# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_s2nbr
_database_code_depnum_ccdc_archive 'CCDC 1955658'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi' 'Aix Marseille Universite'
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_audit_creation_date             2017-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 Br N S2'
_chemical_formula_sum            'C10 H8 Br N S2'
_chemical_formula_weight         286.20
_chemical_melting_point          ?

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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0030(2)
_cell_length_b                   11.3382(3)
_cell_length_c                   12.9419(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.882(2)
_cell_angle_gamma                90
_cell_volume                     1123.73(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5054
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.7030
_cell_measurement_theta_min      5.2640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
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    1.692
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9043
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.875
_diffrn_reflns_theta_min         5.289
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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 -63.00   1.00    1.00    --  -17.77 -77.00 -60.00   30
  2  ω    -80.00 -23.00   1.00    1.00    --  -17.77 -38.00  60.00   57
  3  ω   -104.00 -68.00   1.00    1.00    --  -17.77 178.00  30.00   36
  4  ω    -92.00 -63.00   1.00    1.00    --  -17.77 -38.00  90.00   29
  5  ω    -74.00 -47.00   1.00    1.00    --  -17.77 -38.00 120.00   27
  6  ω   -107.00 -60.00   1.00    1.00    --  -17.77-178.00-150.00   47
  7  ω    -59.00  14.00   1.00    1.00    --  -17.77 -77.00 -60.00   73
  8  ω    -32.00  -1.00   1.00    1.00    --  -17.77 -38.00  90.00   31
  9  ω     -5.00  89.00   1.00    1.00    --   17.77  57.00  90.00   94
 10  ω      7.00  57.00   1.00    1.00    --   17.77 -98.00  81.00   50
 11  ω    121.00 148.00   1.00    5.00    --  101.41  61.00  90.00   27
 12  ω     69.00  96.00   1.00    5.00    --  101.41  77.00 150.00   27
 13  ω    116.00 178.00   1.00    5.00    --  101.41  77.00 150.00   62
 14  ω     72.00  99.00   1.00    5.00    --  101.41  61.00 120.00   27
 15  ω     70.00  95.00   1.00    5.00    --  101.41  77.00  90.00   25
 16  ω     72.00  98.00   1.00    5.00    --  101.41  61.00  90.00   26
 17  ω     77.00 120.00   1.00    5.00    --  101.41  45.00 150.00   43
 18  ω    117.00 144.00   1.00    5.00    --  101.41  61.00-180.00   27
 19  ω     73.00  98.00   1.00    5.00    --  101.41  61.00-180.00   25
 20  ω     51.00 113.00   1.00    5.00    --  101.41-125.00-180.00   62
 21  ω     73.00  99.00   1.00    5.00    --  101.41  61.00 150.00   26
 22  ω     30.00 128.00   1.00    5.00    --  101.41 -61.00-180.00   98
 23  ω    116.00 172.00   1.00    5.00    --  101.41  77.00-180.00   56
 24  ω     69.00  96.00   1.00    5.00    --  101.41  77.00 120.00   27
 25  ω    118.00 175.00   1.00    5.00    --  101.41  77.00 120.00   57
 26  ω     73.00 102.00   1.00    5.00    --  101.41  61.00-150.00   29
 27  ω     70.00 114.00   1.00    5.00    --  101.41  77.00-150.00   44
 28  ω    147.00 173.00   1.00    5.00    --  101.41  77.00-150.00   26
 29  ω     77.00 103.00   1.00    5.00    --  101.41  45.00-180.00   26
 30  ω     78.00 105.00   1.00    5.00    --  101.41  45.00 120.00   27
 31  ω     75.00 100.00   1.00    5.00    --  101.41  30.00 120.00   25
 32  ω     69.00  95.00   1.00    5.00    --  101.41  77.00-180.00   26
 33  ω     19.00 109.00   1.00    5.00    --  101.41 -94.00 -30.00   90
 34  ω     76.00 103.00   1.00    5.00    --  101.41  30.00-150.00   27
 35  ω     76.00 103.00   1.00    5.00    --  101.41  30.00 150.00   27
 36  ω    115.00 178.00   1.00    5.00    --  101.41  30.00  60.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1669379000
_diffrn_orient_matrix_UB_12      -0.0459115000
_diffrn_orient_matrix_UB_13      -0.0828295000
_diffrn_orient_matrix_UB_21      -0.1025747000
_diffrn_orient_matrix_UB_22      0.0180525000
_diffrn_orient_matrix_UB_23      0.0827934000
_diffrn_orient_matrix_UB_31      -0.0459906000
_diffrn_orient_matrix_UB_32      0.1265640000
_diffrn_orient_matrix_UB_33      -0.0418246000
_diffrn_oxdiff_ac3_digest_frames 
;
01ce9fc470d50645b54cdb0afff71c379f00031762f
;
_diffrn_oxdiff_ac3_digest_hkl    
;
011a1ba0913974d4ac2c80cfea3187a7161cd2
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1915
_reflns_number_total             2137
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_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         0.830
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.029
_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)+(0.0603P)²+0.8094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1155
_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:
 C2(H2), C6(H6), C7(H7), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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 0.45263(6) 0.86351(4) 0.66917(4) 0.0833(2) Uani 1 1 d . . . . .
S1 S 0.26501(12) 0.69652(9) 0.94074(6) 0.0644(3) Uani 1 1 d . . . . .
S2 S -0.00115(12) 0.72877(10) 0.72485(7) 0.0703(3) Uani 1 1 d . . . . .
N1 N 0.3280(3) 0.6427(2) 0.76798(19) 0.0485(5) Uani 1 1 d . . . . .
C1 C 0.1953(4) 0.6875(3) 0.8009(2) 0.0519(7) Uani 1 1 d . . . . .
C2 C 0.4657(5) 0.6385(3) 0.9469(3) 0.0605(8) Uani 1 1 d . . . . .
H2 H 0.553784 0.625981 1.010984 0.073 Uiso 1 1 calc R . . . .
C3 C 0.4807(4) 0.6136(3) 0.8495(2) 0.0536(7) Uani 1 1 d . . . . .
C4 C 0.6310(5) 0.5595(4) 0.8219(3) 0.0693(9) Uani 1 1 d . . . . .
H4A H 0.594425 0.487360 0.783055 0.104 Uiso 1 1 calc GR . . . .
H4B H 0.722340 0.543019 0.887057 0.104 Uiso 1 1 calc GR . . . .
H4C H 0.673521 0.612951 0.777867 0.104 Uiso 1 1 calc GR . . . .
C5 C 0.3140(4) 0.6298(3) 0.6551(2) 0.0501(7) Uani 1 1 d . . . . .
C6 C 0.2481(5) 0.5269(3) 0.6023(3) 0.0650(8) Uani 1 1 d . . . . .
H6 H 0.210486 0.466637 0.638886 0.078 Uiso 1 1 calc R . . . .
C7 C 0.2381(6) 0.5137(4) 0.4940(3) 0.0778(11) Uani 1 1 d . . . . .
H7 H 0.191422 0.445066 0.457549 0.093 Uiso 1 1 calc R . . . .
C8 C 0.2966(6) 0.6009(4) 0.4408(3) 0.0761(11) Uani 1 1 d . . . . .
H8 H 0.292200 0.590311 0.368857 0.091 Uiso 1 1 calc R . . . .
C9 C 0.3620(5) 0.7046(4) 0.4923(3) 0.0687(10) Uani 1 1 d . . . . .
H9 H 0.399975 0.764261 0.455218 0.082 Uiso 1 1 calc R . . . .
C10 C 0.3706(4) 0.7191(3) 0.5999(2) 0.0559(7) 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 C10 1.891(4) . ?
S1 C1 1.735(3) . ?
S1 C2 1.715(4) . ?
S2 C1 1.662(3) . ?
N1 C1 1.353(4) . ?
N1 C3 1.402(4) . ?
N1 C5 1.440(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.332(5) . ?
C3 C4 1.483(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.377(5) . ?
C5 C10 1.389(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.362(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(5) . ?

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 S1 C1 92.24(16) . . ?
C1 N1 C3 116.4(2) . . ?
C1 N1 C5 121.4(3) . . ?
C3 N1 C5 122.2(2) . . ?
S2 C1 S1 124.28(18) . . ?
N1 C1 S1 107.9(2) . . ?
N1 C1 S2 127.9(2) . . ?
S1 C2 H2 123.9 . . ?
C3 C2 S1 112.2(3) . . ?
C3 C2 H2 123.9 . . ?
N1 C3 C4 120.5(3) . . ?
C2 C3 N1 111.3(3) . . ?
C2 C3 C4 128.2(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 119.7(3) . . ?
C6 C5 C10 119.8(3) . . ?
C10 C5 N1 120.4(3) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.6(4) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 120.9(3) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.2(4) . . ?
C10 C9 H9 120.4 . . ?
C5 C10 Br1 120.5(2) . . ?
C9 C10 Br1 119.2(3) . . ?
C9 C10 C5 120.2(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 2.210
_oxdiff_exptl_absorpt_empirical_full_min 0.619
####################################################################### 
# 
# 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_se5br1
_database_code_depnum_ccdc_archive 'CCDC 1955659'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi' 'Aix Marseille Universite'
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_audit_creation_date             2017-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 Br N S Se'
_chemical_formula_sum            'C12 H10 Br N S Se'
_chemical_formula_weight         359.14
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c12 h10 Br1 n1 S1 Se1 '
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.49830(10)
_cell_length_b                   7.8011(2)
_cell_length_c                   21.5964(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1263.28(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7632
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.7660
_cell_measurement_theta_min      4.0650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.033
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
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    1.888
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11206
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.845
_diffrn_reflns_theta_min         4.094
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  92.00   1.00    1.00    --    0.00  57.00-150.00  134
  2  ω   -147.00 -79.00   1.00   10.00    --  -52.94 -99.00-150.00   68
  3  ω   -147.00 -79.00   1.00   10.00    --  -52.94 -99.00 150.00   68
  4  ω     94.00 145.00   1.00   10.00    --   52.94 125.00 -60.00   51
  5  ω    -47.00  96.00   1.00   10.00    --   52.94 -77.00  60.00  143
  6  ω     15.00 152.00   1.00   20.00    --  105.88 -38.00 -60.00  137
  7  ω     64.00 178.00   1.00   20.00    --  105.88  50.00-150.00  114
  8  ω     12.00 150.00   1.00   20.00    --  105.88 -63.00  90.00  138
  9  ω     59.00 178.00   1.00   20.00    --  105.88  38.00-180.00  119
 10  ω     18.00 118.00   1.00   20.00    --  105.88-118.00 111.00  100
 11  ω   -101.00 -35.00   1.00    1.00    --    0.00-178.00 -60.00   66
 12  ω   -145.00 -11.00   1.00   10.00    --  -52.94 -57.00  90.00  134
 13  ω   -144.00  -6.00   1.00   10.00    --  -52.94 -38.00-150.00  138
 14  ω   -144.00  -6.00   1.00   10.00    --  -52.94 -38.00 -30.00  138
 15  ω     59.00 178.00   1.00   20.00    --  105.88  38.00 -30.00  119
 16  ω     62.00 178.00   1.00   20.00    --  105.88  63.00  30.00  116
 17  ω    100.00 178.00   1.00   20.00    --  105.88 111.00  60.00   78
 18  ω     64.00 178.00   1.00   20.00    --  105.88  50.00 -90.00  114
 19  ω     62.00 178.00   1.00   20.00    --  105.88  63.00  90.00  116
 20  ω    -92.00  42.00   1.00    1.00    --    0.00 -57.00-150.00  134
 21  ω   -153.00-116.00   1.00   10.00    --  -52.94 -77.00-180.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1842338000
_diffrn_orient_matrix_UB_12      0.0234486000
_diffrn_orient_matrix_UB_13      0.0304082000
_diffrn_orient_matrix_UB_21      -0.0863863000
_diffrn_orient_matrix_UB_22      -0.0138642000
_diffrn_orient_matrix_UB_23      0.0645172000
_diffrn_orient_matrix_UB_31      0.0282937000
_diffrn_orient_matrix_UB_32      -0.1956185000
_diffrn_orient_matrix_UB_33      -0.0009570000
_diffrn_oxdiff_ac3_digest_frames 
;
01566d660f1d9561259bcb6f16fbc634e400031dc5e
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01537d13261c39bdd5ce080d65c47b74569f0e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2243
_reflns_number_total             2313
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_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         0.428
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 890 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.033(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0243
_refine_ls_restrained_S_all      1.072
_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)+(0.0271P)²+0.7769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0621
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
;
_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 0.64865(9) 0.20770(7) 0.65080(3) 0.06766(17) Uani 1 1 d . . . . .
Se1 Se 0.15204(6) 0.55366(8) 0.64624(2) 0.05597(16) Uani 1 1 d . . . . .
S1 S 0.25666(15) 0.48708(19) 0.50839(5) 0.0523(3) Uani 1 1 d . . . . .
N1 N 0.4965(4) 0.5353(5) 0.58908(15) 0.0408(8) Uani 1 1 d . . . . .
C1 C 0.3147(5) 0.5279(6) 0.58516(18) 0.0436(9) Uani 1 1 d . . . . .
C2 C 0.4778(6) 0.4846(7) 0.48492(19) 0.0477(10) Uani 1 1 d . . . . .
C3 C 0.5765(6) 0.4592(9) 0.4258(2) 0.0607(13) Uani 1 1 d . . . . .
H3A H 0.538600 0.540344 0.394407 0.073 Uiso 1 1 calc R . . . .
H3B H 0.562096 0.343491 0.410174 0.073 Uiso 1 1 calc R . . . .
C4 C 0.7706(7) 0.4935(9) 0.4467(2) 0.0658(14) Uani 1 1 d . . . . .
H4A H 0.846413 0.399194 0.433890 0.079 Uiso 1 1 calc R . . . .
H4B H 0.814427 0.597423 0.427327 0.079 Uiso 1 1 calc R . . . .
C5 C 0.7778(6) 0.5125(7) 0.5176(2) 0.0550(12) Uani 1 1 d . . . . .
H5A H 0.839390 0.416996 0.536774 0.066 Uiso 1 1 calc R . . . .
H5B H 0.834745 0.618954 0.529745 0.066 Uiso 1 1 calc R . . . .
C6 C 0.5850(5) 0.5125(6) 0.53300(18) 0.0424(9) Uani 1 1 d . . . . .
C7 C 0.5898(5) 0.5675(6) 0.6463(2) 0.0420(9) Uani 1 1 d . . . . .
C8 C 0.6061(7) 0.7345(7) 0.6673(2) 0.0548(12) Uani 1 1 d . . . . .
H8 H 0.554517 0.824355 0.645355 0.066 Uiso 1 1 calc R . . . .
C9 C 0.6998(7) 0.7663(7) 0.7210(2) 0.0618(14) Uani 1 1 d . . . . .
H9 H 0.711322 0.878330 0.735204 0.074 Uiso 1 1 calc R . . . .
C10 C 0.7756(7) 0.6359(8) 0.7536(2) 0.0595(13) Uani 1 1 d . . . . .
H10 H 0.838596 0.659834 0.789705 0.071 Uiso 1 1 calc R . . . .
C11 C 0.7599(6) 0.4686(7) 0.7337(2) 0.0546(12) Uani 1 1 d . . . . .
H11 H 0.810713 0.379607 0.756304 0.066 Uiso 1 1 calc R . . . .
C12 C 0.6670(6) 0.4353(6) 0.67936(18) 0.0425(9) 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 C12 1.884(4) . ?
Se1 C1 1.808(4) . ?
S1 C1 1.743(4) . ?
S1 C2 1.734(4) . ?
N1 C1 1.367(5) . ?
N1 C6 1.392(5) . ?
N1 C7 1.441(5) . ?
C2 C3 1.489(6) . ?
C2 C6 1.331(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.547(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.538(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.483(6) . ?
C7 C8 1.385(7) . ?
C7 C12 1.382(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.362(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(6) . ?

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 S1 C1 92.36(19) . . ?
C1 N1 C6 114.6(3) . . ?
C1 N1 C7 123.0(3) . . ?
C6 N1 C7 122.4(3) . . ?
S1 C1 Se1 123.1(2) . . ?
N1 C1 Se1 128.5(3) . . ?
N1 C1 S1 108.4(3) . . ?
C3 C2 S1 136.7(3) . . ?
C6 C2 S1 110.3(3) . . ?
C6 C2 C3 113.0(4) . . ?
C2 C3 H3A 111.5 . . ?
C2 C3 H3B 111.5 . . ?
C2 C3 C4 101.2(4) . . ?
H3A C3 H3B 109.3 . . ?
C4 C3 H3A 111.5 . . ?
C4 C3 H3B 111.5 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 C3 109.9(4) . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C4 C5 H5A 111.6 . . ?
C4 C5 H5B 111.6 . . ?
H5A C5 H5B 109.4 . . ?
C6 C5 C4 100.9(4) . . ?
C6 C5 H5A 111.6 . . ?
C6 C5 H5B 111.6 . . ?
N1 C6 C5 131.3(4) . . ?
C2 C6 N1 114.3(4) . . ?
C2 C6 C5 114.4(4) . . ?
C8 C7 N1 119.2(4) . . ?
C12 C7 N1 121.1(4) . . ?
C12 C7 C8 119.7(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.3(5) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.9(5) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.7(4) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 118.9(4) . . ?
C12 C11 H11 120.5 . . ?
C7 C12 Br1 120.2(3) . . ?
C7 C12 C11 120.5(4) . . ?
C11 C12 Br1 119.3(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C2 C3 C4 175.5(5) . . . . ?
S1 C2 C6 N1 0.4(6) . . . . ?
S1 C2 C6 C5 179.9(4) . . . . ?
N1 C7 C8 C9 -178.1(4) . . . . ?
N1 C7 C12 Br1 -1.0(5) . . . . ?
N1 C7 C12 C11 178.6(4) . . . . ?
C1 S1 C2 C3 180.0(6) . . . . ?
C1 S1 C2 C6 0.2(4) . . . . ?
C1 N1 C6 C2 -1.0(6) . . . . ?
C1 N1 C6 C5 179.6(5) . . . . ?
C1 N1 C7 C8 -80.8(6) . . . . ?
C1 N1 C7 C12 101.0(5) . . . . ?
C2 S1 C1 Se1 179.4(3) . . . . ?
C2 S1 C1 N1 -0.8(4) . . . . ?
C2 C3 C4 C5 7.6(7) . . . . ?
C3 C2 C6 N1 -179.5(5) . . . . ?
C3 C2 C6 C5 0.1(7) . . . . ?
C3 C4 C5 C6 -7.5(6) . . . . ?
C4 C5 C6 N1 -175.9(5) . . . . ?
C4 C5 C6 C2 4.7(6) . . . . ?
C6 N1 C1 Se1 -179.1(4) . . . . ?
C6 N1 C1 S1 1.1(5) . . . . ?
C6 N1 C7 C8 97.9(5) . . . . ?
C6 N1 C7 C12 -80.3(6) . . . . ?
C6 C2 C3 C4 -4.8(7) . . . . ?
C7 N1 C1 Se1 -0.3(7) . . . . ?
C7 N1 C1 S1 179.9(3) . . . . ?
C7 N1 C6 C2 -179.8(4) . . . . ?
C7 N1 C6 C5 0.8(8) . . . . ?
C7 C8 C9 C10 -0.2(8) . . . . ?
C8 C7 C12 Br1 -179.1(3) . . . . ?
C8 C7 C12 C11 0.4(6) . . . . ?
C8 C9 C10 C11 -0.2(9) . . . . ?
C9 C10 C11 C12 0.7(8) . . . . ?
C10 C11 C12 Br1 178.8(4) . . . . ?
C10 C11 C12 C7 -0.8(7) . . . . ?
C12 C7 C8 C9 0.1(7) . . . . ?

_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 1.731
_oxdiff_exptl_absorpt_empirical_full_min 0.586
####################################################################### 
# 
# 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_t5br1
_database_code_depnum_ccdc_archive 'CCDC 1955660'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi' 'Aix Marseille Universite'
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_audit_creation_date             2017-01-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 Br N S2'
_chemical_formula_sum            'C12 H10 Br N S2'
_chemical_formula_weight         312.24
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_symmetry_space_group_name_H-M_alt 'P 21 21 21'
_cell_length_a                   7.39679(7)
_cell_length_b                   7.70635(7)
_cell_length_c                   21.7345(2)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     1238.91(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10538
_cell_measurement_temperature    293
_cell_measurement_theta_max      67.5830
_cell_measurement_theta_min      4.0630
_cell_oxdiff_angle_alpha         89.9903(15)
_cell_oxdiff_angle_beta          89.9863(15)
_cell_oxdiff_angle_gamma         89.9915(14)
_cell_oxdiff_length_a            7.39720(13)
_cell_oxdiff_length_b            7.70615(14)
_cell_oxdiff_length_c            21.7339(4)
_cell_oxdiff_measurement_reflns_used 10538
_cell_oxdiff_volume              1238.91(4)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.425
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.674
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0105
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14017
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.648
_diffrn_reflns_theta_max         67.648
_diffrn_reflns_theta_min         4.068
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  58.00   1.00    1.00    --    0.00  77.00   0.00   97
  2  ω     63.00 103.00   1.00    1.00    --    0.00  77.00   0.00   40
  3  ω     59.00 103.00   1.00    1.00    --    0.00 178.00 -30.00   44
  4  ω    109.00 158.00   1.00    2.00    --   54.32 125.00-150.00   49
  5  ω    118.00 173.00   1.00    2.00    --   74.00  71.00-123.52   55
  6  ω    122.00 149.00   1.00    2.00    --   74.00  68.00 -21.62   27
  7  ω    147.00 172.00   1.00    5.00    --   86.00  65.00  36.67   25
  8  ω    147.00 178.00   1.00    5.00    --  108.65 104.00   0.00   31
  9  ω    123.00 176.00   1.00    5.00    --  108.65 104.00 -30.00   53
 10  ω    125.00 171.00   1.00    5.00    --  108.65 104.00-120.00   46
 11  ω     95.00 176.00   1.00    5.00    --  108.65  77.00  30.00   81
 12  ω    132.00 175.00   1.00    2.00    --   70.00  68.00 131.96   43
 13  ω    152.00 178.00   1.00    2.00    --   74.00  71.00 147.45   26
 14  ω     58.00 176.00   1.00    5.00    --  108.65  77.00  90.00  118
 15  ω     59.00  86.00   1.00    5.00    --  108.65  63.00  60.00   27
 16  ω     58.00 178.00   1.00    5.00    --  108.65  77.00  60.00  120
 17  ω     71.00  98.00   1.00    1.00    --    0.00  77.00-150.00   27
 18  ω     67.00  94.00   1.00    2.00    --   62.00  77.00-147.56   27
 19  ω     59.00 176.00   1.00    5.00    --  108.65  77.00 -60.00  117
 20  ω     58.00 149.00   1.00    5.00    --  108.65  77.00 -30.00   91
 21  ω     59.00 178.00   1.00    5.00    --  108.65  77.00-150.00  119
 22  ω     58.00 164.00   1.00    5.00    --  108.65  77.00   0.00  106
 23  ω     59.00 155.00   1.00    5.00    --  108.65  77.00-180.00   96
 24  ω     58.00 145.00   1.00    5.00    --  108.65  77.00-120.00   87
 25  ω     58.00  84.00   1.00    5.00    --  108.65  77.00  30.00   26
 26  ω     58.00 175.00   1.00    5.00    --  108.65  77.00 120.00  117
 27  ω     58.00 178.00   1.00    5.00    --  108.65  77.00 -90.00  120
 28  ω     58.00 177.00   1.00    5.00    --  108.65  77.00 150.00  119
 29  ω     49.00  74.00   1.00    5.00    --  108.65-104.00   0.00   25
 30  ω     60.00 111.00   1.00    5.00    --  108.65-104.00  30.00   51
 31  ω     50.00 103.00   1.00    5.00    --  108.65-104.00 -60.00   53
 32  ω     57.00 113.00   1.00    5.00    --  108.65-104.00-180.00   56
 33  ω     18.00  94.00   1.00    2.00    --   70.00  68.00 -56.98   76
 34  ω     34.00  68.00   1.00    5.00    --   86.00  65.00  36.67   34
 35  ω     23.00  95.00   1.00    2.00    --   74.00  68.00 -21.62   72
 36  ω     24.00  87.00   1.00    2.00    --   74.00  71.00-123.52   63
 37  ω     16.00  48.00   1.00    2.00    --   66.00  78.00-118.28   32
 38  ω      7.00  46.00   1.00    2.00    --   58.00  81.00 -54.10   39
 39  ω     11.00  36.00   1.00    2.00    --   62.00  84.00 -55.21   25
 40  ω     -2.00  23.00   1.00    2.00    --   54.32  95.00 -43.48   25
 41  ω      7.00  32.00   1.00    2.00    --   58.00  80.00  27.56   25
 42  ω     13.00  45.00   1.00    2.00    --   58.00  80.00  50.14   32
 43  ω     11.00  36.00   1.00    2.00    --   62.00  79.00 119.89   25
 44  ω     23.00  66.00   1.00    2.00    --   74.00  71.00 147.45   43
 45  ω     41.00 128.00   1.00    2.00    --   70.00  68.00 170.46   87
 46  ω     20.00  50.00   1.00    2.00    --   70.00  68.00 131.96   30
 47  ω      8.00 158.00   1.00    2.00    --   54.32  45.00 120.00  150
 48  ω     32.00 144.00   1.00    5.00    --  108.65 -91.00  60.00  112
 49  ω      9.00  68.00   1.00    1.00    --    0.00  77.00-150.00   59
 50  ω     -2.00  23.00   1.00    2.00    --   54.32  95.00  85.49   25
 51  ω      8.00  33.00   1.00    2.00    --   58.00  88.00 132.24   25
 52  ω    -89.00 -57.00   1.00    1.00    --    0.00 178.00  90.00   32
 53  ω    -95.00 -19.00   1.00    2.00    --  -54.32 125.00 -90.00   76
 54  ω    -51.00 -23.00   1.00    1.00    --    0.00  77.00-150.00   28
 55  ω    -44.00 -12.00   1.00    1.00    --   14.00 132.00-114.97   32
 56  ω     -1.00  24.00   1.00    2.00    --   54.32  94.00-153.38   25
 57  ω     12.00  45.00   1.00    2.00    --   62.00  77.00-147.56   33
 58  ω    -98.00  32.00   1.00    2.00    --  -54.32  77.00-120.00  130
 59  ω   -162.00  46.00   1.00    2.00    --  -54.32  15.00-120.00  208
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0706271000
_diffrn_orient_matrix_UB_12      -0.1244447000
_diffrn_orient_matrix_UB_13      -0.0499800000
_diffrn_orient_matrix_UB_21      -0.0141789000
_diffrn_orient_matrix_UB_22      -0.1462367000
_diffrn_orient_matrix_UB_23      0.0480986000
_diffrn_orient_matrix_UB_31      -0.1954079000
_diffrn_orient_matrix_UB_32      0.0556210000
_diffrn_orient_matrix_UB_33      0.0145924000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2202
_reflns_number_total             2225
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 885 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0208
_refine_ls_restrained_S_all      1.095
_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)+(0.0250P)²+0.5649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0546
_refine_ls_wR_factor_ref         0.0548
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.83276(6) 0.80249(5) 0.65118(2) 0.06228(14) Uani 1 1 d . . . . .
S1 S 1.23625(10) 0.51417(13) 0.51066(3) 0.0472(2) Uani 1 1 d . . . . .
S2 S 1.33115(11) 0.45859(14) 0.64368(4) 0.0535(2) Uani 1 1 d . . . . .
N1 N 0.9961(3) 0.4698(4) 0.59271(11) 0.0356(5) Uani 1 1 d . . . . .
C1 C 0.9047(4) 0.4873(4) 0.53717(13) 0.0372(6) Uani 1 1 d . . . . .
C2 C 0.7086(4) 0.4842(5) 0.52251(16) 0.0490(8) Uani 1 1 d . . . . .
H2A H 0.645629 0.581656 0.540923 0.059 Uiso 1 1 calc R . . . .
H2B H 0.652448 0.376833 0.535820 0.059 Uiso 1 1 calc R . . . .
C3 C 0.7134(5) 0.4984(6) 0.45161(17) 0.0576(9) Uani 1 1 d . . . . .
H3A H 0.667605 0.392112 0.433497 0.069 Uiso 1 1 calc R . . . .
H3B H 0.636731 0.593382 0.438319 0.069 Uiso 1 1 calc R . . . .
C4 C 0.9086(5) 0.5302(6) 0.42977(15) 0.0546(9) Uani 1 1 d . . . . .
H4A H 0.946089 0.444062 0.399817 0.066 Uiso 1 1 calc R . . . .
H4B H 0.922601 0.645141 0.412249 0.066 Uiso 1 1 calc R . . . .
C5 C 1.0114(4) 0.5122(4) 0.48873(14) 0.0412(7) Uani 1 1 d . . . . .
C6 C 1.1802(4) 0.4788(4) 0.58798(13) 0.0378(6) Uani 1 1 d . . . . .
C7 C 0.9034(4) 0.4394(4) 0.64994(14) 0.0361(6) Uani 1 1 d . . . . .
C8 C 0.8932(5) 0.2727(5) 0.67281(16) 0.0506(9) Uani 1 1 d . . . . .
H8 H 0.949946 0.182305 0.652065 0.061 Uiso 1 1 calc R . . . .
C9 C 0.7992(6) 0.2396(5) 0.72630(17) 0.0602(10) Uani 1 1 d . . . . .
H9 H 0.791119 0.126959 0.741390 0.072 Uiso 1 1 calc R . . . .
C10 C 0.7172(5) 0.3742(5) 0.75729(16) 0.0558(9) Uani 1 1 d . . . . .
H10 H 0.653615 0.351534 0.793321 0.067 Uiso 1 1 calc R . . . .
C11 C 0.7281(5) 0.5418(5) 0.73564(15) 0.0501(8) Uani 1 1 d . . . . .
H11 H 0.673824 0.632478 0.756968 0.060 Uiso 1 1 calc R . . . .
C12 C 0.8217(5) 0.5727(4) 0.68136(14) 0.0392(6) 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 C12 1.890(3) . ?
S1 C5 1.730(3) . ?
S1 C6 1.752(3) . ?
S2 C6 1.654(3) . ?
N1 C1 1.390(4) . ?
N1 C6 1.367(4) . ?
N1 C7 1.439(4) . ?
C1 C2 1.486(4) . ?
C1 C5 1.329(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.545(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.539(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.497(4) . ?
C7 C8 1.379(5) . ?
C7 C12 1.374(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(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
C5 S1 C6 92.03(14) . . ?
C1 N1 C7 122.3(2) . . ?
C6 N1 C1 114.5(2) . . ?
C6 N1 C7 123.2(2) . . ?
N1 C1 C2 131.3(3) . . ?
C5 C1 N1 114.4(3) . . ?
C5 C1 C2 114.3(3) . . ?
C1 C2 H2A 111.6 . . ?
C1 C2 H2B 111.6 . . ?
C1 C2 C3 101.0(3) . . ?
H2A C2 H2B 109.4 . . ?
C3 C2 H2A 111.6 . . ?
C3 C2 H2B 111.6 . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 C2 109.9(3) . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C3 C4 H4A 111.5 . . ?
C3 C4 H4B 111.5 . . ?
H4A C4 H4B 109.3 . . ?
C5 C4 C3 101.4(3) . . ?
C5 C4 H4A 111.5 . . ?
C5 C4 H4B 111.5 . . ?
C1 C5 S1 110.7(2) . . ?
C1 C5 C4 113.0(3) . . ?
C4 C5 S1 136.3(2) . . ?
S2 C6 S1 123.85(19) . . ?
N1 C6 S1 108.4(2) . . ?
N1 C6 S2 127.8(2) . . ?
C8 C7 N1 119.3(3) . . ?
C12 C7 N1 121.2(3) . . ?
C12 C7 C8 119.5(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.7(3) . . ?
C12 C11 H11 120.6 . . ?
C7 C12 Br1 120.6(2) . . ?
C7 C12 C11 120.9(3) . . ?
C11 C12 Br1 118.5(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 1.375
_oxdiff_exptl_absorpt_empirical_full_min 0.711
####################################################################### 
# 
# 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_t6br1
_database_code_depnum_ccdc_archive 'CCDC 1955661'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi' 'Aix Marseille Universite'
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_audit_creation_date             2017-06-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 Br N S2'
_chemical_formula_sum            'C13 H12 Br N S2'
_chemical_formula_weight         326.27
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c13 h12 Br1 n1 s2'
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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.52800(10)
_cell_length_b                   7.78550(10)
_cell_length_c                   15.4344(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.9970(10)
_cell_angle_gamma                90
_cell_volume                     1383.36(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    38245
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.8970
_cell_measurement_theta_min      3.8090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
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    1.567
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            61001
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.021
_diffrn_reflns_theta_min         3.840
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -35.00   1.00    1.00    --  -17.77-178.00 -30.00   72
  2  ω   -107.00 -35.00   1.00    1.00    --  -17.77-178.00-120.00   72
  3  ω    -91.00  10.00   1.00    1.00    --  -17.77 -57.00 120.00  101
  4  ω     55.00 105.00   1.00    1.00    --   17.77-178.00  60.00   50
  5  ω    -10.00  91.00   1.00    1.00    --   17.77  57.00 120.00  101
  6  ω    -15.00  94.00   1.00    1.00    --   17.77  77.00-120.00  109
  7  ω     28.00 121.00   1.00    5.00    --  101.41-125.00-120.00   93
  8  ω     76.00 174.00   1.00    5.00    --  101.41  45.00-120.00   98
  9  ω     94.00 175.00   1.00    5.00    --  101.41 125.00-180.00   81
 10  ω     28.00 121.00   1.00    5.00    --  101.41-125.00  60.00   93
 11  ω     28.00 127.00   1.00    5.00    --  101.41 -45.00-180.00   99
 12  ω     94.00 175.00   1.00    5.00    --  101.41 125.00-120.00   81
 13  ω     72.00 174.00   1.00    5.00    --  101.41  61.00   0.00  102
 14  ω     72.00 174.00   1.00    5.00    --  101.41  61.00-180.00  102
 15  ω     76.00 174.00   1.00    5.00    --  101.41  45.00  60.00   98
 16  ω     29.00 130.00   1.00    5.00    --  101.41 -61.00  60.00  101
 17  ω     25.00 134.00   1.00    5.00    --  101.41 -77.00-120.00  109
 18  ω    -94.00  15.00   1.00    1.00    --  -17.77 -77.00 -60.00  109
 19  ω    -42.00  57.00   1.00    1.00    --  -17.77  38.00-150.00   99
 20  ω    -98.00  23.00   1.00    1.00    --  -17.77 -19.00 -60.00  121
 21  ω     29.00  78.00   1.00    1.00    --   17.77-133.00-126.00   49
 22  ω     57.00 107.00   1.00    1.00    --   17.77 178.00  30.00   50
 23  ω     72.00 174.00   1.00    5.00    --  101.41  61.00 -60.00  102
 24  ω     72.00 174.00   1.00    5.00    --  101.41  61.00  30.00  102
 25  ω     72.00 174.00   1.00    5.00    --  101.41  61.00 120.00  102
 26  ω     72.00 174.00   1.00    5.00    --  101.41  61.00 150.00  102
 27  ω     72.00 174.00   1.00    5.00    --  101.41  61.00 -30.00  102
 28  ω     72.00 174.00   1.00    5.00    --  101.41  61.00 -90.00  102
 29  ω     72.00 174.00   1.00    5.00    --  101.41  61.00-150.00  102
 30  ω     72.00 174.00   1.00    5.00    --  101.41  61.00  60.00  102
 31  ω     72.00 174.00   1.00    5.00    --  101.41  61.00-120.00  102
 32  ω     72.00 174.00   1.00    5.00    --  101.41  61.00  90.00  102
 33  ω    -92.00   7.00   1.00    1.00    --  -17.77 -38.00 -90.00   99
 34  ω    -98.00  23.00   1.00    1.00    --  -17.77 -19.00 120.00  121
 35  ω      1.00  59.00   1.00    1.00    --   17.77 -99.00 -60.00   58
 36  ω     30.00  80.00   1.00    1.00    --   17.77-136.00  55.00   50
 37  ω      1.00  59.00   1.00    1.00    --   17.77 -99.00 150.00   58
 38  ω     69.00 178.00   1.00    5.00    --  101.41  77.00-180.00  109
 39  ω     69.00 178.00   1.00    5.00    --  101.41  77.00 -90.00  109
 40  ω     69.00 178.00   1.00    5.00    --  101.41  77.00 -60.00  109
 41  ω     69.00 178.00   1.00    5.00    --  101.41  77.00 -30.00  109
 42  ω     69.00 178.00   1.00    5.00    --  101.41  77.00-120.00  109
 43  ω     76.00 174.00   1.00    5.00    --  101.41  45.00 150.00   98
 44  ω     69.00 178.00   1.00    5.00    --  101.41  77.00   0.00  109
 45  ω     69.00 178.00   1.00    5.00    --  101.41  77.00  60.00  109
 46  ω     69.00 178.00   1.00    5.00    --  101.41  77.00 150.00  109
 47  ω     69.00 178.00   1.00    5.00    --  101.41  77.00  90.00  109
 48  ω    -92.00   7.00   1.00    1.00    --  -17.77 -38.00 120.00   99
 49  ω    -92.00   7.00   1.00    1.00    --  -17.77 -38.00  60.00   99
 50  ω    -91.00  10.00   1.00    1.00    --  -17.77 -57.00  60.00  101
 51  ω    -98.00  23.00   1.00    1.00    --  -17.77 -19.00-120.00  121
 52  ω     -7.00  92.00   1.00    1.00    --   17.77  38.00 150.00   99
 53  ω     69.00 178.00   1.00    5.00    --  101.41  77.00  30.00  109
 54  ω     76.00 174.00   1.00    5.00    --  101.41  45.00 -60.00   98
 55  ω     69.00 178.00   1.00    5.00    --  101.41  77.00-150.00  109
 56  ω     76.00 174.00   1.00    5.00    --  101.41  45.00-150.00   98
 57  ω     76.00 174.00   1.00    5.00    --  101.41  45.00-180.00   98
 58  ω     76.00 174.00   1.00    5.00    --  101.41  45.00 -90.00   98
 59  ω     76.00 174.00   1.00    5.00    --  101.41  45.00 -30.00   98
 60  ω     76.00 174.00   1.00    5.00    --  101.41  45.00   0.00   98
 61  ω     76.00 174.00   1.00    5.00    --  101.41  45.00  90.00   98
 62  ω     69.00 178.00   1.00    5.00    --  101.41  77.00 120.00  109
 63  ω    -50.00  58.00   1.00    1.00    --  -17.77  77.00  30.00  108
 64  ω    -46.00  55.00   1.00    1.00    --  -17.77  57.00   0.00  101
 65  ω      1.00  59.00   1.00    1.00    --   17.77 -99.00  90.00   58
 66  ω     -7.00  92.00   1.00    1.00    --   17.77  38.00   0.00   99
 67  ω      1.00  59.00   1.00    1.00    --   17.77 -99.00-150.00   58
 68  ω     76.00 174.00   1.00    5.00    --  101.41  45.00 120.00   98
 69  ω     73.00 178.00   1.00    5.00    --  101.41  30.00 -60.00  105
 70  ω     76.00 174.00   1.00    5.00    --  101.41  45.00  30.00   98
 71  ω     73.00 178.00   1.00    5.00    --  101.41  30.00-120.00  105
 72  ω     73.00 178.00   1.00    5.00    --  101.41  30.00-150.00  105
 73  ω     73.00 178.00   1.00    5.00    --  101.41  30.00 150.00  105
 74  ω     73.00 178.00   1.00    5.00    --  101.41  30.00  30.00  105
 75  ω     49.00 178.00   1.00    5.00    --  101.41  15.00-150.00  129
 76  ω     49.00 167.00   1.00    5.00    --  101.41  15.00 -90.00  118
 77  ω     73.00 178.00   1.00    5.00    --  101.41  30.00  90.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1275628000
_diffrn_orient_matrix_UB_12      0.0068605000
_diffrn_orient_matrix_UB_13      0.0250952000
_diffrn_orient_matrix_UB_21      0.0044806000
_diffrn_orient_matrix_UB_22      0.1977202000
_diffrn_orient_matrix_UB_23      -0.0006688000
_diffrn_orient_matrix_UB_31      -0.0404347000
_diffrn_orient_matrix_UB_32      0.0003385000
_diffrn_orient_matrix_UB_33      -0.0967106000
_diffrn_oxdiff_ac3_digest_frames 
;
019ffc11be494b4f0f3f6a2e839a4e923c00030e0e1
;
_diffrn_oxdiff_ac3_digest_hkl    
;
0193a07ddeeaaaa351c105601a50d7ad0cf661
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                5164
_reflns_number_total             5289
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_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         0.280
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 2278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5289
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.037
_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)+(0.0542P)²+0.3149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0941
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H15A(0.5) H15B(0.5) H15C(0.5) H15D(0.5) C16(0.5) H16A(0.5)
 H16B(0.5) C17(0.5) H17A(0.5) H17B(0.5) H18A(0.5) H18B(0.5) H18C(0.5) H18D(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C15(H15A,H15B), C15(H15C,
 H15D), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C18(H18C,H18D),
 C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C24(H24), C25(H25), C26(H26), C27(H27)
;
_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 0.75744(4) 0.57450(10) -0.06226(4) 0.0879(2) Uani 1 1 d . . . . .
S1 S 0.53284(9) 0.22963(17) 0.10108(9) 0.0710(3) Uani 1 1 d . . . . .
S2 S 0.77415(10) 0.10696(17) 0.07292(9) 0.0747(3) Uani 1 1 d . . . . .
N1 N 0.7051(3) 0.4262(4) 0.1176(2) 0.0563(8) Uani 1 1 d . . . . .
C1 C 0.5090(4) 0.4397(6) 0.1316(3) 0.0616(10) Uani 1 1 d . . . . .
C2 C 0.3929(4) 0.5119(8) 0.1506(4) 0.0778(14) Uani 1 1 d . . . . .
H2A H 0.352304 0.432725 0.186867 0.093 Uiso 1 1 calc R . . . .
H2B H 0.346604 0.527532 0.096836 0.093 Uiso 1 1 calc R . . . .
C3 C 0.4087(6) 0.6814(11) 0.1961(6) 0.109(2) Uani 1 1 d . . . . .
H3A H 0.336551 0.745059 0.188968 0.131 Uiso 1 1 calc R . . . .
H3B H 0.422616 0.659362 0.257661 0.131 Uiso 1 1 calc R . . . .
C4 C 0.5008(7) 0.7882(10) 0.1679(7) 0.119(3) Uani 1 1 d . . . . .
H4A H 0.506904 0.886880 0.206305 0.143 Uiso 1 1 calc R . . . .
H4B H 0.477892 0.830850 0.110512 0.143 Uiso 1 1 calc R . . . .
C5 C 0.6208(5) 0.7099(7) 0.1640(4) 0.0781(13) Uani 1 1 d . . . . .
H5A H 0.665373 0.772587 0.122764 0.094 Uiso 1 1 calc R . . . .
H5B H 0.661442 0.716874 0.220490 0.094 Uiso 1 1 calc R . . . .
C6 C 0.6090(4) 0.5272(6) 0.1368(3) 0.0576(9) Uani 1 1 d . . . . .
C7 C 0.6805(4) 0.2602(6) 0.0974(3) 0.0573(9) Uani 1 1 d . . . . .
C8 C 0.8207(3) 0.4949(6) 0.1140(3) 0.0576(9) Uani 1 1 d . . . . .
C9 C 0.8568(3) 0.5694(6) 0.0393(3) 0.0616(10) Uani 1 1 d . . . . .
C10 C 0.9672(4) 0.6387(7) 0.0353(4) 0.0765(14) Uani 1 1 d . . . . .
H10 H 0.990588 0.690807 -0.015168 0.092 Uiso 1 1 calc R . . . .
C11 C 1.0410(4) 0.6284(9) 0.1078(4) 0.0847(16) Uani 1 1 d . . . . .
H11 H 1.115499 0.673545 0.106201 0.102 Uiso 1 1 calc R . . . .
C12 C 1.0068(4) 0.5525(9) 0.1828(4) 0.0851(15) Uani 1 1 d . . . . .
H12 H 1.058631 0.544766 0.230912 0.102 Uiso 1 1 calc R . . . .
C13 C 0.8960(4) 0.4880(7) 0.1867(4) 0.0741(13) Uani 1 1 d . . . . .
H13 H 0.871830 0.440079 0.237934 0.089 Uiso 1 1 calc R . . . .
Br2 Br 0.29915(6) 0.89303(9) 0.61180(5) 0.0927(2) Uani 1 1 d . . . . .
S3 S 0.00967(9) 0.5875(2) 0.44917(8) 0.0741(3) Uani 1 1 d . . . . .
S4 S 0.24576(10) 0.5754(2) 0.37583(8) 0.0806(4) Uani 1 1 d . . . . .
N2 N 0.1920(3) 0.5504(5) 0.5441(2) 0.0565(7) Uani 1 1 d . . . . .
C14 C -0.0031(3) 0.5687(6) 0.5596(3) 0.0624(10) Uani 1 1 d . . . . .
C15 C -0.1170(4) 0.5711(9) 0.6036(4) 0.0807(14) Uani 1 1 d . . . . .
H15A H -0.174458 0.504780 0.569808 0.097 Uiso 0.5 1 calc R . P A 1
H15B H -0.144917 0.688188 0.607376 0.097 Uiso 0.5 1 calc R . P A 1
H15C H -0.168090 0.658054 0.577692 0.097 Uiso 0.5 1 calc R . P B 2
H15D H -0.155120 0.460343 0.597577 0.097 Uiso 0.5 1 calc R . P B 2
C16 C -0.0989(11) 0.491(3) 0.6986(9) 0.095(4) Uani 0.5 1 d . . P C 1
H16A H -0.157649 0.538528 0.734513 0.114 Uiso 0.5 1 calc R . P C 1
H16B H -0.112067 0.368202 0.694713 0.114 Uiso 0.5 1 calc R . P C 1
C17 C -0.0896(9) 0.610(2) 0.6966(9) 0.083(3) Uani 0.5 1 d . . P C 2
H17A H -0.072720 0.732198 0.701705 0.099 Uiso 0.5 1 calc R . P C 2
H17B H -0.158617 0.588523 0.728218 0.099 Uiso 0.5 1 calc R . P C 2
C18 C 0.0052(6) 0.5177(16) 0.7385(4) 0.124(3) Uani 1 1 d . . . . .
H18A H 0.012779 0.431811 0.783984 0.149 Uiso 0.5 1 calc R . P C 1
H18B H -0.000270 0.627572 0.767608 0.149 Uiso 0.5 1 calc R . P C 1
H18C H -0.018584 0.398830 0.743889 0.149 Uiso 0.5 1 calc R . P C 2
H18D H 0.017560 0.562896 0.796817 0.149 Uiso 0.5 1 calc R . P C 2
C19 C 0.1207(4) 0.5196(8) 0.6964(3) 0.0745(13) Uani 1 1 d . . . . .
H19A H 0.169287 0.610453 0.721433 0.089 Uiso 1 1 calc R . . . .
H19B H 0.160309 0.411040 0.706588 0.089 Uiso 1 1 calc R . . . .
C20 C 0.1008(3) 0.5486(6) 0.6011(3) 0.0579(9) Uani 1 1 d . . . . .
C21 C 0.1597(3) 0.5694(6) 0.4584(3) 0.0601(9) Uani 1 1 d . . . . .
C22 C 0.3125(3) 0.5361(7) 0.5715(3) 0.0601(10) Uani 1 1 d . . . . .
C23 C 0.3731(4) 0.6773(8) 0.6028(3) 0.0669(11) Uani 1 1 d . . . . .
C24 C 0.4914(5) 0.6612(11) 0.6272(4) 0.097(2) Uani 1 1 d . . . . .
H24 H 0.533325 0.754939 0.649292 0.116 Uiso 1 1 calc R . . . .
C25 C 0.5450(5) 0.5030(14) 0.6179(5) 0.110(3) Uani 1 1 d . . . . .
H25 H 0.623526 0.491623 0.633739 0.132 Uiso 1 1 calc R . . . .
C26 C 0.4852(6) 0.3651(14) 0.5861(4) 0.107(3) Uani 1 1 d . . . . .
H26 H 0.523098 0.260813 0.579528 0.128 Uiso 1 1 calc R . . . .
C27 C 0.3673(5) 0.3792(9) 0.5633(3) 0.0811(14) Uani 1 1 d . . . . .
H27 H 0.325558 0.284042 0.542688 0.097 Uiso 1 1 calc R . . . .


_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 C9 1.893(4) . ?
S1 C1 1.728(5) . ?
S1 C7 1.723(4) . ?
S2 C7 1.665(5) . ?
N1 C6 1.402(5) . ?
N1 C7 1.356(6) . ?
N1 C8 1.440(5) . ?
C1 C2 1.495(6) . ?
C1 C6 1.338(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.502(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.434(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.516(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.487(7) . ?
C8 C9 1.374(6) . ?
C8 C13 1.383(7) . ?
C9 C10 1.387(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(7) . ?
C13 H13 0.9300 . ?
Br2 C23 1.892(6) . ?
S3 C14 1.724(4) . ?
S3 C21 1.734(4) . ?
S4 C21 1.656(4) . ?
N2 C20 1.406(5) . ?
N2 C21 1.364(5) . ?
N2 C22 1.436(5) . ?
C14 C15 1.509(6) . ?
C14 C20 1.338(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C15 H15D 0.9700 . ?
C15 C16 1.597(16) . ?
C15 C17 1.487(14) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C18 H18D 0.9700 . ?
C18 C19 1.512(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.492(7) . ?
C22 C23 1.376(7) . ?
C22 C27 1.384(8) . ?
C23 C24 1.401(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.389(12) . ?
C25 H25 0.9300 . ?
C25 C26 1.354(13) . ?
C26 H26 0.9300 . ?
C26 C27 1.391(8) . ?
C27 H27 0.9300 . ?

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
C7 S1 C1 92.8(2) . . ?
C6 N1 C8 122.9(4) . . ?
C7 N1 C6 115.2(3) . . ?
C7 N1 C8 121.8(4) . . ?
C2 C1 S1 124.5(4) . . ?
C6 C1 S1 110.5(3) . . ?
C6 C1 C2 125.1(5) . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
C1 C2 C3 109.5(5) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C2 C3 H3A 108.2 . . ?
C2 C3 H3B 108.2 . . ?
H3A C3 H3B 107.4 . . ?
C4 C3 C2 116.2(6) . . ?
C4 C3 H3A 108.2 . . ?
C4 C3 H3B 108.2 . . ?
C3 C4 H4A 107.8 . . ?
C3 C4 H4B 107.8 . . ?
C3 C4 C5 118.0(6) . . ?
H4A C4 H4B 107.1 . . ?
C5 C4 H4A 107.8 . . ?
C5 C4 H4B 107.8 . . ?
C4 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C6 C5 C4 109.0(5) . . ?
C6 C5 H5A 109.9 . . ?
C6 C5 H5B 109.9 . . ?
N1 C6 C5 122.3(4) . . ?
C1 C6 N1 112.9(4) . . ?
C1 C6 C5 124.7(4) . . ?
S2 C7 S1 124.2(3) . . ?
N1 C7 S1 108.6(3) . . ?
N1 C7 S2 127.2(3) . . ?
C9 C8 N1 120.7(4) . . ?
C9 C8 C13 119.5(4) . . ?
C13 C8 N1 119.8(4) . . ?
C8 C9 Br1 120.4(3) . . ?
C8 C9 C10 121.4(4) . . ?
C10 C9 Br1 118.1(4) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.1(5) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.3(4) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(5) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 H13 120.2 . . ?
C12 C13 C8 119.6(5) . . ?
C12 C13 H13 120.2 . . ?
C14 S3 C21 92.78(19) . . ?
C20 N2 C22 124.0(4) . . ?
C21 N2 C20 115.7(3) . . ?
C21 N2 C22 120.3(3) . . ?
C15 C14 S3 124.4(3) . . ?
C20 C14 S3 111.3(3) . . ?
C20 C14 C15 124.3(4) . . ?
C14 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
C14 C15 H15C 110.3 . . ?
C14 C15 H15D 110.3 . . ?
C14 C15 C16 109.5(6) . . ?
C19 C18 H18A 105.7 . . ?
C19 C18 H18B 105.7 . . ?
C19 C18 H18C 107.8 . . ?
C19 C18 H18D 107.8 . . ?
C18 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 C18 109.4(5) . . ?
C20 C19 H19A 109.8 . . ?
C20 C19 H19B 109.8 . . ?
N2 C20 C19 122.4(4) . . ?
C14 C20 N2 112.2(4) . . ?
C14 C20 C19 125.3(4) . . ?
S4 C21 S3 124.7(2) . . ?
N2 C21 S3 108.0(3) . . ?
N2 C21 S4 127.3(3) . . ?
C23 C22 N2 120.5(4) . . ?
C23 C22 C27 120.8(4) . . ?
C27 C22 N2 118.7(5) . . ?
C22 C23 Br2 120.8(3) . . ?
C22 C23 C24 119.5(6) . . ?
C24 C23 Br2 119.7(5) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 C23 118.9(7) . . ?
C25 C24 H24 120.6 . . ?
C24 C25 H25 119.3 . . ?
C26 C25 C24 121.4(5) . . ?
C26 C25 H25 119.3 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.1(7) . . ?
C27 C26 H26 120.0 . . ?
C22 C27 C26 119.4(7) . . ?
C22 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?

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 C9 C10 C11 -177.2(5) . . . . ?
S1 C1 C2 C3 165.7(5) . . . . ?
S1 C1 C6 N1 -0.8(5) . . . . ?
S1 C1 C6 C5 -178.0(4) . . . . ?
N1 C8 C9 Br1 -2.8(6) . . . . ?
N1 C8 C9 C10 178.9(5) . . . . ?
N1 C8 C13 C12 179.4(5) . . . . ?
C1 S1 C7 S2 178.9(3) . . . . ?
C1 S1 C7 N1 -1.1(4) . . . . ?
C1 C2 C3 C4 37.3(9) . . . . ?
C2 C1 C6 N1 178.4(5) . . . . ?
C2 C1 C6 C5 1.2(8) . . . . ?
C2 C3 C4 C5 -51.7(12) . . . . ?
C3 C4 C5 C6 35.3(10) . . . . ?
C4 C5 C6 N1 172.5(5) . . . . ?
C4 C5 C6 C1 -10.6(8) . . . . ?
C6 N1 C7 S1 0.8(5) . . . . ?
C6 N1 C7 S2 -179.1(3) . . . . ?
C6 N1 C8 C9 -85.3(6) . . . . ?
C6 N1 C8 C13 93.9(6) . . . . ?
C6 C1 C2 C3 -13.4(8) . . . . ?
C7 S1 C1 C2 -178.2(5) . . . . ?
C7 S1 C1 C6 1.1(4) . . . . ?
C7 N1 C6 C1 0.0(6) . . . . ?
C7 N1 C6 C5 177.3(4) . . . . ?
C7 N1 C8 C9 90.7(6) . . . . ?
C7 N1 C8 C13 -90.1(6) . . . . ?
C8 N1 C6 C1 176.2(4) . . . . ?
C8 N1 C6 C5 -6.5(7) . . . . ?
C8 N1 C7 S1 -175.5(3) . . . . ?
C8 N1 C7 S2 4.6(7) . . . . ?
C8 C9 C10 C11 1.2(8) . . . . ?
C9 C8 C13 C12 -1.4(8) . . . . ?
C9 C10 C11 C12 -0.4(10) . . . . ?
C10 C11 C12 C13 -1.3(10) . . . . ?
C11 C12 C13 C8 2.1(10) . . . . ?
C13 C8 C9 Br1 178.1(4) . . . . ?
C13 C8 C9 C10 -0.3(8) . . . . ?
Br2 C23 C24 C25 -178.2(5) . . . . ?
S3 C14 C20 N2 0.8(5) . . . . ?
S3 C14 C20 C19 -176.7(4) . . . . ?
N2 C22 C23 Br2 0.6(6) . . . . ?
N2 C22 C23 C24 -178.5(5) . . . . ?
N2 C22 C27 C26 177.3(5) . . . . ?
C14 S3 C21 S4 -179.9(4) . . . . ?
C14 S3 C21 N2 -0.1(4) . . . . ?
C15 C14 C20 N2 179.6(5) . . . . ?
C15 C14 C20 C19 2.1(8) . . . . ?
C18 C19 C20 N2 -177.6(6) . . . . ?
C18 C19 C20 C14 -0.3(9) . . . . ?
C20 N2 C21 S3 0.5(5) . . . . ?
C20 N2 C21 S4 -179.6(4) . . . . ?
C20 N2 C22 C23 -80.9(6) . . . . ?
C20 N2 C22 C27 101.1(5) . . . . ?
C21 S3 C14 C15 -179.2(5) . . . . ?
C21 S3 C14 C20 -0.4(4) . . . . ?
C21 N2 C20 C14 -0.9(6) . . . . ?
C21 N2 C20 C19 176.7(5) . . . . ?
C21 N2 C22 C23 98.2(5) . . . . ?
C21 N2 C22 C27 -79.9(6) . . . . ?
C22 N2 C20 C14 178.2(4) . . . . ?
C22 N2 C20 C19 -4.2(7) . . . . ?
C22 N2 C21 S3 -178.6(4) . . . . ?
C22 N2 C21 S4 1.2(7) . . . . ?
C22 C23 C24 C25 1.0(9) . . . . ?
C23 C22 C27 C26 -0.7(8) . . . . ?
C23 C24 C25 C26 -0.2(11) . . . . ?
C24 C25 C26 C27 -1.0(11) . . . . ?
C25 C26 C27 C22 1.5(10) . . . . ?
C27 C22 C23 Br2 178.7(4) . . . . ?
C27 C22 C23 C24 -0.5(7) . . . . ?

_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 1.919
_oxdiff_exptl_absorpt_empirical_full_min 0.516
