# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2190735'
loop_
_audit_author_name
_audit_author_address
'Ye Dong-Nai'
;Gannan Normal University
China
;
_audit_update_record             
;
2022-07-16 deposited with the CCDC.	2022-10-18 downloaded from the CCDC.
;
_audit_creation_date             2021-08-30
_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         'C13 H8 Br N S'
_chemical_formula_sum            'C13 H8 Br N S'
_chemical_formula_weight         290.17
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.6828(3)
_cell_length_b                   13.6599(7)
_cell_length_c                   19.3081(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1235.07(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1622
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.8740
_cell_measurement_theta_min      1.9070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.467
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.1073
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7528
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.106
_diffrn_reflns_theta_min         1.826
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.565
_reflns_Friedel_fraction_full    0.869
_reflns_Friedel_fraction_max     0.770
_reflns_number_gt                1911
_reflns_number_total             3205
_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 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_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    ?
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 
;
 Flack x determined using 424 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3205
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1685
_refine_ls_R_factor_gt           0.0982
_refine_ls_restrained_S_all      1.098
_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)+(0.0415P)²+3.4887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1681
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C7-C8
 1.32 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C11(H11), C2(H2), C8(H8), C3(H3), C10(H10), C9(H9), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.0262(3) 0.94991(8) 0.01862(6) 0.0576(4) Uani 1 1 d . . . . .
S1 S 1.2637(8) 0.6670(2) 0.34815(18) 0.0638(9) Uani 1 1 d . . . . .
C1 C 0.312(2) 0.9466(7) 0.1422(5) 0.045(3) Uani 1 1 d . . . . .
H1 H 0.245137 1.009979 0.148645 0.054 Uiso 1 1 calc R U . . .
C11 C 0.953(3) 0.8162(7) 0.2815(5) 0.046(3) Uani 1 1 d . . . . .
H11 H 0.908355 0.882591 0.282040 0.055 Uiso 1 1 calc R U . . .
N1 N 0.931(3) 0.5818(6) 0.2099(6) 0.077(4) Uani 1 1 d . . . . .
C2 C 0.503(3) 0.9055(6) 0.1895(5) 0.043(2) Uani 1 1 d . . . . .
H2 H 0.562305 0.942312 0.227389 0.052 Uiso 1 1 calc R U . . .
C8 C 1.275(2) 0.8534(7) 0.3822(5) 0.041(3) Uani 1 1 d D . . . .
H8 H 1.245002 0.920649 0.383743 0.049 Uiso 1 1 calc R U . . .
C3 C 0.506(3) 0.7564(6) 0.1244(5) 0.049(3) Uani 1 1 d . . . . .
H3 H 0.567400 0.692225 0.118047 0.059 Uiso 1 1 calc R U . . .
C4 C 0.608(2) 0.8095(6) 0.1811(5) 0.038(2) Uani 1 1 d . . . . .
C7 C 1.151(2) 0.7891(7) 0.3354(5) 0.042(3) Uani 1 1 d D . . . .
C12 C 0.815(2) 0.7667(6) 0.2301(5) 0.036(2) Uani 1 1 d . . . . .
C5 C 0.225(2) 0.8924(6) 0.0860(5) 0.039(3) Uani 1 1 d . . . . .
C10 C 1.473(3) 0.7031(8) 0.4160(5) 0.058(3) Uani 1 1 d . . . . .
H10 H 1.584218 0.660062 0.441778 0.069 Uiso 1 1 calc R U . . .
C13 C 0.881(2) 0.6618(8) 0.2202(5) 0.049(3) Uani 1 1 d . . . . .
C9 C 1.460(3) 0.7987(8) 0.4284(6) 0.065(3) Uani 1 1 d . . . . .
H9 H 1.562486 0.828290 0.463998 0.078 Uiso 1 1 calc R U . . .
C6 C 0.316(3) 0.7967(7) 0.0773(6) 0.051(3) Uani 1 1 d . . . . .
H6 H 0.250348 0.759833 0.040099 0.061 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 C5 1.922(10) . ?
S1 C7 1.766(10) . ?
S1 C10 1.709(12) . ?
C1 H1 0.9300 . ?
C1 C2 1.394(14) . ?
C1 C5 1.376(13) . ?
C11 H11 0.9300 . ?
C11 C7 1.444(14) . ?
C11 C12 1.363(14) . ?
N1 C13 1.136(12) . ?
C2 H2 0.9300 . ?
C2 C4 1.410(12) . ?
C8 H8 0.9300 . ?
C8 C7 1.387(9) . ?
C8 C9 1.450(15) . ?
C3 H3 0.9300 . ?
C3 C4 1.399(13) . ?
C3 C6 1.386(15) . ?
C4 C12 1.474(14) . ?
C12 C13 1.478(13) . ?
C5 C6 1.385(13) . ?
C10 H10 0.9300 . ?
C10 C9 1.329(14) . ?
C9 H9 0.9300 . ?
C6 H6 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
C10 S1 C7 90.3(5) . . ?
C2 C1 H1 120.3 . . ?
C5 C1 H1 120.3 . . ?
C5 C1 C2 119.4(9) . . ?
C7 C11 H11 112.7 . . ?
C12 C11 H11 112.7 . . ?
C12 C11 C7 134.6(9) . . ?
C1 C2 H2 119.2 . . ?
C1 C2 C4 121.5(9) . . ?
C4 C2 H2 119.2 . . ?
C7 C8 H8 125.5 . . ?
C7 C8 C9 108.9(9) . . ?
C9 C8 H8 125.5 . . ?
C4 C3 H3 119.1 . . ?
C6 C3 H3 119.1 . . ?
C6 C3 C4 121.8(9) . . ?
C2 C4 C12 121.6(9) . . ?
C3 C4 C2 117.0(10) . . ?
C3 C4 C12 121.4(8) . . ?
C11 C7 S1 122.3(7) . . ?
C8 C7 S1 112.5(8) . . ?
C8 C7 C11 125.2(9) . . ?
C11 C12 C4 125.5(9) . . ?
C11 C12 C13 118.4(10) . . ?
C4 C12 C13 116.0(9) . . ?
C1 C5 Br1 119.8(7) . . ?
C1 C5 C6 120.7(10) . . ?
C6 C5 Br1 119.5(8) . . ?
S1 C10 H10 123.3 . . ?
C9 C10 S1 113.3(10) . . ?
C9 C10 H10 123.3 . . ?
N1 C13 C12 177.4(12) . . ?
C8 C9 H9 122.5 . . ?
C10 C9 C8 115.0(11) . . ?
C10 C9 H9 122.5 . . ?
C3 C6 H6 120.2 . . ?
C5 C6 C3 119.6(10) . . ?
C5 C6 H6 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C5 C6 C3 177.4(8) . . . . ?
S1 C10 C9 C8 -0.4(15) . . . . ?
C1 C2 C4 C3 -1.8(15) . . . . ?
C1 C2 C4 C12 178.6(10) . . . . ?
C1 C5 C6 C3 -2.4(17) . . . . ?
C2 C1 C5 Br1 -177.6(8) . . . . ?
C2 C1 C5 C6 2.2(16) . . . . ?
C2 C4 C12 C11 -9.0(16) . . . . ?
C2 C4 C12 C13 172.9(10) . . . . ?
C3 C4 C12 C11 171.4(10) . . . . ?
C3 C4 C12 C13 -6.7(14) . . . . ?
C4 C3 C6 C5 0.4(17) . . . . ?
C7 S1 C10 C9 0.0(11) . . . . ?
C7 C11 C12 C4 177.7(10) . . . . ?
C7 C11 C12 C13 -4.3(18) . . . . ?
C7 C8 C9 C10 0.6(15) . . . . ?
C12 C11 C7 S1 -2.0(18) . . . . ?
C12 C11 C7 C8 177.8(12) . . . . ?
C5 C1 C2 C4 -0.1(16) . . . . ?
C10 S1 C7 C11 -179.8(9) . . . . ?
C10 S1 C7 C8 0.4(9) . . . . ?
C9 C8 C7 S1 -0.6(12) . . . . ?
C9 C8 C7 C11 179.6(10) . . . . ?
C6 C3 C4 C2 1.6(16) . . . . ?
C6 C3 C4 C12 -178.7(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
