# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_it2207a_auto
_database_code_depnum_ccdc_archive 'CCDC 2499601'
loop_
_audit_author_name
_audit_author_address
'Tsutomu Ishi-i'
;National Institute of Technology, Kurume College
Japan
;
_audit_update_record             
;
2025-11-01 deposited with the CCDC.	2026-02-15 downloaded from the CCDC.
;
_audit_creation_date             2022-09-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 Br2 N2 O2 S'
_chemical_formula_sum            'C14 H10 Br2 N2 O2 S'
_chemical_formula_weight         430.12
_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 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   12.0683(4)
_cell_length_b                   16.5725(5)
_cell_length_c                   7.4621(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.850(3)
_cell_angle_gamma                90
_cell_volume                     1435.69(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7656
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.9800
_cell_measurement_theta_min      3.7560
_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.131
_exptl_absorpt_coefficient_mu    8.578
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.41a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.990
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            10776
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.116
_diffrn_reflns_theta_min         3.807
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_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 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    100.00 125.00   0.50    0.05    --  107.00  15.00  30.00   50
  2  ω    100.00 165.00   0.50    0.05    --  107.00  30.00-120.00  130
  3  ω    100.00 135.00   0.50    0.05    --  107.00  15.00-150.00   70
  4  ω    103.00 128.00   0.50    0.05    --  107.00  15.00-180.00   50
  5  ω    -14.00  32.00   0.50    0.05    --  -44.34  38.00 -30.00   92
  6  ω      1.00  27.00   0.50    0.05    --  -44.34  38.00 -60.00   52
  7  ω    -70.00 -44.00   0.50    0.05    -- -104.00  77.00   0.00   52
  8  ω    -43.00   9.00   0.50    0.05    --  -44.34  57.00   0.00  104
  9  ω     21.00  83.00   0.50    0.05    --   44.34-128.00 151.00  124
 10  ω     64.00  94.00   0.50    0.05    --  107.00-128.00 151.00   60
 11  ω     42.00  68.00   0.50    0.05    --  107.00-125.00 -60.00   52
 12  ω     35.00  61.00   0.50    0.05    --  107.00-125.00 -90.00   52
 13  ω     54.00  94.00   0.50    0.05    --  107.00-125.00-150.00   80
 14  ω     67.00 100.00   0.50    0.05    --  107.00-125.00 -90.00   66
 15  ω     62.00  87.00   0.50    0.05    --  107.00 -95.00-150.00   50
 16  ω     44.00  93.00   0.50    0.05    --  107.00 -95.00-120.00   98
 17  ω     73.00  98.00   0.50    0.05    --  107.00-125.00 -60.00   50
 18  ω     34.00  59.00   0.50    0.05    --  107.00 -95.00 150.00   50
 19  ω     61.00  95.00   0.50    0.05    --  107.00 -90.00 126.90   68
 20  ω     40.00  74.00   0.50    0.05    --  107.00 -77.00 -30.00   68
 21  ω     37.00  75.00   0.50    0.05    --  107.00 -77.00 150.00   76
 22  ω     36.00  62.00   0.50    0.05    --  107.00 -77.00 -60.00   52
 23  ω     34.00  59.00   0.50    0.05    --  107.00 -77.00 -90.00   50
 24  ω     37.00  71.00   0.50    0.05    --  107.00 -77.00-180.00   68
 25  ω    -30.00   4.00   0.50    0.05    --   44.34 -38.00-180.00   68
 26  ω    -31.00  13.00   0.50    0.05    --   44.34 -38.00 150.00   88
 27  ω     95.00 171.00   0.50    0.05    --  107.00 125.00-120.00  152
 28  ω     94.00 136.00   0.50    0.05    --  107.00 128.00-134.00   84
 29  ω    -71.00 -18.00   0.50    0.05    --  -44.34 128.00-134.00  106
 30  ω    -90.00 -65.00   0.50    0.05    -- -104.00 128.00-134.00   50
 31  ω   -134.00-108.00   0.50    0.05    -- -104.00 -15.00  90.00   52
 32  ω   -130.00 -97.00   0.50    0.05    -- -104.00 -15.00 120.00   66
 33  ω   -122.00 -96.00   0.50    0.05    -- -104.00 -15.00 150.00   52
 34  ω   -128.00 -94.00   0.50    0.05    -- -104.00-128.00 151.00   68
 35  ω   -132.00-107.00   0.50    0.05    -- -104.00 -15.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0202352000
_diffrn_orient_matrix_UB_12      0.0917551000
_diffrn_orient_matrix_UB_13      -0.0019833000
_diffrn_orient_matrix_UB_21      -0.1310149000
_diffrn_orient_matrix_UB_22      0.0144596000
_diffrn_orient_matrix_UB_23      -0.0485058000
_diffrn_orient_matrix_UB_31      0.0070533000
_diffrn_orient_matrix_UB_32      0.0042094000
_diffrn_orient_matrix_UB_33      0.2089235000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2777
_reflns_number_total             2911
_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 1.171.42.41a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.41a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.41a (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  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.575
_refine_diff_density_min         -1.014
_refine_diff_density_rms         0.127
_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     192
_refine_ls_number_reflns         2911
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+0.8325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0844
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C12(H12), C13(H13)
1.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
;
_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 0.87472(2) 0.28951(2) 0.65080(4) 0.01710(11) Uani 1 1 d . . . . .
Br2 Br 0.42945(2) 0.69780(2) -0.17916(3) 0.01798(11) Uani 1 1 d . . . . .
S1 S 1.03323(5) 0.42041(4) 0.20885(8) 0.01651(15) Uani 1 1 d . . . . .
O1 O 0.66625(14) 0.41020(10) 0.6189(2) 0.0153(3) Uani 1 1 d . . . . .
O2 O 0.60954(14) 0.54124(10) 0.3989(2) 0.0151(3) Uani 1 1 d . . . . .
N2 N 0.93501(17) 0.48984(12) 0.1587(3) 0.0146(4) Uani 1 1 d . . . . .
N1 N 0.99535(17) 0.37179(12) 0.3709(3) 0.0163(4) Uani 1 1 d . . . . .
C1 C 0.9011(2) 0.40921(14) 0.3921(3) 0.0132(4) Uani 1 1 d . . . . .
C6 C 0.86604(19) 0.47733(14) 0.2698(3) 0.0116(4) Uani 1 1 d . . . . .
C2 C 0.8345(2) 0.38563(14) 0.5136(3) 0.0139(5) Uani 1 1 d . . . . .
C3 C 0.74000(19) 0.43032(14) 0.5178(3) 0.0129(4) Uani 1 1 d . . . . .
C9 C 0.7319(2) 0.59494(13) 0.1476(3) 0.0117(4) Uani 1 1 d . . . . .
C5 C 0.76583(19) 0.52370(13) 0.2721(3) 0.0110(4) Uani 1 1 d . . . . .
C10 C 0.6156(2) 0.60887(14) 0.0533(3) 0.0124(4) Uani 1 1 d . . . . .
H10 H 0.557480 0.572322 0.065542 0.015 Uiso 1 1 calc R U . . .
C11 C 0.5874(2) 0.67717(14) -0.0582(3) 0.0132(4) Uani 1 1 d . . . . .
C14 C 0.8152(2) 0.64962(14) 0.1258(3) 0.0139(4) Uani 1 1 d . . . . .
H14 H 0.893805 0.640838 0.189893 0.017 Uiso 1 1 calc R U . . .
C12 C 0.6698(2) 0.73135(14) -0.0822(3) 0.0161(5) Uani 1 1 d . . . . .
H12 H 0.648406 0.777200 -0.160397 0.019 Uiso 1 1 calc R U . . .
C4 C 0.70682(19) 0.49997(14) 0.3959(3) 0.0122(4) Uani 1 1 d . . . . .
C8 C 0.6090(2) 0.57909(15) 0.5736(3) 0.0168(5) Uani 1 1 d . . . . .
H8A H 0.561691 0.628021 0.548744 0.025 Uiso 1 1 calc R U . . .
H8B H 0.688004 0.593328 0.642460 0.025 Uiso 1 1 calc R U . . .
H8C H 0.577047 0.541544 0.647924 0.025 Uiso 1 1 calc R U . . .
C13 C 0.7845(2) 0.71677(14) 0.0113(3) 0.0166(5) Uani 1 1 d . . . . .
H13 H 0.842372 0.753038 -0.003202 0.020 Uiso 1 1 calc R U . . .
C7 C 0.7098(2) 0.41080(17) 0.8187(3) 0.0223(5) Uani 1 1 d . . . . .
H7A H 0.780585 0.442988 0.854789 0.033 Uiso 1 1 calc R U . . .
H7B H 0.726537 0.355408 0.863939 0.033 Uiso 1 1 calc R U . . .
H7C H 0.652082 0.434421 0.873276 0.033 Uiso 1 1 calc R U . . .


_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 C2 1.884(2) . ?
Br2 C11 1.904(2) . ?
S1 N2 1.621(2) . ?
S1 N1 1.620(2) . ?
O1 C3 1.356(3) . ?
O1 C7 1.439(3) . ?
O2 C4 1.364(3) . ?
O2 C8 1.448(3) . ?
N2 C6 1.342(3) . ?
N1 C1 1.342(3) . ?
C1 C6 1.440(3) . ?
C1 C2 1.421(3) . ?
C6 C5 1.437(3) . ?
C2 C3 1.368(3) . ?
C3 C4 1.456(3) . ?
C9 C5 1.489(3) . ?
C9 C10 1.406(3) . ?
C9 C14 1.396(3) . ?
C5 C4 1.369(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(3) . ?
C11 C12 1.387(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C13 H13 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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 100.82(11) . . ?
C3 O1 C7 117.70(19) . . ?
C4 O2 C8 116.57(18) . . ?
C6 N2 S1 106.60(16) . . ?
C1 N1 S1 106.19(16) . . ?
N1 C1 C6 113.6(2) . . ?
N1 C1 C2 126.4(2) . . ?
C2 C1 C6 120.0(2) . . ?
N2 C6 C1 112.8(2) . . ?
N2 C6 C5 126.2(2) . . ?
C5 C6 C1 121.0(2) . . ?
C1 C2 Br1 118.21(17) . . ?
C3 C2 Br1 122.55(18) . . ?
C3 C2 C1 119.1(2) . . ?
O1 C3 C2 123.9(2) . . ?
O1 C3 C4 115.6(2) . . ?
C2 C3 C4 120.3(2) . . ?
C10 C9 C5 120.6(2) . . ?
C14 C9 C5 120.2(2) . . ?
C14 C9 C10 119.2(2) . . ?
C6 C5 C9 120.4(2) . . ?
C4 C5 C6 116.7(2) . . ?
C4 C5 C9 122.9(2) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.7(2) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 Br2 118.66(18) . . ?
C12 C11 Br2 118.86(17) . . ?
C12 C11 C10 122.5(2) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C11 C12 H12 120.9 . . ?
C11 C12 C13 118.2(2) . . ?
C13 C12 H12 120.9 . . ?
O2 C4 C3 118.6(2) . . ?
O2 C4 C5 118.4(2) . . ?
C5 C4 C3 123.0(2) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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 C2 C3 O1 -0.3(3) . . . . ?
Br1 C2 C3 C4 -174.26(16) . . . . ?
Br2 C11 C12 C13 178.16(17) . . . . ?
S1 N2 C6 C1 0.2(2) . . . . ?
S1 N2 C6 C5 -178.96(19) . . . . ?
S1 N1 C1 C6 -0.1(2) . . . . ?
S1 N1 C1 C2 177.09(19) . . . . ?
O1 C3 C4 O2 3.1(3) . . . . ?
O1 C3 C4 C5 -173.8(2) . . . . ?
N2 S1 N1 C1 0.18(18) . . . . ?
N2 C6 C5 C9 -2.1(3) . . . . ?
N2 C6 C5 C4 179.4(2) . . . . ?
N1 S1 N2 C6 -0.20(18) . . . . ?
N1 C1 C6 N2 0.0(3) . . . . ?
N1 C1 C6 C5 179.1(2) . . . . ?
N1 C1 C2 Br1 -3.7(3) . . . . ?
N1 C1 C2 C3 -179.6(2) . . . . ?
C1 C6 C5 C9 178.79(19) . . . . ?
C1 C6 C5 C4 0.3(3) . . . . ?
C1 C2 C3 O1 175.4(2) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C6 C1 C2 Br1 173.28(16) . . . . ?
C6 C1 C2 C3 -2.6(3) . . . . ?
C6 C5 C4 O2 -178.38(19) . . . . ?
C6 C5 C4 C3 -1.5(3) . . . . ?
C2 C1 C6 N2 -177.4(2) . . . . ?
C2 C1 C6 C5 1.8(3) . . . . ?
C2 C3 C4 O2 177.5(2) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C9 C5 C4 O2 3.2(3) . . . . ?
C9 C5 C4 C3 -180.0(2) . . . . ?
C9 C10 C11 Br2 -177.95(16) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C9 C14 C13 C12 0.8(4) . . . . ?
C5 C9 C10 C11 178.5(2) . . . . ?
C5 C9 C14 C13 -179.4(2) . . . . ?
C10 C9 C5 C6 138.1(2) . . . . ?
C10 C9 C5 C4 -43.5(3) . . . . ?
C10 C9 C14 C13 -0.5(3) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C14 C9 C5 C6 -43.1(3) . . . . ?
C14 C9 C5 C4 135.3(2) . . . . ?
C14 C9 C10 C11 -0.3(3) . . . . ?
C8 O2 C4 C3 62.3(3) . . . . ?
C8 O2 C4 C5 -120.7(2) . . . . ?
C7 O1 C3 C2 65.6(3) . . . . ?
C7 O1 C3 C4 -120.1(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 3.195
_oxdiff_exptl_absorpt_empirical_full_min 0.417
####################################################################### 
# 
# 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_it2208b_auto
_database_code_depnum_ccdc_archive 'CCDC 2499602'
loop_
_audit_author_name
_audit_author_address
'Tsutomu Ishi-i'
;National Institute of Technology, Kurume College
Japan
;
_audit_update_record             
;
2025-11-01 deposited with the CCDC.	2026-02-15 downloaded from the CCDC.
;
_audit_creation_date             2022-09-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 Br2 N2 O2 S'
_chemical_formula_sum            'C14 H10 Br2 N2 O2 S'
_chemical_formula_weight         430.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N S Br'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   13.1781(3)
_cell_length_b                   7.36850(10)
_cell_length_c                   16.2703(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.869(2)
_cell_angle_gamma                90
_cell_volume                     1526.99(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9380
_cell_measurement_temperature    100.04(10)
_cell_measurement_theta_max      75.4610
_cell_measurement_theta_min      3.4290
_shelx_estimated_absorpt_T_max   0.551
_shelx_estimated_absorpt_T_min   0.430
_exptl_absorpt_coefficient_mu    8.065
_exptl_absorpt_correction_T_max  0.369
_exptl_absorpt_correction_T_min  0.087
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.41a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.871
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 1 3 0.0648
-1 5 -2 0.0713
-7 -1 -3 0.0529
1 -5 1 0.0476
4 4 1 0.0711
-5 0 10 0.0374
-4 -4 0 0.0638
5 0 -10 0.0467

_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.084
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7.0158 0.8419 3.3319 0.4203 -0.6127 0.6693
-1.2737 4.6306 -1.6663 -0.4058 0.5869 0.7007
-6.8787 -1.3568 -3.1488 -0.3755 0.5478 -0.7476
0.8862 -4.6860 1.4842 0.3832 -0.5539 -0.7392
4.2939 4.0204 0.6964 0.0370 0.0230 0.9990
-4.8470 0.3842 9.9049 -0.8236 -0.5671 -0.0090
-4.4551 -3.9968 -0.3433 -0.0662 -0.0430 -0.9969
4.8470 -0.3842 -9.9049 0.8236 0.5671 0.0090

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12422
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.565
_diffrn_reflns_theta_min         3.470
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.04(10)
_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 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     93.00 118.00   0.50    0.05    --  107.00  61.00  60.00   50
  2  ω    107.00 133.00   0.50    0.05    --  107.00  77.00  90.00   52
  3  ω    139.00 171.00   0.50    0.05    --  107.00  77.00  90.00   64
  4  ω    140.00 178.00   0.50    0.05    --  107.00  61.00  60.00   76
  5  ω    128.00 171.00   0.50    0.05    --  107.00  43.00  29.00   86
  6  ω    103.00 128.00   0.50    0.05    --  107.00  15.00 -30.00   50
  7  ω    109.00 134.00   0.50    0.05    --  107.00  15.00 -60.00   50
  8  ω     93.00 120.00   0.50    0.05    --  107.00  61.00 -60.00   54
  9  ω    139.00 165.00   0.50    0.05    --  107.00  61.00 -60.00   52
 10  ω    100.00 138.00   0.50    0.05    --  107.00  15.00  90.00   76
 11  ω     99.00 136.00   0.50    0.05    --  107.00  15.00 150.00   74
 12  ω     42.00 113.00   0.50    0.05    --   44.34  43.00  29.00  142
 13  ω      2.00  31.00   0.50    0.05    --  -44.34  38.00 150.00   58
 14  ω    -62.00 -36.00   0.50    0.05    -- -104.00  77.00   0.00   52
 15  ω    -22.00   4.00   0.50    0.05    --  -44.34  43.00  29.00   52
 16  ω    -13.00  29.00   0.50    0.05    --  -44.34  38.00 -30.00   84
 17  ω     42.00  72.00   0.50    0.05    --  107.00-125.00-150.00   60
 18  ω     48.00  94.00   0.50    0.05    --  107.00-125.00-180.00   92
 19  ω    -29.00  25.00   0.50    0.05    --   44.34 -43.00-122.00  108
 20  ω     47.00  77.00   0.50    0.05    --  107.00 -77.00-150.00   60
 21  ω     36.00  74.00   0.50    0.05    --  107.00 -77.00  30.00   76
 22  ω     43.00  71.00   0.50    0.05    --  107.00 -77.00  90.00   56
 23  ω     34.00  75.00   0.50    0.05    --  107.00 -77.00 120.00   82
 24  ω    -28.00  19.00   0.50    0.05    --   44.34 -38.00 120.00   94
 25  ω    -29.00  12.00   0.50    0.05    --   44.34 -38.00  90.00   82
 26  ω     39.00  70.00   0.50    0.05    --  107.00 -77.00 -30.00   62
 27  ω     38.00  65.00   0.50    0.05    --  107.00 -77.00 -90.00   54
 28  ω     35.00  68.00   0.50    0.05    --  107.00 -77.00-180.00   66
 29  ω     41.00  75.00   0.50    0.05    --  107.00 -77.00   0.00   68
 30  ω     43.00  68.00   0.50    0.05    --  107.00 -77.00  60.00   50
 31  ω     97.00 122.00   0.50    0.05    --  107.00 125.00 -90.00   50
 32  ω     96.00 125.00   0.50    0.05    --  107.00 125.00-150.00   58
 33  ω    144.00 170.00   0.50    0.05    --  107.00 125.00-150.00   52
 34  ω    135.00 176.00   0.50    0.05    --  107.00 125.00 -90.00   82
 35  ω   -119.00 -78.00   0.50    0.05    --  -44.34 -43.00-122.00   82
 36  ω    -73.00 -41.00   0.50    0.05    --  -44.34 -43.00-122.00   64
 37  ω   -175.00-101.00   0.50    0.05    -- -104.00 -43.00-122.00  148
 38  ω   -129.00-103.00   0.50    0.05    -- -104.00 -15.00 -60.00   52
 39  ω   -124.00 -98.00   0.50    0.05    -- -104.00 -15.00 -30.00   52
 40  ω   -128.00-103.00   0.50    0.05    -- -104.00 -15.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0870165000
_diffrn_orient_matrix_UB_12      -0.0772153000
_diffrn_orient_matrix_UB_13      -0.0375732000
_diffrn_orient_matrix_UB_21      -0.0553904000
_diffrn_orient_matrix_UB_22      0.0800242000
_diffrn_orient_matrix_UB_23      -0.0874656000
_diffrn_orient_matrix_UB_31      0.0631724000
_diffrn_orient_matrix_UB_32      0.1770176000
_diffrn_orient_matrix_UB_33      0.0231359000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3003
_reflns_number_total             3144
_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 1.171.42.41a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.41a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.41a (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  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+0.9127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0792
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
1.b 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 0.58557(2) 0.22704(3) 0.30893(2) 0.02609(10) Uani 1 1 d . . . . .
Br2 Br 0.89858(2) 0.91397(3) 0.91643(2) 0.02905(10) Uani 1 1 d . . . . .
S4 S 0.51596(4) 0.79505(8) 0.43056(4) 0.02602(14) Uani 1 1 d . . . . .
O1 O 0.83196(13) 0.2500(2) 0.61728(10) 0.0247(3) Uani 1 1 d . . . . .
O2 O 0.75257(13) 0.0894(2) 0.46408(11) 0.0279(4) Uani 1 1 d . . . . .
N1 N 0.52623(15) 0.6089(3) 0.37995(12) 0.0243(4) Uani 1 1 d . . . . .
N2 N 0.60221(16) 0.7610(3) 0.51948(13) 0.0243(4) Uani 1 1 d . . . . .
C1 C 0.60078(17) 0.5102(3) 0.43291(14) 0.0222(4) Uani 1 1 d . . . . .
C2 C 0.64456(17) 0.5967(3) 0.51344(14) 0.0229(4) Uani 1 1 d . . . . .
C3 C 0.72484(17) 0.5117(3) 0.57803(14) 0.0220(4) Uani 1 1 d . . . . .
C4 C 0.75725(16) 0.3438(3) 0.55832(14) 0.0221(4) Uani 1 1 d . . . . .
C5 C 0.71635(18) 0.2577(3) 0.47674(15) 0.0229(4) Uani 1 1 d . . . . .
C6 C 0.63903(17) 0.3377(3) 0.41547(14) 0.0232(4) Uani 1 1 d . . . . .
C7 C 0.7865(2) 0.1154(4) 0.66166(17) 0.0344(5) Uani 1 1 d . . . . .
H7A H 0.737869 0.038854 0.620252 0.052 Uiso 1 1 calc R U . . .
H7B H 0.748293 0.176086 0.698217 0.052 Uiso 1 1 calc R U . . .
H7C H 0.842346 0.039868 0.696603 0.052 Uiso 1 1 calc R U . . .
C8 C 0.8578(2) 0.0882(4) 0.4537(2) 0.0394(6) Uani 1 1 d . . . . .
H8A H 0.856699 0.127418 0.395967 0.059 Uiso 1 1 calc R U . . .
H8B H 0.886568 -0.034903 0.463198 0.059 Uiso 1 1 calc R U . . .
H8C H 0.901667 0.171216 0.494990 0.059 Uiso 1 1 calc R U . . .
C9 C 0.76810(18) 0.6008(3) 0.66157(14) 0.0224(4) Uani 1 1 d . . . . .
C10 C 0.70036(18) 0.6693(3) 0.70682(14) 0.0259(4) Uani 1 1 d . . . . .
H10 H 0.626766 0.654393 0.684861 0.031 Uiso 1 1 calc R U . . .
C11 C 0.73856(19) 0.7594(3) 0.78387(16) 0.0267(5) Uani 1 1 d . . . . .
H11 H 0.692067 0.805016 0.814933 0.032 Uiso 1 1 calc R U . . .
C12 C 0.84615(19) 0.7807(3) 0.81391(14) 0.0239(4) Uani 1 1 d . . . . .
C13 C 0.91604(18) 0.7122(3) 0.77102(15) 0.0255(5) Uani 1 1 d . . . . .
H13 H 0.989595 0.726576 0.793499 0.031 Uiso 1 1 calc R U . . .
C14 C 0.87653(17) 0.6223(3) 0.69463(14) 0.0246(4) Uani 1 1 d . . . . .
H14 H 0.923461 0.574739 0.664425 0.029 Uiso 1 1 calc R U . . .


_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 C6 1.881(2) . ?
Br2 C12 1.906(2) . ?
S4 N1 1.623(2) . ?
S4 N2 1.614(2) . ?
O1 C4 1.372(3) . ?
O1 C7 1.445(3) . ?
O2 C5 1.364(3) . ?
O2 C8 1.439(3) . ?
N1 C1 1.343(3) . ?
N2 C2 1.347(3) . ?
C1 C2 1.438(3) . ?
C1 C6 1.422(3) . ?
C2 C3 1.430(3) . ?
C3 C4 1.374(3) . ?
C3 C9 1.485(3) . ?
C4 C5 1.445(3) . ?
C5 C6 1.363(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.390(3) . ?
C9 C14 1.401(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.394(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(3) . ?
C12 C13 1.386(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(3) . ?
C14 H14 0.9500 . ?

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 S4 N1 101.08(10) . . ?
C4 O1 C7 112.33(18) . . ?
C5 O2 C8 114.11(18) . . ?
C1 N1 S4 105.96(16) . . ?
C2 N2 S4 106.49(16) . . ?
N1 C1 C2 113.6(2) . . ?
N1 C1 C6 126.5(2) . . ?
C6 C1 C2 119.9(2) . . ?
N2 C2 C1 112.8(2) . . ?
N2 C2 C3 125.6(2) . . ?
C3 C2 C1 121.6(2) . . ?
C2 C3 C9 121.1(2) . . ?
C4 C3 C2 116.0(2) . . ?
C4 C3 C9 122.8(2) . . ?
O1 C4 C3 120.05(19) . . ?
O1 C4 C5 116.9(2) . . ?
C3 C4 C5 123.0(2) . . ?
O2 C5 C4 118.4(2) . . ?
C6 C5 O2 120.5(2) . . ?
C6 C5 C4 121.0(2) . . ?
C1 C6 Br1 120.20(16) . . ?
C5 C6 Br1 121.29(18) . . ?
C5 C6 C1 118.5(2) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C3 119.8(2) . . ?
C10 C9 C14 119.1(2) . . ?
C14 C9 C3 121.0(2) . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.9 . . ?
C12 C11 C10 118.2(2) . . ?
C12 C11 H11 120.9 . . ?
C11 C12 Br2 118.40(18) . . ?
C11 C12 C13 122.2(2) . . ?
C13 C12 Br2 119.34(17) . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.7(2) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.6(2) . . ?
C13 C14 H14 119.7 . . ?

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
Br2 C12 C13 C14 -177.28(18) . . . . ?
S4 N1 C1 C2 0.4(2) . . . . ?
S4 N1 C1 C6 -178.25(19) . . . . ?
S4 N2 C2 C1 0.2(2) . . . . ?
S4 N2 C2 C3 179.89(19) . . . . ?
O1 C4 C5 O2 1.2(3) . . . . ?
O1 C4 C5 C6 177.4(2) . . . . ?
O2 C5 C6 Br1 -4.0(3) . . . . ?
O2 C5 C6 C1 177.47(19) . . . . ?
N1 S4 N2 C2 0.03(17) . . . . ?
N1 C1 C2 N2 -0.4(3) . . . . ?
N1 C1 C2 C3 179.9(2) . . . . ?
N1 C1 C6 Br1 0.7(3) . . . . ?
N1 C1 C6 C5 179.2(2) . . . . ?
N2 S4 N1 C1 -0.25(17) . . . . ?
N2 C2 C3 C4 -179.6(2) . . . . ?
N2 C2 C3 C9 1.5(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C2 C3 C9 -178.9(2) . . . . ?
C2 C1 C6 Br1 -177.89(16) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C3 C4 O1 -178.26(19) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
C2 C3 C9 C10 49.6(3) . . . . ?
C2 C3 C9 C14 -128.4(2) . . . . ?
C3 C4 C5 O2 -179.0(2) . . . . ?
C3 C4 C5 C6 -2.7(3) . . . . ?
C3 C9 C10 C11 -177.6(2) . . . . ?
C3 C9 C14 C13 177.3(2) . . . . ?
C4 C3 C9 C10 -129.3(2) . . . . ?
C4 C3 C9 C14 52.7(3) . . . . ?
C4 C5 C6 Br1 179.80(16) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C6 C1 C2 N2 178.34(19) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C7 O1 C4 C3 98.5(2) . . . . ?
C7 O1 C4 C5 -81.7(3) . . . . ?
C8 O2 C5 C4 -73.5(3) . . . . ?
C8 O2 C5 C6 110.2(3) . . . . ?
C9 C3 C4 O1 0.7(3) . . . . ?
C9 C3 C4 C5 -179.2(2) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C10 C9 C14 C13 -0.7(3) . . . . ?
C10 C11 C12 Br2 177.04(18) . . . . ?
C10 C11 C12 C13 -1.5(4) . . . . ?
C11 C12 C13 C14 1.2(4) . . . . ?
C12 C13 C14 C9 -0.1(3) . . . . ?
C14 C9 C10 C11 0.4(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 1.869
_oxdiff_exptl_absorpt_empirical_full_min 0.550
####################################################################### 
# 
# 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_it2201a
_database_code_depnum_ccdc_archive 'CCDC 2499603'
loop_
_audit_author_name
_audit_author_address
'Tsutomu Ishi-i'
;National Institute of Technology, Kurume College
Japan
;
_audit_update_record             
;
2025-11-01 deposited with the CCDC.	2026-02-15 downloaded from the CCDC.
;
_audit_creation_date             2022-01-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 Br2 N2 O2 S'
_chemical_formula_sum            'C14 H10 Br2 N2 O2 S'
_chemical_formula_weight         430.12
_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                   9.2163(4)
_cell_length_b                   20.2448(8)
_cell_length_c                   8.2360(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.566(5)
_cell_angle_gamma                90
_cell_volume                     1480.33(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7286
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.6470
_cell_measurement_theta_min      2.2500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.621
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.619
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.930
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
12 0 1 0.1322
-3 2 12 0.1442
-12 0 -1 0.1516
4 -2 -12 0.1800
12 -5 0 0.1248
0 -28 1 0.0600
0 28 -1 0.0360

_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.098
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
12.2051 -0.2090 0.9302 -0.0020 -0.0567 0.9984
-3.0886 1.5645 11.5907 -0.0349 -0.9980 0.0520
-12.2795 0.2363 -0.7316 0.0014 0.0395 -0.9992
3.6368 -1.5796 -11.5941 0.0349 0.9994 -0.0083
12.1952 -5.0880 0.3743 0.1682 -0.0059 0.9857
-0.0734 -28.4787 0.6313 0.9991 -0.0349 0.0250
-0.1338 28.4679 -0.6355 -0.9985 0.0349 -0.0416

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13391
_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         27.484
_diffrn_reflns_theta_min         2.294
_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 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  -7.00   0.50    0.50    --    5.00  45.00  60.00   52
  2  ω    -28.00  39.00   0.50    0.50    --  -10.20  45.00  90.00  134
  3  ω    -87.00 -51.00   0.50    0.50    --  -10.20  45.00  90.00   72
  4  ω    -99.00  75.00   0.50    0.50    --  -10.20  45.00 150.00  348
;
_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      -0.0008758000
_diffrn_orient_matrix_UB_12      -0.0350463000
_diffrn_orient_matrix_UB_13      0.0014901000
_diffrn_orient_matrix_UB_21      0.0018616000
_diffrn_orient_matrix_UB_22      -0.0006754000
_diffrn_orient_matrix_UB_23      -0.0855194000
_diffrn_orient_matrix_UB_31      0.0798238000
_diffrn_orient_matrix_UB_32      -0.0005107000
_diffrn_orient_matrix_UB_33      0.0258275000
_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                3081
_reflns_number_total             3394
_reflns_odcompleteness_completeness 99.91
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.068
_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)+(0.0253P)²+1.4832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0600
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
2.b 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 0.30305(3) 0.32011(2) 0.79114(3) 0.01889(7) Uani 1 1 d . . . . .
Br2 Br 1.06914(3) 0.71563(2) 0.65737(4) 0.02829(8) Uani 1 1 d . . . . .
C1 C 0.3966(2) 0.45517(11) 0.7899(3) 0.0140(4) Uani 1 1 d . . . . .
C2 C 0.4935(2) 0.50711(11) 0.7628(3) 0.0134(4) Uani 1 1 d . . . . .
C3 C 0.6347(2) 0.49348(11) 0.7269(3) 0.0140(4) Uani 1 1 d . . . . .
C4 C 0.6680(2) 0.42769(11) 0.7172(3) 0.0146(4) Uani 1 1 d . . . . .
C5 C 0.5691(2) 0.37493(11) 0.7367(3) 0.0149(4) Uani 1 1 d . . . . .
C6 C 0.4357(2) 0.38819(11) 0.7723(3) 0.0150(4) Uani 1 1 d . . . . .
C7 C 0.9177(3) 0.39912(13) 0.8444(3) 0.0224(5) Uani 1 1 d . . . . .
H7A H 1.011521 0.385754 0.819170 0.034 Uiso 1 1 calc R U . . .
H7B H 0.886391 0.364690 0.911520 0.034 Uiso 1 1 calc R U . . .
H7C H 0.933949 0.440597 0.908082 0.034 Uiso 1 1 calc R U . . .
C8 C 0.5938(3) 0.28971(13) 0.5545(3) 0.0284(6) Uani 1 1 d . . . . .
H8A H 0.489804 0.298143 0.489380 0.043 Uiso 1 1 calc R U . . .
H8B H 0.615007 0.242300 0.553389 0.043 Uiso 1 1 calc R U . . .
H8C H 0.663018 0.313980 0.504305 0.043 Uiso 1 1 calc R U . . .
C9 C 0.7378(2) 0.54717(11) 0.7080(3) 0.0147(4) Uani 1 1 d . . . . .
C10 C 0.7534(2) 0.60369(12) 0.8078(3) 0.0160(4) Uani 1 1 d . . . . .
H10 H 0.696267 0.607791 0.887664 0.019 Uiso 1 1 calc R U . . .
C11 C 0.8508(3) 0.65400(11) 0.7926(3) 0.0178(5) Uani 1 1 d . . . . .
H11 H 0.861045 0.692230 0.861615 0.021 Uiso 1 1 calc R U . . .
C12 C 0.9327(3) 0.64780(12) 0.6757(3) 0.0182(5) Uani 1 1 d . . . . .
C13 C 0.9192(3) 0.59263(12) 0.5731(3) 0.0177(5) Uani 1 1 d . . . . .
H13 H 0.975294 0.589250 0.492056 0.021 Uiso 1 1 calc R U . . .
C14 C 0.8223(3) 0.54253(12) 0.5909(3) 0.0160(5) Uani 1 1 d . . . . .
H14 H 0.813139 0.504268 0.522129 0.019 Uiso 1 1 calc R U . . .
N1 N 0.2711(2) 0.47661(10) 0.8258(2) 0.0163(4) Uani 1 1 d . . . . .
N2 N 0.4372(2) 0.56763(10) 0.7758(2) 0.0166(4) Uani 1 1 d . . . . .
O1 O 0.80220(17) 0.40840(8) 0.68953(19) 0.0168(3) Uani 1 1 d . . . . .
O2 O 0.61405(18) 0.31138(8) 0.7262(2) 0.0184(3) Uani 1 1 d . . . . .
S1 S 0.27907(6) 0.55641(3) 0.82104(7) 0.01737(13) 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 C6 1.876(2) . ?
Br2 C12 1.895(2) . ?
C1 C2 1.435(3) . ?
C1 C6 1.420(3) . ?
C1 N1 1.341(3) . ?
C2 C3 1.436(3) . ?
C2 N2 1.346(3) . ?
C3 C4 1.374(3) . ?
C3 C9 1.479(3) . ?
C4 C5 1.441(3) . ?
C4 O1 1.373(3) . ?
C5 C6 1.365(3) . ?
C5 O2 1.361(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 O1 1.438(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 O2 1.444(3) . ?
C9 C10 1.394(3) . ?
C9 C14 1.396(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(3) . ?
C12 C13 1.386(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9500 . ?
N1 S1 1.618(2) . ?
N2 S1 1.614(2) . ?

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
C6 C1 C2 119.9(2) . . ?
N1 C1 C2 114.0(2) . . ?
N1 C1 C6 126.1(2) . . ?
C1 C2 C3 121.8(2) . . ?
N2 C2 C1 112.7(2) . . ?
N2 C2 C3 125.5(2) . . ?
C2 C3 C9 121.6(2) . . ?
C4 C3 C2 115.3(2) . . ?
C4 C3 C9 123.1(2) . . ?
C3 C4 C5 123.6(2) . . ?
O1 C4 C3 120.7(2) . . ?
O1 C4 C5 115.64(19) . . ?
C6 C5 C4 120.8(2) . . ?
O2 C5 C4 118.74(19) . . ?
O2 C5 C6 120.4(2) . . ?
C1 C6 Br1 120.28(16) . . ?
C5 C6 Br1 121.18(18) . . ?
C5 C6 C1 118.5(2) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
C10 C9 C3 120.6(2) . . ?
C10 C9 C14 118.3(2) . . ?
C14 C9 C3 121.1(2) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.1(2) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 Br2 119.26(18) . . ?
C11 C12 C13 121.5(2) . . ?
C13 C12 Br2 119.23(18) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.7(2) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.3(2) . . ?
C13 C14 H14 119.4 . . ?
C1 N1 S1 105.69(16) . . ?
C2 N2 S1 106.35(16) . . ?
C4 O1 C7 112.04(17) . . ?
C5 O2 C8 112.84(18) . . ?
N2 S1 N1 101.29(10) . . ?

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
Br2 C12 C13 C14 178.19(17) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C1 C2 C3 C9 -176.72(19) . . . . ?
C1 C2 N2 S1 0.9(2) . . . . ?
C1 N1 S1 N2 -0.30(17) . . . . ?
C2 C1 C6 Br1 -175.35(15) . . . . ?
C2 C1 C6 C5 2.8(3) . . . . ?
C2 C1 N1 S1 0.9(2) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C2 C3 C4 O1 -177.66(18) . . . . ?
C2 C3 C9 C10 36.5(3) . . . . ?
C2 C3 C9 C14 -143.8(2) . . . . ?
C2 N2 S1 N1 -0.37(17) . . . . ?
C3 C2 N2 S1 -178.81(18) . . . . ?
C3 C4 C5 C6 -2.2(3) . . . . ?
C3 C4 C5 O2 -179.5(2) . . . . ?
C3 C4 O1 C7 90.5(2) . . . . ?
C3 C9 C10 C11 179.3(2) . . . . ?
C3 C9 C14 C13 -179.9(2) . . . . ?
C4 C3 C9 C10 -141.3(2) . . . . ?
C4 C3 C9 C14 38.4(3) . . . . ?
C4 C5 C6 Br1 178.02(16) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 O2 C8 -79.2(3) . . . . ?
C5 C4 O1 C7 -88.8(2) . . . . ?
C6 C1 C2 C3 -3.4(3) . . . . ?
C6 C1 C2 N2 176.84(19) . . . . ?
C6 C1 N1 S1 -177.05(18) . . . . ?
C6 C5 O2 C8 103.6(2) . . . . ?
C9 C3 C4 C5 179.5(2) . . . . ?
C9 C3 C4 O1 0.2(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C9 C14 C13 -0.2(3) . . . . ?
C10 C11 C12 Br2 -178.74(17) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C9 0.8(3) . . . . ?
C14 C9 C10 C11 -0.4(3) . . . . ?
N1 C1 C2 C3 178.51(19) . . . . ?
N1 C1 C2 N2 -1.2(3) . . . . ?
N1 C1 C6 Br1 2.5(3) . . . . ?
N1 C1 C6 C5 -179.4(2) . . . . ?
N2 C2 C3 C4 -179.1(2) . . . . ?
N2 C2 C3 C9 3.0(3) . . . . ?
O1 C4 C5 C6 177.04(19) . . . . ?
O1 C4 C5 O2 -0.2(3) . . . . ?
O2 C5 C6 Br1 -4.8(3) . . . . ?
O2 C5 C6 C1 177.10(19) . . . . ?

_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 2.163
_oxdiff_exptl_absorpt_empirical_full_min 0.685
