# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_chenxi_tshch_0313_auto
_database_code_depnum_ccdc_archive 'CCDC 2308103'
loop_
_audit_author_name
_audit_author_address
CHENXI
;LANZHOU UNIVERSITY
China
;
_audit_update_record             
;
2023-11-15 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_audit_creation_date             2023-11-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H16 Br N O2 S2'
_chemical_formula_sum            'C18 H16 Br N O2 S2'
_chemical_formula_weight         422.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y+1/2, z+1/2'
3 '-x, y, -z+1/2'
4 'x+1/2, -y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y-1/2, -z-1/2'
7 'x, -y, z-1/2'
8 '-x-1/2, y-1/2, z'

_cell_length_a                   18.3295(3)
_cell_length_b                   10.5061(2)
_cell_length_c                   18.8191(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3624.02(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    300.49(10)
_cell_measurement_theta_max      75.9710
_cell_measurement_theta_min      3.3650
_exptl_absorpt_coefficient_mu    5.331
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12880
_diffrn_reflns_theta_full        76.52
_diffrn_reflns_theta_max         76.52
_diffrn_reflns_theta_min         4.70
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.49(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  22.00   0.50    0.05    --   44.44 -17.00  84.00   96
  2  ω    -29.00  20.00   0.50    0.05    --   44.44 -19.00   0.00   98
  3  ω    -25.00  13.00   0.50    0.05    --   44.44 -37.00 -30.00   76
  4  ω    126.00 162.00   0.50    0.05    --  109.62 145.00 -93.00   72
  5  ω     64.00 107.00   0.50    0.05    --  109.62 145.00 -93.00   86
  6  ω     40.00  65.00   0.50    0.05    --  109.62-125.00  60.00   50
  7  ω     84.00 111.00   0.50    0.05    --  109.62-125.00  60.00   54
  8  ω     37.00  98.00   0.50    0.05    --  109.62 -94.00 -60.00  122
  9  ω     75.00 101.00   0.50    0.05    --  109.62 -94.00 -90.00   52
 10  ω    -54.00 -25.00   0.50    0.05    -- -100.00  45.00  30.00   58
 11  ω    -54.00 -26.00   0.50    0.05    -- -100.00  45.00  60.00   56
 12  ω    -54.00 -29.00   0.50    0.05    -- -100.00  45.00 120.00   50
 13  ω   -150.00 -84.00   0.50    0.05    -- -100.00 -17.00  84.00  132
 14  ω   -165.00 -90.00   0.50    0.05    -- -100.00-109.00 -78.00  150
 15  ω   -115.00 -80.00   0.50    0.05    --  -44.44-179.00 -60.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0704888000
_diffrn_orient_matrix_UB_12      0.0731146000
_diffrn_orient_matrix_UB_13      -0.0182704000
_diffrn_orient_matrix_UB_21      0.0419195000
_diffrn_orient_matrix_UB_22      0.1267817000
_diffrn_orient_matrix_UB_23      0.0038419000
_diffrn_orient_matrix_UB_31      0.0181623000
_diffrn_orient_matrix_UB_32      -0.0107470000
_diffrn_orient_matrix_UB_33      -0.0796898000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3169
_reflns_number_total             3578
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3578
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0684P)²+1.7340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1231
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C12(H12A,H12B), C16(H16A,H16B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.234454(19) -0.10025(3) 0.39758(2) 0.07095(17) Uani 1 d . . .
S1 S 0.61282(4) 0.47735(7) 0.45571(3) 0.05120(19) Uani 1 d . . .
S2 S 0.63541(4) 0.43962(7) 0.29768(4) 0.0540(2) Uani 1 d . . .
O1 O 0.65029(18) 0.9093(3) 0.3021(2) 0.1069(11) Uani 1 d . . .
O2 O 0.5618(3) 1.0293(3) 0.3247(3) 0.181(2) Uani 1 d . . .
N00E N 0.5886(2) 0.9266(3) 0.32245(18) 0.0785(8) Uani 1 d . . .
C1 C 0.53253(15) 0.5924(2) 0.35809(13) 0.0447(5) Uani 1 d . . .
C2 C 0.57559(16) 0.6976(3) 0.34324(13) 0.0507(6) Uani 1 d . . .
H2 H 0.6257 0.6890 0.3368 0.061 Uiso 1 calc . . R
C3 C 0.51195(15) 0.3567(2) 0.36466(14) 0.0477(6) Uani 1 d . . .
H3 H 0.4950 0.3373 0.3193 0.057 Uiso 1 calc . . R
C4 C 0.48423(15) 0.2889(2) 0.41713(14) 0.0470(6) Uani 1 d . . .
H4 H 0.5034 0.3023 0.4623 0.056 Uiso 1 calc . . R
C5 C 0.42561(15) 0.1941(2) 0.41051(13) 0.0455(5) Uani 1 d . . .
C6 C 0.31205(15) 0.0196(3) 0.40356(15) 0.0519(6) Uani 1 d . . .
C7 C 0.56754(14) 0.4616(2) 0.36922(13) 0.0445(5) Uani 1 d . . .
C8 C 0.33098(16) 0.0874(2) 0.34344(16) 0.0527(6) Uani 1 d . . .
H8 H 0.3059 0.0755 0.3010 0.063 Uiso 1 calc . . R
C9 C 0.38793(15) 0.1731(3) 0.34759(15) 0.0509(6) Uani 1 d . . .
H9 H 0.4014 0.2180 0.3071 0.061 Uiso 1 calc . . R
C10 C 0.45774(17) 0.6094(3) 0.36583(17) 0.0574(7) Uani 1 d . . .
H10 H 0.4280 0.5396 0.3750 0.069 Uiso 1 calc . . R
C11 C 0.54261(18) 0.8156(3) 0.33816(14) 0.0553(7) Uani 1 d . . .
C12 C 0.66452(17) 0.3314(3) 0.46128(17) 0.0624(7) Uani 1 d . . .
H12A H 0.6916 0.3312 0.5056 0.075 Uiso 1 calc . . R
H12B H 0.6307 0.2604 0.4627 0.075 Uiso 1 calc . . R
C13 C 0.40483(19) 0.1235(3) 0.46963(15) 0.0608(7) Uani 1 d . . .
H13 H 0.4294 0.1351 0.5124 0.073 Uiso 1 calc . . R
C14 C 0.34810(18) 0.0361(3) 0.46607(16) 0.0637(8) Uani 1 d . . .
H14 H 0.3349 -0.0107 0.5060 0.076 Uiso 1 calc . . R
C15 C 0.4693(2) 0.8340(3) 0.34666(16) 0.0656(8) Uani 1 d . . .
H15 H 0.4490 0.9149 0.3435 0.079 Uiso 1 calc . . R
C16 C 0.68077(17) 0.2971(3) 0.32853(18) 0.0643(8) Uani 1 d . . .
H16A H 0.6452 0.2288 0.3312 0.077 Uiso 1 calc . . R
H16B H 0.7173 0.2727 0.2938 0.077 Uiso 1 calc . . R
C17 C 0.4270(2) 0.7296(3) 0.36001(18) 0.0706(9) Uani 1 d . . .
H17 H 0.3768 0.7393 0.3653 0.085 Uiso 1 calc . . R
C18 C 0.71753(19) 0.3106(4) 0.40064(18) 0.0710(9) Uani 1 d . . .
H18A H 0.7457 0.2343 0.4101 0.085 Uiso 1 calc . . R
H18B H 0.7512 0.3818 0.3989 0.085 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C6 1.903(3) . ?
S1 C7 1.835(3) . ?
S1 C12 1.806(3) . ?
S2 C7 1.848(3) . ?
S2 C16 1.808(3) . ?
O1 N00E 1.207(5) . ?
O2 N00E 1.186(5) . ?
N00E C11 1.470(4) . ?
C1 C2 1.387(4) . ?
C1 C7 1.531(3) . ?
C1 C10 1.390(4) . ?
C2 C11 1.382(4) . ?
C3 C4 1.319(4) . ?
C3 C7 1.503(3) . ?
C4 C5 1.471(4) . ?
C5 C9 1.388(4) . ?
C5 C13 1.390(4) . ?
C6 C8 1.381(4) . ?
C6 C14 1.360(4) . ?
C8 C9 1.381(4) . ?
C10 C17 1.387(4) . ?
C11 C15 1.366(5) . ?
C12 C18 1.515(5) . ?
C13 C14 1.389(4) . ?
C15 C17 1.367(5) . ?
C16 C18 1.522(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C7 102.25(13) . . ?
C16 S2 C7 100.31(14) . . ?
O1 N00E C11 118.8(3) . . ?
O2 N00E O1 122.4(4) . . ?
O2 N00E C11 118.5(4) . . ?
C2 C1 C7 120.3(2) . . ?
C2 C1 C10 118.7(2) . . ?
C10 C1 C7 121.0(2) . . ?
C11 C2 C1 118.7(3) . . ?
C4 C3 C7 127.9(2) . . ?
C3 C4 C5 125.7(2) . . ?
C9 C5 C4 122.9(2) . . ?
C9 C5 C13 117.5(3) . . ?
C13 C5 C4 119.6(2) . . ?
C8 C6 Br1 118.7(2) . . ?
C14 C6 Br1 119.9(2) . . ?
C14 C6 C8 121.4(3) . . ?
S1 C7 S2 110.69(14) . . ?
C1 C7 S1 103.28(16) . . ?
C1 C7 S2 107.12(17) . . ?
C3 C7 S1 115.06(18) . . ?
C3 C7 S2 108.87(17) . . ?
C3 C7 C1 111.5(2) . . ?
C9 C8 C6 118.7(3) . . ?
C8 C9 C5 121.9(3) . . ?
C17 C10 C1 120.7(3) . . ?
C2 C11 N00E 118.3(3) . . ?
C15 C11 N00E 118.4(3) . . ?
C15 C11 C2 123.3(3) . . ?
C18 C12 S1 114.5(2) . . ?
C14 C13 C5 121.3(3) . . ?
C6 C14 C13 119.3(3) . . ?
C11 C15 C17 117.8(3) . . ?
C18 C16 S2 114.4(2) . . ?
C15 C17 C10 120.9(3) . . ?
C12 C18 C16 113.7(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.171
_oxdiff_exptl_absorpt_empirical_full_min 0.500
