# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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 1967156'
loop_
_audit_author_name
_audit_author_address
'TT Liu'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2019-11-21 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 Br N O3 S'
_chemical_formula_weight         446.35

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

_cell_length_a                   5.9222(17)
_cell_length_b                   13.176(4)
_cell_length_c                   26.122(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2038.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2523
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      20.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.140
_shelx_estimated_absorpt_T_min   0.617
_shelx_estimated_absorpt_T_max   0.674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.617
_exptl_absorpt_correction_T_max  0.674
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            10309
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.196
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3570
_reflns_number_gt                2720
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0300P)²+0.0258P] 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_abs_structure_details 
; 
 Flack x determined using 869 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.021(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3570
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 1.30252(13) 0.20694(6) 0.37769(2) 0.0563(2) Uani 1 1 d . . . . .
C1 C 0.9429(10) 0.0522(5) 0.0940(2) 0.0364(15) Uani 1 1 d . . . . .
H1 H 1.100796 0.038555 0.085154 0.044 Uiso 1 1 calc R U . . .
C2 C 0.8934(12) 0.1637(5) 0.0857(2) 0.0401(17) Uani 1 1 d . . . . .
C3 C 0.6940(14) 0.2084(6) 0.1013(2) 0.0561(17) Uani 1 1 d . . . . .
H3 H 0.586206 0.170860 0.118937 0.067 Uiso 1 1 calc R U . . .
C4 C 0.6565(17) 0.3090(7) 0.0903(3) 0.077(3) Uani 1 1 d . . . . .
H4 H 0.523301 0.339860 0.100992 0.093 Uiso 1 1 calc R U . . .
C5 C 0.814(2) 0.3643(7) 0.0638(3) 0.081(3) Uani 1 1 d . . . . .
H5 H 0.787118 0.432432 0.056627 0.097 Uiso 1 1 calc R U . . .
C6 C 1.006(2) 0.3203(8) 0.0483(3) 0.091(3) Uani 1 1 d . . . . .
H6 H 1.110166 0.358058 0.029737 0.109 Uiso 1 1 calc R U . . .
C7 C 1.0511(14) 0.2200(6) 0.0592(2) 0.062(2) Uani 1 1 d . . . . .
H7 H 1.186344 0.190632 0.048814 0.074 Uiso 1 1 calc R U . . .
C8 C 0.7909(13) -0.0157(4) 0.0622(2) 0.0378(15) Uani 1 1 d . . . . .
C9 C 0.5878(11) -0.0504(5) 0.0796(2) 0.0434(16) Uani 1 1 d . . . . .
H9 H 0.540240 -0.032696 0.112375 0.052 Uiso 1 1 calc R U . . .
C10 C 0.4506(13) -0.1117(5) 0.0496(3) 0.055(2) Uani 1 1 d . . . . .
H10 H 0.314020 -0.136136 0.062121 0.066 Uiso 1 1 calc R U . . .
C11 C 0.5199(16) -0.1352(6) 0.0014(3) 0.064(2) Uani 1 1 d . . . . .
H11 H 0.429872 -0.176646 -0.018955 0.077 Uiso 1 1 calc R U . . .
C12 C 0.7159(18) -0.0999(6) -0.0174(3) 0.066(2) Uani 1 1 d . . . . .
H12 H 0.757147 -0.114598 -0.050931 0.079 Uiso 1 1 calc R U . . .
C13 C 0.8571(13) -0.0414(5) 0.0131(2) 0.054(2) Uani 1 1 d . . . . .
H13 H 0.995709 -0.019514 0.000549 0.064 Uiso 1 1 calc R U . . .
C14 C 1.0643(11) 0.0472(5) 0.1809(2) 0.0343(15) Uani 1 1 d . . . . .
C15 C 1.0094(10) 0.0017(4) 0.23267(19) 0.0290(14) Uani 1 1 d . . . . .
H15 H 0.846705 -0.011165 0.235042 0.035 Uiso 1 1 calc R U . . .
C16 C 1.1408(9) -0.0982(4) 0.2427(2) 0.0343(15) Uani 1 1 d . . . . .
C17 C 1.3122(10) 0.0664(5) 0.28948(19) 0.0336(13) Uani 1 1 d . . . . .
H17 H 1.406725 0.122055 0.276790 0.040 Uiso 1 1 calc R U . . .
C18 C 1.0095(12) -0.1646(5) 0.2806(3) 0.0518(19) Uani 1 1 d . . . . .
H18A H 0.873735 -0.188737 0.264660 0.078 Uiso 1 1 calc R U . . .
H18B H 0.971391 -0.125244 0.310330 0.078 Uiso 1 1 calc R U . . .
H18C H 1.101100 -0.221326 0.290629 0.078 Uiso 1 1 calc R U . . .
C19 C 1.1941(14) -0.1597(5) 0.1948(2) 0.0545(18) Uani 1 1 d . . . . .
H19A H 1.267516 -0.221844 0.204377 0.082 Uiso 1 1 calc R U . . .
H19B H 1.291919 -0.121154 0.172889 0.082 Uiso 1 1 calc R U . . .
H19C H 1.056438 -0.174894 0.176977 0.082 Uiso 1 1 calc R U . . .
C20 C 0.9893(12) 0.0768(5) 0.3213(2) 0.0354(15) Uani 1 1 d . . . . .
C21 C 1.2242(11) 0.0822(4) 0.3442(2) 0.0359(15) Uani 1 1 d . . . . .
H21 H 1.255892 0.023289 0.365903 0.043 Uiso 1 1 calc R U . . .
N1 N 1.0767(8) 0.0714(4) 0.27243(16) 0.0288(11) Uani 1 1 d . . . . .
O1 O 1.2303(8) 0.0952(4) 0.17127(13) 0.0501(12) Uani 1 1 d . . . . .
O2 O 0.9035(7) 0.0233(3) 0.14732(14) 0.0389(11) Uani 1 1 d . . . . .
O3 O 0.7984(9) 0.0754(4) 0.33696(15) 0.0527(12) Uani 1 1 d . . . . .
S1 S 1.4111(3) -0.05809(13) 0.27166(7) 0.0453(4) Uani 1 1 d . . . . .


_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 C21 1.919(6) . ?
C1 O2 1.462(6) . ?
C1 C2 1.514(9) . ?
C1 C8 1.517(8) . ?
C1 H1 0.9800 . ?
C2 C7 1.379(9) . ?
C2 C3 1.381(10) . ?
C3 C4 1.374(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.340(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(12) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.364(9) . ?
C8 C13 1.384(8) . ?
C9 C10 1.389(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.359(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.344(11) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(10) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 O1 1.196(7) . ?
C14 O2 1.333(7) . ?
C14 C15 1.514(8) . ?
C15 N1 1.443(7) . ?
C15 C16 1.552(8) . ?
C15 H15 0.9800 . ?
C16 C19 1.524(8) . ?
C16 C18 1.533(8) . ?
C16 S1 1.848(6) . ?
C17 N1 1.465(7) . ?
C17 C21 1.534(8) . ?
C17 S1 1.803(6) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 O3 1.202(8) . ?
C20 N1 1.380(7) . ?
C20 C21 1.515(9) . ?
C21 H21 0.9800 . ?

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 C1 C2 111.0(5) . . ?
O2 C1 C8 105.8(5) . . ?
C2 C1 C8 112.3(5) . . ?
O2 C1 H1 109.2 . . ?
C2 C1 H1 109.2 . . ?
C8 C1 H1 109.2 . . ?
C7 C2 C3 119.8(7) . . ?
C7 C2 C1 117.6(7) . . ?
C3 C2 C1 122.5(6) . . ?
C4 C3 C2 119.2(8) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 120.6(9) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 120.0(9) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 121.2(10) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 119.2(9) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
C9 C8 C13 118.5(6) . . ?
C9 C8 C1 122.6(5) . . ?
C13 C8 C1 118.9(6) . . ?
C8 C9 C10 121.5(6) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 118.6(7) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C12 C11 C10 121.3(7) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.2(7) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 119.8(7) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
O1 C14 O2 125.0(5) . . ?
O1 C14 C15 125.0(5) . . ?
O2 C14 C15 109.9(5) . . ?
N1 C15 C14 109.3(5) . . ?
N1 C15 C16 106.2(4) . . ?
C14 C15 C16 112.3(5) . . ?
N1 C15 H15 109.6 . . ?
C14 C15 H15 109.6 . . ?
C16 C15 H15 109.6 . . ?
C19 C16 C18 109.4(5) . . ?
C19 C16 C15 114.6(5) . . ?
C18 C16 C15 109.8(5) . . ?
C19 C16 S1 108.0(4) . . ?
C18 C16 S1 109.8(4) . . ?
C15 C16 S1 105.1(4) . . ?
N1 C17 C21 87.3(4) . . ?
N1 C17 S1 105.7(4) . . ?
C21 C17 S1 118.3(4) . . ?
N1 C17 H17 114.1 . . ?
C21 C17 H17 114.1 . . ?
S1 C17 H17 114.1 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 N1 131.8(6) . . ?
O3 C20 C21 136.9(5) . . ?
N1 C20 C21 91.3(5) . . ?
C20 C21 C17 86.5(4) . . ?
C20 C21 Br1 116.2(4) . . ?
C17 C21 Br1 117.3(4) . . ?
C20 C21 H21 111.5 . . ?
C17 C21 H21 111.5 . . ?
Br1 C21 H21 111.5 . . ?
C20 N1 C15 126.6(5) . . ?
C20 N1 C17 94.5(4) . . ?
C15 N1 C17 117.0(4) . . ?
C14 O2 C1 116.8(5) . . ?
C17 S1 C16 94.9(3) . . ?

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
O2 C1 C2 C7 132.7(6) . . . . ?
C8 C1 C2 C7 -109.1(6) . . . . ?
O2 C1 C2 C3 -50.8(7) . . . . ?
C8 C1 C2 C3 67.4(7) . . . . ?
C7 C2 C3 C4 -0.5(9) . . . . ?
C1 C2 C3 C4 -177.0(6) . . . . ?
C2 C3 C4 C5 0.7(10) . . . . ?
C3 C4 C5 C6 0.1(12) . . . . ?
C4 C5 C6 C7 -1.2(14) . . . . ?
C5 C6 C7 C2 1.4(13) . . . . ?
C3 C2 C7 C6 -0.5(10) . . . . ?
C1 C2 C7 C6 176.1(6) . . . . ?
O2 C1 C8 C9 31.4(8) . . . . ?
C2 C1 C8 C9 -89.8(7) . . . . ?
O2 C1 C8 C13 -150.5(6) . . . . ?
C2 C1 C8 C13 88.3(7) . . . . ?
C13 C8 C9 C10 1.2(9) . . . . ?
C1 C8 C9 C10 179.3(6) . . . . ?
C8 C9 C10 C11 -1.4(10) . . . . ?
C9 C10 C11 C12 -0.5(11) . . . . ?
C10 C11 C12 C13 2.6(12) . . . . ?
C9 C8 C13 C12 1.0(10) . . . . ?
C1 C8 C13 C12 -177.2(6) . . . . ?
C11 C12 C13 C8 -2.9(11) . . . . ?
O1 C14 C15 N1 38.7(8) . . . . ?
O2 C14 C15 N1 -143.1(5) . . . . ?
O1 C14 C15 C16 -78.9(8) . . . . ?
O2 C14 C15 C16 99.3(6) . . . . ?
N1 C15 C16 C19 -150.0(5) . . . . ?
C14 C15 C16 C19 -30.5(7) . . . . ?
N1 C15 C16 C18 86.4(5) . . . . ?
C14 C15 C16 C18 -154.1(5) . . . . ?
N1 C15 C16 S1 -31.6(5) . . . . ?
C14 C15 C16 S1 87.9(5) . . . . ?
O3 C20 C21 C17 173.9(8) . . . . ?
N1 C20 C21 C17 -4.7(5) . . . . ?
O3 C20 C21 Br1 -67.3(10) . . . . ?
N1 C20 C21 Br1 114.1(4) . . . . ?
N1 C17 C21 C20 4.4(4) . . . . ?
S1 C17 C21 C20 -102.0(5) . . . . ?
N1 C17 C21 Br1 -113.4(4) . . . . ?
S1 C17 C21 Br1 140.2(4) . . . . ?
O3 C20 N1 C15 -45.1(10) . . . . ?
C21 C20 N1 C15 133.6(5) . . . . ?
O3 C20 N1 C17 -173.8(7) . . . . ?
C21 C20 N1 C17 4.9(5) . . . . ?
C14 C15 N1 C20 155.4(6) . . . . ?
C16 C15 N1 C20 -83.2(7) . . . . ?
C14 C15 N1 C17 -85.5(6) . . . . ?
C16 C15 N1 C17 35.9(6) . . . . ?
C21 C17 N1 C20 -4.9(5) . . . . ?
S1 C17 N1 C20 113.8(4) . . . . ?
C21 C17 N1 C15 -140.1(4) . . . . ?
S1 C17 N1 C15 -21.5(5) . . . . ?
O1 C14 O2 C1 4.6(9) . . . . ?
C15 C14 O2 C1 -173.6(5) . . . . ?
C2 C1 O2 C14 -79.0(7) . . . . ?
C8 C1 O2 C14 158.9(5) . . . . ?
N1 C17 S1 C16 0.0(4) . . . . ?
C21 C17 S1 C16 95.6(5) . . . . ?
C19 C16 S1 C17 141.0(4) . . . . ?
C18 C16 S1 C17 -99.8(5) . . . . ?
C15 C16 S1 C17 18.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C19 H19C Br1 0.96 3.00 3.914(7) 160.3 4_745 yes
C15 H15 S1 0.98 2.82 3.770(6) 163.4 1_455 yes
C19 H19C Br1 0.96 3.00 3.914(7) 160.3 4_745 yes
C15 H15 S1 0.98 2.82 3.770(6) 163.4 1_455 yes
C19 H19C Br1 0.96 3.00 3.914(7) 160.3 4_745 yes
C15 H15 S1 0.98 2.82 3.770(6) 163.4 1_455 yes
C19 H19C Br1 0.96 3.00 3.914(7) 160.3 4_745 yes
C15 H15 S1 0.98 2.82 3.770(6) 163.4 1_455 yes
C15 H15 S1 0.98 2.82 3.770(6) 163.4 1_455 yes
C15 H15 S1 0.98 2.82 3.770(6) 163.4 1_455 yes
C15 H15 S1 0.98 2.82 3.770(6) 163.4 1_455 yes
C19 H19C Br1 0.96 3.00 3.914(7) 160.3 4_745 yes
C15 H15 S1 0.98 2.82 3.770(6) 163.4 1_455 yes
C19 H19C Br1 0.96 3.00 3.914(7) 160.3 4_745 yes
C15 H15 S1 0.98 2.82 3.770(6) 163.4 1_455 yes
C19 H19C Br1 0.96 3.00 3.914(7) 160.3 4_745 yes
C15 H15 S1 0.98 2.82 3.770(6) 163.4 1_455 yes
C19 H19C Br1 0.96 3.00 3.914(7) 160.3 4_745 yes

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.060



####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1967155'
loop_
_audit_author_name
_audit_author_address
'ML Zhou'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2019-11-21 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 Br N O5 S'
_chemical_formula_weight         478.35

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

_cell_length_a                   7.8376(16)
_cell_length_b                   10.864(2)
_cell_length_c                   24.590(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2093.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3551
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      23.12

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.095
_shelx_estimated_absorpt_T_min   0.622
_shelx_estimated_absorpt_T_max   0.679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.622
_exptl_absorpt_correction_T_max  0.679
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            10643
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.728
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3669
_reflns_number_gt                3016
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0600P)²+0.0629P] 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_abs_structure_details 
; 
 Flack x determined using 1043 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.022(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3669
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 1.16703(8) -0.03300(8) 0.83104(3) 0.0554(3) Uani 1 1 d . . . . .
S2 S 0.63371(17) -0.11343(13) 0.77197(6) 0.0330(4) Uani 1 1 d . . . . .
O1 O 0.6566(7) 0.1067(7) 0.6074(2) 0.091(2) Uani 1 1 d . . . . .
O2 O 0.9242(5) 0.0609(4) 0.62881(14) 0.0340(9) Uani 1 1 d . . . . .
O3 O 0.8993(6) 0.2128(4) 0.78246(19) 0.0540(12) Uani 1 1 d . . . . .
O4 O 0.5615(5) -0.0204(4) 0.80612(15) 0.0418(10) Uani 1 1 d . . . . .
O5 O 0.5927(6) -0.2398(4) 0.7808(2) 0.0595(14) Uani 1 1 d . . . . .
N1 N 0.8563(5) 0.0281(4) 0.73455(16) 0.0258(9) Uani 1 1 d . . . . .
C1 C 1.0795(7) -0.0313(5) 0.5550(2) 0.0294(12) Uani 1 1 d . . . . .
C2 C 1.1113(9) -0.1313(6) 0.5876(3) 0.0431(16) Uani 1 1 d . . . . .
H2 H 1.070316 -0.132268 0.623091 0.052 Uiso 1 1 calc R U . . .
C3 C 1.2026(11) -0.2297(7) 0.5685(3) 0.060(2) Uani 1 1 d . . . . .
H3 H 1.221309 -0.297193 0.590998 0.072 Uiso 1 1 calc R U . . .
C4 C 1.2661(10) -0.2300(7) 0.5172(3) 0.061(2) Uani 1 1 d . . . . .
H4 H 1.328266 -0.297069 0.504560 0.073 Uiso 1 1 calc R U . . .
C5 C 1.2380(9) -0.1312(7) 0.4844(3) 0.0549(19) Uani 1 1 d . . . . .
H5 H 1.282015 -0.131000 0.449240 0.066 Uiso 1 1 calc R U . . .
C6 C 1.1455(8) -0.0318(6) 0.5023(2) 0.0430(14) Uani 1 1 d . . . . .
H6 H 1.126931 0.035017 0.479448 0.052 Uiso 1 1 calc R U . . .
C7 C 0.9782(7) 0.0794(5) 0.5721(2) 0.0310(14) Uani 1 1 d . . . . .
H7 H 0.876080 0.084573 0.549239 0.037 Uiso 1 1 calc R U . . .
C8 C 1.0725(8) 0.1986(5) 0.5681(2) 0.0306(13) Uani 1 1 d . . . . .
C9 C 1.0023(10) 0.2968(6) 0.5413(2) 0.0439(16) Uani 1 1 d . . . . .
H9 H 0.892716 0.290849 0.527067 0.053 Uiso 1 1 calc R U . . .
C10 C 1.0936(11) 0.4045(6) 0.5354(3) 0.054(2) Uani 1 1 d . . . . .
H10 H 1.046767 0.470034 0.516198 0.065 Uiso 1 1 calc R U . . .
C11 C 1.2514(11) 0.4154(6) 0.5576(3) 0.0509(19) Uani 1 1 d . . . . .
H11 H 1.310217 0.489383 0.554481 0.061 Uiso 1 1 calc R U . . .
C12 C 1.3248(10) 0.3188(6) 0.5843(2) 0.0453(16) Uani 1 1 d . . . . .
H12 H 1.434395 0.325940 0.598534 0.054 Uiso 1 1 calc R U . . .
C13 C 1.2343(8) 0.2100(6) 0.5901(2) 0.0383(15) Uani 1 1 d . . . . .
H13 H 1.282420 0.144332 0.608916 0.046 Uiso 1 1 calc R U . . .
C14 C 0.7605(8) 0.0746(5) 0.6391(2) 0.0360(15) Uani 1 1 d . . . . .
C15 C 0.7132(7) 0.0466(5) 0.6973(2) 0.0277(12) Uani 1 1 d . . . . .
H15 H 0.646632 0.116404 0.710920 0.033 Uiso 1 1 calc R U . . .
C16 C 0.8587(7) -0.0825(4) 0.7690(2) 0.0279(12) Uani 1 1 d . . . . .
H16 H 0.930641 -0.150380 0.756251 0.033 Uiso 1 1 calc R U . . .
C17 C 0.9310(7) -0.0059(5) 0.8149(2) 0.0308(13) Uani 1 1 d . . . . .
H17 H 0.858555 -0.005742 0.847334 0.037 Uiso 1 1 calc R U . . .
C18 C 0.8993(7) 0.1025(5) 0.7782(2) 0.0322(13) Uani 1 1 d . . . . .
C19 C 0.5990(8) -0.0696(5) 0.7014(2) 0.0320(13) Uani 1 1 d . . . . .
C20 C 0.6593(10) -0.1760(6) 0.6658(3) 0.0551(18) Uani 1 1 d . . . . .
H20A H 0.641827 -0.155565 0.628187 0.083 Uiso 1 1 calc R U . . .
H20B H 0.595516 -0.248721 0.674583 0.083 Uiso 1 1 calc R U . . .
H20C H 0.778411 -0.190568 0.672120 0.083 Uiso 1 1 calc R U . . .
C21 C 0.4111(8) -0.0437(6) 0.6941(3) 0.0459(16) Uani 1 1 d . . . . .
H21A H 0.346787 -0.116387 0.702609 0.069 Uiso 1 1 calc R U . . .
H21B H 0.389527 -0.020121 0.657113 0.069 Uiso 1 1 calc R U . . .
H21C H 0.377520 0.021888 0.717984 0.069 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 C17 1.915(6) . ?
S2 O5 1.426(4) . ?
S2 O4 1.431(4) . ?
S2 C16 1.796(5) . ?
S2 C19 1.821(6) . ?
O1 C14 1.180(7) . ?
O2 C14 1.316(7) . ?
O2 C7 1.471(6) . ?
O3 C18 1.203(7) . ?
N1 C18 1.385(7) . ?
N1 C15 1.462(7) . ?
N1 C16 1.471(6) . ?
C1 C2 1.372(8) . ?
C1 C6 1.395(8) . ?
C1 C7 1.502(8) . ?
C2 C3 1.369(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.356(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.361(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.494(8) . ?
C7 H7 0.9800 . ?
C8 C9 1.369(8) . ?
C8 C13 1.384(9) . ?
C9 C10 1.380(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.356(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(9) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.509(8) . ?
C15 C19 1.551(8) . ?
C15 H15 0.9800 . ?
C16 C17 1.511(7) . ?
C16 H16 0.9800 . ?
C17 C18 1.505(8) . ?
C17 H17 0.9800 . ?
C19 C21 1.510(8) . ?
C19 C20 1.525(8) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
O5 S2 O4 120.1(3) . . ?
O5 S2 C16 114.0(3) . . ?
O4 S2 C16 106.3(2) . . ?
O5 S2 C19 111.3(3) . . ?
O4 S2 C19 108.4(2) . . ?
C16 S2 C19 93.4(3) . . ?
C14 O2 C7 116.6(4) . . ?
C18 N1 C15 126.3(5) . . ?
C18 N1 C16 91.6(4) . . ?
C15 N1 C16 118.9(4) . . ?
C2 C1 C6 118.1(6) . . ?
C2 C1 C7 124.6(5) . . ?
C6 C1 C7 117.3(5) . . ?
C3 C2 C1 120.9(6) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 120.8(7) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.4(7) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 121.0(6) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.8(6) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O2 C7 C8 108.9(4) . . ?
O2 C7 C1 107.9(4) . . ?
C8 C7 C1 114.5(5) . . ?
O2 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C1 C7 H7 108.5 . . ?
C9 C8 C13 119.1(6) . . ?
C9 C8 C7 120.5(6) . . ?
C13 C8 C7 120.3(5) . . ?
C8 C9 C10 120.2(7) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.3(6) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.7(6) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 119.2(7) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C8 C13 C12 120.3(6) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
O1 C14 O2 125.4(6) . . ?
O1 C14 C15 121.1(5) . . ?
O2 C14 C15 113.5(5) . . ?
N1 C15 C14 115.8(4) . . ?
N1 C15 C19 106.9(4) . . ?
C14 C15 C19 111.6(5) . . ?
N1 C15 H15 107.4 . . ?
C14 C15 H15 107.4 . . ?
C19 C15 H15 107.4 . . ?
N1 C16 C17 89.1(4) . . ?
N1 C16 S2 99.4(3) . . ?
C17 C16 S2 116.2(4) . . ?
N1 C16 H16 115.9 . . ?
C17 C16 H16 115.9 . . ?
S2 C16 H16 115.9 . . ?
C18 C17 C16 85.5(4) . . ?
C18 C17 Br1 113.9(4) . . ?
C16 C17 Br1 115.7(4) . . ?
C18 C17 H17 113.0 . . ?
C16 C17 H17 113.0 . . ?
Br1 C17 H17 113.0 . . ?
O3 C18 N1 130.5(6) . . ?
O3 C18 C17 136.7(6) . . ?
N1 C18 C17 92.7(4) . . ?
C21 C19 C20 112.1(5) . . ?
C21 C19 C15 113.8(5) . . ?
C20 C19 C15 113.6(5) . . ?
C21 C19 S2 107.9(4) . . ?
C20 C19 S2 107.6(4) . . ?
C15 C19 S2 100.9(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C6 C1 C2 C3 -1.2(9) . . . . ?
C7 C1 C2 C3 178.9(6) . . . . ?
C1 C2 C3 C4 1.0(11) . . . . ?
C2 C3 C4 C5 -0.2(12) . . . . ?
C3 C4 C5 C6 -0.4(12) . . . . ?
C4 C5 C6 C1 0.2(11) . . . . ?
C2 C1 C6 C5 0.6(9) . . . . ?
C7 C1 C6 C5 -179.5(6) . . . . ?
C14 O2 C7 C8 107.3(5) . . . . ?
C14 O2 C7 C1 -127.8(5) . . . . ?
C2 C1 C7 O2 0.8(8) . . . . ?
C6 C1 C7 O2 -179.1(5) . . . . ?
C2 C1 C7 C8 122.2(6) . . . . ?
C6 C1 C7 C8 -57.7(7) . . . . ?
O2 C7 C8 C9 -110.3(6) . . . . ?
C1 C7 C8 C9 128.9(5) . . . . ?
O2 C7 C8 C13 71.6(6) . . . . ?
C1 C7 C8 C13 -49.3(7) . . . . ?
C13 C8 C9 C10 1.4(9) . . . . ?
C7 C8 C9 C10 -176.8(5) . . . . ?
C8 C9 C10 C11 -2.1(10) . . . . ?
C9 C10 C11 C12 2.3(10) . . . . ?
C10 C11 C12 C13 -1.9(10) . . . . ?
C9 C8 C13 C12 -1.0(9) . . . . ?
C7 C8 C13 C12 177.2(5) . . . . ?
C11 C12 C13 C8 1.2(9) . . . . ?
C7 O2 C14 O1 -4.3(10) . . . . ?
C7 O2 C14 C15 176.5(5) . . . . ?
C18 N1 C15 C14 114.4(6) . . . . ?
C16 N1 C15 C14 -129.2(5) . . . . ?
C18 N1 C15 C19 -120.7(5) . . . . ?
C16 N1 C15 C19 -4.3(6) . . . . ?
O1 C14 C15 N1 -170.1(6) . . . . ?
O2 C14 C15 N1 9.2(8) . . . . ?
O1 C14 C15 C19 67.5(8) . . . . ?
O2 C14 C15 C19 -113.3(6) . . . . ?
C18 N1 C16 C17 -7.9(4) . . . . ?
C15 N1 C16 C17 -141.7(4) . . . . ?
C18 N1 C16 S2 108.5(4) . . . . ?
C15 N1 C16 S2 -25.3(5) . . . . ?
O5 S2 C16 N1 153.2(3) . . . . ?
O4 S2 C16 N1 -72.2(4) . . . . ?
C19 S2 C16 N1 38.1(3) . . . . ?
O5 S2 C16 C17 -113.1(4) . . . . ?
O4 S2 C16 C17 21.5(5) . . . . ?
C19 S2 C16 C17 131.8(4) . . . . ?
N1 C16 C17 C18 7.3(4) . . . . ?
S2 C16 C17 C18 -92.7(4) . . . . ?
N1 C16 C17 Br1 -107.1(4) . . . . ?
S2 C16 C17 Br1 152.9(3) . . . . ?
C15 N1 C18 O3 -40.4(9) . . . . ?
C16 N1 C18 O3 -168.8(6) . . . . ?
C15 N1 C18 C17 136.4(5) . . . . ?
C16 N1 C18 C17 8.0(4) . . . . ?
C16 C17 C18 O3 168.6(7) . . . . ?
Br1 C17 C18 O3 -75.2(8) . . . . ?
C16 C17 C18 N1 -7.8(4) . . . . ?
Br1 C17 C18 N1 108.3(4) . . . . ?
N1 C15 C19 C21 146.5(5) . . . . ?
C14 C15 C19 C21 -86.0(6) . . . . ?
N1 C15 C19 C20 -83.6(6) . . . . ?
C14 C15 C19 C20 43.9(7) . . . . ?
N1 C15 C19 S2 31.3(4) . . . . ?
C14 C15 C19 S2 158.7(4) . . . . ?
O5 S2 C19 C21 81.3(5) . . . . ?
O4 S2 C19 C21 -52.9(5) . . . . ?
C16 S2 C19 C21 -161.3(4) . . . . ?
O5 S2 C19 C20 -39.8(5) . . . . ?
O4 S2 C19 C20 -174.0(4) . . . . ?
C16 S2 C19 C20 77.6(5) . . . . ?
O5 S2 C19 C15 -159.1(4) . . . . ?
O4 S2 C19 C15 66.8(4) . . . . ?
C16 S2 C19 C15 -41.6(4) . . . . ?

_refine_diff_density_max         0.338
_refine_diff_density_min         -1.074
_refine_diff_density_rms         0.123



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ????????????'
####################################################################### 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1970635'
loop_
_audit_author_name
_audit_author_address
'Yanan Zhou'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2019-12-07 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;
_audit_creation_date             2019-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 Br N O4 S'
_chemical_formula_sum            'C21 H20 Br N O4 S'
_chemical_formula_weight         462.35
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.4439(3)
_cell_length_b                   7.6636(4)
_cell_length_c                   20.6198(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.354(4)
_cell_angle_gamma                90
_cell_volume                     1013.85(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1859
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.3290
_cell_measurement_theta_min      4.3040
_shelx_estimated_absorpt_T_max   0.900
_shelx_estimated_absorpt_T_min   0.813
_exptl_absorpt_coefficient_mu    2.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3920
_diffrn_reflns_point_group_measured_fraction_full 0.767
_diffrn_reflns_point_group_measured_fraction_max 0.741
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.793
_diffrn_reflns_theta_min         1.984
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  69.00   1.00    2.00    --    0.00  57.00 -60.00   91
  2  ω    -58.00  -2.00   1.00    2.00    --    0.00 125.00 179.00   56
  3  ω    -17.00  85.00   1.00    2.00    --   53.63 -77.00-180.00  102
  4  ω     32.00 123.00   1.00    2.00    --   53.63  57.00 -60.00   91
  5  ω      4.00 128.00   1.00    2.00    --   53.63  19.00  60.00  124
  6  ω     64.00  92.00   1.00    2.00    --   53.63-125.00 -60.00   28
  7  ω    113.00 140.00   1.00    2.00    --  107.26 111.00-180.00   27
  8  ω     71.00 147.00   1.00    2.00    --  107.26 -25.00  90.00   76
  9  ω     95.00 171.00   1.00    2.00    --  107.26  38.00  90.00   76
 10  ω     50.00 131.00   1.00    2.00    --  107.26 -63.00 -90.00   81
 11  ω     36.00 131.00   1.00    2.00    --  107.26 -91.00-180.00   95
 12  ω     97.00 168.00   1.00    2.00    --  107.26  63.00 -60.00   71
 13  ω     65.00 119.00   1.00    2.00    --  107.26 -91.00   0.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0639897000
_diffrn_orient_matrix_UB_12      0.1216245000
_diffrn_orient_matrix_UB_13      -0.0579321000
_diffrn_orient_matrix_UB_21      -0.0159916000
_diffrn_orient_matrix_UB_22      0.1538599000
_diffrn_orient_matrix_UB_23      0.0474244000
_diffrn_orient_matrix_UB_31      0.2306419000
_diffrn_orient_matrix_UB_32      0.0446970000
_diffrn_orient_matrix_UB_33      -0.0054586000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.416
_reflns_Friedel_fraction_full    0.500
_reflns_Friedel_fraction_max     0.473
_reflns_number_gt                2655
_reflns_number_total             2897
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.706
_refine_diff_density_min         -1.097
_refine_diff_density_rms         0.142
_refine_ls_abs_structure_details 
;
 Flack x determined using 709 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.37(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2897
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0683
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1291P)²+2.1821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1848
_refine_ls_wR_factor_ref         0.1911
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C7(H7), C9(H9), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C10(H10), C11(H11), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.60268(15) 0.95016(13) 0.06418(5) 0.0367(4) Uani 1 1 d . . . . .
S1 S 0.0265(3) 1.2797(3) 0.06959(11) 0.0225(5) Uani 1 1 d . . . . .
O1 O 0.4688(10) 1.4490(14) 0.2565(3) 0.0328(15) Uani 1 1 d . . . . .
O2 O 0.3379(11) 0.9366(12) 0.2125(3) 0.0318(16) Uani 1 1 d . . . . .
O3 O 0.1493(10) 1.5409(9) 0.2786(3) 0.0233(14) Uani 1 1 d . . . . .
O4 O 0.0073(12) 1.3866(11) 0.0085(3) 0.0319(16) Uani 1 1 d . . . . .
N1 N 0.3058(13) 1.2151(11) 0.1635(4) 0.0218(17) Uani 1 1 d . . . . .
C1 C 0.2824(13) 1.4445(17) 0.2469(4) 0.0226(17) Uani 1 1 d . . . . .
C2 C 0.0407(14) 1.4353(14) 0.1397(4) 0.0202(18) Uani 1 1 d . . . . .
C3 C 0.3416(15) 1.0223(14) 0.0934(5) 0.023(2) Uani 1 1 d . . . . .
H3 H 0.2243 0.9560 0.0720 0.027 Uiso 1 1 calc R . . . .
C4 C -0.1820(17) 1.4765(19) 0.1542(6) 0.042(3) Uani 1 1 d . . . . .
H4A H -0.2530 1.5362 0.1176 0.063 Uiso 1 1 calc GR . . . .
H4B H -0.1793 1.5495 0.1921 0.063 Uiso 1 1 calc GR . . . .
H4C H -0.2539 1.3699 0.1619 0.063 Uiso 1 1 calc GR . . . .
C5 C 0.1914(16) 1.9746(15) 0.3558(4) 0.027(2) Uani 1 1 d . . . . .
H5 H 0.3298 1.9746 0.3733 0.032 Uiso 1 1 calc R . . . .
C6 C 0.3302(15) 1.0347(14) 0.1669(5) 0.023(2) Uani 1 1 d . . . . .
C7 C 0.2979(14) 1.2192(12) 0.0926(4) 0.0182(18) Uani 1 1 d . . . . .
H7 H 0.4030 1.2924 0.0745 0.022 Uiso 1 1 calc R . . . .
C8 C 0.2714(15) 1.5685(14) 0.3928(5) 0.025(2) Uani 1 1 d . . . . .
C9 C 0.1627(15) 1.3296(12) 0.1964(4) 0.0198(18) Uani 1 1 d . . . . .
H9 H 0.0642 1.2570 0.2178 0.024 Uiso 1 1 calc R . . . .
C10 C -0.2174(17) 1.9734(19) 0.3059(5) 0.038(3) Uani 1 1 d . . . . .
H10 H -0.3559 1.9736 0.2885 0.045 Uiso 1 1 calc R . . . .
C11 C -0.1043(18) 1.8229(16) 0.3043(6) 0.033(2) Uani 1 1 d . . . . .
H11 H -0.1669 1.7214 0.2872 0.039 Uiso 1 1 calc R . . . .
C12 C 0.2417(14) 1.6626(14) 0.3282(4) 0.024(2) Uani 1 1 d . . . . .
H12 H 0.3790 1.6980 0.3160 0.028 Uiso 1 1 calc R . . . .
C13 C 0.4574(17) 1.4805(16) 0.4126(5) 0.034(3) Uani 1 1 d . . . . .
H13 H 0.5656 1.4820 0.3858 0.040 Uiso 1 1 calc R . . . .
C14 C 0.1566(18) 1.5996(15) 0.1219(5) 0.033(2) Uani 1 1 d . . . . .
H14A H 0.3007 1.5721 0.1188 0.050 Uiso 1 1 calc GR . . . .
H14B H 0.1460 1.6867 0.1549 0.050 Uiso 1 1 calc GR . . . .
H14C H 0.0961 1.6433 0.0807 0.050 Uiso 1 1 calc GR . . . .
C15 C 0.322(2) 1.3838(17) 0.5108(5) 0.039(3) Uani 1 1 d . . . . .
H15 H 0.3381 1.3207 0.5494 0.047 Uiso 1 1 calc R . . . .
C16 C 0.1351(18) 1.4715(18) 0.4923(5) 0.037(3) Uani 1 1 d . . . . .
H16 H 0.0279 1.4699 0.5195 0.044 Uiso 1 1 calc R . . . .
C17 C 0.1096(16) 1.5595(16) 0.4344(5) 0.032(2) Uani 1 1 d . . . . .
H17 H -0.0167 1.6145 0.4222 0.038 Uiso 1 1 calc R . . . .
C18 C 0.0780(19) 2.1242(17) 0.3578(5) 0.035(3) Uani 1 1 d . . . . .
H18 H 0.1394 2.2250 0.3759 0.042 Uiso 1 1 calc R . . . .
C19 C 0.1059(15) 1.8218(14) 0.3284(4) 0.023(2) Uani 1 1 d . . . . .
C20 C -0.131(2) 2.1253(17) 0.3326(6) 0.039(3) Uani 1 1 d . . . . .
H20 H -0.2105 2.2264 0.3338 0.047 Uiso 1 1 calc R . . . .
C21 C 0.4834(18) 1.3922(17) 0.4708(5) 0.038(3) Uani 1 1 d . . . . .
H21 H 0.6097 1.3377 0.4835 0.046 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 C3 1.920(10) . ?
S1 O4 1.498(8) . ?
S1 C2 1.870(10) . ?
S1 C7 1.829(9) . ?
O1 C1 1.199(11) . ?
O2 C6 1.201(13) . ?
O3 C1 1.347(12) . ?
O3 C12 1.468(11) . ?
N1 C6 1.392(13) . ?
N1 C7 1.458(11) . ?
N1 C9 1.482(12) . ?
C1 C9 1.519(13) . ?
C2 C4 1.526(13) . ?
C2 C9 1.571(13) . ?
C2 C14 1.527(14) . ?
C3 C6 1.528(13) . ?
C3 C7 1.535(13) . ?
C5 C18 1.362(17) . ?
C5 C19 1.392(15) . ?
C8 C12 1.512(14) . ?
C8 C13 1.402(15) . ?
C8 C17 1.411(13) . ?
C10 C11 1.366(17) . ?
C10 C20 1.38(2) . ?
C11 C19 1.399(15) . ?
C12 C19 1.502(14) . ?
C13 C21 1.375(16) . ?
C15 C16 1.402(18) . ?
C15 C21 1.385(17) . ?
C16 C17 1.368(16) . ?
C18 C20 1.398(17) . ?

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
O4 S1 C2 107.2(5) . . ?
O4 S1 C7 111.0(4) . . ?
C7 S1 C2 89.1(4) . . ?
C1 O3 C12 116.8(7) . . ?
C6 N1 C7 93.7(7) . . ?
C6 N1 C9 129.5(8) . . ?
C7 N1 C9 118.8(8) . . ?
O1 C1 O3 125.3(10) . . ?
O1 C1 C9 124.5(9) . . ?
O3 C1 C9 110.2(7) . . ?
C4 C2 S1 107.7(7) . . ?
C4 C2 C9 112.1(8) . . ?
C4 C2 C14 111.5(10) . . ?
C9 C2 S1 103.4(7) . . ?
C14 C2 S1 109.2(6) . . ?
C14 C2 C9 112.5(8) . . ?
C6 C3 Br1 117.0(7) . . ?
C6 C3 C7 85.6(7) . . ?
C7 C3 Br1 116.4(6) . . ?
C18 C5 C19 121.8(10) . . ?
O2 C6 N1 131.1(10) . . ?
O2 C6 C3 137.3(10) . . ?
N1 C6 C3 91.6(8) . . ?
N1 C7 S1 102.0(6) . . ?
N1 C7 C3 88.9(7) . . ?
C3 C7 S1 115.0(7) . . ?
C13 C8 C12 121.3(9) . . ?
C13 C8 C17 117.4(10) . . ?
C17 C8 C12 121.2(9) . . ?
N1 C9 C1 111.1(8) . . ?
N1 C9 C2 104.8(7) . . ?
C1 C9 C2 113.4(8) . . ?
C11 C10 C20 121.6(10) . . ?
C10 C11 C19 119.8(11) . . ?
O3 C12 C8 108.7(8) . . ?
O3 C12 C19 108.6(8) . . ?
C19 C12 C8 114.3(8) . . ?
C21 C13 C8 121.5(10) . . ?
C21 C15 C16 119.3(10) . . ?
C17 C16 C15 120.3(10) . . ?
C16 C17 C8 121.2(10) . . ?
C5 C18 C20 119.7(11) . . ?
C5 C19 C11 118.2(10) . . ?
C5 C19 C12 118.4(9) . . ?
C11 C19 C12 123.3(9) . . ?
C10 C20 C18 118.8(11) . . ?
C13 C21 C15 120.3(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.087
_oxdiff_exptl_absorpt_empirical_full_min 0.503
####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1902288'
loop_
_audit_author_name
_audit_author_address
'YN Zhou'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2019-03-11 deposited with the CCDC.	2021-05-14 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         'C21 H20 Br N O4 S'
_chemical_formula_sum            'C21 H20 Br N O4 S'
_chemical_formula_weight         462.35

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      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

_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'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   11.0865(15)
_cell_length_b                   11.0865(15)
_cell_length_c                   16.544(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2033.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3793
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      25.11

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.151
_shelx_estimated_absorpt_T_min   0.615
_shelx_estimated_absorpt_T_max   0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_T_max  0.673
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            10346
_diffrn_reflns_av_unetI/netI     0.0811
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.598
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3550
_reflns_number_gt                2934
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.979

_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       'SMART (Bruker, 2008)'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Bruker, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  'SHELXTL (Bruker, 2008)'
_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)+(0.0691P)²+0.0793P] 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_abs_structure_details 
; 
 Flack x determined using 1136 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.015(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3550
_refine_ls_number_parameters     255
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 -0.08072(8) 0.99291(8) 0.08271(7) 0.0496(3) Uani 1 1 d . . . . .
S1 S 0.13048(18) 0.64747(16) 0.06678(13) 0.0336(5) Uani 1 1 d . . . . .
O1 O 0.4792(4) 0.7682(5) 0.2138(3) 0.0237(12) Uani 1 1 d . . . . .
O2 O 0.3258(5) 0.8605(5) 0.2775(3) 0.0313(13) Uani 1 1 d . . . . .
O3 O 0.2439(6) 1.0061(6) 0.0424(4) 0.0484(17) Uani 1 1 d . . . . .
O4 O 0.1876(6) 0.6880(6) -0.0109(4) 0.0501(18) Uani 1 1 d . . . . .
N1 N 0.1913(5) 0.8508(5) 0.1337(3) 0.0163(13) Uani 1 1 d . . . . .
C1 C 0.5597(6) 0.7890(7) 0.2836(4) 0.0230(17) Uani 1 1 d . . . . .
H1 H 0.5119 0.7829 0.3332 0.028 Uiso 1 1 calc R U . . .
C2 C 0.6127(6) 0.9144(6) 0.2789(5) 0.0217(17) Uani 1 1 d . . . . .
C3 C 0.6234(7) 0.9771(7) 0.2067(5) 0.032(2) Uani 1 1 d . . . . .
H3 H 0.5962 0.9427 0.1588 0.038 Uiso 1 1 calc R U . . .
C4 C 0.6750(8) 1.0913(8) 0.2061(6) 0.044(2) Uani 1 1 d . . . . .
H4 H 0.6826 1.1331 0.1576 0.053 Uiso 1 1 calc R U . . .
C5 C 0.7145(8) 1.1426(7) 0.2764(7) 0.048(3) Uani 1 1 d . . . . .
H5 H 0.7479 1.2196 0.2755 0.057 Uiso 1 1 calc R U . . .
C6 C 0.7051(7) 1.0817(8) 0.3482(6) 0.044(2) Uani 1 1 d . . . . .
H6 H 0.7319 1.1174 0.3958 0.052 Uiso 1 1 calc R U . . .
C7 C 0.6562(7) 0.9675(7) 0.3499(5) 0.032(2) Uani 1 1 d . . . . .
H7 H 0.6520 0.9255 0.3985 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6502(6) 0.6890(6) 0.2829(4) 0.0191(16) Uani 1 1 d . . . . .
C9 C 0.6399(7) 0.5962(7) 0.3395(5) 0.0329(19) Uani 1 1 d . . . . .
H9 H 0.5765 0.5973 0.3763 0.039 Uiso 1 1 calc R U . . .
C10 C 0.7225(8) 0.5022(7) 0.3418(6) 0.041(2) Uani 1 1 d . . . . .
H10 H 0.7153 0.4408 0.3798 0.049 Uiso 1 1 calc R U . . .
C11 C 0.8156(8) 0.5019(7) 0.2864(6) 0.036(2) Uani 1 1 d . . . . .
H11 H 0.8707 0.4387 0.2863 0.043 Uiso 1 1 calc R U . . .
C12 C 0.8277(7) 0.5934(7) 0.2316(5) 0.0308(19) Uani 1 1 d . . . . .
H12 H 0.8916 0.5922 0.1952 0.037 Uiso 1 1 calc R U . . .
C13 C 0.7469(7) 0.6865(7) 0.2297(5) 0.0279(18) Uani 1 1 d . . . . .
H13 H 0.7568 0.7486 0.1925 0.033 Uiso 1 1 calc R U . . .
C14 C 0.3672(6) 0.8092(6) 0.2204(5) 0.0212(17) Uani 1 1 d . . . . .
C15 C 0.2981(6) 0.7784(6) 0.1435(4) 0.0177(15) Uani 1 1 d . . . . .
H15 H 0.3511 0.7918 0.0970 0.021 Uiso 1 1 calc R U . . .
C16 C 0.2540(7) 0.6447(7) 0.1422(6) 0.034(2) Uani 1 1 d . . . . .
C17 C 0.0781(6) 0.7874(6) 0.1138(4) 0.0185(16) Uani 1 1 d . . . . .
H17 H 0.0201 0.7784 0.1581 0.022 Uiso 1 1 calc R U . . .
C18 C 0.1995(9) 0.6059(8) 0.2251(6) 0.049(3) Uani 1 1 d . . . . .
H18A H 0.1606 0.5290 0.2194 0.073 Uiso 1 1 calc R U . . .
H18B H 0.1417 0.6649 0.2424 0.073 Uiso 1 1 calc R U . . .
H18C H 0.2628 0.5999 0.2645 0.073 Uiso 1 1 calc R U . . .
C19 C 0.3490(8) 0.5596(8) 0.1132(8) 0.068(4) Uani 1 1 d . . . . .
H19A H 0.4186 0.5657 0.1475 0.102 Uiso 1 1 calc R U . . .
H19B H 0.3710 0.5798 0.0587 0.102 Uiso 1 1 calc R U . . .
H19C H 0.3185 0.4786 0.1148 0.102 Uiso 1 1 calc R U . . .
C20 C 0.0498(6) 0.8872(7) 0.0512(5) 0.0237(17) Uani 1 1 d . . . . .
H20 H 0.0417 0.8564 -0.0041 0.028 Uiso 1 1 calc R U . . .
C21 C 0.1762(6) 0.9342(6) 0.0702(5) 0.0229(16) Uani 1 1 d . . . . .


_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 C20 1.933(7) . ?
S1 O4 1.501(7) . ?
S1 C17 1.830(7) . ?
S1 C16 1.852(8) . ?
O1 C14 1.327(8) . ?
O1 C1 1.477(8) . ?
O2 C14 1.195(9) . ?
O3 C21 1.187(9) . ?
N1 C21 1.408(10) . ?
N1 C15 1.440(9) . ?
N1 C17 1.475(8) . ?
C1 C8 1.496(10) . ?
C1 C2 1.510(10) . ?
C1 H1 0.9800 . ?
C2 C3 1.388(11) . ?
C2 C7 1.400(11) . ?
C3 C4 1.390(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(12) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.388(11) . ?
C8 C9 1.395(10) . ?
C9 C10 1.388(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(11) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.523(10) . ?
C15 C16 1.561(10) . ?
C15 H15 0.9800 . ?
C16 C19 1.493(12) . ?
C16 C18 1.559(13) . ?
C17 C20 1.548(10) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.529(10) . ?
C20 H20 0.9800 . ?

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
O4 S1 C17 104.1(3) . . ?
O4 S1 C16 105.7(4) . . ?
C17 S1 C16 87.8(3) . . ?
C14 O1 C1 116.6(6) . . ?
C21 N1 C15 123.2(6) . . ?
C21 N1 C17 92.6(5) . . ?
C15 N1 C17 117.3(5) . . ?
O1 C1 C8 106.5(6) . . ?
O1 C1 C2 109.8(6) . . ?
C8 C1 C2 114.9(6) . . ?
O1 C1 H1 108.5 . . ?
C8 C1 H1 108.5 . . ?
C2 C1 H1 108.5 . . ?
C3 C2 C7 118.8(7) . . ?
C3 C2 C1 122.5(7) . . ?
C7 C2 C1 118.6(7) . . ?
C2 C3 C4 119.8(8) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.4(9) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.5(8) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 120.1(8) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 120.3(8) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
C13 C8 C9 118.3(7) . . ?
C13 C8 C1 122.5(7) . . ?
C9 C8 C1 119.2(7) . . ?
C10 C9 C8 121.2(8) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 118.5(8) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C12 C11 C10 120.9(7) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.7(8) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.5(8) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
O2 C14 O1 126.0(7) . . ?
O2 C14 C15 125.0(6) . . ?
O1 C14 C15 109.0(6) . . ?
N1 C15 C14 112.5(6) . . ?
N1 C15 C16 105.7(5) . . ?
C14 C15 C16 112.5(6) . . ?
N1 C15 H15 108.7 . . ?
C14 C15 H15 108.7 . . ?
C16 C15 H15 108.7 . . ?
C19 C16 C18 112.4(8) . . ?
C19 C16 C15 112.5(7) . . ?
C18 C16 C15 111.8(7) . . ?
C19 C16 S1 108.4(7) . . ?
C18 C16 S1 108.1(6) . . ?
C15 C16 S1 103.1(5) . . ?
N1 C17 C20 88.9(5) . . ?
N1 C17 S1 103.2(4) . . ?
C20 C17 S1 112.7(5) . . ?
N1 C17 H17 116.1 . . ?
C20 C17 H17 116.1 . . ?
S1 C17 H17 116.1 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C17 85.4(5) . . ?
C21 C20 Br1 115.1(5) . . ?
C17 C20 Br1 113.9(5) . . ?
C21 C20 H20 113.2 . . ?
C17 C20 H20 113.2 . . ?
Br1 C20 H20 113.2 . . ?
O3 C21 N1 130.9(7) . . ?
O3 C21 C20 136.8(8) . . ?
N1 C21 C20 92.2(5) . . ?

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
C14 O1 C1 C8 151.7(6) . . . . ?
C14 O1 C1 C2 -83.2(7) . . . . ?
O1 C1 C2 C3 -23.9(10) . . . . ?
C8 C1 C2 C3 96.1(8) . . . . ?
O1 C1 C2 C7 158.3(6) . . . . ?
C8 C1 C2 C7 -81.7(9) . . . . ?
C7 C2 C3 C4 -1.0(12) . . . . ?
C1 C2 C3 C4 -178.8(7) . . . . ?
C2 C3 C4 C5 -0.4(13) . . . . ?
C3 C4 C5 C6 0.8(14) . . . . ?
C4 C5 C6 C7 0.3(14) . . . . ?
C5 C6 C7 C2 -1.7(13) . . . . ?
C3 C2 C7 C6 2.1(12) . . . . ?
C1 C2 C7 C6 180.0(7) . . . . ?
O1 C1 C8 C13 76.8(8) . . . . ?
C2 C1 C8 C13 -45.0(10) . . . . ?
O1 C1 C8 C9 -105.3(7) . . . . ?
C2 C1 C8 C9 132.9(7) . . . . ?
C13 C8 C9 C10 -1.3(12) . . . . ?
C1 C8 C9 C10 -179.3(7) . . . . ?
C8 C9 C10 C11 -0.3(13) . . . . ?
C9 C10 C11 C12 1.4(13) . . . . ?
C10 C11 C12 C13 -0.9(13) . . . . ?
C11 C12 C13 C8 -0.8(12) . . . . ?
C9 C8 C13 C12 1.8(11) . . . . ?
C1 C8 C13 C12 179.7(7) . . . . ?
C1 O1 C14 O2 -0.4(10) . . . . ?
C1 O1 C14 C15 -179.4(6) . . . . ?
C21 N1 C15 C14 114.8(7) . . . . ?
C17 N1 C15 C14 -131.6(6) . . . . ?
C21 N1 C15 C16 -122.0(7) . . . . ?
C17 N1 C15 C16 -8.5(8) . . . . ?
O2 C14 C15 N1 19.8(10) . . . . ?
O1 C14 C15 N1 -161.2(5) . . . . ?
O2 C14 C15 C16 -99.4(8) . . . . ?
O1 C14 C15 C16 79.6(7) . . . . ?
N1 C15 C16 C19 153.0(8) . . . . ?
C14 C15 C16 C19 -83.8(9) . . . . ?
N1 C15 C16 C18 -79.4(7) . . . . ?
C14 C15 C16 C18 43.8(8) . . . . ?
N1 C15 C16 S1 36.5(7) . . . . ?
C14 C15 C16 S1 159.6(5) . . . . ?
O4 S1 C16 C19 -59.2(7) . . . . ?
C17 S1 C16 C19 -163.2(7) . . . . ?
O4 S1 C16 C18 178.7(6) . . . . ?
C17 S1 C16 C18 74.7(6) . . . . ?
O4 S1 C16 C15 60.3(6) . . . . ?
C17 S1 C16 C15 -43.8(5) . . . . ?
C21 N1 C17 C20 -7.2(6) . . . . ?
C15 N1 C17 C20 -137.0(6) . . . . ?
C21 N1 C17 S1 105.9(5) . . . . ?
C15 N1 C17 S1 -24.0(7) . . . . ?
O4 S1 C17 N1 -67.2(5) . . . . ?
C16 S1 C17 N1 38.4(5) . . . . ?
O4 S1 C17 C20 27.3(6) . . . . ?
C16 S1 C17 C20 132.9(5) . . . . ?
N1 C17 C20 C21 6.6(5) . . . . ?
S1 C17 C20 C21 -97.3(5) . . . . ?
N1 C17 C20 Br1 -108.8(5) . . . . ?
S1 C17 C20 Br1 147.3(4) . . . . ?
C15 N1 C21 O3 -43.4(12) . . . . ?
C17 N1 C21 O3 -168.8(9) . . . . ?
C15 N1 C21 C20 132.6(6) . . . . ?
C17 N1 C21 C20 7.3(6) . . . . ?
C17 C20 C21 O3 168.7(11) . . . . ?
Br1 C20 C21 O3 -77.1(12) . . . . ?
C17 C20 C21 N1 -6.9(5) . . . . ?
Br1 C20 C21 N1 107.3(5) . . . . ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.134



