# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_DBS-p7-rt
_database_code_depnum_ccdc_archive 'CCDC 2120853'
loop_
_audit_author_name
_audit_author_address
'Subhrajyoti Bhandary'
;Ghent University, Belgium
Belgium
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2021-10-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 S'
_chemical_formula_sum            'C12 H8 S'
_chemical_formula_weight         184.24
_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'
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                   8.7008(4)
_cell_length_b                   6.0100(3)
_cell_length_c                   17.1614(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.687(5)
_cell_angle_gamma                90
_cell_volume                     895.55(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3169
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4110
_cell_measurement_theta_min      5.1450
_shelx_estimated_absorpt_T_max   0.900
_shelx_estimated_absorpt_T_min   0.672
_exptl_absorpt_coefficient_mu    2.704
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
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    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8216
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.613
_diffrn_reflns_theta_min         5.165
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    1.00    --  -41.41 -38.00  30.00   99
  2  ω    -86.00  -6.00   1.00    1.00    --  -41.41 125.00 -60.00   80
  3  ω     27.00  97.00   1.00    1.00    --   41.41-125.00-120.00   70
  4  ω    103.00 178.00   1.00    5.00    --  106.28  77.00   0.00   75
  5  ω     24.00 106.00   1.00    5.00    --  106.28 -94.00  90.00   82
  6  ω     33.00 132.00   1.00    5.00    --  106.28 -45.00-150.00   99
  7  ω    103.00 178.00   1.00    5.00    --  106.28  77.00 -30.00   75
  8  ω     54.00 178.00   1.00    5.00    --  106.28  15.00  60.00  124
  9  ω     78.00 178.00   1.00    5.00    --  106.28  30.00 -60.00  100
 10  ω   -116.00 -17.00   1.00    1.00    --  -41.41 -38.00 120.00   99
 11  ω   -114.00 -13.00   1.00    1.00    --  -41.41 -57.00 -60.00  101
 12  ω     13.00 114.00   1.00    1.00    --   41.41  57.00-120.00  101
 13  ω     80.00 178.00   1.00    5.00    --  106.28  45.00-120.00   98
 14  ω     33.00 112.00   1.00    5.00    --  106.28-125.00  60.00   79
 15  ω     77.00 178.00   1.00    5.00    --  106.28  61.00 120.00  101
 16  ω     77.00 178.00   1.00    5.00    --  106.28  61.00  60.00  101
 17  ω     24.00 106.00   1.00    5.00    --  106.28 -94.00-180.00   82
 18  ω     80.00 178.00   1.00    5.00    --  106.28  45.00-180.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1697569000
_diffrn_orient_matrix_UB_12      0.0616407000
_diffrn_orient_matrix_UB_13      -0.0196926000
_diffrn_orient_matrix_UB_21      -0.0095009000
_diffrn_orient_matrix_UB_22      -0.1763768000
_diffrn_orient_matrix_UB_23      -0.0652804000
_diffrn_orient_matrix_UB_31      -0.0503977000
_diffrn_orient_matrix_UB_32      -0.1757543000
_diffrn_orient_matrix_UB_33      0.0586394000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                1452
_reflns_number_total             1802
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_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         0.217
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0034(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1802
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.087
_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)+(0.0402P)²+0.1962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.1035
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C3(H3), C2(H2), C11(H11), C4(H4), C9(H9), C10(H10)
;
_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
S1 S 0.51811(7) 0.16731(9) 0.36390(3) 0.0561(2) Uani 1 1 d . . . . .
C6 C 0.4354(2) 0.5404(3) 0.29414(10) 0.0415(4) Uani 1 1 d . . . . .
C7 C 0.3589(2) 0.5369(3) 0.36664(10) 0.0423(4) Uani 1 1 d . . . . .
C1 C 0.5265(2) 0.3499(3) 0.28520(11) 0.0454(4) Uani 1 1 d . . . . .
C5 C 0.4272(2) 0.6996(4) 0.23497(12) 0.0496(5) Uani 1 1 d . . . . .
H5 H 0.367267 0.826355 0.239781 0.060 Uiso 1 1 calc R U . . .
C12 C 0.3935(2) 0.3439(3) 0.40987(11) 0.0459(4) Uani 1 1 d . . . . .
C8 C 0.2580(2) 0.6920(4) 0.39552(12) 0.0506(5) Uani 1 1 d . . . . .
H8 H 0.232477 0.819963 0.367073 0.061 Uiso 1 1 calc R U . . .
C3 C 0.5984(2) 0.4799(4) 0.16177(12) 0.0565(5) Uani 1 1 d . . . . .
H3 H 0.652453 0.461448 0.117184 0.068 Uiso 1 1 calc R U . . .
C2 C 0.6093(2) 0.3199(4) 0.21909(12) 0.0531(5) Uani 1 1 d . . . . .
H2 H 0.670363 0.194455 0.213888 0.064 Uiso 1 1 calc R U . . .
C11 C 0.3316(3) 0.3063(4) 0.48176(12) 0.0571(5) Uani 1 1 d . . . . .
H11 H 0.356125 0.178488 0.510461 0.069 Uiso 1 1 calc R U . . .
C4 C 0.5082(3) 0.6689(4) 0.16914(12) 0.0544(5) Uani 1 1 d . . . . .
H4 H 0.502442 0.775050 0.129616 0.065 Uiso 1 1 calc R U . . .
C9 C 0.1963(3) 0.6555(4) 0.46621(13) 0.0590(5) Uani 1 1 d . . . . .
H9 H 0.129493 0.759539 0.485627 0.071 Uiso 1 1 calc R U . . .
C10 C 0.2335(3) 0.4631(4) 0.50897(13) 0.0620(6) Uani 1 1 d . . . . .
H10 H 0.191018 0.440712 0.556722 0.074 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
S1 C1 1.746(2) . ?
S1 C12 1.742(2) . ?
C6 C7 1.449(3) . ?
C6 C1 1.406(3) . ?
C6 C5 1.394(3) . ?
C7 C12 1.399(3) . ?
C7 C8 1.394(3) . ?
C1 C2 1.394(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.382(3) . ?
C12 C11 1.396(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.375(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.375(3) . ?
C3 C4 1.391(3) . ?
C2 H2 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.373(3) . ?
C4 H4 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.396(4) . ?
C10 H10 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
C12 S1 C1 91.46(10) . . ?
C1 C6 C7 112.03(17) . . ?
C5 C6 C7 129.13(18) . . ?
C5 C6 C1 118.83(18) . . ?
C12 C7 C6 111.88(17) . . ?
C8 C7 C6 129.09(18) . . ?
C8 C7 C12 119.01(18) . . ?
C6 C1 S1 112.05(14) . . ?
C2 C1 S1 126.71(17) . . ?
C2 C1 C6 121.23(19) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 120.0 . . ?
C7 C12 S1 112.57(14) . . ?
C11 C12 S1 126.05(17) . . ?
C11 C12 C7 121.39(19) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.5(2) . . ?
C3 C2 H2 120.8 . . ?
C12 C11 H11 120.9 . . ?
C10 C11 C12 118.2(2) . . ?
C10 C11 H11 120.9 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 121.2(2) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?

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 C1 C2 C3 178.18(17) . . . . ?
S1 C12 C11 C10 -179.31(18) . . . . ?
C6 C7 C12 S1 0.2(2) . . . . ?
C6 C7 C12 C11 -179.87(19) . . . . ?
C6 C7 C8 C9 179.4(2) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C7 C6 C1 S1 0.4(2) . . . . ?
C7 C6 C1 C2 179.62(17) . . . . ?
C7 C6 C5 C4 -178.85(19) . . . . ?
C7 C12 C11 C10 0.8(3) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C1 S1 C12 C7 0.00(16) . . . . ?
C1 S1 C12 C11 -179.9(2) . . . . ?
C1 C6 C7 C12 -0.4(2) . . . . ?
C1 C6 C7 C8 -178.79(19) . . . . ?
C1 C6 C5 C4 -0.2(3) . . . . ?
C5 C6 C7 C12 178.26(19) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C5 C6 C1 S1 -178.41(15) . . . . ?
C5 C6 C1 C2 0.8(3) . . . . ?
C12 S1 C1 C6 -0.25(16) . . . . ?
C12 S1 C1 C2 -179.38(19) . . . . ?
C12 C7 C8 C9 1.1(3) . . . . ?
C12 C11 C10 C9 -0.1(4) . . . . ?
C8 C7 C12 S1 178.78(15) . . . . ?
C8 C7 C12 C11 -1.3(3) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C4 C3 C2 C1 0.4(3) . . . . ?

_olex2_date_sample_data_collection 2021-09-12
_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 1.491
_oxdiff_exptl_absorpt_empirical_full_min 0.785
####################################################################### 
# 
# 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_DBS-Br-rt
_database_code_depnum_ccdc_archive 'CCDC 2120854'
loop_
_audit_author_name
_audit_author_address
'Subhrajyoti Bhandary'
;Ghent University, Belgium
Belgium
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2021-10-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H7 Br S'
_chemical_formula_sum            'C12 H7 Br S'
_chemical_formula_weight         263.15
_chemical_absolute_configuration ?
_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'
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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.9779(2)
_cell_length_b                   12.1736(4)
_cell_length_c                   20.4259(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     989.13(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3832
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6640
_cell_measurement_theta_min      4.2040
_shelx_estimated_absorpt_T_max   0.813
_shelx_estimated_absorpt_T_min   0.356
_exptl_absorpt_coefficient_mu    7.220
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
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    1.767
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8723
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.827
_diffrn_reflns_theta_min         4.228
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -17.00   1.00    1.00    --  -41.16 -38.00 -30.00   98
  2  ω    -87.00  -6.00   1.00    1.00    --  -41.16 125.00 150.00   81
  3  ω      6.00  82.00   1.00    1.00    --   41.16 -99.00  30.00   76
  4  ω      6.00  82.00   1.00    1.00    --   41.16 -99.00-150.00   76
  5  ω    103.00 178.00   1.00    3.00    --  106.28  77.00  90.00   75
  6  ω     34.00 135.00   1.00    3.00    --  106.28 -61.00 150.00  101
  7  ω     80.00 178.00   1.00    3.00    --  106.28  45.00   0.00   98
  8  ω    103.00 178.00   1.00    3.00    --  106.28  77.00 -60.00   75
  9  ω     97.00 178.00   1.00    3.00    --  106.28 125.00 -90.00   81
 10  ω   -114.00 -13.00   1.00    1.00    --  -41.16 -57.00-180.00  101
 11  ω   -114.00 -13.00   1.00    1.00    --  -41.16 -57.00  90.00  101
 12  ω     78.00 178.00   1.00    3.00    --  106.28  30.00-120.00  100
 13  ω     33.00 112.00   1.00    3.00    --  106.28-125.00  90.00   79
 14  ω     80.00 178.00   1.00    3.00    --  106.28  45.00  60.00   98
 15  ω    103.00 178.00   1.00    3.00    --  106.28  77.00 150.00   75
 16  ω   -115.00 -17.00   1.00    1.00    --  -41.16 -38.00-120.00   98
 17  ω     13.00 114.00   1.00    1.00    --   41.16  57.00 150.00  101
 18  ω     80.00 178.00   1.00    3.00    --  106.28  45.00 -90.00   98
 19  ω     77.00 119.00   1.00    3.00    --  106.28  61.00 120.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0447625000
_diffrn_orient_matrix_UB_12      -0.0495937000
_diffrn_orient_matrix_UB_13      0.0688614000
_diffrn_orient_matrix_UB_21      0.2928967000
_diffrn_orient_matrix_UB_22      0.0709876000
_diffrn_orient_matrix_UB_23      0.0254032000
_diffrn_orient_matrix_UB_31      -0.2492665000
_diffrn_orient_matrix_UB_32      0.0922768000
_diffrn_orient_matrix_UB_33      0.0174294000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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         0.626
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                1681
_reflns_number_total             1953
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.042
_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)+(0.0394P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0802
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C2(H2), C9(H9), C10(H10), C3(H3), 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 0.56725(17) 0.54164(5) 0.54641(3) 0.0601(2) Uani 1 1 d . . . . .
S1 S 0.0051(4) 0.86374(9) 0.76671(7) 0.0510(3) Uani 1 1 d . . . . .
C5 C 0.4222(14) 0.6132(4) 0.6755(2) 0.0422(10) Uani 1 1 d . . . . .
H5 H 0.517596 0.546792 0.688217 0.051 Uiso 1 1 calc R U . . .
C4 C 0.4072(14) 0.6410(4) 0.6106(2) 0.0467(11) Uani 1 1 d . . . . .
C6 C 0.2941(13) 0.6847(4) 0.7221(2) 0.0400(11) Uani 1 1 d . . . . .
C7 C 0.2802(12) 0.6720(4) 0.7926(2) 0.0405(11) Uani 1 1 d . . . . .
C8 C 0.3911(14) 0.5857(4) 0.8313(3) 0.0488(12) Uani 1 1 d . . . . .
H8 H 0.493984 0.525074 0.812146 0.059 Uiso 1 1 calc R U . . .
C1 C 0.1556(12) 0.7854(4) 0.7016(2) 0.0421(11) Uani 1 1 d . . . . .
C2 C 0.1434(14) 0.8140(4) 0.6353(3) 0.0496(13) Uani 1 1 d . . . . .
H2 H 0.050688 0.880542 0.622190 0.060 Uiso 1 1 calc R U . . .
C9 C 0.3484(15) 0.5900(4) 0.8982(3) 0.0546(14) Uani 1 1 d . . . . .
H9 H 0.422692 0.531779 0.923889 0.065 Uiso 1 1 calc R U . . .
C12 C 0.1269(14) 0.7633(4) 0.8232(3) 0.0473(12) Uani 1 1 d . . . . .
C10 C 0.1956(16) 0.6801(5) 0.9280(3) 0.0596(15) Uani 1 1 d . . . . .
H10 H 0.169037 0.681745 0.973221 0.072 Uiso 1 1 calc R U . . .
C3 C 0.2716(15) 0.7416(4) 0.5899(3) 0.0509(13) Uani 1 1 d . . . . .
H3 H 0.268214 0.759310 0.545604 0.061 Uiso 1 1 calc R U . . .
C11 C 0.0836(17) 0.7670(4) 0.8903(3) 0.0561(13) Uani 1 1 d . . . . .
H11 H -0.019638 0.827163 0.909885 0.067 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 C4 1.895(5) . ?
S1 C1 1.743(5) . ?
S1 C12 1.749(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.369(7) . ?
C5 C6 1.387(7) . ?
C4 C3 1.403(7) . ?
C6 C7 1.449(7) . ?
C6 C1 1.408(6) . ?
C7 C8 1.388(7) . ?
C7 C12 1.413(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(8) . ?
C1 C2 1.398(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.394(8) . ?
C12 C11 1.384(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(8) . ?
C3 H3 0.9300 . ?
C11 H11 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
C1 S1 C12 91.5(2) . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.5(5) . . ?
C6 C5 H5 120.2 . . ?
C5 C4 Br1 119.8(4) . . ?
C5 C4 C3 121.7(5) . . ?
C3 C4 Br1 118.5(4) . . ?
C5 C6 C7 129.0(4) . . ?
C5 C6 C1 119.1(4) . . ?
C1 C6 C7 111.9(4) . . ?
C8 C7 C6 129.4(5) . . ?
C8 C7 C12 118.7(5) . . ?
C12 C7 C6 111.9(4) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.8(5) . . ?
C9 C8 H8 120.1 . . ?
C6 C1 S1 112.5(4) . . ?
C2 C1 S1 126.2(4) . . ?
C2 C1 C6 121.2(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.7(5) . . ?
C3 C2 H2 120.7 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.1(5) . . ?
C10 C9 H9 119.4 . . ?
C7 C12 S1 112.2(4) . . ?
C11 C12 S1 126.6(4) . . ?
C11 C12 C7 121.2(5) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(5) . . ?
C11 C10 H10 120.0 . . ?
C4 C3 H3 120.1 . . ?
C2 C3 C4 119.8(5) . . ?
C2 C3 H3 120.1 . . ?
C12 C11 H11 120.4 . . ?
C10 C11 C12 119.1(5) . . ?
C10 C11 H11 120.4 . . ?

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
Br1 C4 C3 C2 177.9(4) . . . . ?
S1 C1 C2 C3 -179.3(4) . . . . ?
S1 C12 C11 C10 -179.9(5) . . . . ?
C5 C4 C3 C2 -1.3(8) . . . . ?
C5 C6 C7 C8 0.0(9) . . . . ?
C5 C6 C7 C12 -179.5(5) . . . . ?
C5 C6 C1 S1 179.6(4) . . . . ?
C5 C6 C1 C2 0.4(8) . . . . ?
C4 C5 C6 C7 179.4(5) . . . . ?
C4 C5 C6 C1 -0.9(8) . . . . ?
C6 C5 C4 Br1 -177.8(4) . . . . ?
C6 C5 C4 C3 1.4(8) . . . . ?
C6 C7 C8 C9 -179.1(5) . . . . ?
C6 C7 C12 S1 -0.6(6) . . . . ?
C6 C7 C12 C11 178.9(5) . . . . ?
C6 C1 C2 C3 -0.3(8) . . . . ?
C7 C6 C1 S1 -0.7(6) . . . . ?
C7 C6 C1 C2 -179.9(5) . . . . ?
C7 C8 C9 C10 -0.2(9) . . . . ?
C7 C12 C11 C10 0.6(9) . . . . ?
C8 C7 C12 S1 179.8(4) . . . . ?
C8 C7 C12 C11 -0.7(8) . . . . ?
C8 C9 C10 C11 0.1(9) . . . . ?
C1 S1 C12 C7 0.2(4) . . . . ?
C1 S1 C12 C11 -179.3(6) . . . . ?
C1 C6 C7 C8 -179.7(5) . . . . ?
C1 C6 C7 C12 0.8(6) . . . . ?
C1 C2 C3 C4 0.7(8) . . . . ?
C9 C10 C11 C12 -0.3(9) . . . . ?
C12 S1 C1 C6 0.3(4) . . . . ?
C12 S1 C1 C2 179.5(5) . . . . ?
C12 C7 C8 C9 0.4(8) . . . . ?

_olex2_date_sample_data_collection 2021-09-13
_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 2.306
_oxdiff_exptl_absorpt_empirical_full_min 0.581
####################################################################### 
# 
# 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_dbs-nat-bent
_database_code_depnum_ccdc_archive 'CCDC 2166318'
loop_
_audit_author_name
_audit_author_address
'Subhrajyoti Bhandary'
;Ghent University, Belgium
Belgium
;
_audit_update_record             
;
2022-04-13 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2022-04-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 S'
_chemical_formula_sum            'C12 H8 S'
_chemical_formula_weight         184.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H8 S1'
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'
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                   8.7011(5)
_cell_length_b                   6.0075(3)
_cell_length_c                   17.1510(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.695(5)
_cell_angle_gamma                90
_cell_volume                     894.65(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3938
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      73.1990
_cell_measurement_theta_min      5.1140
_shelx_estimated_absorpt_T_max   0.899
_shelx_estimated_absorpt_T_min   0.497
_exptl_absorpt_coefficient_mu    2.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1776
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8404
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.012
_diffrn_reflns_theta_max         67.012
_diffrn_reflns_theta_min         5.169
_diffrn_ambient_temperature      290(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  32.00   0.75    8.00    --  -41.41  57.00 120.00  136
  2  ω    -86.00  -6.50   0.75    8.00    --  -41.41 125.00-180.00  106
  3  ω   -114.00 -13.50   0.75    8.00    --  -41.41 -57.00 -30.00  134
  4  ω    -33.00  66.00   0.75    8.00    --   41.41 -38.00-180.00  132
  5  ω     27.00  96.00   0.75    8.00    --   41.41-125.00-180.00   92
  6  ω     24.00 105.00   0.75   22.00    --  106.28 -94.00-180.00  108
  7  ω     33.00 132.00   0.75   22.00    --  106.28 -45.00 150.00  132
  8  ω     97.00 178.00   0.75   22.00    --  106.28 125.00  60.00  108
  9  ω     30.00 135.00   0.75   22.00    --  106.28 -30.00   0.00  140
 10  ω     33.00 111.00   0.75   22.00    --  106.28-125.00  60.00  104
 11  ω     77.00 177.50   0.75   22.00    --  106.28  61.00-120.00  134
 12  ω    103.00 178.00   0.75   22.00    --  106.28  77.00 120.00  100
 13  ω     33.00 111.00   0.75   22.00    --  106.28-125.00   0.00  104
 14  ω     33.00 111.00   0.75   22.00    --  106.28-125.00-180.00  104
 15  ω     24.00 105.00   0.75   22.00    --  106.28 -95.00-106.00  108
 16  ω     80.00 177.50   0.75   22.00    --  106.28  45.00-180.00  130
 17  ω     30.00 138.00   0.75   22.00    --  106.28 -77.00  30.00  144
 18  ω     80.00 177.50   0.75   22.00    --  106.28  45.00   0.00  130
 19  ω   -114.00 -13.50   0.75    8.00    --  -41.41 -57.00-150.00  134
 20  ω    -86.00  -6.50   0.75    8.00    --  -41.41 125.00 -90.00  106
 21  ω     13.00 113.50   0.75    8.00    --   41.41  57.00 150.00  134
 22  ω     13.00 113.50   0.75    8.00    --   41.41  57.00  60.00  134
 23  ω     13.00 113.50   0.75    8.00    --   41.41  57.00 -30.00  134
 24  ω     77.00 177.50   0.75   22.00    --  106.28  61.00 -60.00  134
 25  ω     77.00 177.50   0.75   22.00    --  106.28  61.00  90.00  134
 26  ω     78.00 177.00   0.75   22.00    --  106.28  30.00  90.00  132
 27  ω     77.00 177.50   0.75   22.00    --  106.28  61.00 -90.00  134
 28  ω     77.00 177.50   0.75   22.00    --  106.28  61.00-150.00  134
 29  ω     77.00 177.50   0.75   22.00    --  106.28  61.00  30.00  134
 30  ω     77.00 177.50   0.75   22.00    --  106.28  61.00 -30.00  134
 31  ω     77.00 177.50   0.75   22.00    --  106.28  61.00 150.00  134
 32  ω     77.00 177.50   0.75   22.00    --  106.28  61.00 120.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1540538000
_diffrn_orient_matrix_UB_12      -0.0586381000
_diffrn_orient_matrix_UB_13      -0.0344895000
_diffrn_orient_matrix_UB_21      -0.0866358000
_diffrn_orient_matrix_UB_22      -0.1439745000
_diffrn_orient_matrix_UB_23      -0.0629087000
_diffrn_orient_matrix_UB_31      -0.0166437000
_diffrn_orient_matrix_UB_32      0.2039306000
_diffrn_orient_matrix_UB_33      -0.0542834000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                1141
_reflns_number_total             1591
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.881
_refine_diff_density_min         -1.373
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.541
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1591
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1666
_refine_ls_R_factor_gt           0.1433
_refine_ls_restrained_S_all      1.541
_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)+(0.2500P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4136
_refine_ls_wR_factor_ref         0.4727
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C11(H11), C10(H10), C8(H8), C4(H4), C9(H9), C2(H2)
;
_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
S1 S 0.5183(2) 0.1672(2) 0.36357(10) 0.0740(10) Uani 1 1 d . . . . .
C1 C 0.5265(8) 0.3516(8) 0.2854(4) 0.0599(17) Uani 1 1 d . . . . .
C6 C 0.4353(8) 0.5404(9) 0.2942(4) 0.0623(18) Uani 1 1 d . . . . .
C12 C 0.3922(8) 0.3443(8) 0.4113(4) 0.0624(18) Uani 1 1 d . . . . .
C7 C 0.3591(7) 0.5375(9) 0.3667(4) 0.0631(18) Uani 1 1 d . . . . .
C5 C 0.4276(9) 0.6994(10) 0.2355(4) 0.0679(19) Uani 1 1 d . . . . .
H5 H 0.368793 0.827101 0.240790 0.081 Uiso 1 1 calc R U . . .
C3 C 0.5966(8) 0.4806(12) 0.1625(4) 0.075(2) Uani 1 1 d . . . . .
H3 H 0.650957 0.461690 0.118046 0.090 Uiso 1 1 calc R U . . .
C11 C 0.3317(10) 0.3090(11) 0.4825(5) 0.078(2) Uani 1 1 d . . . . .
H11 H 0.357450 0.182463 0.511739 0.094 Uiso 1 1 calc R U . . .
C10 C 0.2332(10) 0.4635(12) 0.5092(4) 0.078(2) Uani 1 1 d . . . . .
H10 H 0.189402 0.439402 0.556545 0.094 Uiso 1 1 calc R U . . .
C8 C 0.2570(9) 0.6926(10) 0.3958(5) 0.075(2) Uani 1 1 d . . . . .
H8 H 0.229798 0.819596 0.367164 0.090 Uiso 1 1 calc R U . . .
C4 C 0.5068(10) 0.6686(10) 0.1695(5) 0.080(2) Uani 1 1 d . . . . .
H4 H 0.499975 0.773924 0.129705 0.095 Uiso 1 1 calc R U . . .
C9 C 0.1969(10) 0.6556(11) 0.4675(5) 0.080(2) Uani 1 1 d . . . . .
H9 H 0.131763 0.760607 0.487673 0.096 Uiso 1 1 calc R U . . .
C2 C 0.6071(10) 0.3207(10) 0.2203(5) 0.076(2) Uani 1 1 d . . . . .
H2 H 0.667665 0.194617 0.215153 0.092 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
S1 C1 1.744(6) . ?
S1 C12 1.767(7) . ?
C1 C6 1.398(8) . ?
C1 C2 1.370(11) . ?
C6 C7 1.446(10) . ?
C6 C5 1.386(9) . ?
C12 C7 1.409(8) . ?
C12 C11 1.378(11) . ?
C7 C8 1.401(10) . ?
C5 H5 0.9300 . ?
C5 C4 1.375(12) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(10) . ?
C3 C2 1.379(10) . ?
C11 H11 0.9300 . ?
C11 C10 1.362(11) . ?
C10 H10 0.9300 . ?
C10 C9 1.384(10) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(12) . ?
C4 H4 0.9300 . ?
C9 H9 0.9300 . ?
C2 H2 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
C1 S1 C12 91.7(3) . . ?
C6 C1 S1 112.4(5) . . ?
C2 C1 S1 126.1(5) . . ?
C2 C1 C6 121.5(6) . . ?
C1 C6 C7 112.2(5) . . ?
C5 C6 C1 118.8(7) . . ?
C5 C6 C7 129.0(6) . . ?
C7 C12 S1 110.9(6) . . ?
C11 C12 S1 127.0(5) . . ?
C11 C12 C7 122.1(6) . . ?
C12 C7 C6 112.8(6) . . ?
C8 C7 C6 129.4(5) . . ?
C8 C7 C12 117.8(7) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.1(6) . . ?
C4 C5 H5 119.9 . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(8) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 C12 118.5(6) . . ?
C10 C11 H11 120.7 . . ?
C11 C10 H10 119.3 . . ?
C11 C10 C9 121.4(8) . . ?
C9 C10 H10 119.3 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.6(6) . . ?
C9 C8 H8 120.2 . . ?
C5 C4 C3 119.8(6) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C10 C9 H9 119.8 . . ?
C8 C9 C10 120.4(8) . . ?
C8 C9 H9 119.8 . . ?
C1 C2 C3 118.6(6) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?

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
S1 C1 C6 C7 1.1(6) . . . . ?
S1 C1 C6 C5 -178.5(4) . . . . ?
S1 C1 C2 C3 177.7(5) . . . . ?
S1 C12 C7 C6 0.3(6) . . . . ?
S1 C12 C7 C8 178.4(4) . . . . ?
S1 C12 C11 C10 -178.7(5) . . . . ?
C1 S1 C12 C7 0.3(5) . . . . ?
C1 S1 C12 C11 -179.2(6) . . . . ?
C1 C6 C7 C12 -0.9(7) . . . . ?
C1 C6 C7 C8 -178.7(6) . . . . ?
C1 C6 C5 C4 1.1(9) . . . . ?
C6 C1 C2 C3 -0.1(10) . . . . ?
C6 C7 C8 C9 179.8(6) . . . . ?
C6 C5 C4 C3 -1.3(10) . . . . ?
C12 S1 C1 C6 -0.8(5) . . . . ?
C12 S1 C1 C2 -178.8(6) . . . . ?
C12 C7 C8 C9 2.2(9) . . . . ?
C12 C11 C10 C9 -1.8(11) . . . . ?
C7 C6 C5 C4 -178.5(6) . . . . ?
C7 C12 C11 C10 2.0(10) . . . . ?
C7 C8 C9 C10 -2.1(10) . . . . ?
C5 C6 C7 C12 178.6(6) . . . . ?
C5 C6 C7 C8 0.9(10) . . . . ?
C11 C12 C7 C6 179.8(6) . . . . ?
C11 C12 C7 C8 -2.2(9) . . . . ?
C11 C10 C9 C8 1.9(11) . . . . ?
C4 C3 C2 C1 -0.1(11) . . . . ?
C2 C1 C6 C7 179.3(6) . . . . ?
C2 C1 C6 C5 -0.3(9) . . . . ?
C2 C3 C4 C5 0.8(10) . . . . ?

_olex2_date_sample_data_collection 2022-02-25
_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 2.430
_oxdiff_exptl_absorpt_empirical_full_min 0.221
####################################################################### 
# 
# 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_dbs-br-nat-bent
_database_code_depnum_ccdc_archive 'CCDC 2166317'
loop_
_audit_author_name
_audit_author_address
'Subhrajyoti Bhandary'
;Ghent University, Belgium
Belgium
;
_audit_update_record             
;
2022-04-13 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2022-03-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H7 Br S'
_chemical_formula_sum            'C12 H7 Br S'
_chemical_formula_weight         263.15
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 Br1 S1 H8'
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'
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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.9868(3)
_cell_length_b                   12.1976(7)
_cell_length_c                   20.4470(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     994.33(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1540
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      69.1530
_cell_measurement_theta_min      4.1690
_shelx_estimated_absorpt_T_max   0.762
_shelx_estimated_absorpt_T_min   0.267
_exptl_absorpt_coefficient_mu    7.182
_exptl_absorpt_correction_T_max  0.05805
_exptl_absorpt_correction_T_min  0.00429
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Spherical absorption correction
using equivalent radius and absorption coefficient.
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    1.758
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_size_rad          0.400
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4820
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.054
_diffrn_reflns_theta_min         4.220
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      290(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_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      6.00  82.00   1.00    2.00    --   41.16 -99.00 -90.00   76
  2  ω    -47.00 129.00   1.00    2.00    --   41.16   0.00  90.00  176
  3  ω     34.00 135.00   1.00    6.00    --  106.28 -61.00 -60.00  101
  4  ω    103.00 178.00   1.00    6.00    --  106.28  77.00  90.00   75
  5  ω     97.00 178.00   1.00    6.00    --  106.28 125.00   0.00   81
  6  ω     30.00 139.00   1.00    6.00    --  106.28 -77.00-150.00  109
  7  ω    103.00 178.00   1.00    6.00    --  106.28  77.00 -30.00   75
  8  ω   -114.00 -13.00   1.00    2.00    --  -41.16 -57.00 -90.00  101
  9  ω   -114.00 -13.00   1.00    2.00    --  -41.16 -57.00-180.00  101
 10  ω     77.00 128.00   1.00    6.00    --  106.28  61.00 -90.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1787730000
_diffrn_orient_matrix_UB_12      0.0563873000
_diffrn_orient_matrix_UB_13      0.0576504000
_diffrn_orient_matrix_UB_21      -0.3006895000
_diffrn_orient_matrix_UB_22      0.0257531000
_diffrn_orient_matrix_UB_23      -0.0447299000
_diffrn_orient_matrix_UB_31      -0.1632410000
_diffrn_orient_matrix_UB_32      -0.1100954000
_diffrn_orient_matrix_UB_33      0.0189606000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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         0.527
_reflns_Friedel_fraction_full    0.871
_reflns_Friedel_fraction_max     0.807
_reflns_number_gt                1288
_reflns_number_total             1831
_reflns_odcompleteness_completeness 97.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         1.590
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.204
_refine_ls_abs_structure_details 
;
 Flack x determined using 286 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1831
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.1028
_refine_ls_restrained_S_all      1.204
_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)+(0.1989P)²+0.5506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2940
_refine_ls_wR_factor_ref         0.3580
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C2(H2), C3(H3), 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 0.4339(7) 0.4583(2) 0.54627(11) 0.1135(10) Uani 1 1 d . . . . .
S1 S 0.9939(15) 0.1363(4) 0.7665(3) 0.1030(14) Uani 1 1 d . . . . .
C5 C 0.574(5) 0.3874(16) 0.6753(8) 0.094(4) Uani 1 1 d . . . . .
H5 H 0.478411 0.453687 0.687805 0.112 Uiso 1 1 calc R U . . .
C6 C 0.708(5) 0.3144(14) 0.7225(9) 0.087(4) Uani 1 1 d . . . . .
C1 C 0.842(5) 0.2157(14) 0.7011(10) 0.092(5) Uani 1 1 d . . . . .
C8 C 0.608(6) 0.4141(17) 0.8310(10) 0.104(5) Uani 1 1 d . . . . .
H8 H 0.505516 0.474414 0.811643 0.124 Uiso 1 1 calc R U . . .
C7 C 0.715(5) 0.3279(13) 0.7921(10) 0.091(5) Uani 1 1 d . . . . .
C9 C 0.651(5) 0.4121(16) 0.8985(11) 0.099(5) Uani 1 1 d . . . . .
H9 H 0.580604 0.470381 0.924431 0.119 Uiso 1 1 calc R U . . .
C2 C 0.864(6) 0.1873(17) 0.6353(11) 0.104(5) Uani 1 1 d . . . . .
H2 H 0.962640 0.121813 0.622251 0.124 Uiso 1 1 calc R U . . .
C12 C 0.878(5) 0.2370(18) 0.8227(10) 0.100(5) Uani 1 1 d . . . . .
C4 C 0.591(5) 0.3578(16) 0.6103(9) 0.096(5) Uani 1 1 d . . . . .
C3 C 0.734(6) 0.2596(17) 0.5902(10) 0.102(5) Uani 1 1 d . . . . .
H3 H 0.742189 0.242514 0.545918 0.122 Uiso 1 1 calc R U . . .
C10 C 0.803(6) 0.3208(18) 0.9262(10) 0.106(6) Uani 1 1 d . . . . .
H10 H 0.832347 0.318824 0.971324 0.128 Uiso 1 1 calc R U . . .
C11 C 0.912(7) 0.2335(18) 0.8898(10) 0.105(6) Uani 1 1 d . . . . .
H11 H 1.006706 0.172721 0.910012 0.127 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 C4 1.900(19) . ?
S1 C1 1.76(2) . ?
S1 C12 1.74(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.42(3) . ?
C5 C4 1.38(3) . ?
C6 C1 1.39(2) . ?
C6 C7 1.43(3) . ?
C1 C2 1.39(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.39(3) . ?
C8 C9 1.39(3) . ?
C7 C12 1.43(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.39(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.38(3) . ?
C12 C11 1.38(3) . ?
C4 C3 1.39(3) . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.37(3) . ?
C11 H11 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
C12 S1 C1 91.3(10) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.2(19) . . ?
C5 C6 C7 127.7(17) . . ?
C1 C6 C5 118.4(17) . . ?
C1 C6 C7 113.9(17) . . ?
C6 C1 S1 111.8(15) . . ?
C6 C1 C2 122.9(18) . . ?
C2 C1 S1 125.2(14) . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121(2) . . ?
C9 C8 H8 119.4 . . ?
C8 C7 C6 130.7(18) . . ?
C8 C7 C12 118.5(19) . . ?
C12 C7 C6 110.7(16) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 C8 118(2) . . ?
C10 C9 H9 120.9 . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.7(19) . . ?
C3 C2 H2 121.2 . . ?
C7 C12 S1 112.2(15) . . ?
C11 C12 S1 127.5(18) . . ?
C11 C12 C7 120(2) . . ?
C5 C4 Br1 118.6(15) . . ?
C5 C4 C3 122.1(19) . . ?
C3 C4 Br1 119.2(15) . . ?
C2 C3 C4 120.6(19) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.7(19) . . ?
C11 C10 H10 118.7 . . ?
C12 C11 H11 120.4 . . ?
C10 C11 C12 119(2) . . ?
C10 C11 H11 120.4 . . ?

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
Br1 C4 C3 C2 177.0(17) . . . . ?
S1 C1 C2 C3 -179.4(16) . . . . ?
S1 C12 C11 C10 -179.4(18) . . . . ?
C5 C6 C1 S1 -180.0(14) . . . . ?
C5 C6 C1 C2 3(3) . . . . ?
C5 C6 C7 C8 -2(4) . . . . ?
C5 C6 C7 C12 -178.6(19) . . . . ?
C5 C4 C3 C2 0(3) . . . . ?
C6 C5 C4 Br1 -176.8(14) . . . . ?
C6 C5 C4 C3 0(3) . . . . ?
C6 C1 C2 C3 -2(3) . . . . ?
C6 C7 C12 S1 -3(2) . . . . ?
C6 C7 C12 C11 -180(2) . . . . ?
C1 S1 C12 C7 2.2(16) . . . . ?
C1 S1 C12 C11 178(2) . . . . ?
C1 C6 C7 C8 179(2) . . . . ?
C1 C6 C7 C12 3(3) . . . . ?
C1 C2 C3 C4 1(3) . . . . ?
C8 C7 C12 S1 179.8(16) . . . . ?
C8 C7 C12 C11 3(3) . . . . ?
C8 C9 C10 C11 0(3) . . . . ?
C7 C6 C1 S1 -2(2) . . . . ?
C7 C6 C1 C2 -178.9(19) . . . . ?
C7 C8 C9 C10 0(3) . . . . ?
C7 C12 C11 C10 -4(3) . . . . ?
C9 C8 C7 C6 -177(2) . . . . ?
C9 C8 C7 C12 -1(3) . . . . ?
C9 C10 C11 C12 2(4) . . . . ?
C12 S1 C1 C6 -0.4(16) . . . . ?
C12 S1 C1 C2 176.9(19) . . . . ?
C4 C5 C6 C1 -1(3) . . . . ?
C4 C5 C6 C7 -179(2) . . . . ?

_olex2_date_sample_data_collection 2022-03-03
_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 9.058
_oxdiff_exptl_absorpt_empirical_full_min 0.407
