# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1996508'
loop_
_audit_author_name
_audit_author_address
'Wei Shiqiang'
;Dalian Linggongroad  
China
;
_audit_update_record             
;
2020-04-13 deposited with the CCDC.	2020-08-05 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         ?
_chemical_formula_sum            'C36 H29 Br N4 O4 S'
_chemical_formula_weight         693.60

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   10.4627(13)
_cell_length_b                   10.6763(14)
_cell_length_c                   29.015(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3241.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5582
_cell_measurement_theta_min      2.3674
_cell_measurement_theta_max      24.7135

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   0.5742
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    1.379
_shelx_estimated_absorpt_T_min   0.667
_shelx_estimated_absorpt_T_max   0.733
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17760
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.033
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5728
_reflns_number_gt                4930
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0200P)²+2.5524P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    'riding mode'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1857 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5728
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0720
_refine_ls_wR_factor_gt          0.0689
_refine_ls_goodness_of_fit_ref   0.829
_refine_ls_restrained_S_all      0.829
_refine_ls_shift/su_max          0.001
_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 0.84813(4) 0.05703(5) 0.96517(2) 0.05803(16) Uani 1 1 d . . . . .
S2 S 0.40173(10) 0.33223(9) 0.89917(3) 0.0350(2) Uani 1 1 d . . . . .
C1 C 0.4598(3) 0.0676(3) 0.94288(12) 0.0249(8) Uani 1 1 d . . . . .
N3 N 0.3461(3) -0.0562(3) 0.75064(10) 0.0358(7) Uani 1 1 d . . . . .
C3 C 0.3536(3) 0.0740(3) 0.90778(11) 0.0250(7) Uani 1 1 d . . . . .
C4 C 0.6682(3) 0.0627(3) 0.97488(13) 0.0339(9) Uani 1 1 d . . . . .
N2 N 0.3618(3) 0.1647(3) 0.83196(10) 0.0288(7) Uani 1 1 d . . . . .
O4 O 0.0986(3) 0.0486(3) 0.82078(9) 0.0527(8) Uani 1 1 d . . . . .
N1 N 0.2762(3) 0.0988(3) 0.98408(10) 0.0278(7) Uani 1 1 d . . . . .
O3 O 0.2428(3) -0.1720(3) 0.92196(9) 0.0456(7) Uani 1 1 d . . . . .
C9 C 0.3341(4) 0.0311(3) 0.82442(11) 0.0288(8) Uani 1 1 d . . . . .
C10 C 0.1227(4) -0.0495(4) 0.72554(12) 0.0345(9) Uani 1 1 d . . . . .
O1 O 0.1236(2) 0.0989(3) 0.92693(9) 0.0430(7) Uani 1 1 d . . . . .
N4 N 0.2182(3) -0.0234(3) 0.75952(10) 0.0350(8) Uani 1 1 d . . . . .
C13 C 0.5900(3) 0.0557(4) 0.93647(13) 0.0306(8) Uani 1 1 d . . . . .
H13A H 0.6241 0.0433 0.9072 0.037 Uiso 1 1 calc R U . . .
C14 C 0.3684(3) 0.1857(3) 0.87530(12) 0.0255(8) Uani 1 1 d . . . . .
C15 C 0.3514(4) -0.0336(3) 0.87214(11) 0.0287(8) Uani 1 1 d . . . . .
H15A H 0.4390 -0.0661 0.8718 0.034 Uiso 1 1 calc R U . . .
C16 C 0.4095(3) 0.0864(3) 0.98706(12) 0.0277(8) Uani 1 1 d . . . . .
C17 C 0.2335(3) 0.0907(3) 0.93929(12) 0.0270(8) Uani 1 1 d . . . . .
C18 C 0.1776(3) -0.0013(3) 1.05273(12) 0.0303(9) Uani 1 1 d . . . . .
C19 C 0.4877(4) 0.0929(4) 1.02497(13) 0.0353(9) Uani 1 1 d . . . . .
H19A H 0.4539 0.1045 1.0543 0.042 Uiso 1 1 calc R U . . .
C20 C 0.4133(4) -0.0254(3) 0.78603(12) 0.0298(8) Uani 1 1 d . . . . .
C21 C 0.1281(4) -0.1593(4) 0.70057(14) 0.0457(11) Uani 1 1 d . . . . .
H21A H 0.1929 -0.2171 0.7060 0.055 Uiso 1 1 calc R U . . .
C22 C 0.1916(4) 0.1156(3) 1.02405(12) 0.0315(9) Uani 1 1 d . . . . .
H22A H 0.1078 0.1413 1.0133 0.038 Uiso 1 1 calc R U . . .
H22B H 0.2252 0.1822 1.0433 0.038 Uiso 1 1 calc R U . . .
C23 C 0.5514(3) -0.0521(4) 0.78828(11) 0.0318(8) Uani 1 1 d . . . . .
C24 C 0.1988(4) 0.0203(4) 0.80330(13) 0.0329(9) Uani 1 1 d . . . . .
C25 C 0.2685(4) -0.1471(4) 0.87827(14) 0.0384(10) Uani 1 1 d . . . . .
C26 C 0.2210(5) -0.0070(4) 1.09762(14) 0.0475(11) Uani 1 1 d . . . . .
H26A H 0.2607 0.0625 1.1106 0.057 Uiso 1 1 calc R U . . .
C27 C -0.0590(5) -0.0979(5) 0.65955(16) 0.0577(14) Uani 1 1 d . . . . .
H27A H -0.1205 -0.1142 0.6372 0.069 Uiso 1 1 calc R U . . .
C28 C 0.5991(4) -0.1618(4) 0.76939(13) 0.0412(10) Uani 1 1 d . . . . .
H28A H 0.5440 -0.2171 0.7546 0.049 Uiso 1 1 calc R U . . .
C29 C 0.6358(4) 0.0293(4) 0.80984(14) 0.0423(10) Uani 1 1 d . . . . .
H29A H 0.6057 0.1041 0.8221 0.051 Uiso 1 1 calc R U . . .
C30 C 0.7283(4) -0.1898(5) 0.77235(15) 0.0506(12) Uani 1 1 d . . . . .
H30A H 0.7593 -0.2634 0.7593 0.061 Uiso 1 1 calc R U . . .
C31 C 0.6193(4) 0.0817(4) 1.01838(13) 0.0382(10) Uani 1 1 d . . . . .
H31A H 0.6743 0.0872 1.0435 0.046 Uiso 1 1 calc R U . . .
C32 C 0.0267(4) 0.0366(4) 0.71778(14) 0.0430(10) Uani 1 1 d . . . . .
H32A H 0.0234 0.1106 0.7346 0.052 Uiso 1 1 calc R U . . .
C33 C 0.8106(4) -0.1098(5) 0.79436(15) 0.0501(12) Uani 1 1 d . . . . .
H33A H 0.8969 -0.1296 0.7966 0.060 Uiso 1 1 calc R U . . .
C34 C 0.1677(6) -0.2860(4) 0.93049(18) 0.0635(15) Uani 1 1 d . . . . .
H34A H 0.1785 -0.3115 0.9623 0.076 Uiso 1 1 calc R U . . .
H34B H 0.1993 -0.3530 0.9110 0.076 Uiso 1 1 calc R U . . .
O2 O 0.2369(4) -0.2115(3) 0.84628(11) 0.0687(11) Uani 1 1 d . . . . .
C36 C 0.4183(5) 0.4276(4) 0.84848(14) 0.0488(11) Uani 1 1 d . . . . .
H36A H 0.4372 0.5122 0.8574 0.073 Uiso 1 1 calc R U . . .
H36B H 0.4866 0.3956 0.8298 0.073 Uiso 1 1 calc R U . . .
H36C H 0.3400 0.4259 0.8312 0.073 Uiso 1 1 calc R U . . .
C38 C 0.1024(6) -0.2132(5) 1.06120(18) 0.0721(17) Uani 1 1 d . . . . .
H38A H 0.0619 -0.2831 1.0488 0.087 Uiso 1 1 calc R U . . .
C39 C 0.7653(4) 0.0001(4) 0.81324(16) 0.0514(12) Uani 1 1 d . . . . .
H39A H 0.8209 0.0545 0.8282 0.062 Uiso 1 1 calc R U . . .
C40 C -0.0648(4) 0.0111(5) 0.68448(15) 0.0542(13) Uani 1 1 d . . . . .
H40A H -0.1303 0.0681 0.6790 0.065 Uiso 1 1 calc R U . . .
C41 C 0.2061(5) -0.1147(5) 1.12341(16) 0.0613(14) Uani 1 1 d . . . . .
H41A H 0.2356 -0.1168 1.1536 0.074 Uiso 1 1 calc R U . . .
C42 C 0.1495(6) -0.2164(5) 1.10547(17) 0.0623(14) Uani 1 1 d . . . . .
H42A H 0.1421 -0.2891 1.1230 0.075 Uiso 1 1 calc R U . . .
C45 C 0.0363(5) -0.1826(5) 0.66732(15) 0.0543(13) Uani 1 1 d . . . . .
H45A H 0.0395 -0.2563 0.6502 0.065 Uiso 1 1 calc R U . . .
C47 C 0.1156(5) -0.1052(4) 1.03512(17) 0.0578(13) Uani 1 1 d . . . . .
H47A H 0.0824 -0.1025 1.0054 0.069 Uiso 1 1 calc R U . . .
C201 C 0.0293(6) -0.2657(6) 0.9210(2) 0.0813(19) Uani 1 1 d . . . . .
H20A H -0.0169 -0.3418 0.9269 0.122 Uiso 1 1 calc R U . . .
H20B H -0.0026 -0.2004 0.9406 0.122 Uiso 1 1 calc R U . . .
H20C H 0.0182 -0.2420 0.8893 0.122 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 C4 1.904(4) . ?
S2 C14 1.746(4) . ?
S2 C36 1.797(4) . ?
C1 C13 1.381(5) . ?
C1 C16 1.400(5) . ?
C1 C3 1.508(5) . ?
N3 C20 1.287(4) . ?
N3 N4 1.406(4) . ?
C3 C14 1.528(5) . ?
C3 C15 1.546(5) . ?
C3 C17 1.565(5) . ?
C4 C31 1.377(5) . ?
C4 C13 1.385(5) . ?
N2 C14 1.279(4) . ?
N2 C9 1.472(5) . ?
O4 C24 1.204(5) . ?
N1 C17 1.377(5) . ?
N1 C16 1.404(4) . ?
N1 C22 1.470(4) . ?
O3 C25 1.323(5) . ?
O3 C34 1.469(5) . ?
C9 C20 1.514(5) . ?
C9 C24 1.547(5) . ?
C9 C15 1.558(5) . ?
C10 C21 1.379(6) . ?
C10 C32 1.380(6) . ?
C10 N4 1.431(5) . ?
O1 C17 1.207(4) . ?
N4 C24 1.368(5) . ?
C15 C25 1.501(5) . ?
C16 C19 1.373(5) . ?
C18 C47 1.382(6) . ?
C18 C26 1.381(5) . ?
C18 C22 1.507(5) . ?
C19 C31 1.395(6) . ?
C20 C23 1.474(5) . ?
C21 C45 1.384(6) . ?
C23 C29 1.388(6) . ?
C23 C28 1.386(6) . ?
C25 O2 1.201(5) . ?
C26 C41 1.381(6) . ?
C27 C45 1.365(7) . ?
C27 C40 1.371(7) . ?
C28 C30 1.387(6) . ?
C29 C39 1.393(6) . ?
C30 C33 1.371(7) . ?
C32 C40 1.387(6) . ?
C33 C39 1.378(6) . ?
C34 C201 1.490(8) . ?
C38 C42 1.376(7) . ?
C38 C47 1.387(7) . ?
C41 C42 1.342(7) . ?

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
C14 S2 C36 101.66(19) . . ?
C13 C1 C16 120.5(3) . . ?
C13 C1 C3 129.7(3) . . ?
C16 C1 C3 109.6(3) . . ?
C20 N3 N4 108.0(3) . . ?
C1 C3 C14 112.2(3) . . ?
C1 C3 C15 115.4(3) . . ?
C14 C3 C15 99.7(2) . . ?
C1 C3 C17 101.7(3) . . ?
C14 C3 C17 110.7(3) . . ?
C15 C3 C17 117.6(3) . . ?
C31 C4 C13 121.7(3) . . ?
C31 C4 Br1 120.5(3) . . ?
C13 C4 Br1 117.6(3) . . ?
C14 N2 C9 109.0(3) . . ?
C17 N1 C16 112.0(3) . . ?
C17 N1 C22 123.8(3) . . ?
C16 N1 C22 124.1(3) . . ?
C25 O3 C34 115.9(3) . . ?
N2 C9 C20 112.8(3) . . ?
N2 C9 C24 108.1(3) . . ?
C20 C9 C24 100.4(3) . . ?
N2 C9 C15 106.0(3) . . ?
C20 C9 C15 114.5(3) . . ?
C24 C9 C15 115.2(3) . . ?
C21 C10 C32 120.7(4) . . ?
C21 C10 N4 119.9(4) . . ?
C32 C10 N4 119.4(4) . . ?
C24 N4 N3 113.3(3) . . ?
C24 N4 C10 127.0(3) . . ?
N3 N4 C10 119.3(3) . . ?
C1 C13 C4 118.0(3) . . ?
N2 C14 C3 117.6(3) . . ?
N2 C14 S2 123.9(3) . . ?
C3 C14 S2 118.4(2) . . ?
C25 C15 C3 122.0(3) . . ?
C25 C15 C9 113.3(3) . . ?
C3 C15 C9 105.5(3) . . ?
C19 C16 C1 121.1(3) . . ?
C19 C16 N1 129.6(3) . . ?
C1 C16 N1 109.3(3) . . ?
O1 C17 N1 125.8(3) . . ?
O1 C17 C3 126.9(3) . . ?
N1 C17 C3 107.3(3) . . ?
C47 C18 C26 117.9(4) . . ?
C47 C18 C22 120.4(3) . . ?
C26 C18 C22 121.7(4) . . ?
C16 C19 C31 118.3(4) . . ?
N3 C20 C23 121.4(3) . . ?
N3 C20 C9 112.9(3) . . ?
C23 C20 C9 125.5(3) . . ?
C10 C21 C45 119.4(4) . . ?
N1 C22 C18 113.1(3) . . ?
C29 C23 C28 118.6(4) . . ?
C29 C23 C20 121.5(4) . . ?
C28 C23 C20 119.9(4) . . ?
O4 C24 N4 127.3(4) . . ?
O4 C24 C9 127.7(3) . . ?
N4 C24 C9 104.9(3) . . ?
O2 C25 O3 124.7(4) . . ?
O2 C25 C15 122.0(4) . . ?
O3 C25 C15 113.2(3) . . ?
C41 C26 C18 120.7(4) . . ?
C45 C27 C40 120.5(4) . . ?
C30 C28 C23 120.6(4) . . ?
C23 C29 C39 120.7(4) . . ?
C33 C30 C28 120.4(4) . . ?
C4 C31 C19 120.3(3) . . ?
C10 C32 C40 119.0(4) . . ?
C30 C33 C39 120.0(4) . . ?
O3 C34 C201 111.6(4) . . ?
C42 C38 C47 119.6(5) . . ?
C29 C39 C33 119.8(4) . . ?
C27 C40 C32 120.2(5) . . ?
C42 C41 C26 120.9(4) . . ?
C41 C42 C38 120.0(4) . . ?
C27 C45 C21 120.2(5) . . ?
C38 C47 C18 120.8(4) . . ?

_refine_diff_density_max         0.580
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.043



