# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_202409120_auto
_database_code_depnum_ccdc_archive 'CCDC 2441867'
loop_
_audit_author_name
_audit_author_address
LTxray
;nanyang normal university
China
;
_audit_update_record             
;
2025-04-08 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;
_audit_creation_date             2024-09-30
_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         'C24 H18 Br N O4 S'
_chemical_formula_sum            'C24 H18 Br N O4 S'
_chemical_formula_weight         496.36
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         C28H31O6N3S1
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   19.4774(3)
_cell_length_b                   19.8681(3)
_cell_length_c                   5.66262(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2191.31(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4454
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7160
_cell_measurement_theta_min      4.4390
_shelx_estimated_absorpt_T_max   0.708
_shelx_estimated_absorpt_T_min   0.571
_exptl_absorpt_coefficient_mu    3.711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9493
_diffrn_reflns_point_group_measured_fraction_full 0.777
_diffrn_reflns_point_group_measured_fraction_max 0.777
_diffrn_reflns_theta_full        67.067
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         4.451
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00  30.00   87
  2  ω    -44.00  34.00   1.00    1.00    --  -33.50  57.00  90.00   78
  3  ω    -47.00  36.00   1.00    1.00    --  -33.50  37.00-180.00   83
  4  ω    -18.00  11.00   1.00    1.00    --   36.47 -77.00  90.00   29
  5  ω     64.00 110.00   1.00    1.00    --   36.47 178.00 -30.00   46
  6  ω     32.00  73.00   1.00    1.00    --   36.47 -99.00 -90.00   41
  7  ω     47.00 108.00   1.00    1.00    --   36.47  19.00  30.00   61
  8  ω     72.00 104.00   1.00    1.00    --   36.47 178.00 150.00   32
  9  ω     35.00  64.00   1.00    1.00    --   36.47 -77.00  90.00   29
 10  ω     61.00  86.00   1.00    1.00    --   36.47 178.00 -90.00   25
 11  ω    127.00 162.00   1.00    3.50    --  108.00  45.00-120.00   35
 12  ω    122.00 154.00   1.00    3.50    --  108.00 111.00 120.00   32
 13  ω     38.00 128.00   1.00    3.50    --  108.00 -45.00 120.00   90
 14  ω     39.00 123.00   1.00    3.50    --  108.00 -45.00 -30.00   84
 15  ω    120.00 177.00   1.00    3.50    --  108.00  77.00  60.00   57
 16  ω     57.00 108.00   1.00    3.50    --  108.00-111.00 150.00   51
 17  ω     75.00 101.00   1.00    3.50    --  108.00 -94.00 -90.00   26
 18  ω     83.00 172.00   1.00    3.50    --  108.00  30.00 150.00   89
 19  ω    -73.00 -47.00   1.00    1.00    --  -33.50 -57.00  90.00   26
 20  ω     61.00  86.00   1.00    1.00    --   36.47 178.00 120.00   25
 21  ω    133.00 159.00   1.00    3.50    --  108.00  61.00 -60.00   26
 22  ω     89.00 115.00   1.00    3.50    --  108.00  61.00 -60.00   26
 23  ω     12.00  37.00   1.00    1.00    --  -33.50  37.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0745739000
_diffrn_orient_matrix_UB_12      0.0171338000
_diffrn_orient_matrix_UB_13      0.0679862000
_diffrn_orient_matrix_UB_21      0.0132769000
_diffrn_orient_matrix_UB_22      -0.0745960000
_diffrn_orient_matrix_UB_23      0.0586396000
_diffrn_orient_matrix_UB_31      0.0227589000
_diffrn_orient_matrix_UB_32      -0.0125076000
_diffrn_orient_matrix_UB_33      -0.2567759000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.399
_reflns_Friedel_fraction_full    0.498
_reflns_Friedel_fraction_max     0.498
_reflns_number_gt                2759
_reflns_number_total             3040
_reflns_odcompleteness_completeness 99.87
_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 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 707 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3040
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.050
_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)+(0.0704P)²+0.3212P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1203
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C16(H16),
 C19(H19), C20(H20), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.95099(3) 0.18130(4) 0.63946(19) 0.0753(3) Uani 1 1 d . . . . .
S1 S 0.67644(7) 0.32611(6) -0.0640(3) 0.0463(3) Uani 1 1 d . . . . .
O1 O 0.7351(2) 0.3375(2) -0.2057(9) 0.0609(11) Uani 1 1 d . . . . .
O2 O 0.6123(2) 0.3111(2) -0.1693(9) 0.0620(12) Uani 1 1 d . . . . .
O3 O 0.53786(19) 0.17632(19) 0.2848(10) 0.0586(12) Uani 1 1 d . . . . .
O4 O 0.6561(3) 0.1437(2) 0.7761(9) 0.0799(16) Uani 1 1 d . . . . .
N1 N 0.69571(18) 0.25960(18) 0.1113(9) 0.0403(9) Uani 1 1 d . . . . .
C1 C 0.6665(3) 0.3929(2) 0.1353(13) 0.0499(13) Uani 1 1 d . . . . .
C2 C 0.6074(4) 0.3973(3) 0.2640(19) 0.086(3) Uani 1 1 d . . . . .
H2 H 0.5727 0.3655 0.2454 0.103 Uiso 1 1 calc R . . . .
C3 C 0.5997(5) 0.4502(4) 0.424(2) 0.096(3) Uani 1 1 d . . . . .
H3 H 0.5599 0.4536 0.5131 0.115 Uiso 1 1 calc R . . . .
C4 C 0.6514(5) 0.4977(3) 0.4498(16) 0.079(2) Uani 1 1 d . . . . .
C5 C 0.7093(4) 0.4916(3) 0.3185(16) 0.0699(19) Uani 1 1 d . . . . .
H5 H 0.7438 0.5237 0.3354 0.084 Uiso 1 1 calc R . . . .
C6 C 0.7190(3) 0.4396(3) 0.1609(16) 0.0605(16) Uani 1 1 d . . . . .
H6 H 0.7594 0.4359 0.0744 0.073 Uiso 1 1 calc R . . . .
C7 C 0.6406(6) 0.5532(4) 0.629(2) 0.117(4) Uani 1 1 d . . . . .
H7A H 0.6024 0.5806 0.5817 0.175 Uiso 1 1 calc GR . . . .
H7B H 0.6812 0.5804 0.6386 0.175 Uiso 1 1 calc GR . . . .
H7C H 0.6312 0.5337 0.7809 0.175 Uiso 1 1 calc GR . . . .
C8 C 0.8083(3) 0.1820(2) 0.5318(12) 0.0446(12) Uani 1 1 d . . . . .
H8 H 0.8035 0.1511 0.6541 0.054 Uiso 1 1 calc R . . . .
C9 C 0.8712(3) 0.2094(3) 0.4726(12) 0.0496(14) Uani 1 1 d . . . . .
C10 C 0.8789(3) 0.2563(3) 0.2958(13) 0.0577(16) Uani 1 1 d . . . . .
H10 H 0.9222 0.2738 0.2649 0.069 Uiso 1 1 calc R . . . .
C11 C 0.8237(2) 0.2779(3) 0.1630(14) 0.0549(15) Uani 1 1 d . . . . .
H11 H 0.8289 0.3095 0.0430 0.066 Uiso 1 1 calc R . . . .
C12 C 0.7600(2) 0.2502(2) 0.2174(10) 0.0407(12) Uani 1 1 d . . . . .
C13 C 0.7521(2) 0.2033(2) 0.3976(10) 0.0385(11) Uani 1 1 d . . . . .
C14 C 0.6814(2) 0.1828(2) 0.3997(10) 0.0358(11) Uani 1 1 d . . . . .
C15 C 0.6484(2) 0.2177(2) 0.2296(10) 0.0379(11) Uani 1 1 d . . . . .
C16 C 0.5761(2) 0.2080(3) 0.1608(14) 0.0505(13) Uani 1 1 d . . . . .
H16 H 0.5600 0.2265 0.0205 0.061 Uiso 1 1 calc R . . . .
C17 C 0.6531(3) 0.1317(2) 0.5671(10) 0.0424(12) Uani 1 1 d . . . . .
C18 C 0.6287(2) 0.0656(2) 0.4791(10) 0.0375(11) Uani 1 1 d . . . . .
C19 C 0.6487(3) 0.0403(2) 0.2638(11) 0.0458(12) Uani 1 1 d . . . . .
H19 H 0.6758 0.0663 0.1639 0.055 Uiso 1 1 calc R . . . .
C20 C 0.6288(3) -0.0235(3) 0.1952(11) 0.0512(14) Uani 1 1 d . . . . .
H20 H 0.6440 -0.0406 0.0514 0.061 Uiso 1 1 calc R . . . .
C21 C 0.5868(3) -0.0624(2) 0.3365(11) 0.0465(13) Uani 1 1 d . . . . .
C22 C 0.5661(3) -0.0363(3) 0.5510(12) 0.0483(13) Uani 1 1 d . . . . .
H22 H 0.5374 -0.0616 0.6476 0.058 Uiso 1 1 calc R . . . .
C23 C 0.5872(2) 0.0260(2) 0.6243(12) 0.0459(12) Uani 1 1 d . . . . .
H23 H 0.5739 0.0420 0.7716 0.055 Uiso 1 1 calc R . . . .
C24 C 0.5637(4) -0.1308(3) 0.2522(15) 0.0645(18) Uani 1 1 d . . . . .
H24A H 0.5413 -0.1541 0.3791 0.097 Uiso 1 1 calc GR . . . .
H24B H 0.6029 -0.1562 0.2009 0.097 Uiso 1 1 calc GR . . . .
H24C H 0.5323 -0.1255 0.1229 0.097 Uiso 1 1 calc GR . . . .


_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 C9 1.902(5) . ?
S1 O1 1.415(5) . ?
S1 O2 1.417(5) . ?
S1 N1 1.695(4) . ?
S1 C1 1.753(6) . ?
O3 C16 1.202(7) . ?
O4 C17 1.208(7) . ?
N1 C12 1.401(6) . ?
N1 C15 1.412(6) . ?
C1 C2 1.365(9) . ?
C1 C6 1.388(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.395(12) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(12) . ?
C4 C5 1.358(12) . ?
C4 C7 1.513(12) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(10) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9300 . ?
C8 C9 1.383(8) . ?
C8 C13 1.397(8) . ?
C9 C10 1.375(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(7) . ?
C12 C13 1.389(8) . ?
C13 C14 1.436(7) . ?
C14 C15 1.350(8) . ?
C14 C17 1.495(7) . ?
C15 C16 1.473(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.482(6) . ?
C18 C19 1.376(8) . ?
C18 C23 1.395(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.381(8) . ?
C21 C22 1.380(9) . ?
C21 C24 1.509(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.369(7) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O1 S1 O2 120.5(3) . . ?
O1 S1 N1 106.2(2) . . ?
O1 S1 C1 109.5(3) . . ?
O2 S1 N1 106.1(2) . . ?
O2 S1 C1 109.4(3) . . ?
N1 S1 C1 103.8(3) . . ?
C12 N1 S1 123.6(3) . . ?
C12 N1 C15 107.5(4) . . ?
C15 N1 S1 126.4(3) . . ?
C2 C1 S1 119.0(5) . . ?
C2 C1 C6 121.6(7) . . ?
C6 C1 S1 119.4(5) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 118.9(7) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(8) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C7 117.8(9) . . ?
C5 C4 C3 119.0(7) . . ?
C5 C4 C7 123.2(8) . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.3(6) . . ?
C6 C5 H5 118.9 . . ?
C1 C6 H6 121.0 . . ?
C5 C6 C1 118.0(7) . . ?
C5 C6 H6 121.0 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 H8 121.9 . . ?
C9 C8 C13 116.3(6) . . ?
C13 C8 H8 121.9 . . ?
C8 C9 Br1 119.2(5) . . ?
C10 C9 Br1 118.2(4) . . ?
C10 C9 C8 122.6(5) . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.6(5) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 121.6 . . ?
C10 C11 C12 116.8(6) . . ?
C12 C11 H11 121.6 . . ?
C11 C12 N1 130.4(5) . . ?
C13 C12 N1 107.8(4) . . ?
C13 C12 C11 121.7(5) . . ?
C8 C13 C14 131.3(5) . . ?
C12 C13 C8 121.1(5) . . ?
C12 C13 C14 107.6(4) . . ?
C13 C14 C17 123.5(5) . . ?
C15 C14 C13 107.8(4) . . ?
C15 C14 C17 128.7(5) . . ?
N1 C15 C16 125.1(5) . . ?
C14 C15 N1 109.2(4) . . ?
C14 C15 C16 125.3(5) . . ?
O3 C16 C15 120.4(6) . . ?
O3 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
O4 C17 C14 118.0(5) . . ?
O4 C17 C18 121.3(5) . . ?
C18 C17 C14 120.5(5) . . ?
C19 C18 C17 122.0(5) . . ?
C19 C18 C23 118.7(5) . . ?
C23 C18 C17 119.2(5) . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.3(5) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.1(6) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C24 119.8(6) . . ?
C22 C21 C20 118.2(5) . . ?
C22 C21 C24 122.0(6) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.2(5) . . ?
C23 C22 H22 119.4 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.4(6) . . ?
C22 C23 H23 119.8 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 C9 C10 C11 178.4(5) . . . . ?
S1 N1 C12 C11 -19.0(8) . . . . ?
S1 N1 C12 C13 163.1(4) . . . . ?
S1 N1 C15 C14 -163.3(4) . . . . ?
S1 N1 C15 C16 22.9(8) . . . . ?
S1 C1 C2 C3 179.5(8) . . . . ?
S1 C1 C6 C5 179.8(5) . . . . ?
O1 S1 N1 C12 40.2(5) . . . . ?
O1 S1 N1 C15 -160.0(5) . . . . ?
O1 S1 C1 C2 170.1(6) . . . . ?
O1 S1 C1 C6 -10.7(6) . . . . ?
O2 S1 N1 C12 169.6(4) . . . . ?
O2 S1 N1 C15 -30.6(6) . . . . ?
O2 S1 C1 C2 36.0(7) . . . . ?
O2 S1 C1 C6 -144.8(5) . . . . ?
O4 C17 C18 C19 -154.0(7) . . . . ?
O4 C17 C18 C23 22.2(9) . . . . ?
N1 S1 C1 C2 -76.9(6) . . . . ?
N1 S1 C1 C6 102.3(5) . . . . ?
N1 C12 C13 C8 178.1(5) . . . . ?
N1 C12 C13 C14 0.8(5) . . . . ?
N1 C15 C16 O3 -173.0(5) . . . . ?
C1 S1 N1 C12 -75.1(5) . . . . ?
C1 S1 N1 C15 84.7(5) . . . . ?
C1 C2 C3 C4 0.4(15) . . . . ?
C2 C1 C6 C5 -1.0(11) . . . . ?
C2 C3 C4 C5 -0.3(14) . . . . ?
C2 C3 C4 C7 -178.9(10) . . . . ?
C3 C4 C5 C6 -0.4(12) . . . . ?
C4 C5 C6 C1 1.1(11) . . . . ?
C6 C1 C2 C3 0.3(13) . . . . ?
C7 C4 C5 C6 178.1(8) . . . . ?
C8 C9 C10 C11 -1.2(10) . . . . ?
C8 C13 C14 C15 -178.2(5) . . . . ?
C8 C13 C14 C17 2.0(8) . . . . ?
C9 C8 C13 C12 -0.8(8) . . . . ?
C9 C8 C13 C14 175.7(5) . . . . ?
C9 C10 C11 C12 0.2(10) . . . . ?
C10 C11 C12 N1 -177.3(5) . . . . ?
C10 C11 C12 C13 0.4(9) . . . . ?
C11 C12 C13 C8 -0.1(8) . . . . ?
C11 C12 C13 C14 -177.3(5) . . . . ?
C12 N1 C15 C14 -0.9(6) . . . . ?
C12 N1 C15 C16 -174.6(5) . . . . ?
C12 C13 C14 C15 -1.4(6) . . . . ?
C12 C13 C14 C17 178.9(4) . . . . ?
C13 C8 C9 Br1 -178.1(4) . . . . ?
C13 C8 C9 C10 1.5(8) . . . . ?
C13 C14 C15 N1 1.4(6) . . . . ?
C13 C14 C15 C16 175.1(5) . . . . ?
C13 C14 C17 O4 61.4(8) . . . . ?
C13 C14 C17 C18 -112.6(6) . . . . ?
C14 C15 C16 O3 14.3(9) . . . . ?
C14 C17 C18 C19 19.9(8) . . . . ?
C14 C17 C18 C23 -164.0(5) . . . . ?
C15 N1 C12 C11 177.9(6) . . . . ?
C15 N1 C12 C13 0.0(5) . . . . ?
C15 C14 C17 O4 -118.3(7) . . . . ?
C15 C14 C17 C18 67.6(7) . . . . ?
C17 C14 C15 N1 -178.9(4) . . . . ?
C17 C14 C15 C16 -5.1(9) . . . . ?
C17 C18 C19 C20 175.3(5) . . . . ?
C17 C18 C23 C22 -177.5(5) . . . . ?
C18 C19 C20 C21 2.1(9) . . . . ?
C19 C18 C23 C22 -1.2(8) . . . . ?
C19 C20 C21 C22 -1.3(8) . . . . ?
C19 C20 C21 C24 177.6(5) . . . . ?
C20 C21 C22 C23 -0.8(8) . . . . ?
C21 C22 C23 C18 2.0(8) . . . . ?
C23 C18 C19 C20 -0.8(8) . . . . ?
C24 C21 C22 C23 -179.6(6) . . . . ?

_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 1.306
_oxdiff_exptl_absorpt_empirical_full_min 0.823
####################################################################### 
# 
# 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_202409321_auto
_database_code_depnum_ccdc_archive 'CCDC 2441869'
loop_
_audit_author_name
_audit_author_address
LTXRAY
;nanyangnormaluniversity
China
;
_audit_update_record             
;
2025-04-08 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;
_audit_creation_date             2024-09-30
_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         'C24 H19 N O4 S'
_chemical_formula_sum            'C24 H19 N O4 S'
_chemical_formula_weight         417.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C28H31O6N3S1
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5808(7)
_cell_length_b                   9.8636(6)
_cell_length_c                   12.7357(6)
_cell_angle_alpha                69.355(5)
_cell_angle_beta                 80.379(5)
_cell_angle_gamma                85.929(6)
_cell_volume                     994.43(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1958
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.7890
_cell_measurement_theta_min      3.7520
_shelx_estimated_absorpt_T_max   0.875
_shelx_estimated_absorpt_T_min   0.759
_exptl_absorpt_coefficient_mu    1.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7017
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         3.753
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00 -60.00   73
  2  ω    -71.00  39.00   1.00    1.00    --  -33.50  19.00-180.00  110
  3  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00-150.00   73
  4  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00   0.00   87
  5  ω    -32.00  55.00   1.00    1.00    --   36.53 -57.00 150.00   87
  6  ω    -14.00  46.00   1.00    1.00    --   36.53 -57.00-150.00   60
  7  ω     34.00  65.00   1.00    1.00    --   36.53 -77.00-150.00   31
  8  ω    -34.00  -6.00   1.00    1.00    --   36.53 -37.00-120.00   28
  9  ω     78.00 111.00   1.00    1.00    --   36.53 178.00 -90.00   33
 10  ω    -16.00  30.00   1.00    1.00    --   36.53 -77.00-180.00   46
 11  ω     28.00  55.00   1.00    1.00    --   36.53 -77.00  60.00   27
 12  ω     64.00 110.00   1.00    1.00    --   36.53 178.00  60.00   46
 13  ω    -15.00  11.00   1.00    1.00    --   36.53 -77.00-150.00   26
 14  ω     10.00  36.00   1.00    1.00    --   36.53 -99.00  60.00   26
 15  ω     38.00  76.00   1.00    1.00    --   36.53 -99.00  60.00   38
 16  ω     76.00 111.00   1.00    1.00    --   36.53 178.00  30.00   35
 17  ω     61.00 106.00   1.00    6.00    --  108.00 -94.00-120.00   45
 18  ω     49.00 134.00   1.00    6.00    --  108.00 -30.00-180.00   85
 19  ω     43.00  76.00   1.00    6.00    --  108.00 -61.00-180.00   33
 20  ω     60.00 109.00   1.00    6.00    --  108.00-111.00  60.00   49
 21  ω    113.00 158.00   1.00    6.00    --  108.00  77.00 -60.00   45
 22  ω     40.00 109.00   1.00    6.00    --  108.00-111.00 150.00   69
 23  ω     38.00 106.00   1.00    6.00    --  108.00 -94.00-180.00   68
 24  ω     39.00  90.00   1.00    6.00    --  108.00 -94.00 -30.00   51
 25  ω    136.00 175.00   1.00    6.00    --  108.00  45.00-120.00   39
 26  ω     89.00 115.00   1.00    6.00    --  108.00  45.00-120.00   26
 27  ω     38.00 122.00   1.00    6.00    --  108.00 -45.00 -30.00   84
 28  ω     62.00 130.00   1.00    6.00    --  108.00 -77.00-120.00   68
 29  ω    131.00 175.00   1.00    6.00    --  108.00  61.00 -30.00   44
 30  ω    123.00 167.00   1.00    6.00    --  108.00  77.00 -90.00   44
 31  ω     36.00 145.00   1.00    6.00    --  108.00 -15.00 -90.00  109
 32  ω     39.00  72.00   1.00    6.00    --  108.00 -94.00  90.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1187284000
_diffrn_orient_matrix_UB_12      0.1100153000
_diffrn_orient_matrix_UB_13      0.0000620000
_diffrn_orient_matrix_UB_21      -0.1239317000
_diffrn_orient_matrix_UB_22      0.0525854000
_diffrn_orient_matrix_UB_23      0.0801219000
_diffrn_orient_matrix_UB_31      0.0609070000
_diffrn_orient_matrix_UB_32      -0.1139884000
_diffrn_orient_matrix_UB_33      0.1033751000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2428
_reflns_number_total             3527
_reflns_odcompleteness_completeness 99.35
_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 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.015
_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)+(0.0817P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1670
_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. Uiso/Uaniso restraints and constraints
Uanis(O4) = Uanis(O4A)
Uanis(C24) = Uanis(C24A)
3. Others
 Sof(O4A)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(O4)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16),
 C19(H19), C20(H20), C22(H22), C23(H23)
4.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C24(H24A,H24B,H24C), C24A(H24D,H24E,H24F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
S1 S 0.32715(10) 0.24817(9) 0.38859(6) 0.0640(3) Uani 1 1 d . . . . .
O1 O 0.1815(3) 0.3244(3) 0.40059(19) 0.0804(7) Uani 1 1 d . . . . .
O2 O 0.3502(3) 0.1056(3) 0.46506(17) 0.0777(7) Uani 1 1 d . . . . .
O3 O 0.6466(3) -0.0078(2) 0.18797(19) 0.0712(6) Uani 1 1 d . . . . .
O4 O 0.9356(5) 0.0328(5) -0.3188(3) 0.0972(12) Uani 0.839(6) 1 d . . P A 1
O4A O 0.970(3) -0.043(2) -0.270(2) 0.0972(12) Uani 0.161(6) 1 d . . P A 2
N1 N 0.3471(3) 0.2319(3) 0.26194(19) 0.0620(6) Uani 1 1 d . . . . .
C1 C 0.4839(4) 0.3558(3) 0.3835(2) 0.0586(7) Uani 1 1 d . . . . .
C2 C 0.4641(4) 0.5044(4) 0.3489(2) 0.0694(8) Uani 1 1 d . . . . .
H2 H 0.3664 0.5465 0.3329 0.083 Uiso 1 1 calc R . . . .
C3 C 0.5908(5) 0.5903(4) 0.3381(3) 0.0743(9) Uani 1 1 d . . . . .
H3 H 0.5772 0.6904 0.3152 0.089 Uiso 1 1 calc R . . . .
C4 C 0.7379(5) 0.5295(4) 0.3609(3) 0.0713(9) Uani 1 1 d . . . . .
C5 C 0.7526(4) 0.3797(4) 0.4000(3) 0.0743(9) Uani 1 1 d . . . . .
H5 H 0.8488 0.3369 0.4193 0.089 Uiso 1 1 calc R . . . .
C6 C 0.6286(4) 0.2932(4) 0.4107(3) 0.0677(8) Uani 1 1 d . . . . .
H6 H 0.6413 0.1929 0.4362 0.081 Uiso 1 1 calc R . . . .
C7 C 0.8769(5) 0.6250(5) 0.3440(4) 0.0965(12) Uani 1 1 d . . . . .
H7A H 0.9537 0.5708 0.3899 0.145 Uiso 1 1 calc GR . . . .
H7B H 0.8413 0.7071 0.3657 0.145 Uiso 1 1 calc GR . . . .
H7C H 0.9239 0.6576 0.2655 0.145 Uiso 1 1 calc GR . . . .
C8 C 0.3701(4) 0.3998(4) -0.0425(2) 0.0661(8) Uani 1 1 d . . . . .
H8 H 0.4252 0.3831 -0.1063 0.079 Uiso 1 1 calc R . . . .
C9 C 0.2617(4) 0.5126(4) -0.0551(3) 0.0730(9) Uani 1 1 d . . . . .
H9 H 0.2433 0.5709 -0.1274 0.088 Uiso 1 1 calc R . . . .
C10 C 0.1807(4) 0.5393(4) 0.0384(3) 0.0738(9) Uani 1 1 d . . . . .
H10 H 0.1102 0.6173 0.0283 0.089 Uiso 1 1 calc R . . . .
C11 C 0.2019(4) 0.4524(4) 0.1473(3) 0.0673(8) Uani 1 1 d . . . . .
H11 H 0.1447 0.4692 0.2104 0.081 Uiso 1 1 calc R . . . .
C12 C 0.3104(3) 0.3404(3) 0.1593(2) 0.0564(7) Uani 1 1 d . . . . .
C13 C 0.3970(3) 0.3114(3) 0.0650(2) 0.0560(7) Uani 1 1 d . . . . .
C14 C 0.4980(4) 0.1853(3) 0.1096(2) 0.0557(7) Uani 1 1 d . . . . .
C15 C 0.4661(4) 0.1411(3) 0.2297(2) 0.0584(7) Uani 1 1 d . . . . .
C16 C 0.5547(4) 0.0257(4) 0.2749(3) 0.0707(9) Uani 1 1 d . . . . .
H16 H 0.5545 -0.0238 0.3520 0.085 Uiso 1 1 calc R . . . .
C17 C 0.6116(4) 0.0899(3) 0.0864(2) 0.0608(7) Uani 1 1 d . . . . .
C18 C 0.6987(4) 0.0706(3) -0.0157(3) 0.0641(7) Uani 1 1 d . . . . .
C19 C 0.8079(5) -0.0427(4) -0.0103(4) 0.0821(10) Uani 1 1 d . . . . .
H19 H 0.8260 -0.1075 0.0602 0.098 Uiso 1 1 calc R . . . .
C20 C 0.8899(5) -0.0601(5) -0.1085(4) 0.0878(11) Uani 1 1 d . . . . .
H20 H 0.9618 -0.1365 -0.1030 0.105 Uiso 1 1 calc R . . . .
C21 C 0.8659(5) 0.0342(4) -0.2136(4) 0.0824(10) Uani 1 1 d . . . . .
C22 C 0.7574(6) 0.1458(4) -0.2197(3) 0.0943(13) Uani 1 1 d . . . . .
H22 H 0.7383 0.2097 -0.2902 0.113 Uiso 1 1 calc R . . . .
C23 C 0.6775(5) 0.1635(4) -0.1227(3) 0.0859(11) Uani 1 1 d . . . . .
H23 H 0.6065 0.2407 -0.1292 0.103 Uiso 1 1 calc R . . . .
C24 C 1.0445(6) -0.0819(6) -0.3188(5) 0.0987(17) Uani 0.839(6) 1 d . . P A 1
H24A H 1.0859 -0.0737 -0.3956 0.148 Uiso 0.839(6) 1 calc GR . P A 1
H24B H 0.9920 -0.1729 -0.2807 0.148 Uiso 0.839(6) 1 calc GR . P A 1
H24C H 1.1296 -0.0770 -0.2800 0.148 Uiso 0.839(6) 1 calc GR . P A 1
C24A C 0.955(3) 0.038(3) -0.385(3) 0.0987(17) Uani 0.161(6) 1 d . . P A 2
H24D H 1.0486 0.0248 -0.4333 0.148 Uiso 0.161(6) 1 calc GR . P A 2
H24E H 0.9415 0.1390 -0.3942 0.148 Uiso 0.161(6) 1 calc GR . P A 2
H24F H 0.8649 0.0053 -0.4042 0.148 Uiso 0.161(6) 1 calc GR . P A 2


_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
S1 O1 1.426(2) . ?
S1 O2 1.423(2) . ?
S1 N1 1.656(2) . ?
S1 C1 1.751(3) . ?
O3 C16 1.373(4) . ?
O3 C17 1.379(3) . ?
O4 C21 1.377(5) . ?
O4 C24 1.416(7) . ?
O4A C21 1.40(2) . ?
O4A C24A 1.42(4) . ?
N1 C12 1.434(3) . ?
N1 C15 1.415(4) . ?
C1 C2 1.380(4) . ?
C1 C6 1.388(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(5) . ?
C4 C5 1.387(5) . ?
C4 C7 1.512(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9300 . ?
C8 C9 1.380(5) . ?
C8 C13 1.387(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(4) . ?
C12 C13 1.411(4) . ?
C13 C14 1.462(4) . ?
C14 C15 1.418(4) . ?
C14 C17 1.375(4) . ?
C15 C16 1.329(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.455(4) . ?
C18 C19 1.397(5) . ?
C18 C23 1.382(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(6) . ?
C21 C22 1.380(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.369(5) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C24A H24D 0.9600 . ?
C24A H24E 0.9600 . ?
C24A H24F 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
O1 S1 N1 106.03(14) . . ?
O1 S1 C1 109.35(16) . . ?
O2 S1 O1 120.71(16) . . ?
O2 S1 N1 105.05(14) . . ?
O2 S1 C1 108.62(15) . . ?
N1 S1 C1 106.08(13) . . ?
C16 O3 C17 108.4(2) . . ?
C21 O4 C24 115.8(5) . . ?
C21 O4A C24A 100.7(19) . . ?
C12 N1 S1 126.5(2) . . ?
C15 N1 S1 120.9(2) . . ?
C15 N1 C12 106.9(2) . . ?
C2 C1 S1 119.4(3) . . ?
C2 C1 C6 120.0(3) . . ?
C6 C1 S1 120.5(3) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C7 120.5(3) . . ?
C5 C4 C3 118.1(4) . . ?
C5 C4 C7 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 H8 119.9 . . ?
C9 C8 C13 120.1(3) . . ?
C13 C8 H8 119.9 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 121.1 . . ?
C12 C11 C10 117.9(3) . . ?
C12 C11 H11 121.1 . . ?
C11 C12 N1 128.3(3) . . ?
C11 C12 C13 122.1(3) . . ?
C13 C12 N1 109.4(3) . . ?
C8 C13 C12 118.1(3) . . ?
C8 C13 C14 135.0(3) . . ?
C12 C13 C14 106.9(2) . . ?
C15 C14 C13 107.1(3) . . ?
C17 C14 C13 147.5(3) . . ?
C17 C14 C15 105.5(2) . . ?
N1 C15 C14 109.6(2) . . ?
C16 C15 N1 140.8(3) . . ?
C16 C15 C14 109.6(3) . . ?
O3 C16 H16 125.9 . . ?
C15 C16 O3 108.2(3) . . ?
C15 C16 H16 125.9 . . ?
O3 C17 C18 116.0(3) . . ?
C14 C17 O3 108.4(3) . . ?
C14 C17 C18 135.7(3) . . ?
C19 C18 C17 121.6(3) . . ?
C23 C18 C17 121.6(3) . . ?
C23 C18 C19 116.8(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.0(4) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.8(4) . . ?
C21 C20 H20 119.6 . . ?
O4 C21 C22 112.9(4) . . ?
C20 C21 O4 128.5(4) . . ?
C20 C21 O4A 92.6(10) . . ?
C20 C21 C22 118.6(4) . . ?
C22 C21 O4A 148.7(11) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.6(4) . . ?
C23 C22 H22 119.7 . . ?
C18 C23 H23 118.8 . . ?
C22 C23 C18 122.3(4) . . ?
C22 C23 H23 118.8 . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O4A C24A H24D 109.5 . . ?
O4A C24A H24E 109.5 . . ?
O4A C24A H24F 109.5 . . ?
H24D C24A H24E 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 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
S1 N1 C12 C11 -26.9(5) . . . . ?
S1 N1 C12 C13 157.1(2) . . . . ?
S1 N1 C15 C14 -158.2(2) . . . . ?
S1 N1 C15 C16 24.2(6) . . . . ?
S1 C1 C2 C3 -176.0(2) . . . . ?
S1 C1 C6 C5 176.2(2) . . . . ?
O1 S1 N1 C12 40.6(3) . . . . ?
O1 S1 N1 C15 -169.6(2) . . . . ?
O1 S1 C1 C2 -24.0(3) . . . . ?
O1 S1 C1 C6 157.9(2) . . . . ?
O2 S1 N1 C12 169.5(3) . . . . ?
O2 S1 N1 C15 -40.7(3) . . . . ?
O2 S1 C1 C2 -157.6(2) . . . . ?
O2 S1 C1 C6 24.3(3) . . . . ?
O3 C17 C18 C19 1.6(5) . . . . ?
O3 C17 C18 C23 -178.3(3) . . . . ?
O4 C21 C22 C23 -179.7(4) . . . . ?
O4A C21 C22 C23 175(2) . . . . ?
N1 S1 C1 C2 89.9(2) . . . . ?
N1 S1 C1 C6 -88.2(3) . . . . ?
N1 C12 C13 C8 176.1(3) . . . . ?
N1 C12 C13 C14 -3.1(3) . . . . ?
N1 C15 C16 O3 178.1(4) . . . . ?
C1 S1 N1 C12 -75.6(3) . . . . ?
C1 S1 N1 C15 74.2(3) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C1 C6 C5 -1.8(5) . . . . ?
C2 C3 C4 C5 -3.0(5) . . . . ?
C2 C3 C4 C7 177.4(3) . . . . ?
C3 C4 C5 C6 3.2(5) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
C6 C1 C2 C3 2.1(4) . . . . ?
C7 C4 C5 C6 -177.2(3) . . . . ?
C8 C9 C10 C11 -1.7(6) . . . . ?
C8 C13 C14 C15 -178.0(3) . . . . ?
C8 C13 C14 C17 2.3(8) . . . . ?
C9 C8 C13 C12 0.2(5) . . . . ?
C9 C8 C13 C14 179.2(3) . . . . ?
C9 C10 C11 C12 1.8(5) . . . . ?
C10 C11 C12 N1 -176.4(3) . . . . ?
C10 C11 C12 C13 -0.9(5) . . . . ?
C11 C12 C13 C8 -0.1(5) . . . . ?
C11 C12 C13 C14 -179.4(3) . . . . ?
C12 N1 C15 C14 -3.3(3) . . . . ?
C12 N1 C15 C16 179.2(4) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C12 C13 C14 C17 -178.6(5) . . . . ?
C13 C8 C9 C10 0.7(5) . . . . ?
C13 C14 C15 N1 1.4(3) . . . . ?
C13 C14 C15 C16 179.7(3) . . . . ?
C13 C14 C17 O3 179.8(4) . . . . ?
C13 C14 C17 C18 0.1(8) . . . . ?
C14 C15 C16 O3 0.6(4) . . . . ?
C14 C17 C18 C19 -178.7(4) . . . . ?
C14 C17 C18 C23 1.4(6) . . . . ?
C15 N1 C12 C11 179.9(3) . . . . ?
C15 N1 C12 C13 4.0(3) . . . . ?
C15 C14 C17 O3 0.1(3) . . . . ?
C15 C14 C17 C18 -179.6(4) . . . . ?
C16 O3 C17 C14 0.2(4) . . . . ?
C16 O3 C17 C18 -180.0(3) . . . . ?
C17 O3 C16 C15 -0.5(4) . . . . ?
C17 C14 C15 N1 -178.8(3) . . . . ?
C17 C14 C15 C16 -0.5(4) . . . . ?
C17 C18 C19 C20 179.8(3) . . . . ?
C17 C18 C23 C22 -179.3(4) . . . . ?
C18 C19 C20 C21 0.2(6) . . . . ?
C19 C18 C23 C22 0.8(6) . . . . ?
C19 C20 C21 O4 -179.7(4) . . . . ?
C19 C20 C21 O4A -177.5(11) . . . . ?
C19 C20 C21 C22 -0.6(6) . . . . ?
C20 C21 C22 C23 1.1(7) . . . . ?
C21 C22 C23 C18 -1.2(7) . . . . ?
C23 C18 C19 C20 -0.3(6) . . . . ?
C24 O4 C21 C20 1.0(7) . . . . ?
C24 O4 C21 C22 -178.1(4) . . . . ?
C24A O4A C21 C20 177.4(17) . . . . ?
C24A O4A C21 C22 3(3) . . . . ?

_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 1.640
_oxdiff_exptl_absorpt_empirical_full_min 0.793
