# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_B200728A_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2034492'
loop_
_audit_author_name
_audit_author_address
aa
;SOOCHOW University
China
;
_audit_update_record             
;
2020-09-29 deposited with the CCDC.	2021-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H32 Br2 N6 O4 S2'
_chemical_formula_sum            'C36 H32 Br2 N6 O4 S2'
_chemical_formula_weight         836.61

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'
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'
Br Br -0.2901 2.4595 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.138(3)
_cell_length_b                   10.099(2)
_cell_length_c                   22.516(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3442.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3271
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.79

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   0.2833
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.527
_shelx_estimated_absorpt_T_min   0.365
_shelx_estimated_absorpt_T_max   0.632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11546
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.588
_diffrn_reflns_theta_max         27.986
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4100
_reflns_number_gt                2406
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4100
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1881
_refine_ls_wR_factor_gt          0.1415
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.32279(4) 0.13744(6) 0.48191(3) 0.0689(3) Uani 1 1 d . . . . .
S1 S 0.64093(7) 0.38189(10) 0.63042(5) 0.0356(3) Uani 1 1 d . . . . .
O1 O 0.6723(2) 0.4958(3) 0.59843(14) 0.0490(8) Uani 1 1 d . . . . .
O2 O 0.7019(2) 0.2774(3) 0.64074(15) 0.0529(8) Uani 1 1 d . . . . .
N1 N 0.5941(2) 0.4200(3) 0.69230(16) 0.0358(8) Uani 1 1 d . . . . .
N2 N 0.6728(2) 0.6215(3) 0.70888(18) 0.0375(8) Uani 1 1 d . . . . .
H2A H 0.704(3) 0.622(4) 0.676(2) 0.045 Uiso 1 1 d . U . . .
N3 N 0.4547(2) 0.4281(3) 0.81608(17) 0.0415(9) Uani 1 1 d . . . . .
C1 C 0.4152(3) 0.2104(5) 0.52701(19) 0.0446(11) Uani 1 1 d . . . . .
C2 C 0.4208(3) 0.3458(5) 0.5337(2) 0.0486(12) Uani 1 1 d . . . . .
H2 H 0.3787 0.4011 0.5167 0.058 Uiso 1 1 calc R U . . .
C3 C 0.4896(3) 0.3972(4) 0.5657(2) 0.0428(10) Uani 1 1 d . . . . .
H3 H 0.4940 0.4883 0.5710 0.051 Uiso 1 1 calc R U . . .
C4 C 0.5523(3) 0.3148(4) 0.59025(18) 0.0345(9) Uani 1 1 d . . . . .
C5 C 0.5465(3) 0.1797(4) 0.58314(19) 0.0381(10) Uani 1 1 d . . . . .
H5 H 0.5890 0.1241 0.5995 0.046 Uiso 1 1 calc R U . . .
C6 C 0.4764(3) 0.1281(4) 0.5512(2) 0.0426(10) Uani 1 1 d . . . . .
H6 H 0.4713 0.0370 0.5463 0.051 Uiso 1 1 calc R U . . .
C7 C 0.6168(2) 0.5258(4) 0.72125(18) 0.0307(8) Uani 1 1 d . . . . .
C8 C 0.6806(2) 0.7234(4) 0.7541(2) 0.0402(10) Uani 1 1 d . . . . .
H8A H 0.6783 0.8112 0.7367 0.048 Uiso 1 1 calc R U . . .
H8B H 0.7352 0.7141 0.7763 0.048 Uiso 1 1 calc R U . . .
C9 C 0.6013(3) 0.6984(4) 0.7933(2) 0.0401(10) Uani 1 1 d . . . . .
H9A H 0.5530 0.7569 0.7827 0.048 Uiso 1 1 calc R U . . .
H9B H 0.6161 0.7124 0.8347 0.048 Uiso 1 1 calc R U . . .
C10 C 0.5760(2) 0.5522(3) 0.78202(18) 0.0310(8) Uani 1 1 d . . . . .
C11 C 0.4773(3) 0.5214(4) 0.78109(19) 0.0352(9) Uani 1 1 d . . . . .
C12 C 0.5321(3) 0.3841(4) 0.8455(2) 0.0376(10) Uani 1 1 d . . . . .
C13 C 0.5358(4) 0.2884(4) 0.8888(2) 0.0530(12) Uani 1 1 d . . . . .
H13 H 0.4855 0.2430 0.9009 0.064 Uiso 1 1 calc R U . . .
C14 C 0.6167(4) 0.2627(5) 0.9134(2) 0.0649(15) Uani 1 1 d . . . . .
H14 H 0.6218 0.1980 0.9426 0.078 Uiso 1 1 calc R U . . .
C15 C 0.6904(4) 0.3312(6) 0.8957(3) 0.0621(14) Uani 1 1 d . . . . .
H15 H 0.7446 0.3119 0.9131 0.075 Uiso 1 1 calc R U . . .
C16 C 0.6860(3) 0.4280(5) 0.8525(2) 0.0497(11) Uani 1 1 d . . . . .
H16 H 0.7361 0.4747 0.8410 0.060 Uiso 1 1 calc R U . . .
C17 C 0.6062(3) 0.4531(4) 0.82723(18) 0.0368(9) Uani 1 1 d . . . . .
C18 C 0.4142(3) 0.5897(5) 0.7418(2) 0.0496(12) Uani 1 1 d . . . . .
H18A H 0.3556 0.5574 0.7494 0.074 Uiso 1 1 calc R U . . .
H18B H 0.4295 0.5730 0.7011 0.074 Uiso 1 1 calc R U . . .
H18C H 0.4162 0.6832 0.7493 0.074 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 1.879(4) . ?
S1 O2 1.421(3) . ?
S1 O1 1.438(3) . ?
S1 N1 1.610(4) . ?
S1 C4 1.755(4) . ?
N1 C7 1.297(5) . ?
N2 C7 1.315(5) . ?
N2 C8 1.453(6) . ?
N2 H2A 0.87(5) . ?
N3 C11 1.275(5) . ?
N3 C12 1.418(6) . ?
C1 C6 1.359(6) . ?
C1 C2 1.378(7) . ?
C2 C3 1.369(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(6) . ?
C5 C6 1.383(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C10 1.525(6) . ?
C8 C9 1.510(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.547(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C17 1.499(5) . ?
C10 C11 1.526(5) . ?
C11 C18 1.474(6) . ?
C12 C13 1.375(6) . ?
C12 C17 1.382(6) . ?
C13 C14 1.369(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.359(6) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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 O1 117.5(2) . . ?
O2 S1 N1 108.8(2) . . ?
O1 S1 N1 112.79(18) . . ?
O2 S1 C4 107.13(19) . . ?
O1 S1 C4 107.65(19) . . ?
N1 S1 C4 101.64(18) . . ?
C7 N1 S1 121.0(3) . . ?
C7 N2 C8 115.1(4) . . ?
C7 N2 H2A 122(3) . . ?
C8 N2 H2A 123(3) . . ?
C11 N3 C12 107.3(3) . . ?
C6 C1 C2 121.4(4) . . ?
C6 C1 Br1 119.0(4) . . ?
C2 C1 Br1 119.6(4) . . ?
C3 C2 C1 118.7(4) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 S1 119.4(3) . . ?
C3 C4 S1 120.0(3) . . ?
C4 C5 C6 118.8(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 120.1(4) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
N1 C7 N2 132.0(4) . . ?
N1 C7 C10 119.2(3) . . ?
N2 C7 C10 108.8(3) . . ?
N2 C8 C9 103.1(3) . . ?
N2 C8 H8A 111.2 . . ?
C9 C8 H8A 111.2 . . ?
N2 C8 H8B 111.2 . . ?
C9 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C8 C9 C10 105.1(3) . . ?
C8 C9 H9A 110.7 . . ?
C10 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
C10 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C17 C10 C7 111.7(3) . . ?
C17 C10 C11 99.9(3) . . ?
C7 C10 C11 110.4(3) . . ?
C17 C10 C9 116.8(3) . . ?
C7 C10 C9 102.4(3) . . ?
C11 C10 C9 116.0(3) . . ?
N3 C11 C18 122.8(4) . . ?
N3 C11 C10 113.9(4) . . ?
C18 C11 C10 123.3(4) . . ?
C13 C12 C17 122.2(4) . . ?
C13 C12 N3 125.8(4) . . ?
C17 C12 N3 112.0(4) . . ?
C14 C13 C12 117.2(5) . . ?
C14 C13 H13 121.4 . . ?
C12 C13 H13 121.4 . . ?
C13 C14 C15 120.9(5) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C16 121.5(5) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 118.0(5) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C16 C17 C12 120.2(4) . . ?
C16 C17 C10 132.8(4) . . ?
C12 C17 C10 106.9(4) . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.968
_refine_diff_density_min         -0.948
_refine_diff_density_rms         0.101

