# 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_111
_database_code_depnum_ccdc_archive 'CCDC 2162074'
loop_
_audit_author_name
_audit_author_address
'Shi-Hui SHI'
;Yan an University
China
;
_audit_update_record             
;
2022-03-25 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;
_audit_creation_date             2021-10-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Br2 N2 O3 S'
_chemical_formula_sum            'C15 H10 Br2 N2 O3 S'
_chemical_formula_weight         458.13
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2412(7)
_cell_length_b                   8.1065(9)
_cell_length_c                   16.0274(18)
_cell_angle_alpha                88.586(4)
_cell_angle_beta                 79.678(3)
_cell_angle_gamma                84.807(4)
_cell_volume                     794.47(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8951
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.492
_cell_measurement_theta_min      3.331
_shelx_estimated_absorpt_T_max   0.405
_shelx_estimated_absorpt_T_min   0.254
_exptl_absorpt_coefficient_mu    5.248
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0883 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.7434.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16685
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         3.331
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2989
_reflns_number_total             3649
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.899
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3649
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+0.3873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0779
_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:
 C3(H3), C6(H6), C4(H4), C15(H15), C9(H9), C12(H12), C7(H7)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.32806(5) 0.64363(4) 1.11799(2) 0.05517(10) Uani 1 1 d . . . . .
Br2 Br -0.14312(5) 0.86274(4) 1.19776(2) 0.05889(11) Uani 1 1 d . . . . .
S1 S 0.14230(10) 0.70630(7) 0.62838(4) 0.03916(15) Uani 1 1 d . . . . .
O2 O 0.2478(3) 0.8377(2) 0.65527(13) 0.0554(5) Uani 1 1 d . . . . .
O1 O 0.0480(4) 0.7211(3) 0.55427(12) 0.0587(5) Uani 1 1 d . . . . .
O3 O -0.0683(3) 0.6776(2) 0.70095(11) 0.0478(4) Uani 1 1 d . . . . .
C5 C 0.3075(4) 0.5207(3) 0.62578(14) 0.0336(5) Uani 1 1 d . . . . .
C13 C 0.1233(4) 0.7145(3) 1.04781(16) 0.0385(5) Uani 1 1 d . . . . .
N2 N 0.0643(3) 0.6771(2) 0.82716(13) 0.0384(4) Uani 1 1 d . . . . .
N1 N -0.3300(3) 0.8639(3) 0.89597(13) 0.0409(5) Uani 1 1 d . . . . .
C3 C 0.3914(5) 0.2422(3) 0.58055(18) 0.0501(7) Uani 1 1 d . . . . .
H3 H 0.357508 0.151365 0.552688 0.060 Uiso 1 1 calc R . . . .
C14 C -0.0726(4) 0.8072(3) 1.08191(15) 0.0376(5) Uani 1 1 d . . . . .
C11 C 0.0205(4) 0.7231(3) 0.91099(15) 0.0344(5) Uani 1 1 d . . . . .
C2 C 0.5748(4) 0.2288(3) 0.61754(16) 0.0438(6) Uani 1 1 d . . . . .
C6 C 0.4906(4) 0.5112(3) 0.66352(18) 0.0482(6) Uani 1 1 d . . . . .
H6 H 0.523795 0.601680 0.691871 0.058 Uiso 1 1 calc R . . . .
C10 C -0.1768(4) 0.8169(3) 0.94486(15) 0.0339(5) Uani 1 1 d . . . . .
C4 C 0.2568(4) 0.3871(3) 0.58381(17) 0.0448(6) Uani 1 1 d . . . . .
H4 H 0.133831 0.394689 0.558152 0.054 Uiso 1 1 calc R . . . .
C8 C -0.0855(4) 0.7247(3) 0.78440(15) 0.0371(5) Uani 1 1 d . . . . .
C15 C -0.2189(4) 0.8594(3) 1.03093(15) 0.0375(5) Uani 1 1 d . . . . .
H15 H -0.346703 0.923229 1.053274 0.045 Uiso 1 1 calc R . . . .
C9 C -0.2851(4) 0.8180(3) 0.81729(16) 0.0410(5) Uani 1 1 d . . . . .
H9 H -0.385571 0.846776 0.781833 0.049 Uiso 1 1 calc R . . . .
C12 C 0.1706(4) 0.6739(3) 0.96417(16) 0.0398(5) Uani 1 1 d . . . . .
H12 H 0.301968 0.613812 0.942423 0.048 Uiso 1 1 calc R . . . .
C7 C 0.6228(4) 0.3655(4) 0.65835(18) 0.0512(7) Uani 1 1 d . . . . .
H7 H 0.747498 0.358555 0.682902 0.061 Uiso 1 1 calc R . . . .
C1 C 0.7218(6) 0.0710(4) 0.6126(2) 0.0676(9) Uani 1 1 d . . . . .
H1A H 0.634865 -0.021266 0.625497 0.101 Uiso 1 1 calc GR . . . .
H1B H 0.818508 0.074024 0.652754 0.101 Uiso 1 1 calc GR . . . .
H1C H 0.805999 0.059154 0.556440 0.101 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C13 1.892(2) . ?
Br2 C14 1.886(2) . ?
S1 O2 1.416(2) . ?
S1 O1 1.415(2) . ?
S1 O3 1.6216(18) . ?
S1 C5 1.742(2) . ?
O3 C8 1.383(3) . ?
C5 C6 1.381(3) . ?
C5 C4 1.379(3) . ?
C13 C14 1.404(3) . ?
C13 C12 1.362(4) . ?
N2 C11 1.376(3) . ?
N2 C8 1.282(3) . ?
N1 C10 1.364(3) . ?
N1 C9 1.298(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.375(4) . ?
C3 C4 1.377(4) . ?
C14 C15 1.364(4) . ?
C11 C10 1.414(3) . ?
C11 C12 1.402(3) . ?
C2 C7 1.382(4) . ?
C2 C1 1.501(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.374(4) . ?
C10 C15 1.403(3) . ?
C4 H4 0.9300 . ?
C8 C9 1.420(3) . ?
C15 H15 0.9300 . ?
C9 H9 0.9300 . ?
C12 H12 0.9300 . ?
C7 H7 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
O2 S1 O3 107.46(11) . . ?
O2 S1 C5 110.76(12) . . ?
O1 S1 O2 121.16(14) . . ?
O1 S1 O3 101.83(12) . . ?
O1 S1 C5 109.36(11) . . ?
O3 S1 C5 104.66(11) . . ?
C8 O3 S1 123.27(16) . . ?
C6 C5 S1 119.57(18) . . ?
C4 C5 S1 119.35(18) . . ?
C4 C5 C6 121.1(2) . . ?
C14 C13 Br1 120.20(19) . . ?
C12 C13 Br1 118.58(18) . . ?
C12 C13 C14 121.2(2) . . ?
C8 N2 C11 115.05(19) . . ?
C9 N1 C10 116.6(2) . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.5(2) . . ?
C4 C3 H3 119.2 . . ?
C13 C14 Br2 121.98(19) . . ?
C15 C14 Br2 118.00(17) . . ?
C15 C14 C13 120.0(2) . . ?
N2 C11 C10 120.8(2) . . ?
N2 C11 C12 119.8(2) . . ?
C12 C11 C10 119.3(2) . . ?
C3 C2 C7 118.3(2) . . ?
C3 C2 C1 121.0(3) . . ?
C7 C2 C1 120.6(3) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 C5 118.7(2) . . ?
C7 C6 H6 120.7 . . ?
N1 C10 C11 121.3(2) . . ?
N1 C10 C15 119.1(2) . . ?
C15 C10 C11 119.5(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 H4 120.6 . . ?
O3 C8 C9 114.0(2) . . ?
N2 C8 O3 120.9(2) . . ?
N2 C8 C9 125.0(2) . . ?
C14 C15 C10 120.1(2) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
N1 C9 C8 121.2(2) . . ?
N1 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C2 C7 H7 119.2 . . ?
C6 C7 C2 121.6(2) . . ?
C6 C7 H7 119.2 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C13 C14 Br2 -0.9(3) . . . . ?
Br1 C13 C14 C15 179.37(18) . . . . ?
Br1 C13 C12 C11 179.23(18) . . . . ?
Br2 C14 C15 C10 -178.09(17) . . . . ?
S1 O3 C8 N2 -53.7(3) . . . . ?
S1 O3 C8 C9 130.1(2) . . . . ?
S1 C5 C6 C7 -177.9(2) . . . . ?
S1 C5 C4 C3 178.5(2) . . . . ?
O2 S1 O3 C8 -23.1(2) . . . . ?
O2 S1 C5 C6 12.5(2) . . . . ?
O2 S1 C5 C4 -165.6(2) . . . . ?
O1 S1 O3 C8 -151.4(2) . . . . ?
O1 S1 C5 C6 148.5(2) . . . . ?
O1 S1 C5 C4 -29.6(2) . . . . ?
O3 S1 C5 C6 -103.1(2) . . . . ?
O3 S1 C5 C4 78.9(2) . . . . ?
O3 C8 C9 N1 176.4(2) . . . . ?
C5 S1 O3 C8 94.7(2) . . . . ?
C5 C6 C7 C2 -0.9(4) . . . . ?
C13 C14 C15 C10 1.7(4) . . . . ?
N2 C11 C10 N1 0.4(3) . . . . ?
N2 C11 C10 C15 178.8(2) . . . . ?
N2 C11 C12 C13 -177.6(2) . . . . ?
N2 C8 C9 N1 0.5(4) . . . . ?
N1 C10 C15 C14 177.0(2) . . . . ?
C3 C2 C7 C6 1.0(4) . . . . ?
C14 C13 C12 C11 -0.9(4) . . . . ?
C11 N2 C8 O3 -175.8(2) . . . . ?
C11 N2 C8 C9 0.0(4) . . . . ?
C11 C10 C15 C14 -1.5(3) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C6 C5 C4 C3 0.5(4) . . . . ?
C10 N1 C9 C8 -0.4(4) . . . . ?
C10 C11 C12 C13 1.1(4) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
C4 C3 C2 C7 -0.2(4) . . . . ?
C4 C3 C2 C1 -179.2(3) . . . . ?
C8 N2 C11 C10 -0.3(3) . . . . ?
C8 N2 C11 C12 178.3(2) . . . . ?
C9 N1 C10 C11 0.0(3) . . . . ?
C9 N1 C10 C15 -178.4(2) . . . . ?
C12 C13 C14 Br2 179.29(18) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C12 C11 C10 N1 -178.3(2) . . . . ?
C12 C11 C10 C15 0.1(3) . . . . ?
C1 C2 C7 C6 179.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
