# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 1980884'
loop_
_audit_author_name
_audit_author_address
'Sikun Zhang'
;XJTU
China
;
_audit_update_record             
;
2020-01-30 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 B Br2 N S2'
_chemical_formula_weight         501.06

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'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.7998(4)
_cell_length_b                   17.9358(7)
_cell_length_c                   18.6892(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.223(2)
_cell_angle_gamma                90
_cell_volume                     3914.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9749
_cell_measurement_theta_min      2.367
_cell_measurement_theta_max      26.431

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    4.358
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       'area detector, ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14954
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.081
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4012
_reflns_number_gt                3066
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0603P)²+11.7996P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4012
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.33656(4) 0.91650(3) 0.25930(3) 0.05811(18) Uani 1 1 d . . . . .
Br2 Br 0.90768(7) 0.40228(4) 0.59303(3) 0.0836(2) Uani 1 1 d . . . . .
S2 S 0.67829(10) 0.48025(6) 0.61214(5) 0.0464(3) Uani 1 1 d . . . . .
S1 S 0.43422(10) 0.58703(7) 0.62985(6) 0.0520(3) Uani 1 1 d . . . . .
N1 N 0.5540(3) 0.67399(17) 0.46317(15) 0.0327(7) Uani 1 1 d . . . . .
C15 C 0.7282(3) 0.6586(2) 0.39043(18) 0.0315(8) Uani 1 1 d . . . . .
C4 C 0.5059(3) 0.7330(2) 0.41505(19) 0.0335(8) Uani 1 1 d . . . . .
C3 C 0.4479(3) 0.7137(2) 0.3480(2) 0.0356(8) Uani 1 1 d . . . . .
H3 H 0.4412 0.6638 0.3343 0.043 Uiso 1 1 calc R U . . .
C12 C 0.6915(3) 0.5704(2) 0.50366(19) 0.0360(8) Uani 1 1 d . . . . .
C11 C 0.6240(3) 0.5541(2) 0.55765(19) 0.0364(9) Uani 1 1 d . . . . .
C7 C 0.4919(3) 0.6555(2) 0.51881(19) 0.0371(9) Uani 1 1 d . . . . .
C1 C 0.4098(3) 0.8425(2) 0.3226(2) 0.0399(9) Uani 1 1 d . . . . .
C2 C 0.3996(3) 0.7689(2) 0.3011(2) 0.0396(9) Uani 1 1 d . . . . .
H2 H 0.3608 0.7564 0.2558 0.048 Uiso 1 1 calc R U . . .
C20 C 0.7738(3) 0.7298(2) 0.3864(2) 0.0391(9) Uani 1 1 d . . . . .
H20 H 0.7591 0.7657 0.4198 0.047 Uiso 1 1 calc R U . . .
C10 C 0.5255(3) 0.5964(2) 0.56513(19) 0.0377(9) Uani 1 1 d . . . . .
C16 C 0.7520(4) 0.6064(2) 0.3389(2) 0.0448(10) Uani 1 1 d . . . . .
H16 H 0.7238 0.5581 0.3407 0.054 Uiso 1 1 calc R U . . .
C5 C 0.5171(4) 0.8072(2) 0.4353(2) 0.0437(10) Uani 1 1 d . . . . .
H5 H 0.5571 0.8199 0.4801 0.052 Uiso 1 1 calc R U . . .
C6 C 0.4686(4) 0.8625(2) 0.3889(2) 0.0468(10) Uani 1 1 d . . . . .
H6 H 0.4757 0.9124 0.4023 0.056 Uiso 1 1 calc R U . . .
C13 C 0.7889(4) 0.5218(2) 0.5087(2) 0.0452(10) Uani 1 1 d . . . . .
H13 H 0.8436 0.5242 0.4776 0.054 Uiso 1 1 calc R U . . .
C19 C 0.8404(4) 0.7486(3) 0.3338(2) 0.0505(11) Uani 1 1 d . . . . .
H19 H 0.8717 0.7962 0.3328 0.061 Uiso 1 1 calc R U . . .
C18 C 0.8601(4) 0.6957(3) 0.2823(2) 0.0510(11) Uani 1 1 d . . . . .
H18 H 0.9027 0.7083 0.2459 0.061 Uiso 1 1 calc R U . . .
C14 C 0.7928(4) 0.4721(2) 0.5637(2) 0.0495(11) Uani 1 1 d . . . . .
C8 C 0.3911(4) 0.6926(3) 0.5360(2) 0.0494(11) Uani 1 1 d . . . . .
H8 H 0.3567 0.7331 0.5105 0.059 Uiso 1 1 calc R U . . .
C17 C 0.8167(4) 0.6253(3) 0.2855(2) 0.0523(11) Uani 1 1 d . . . . .
H17 H 0.8308 0.5898 0.2515 0.063 Uiso 1 1 calc R U . . .
B1 B 0.6567(4) 0.6347(2) 0.4519(2) 0.0334(9) Uani 1 1 d . . . . .
C9 C 0.3524(4) 0.6611(3) 0.5940(3) 0.0585(12) Uani 1 1 d . . . . .
H9 H 0.2880 0.6779 0.6125 0.070 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 C1 1.901(4) . ?
Br2 C14 1.870(4) . ?
S2 C11 1.737(4) . ?
S2 C14 1.737(5) . ?
S1 C9 1.721(6) . ?
S1 C10 1.739(4) . ?
N1 C7 1.395(5) . ?
N1 B1 1.444(5) . ?
N1 C4 1.451(5) . ?
C15 C20 1.392(5) . ?
C15 C16 1.400(5) . ?
C15 B1 1.579(5) . ?
C4 C3 1.384(5) . ?
C4 C5 1.384(6) . ?
C3 C2 1.389(5) . ?
C3 H3 0.9300 . ?
C12 C11 1.403(5) . ?
C12 C13 1.435(6) . ?
C12 B1 1.523(6) . ?
C11 C10 1.412(6) . ?
C7 C10 1.389(5) . ?
C7 C8 1.438(6) . ?
C1 C6 1.378(6) . ?
C1 C2 1.381(6) . ?
C2 H2 0.9300 . ?
C20 C19 1.385(6) . ?
C20 H20 0.9300 . ?
C16 C17 1.384(6) . ?
C16 H16 0.9300 . ?
C5 C6 1.387(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C13 C14 1.356(6) . ?
C13 H13 0.9300 . ?
C19 C18 1.395(7) . ?
C19 H19 0.9300 . ?
C18 C17 1.367(7) . ?
C18 H18 0.9300 . ?
C8 C9 1.358(6) . ?
C8 H8 0.9300 . ?
C17 H17 0.9300 . ?
C9 H9 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
C11 S2 C14 90.4(2) . . ?
C9 S1 C10 91.3(2) . . ?
C7 N1 B1 122.3(3) . . ?
C7 N1 C4 115.8(3) . . ?
B1 N1 C4 121.9(3) . . ?
C20 C15 C16 117.4(3) . . ?
C20 C15 B1 122.7(3) . . ?
C16 C15 B1 119.9(3) . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 N1 118.5(3) . . ?
C5 C4 N1 121.2(3) . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C11 C12 C13 111.0(3) . . ?
C11 C12 B1 119.0(4) . . ?
C13 C12 B1 129.9(4) . . ?
C12 C11 C10 121.3(3) . . ?
C12 C11 S2 112.4(3) . . ?
C10 C11 S2 126.3(3) . . ?
C10 C7 N1 120.8(3) . . ?
C10 C7 C8 112.6(3) . . ?
N1 C7 C8 126.5(4) . . ?
C6 C1 C2 121.5(4) . . ?
C6 C1 Br1 120.2(3) . . ?
C2 C1 Br1 118.3(3) . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C19 C20 C15 121.7(4) . . ?
C19 C20 H20 119.2 . . ?
C15 C20 H20 119.2 . . ?
C7 C10 C11 120.9(3) . . ?
C7 C10 S1 110.9(3) . . ?
C11 C10 S1 128.1(3) . . ?
C17 C16 C15 121.2(4) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.0(4) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C14 C13 C12 112.9(4) . . ?
C14 C13 H13 123.5 . . ?
C12 C13 H13 123.5 . . ?
C20 C19 C18 119.4(4) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C17 C18 C19 119.9(4) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C13 C14 S2 113.3(3) . . ?
C13 C14 Br2 127.4(4) . . ?
S2 C14 Br2 119.2(2) . . ?
C9 C8 C7 111.7(4) . . ?
C9 C8 H8 124.2 . . ?
C7 C8 H8 124.2 . . ?
C18 C17 C16 120.4(4) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
N1 B1 C12 115.6(3) . . ?
N1 B1 C15 121.4(3) . . ?
C12 B1 C15 123.0(3) . . ?
C8 C9 S1 113.4(4) . . ?
C8 C9 H9 123.3 . . ?
S1 C9 H9 123.3 . . ?

_refine_diff_density_max         0.918
_refine_diff_density_min         -0.971
_refine_diff_density_rms         0.085

_shelxl_version_number           2013-4

