# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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 2287852'
loop_
_audit_author_name
_audit_author_address
'Yang-En You'
;Hefei University of Technology
China
;
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_audit_creation_date             2023-04-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 Br N O4 S'
_chemical_formula_sum            'C22 H24 Br N O4 S'
_chemical_formula_weight         478.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   26.5945(8)
_cell_length_b                   6.1407(2)
_cell_length_c                   13.3679(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.4980(10)
_cell_angle_gamma                90
_cell_volume                     2122.79(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9810
_cell_measurement_temperature    101.00
_cell_measurement_theta_max      71.91
_cell_measurement_theta_min      3.42
_shelx_estimated_absorpt_T_max   0.703
_shelx_estimated_absorpt_T_min   0.703
_exptl_absorpt_coefficient_mu    3.797
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5177
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1433 before and 0.0628 after correction.
The Ratio of minimum to maximum transmission is 0.6870.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36287
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.157
_diffrn_reflns_theta_min         5.131
_diffrn_ambient_temperature      101.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4047
_reflns_number_total             4094
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.589
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4094
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²+3.4459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0930
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C13(H13), C17(H17), C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.33744(2) 0.48501(4) 0.74050(2) 0.02314(11) Uani 1 1 d . . . . .
S1 S 0.13588(2) 0.20925(9) 0.54085(4) 0.02146(15) Uani 1 1 d . . . . .
O1 O 0.15517(7) 0.0496(3) 0.61861(14) 0.0274(4) Uani 1 1 d . . . . .
O2 O 0.10265(7) 0.1470(3) 0.44466(14) 0.0297(4) Uani 1 1 d . . . . .
O3 O 0.47367(7) 0.8125(3) 0.36067(14) 0.0293(4) Uani 1 1 d . . . . .
O4 O 0.44294(7) 0.4808(3) 0.38488(14) 0.0247(4) Uani 1 1 d . . . . .
N1 N 0.18688(7) 0.3224(3) 0.51333(15) 0.0197(4) Uani 1 1 d . . . . .
C1 C 0.17983(9) 0.5129(4) 0.44410(19) 0.0201(5) Uani 1 1 d . . . . .
H1A H 0.162697 0.634059 0.472077 0.024 Uiso 1 1 calc R U . . .
H1B H 0.159108 0.474748 0.374729 0.024 Uiso 1 1 calc R U . . .
C2 C 0.23574(8) 0.5733(4) 0.44100(17) 0.0183(4) Uani 1 1 d . . . . .
C3 C 0.26475(9) 0.5137(3) 0.55066(18) 0.0170(4) Uani 1 1 d . . . . .
C4 C 0.23114(8) 0.3692(4) 0.59948(18) 0.0208(5) Uani 1 1 d . . . . .
H4A H 0.249529 0.233841 0.626835 0.025 Uiso 1 1 calc R U . . .
H4B H 0.219995 0.445758 0.655804 0.025 Uiso 1 1 calc R U . . .
C5 C 0.23849(9) 0.8134(4) 0.4132(2) 0.0239(5) Uani 1 1 d . . . . .
H5A H 0.228949 0.903502 0.466348 0.036 Uiso 1 1 calc R U . . .
H5B H 0.214503 0.841556 0.346765 0.036 Uiso 1 1 calc R U . . .
H5C H 0.273779 0.849178 0.408503 0.036 Uiso 1 1 calc R U . . .
C6 C 0.25368(9) 0.4287(4) 0.36186(18) 0.0237(5) Uani 1 1 d . . . . .
H6A H 0.289976 0.460180 0.363410 0.036 Uiso 1 1 calc R U . . .
H6B H 0.232367 0.458801 0.292935 0.036 Uiso 1 1 calc R U . . .
H6C H 0.250099 0.275107 0.378852 0.036 Uiso 1 1 calc R U . . .
C7 C 0.31150(8) 0.5786(4) 0.60013(17) 0.0181(4) Uani 1 1 d . . . . .
C8 C 0.34885(8) 0.7212(4) 0.56473(17) 0.0178(4) Uani 1 1 d . . . . .
C9 C 0.37761(8) 0.6424(4) 0.49788(17) 0.0177(4) Uani 1 1 d . . . . .
H9 H 0.372915 0.496901 0.473384 0.021 Uiso 1 1 calc R U . . .
C10 C 0.41338(8) 0.7776(4) 0.46686(17) 0.0184(4) Uani 1 1 d . . . . .
C11 C 0.42017(9) 0.9909(4) 0.50199(19) 0.0213(5) Uani 1 1 d . . . . .
H11 H 0.443953 1.083533 0.479519 0.026 Uiso 1 1 calc R U . . .
C12 C 0.39217(9) 1.0684(4) 0.56989(19) 0.0238(5) Uani 1 1 d . . . . .
H12 H 0.397121 1.213702 0.594621 0.029 Uiso 1 1 calc R U . . .
C13 C 0.35693(9) 0.9344(4) 0.60190(18) 0.0217(5) Uani 1 1 d . . . . .
H13 H 0.338217 0.987643 0.649250 0.026 Uiso 1 1 calc R U . . .
C14 C 0.44623(8) 0.6964(4) 0.39802(18) 0.0206(5) Uani 1 1 d . . . . .
C15 C 0.47511(9) 0.3916(5) 0.3205(2) 0.0277(5) Uani 1 1 d . . . . .
H15A H 0.466448 0.462576 0.252958 0.042 Uiso 1 1 calc R U . . .
H15B H 0.468941 0.234624 0.311941 0.042 Uiso 1 1 calc R U . . .
H15C H 0.511609 0.417563 0.353123 0.042 Uiso 1 1 calc R U . . .
C16 C 0.10426(8) 0.4166(4) 0.59343(18) 0.0203(5) Uani 1 1 d . . . . .
C17 C 0.06895(9) 0.5493(4) 0.52705(19) 0.0251(5) Uani 1 1 d . . . . .
H17 H 0.060890 0.522815 0.455046 0.030 Uiso 1 1 calc R U . . .
C18 C 0.04581(9) 0.7193(4) 0.56672(19) 0.0253(5) Uani 1 1 d . . . . .
H18 H 0.021730 0.809340 0.521308 0.030 Uiso 1 1 calc R U . . .
C19 C 0.05695(9) 0.7617(4) 0.67158(19) 0.0222(5) Uani 1 1 d . . . . .
C20 C 0.09219(9) 0.6261(4) 0.73695(18) 0.0231(5) Uani 1 1 d . . . . .
H20 H 0.099981 0.651912 0.808997 0.028 Uiso 1 1 calc R U . . .
C21 C 0.11594(9) 0.4551(4) 0.69889(19) 0.0219(5) Uani 1 1 d . . . . .
H21 H 0.139975 0.364803 0.744246 0.026 Uiso 1 1 calc R U . . .
C22 C 0.03155(10) 0.9477(5) 0.7137(2) 0.0311(6) Uani 1 1 d . . . . .
H22A H 0.017545 0.896096 0.771009 0.047 Uiso 1 1 calc R U . . .
H22B H 0.003432 1.006096 0.659417 0.047 Uiso 1 1 calc R U . . .
H22C H 0.057108 1.062402 0.738018 0.047 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 C7 1.930(2) . ?
S1 O1 1.4339(19) . ?
S1 O2 1.4319(18) . ?
S1 N1 1.6401(19) . ?
S1 C16 1.760(2) . ?
O3 C14 1.209(3) . ?
O4 C14 1.336(3) . ?
O4 C15 1.455(3) . ?
N1 C1 1.476(3) . ?
N1 C4 1.470(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.542(3) . ?
C2 C3 1.533(3) . ?
C2 C5 1.526(3) . ?
C2 C6 1.540(3) . ?
C3 C4 1.512(3) . ?
C3 C7 1.326(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.482(3) . ?
C8 C9 1.392(3) . ?
C8 C13 1.399(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.397(3) . ?
C10 C11 1.389(3) . ?
C10 C14 1.495(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(3) . ?
C13 H13 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.394(3) . ?
C16 C21 1.391(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.379(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(4) . ?
C19 C20 1.398(3) . ?
C19 C22 1.502(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.382(4) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
O1 S1 N1 106.11(10) . . ?
O1 S1 C16 109.18(11) . . ?
O2 S1 O1 120.65(11) . . ?
O2 S1 N1 106.33(10) . . ?
O2 S1 C16 107.43(11) . . ?
N1 S1 C16 106.28(10) . . ?
C14 O4 C15 114.91(19) . . ?
C1 N1 S1 119.05(15) . . ?
C4 N1 S1 117.38(15) . . ?
C4 N1 C1 107.30(17) . . ?
N1 C1 H1A 111.2 . . ?
N1 C1 H1B 111.2 . . ?
N1 C1 C2 103.01(18) . . ?
H1A C1 H1B 109.1 . . ?
C2 C1 H1A 111.2 . . ?
C2 C1 H1B 111.2 . . ?
C3 C2 C1 100.96(18) . . ?
C3 C2 C6 110.61(18) . . ?
C5 C2 C1 109.88(18) . . ?
C5 C2 C3 114.94(19) . . ?
C5 C2 C6 110.44(19) . . ?
C6 C2 C1 109.58(19) . . ?
C4 C3 C2 109.68(18) . . ?
C7 C3 C2 127.5(2) . . ?
C7 C3 C4 122.8(2) . . ?
N1 C4 C3 102.86(18) . . ?
N1 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 Br1 118.44(17) . . ?
C3 C7 C8 129.7(2) . . ?
C8 C7 Br1 111.86(15) . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 C13 119.4(2) . . ?
C13 C8 C7 119.9(2) . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 119.9(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C14 121.4(2) . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 C14 118.3(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
O3 C14 O4 123.9(2) . . ?
O3 C14 C10 123.6(2) . . ?
O4 C14 C10 112.46(19) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 S1 118.83(18) . . ?
C21 C16 S1 120.86(19) . . ?
C21 C16 C17 120.2(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.5(2) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.4(2) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C20 118.3(2) . . ?
C18 C19 C22 120.8(2) . . ?
C20 C19 C22 120.9(2) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.3(2) . . ?
C21 C20 H20 119.3 . . ?
C16 C21 H21 120.4 . . ?
C20 C21 C16 119.3(2) . . ?
C20 C21 H21 120.4 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
Br1 C7 C8 C9 104.9(2) . . . . ?
Br1 C7 C8 C13 -72.4(2) . . . . ?
S1 N1 C1 C2 178.19(15) . . . . ?
S1 N1 C4 C3 -167.87(15) . . . . ?
S1 C16 C17 C18 -176.76(18) . . . . ?
S1 C16 C21 C20 176.85(17) . . . . ?
O1 S1 N1 C1 -172.76(17) . . . . ?
O1 S1 N1 C4 -40.6(2) . . . . ?
O1 S1 C16 C17 -159.77(18) . . . . ?
O1 S1 C16 C21 23.3(2) . . . . ?
O2 S1 N1 C1 57.6(2) . . . . ?
O2 S1 N1 C4 -170.24(17) . . . . ?
O2 S1 C16 C17 -27.3(2) . . . . ?
O2 S1 C16 C21 155.76(18) . . . . ?
N1 S1 C16 C17 86.2(2) . . . . ?
N1 S1 C16 C21 -90.7(2) . . . . ?
N1 C1 C2 C3 -34.0(2) . . . . ?
N1 C1 C2 C5 -155.75(19) . . . . ?
N1 C1 C2 C6 82.7(2) . . . . ?
C1 N1 C4 C3 -30.6(2) . . . . ?
C1 C2 C3 C4 16.2(2) . . . . ?
C1 C2 C3 C7 -162.1(2) . . . . ?
C2 C3 C4 N1 7.8(2) . . . . ?
C2 C3 C7 Br1 177.84(17) . . . . ?
C2 C3 C7 C8 -1.0(4) . . . . ?
C3 C7 C8 C9 -76.2(3) . . . . ?
C3 C7 C8 C13 106.4(3) . . . . ?
C4 N1 C1 C2 41.8(2) . . . . ?
C4 C3 C7 Br1 -0.2(3) . . . . ?
C4 C3 C7 C8 -179.0(2) . . . . ?
C5 C2 C3 C4 134.4(2) . . . . ?
C5 C2 C3 C7 -43.9(3) . . . . ?
C6 C2 C3 C4 -99.7(2) . . . . ?
C6 C2 C3 C7 82.0(3) . . . . ?
C7 C3 C4 N1 -173.8(2) . . . . ?
C7 C8 C9 C10 -178.7(2) . . . . ?
C7 C8 C13 C12 179.4(2) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C8 C9 C10 C14 177.9(2) . . . . ?
C9 C8 C13 C12 2.0(3) . . . . ?
C9 C10 C11 C12 1.4(3) . . . . ?
C9 C10 C14 O3 172.0(2) . . . . ?
C9 C10 C14 O4 -9.7(3) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C11 C10 C14 O3 -9.7(3) . . . . ?
C11 C10 C14 O4 168.5(2) . . . . ?
C11 C12 C13 C8 -0.9(4) . . . . ?
C13 C8 C9 C10 -1.3(3) . . . . ?
C14 C10 C11 C12 -176.9(2) . . . . ?
C15 O4 C14 O3 -0.3(3) . . . . ?
C15 O4 C14 C10 -178.59(19) . . . . ?
C16 S1 N1 C1 -56.62(19) . . . . ?
C16 S1 N1 C4 75.51(19) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C17 C16 C21 C20 0.0(3) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C17 C18 C19 C22 179.9(2) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
C19 C20 C21 C16 -0.4(3) . . . . ?
C21 C16 C17 C18 0.2(3) . . . . ?
C22 C19 C20 C21 -179.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 2287853'
loop_
_audit_author_name
_audit_author_address
'Yang-En You'
;Hefei University of Technology
China
;
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_audit_creation_date             2023-04-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 Br2 N O2 S'
_chemical_formula_sum            'C20 H21 Br2 N O2 S'
_chemical_formula_weight         499.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   24.3597(8)
_cell_length_b                   6.0092(2)
_cell_length_c                   13.7493(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.850(2)
_cell_angle_gamma                90
_cell_volume                     1993.79(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9505
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      71.96
_cell_measurement_theta_min      6.51
_shelx_estimated_absorpt_T_max   0.574
_shelx_estimated_absorpt_T_min   0.574
_exptl_absorpt_coefficient_mu    6.252
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5115
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1503 before and 0.0728 after correction.
The Ratio of minimum to maximum transmission is 0.6787.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            50364
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.083
_diffrn_reflns_theta_min         3.663
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3898
_reflns_number_total             3920
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.044
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3920
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.221
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0284P)²+2.6925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0734
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.64524(2) 0.42993(4) 0.33891(2) 0.02032(9) Uani 1 1 d . . . . .
Br2 Br 0.50673(2) -0.27828(4) 0.63617(2) 0.02172(9) Uani 1 1 d . . . . .
S1 S 0.85205(2) 0.78604(10) 0.49770(4) 0.01884(13) Uani 1 1 d . . . . .
O1 O 0.82925(8) 0.9489(3) 0.42739(14) 0.0249(4) Uani 1 1 d . . . . .
O2 O 0.88745(7) 0.8519(3) 0.58479(13) 0.0270(4) Uani 1 1 d . . . . .
N1 N 0.79902(8) 0.6587(3) 0.53476(14) 0.0171(4) Uani 1 1 d . . . . .
C1 C 0.80900(9) 0.4698(4) 0.60330(17) 0.0175(5) Uani 1 1 d . . . . .
H1A H 0.830683 0.516443 0.666181 0.021 Uiso 1 1 calc R U . . .
H1B H 0.828801 0.347680 0.574518 0.021 Uiso 1 1 calc R U . . .
C2 C 0.74982(9) 0.3990(4) 0.61776(16) 0.0146(4) Uani 1 1 d . . . . .
C3 C 0.71889(9) 0.4409(4) 0.51449(16) 0.0142(4) Uani 1 1 d . . . . .
C4 C 0.75296(9) 0.5960(4) 0.45954(17) 0.0175(5) Uani 1 1 d . . . . .
H4A H 0.766544 0.518908 0.403838 0.021 Uiso 1 1 calc R U . . .
H4B H 0.731145 0.728098 0.434569 0.021 Uiso 1 1 calc R U . . .
C5 C 0.74993(10) 0.1573(4) 0.65118(17) 0.0190(5) Uani 1 1 d . . . . .
H5A H 0.712472 0.114700 0.662422 0.028 Uiso 1 1 calc R U . . .
H5B H 0.775473 0.140194 0.712267 0.028 Uiso 1 1 calc R U . . .
H5C H 0.761908 0.061527 0.600363 0.028 Uiso 1 1 calc R U . . .
C6 C 0.72839(10) 0.5521(4) 0.69402(17) 0.0197(5) Uani 1 1 d . . . . .
H6A H 0.729761 0.707198 0.672445 0.030 Uiso 1 1 calc R U . . .
H6B H 0.751680 0.534422 0.757533 0.030 Uiso 1 1 calc R U . . .
H6C H 0.690069 0.512198 0.700669 0.030 Uiso 1 1 calc R U . . .
C7 C 0.67145(9) 0.3515(4) 0.47363(15) 0.0148(4) Uani 1 1 d . . . . .
C8 C 0.63262(9) 0.1988(4) 0.51387(16) 0.0153(4) Uani 1 1 d . . . . .
C9 C 0.62247(9) -0.0143(4) 0.47385(16) 0.0166(4) Uani 1 1 d . . . . .
H9 H 0.641507 -0.061635 0.421612 0.020 Uiso 1 1 calc R U . . .
C10 C 0.58515(9) -0.1570(4) 0.50924(17) 0.0179(4) Uani 1 1 d . . . . .
H10 H 0.578573 -0.301416 0.481993 0.021 Uiso 1 1 calc R U . . .
C11 C 0.55748(9) -0.0846(4) 0.58550(17) 0.0169(5) Uani 1 1 d . . . . .
C12 C 0.56542(9) 0.1272(4) 0.62425(16) 0.0167(4) Uani 1 1 d . . . . .
H12 H 0.545303 0.175880 0.674831 0.020 Uiso 1 1 calc R U . . .
C13 C 0.60311(9) 0.2675(4) 0.58835(16) 0.0163(4) Uani 1 1 d . . . . .
H13 H 0.608882 0.412810 0.614993 0.020 Uiso 1 1 calc R U . . .
C14 C 0.88761(9) 0.5840(4) 0.43794(17) 0.0179(5) Uani 1 1 d . . . . .
C15 C 0.92549(10) 0.4462(4) 0.49381(18) 0.0219(5) Uani 1 1 d . . . . .
H15 H 0.933531 0.467200 0.562767 0.026 Uiso 1 1 calc R U . . .
C16 C 0.95133(10) 0.2786(4) 0.44845(18) 0.0232(5) Uani 1 1 d . . . . .
H16 H 0.977339 0.185281 0.486757 0.028 Uiso 1 1 calc R U . . .
C17 C 0.93992(10) 0.2439(4) 0.34727(18) 0.0198(5) Uani 1 1 d . . . . .
C18 C 0.90216(10) 0.3854(4) 0.29242(17) 0.0199(5) Uani 1 1 d . . . . .
H18 H 0.894387 0.365574 0.223359 0.024 Uiso 1 1 calc R U . . .
C19 C 0.87584(9) 0.5537(4) 0.33667(18) 0.0192(5) Uani 1 1 d . . . . .
H19 H 0.849972 0.647800 0.298453 0.023 Uiso 1 1 calc R U . . .
C20 C 0.96815(11) 0.0596(5) 0.2995(2) 0.0277(6) Uani 1 1 d . . . . .
H20A H 0.944291 -0.072333 0.293288 0.042 Uiso 1 1 calc R U . . .
H20B H 1.003367 0.023563 0.339839 0.042 Uiso 1 1 calc R U . . .
H20C H 0.975230 0.107339 0.234196 0.042 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 C7 1.933(2) . ?
Br2 C11 1.898(2) . ?
S1 O1 1.4332(19) . ?
S1 O2 1.4326(18) . ?
S1 N1 1.6412(19) . ?
S1 C14 1.759(2) . ?
N1 C1 1.474(3) . ?
N1 C4 1.467(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.542(3) . ?
C2 C3 1.534(3) . ?
C2 C5 1.524(3) . ?
C2 C6 1.539(3) . ?
C3 C4 1.516(3) . ?
C3 C7 1.328(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.478(3) . ?
C8 C9 1.403(3) . ?
C8 C13 1.392(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(3) . ?
C11 C12 1.383(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(3) . ?
C14 C19 1.395(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.397(4) . ?
C17 C18 1.396(3) . ?
C17 C20 1.501(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(4) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
O1 S1 N1 106.19(10) . . ?
O1 S1 C14 109.05(11) . . ?
O2 S1 O1 120.57(11) . . ?
O2 S1 N1 106.19(10) . . ?
O2 S1 C14 107.61(11) . . ?
N1 S1 C14 106.39(10) . . ?
C1 N1 S1 119.29(15) . . ?
C4 N1 S1 117.34(15) . . ?
C4 N1 C1 107.25(18) . . ?
N1 C1 H1A 111.2 . . ?
N1 C1 H1B 111.2 . . ?
N1 C1 C2 102.66(18) . . ?
H1A C1 H1B 109.1 . . ?
C2 C1 H1A 111.2 . . ?
C2 C1 H1B 111.2 . . ?
C3 C2 C1 100.66(17) . . ?
C3 C2 C6 111.29(18) . . ?
C5 C2 C1 109.80(18) . . ?
C5 C2 C3 114.58(18) . . ?
C5 C2 C6 110.56(19) . . ?
C6 C2 C1 109.46(18) . . ?
C4 C3 C2 109.20(18) . . ?
C7 C3 C2 127.9(2) . . ?
C7 C3 C4 122.8(2) . . ?
N1 C4 C3 102.97(18) . . ?
N1 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 Br1 117.47(17) . . ?
C3 C7 C8 131.1(2) . . ?
C8 C7 Br1 111.43(15) . . ?
C9 C8 C7 120.5(2) . . ?
C13 C8 C7 120.8(2) . . ?
C13 C8 C9 118.6(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.7(2) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 Br2 119.44(18) . . ?
C12 C11 Br2 119.11(17) . . ?
C12 C11 C10 121.4(2) . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.1(2) . . ?
C13 C12 H12 120.4 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 121.0(2) . . ?
C12 C13 H13 119.5 . . ?
C15 C14 S1 119.01(18) . . ?
C15 C14 C19 120.3(2) . . ?
C19 C14 S1 120.63(18) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.4 . . ?
C15 C16 C17 121.2(2) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C20 120.3(2) . . ?
C18 C17 C16 118.3(2) . . ?
C18 C17 C20 121.4(2) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.3(2) . . ?
C19 C18 H18 119.4 . . ?
C14 C19 H19 120.3 . . ?
C18 C19 C14 119.4(2) . . ?
C18 C19 H19 120.3 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
Br1 C7 C8 C9 63.6(2) . . . . ?
Br1 C7 C8 C13 -112.8(2) . . . . ?
Br2 C11 C12 C13 179.01(17) . . . . ?
S1 N1 C1 C2 -179.35(15) . . . . ?
S1 N1 C4 C3 167.67(15) . . . . ?
S1 C14 C15 C16 176.31(19) . . . . ?
S1 C14 C19 C18 -176.36(18) . . . . ?
O1 S1 N1 C1 175.98(17) . . . . ?
O1 S1 N1 C4 43.70(19) . . . . ?
O1 S1 C14 C15 162.36(18) . . . . ?
O1 S1 C14 C19 -21.2(2) . . . . ?
O2 S1 N1 C1 -54.5(2) . . . . ?
O2 S1 N1 C4 173.18(17) . . . . ?
O2 S1 C14 C15 30.0(2) . . . . ?
O2 S1 C14 C19 -153.61(19) . . . . ?
N1 S1 C14 C15 -83.5(2) . . . . ?
N1 S1 C14 C19 92.9(2) . . . . ?
N1 C1 C2 C3 36.0(2) . . . . ?
N1 C1 C2 C5 157.17(18) . . . . ?
N1 C1 C2 C6 -81.3(2) . . . . ?
C1 N1 C4 C3 30.2(2) . . . . ?
C1 C2 C3 C4 -18.6(2) . . . . ?
C1 C2 C3 C7 157.9(2) . . . . ?
C2 C3 C4 N1 -5.9(2) . . . . ?
C2 C3 C7 Br1 -177.17(17) . . . . ?
C2 C3 C7 C8 3.9(4) . . . . ?
C3 C7 C8 C9 -117.4(3) . . . . ?
C3 C7 C8 C13 66.2(3) . . . . ?
C4 N1 C1 C2 -42.8(2) . . . . ?
C4 C3 C7 Br1 -1.1(3) . . . . ?
C4 C3 C7 C8 180.0(2) . . . . ?
C5 C2 C3 C4 -136.3(2) . . . . ?
C5 C2 C3 C7 40.2(3) . . . . ?
C6 C2 C3 C4 97.3(2) . . . . ?
C6 C2 C3 C7 -86.2(3) . . . . ?
C7 C3 C4 N1 177.3(2) . . . . ?
C7 C8 C9 C10 -178.4(2) . . . . ?
C7 C8 C13 C12 178.0(2) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C8 C13 C12 1.6(3) . . . . ?
C9 C10 C11 Br2 -179.34(17) . . . . ?
C9 C10 C11 C12 1.8(3) . . . . ?
C10 C11 C12 C13 -2.1(3) . . . . ?
C11 C12 C13 C8 0.4(3) . . . . ?
C13 C8 C9 C10 -1.9(3) . . . . ?
C14 S1 N1 C1 59.90(19) . . . . ?
C14 S1 N1 C4 -72.38(19) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C14 C19 C18 0.0(3) . . . . ?
C15 C16 C17 C18 0.9(4) . . . . ?
C15 C16 C17 C20 -179.5(2) . . . . ?
C16 C17 C18 C19 -1.0(4) . . . . ?
C17 C18 C19 C14 0.6(3) . . . . ?
C19 C14 C15 C16 -0.1(4) . . . . ?
C20 C17 C18 C19 179.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
