# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_cyg390m
_database_code_depnum_ccdc_archive 'CCDC 2204888'
loop_
_audit_author_name
_audit_author_address
'Wang Hongling'
;Nanyang Technological University
China
;
_audit_update_record             
;
2022-09-02 deposited with the CCDC.	2023-05-02 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Br N O4 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         496.36
_chemical_absolute_configuration ad

_chemical_melting_point          ?

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

_cell_length_a                   9.0665(5)
_cell_length_b                   9.8398(6)
_cell_length_c                   23.5145(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2097.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      2.2437
_cell_measurement_theta_max      31.5925
_cell_measurement_temperature    98.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008

_exptl_absorpt_coefficient_mu    2.092
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_T_max  0.82

_exptl_special_details           
;
;

_diffrn_ambient_temperature      98.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CPAD detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            40264
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         33.75
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       35

_refine_special_details          
;
;

_reflns_number_total             8346
_reflns_number_gt                6074
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.988

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0865
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_number_reflns         8346
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.828
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 2068 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.049(4)

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'

_computing_data_collection       'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.13070(3) 0.05922(4) 0.37435(2) 0.02903(10) Uani d . . . 1 . .
C C1 0.6621(3) 0.4993(3) 0.31220(11) 0.0144(5) Uani d . . . 1 . .
C C2 0.6962(3) 0.6323(3) 0.29657(12) 0.0174(6) Uani d . . . 1 . .
H H2 0.622328 0.700551 0.294539 0.021000 Uiso calc U . R 1 . .
C C3 0.8423(3) 0.6608(3) 0.28415(12) 0.0197(6) Uani d . . . 1 . .
H H3 0.868512 0.750858 0.273660 0.024000 Uiso calc U . R 1 . .
C C4 0.9520(3) 0.5618(3) 0.28650(12) 0.0208(6) Uani d . . . 1 . .
H H4 1.050840 0.585176 0.277294 0.025000 Uiso calc U . R 1 . .
C C5 0.9181(3) 0.4291(3) 0.30224(12) 0.0184(6) Uani d . . . 1 . .
H H5 0.992738 0.361522 0.304434 0.022000 Uiso calc U . R 1 . .
C C6 0.7713(3) 0.3979(3) 0.31472(12) 0.0152(5) Uani d . . . 1 . .
C C7 0.6971(3) 0.2774(3) 0.33109(12) 0.0149(6) Uani d . . . 1 . .
C C8 0.6754(3) 0.0395(3) 0.33937(12) 0.0186(6) Uani d . . . 1 . .
C C9 0.5161(3) 0.0592(3) 0.32396(11) 0.0175(5) Uani d . . . 1 . .
H H9A 0.459941 -0.021740 0.336531 0.021000 Uiso calc U . R 1 . .
H H9B 0.507914 0.064540 0.282035 0.021000 Uiso calc U . R 1 . .
C C10 0.4438(3) 0.1873(3) 0.35004(12) 0.0157(5) Uani d . . . 1 . .
H H10 0.349971 0.207184 0.329312 0.019000 Uiso calc U . R 1 . .
C C11 0.5515(3) 0.2995(3) 0.33894(12) 0.0147(5) Uani d . . . 1 . .
C C12 0.4094(3) 0.1633(3) 0.41229(12) 0.0145(5) Uani d . . . 1 . .
C C13 0.2781(3) 0.1005(3) 0.42924(12) 0.0179(6) Uani d . . . 1 . .
C C14 0.2494(3) 0.0688(3) 0.48555(12) 0.0216(6) Uani d . . . 1 . .
H H14 0.159923 0.024884 0.495731 0.026000 Uiso calc U . R 1 . .
C C15 0.3520(3) 0.1014(3) 0.52677(12) 0.0213(6) Uani d . . . 1 . .
H H15 0.332320 0.081358 0.565553 0.026000 Uiso calc U . R 1 . .
C C16 0.4836(3) 0.1634(3) 0.51173(13) 0.0203(6) Uani d . . . 1 . .
H H16 0.554117 0.185753 0.540108 0.024000 Uiso calc U . R 1 . .
C C17 0.5121(3) 0.1927(3) 0.45474(12) 0.0181(6) Uani d . . . 1 . .
H H17 0.603362 0.233533 0.444617 0.022000 Uiso calc U . R 1 . .
C C18 0.4094(3) 0.5943(3) 0.41289(12) 0.0159(5) Uani d . . . 1 . .
C C19 0.3564(3) 0.5289(3) 0.46102(12) 0.0183(6) Uani d . . . 1 . .
H H19 0.305248 0.445001 0.457826 0.022000 Uiso calc U . R 1 . .
C C20 0.3793(3) 0.5879(3) 0.51385(12) 0.0200(6) Uani d . . . 1 . .
H H20 0.344373 0.543030 0.546993 0.024000 Uiso calc U . R 1 . .
C C21 0.4529(4) 0.7123(3) 0.51927(14) 0.0223(6) Uani d . . . 1 . .
C C22 0.5048(4) 0.7743(3) 0.47004(14) 0.0248(7) Uani d . . . 1 . .
H H22 0.556060 0.858232 0.472963 0.030000 Uiso calc U . R 1 . .
C C23 0.4840(4) 0.7173(3) 0.41716(14) 0.0230(7) Uani d . . . 1 . .
H H23 0.520097 0.761418 0.384042 0.028000 Uiso calc U . R 1 . .
C C24 0.4752(5) 0.7764(4) 0.57626(15) 0.0336(8) Uani d . . . 1 . .
H H24A 0.549687 0.848278 0.573260 0.050000 Uiso calc U . R 1 . .
H H24B 0.508739 0.707421 0.603398 0.050000 Uiso calc U . R 1 . .
H H24C 0.381976 0.815608 0.589490 0.050000 Uiso calc U . R 1 . .
N N1 0.5237(2) 0.4382(3) 0.32574(9) 0.0143(4) Uani d . . . 1 . .
O O1 0.7652(2) 0.1521(2) 0.33771(9) 0.0190(4) Uani d . . . 1 . .
O O2 0.7320(2) -0.0678(2) 0.35079(10) 0.0260(5) Uani d . . . 1 . .
O O3 0.2596(2) 0.4258(2) 0.35055(9) 0.0202(4) Uani d . . . 1 . .
O O4 0.3614(2) 0.6339(2) 0.30545(8) 0.0210(4) Uani d . . . 1 . .
S S1 0.37383(8) 0.52486(7) 0.34556(3) 0.01558(13) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C13 . 1.902(3) ?
C1 C2 . 1.394(4) ?
C1 C6 . 1.406(4) ?
C1 N1 . 1.427(3) ?
C2 C3 . 1.385(4) ?
C3 C4 . 1.393(4) ?
C4 C5 . 1.392(5) ?
C5 C6 . 1.397(4) ?
C6 C7 . 1.417(4) ?
C7 C11 . 1.350(4) ?
C7 O1 . 1.388(3) ?
C8 O2 . 1.205(3) ?
C8 O1 . 1.375(4) ?
C8 C9 . 1.501(4) ?
C9 C10 . 1.548(4) ?
C10 C11 . 1.496(4) ?
C10 C12 . 1.515(4) ?
C11 N1 . 1.422(4) ?
C12 C17 . 1.395(4) ?
C12 C13 . 1.399(4) ?
C13 C14 . 1.385(4) ?
C14 C15 . 1.381(4) ?
C15 C16 . 1.385(4) ?
C16 C17 . 1.395(4) ?
C18 C19 . 1.388(4) ?
C18 C23 . 1.390(4) ?
C18 S1 . 1.754(3) ?
C19 C20 . 1.387(4) ?
C20 C21 . 1.400(4) ?
C21 C22 . 1.391(4) ?
C21 C24 . 1.495(5) ?
C22 C23 . 1.377(4) ?
N1 S1 . 1.671(2) ?
O3 S1 . 1.428(2) ?
O4 S1 . 1.433(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 121.4(3) ?
C2 C1 N1 . . 130.5(2) ?
C6 C1 N1 . . 108.1(2) ?
C3 C2 C1 . . 117.3(3) ?
C2 C3 C4 . . 122.2(3) ?
C5 C4 C3 . . 120.6(3) ?
C4 C5 C6 . . 118.2(3) ?
C5 C6 C1 . . 120.4(3) ?
C5 C6 C7 . . 133.9(3) ?
C1 C6 C7 . . 105.7(2) ?
C11 C7 O1 . . 124.2(3) ?
C11 C7 C6 . . 111.5(3) ?
O1 C7 C6 . . 124.3(3) ?
O2 C8 O1 . . 117.4(3) ?
O2 C8 C9 . . 125.2(3) ?
O1 C8 C9 . . 117.3(3) ?
C8 C9 C10 . . 114.6(2) ?
C11 C10 C12 . . 114.7(2) ?
C11 C10 C9 . . 104.8(2) ?
C12 C10 C9 . . 110.0(2) ?
C7 C11 N1 . . 107.3(3) ?
C7 C11 C10 . . 122.9(3) ?
N1 C11 C10 . . 129.1(2) ?
C17 C12 C13 . . 117.1(3) ?
C17 C12 C10 . . 121.4(2) ?
C13 C12 C10 . . 121.3(2) ?
C14 C13 C12 . . 122.1(3) ?
C14 C13 Br1 . . 117.9(2) ?
C12 C13 Br1 . . 119.9(2) ?
C15 C14 C13 . . 119.5(3) ?
C14 C15 C16 . . 120.2(3) ?
C15 C16 C17 . . 119.7(3) ?
C16 C17 C12 . . 121.4(3) ?
C19 C18 C23 . . 120.9(3) ?
C19 C18 S1 . . 119.5(2) ?
C23 C18 S1 . . 119.6(2) ?
C20 C19 C18 . . 119.0(3) ?
C19 C20 C21 . . 121.2(3) ?
C22 C21 C20 . . 118.0(3) ?
C22 C21 C24 . . 121.0(3) ?
C20 C21 C24 . . 121.0(3) ?
C23 C22 C21 . . 121.8(3) ?
C22 C23 C18 . . 119.1(3) ?
C11 N1 C1 . . 107.3(2) ?
C11 N1 S1 . . 124.97(19) ?
C1 N1 S1 . . 124.20(19) ?
C8 O1 C7 . . 117.1(2) ?
O3 S1 O4 . . 120.56(13) ?
O3 S1 N1 . . 105.34(12) ?
O4 S1 N1 . . 105.22(13) ?
O3 S1 C18 . . 108.98(13) ?
O4 S1 C18 . . 108.49(13) ?
N1 S1 C18 . . 107.51(12) ?

