# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_2
_database_code_depnum_ccdc_archive 'CCDC 2012543'
loop_
_audit_author_name
_audit_author_address
'wenyao wang'
;Dalian University of Technology
China
;
_audit_update_record             
;
2020-06-27 deposited with the CCDC.	2021-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H18 Br N3 O2 S'
_chemical_formula_weight         516.40

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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   10.235(2)
_cell_length_b                   10.235(2)
_cell_length_c                   23.295(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2440.4(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1796
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      18.42

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    1.797
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7264
_exptl_absorpt_correction_T_max  0.8132
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12748
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_sigmaI/netI    0.1143
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4217
_reflns_number_gt                2677
_reflns_threshold_expression     >2sigma(I)

_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'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_chemical_absolute_configuration s
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.027(12)
_refine_ls_number_reflns         4217
_refine_ls_number_parameters     298
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.951
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.48705(7) 0.10887(7) 0.21419(5) 0.1041(3) Uani 1 1 d . . .
S2 S 0.19904(14) 0.46219(18) 0.17529(7) 0.0740(5) Uani 1 1 d . . .
C1 C 0.2321(4) 0.6165(5) 0.4838(2) 0.0462(12) Uani 1 1 d . . .
C2 C 0.6175(4) 0.3411(4) 0.24975(19) 0.0399(11) Uani 1 1 d . . .
C3 C 0.3842(4) 0.4222(4) 0.2636(2) 0.0413(11) Uani 1 1 d . . .
O1 O 0.5027(4) 0.4620(4) 0.17826(18) 0.0741(11) Uani 1 1 d . . .
N2 N 0.1915(4) 0.4064(4) 0.43790(18) 0.0505(10) Uani 1 1 d . . .
C6 C 0.2559(5) 0.5743(6) 0.3764(2) 0.0523(14) Uani 1 1 d . . .
C7 C 0.5001(4) 0.4100(5) 0.2258(2) 0.0446(11) Uani 1 1 d . . .
C8 C 0.2507(5) 0.4442(5) 0.3419(2) 0.0468(12) Uani 1 1 d . . .
C9 C 0.1601(5) 0.2152(5) 0.3797(2) 0.0504(13) Uani 1 1 d . . .
C10 C 0.2466(6) 0.7638(7) 0.5833(3) 0.0770(19) Uani 1 1 d . . .
H10A H 0.2514 0.8134 0.6167 0.092 Uiso 1 1 calc R . .
N1 N 0.2261(4) 0.5401(4) 0.43292(17) 0.0461(10) Uani 1 1 d . . .
N3 N 0.1684(4) 0.4588(4) 0.29045(17) 0.0515(10) Uani 1 1 d . . .
C13 C 0.6233(5) 0.2059(5) 0.2478(2) 0.0564(14) Uani 1 1 d . . .
C14 C 0.2414(5) 0.5549(6) 0.5359(2) 0.0549(13) Uani 1 1 d . . .
H14A H 0.2427 0.4642 0.5378 0.066 Uiso 1 1 calc R . .
C15 C 0.1990(5) 0.3516(5) 0.3887(2) 0.0480(12) Uani 1 1 d . . .
O2 O 0.2826(4) 0.6819(4) 0.35887(18) 0.0714(11) Uani 1 1 d . . .
C17 C 0.2460(5) 0.4499(5) 0.2470(2) 0.0462(12) Uani 1 1 d . . .
C18 C 0.2321(5) 0.7514(6) 0.4805(2) 0.0624(15) Uani 1 1 d . . .
H18A H 0.2287 0.7933 0.4451 0.075 Uiso 1 1 calc R . .
C20 C 0.2488(6) 0.6287(7) 0.5863(3) 0.0678(16) Uani 1 1 d . . .
H20A H 0.2552 0.5872 0.6217 0.081 Uiso 1 1 calc R . .
C21 C 0.3853(4) 0.4150(4) 0.3206(2) 0.0428(11) Uani 1 1 d . . .
H21A H 0.4575 0.3952 0.3432 0.051 Uiso 1 1 calc R . .
C22 C 0.8289(7) 0.2092(8) 0.2946(3) 0.091(2) Uani 1 1 d . . .
H22A H 0.9013 0.1653 0.3091 0.109 Uiso 1 1 calc R . .
C23 C 0.7187(5) 0.4087(5) 0.2743(2) 0.0578(14) Uani 1 1 d . . .
H23A H 0.7164 0.4995 0.2754 0.069 Uiso 1 1 calc R . .
C24 C 0.2373(6) 0.8234(6) 0.5313(3) 0.0744(17) Uani 1 1 d . . .
H24A H 0.2344 0.9141 0.5296 0.089 Uiso 1 1 calc R . .
C26 C 0.7306(7) 0.1398(6) 0.2710(3) 0.0816(19) Uani 1 1 d . . .
H26A H 0.7341 0.0490 0.2703 0.098 Uiso 1 1 calc R . .
C27 C 0.8248(6) 0.3422(7) 0.2976(3) 0.0786(18) Uani 1 1 d . . .
H27A H 0.8924 0.3882 0.3151 0.094 Uiso 1 1 calc R . .
C102 C 0.2101(6) 0.1384(6) 0.3359(3) 0.0708(17) Uani 1 1 d . . .
H10B H 0.2678 0.1749 0.3096 0.085 Uiso 1 1 calc R . .
C202 C 0.0869(7) -0.0462(6) 0.3690(3) 0.0806(19) Uani 1 1 d . . .
H20B H 0.0632 -0.1336 0.3660 0.097 Uiso 1 1 calc R . .
C302 C 0.0712(6) 0.1592(6) 0.4171(3) 0.0752(18) Uani 1 1 d . . .
H30A H 0.0355 0.2091 0.4465 0.090 Uiso 1 1 calc R . .
C402 C 0.1753(8) 0.0082(7) 0.3308(3) 0.085(2) Uani 1 1 d . . .
H40A H 0.2113 -0.0427 0.3017 0.102 Uiso 1 1 calc R . .
C502 C 0.0351(7) 0.0305(7) 0.4111(4) 0.089(2) Uani 1 1 d . . .
H50A H -0.0259 -0.0050 0.4363 0.107 Uiso 1 1 calc R . .
C602 C 0.0266(6) 0.4939(11) 0.1828(3) 0.127(3) Uani 1 1 d . . .
H60A H -0.0120 0.5032 0.1454 0.190 Uiso 1 1 calc R . .
H60B H 0.0140 0.5730 0.2042 0.190 Uiso 1 1 calc R . .
H60C H -0.0140 0.4224 0.2026 0.190 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 C13 1.883(5) . ?
S2 C17 1.743(5) . ?
S2 C602 1.803(7) . ?
C1 C14 1.371(7) . ?
C1 C18 1.383(7) . ?
C1 N1 1.422(6) . ?
C2 C23 1.371(7) . ?
C2 C13 1.385(7) . ?
C2 C7 1.501(6) . ?
C3 C21 1.330(7) . ?
C3 C7 1.482(7) . ?
C3 C17 1.494(6) . ?
O1 C7 1.228(6) . ?
N2 C15 1.279(6) . ?
N2 N1 1.418(5) . ?
C6 O2 1.207(6) . ?
C6 N1 1.396(7) . ?
C6 C8 1.557(7) . ?
C8 N3 1.473(6) . ?
C8 C21 1.495(6) . ?
C8 C15 1.537(7) . ?
C9 C302 1.383(8) . ?
C9 C102 1.387(8) . ?
C9 C15 1.466(7) . ?
C10 C24 1.360(9) . ?
C10 C20 1.384(9) . ?
N3 C17 1.289(6) . ?
C13 C26 1.399(8) . ?
C14 C20 1.396(8) . ?
C18 C24 1.396(8) . ?
C22 C26 1.349(9) . ?
C22 C27 1.364(9) . ?
C23 C27 1.392(8) . ?
C102 C402 1.385(8) . ?
C202 C502 1.363(10) . ?
C202 C402 1.387(9) . ?
C302 C502 1.376(8) . ?

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
C17 S2 C602 101.0(3) . . ?
C14 C1 C18 120.6(5) . . ?
C14 C1 N1 119.2(5) . . ?
C18 C1 N1 120.2(4) . . ?
C23 C2 C13 119.0(5) . . ?
C23 C2 C7 121.5(4) . . ?
C13 C2 C7 119.4(4) . . ?
C21 C3 C7 125.6(4) . . ?
C21 C3 C17 106.0(4) . . ?
C7 C3 C17 128.4(4) . . ?
C15 N2 N1 109.6(4) . . ?
O2 C6 N1 126.8(5) . . ?
O2 C6 C8 127.9(5) . . ?
N1 C6 C8 105.4(4) . . ?
O1 C7 C3 121.1(4) . . ?
O1 C7 C2 121.4(4) . . ?
C3 C7 C2 117.3(4) . . ?
N3 C8 C21 106.1(4) . . ?
N3 C8 C15 116.3(4) . . ?
C21 C8 C15 115.5(4) . . ?
N3 C8 C6 110.7(4) . . ?
C21 C8 C6 108.1(4) . . ?
C15 C8 C6 100.0(4) . . ?
C302 C9 C102 118.1(5) . . ?
C302 C9 C15 119.0(5) . . ?
C102 C9 C15 122.9(5) . . ?
C24 C10 C20 119.5(6) . . ?
C6 N1 N2 112.0(4) . . ?
C6 N1 C1 129.7(4) . . ?
N2 N1 C1 118.3(4) . . ?
C17 N3 C8 106.2(4) . . ?
C2 C13 C26 120.3(5) . . ?
C2 C13 Br1 120.6(4) . . ?
C26 C13 Br1 119.2(4) . . ?
C1 C14 C20 119.9(5) . . ?
N2 C15 C9 121.9(5) . . ?
N2 C15 C8 112.7(4) . . ?
C9 C15 C8 125.4(4) . . ?
N3 C17 C3 113.2(4) . . ?
N3 C17 S2 125.2(4) . . ?
C3 C17 S2 121.5(4) . . ?
C1 C18 C24 118.6(5) . . ?
C10 C20 C14 119.9(6) . . ?
C3 C21 C8 108.3(4) . . ?
C26 C22 C27 121.6(6) . . ?
C2 C23 C27 120.4(5) . . ?
C10 C24 C18 121.5(6) . . ?
C22 C26 C13 119.2(6) . . ?
C22 C27 C23 119.5(6) . . ?
C9 C102 C402 120.9(6) . . ?
C502 C202 C402 119.0(6) . . ?
C502 C302 C9 120.7(6) . . ?
C102 C402 C202 119.9(6) . . ?
C202 C502 C302 121.3(7) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.042
