# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20260107b_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2qq6l8
_database_code_depnum_ccdc_archive 'CCDC 2523790'
loop_
_audit_author_name
_audit_author_address
'Yao Zhou'
;Hubei Normal University
China
;
_audit_update_record             
;
2026-01-18 deposited with the CCDC.	2026-02-02 downloaded from the CCDC.
;
_audit_creation_date             2026-01-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 Cl N O2 S'
_chemical_formula_sum            'C11 H10 Cl N O2 S'
_chemical_formula_weight         255.71
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   8.1568(5)
_cell_length_b                   11.8101(8)
_cell_length_c                   12.0950(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.848(2)
_cell_angle_gamma                90
_cell_volume                     1115.13(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8423
_cell_measurement_temperature    302.0
_cell_measurement_theta_max      27.518
_cell_measurement_theta_min      2.692
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.905
_exptl_absorpt_coefficient_mu    0.512
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0842 before and 0.0693 after correction.
The Ratio of minimum to maximum transmission is 0.8350.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19512
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         2.691
_diffrn_ambient_temperature      302.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_diffrn_source_current           35.0
_diffrn_source_power             1.225
_diffrn_source_voltage           35.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2053
_reflns_number_total             2561
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.122
_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)+(0.0485P)²+0.8177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1303
_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 Ternary CH refined with riding coordinates:
 C00M(H00M)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B), C00U(H00C,H00D), C00V(H00E,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00P(H00P), C00Q(H00Q)
;
_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
Cl03 Cl 0.39875(11) -0.25330(7) 0.58011(9) 0.0828(3) Uani 1 1 d . . . . .
S01 S -0.07027(8) 0.10029(6) 0.25252(5) 0.0480(2) Uani 1 1 d . . . . .
O2 O 0.3022(2) 0.18869(16) 0.57628(13) 0.0529(5) Uani 1 1 d . . . . .
O3 O 0.0824(3) 0.51578(19) 0.3437(2) 0.0870(8) Uani 1 1 d . . . . .
N007 N 0.1542(3) 0.24041(16) 0.39364(15) 0.0392(4) Uani 1 1 d . . . . .
C009 C 0.2251(3) 0.1621(2) 0.47642(17) 0.0378(5) Uani 1 1 d . . . . .
C00E C 0.1963(3) 0.04035(19) 0.44316(17) 0.0355(5) Uani 1 1 d . . . . .
C00F C 0.0971(3) 0.2042(2) 0.27375(17) 0.0408(5) Uani 1 1 d . . . . .
H00A H 0.192907 0.172311 0.252051 0.049 Uiso 1 1 calc R U . . .
H00B H 0.055127 0.269171 0.224570 0.049 Uiso 1 1 calc R U . . .
C00J C 0.2997(3) -0.0401(2) 0.5146(2) 0.0445(5) Uani 1 1 d . . . . .
H00J H 0.392399 -0.017287 0.575541 0.053 Uiso 1 1 calc R U . . .
C00K C 0.0560(3) 0.0040(2) 0.35218(17) 0.0368(5) Uani 1 1 d . . . . .
C00M C 0.1430(3) 0.3577(2) 0.4246(2) 0.0433(5) Uani 1 1 d . . . . .
H00M H 0.170088 0.365195 0.508675 0.052 Uiso 1 1 calc R U . . .
C00N C 0.2642(3) -0.1536(2) 0.4946(2) 0.0478(6) Uani 1 1 d . . . . .
C00P C 0.1209(4) -0.1901(2) 0.4092(2) 0.0514(6) Uani 1 1 d . . . . .
H00P H 0.095285 -0.266809 0.399185 0.062 Uiso 1 1 calc R U . . .
C00Q C 0.0176(3) -0.1108(2) 0.3398(2) 0.0473(6) Uani 1 1 d . . . . .
H00Q H -0.080160 -0.134424 0.283212 0.057 Uiso 1 1 calc R U . . .
C00U C -0.0181(4) 0.4242(3) 0.3658(3) 0.0593(7) Uani 1 1 d . . . . .
H00C H -0.089124 0.388359 0.296157 0.071 Uiso 1 1 calc R U . . .
H00D H -0.085460 0.444099 0.417129 0.071 Uiso 1 1 calc R U . . .
C00V C 0.2346(4) 0.4482(3) 0.3769(3) 0.0709(9) Uani 1 1 d . . . . .
H00E H 0.327962 0.483590 0.435264 0.085 Uiso 1 1 calc R U . . .
H00F H 0.272440 0.422809 0.312085 0.085 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
Cl03 C00N 1.732(2) . ?
S01 C00F 1.798(3) . ?
S01 C00K 1.757(2) . ?
O2 C009 1.230(2) . ?
O3 C00U 1.428(4) . ?
O3 C00V 1.432(4) . ?
N007 C009 1.363(3) . ?
N007 C00F 1.453(3) . ?
N007 C00M 1.445(3) . ?
C009 C00E 1.493(3) . ?
C00E C00J 1.392(3) . ?
C00E C00K 1.405(3) . ?
C00F H00A 0.9700 . ?
C00F H00B 0.9700 . ?
C00J H00J 0.9300 . ?
C00J C00N 1.378(4) . ?
C00K C00Q 1.390(3) . ?
C00M H00M 0.9800 . ?
C00M C00U 1.519(3) . ?
C00M C00V 1.511(4) . ?
C00N C00P 1.385(4) . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.372(4) . ?
C00Q H00Q 0.9300 . ?
C00U H00C 0.9700 . ?
C00U H00D 0.9700 . ?
C00V H00E 0.9700 . ?
C00V H00F 0.9700 . ?

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
C00K S01 C00F 94.26(10) . . ?
C00U O3 C00V 91.3(2) . . ?
C009 N007 C00F 118.60(18) . . ?
C009 N007 C00M 120.38(18) . . ?
C00M N007 C00F 120.97(18) . . ?
O2 C009 N007 122.3(2) . . ?
O2 C009 C00E 120.4(2) . . ?
N007 C009 C00E 117.10(17) . . ?
C00J C00E C009 118.04(19) . . ?
C00J C00E C00K 119.1(2) . . ?
C00K C00E C009 122.30(19) . . ?
S01 C00F H00A 109.5 . . ?
S01 C00F H00B 109.5 . . ?
N007 C00F S01 110.72(16) . . ?
N007 C00F H00A 109.5 . . ?
N007 C00F H00B 109.5 . . ?
H00A C00F H00B 108.1 . . ?
C00E C00J H00J 120.1 . . ?
C00N C00J C00E 119.8(2) . . ?
C00N C00J H00J 120.1 . . ?
C00E C00K S01 121.44(18) . . ?
C00Q C00K S01 119.24(17) . . ?
C00Q C00K C00E 119.3(2) . . ?
N007 C00M H00M 110.1 . . ?
N007 C00M C00U 119.1(2) . . ?
N007 C00M C00V 120.2(2) . . ?
C00U C00M H00M 110.1 . . ?
C00V C00M H00M 110.1 . . ?
C00V C00M C00U 84.9(2) . . ?
C00J C00N Cl03 119.5(2) . . ?
C00J C00N C00P 121.5(2) . . ?
C00P C00N Cl03 119.0(2) . . ?
C00N C00P H00P 120.6 . . ?
C00Q C00P C00N 118.7(2) . . ?
C00Q C00P H00P 120.6 . . ?
C00K C00Q H00Q 119.3 . . ?
C00P C00Q C00K 121.3(2) . . ?
C00P C00Q H00Q 119.3 . . ?
O3 C00U C00M 90.8(2) . . ?
O3 C00U H00C 113.5 . . ?
O3 C00U H00D 113.5 . . ?
C00M C00U H00C 113.5 . . ?
C00M C00U H00D 113.5 . . ?
H00C C00U H00D 110.8 . . ?
O3 C00V C00M 91.0(2) . . ?
O3 C00V H00E 113.5 . . ?
O3 C00V H00F 113.5 . . ?
C00M C00V H00E 113.5 . . ?
C00M C00V H00F 113.5 . . ?
H00E C00V H00F 110.8 . . ?

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
Cl03 C00N C00P C00Q -178.2(2) . . . . ?
S01 C00K C00Q C00P 174.3(2) . . . . ?
O2 C009 C00E C00J -19.3(3) . . . . ?
O2 C009 C00E C00K 152.2(2) . . . . ?
N007 C009 C00E C00J 164.4(2) . . . . ?
N007 C009 C00E C00K -24.1(3) . . . . ?
N007 C00M C00U O3 -132.2(2) . . . . ?
N007 C00M C00V O3 131.1(2) . . . . ?
C009 N007 C00F S01 62.0(2) . . . . ?
C009 N007 C00M C00U -139.7(2) . . . . ?
C009 N007 C00M C00V 118.4(3) . . . . ?
C009 C00E C00J C00N 172.3(2) . . . . ?
C009 C00E C00K S01 13.3(3) . . . . ?
C009 C00E C00K C00Q -167.6(2) . . . . ?
C00E C00J C00N Cl03 177.33(18) . . . . ?
C00E C00J C00N C00P -4.2(4) . . . . ?
C00E C00K C00Q C00P -4.8(4) . . . . ?
C00F S01 C00K C00E 25.0(2) . . . . ?
C00F S01 C00K C00Q -154.2(2) . . . . ?
C00F N007 C009 O2 167.4(2) . . . . ?
C00F N007 C009 C00E -16.3(3) . . . . ?
C00F N007 C00M C00U 42.9(3) . . . . ?
C00F N007 C00M C00V -59.1(3) . . . . ?
C00J C00E C00K S01 -175.28(17) . . . . ?
C00J C00E C00K C00Q 3.8(3) . . . . ?
C00J C00N C00P C00Q 3.3(4) . . . . ?
C00K S01 C00F N007 -59.36(17) . . . . ?
C00K C00E C00J C00N 0.6(3) . . . . ?
C00M N007 C009 O2 -10.1(4) . . . . ?
C00M N007 C009 C00E 166.2(2) . . . . ?
C00M N007 C00F S01 -120.5(2) . . . . ?
C00N C00P C00Q C00K 1.3(4) . . . . ?
C00U O3 C00V C00M -10.9(2) . . . . ?
C00U C00M C00V O3 10.3(2) . . . . ?
C00V O3 C00U C00M 10.8(2) . . . . ?
C00V C00M C00U O3 -10.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_20260108f_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2qq6m9
_database_code_depnum_ccdc_archive 'CCDC 2523791'
loop_
_audit_author_name
_audit_author_address
'Yao Zhou'
;Hubei Normal University
China
;
_audit_update_record             
;
2026-01-18 deposited with the CCDC.	2026-02-02 downloaded from the CCDC.
;
_audit_creation_date             2026-01-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         'C8 H5 Br O2 S'
_chemical_formula_sum            'C8 H5 Br O2 S'
_chemical_formula_weight         245.09
_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'
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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   9.9100(13)
_cell_length_b                   22.220(3)
_cell_length_c                   7.4284(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1635.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8663
_cell_measurement_temperature    303.0
_cell_measurement_theta_max      27.491
_cell_measurement_theta_min      2.750
_shelx_estimated_absorpt_T_max   0.623
_shelx_estimated_absorpt_T_min   0.573
_exptl_absorpt_coefficient_mu    5.229
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.1769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1821 before and 0.1205 after correction.
The Ratio of minimum to maximum transmission is 0.2373.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.990
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1474
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            32299
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         27.572
_diffrn_reflns_theta_min         3.434
_diffrn_ambient_temperature      303.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_diffrn_source_current           35.0
_diffrn_source_power             1.225
_diffrn_source_voltage           35.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1431
_reflns_number_total             1881
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       0.0134(12)
_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   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1881
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.172
_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)+(0.0430P)²+4.8231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1311
_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:
 C00C(H00B,H00C)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00A(H00A)
;
_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
Br01 Br 0.00226(5) 0.59958(3) 0.57347(7) 0.0390(2) Uani 1 1 d . . . . .
S002 S 0.64841(12) 0.59776(6) 0.59671(19) 0.0335(3) Uani 1 1 d . . . . .
O003 O 0.6072(4) 0.71156(16) 0.4910(6) 0.0399(9) Uani 1 1 d . . . . .
O004 O 0.4231(4) 0.73835(16) 0.3508(6) 0.0446(10) Uani 1 1 d . . . . .
C005 C 0.1933(5) 0.5998(2) 0.5748(5) 0.0243(9) Uani 1 1 d . . . . .
C006 C 0.4714(5) 0.5984(2) 0.5864(6) 0.0230(9) Uani 1 1 d . . . . .
C007 C 0.2623(5) 0.6508(2) 0.5243(6) 0.0245(10) Uani 1 1 d . . . . .
H007 H 0.215942 0.685111 0.488180 0.029 Uiso 1 1 calc R U . . .
C008 C 0.2593(5) 0.5476(2) 0.6272(6) 0.0283(10) Uani 1 1 d . . . . .
H008 H 0.210358 0.513438 0.658164 0.034 Uiso 1 1 calc R U . . .
C009 C 0.4040(5) 0.6502(2) 0.5283(6) 0.0218(9) Uani 1 1 d . . . . .
C00A C 0.3983(5) 0.5471(2) 0.6328(7) 0.0282(10) Uani 1 1 d . . . . .
H00A H 0.443609 0.512388 0.667682 0.034 Uiso 1 1 calc R U . . .
C00B C 0.4742(5) 0.7034(2) 0.4541(7) 0.0289(11) Uani 1 1 d . . . . .
C00C C 0.6611(5) 0.6772(2) 0.6378(8) 0.0380(12) Uani 1 1 d . . . . .
H00B H 0.612380 0.687141 0.747154 0.046 Uiso 1 1 calc R U . . .
H00C H 0.755052 0.687912 0.655576 0.046 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
Br01 C005 1.894(5) . ?
S002 C006 1.756(5) . ?
S002 C00C 1.796(5) . ?
O003 C00B 1.359(6) . ?
O003 C00C 1.434(7) . ?
O004 C00B 1.204(6) . ?
C005 C007 1.375(6) . ?
C005 C008 1.387(7) . ?
C006 C009 1.399(6) . ?
C006 C00A 1.392(7) . ?
C007 H007 0.9300 . ?
C007 C009 1.404(6) . ?
C008 H008 0.9300 . ?
C008 C00A 1.379(7) . ?
C009 C00B 1.479(6) . ?
C00A H00A 0.9300 . ?
C00C H00B 0.9700 . ?
C00C H00C 0.9700 . ?

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
C006 S002 C00C 94.0(2) . . ?
C00B O003 C00C 116.3(4) . . ?
C007 C005 Br01 119.9(4) . . ?
C007 C005 C008 122.1(4) . . ?
C008 C005 Br01 118.0(4) . . ?
C009 C006 S002 119.8(4) . . ?
C00A C006 S002 120.1(4) . . ?
C00A C006 C009 120.1(4) . . ?
C005 C007 H007 120.5 . . ?
C005 C007 C009 118.9(4) . . ?
C009 C007 H007 120.5 . . ?
C005 C008 H008 120.5 . . ?
C00A C008 C005 119.1(4) . . ?
C00A C008 H008 120.5 . . ?
C006 C009 C007 119.5(4) . . ?
C006 C009 C00B 123.3(4) . . ?
C007 C009 C00B 117.0(4) . . ?
C006 C00A H00A 119.8 . . ?
C008 C00A C006 120.4(4) . . ?
C008 C00A H00A 119.8 . . ?
O003 C00B C009 119.2(4) . . ?
O004 C00B O003 116.8(4) . . ?
O004 C00B C009 123.8(5) . . ?
S002 C00C H00B 109.3 . . ?
S002 C00C H00C 109.3 . . ?
O003 C00C S002 111.6(4) . . ?
O003 C00C H00B 109.3 . . ?
O003 C00C H00C 109.3 . . ?
H00B C00C H00C 108.0 . . ?

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
Br01 C005 C007 C009 179.3(3) . . . . ?
Br01 C005 C008 C00A -178.7(4) . . . . ?
S002 C006 C009 C007 -178.5(3) . . . . ?
S002 C006 C009 C00B 7.2(6) . . . . ?
S002 C006 C00A C008 179.1(4) . . . . ?
C005 C007 C009 C006 -1.2(7) . . . . ?
C005 C007 C009 C00B 173.4(4) . . . . ?
C005 C008 C00A C006 0.0(8) . . . . ?
C006 S002 C00C O003 -62.0(4) . . . . ?
C006 C009 C00B O003 -20.6(7) . . . . ?
C006 C009 C00B O004 153.8(5) . . . . ?
C007 C005 C008 C00A 1.4(7) . . . . ?
C007 C009 C00B O003 165.1(4) . . . . ?
C007 C009 C00B O004 -20.6(7) . . . . ?
C008 C005 C007 C009 -0.8(7) . . . . ?
C009 C006 C00A C008 -2.0(7) . . . . ?
C00A C006 C009 C007 2.6(7) . . . . ?
C00A C006 C009 C00B -171.6(4) . . . . ?
C00B O003 C00C S002 61.6(5) . . . . ?
C00C S002 C006 C009 28.9(4) . . . . ?
C00C S002 C006 C00A -152.2(4) . . . . ?
C00C O003 C00B O004 168.8(5) . . . . ?
C00C O003 C00B C009 -16.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
