with sigma of 0.01
 C2-C1 \\sim C6-C5 \\sim C4-C3
 with sigma of 0.01
 C6-C1 \\sim C2-C3 \\sim C4-C5
 with sigma of 0.01
 C10-C11 \\sim C12-C7 \\sim C8-C9
 with sigma of 0.01
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.7558(3) 0.07054(8) 0.26773(6) 0.0185(3) Uani 1 1 d . . . . .
Br2 Br 0.1462(3) 0.45070(9) 0.42016(7) 0.0224(3) Uani 1 1 d . . . . .
C1 C 0.498(2) 0.2485(7) 0.4297(6) 0.016(2) Uani 1 1 d D . . . .
C2 C 0.629(2) 0.1698(8) 0.3964(5) 0.015(2) Uani 1 1 d D . . . .
C3 C 0.583(2) 0.1764(8) 0.3125(5) 0.015(2) Uani 1 1 d D . . . .
C4 C 0.398(2) 0.2638(7) 0.2658(6) 0.015(2) Uani 1 1 d D . . . .
C5 C 0.263(2) 0.3428(8) 0.2998(5) 0.017(2) Uani 1 1 d D . . . .
C6 C 0.312(3) 0.3391(7) 0.3804(5) 0.019(2) Uani 1 1 d D . . . .
F1 F 0.3369(17) 0.2782(5) 0.1867(4) 0.0264(15) Uani 1 1 d . . . . .
F2 F 0.0839(15) 0.4235(5) 0.2489(4) 0.0207(13) Uani 1 1 d . . . . .
N1 N 0.573(2) 0.2287(7) 0.5104(5) 0.0185(19) Uani 1 1 d . . . . .
N2 N 0.799(2) 0.0890(7) 0.4499(5) 0.0173(18) Uani 1 1 d . . . . .
S1 S 0.7860(7) 0.1167(2) 0.53659(15) 0.0191(5) Uani 1 1 d . . . . .
Br3 Br 1.1919(3) 0.71905(9) -0.03489(6) 0.0229(3) Uani 1 1 d . . . . .
Br4 Br 0.6884(3) 0.74236(9) 0.32997(6) 0.0188(3) Uani 1 1 d . . . . .
C7 C 1.012(2) 0.8264(8) 0.1711(5) 0.014(2) Uani 1 1 d D . . . .
C8 C 1.122(3) 0.8196(8) 0.0945(5) 0.018(2) Uani 1 1 d D . . . .
C9 C 1.049(2) 0.7289(7) 0.0670(5) 0.017(2) Uani 1 1 d D . . . .
C10 C 0.861(2) 0.6466(8) 0.1197(5) 0.015(2) Uani 1 1 d D . . . .
C11 C 0.755(3) 0.6533(7) 0.1971(5) 0.017(2) Uani 1 1 d D . . . .
C12 C 0.829(2) 0.7406(7) 0.2257(5) 0.0127(19) Uani 1 1 d D . . . .
F3 F 0.7757(17) 0.5575(5) 0.1002(4) 0.0240(14) Uani 1 1 d . . . . .
F4 F 0.5705(16) 0.5702(5) 0.2429(4) 0.0213(13) Uani 1 1 d . . . . .
N3 N 1.106(2) 0.9202(7) 0.1863(5) 0.0192(19) Uani 1 1 d . . . . .
N4 N 1.295(2) 0.9080(7) 0.0500(5) 0.0155(17) Uani 1 1 d . . . . .
S2 S 1.3072(7) 0.9907(2) 0.10549(15) 0.0178(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C3 1.872(9) . ?
Br2 C6 1.872(9) . ?
C1 C2 1.396(9) . ?
C1 C6 1.418(10) . ?
C1 N1 1.354(13) . ?
C2 C3 1.420(9) . ?
C2 N2 1.339(13) . ?
C3 C4 1.375(10) . ?
C4 C5 1.411(10) . ?
C4 F1 1.328(10) . ?
C5 C6 1.376(10) . ?
C5 F2 1.339(11) . ?
N1 S1 1.608(9) . ?
N2 S1 1.621(9) . ?
Br3 C9 1.864(9) . ?
Br4 C12 1.866(9) . ?
C7 C8 1.401(9) . ?
C7 C12 1.413(10) . ?
C7 N3 1.360(13) . ?
C8 C9 1.411(10) . ?
C8 N4 1.348(13) . ?
C9 C10 1.384(10) . ?
C10 C11 1.411(10) . ?
C10 F3 1.328(11) . ?
C11 C12 1.383(9) . ?
C11 F4 1.338(11) . ?
N3 S2 1.613(9) . ?
N4 S2 1.621(9) . ?

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
C2 C1 C6 120.9(8) . . ?
N1 C1 C2 113.1(8) . . ?
N1 C1 C6 126.0(8) . . ?
C1 C2 C3 121.9(8) . . ?
N2 C2 C1 114.5(7) . . ?
N2 C2 C3 123.6(7) . . ?
C2 C3 Br1 122.0(6) . . ?
C4 C3 Br1 121.5(6) . . ?
C4 C3 C2 116.5(8) . . ?
C3 C4 C5 121.6(8) . . ?
F1 C4 C3 121.8(7) . . ?
F1 C4 C5 116.6(7) . . ?
C6 C5 C4 122.7(8) . . ?
F2 C5 C4 116.4(7) . . ?
F2 C5 C6 120.9(7) . . ?
C1 C6 Br2 122.9(6) . . ?
C5 C6 Br2 120.7(6) . . ?
C5 C6 C1 116.4(8) . . ?
C1 N1 S1 106.2(7) . . ?
C2 N2 S1 105.6(6) . . ?
N1 S1 N2 100.5(5) . . ?
C8 C7 C12 121.2(8) . . ?
N3 C7 C8 113.4(8) . . ?
N3 C7 C12 125.3(7) . . ?
C7 C8 C9 122.2(9) . . ?
N4 C8 C7 113.8(7) . . ?
N4 C8 C9 124.0(7) . . ?
C8 C9 Br3 122.6(6) . . ?
C10 C9 Br3 121.0(6) . . ?
C10 C9 C8 116.4(8) . . ?
C9 C10 C11 121.1(8) . . ?
F3 C10 C9 121.8(7) . . ?
F3 C10 C11 117.1(7) . . ?
C12 C11 C10 123.3(8) . . ?
F4 C11 C10 116.5(7) . . ?
F4 C11 C12 120.2(7) . . ?
C7 C12 Br4 123.4(6) . . ?
C11 C12 Br4 120.9(6) . . ?
C11 C12 C7 115.7(8) . . ?
C7 N3 S2 106.1(6) . . ?
C8 N4 S2 106.1(6) . . ?
N3 S2 N4 100.5(5) . . ?

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 C3 C4 C5 179.1(8) . . . . ?
Br1 C3 C4 F1 -0.9(14) . . . . ?
C1 C2 C3 Br1 -179.6(8) . . . . ?
C1 C2 C3 C4 -0.7(15) . . . . ?
C1 C2 N2 S1 -0.3(11) . . . . ?
C1 N1 S1 N2 0.7(8) . . . . ?
C2 C1 C6 Br2 -177.1(8) . . . . ?
C2 C1 C6 C5 1.5(16) . . . . ?
C2 C1 N1 S1 -0.9(11) . . . . ?
C2 C3 C4 C5 0.2(15) . . . . ?
C2 C3 C4 F1 -179.8(9) . . . . ?
C2 N2 S1 N1 -0.2(8) . . . . ?
C3 C2 N2 S1 179.8(9) . . . . ?
C3 C4 C5 C6 1.2(16) . . . . ?
C3 C4 C5 F2 -179.1(9) . . . . ?
C4 C5 C6 Br2 176.6(8) . . . . ?
C4 C5 C6 C1 -2.0(16) . . . . ?
C6 C1 C2 C3 -0.1(16) . . . . ?
C6 C1 C2 N2 -180.0(10) . . . . ?
C6 C1 N1 S1 180.0(10) . . . . ?
F1 C4 C5 C6 -178.7(10) . . . . ?
F1 C4 C5 F2 0.9(14) . . . . ?
F2 C5 C6 Br2 -3.0(15) . . . . ?
F2 C5 C6 C1 178.3(9) . . . . ?
N1 C1 C2 C3 -179.3(9) . . . . ?
N1 C1 C2 N2 0.9(14) . . . . ?
N1 C1 C6 Br2 1.9(16) . . . . ?
N1 C1 C6 C5 -179.5(10) . . . . ?
N2 C2 C3 Br1 0.2(15) . . . . ?
N2 C2 C3 C4 179.1(10) . . . . ?
Br3 C9 C10 C11 179.4(8) . . . . ?
Br3 C9 C10 F3 0.2(14) . . . . ?
C7 C8 C9 Br3 179.7(8) . . . . ?
C7 C8 C9 C10 0.1(15) . . . . ?
C7 C8 N4 S2 0.2(11) . . . . ?
C7 N3 S2 N4 -1.4(8) . . . . ?
C8 C7 C12 Br4 177.7(8) . . . . ?
C8 C7 C12 C11 -2.7(14) . . . . ?
C8 C7 N3 S2 1.7(11) . . . . ?
C8 C9 C10 C11 -1.0(15) . . . . ?
C8 C9 C10 F3 179.8(9) . . . . ?
C8 N4 S2 N3 0.7(8) . . . . ?
C9 C8 N4 S2 178.5(9) . . . . ?
C9 C10 C11 C12 0.0(16) . . . . ?
C9 C10 C11 F4 179.1(9) . . . . ?
C10 C11 C12 Br4 -178.5(8) . . . . ?
C10 C11 C12 C7 1.9(15) . . . . ?
C12 C7 C8 C9 1.9(16) . . . . ?
C12 C7 C8 N4 -179.8(9) . . . . ?
C12 C7 N3 S2 -179.9(8) . . . . ?
F3 C10 C11 C12 179.2(9) . . . . ?
F3 C10 C11 F4 -1.6(14) . . . . ?
F4 C11 C12 Br4 2.4(13) . . . . ?
F4 C11 C12 C7 -177.2(9) . . . . ?
N3 C7 C8 C9 -179.6(9) . . . . ?
N3 C7 C8 N4 -1.3(13) . . . . ?
N3 C7 C12 Br4 -0.6(15) . . . . ?
N3 C7 C12 C11 178.9(10) . . . . ?
N4 C8 C9 Br3 1.5(15) . . . . ?
N4 C8 C9 C10 -178.1(10) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.296
_oxdiff_exptl_absorpt_empirical_full_min 0.796
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.91382 53 18364 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.08618 56 18364 nmt 0.9969 0.0008 0.0039 0.0349 -1.0044 0.0046 0.0860
-0.0094 -0.9986

_twin_special_details            
;
Component 2 rotated by -179.6067° 
 around [1.00 0.02 0.04] (reciprocal) or [1.00 -0.00 0.00] (direct)
;
