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

# 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_exp_7395
_database_code_depnum_ccdc_archive 'CCDC 2097707'
loop_
_audit_author_name
_audit_author_address
'Dong Ziyang'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2021-07-20 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_audit_creation_date             2021-07-14
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H14 Br N O2 S2'
_chemical_formula_sum            'C18 H14 Br N O2 S2'
_chemical_formula_weight         420.33
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.3517(4)
_cell_length_b                   20.2201(10)
_cell_length_c                   11.9402(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.625(4)
_cell_angle_gamma                90.00
_cell_volume                     1774.23(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1950
_cell_measurement_temperature    116.10(10)
_cell_measurement_theta_max      27.6830
_cell_measurement_theta_min      3.5550
_exptl_absorpt_coefficient_mu    2.562
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.34
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7333
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.37
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      116.10(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.8310
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   29.00   81.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       16.2414   77.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega   48.00   85.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       16.2414  178.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00   27.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -11.0070  -99.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega  -21.00   54.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       16.2414  -99.0000    0.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0453875000
_diffrn_orient_matrix_UB_12      -0.0215932000
_diffrn_orient_matrix_UB_13      0.0382658000
_diffrn_orient_matrix_UB_21      -0.0015267000
_diffrn_orient_matrix_UB_22      0.0249007000
_diffrn_orient_matrix_UB_23      0.0418592000
_diffrn_orient_matrix_UB_31      -0.0851662000
_diffrn_orient_matrix_UB_32      -0.0119829000
_diffrn_orient_matrix_UB_33      0.0178048000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2689
_reflns_number_total             3407
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0271P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0807
_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. 
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.36628(5) 0.542288(19) 0.59176(3) 0.03636(13) Uani 1 1 d . . .
S1 S -0.26612(11) 0.74272(4) 0.78392(6) 0.0211(2) Uani 1 1 d . . .
S2 S -0.46831(11) 0.79818(4) 0.85596(6) 0.0230(2) Uani 1 1 d . . .
O2 O -0.6380(3) 0.84662(10) 0.49356(14) 0.0195(5) Uani 1 1 d . . .
O1 O -0.3678(3) 0.89871(12) 0.48548(16) 0.0321(6) Uani 1 1 d . . .
C13 C -0.0758(4) 0.70749(16) 0.5745(2) 0.0180(7) Uani 1 1 d . . .
N1 N -0.2069(3) 0.75872(13) 0.56176(18) 0.0185(6) Uani 1 1 d . . .
C4 C -0.6862(4) 0.88711(16) 0.7396(2) 0.0171(7) Uani 1 1 d . . .
C3 C -0.5305(4) 0.84094(15) 0.7340(2) 0.0162(7) Uani 1 1 d . . .
C2 C -0.4334(4) 0.82885(15) 0.6415(2) 0.0162(7) Uani 1 1 d . . .
C10 C -0.4714(4) 0.86270(16) 0.5315(2) 0.0189(7) Uani 1 1 d . . .
C1 C -0.2944(4) 0.77794(15) 0.6468(2) 0.0160(7) Uani 1 1 d . . .
C5 C -0.6768(4) 0.94972(16) 0.6909(2) 0.0247(8) Uani 1 1 d . . .
H5 H -0.5671 0.9647 0.6633 0.030 Uiso 1 1 calc R . .
C15 C 0.2380(4) 0.67465(17) 0.5937(2) 0.0222(8) Uani 1 1 d . . .
H15 H 0.3605 0.6854 0.6031 0.027 Uiso 1 1 calc R . .
C6 C -0.8287(5) 0.98950(18) 0.6832(3) 0.0316(9) Uani 1 1 d . . .
H6 H -0.8221 1.0308 0.6494 0.038 Uiso 1 1 calc R . .
C9 C -0.8498(4) 0.86654(16) 0.7854(2) 0.0193(7) Uani 1 1 d . . .
H9 H -0.8565 0.8257 0.8209 0.023 Uiso 1 1 calc R . .
C8 C -1.0015(4) 0.90689(17) 0.7778(2) 0.0220(7) Uani 1 1 d . . .
H8 H -1.1105 0.8929 0.8077 0.026 Uiso 1 1 calc R . .
C16 C 0.1847(4) 0.60947(17) 0.5858(2) 0.0221(8) Uani 1 1 d . . .
C7 C -0.9917(5) 0.96781(17) 0.7261(2) 0.0282(8) Uani 1 1 d . . .
H7 H -1.0947 0.9944 0.7200 0.034 Uiso 1 1 calc R . .
C12 C -0.8970(4) 0.85746(17) 0.3741(2) 0.0256(8) Uani 1 1 d . . .
H12A H -0.9480 0.8780 0.3079 0.038 Uiso 1 1 calc R . .
H12B H -0.9677 0.8693 0.4374 0.038 Uiso 1 1 calc R . .
H12C H -0.8984 0.8103 0.3650 0.038 Uiso 1 1 calc R . .
C17 C 0.0036(4) 0.59202(17) 0.5726(2) 0.0231(8) Uani 1 1 d . . .
H17 H -0.0308 0.5478 0.5680 0.028 Uiso 1 1 calc R . .
C11 C -0.7051(4) 0.88048(17) 0.3929(2) 0.0266(8) Uani 1 1 d . . .
H11A H -0.6318 0.8691 0.3294 0.032 Uiso 1 1 calc R . .
H11B H -0.7013 0.9280 0.4034 0.032 Uiso 1 1 calc R . .
C18 C -0.1253(4) 0.64169(17) 0.5666(2) 0.0209(7) Uani 1 1 d . . .
H18 H -0.2476 0.6307 0.5570 0.025 Uiso 1 1 calc R . .
C14 C 0.1077(4) 0.72424(17) 0.5876(2) 0.0208(7) Uani 1 1 d . . .
H14 H 0.1424 0.7684 0.5921 0.025 Uiso 1 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 C16 1.904(3) . ?
S1 S2 2.0687(11) . ?
S1 C1 1.792(3) . ?
S2 C3 1.743(3) . ?
O2 C10 1.334(3) . ?
O2 C11 1.457(3) . ?
O1 C10 1.198(3) . ?
C13 N1 1.420(4) . ?
C13 C18 1.382(4) . ?
C13 C14 1.395(4) . ?
N1 C1 1.278(3) . ?
C4 C3 1.480(4) . ?
C4 C5 1.396(4) . ?
C4 C9 1.399(4) . ?
C3 C2 1.354(4) . ?
C2 C10 1.501(4) . ?
C2 C1 1.451(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(4) . ?
C15 C14 1.388(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.388(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.383(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.381(4) . ?
C16 C17 1.382(4) . ?
C7 H7 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 C11 1.496(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C18 H18 0.9300 . ?
C14 H14 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 S2 95.65(11) . . ?
C3 S2 S1 95.51(10) . . ?
C10 O2 C11 116.8(2) . . ?
C18 C13 N1 121.2(3) . . ?
C18 C13 C14 119.6(3) . . ?
C14 C13 N1 119.1(3) . . ?
C1 N1 C13 119.5(2) . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 C9 119.1(3) . . ?
C9 C4 C3 120.3(3) . . ?
C4 C3 S2 117.4(2) . . ?
C2 C3 S2 117.4(2) . . ?
C2 C3 C4 125.2(3) . . ?
C3 C2 C10 122.9(3) . . ?
C3 C2 C1 118.7(2) . . ?
C1 C2 C10 118.3(2) . . ?
O2 C10 C2 109.4(2) . . ?
O1 C10 O2 125.6(3) . . ?
O1 C10 C2 125.0(3) . . ?
N1 C1 S1 123.9(2) . . ?
N1 C1 C2 123.4(2) . . ?
C2 C1 S1 112.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C16 C15 H15 120.2 . . ?
C16 C15 C14 119.5(3) . . ?
C14 C15 H15 120.2 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.9(3) . . ?
C7 C6 H6 120.1 . . ?
C4 C9 H9 120.0 . . ?
C8 C9 C4 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
C9 C8 H8 119.9 . . ?
C7 C8 C9 120.2(3) . . ?
C7 C8 H8 119.9 . . ?
C15 C16 Br1 118.8(2) . . ?
C15 C16 C17 121.6(3) . . ?
C17 C16 Br1 119.6(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.5(3) . . ?
C18 C17 H17 120.7 . . ?
O2 C11 C12 105.9(2) . . ?
O2 C11 H11A 110.6 . . ?
O2 C11 H11B 110.6 . . ?
C12 C11 H11A 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14 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 C16 C17 C18 -178.9(2) . . . . ?
S1 S2 C3 C4 176.6(2) . . . . ?
S1 S2 C3 C2 -2.9(2) . . . . ?
S2 S1 C1 N1 -175.9(3) . . . . ?
S2 S1 C1 C2 1.6(2) . . . . ?
S2 C3 C2 C10 -179.4(2) . . . . ?
S2 C3 C2 C1 4.7(4) . . . . ?
C13 N1 C1 S1 -1.4(4) . . . . ?
C13 N1 C1 C2 -178.6(3) . . . . ?
N1 C13 C18 C17 176.3(2) . . . . ?
N1 C13 C14 C15 -176.4(2) . . . . ?
C4 C3 C2 C10 1.2(5) . . . . ?
C4 C3 C2 C1 -174.7(3) . . . . ?
C4 C5 C6 C7 1.2(5) . . . . ?
C4 C9 C8 C7 -0.6(4) . . . . ?
C3 C4 C5 C6 171.7(3) . . . . ?
C3 C4 C9 C8 -172.0(3) . . . . ?
C3 C2 C10 O2 -63.0(4) . . . . ?
C3 C2 C10 O1 116.7(4) . . . . ?
C3 C2 C1 S1 -4.0(4) . . . . ?
C3 C2 C1 N1 173.5(3) . . . . ?
C10 O2 C11 C12 -175.8(3) . . . . ?
C10 C2 C1 S1 179.9(2) . . . . ?
C10 C2 C1 N1 -2.6(4) . . . . ?
C1 S1 S2 C3 0.55(14) . . . . ?
C1 C2 C10 O2 112.9(3) . . . . ?
C1 C2 C10 O1 -67.4(4) . . . . ?
C5 C4 C3 S2 135.9(2) . . . . ?
C5 C4 C3 C2 -44.7(4) . . . . ?
C5 C4 C9 C8 2.7(4) . . . . ?
C5 C6 C7 C8 0.9(5) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C9 C4 C3 S2 -49.4(3) . . . . ?
C9 C4 C3 C2 130.0(3) . . . . ?
C9 C4 C5 C6 -3.0(4) . . . . ?
C9 C8 C7 C6 -1.2(5) . . . . ?
C16 C15 C14 C13 0.6(4) . . . . ?
C16 C17 C18 C13 -0.7(4) . . . . ?
C11 O2 C10 O1 -5.9(4) . . . . ?
C11 O2 C10 C2 173.9(2) . . . . ?
C18 C13 N1 C1 86.5(4) . . . . ?
C18 C13 C14 C15 -0.7(4) . . . . ?
C14 C13 N1 C1 -97.9(3) . . . . ?
C14 C13 C18 C17 0.8(4) . . . . ?
C14 C15 C16 Br1 178.90(19) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?

