# Supplementary Information (SI) for CrystEngComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2443655'
loop_
_audit_author_name
_audit_author_address
'Igor Litvinov'
;Arbuzov Institute of Organic and Physical Chemistry RAS
Russia
;
_audit_update_record             
;
2025-08-06 deposited with the CCDC.	2025-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 Cl2 N2 O3 S'
_chemical_formula_sum            'C23 H18 Cl2 N2 O3 S'
_chemical_formula_weight         473.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8050(17)
_cell_length_b                   10.4025(18)
_cell_length_c                   10.8869(19)
_cell_angle_alpha                78.332(5)
_cell_angle_beta                 85.743(6)
_cell_angle_gamma                88.576(5)
_cell_volume                     1084.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9794
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.47

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.145
_exptl_absorpt_coefficient_mu    0.424
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_max  0.7344
_exptl_absorpt_correction_T_min  0.6864

_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1455 before and 0.0788 after correction.
The Ratio of minimum to maximum transmission is 0.9346.
The λ/2 correction factor is Not present.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS DIAMOND'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49684
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.915
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4256
_reflns_number_gt                3892
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+1.4269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4256
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.74665(5) 1.12193(5) 0.89220(5) 0.02677(14) Uani 1 1 d . . . . .
S1 S 0.60737(5) 0.42503(5) 0.70796(5) 0.02160(13) Uani 1 1 d . . . . .
Cl2 Cl 1.16458(6) 0.16589(7) 0.37468(7) 0.04654(19) Uani 1 1 d . . . . .
O1 O 0.53239(16) 0.76044(14) 0.49783(13) 0.0237(3) Uani 1 1 d . . . . .
O3 O 0.16828(16) 0.88050(16) 0.79455(15) 0.0299(4) Uani 1 1 d . . . . .
N4 N 0.45931(17) 0.63719(15) 0.68948(15) 0.0170(3) Uani 1 1 d . . . . .
O2 O 0.06370(17) 0.73028(17) 0.94707(18) 0.0381(4) Uani 1 1 d . . . . .
N8 N 0.40460(18) 0.47259(17) 0.86974(16) 0.0231(4) Uani 1 1 d . . . . .
C17 C 0.4679(2) 0.83771(19) 0.77450(18) 0.0174(4) Uani 1 1 d . . . . .
C3 C 0.5393(2) 0.66046(19) 0.57680(18) 0.0180(4) Uani 1 1 d . . . . .
C22 C 0.4873(2) 0.96217(19) 0.70152(19) 0.0212(4) Uani 1 1 d . . . . .
H22 H 0.441984 0.987553 0.626083 0.025 Uiso 1 1 calc R U . . .
C2 C 0.6323(2) 0.54624(19) 0.57048(18) 0.0187(4) Uani 1 1 d . . . . .
C9 C 0.4759(2) 0.51743(19) 0.76762(19) 0.0188(4) Uani 1 1 d . . . . .
C20 C 0.6386(2) 1.0114(2) 0.84744(19) 0.0204(4) Uani 1 1 d . . . . .
C19 C 0.6206(2) 0.8875(2) 0.92191(19) 0.0225(4) Uani 1 1 d . . . . .
H19 H 0.666572 0.862276 0.996987 0.027 Uiso 1 1 calc R U . . .
C18 C 0.5343(2) 0.8011(2) 0.88515(19) 0.0208(4) Uani 1 1 d . . . . .
H18 H 0.520338 0.716073 0.935844 0.025 Uiso 1 1 calc R U . . .
C21 C 0.5727(2) 1.0502(2) 0.7380(2) 0.0229(4) Uani 1 1 d . . . . .
H21 H 0.585578 1.135799 0.688298 0.027 Uiso 1 1 calc R U . . .
C10 C 0.7226(2) 0.5475(2) 0.4711(2) 0.0223(4) Uani 1 1 d . . . . .
H10 H 0.719595 0.623868 0.406509 0.027 Uiso 1 1 calc R U . . .
C5 C 0.3756(2) 0.74130(19) 0.73316(18) 0.0180(4) Uani 1 1 d . . . . .
H5 H 0.324144 0.789560 0.661682 0.022 Uiso 1 1 calc R U . . .
C6 C 0.2732(2) 0.6755(2) 0.83753(19) 0.0208(4) Uani 1 1 d . . . . .
C7 C 0.2931(2) 0.5521(2) 0.90085(19) 0.0235(4) Uani 1 1 d . . . . .
C11 C 0.8243(2) 0.4494(2) 0.4478(2) 0.0247(5) Uani 1 1 d . . . . .
C23 C 0.1566(2) 0.7602(2) 0.8679(2) 0.0260(5) Uani 1 1 d . . . . .
C14 C 1.0315(2) 0.2737(3) 0.4003(2) 0.0328(5) Uani 1 1 d . . . . .
C12 C 0.8285(2) 0.3209(2) 0.5183(2) 0.0302(5) Uani 1 1 d . . . . .
H12 H 0.759462 0.293422 0.583742 0.036 Uiso 1 1 calc R U . . .
C16 C 0.9259(2) 0.4850(3) 0.3498(2) 0.0312(5) Uani 1 1 d . . . . .
H16 H 0.923812 0.570296 0.298069 0.037 Uiso 1 1 calc R U . . .
C15 C 1.0293(2) 0.3974(3) 0.3274(2) 0.0371(6) Uani 1 1 d . . . . .
H15 H 1.098326 0.423117 0.261587 0.045 Uiso 1 1 calc R U . . .
C13 C 0.9309(2) 0.2329(3) 0.4950(3) 0.0352(6) Uani 1 1 d . . . . .
H13 H 0.931874 0.145948 0.543263 0.042 Uiso 1 1 calc R U . . .
C24 C 0.0693(3) 0.9791(3) 0.8206(2) 0.0362(6) Uani 1 1 d . . . . .
H24A H 0.048280 0.968872 0.912444 0.043 Uiso 1 1 calc R U . . .
H24B H -0.016633 0.970008 0.780933 0.043 Uiso 1 1 calc R U . . .
C26 C 0.2035(2) 0.4802(3) 1.0094(2) 0.0363(6) Uani 1 1 d . . . . .
H26A H 0.147811 0.416722 0.980677 0.055 Uiso 1 1 calc R U . . .
H26B H 0.143585 0.543117 1.043790 0.055 Uiso 1 1 calc R U . . .
H26C H 0.260724 0.433927 1.074835 0.055 Uiso 1 1 calc R U . . .
C25 C 0.1314(3) 1.1107(3) 0.7675(3) 0.0506(7) Uani 1 1 d . . . . .
H25A H 0.151090 1.119785 0.676622 0.076 Uiso 1 1 calc R U . . .
H25B H 0.216463 1.118268 0.807305 0.076 Uiso 1 1 calc R U . . .
H25C H 0.067191 1.179946 0.783946 0.076 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
Cl1 C20 1.745(2) . ?
S1 C9 1.753(2) . ?
S1 C2 1.757(2) . ?
Cl2 C14 1.743(2) . ?
O1 C3 1.212(2) . ?
O3 C23 1.344(3) . ?
O3 C24 1.450(3) . ?
N4 C9 1.373(2) . ?
N4 C3 1.388(3) . ?
N4 C5 1.476(2) . ?
O2 C23 1.208(3) . ?
N8 C9 1.278(3) . ?
N8 C7 1.417(3) . ?
C17 C22 1.385(3) . ?
C17 C18 1.392(3) . ?
C17 C5 1.521(3) . ?
C3 C2 1.489(3) . ?
C22 C21 1.389(3) . ?
C22 H22 0.9500 . ?
C2 C10 1.344(3) . ?
C20 C21 1.381(3) . ?
C20 C19 1.384(3) . ?
C19 C18 1.385(3) . ?
C19 H19 0.9500 . ?
C18 H18 0.9500 . ?
C21 H21 0.9500 . ?
C10 C11 1.456(3) . ?
C10 H10 0.9500 . ?
C5 C6 1.522(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.346(3) . ?
C6 C23 1.484(3) . ?
C7 C26 1.499(3) . ?
C11 C12 1.402(3) . ?
C11 C16 1.403(3) . ?
C14 C15 1.369(4) . ?
C14 C13 1.381(4) . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C16 C15 1.388(3) . ?
C16 H16 0.9500 . ?
C15 H15 0.9500 . ?
C13 H13 0.9500 . ?
C24 C25 1.499(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C9 S1 C2 91.49(9) . . ?
C23 O3 C24 116.99(18) . . ?
C9 N4 C3 116.68(16) . . ?
C9 N4 C5 120.50(16) . . ?
C3 N4 C5 122.21(16) . . ?
C9 N8 C7 116.21(18) . . ?
C22 C17 C18 119.59(18) . . ?
C22 C17 C5 120.10(17) . . ?
C18 C17 C5 120.31(17) . . ?
O1 C3 N4 123.54(18) . . ?
O1 C3 C2 126.70(18) . . ?
N4 C3 C2 109.76(16) . . ?
C17 C22 C21 120.40(19) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C10 C2 C3 120.71(18) . . ?
C10 C2 S1 128.86(17) . . ?
C3 C2 S1 110.39(14) . . ?
N8 C9 N4 126.42(19) . . ?
N8 C9 S1 122.02(15) . . ?
N4 C9 S1 111.53(14) . . ?
C21 C20 C19 121.52(19) . . ?
C21 C20 Cl1 118.85(16) . . ?
C19 C20 Cl1 119.63(16) . . ?
C20 C19 C18 118.89(19) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C18 C17 120.54(19) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C21 C22 119.06(19) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C2 C10 C11 129.6(2) . . ?
C2 C10 H10 115.2 . . ?
C11 C10 H10 115.2 . . ?
N4 C5 C17 109.81(16) . . ?
N4 C5 C6 107.85(16) . . ?
C17 C5 C6 113.20(16) . . ?
N4 C5 H5 108.6 . . ?
C17 C5 H5 108.6 . . ?
C6 C5 H5 108.6 . . ?
C7 C6 C23 123.47(19) . . ?
C7 C6 C5 121.46(19) . . ?
C23 C6 C5 114.97(18) . . ?
C6 C7 N8 122.56(19) . . ?
C6 C7 C26 126.1(2) . . ?
N8 C7 C26 111.33(19) . . ?
C12 C11 C16 117.5(2) . . ?
C12 C11 C10 124.0(2) . . ?
C16 C11 C10 118.4(2) . . ?
O2 C23 O3 122.9(2) . . ?
O2 C23 C6 127.0(2) . . ?
O3 C23 C6 110.13(18) . . ?
C15 C14 C13 121.3(2) . . ?
C15 C14 Cl2 119.53(19) . . ?
C13 C14 Cl2 119.2(2) . . ?
C13 C12 C11 121.6(2) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C15 C16 C11 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C14 C13 C12 118.9(2) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
O3 C24 C25 107.2(2) . . ?
O3 C24 H24A 110.3 . . ?
C25 C24 H24A 110.3 . . ?
O3 C24 H24B 110.3 . . ?
C25 C24 H24B 110.3 . . ?
H24A C24 H24B 108.5 . . ?
C7 C26 H26A 109.5 . . ?
C7 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C7 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C9 N4 C3 O1 177.98(18) . . . . ?
C5 N4 C3 O1 -10.9(3) . . . . ?
C9 N4 C3 C2 -2.5(2) . . . . ?
C5 N4 C3 C2 168.61(16) . . . . ?
C18 C17 C22 C21 0.2(3) . . . . ?
C5 C17 C22 C21 -179.24(19) . . . . ?
O1 C3 C2 C10 1.3(3) . . . . ?
N4 C3 C2 C10 -178.19(18) . . . . ?
O1 C3 C2 S1 179.13(17) . . . . ?
N4 C3 C2 S1 -0.40(19) . . . . ?
C9 S1 C2 C10 179.8(2) . . . . ?
C9 S1 C2 C3 2.26(14) . . . . ?
C7 N8 C9 N4 3.7(3) . . . . ?
C7 N8 C9 S1 -173.99(14) . . . . ?
C3 N4 C9 N8 -173.62(19) . . . . ?
C5 N4 C9 N8 15.1(3) . . . . ?
C3 N4 C9 S1 4.2(2) . . . . ?
C5 N4 C9 S1 -167.00(14) . . . . ?
C2 S1 C9 N8 174.34(18) . . . . ?
C2 S1 C9 N4 -3.64(15) . . . . ?
C21 C20 C19 C18 0.0(3) . . . . ?
Cl1 C20 C19 C18 179.88(16) . . . . ?
C20 C19 C18 C17 0.6(3) . . . . ?
C22 C17 C18 C19 -0.7(3) . . . . ?
C5 C17 C18 C19 178.69(18) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
Cl1 C20 C21 C22 179.58(16) . . . . ?
C17 C22 C21 C20 0.5(3) . . . . ?
C3 C2 C10 C11 178.04(19) . . . . ?
S1 C2 C10 C11 0.7(3) . . . . ?
C9 N4 C5 C17 98.9(2) . . . . ?
C3 N4 C5 C17 -71.8(2) . . . . ?
C9 N4 C5 C6 -24.9(2) . . . . ?
C3 N4 C5 C6 164.38(17) . . . . ?
C22 C17 C5 N4 107.7(2) . . . . ?
C18 C17 C5 N4 -71.7(2) . . . . ?
C22 C17 C5 C6 -131.7(2) . . . . ?
C18 C17 C5 C6 48.9(2) . . . . ?
N4 C5 C6 C7 19.9(3) . . . . ?
C17 C5 C6 C7 -101.8(2) . . . . ?
N4 C5 C6 C23 -163.61(16) . . . . ?
C17 C5 C6 C23 74.7(2) . . . . ?
C23 C6 C7 N8 179.58(18) . . . . ?
C5 C6 C7 N8 -4.2(3) . . . . ?
C23 C6 C7 C26 0.3(3) . . . . ?
C5 C6 C7 C26 176.5(2) . . . . ?
C9 N8 C7 C6 -9.0(3) . . . . ?
C9 N8 C7 C26 170.32(19) . . . . ?
C2 C10 C11 C12 12.6(3) . . . . ?
C2 C10 C11 C16 -166.6(2) . . . . ?
C24 O3 C23 O2 4.9(3) . . . . ?
C24 O3 C23 C6 -174.27(17) . . . . ?
C7 C6 C23 O2 -3.1(3) . . . . ?
C5 C6 C23 O2 -179.5(2) . . . . ?
C7 C6 C23 O3 176.04(19) . . . . ?
C5 C6 C23 O3 -0.4(2) . . . . ?
C16 C11 C12 C13 1.7(3) . . . . ?
C10 C11 C12 C13 -177.5(2) . . . . ?
C12 C11 C16 C15 -2.5(3) . . . . ?
C10 C11 C16 C15 176.8(2) . . . . ?
C13 C14 C15 C16 1.3(4) . . . . ?
Cl2 C14 C15 C16 -178.05(18) . . . . ?
C11 C16 C15 C14 1.0(3) . . . . ?
C15 C14 C13 C12 -2.0(4) . . . . ?
Cl2 C14 C13 C12 177.33(18) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C23 O3 C24 C25 157.8(2) . . . . ?

_refine_diff_density_max         1.458
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_an157
_database_code_depnum_ccdc_archive 'CCDC 2451732'
loop_
_audit_author_name
_audit_author_address
'Igor Litvinov'
;Arbuzov Institute of Organic and Physical Chemistry RAS
Russia
;
_audit_update_record             
;
2025-07-02 deposited with the CCDC.	2025-09-16 downloaded from the CCDC.
;
_audit_creation_date             2025-04-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 Br Cl N2 O3 S'
_chemical_formula_sum            'C23 H18 Br Cl N2 O3 S'
_chemical_formula_weight         517.81
_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 0.0027 0.0018 '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 -0.6406 2.7114 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1462 0.1783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0051 0.0037 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0094 0.0069 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1230 0.1390 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4140(19)
_cell_length_b                   10.970(2)
_cell_length_c                   20.797(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.98(3)
_cell_angle_gamma                90
_cell_volume                     2139.6(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    123
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.848
_cell_measurement_theta_min      2.082
_shelx_estimated_absorpt_T_max   0.633
_shelx_estimated_absorpt_T_min   0.519
_exptl_absorpt_coefficient_mu    2.515
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13283
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        26.848
_diffrn_reflns_theta_max         26.995
_diffrn_reflns_theta_min         2.082
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  Synchro
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7527
_diffrn_source                   synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3294
_reflns_number_total             3807
_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       'XDS (Kabsch, 2010)'
_computing_data_collection       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+1.3859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0908
_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 Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C20(H20), C18(H18), C12(H12), C21(H21), C10(H10), C14(H14),
 C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C25(H25A,H25B,H25C)
;
_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 0.67841(3) 0.65040(3) 0.88099(2) 0.02989(12) Uani 1 1 d . . . . .
Cl1 Cl 1.08256(7) 0.22651(6) 0.42047(4) 0.02952(18) Uani 1 1 d . . . . .
S1 S 0.56723(7) 0.71840(6) 0.47764(3) 0.02423(17) Uani 1 1 d . . . . .
O1 O 0.5564(2) 0.52154(17) 0.63009(9) 0.0262(4) Uani 1 1 d . . . . .
O2 O 0.1379(2) 0.96874(18) 0.68733(10) 0.0316(5) Uani 1 1 d . . . . .
N4 N 0.4650(2) 0.7009(2) 0.58922(10) 0.0201(5) Uani 1 1 d . . . . .
O3 O 0.18750(19) 0.77847(17) 0.72156(9) 0.0247(4) Uani 1 1 d . . . . .
C22 C 0.5970(3) 0.8754(2) 0.69167(14) 0.0241(6) Uani 1 1 d . . . . .
H22 H 0.581283 0.922198 0.653284 0.029 Uiso 1 1 calc R . . . .
C17 C 0.5140(3) 0.7731(2) 0.70025(13) 0.0205(5) Uani 1 1 d . . . . .
C26 C 0.1911(3) 1.0018(3) 0.55142(14) 0.0277(6) Uani 1 1 d . . . . .
H26A H 0.245631 1.076286 0.545192 0.042 Uiso 1 1 calc GR . . . .
H26B H 0.123658 1.016323 0.583936 0.042 Uiso 1 1 calc GR . . . .
H26C H 0.138575 0.978473 0.510512 0.042 Uiso 1 1 calc GR . . . .
N8 N 0.3809(2) 0.8699(2) 0.52519(11) 0.0224(5) Uani 1 1 d . . . . .
C11 C 0.8055(3) 0.4858(2) 0.46402(13) 0.0231(6) Uani 1 1 d . . . . .
C7 C 0.2914(3) 0.9009(2) 0.57383(13) 0.0223(6) Uani 1 1 d . . . . .
C20 C 0.7260(3) 0.8424(2) 0.79501(14) 0.0261(6) Uani 1 1 d . . . . .
H20 H 0.797801 0.865836 0.827567 0.031 Uiso 1 1 calc R . . . .
C5 C 0.3984(3) 0.7369(2) 0.64767(13) 0.0201(5) Uani 1 1 d . . . . .
H5 H 0.343889 0.666044 0.663164 0.024 Uiso 1 1 calc R . . . .
C13 C 0.9793(3) 0.3589(2) 0.41764(14) 0.0251(6) Uani 1 1 d . . . . .
C18 C 0.5366(3) 0.7032(2) 0.75637(13) 0.0209(5) Uani 1 1 d . . . . .
H18 H 0.481046 0.632486 0.762442 0.025 Uiso 1 1 calc R . . . .
C12 C 0.8894(3) 0.3800(2) 0.46590(13) 0.0232(6) Uani 1 1 d . . . . .
H12 H 0.884670 0.323008 0.500054 0.028 Uiso 1 1 calc R . . . .
C21 C 0.7027(3) 0.9097(3) 0.73876(15) 0.0282(6) Uani 1 1 d . . . . .
H21 H 0.759376 0.979565 0.732417 0.034 Uiso 1 1 calc R . . . .
C19 C 0.6424(3) 0.7399(2) 0.80305(13) 0.0230(6) Uani 1 1 d . . . . .
C6 C 0.2952(3) 0.8418(2) 0.63109(14) 0.0219(6) Uani 1 1 d . . . . .
C10 C 0.7163(3) 0.5056(2) 0.51718(13) 0.0231(6) Uani 1 1 d . . . . .
H10 H 0.726763 0.445731 0.550269 0.028 Uiso 1 1 calc R . . . .
C3 C 0.5476(3) 0.5969(2) 0.58725(13) 0.0212(5) Uani 1 1 d . . . . .
C9 C 0.4582(3) 0.7742(2) 0.53506(13) 0.0215(6) Uani 1 1 d . . . . .
C14 C 0.9895(3) 0.4400(3) 0.36771(14) 0.0278(6) Uani 1 1 d . . . . .
H14 H 1.052618 0.424631 0.335381 0.033 Uiso 1 1 calc R . . . .
C15 C 0.9062(3) 0.5445(3) 0.36537(14) 0.0303(6) Uani 1 1 d . . . . .
H15 H 0.911713 0.600769 0.330967 0.036 Uiso 1 1 calc R . . . .
C23 C 0.1994(3) 0.8730(2) 0.68135(14) 0.0236(6) Uani 1 1 d . . . . .
C16 C 0.8150(3) 0.5674(3) 0.41269(14) 0.0269(6) Uani 1 1 d . . . . .
H16 H 0.758362 0.639201 0.410389 0.032 Uiso 1 1 calc R . . . .
C24 C 0.0846(3) 0.7934(3) 0.76892(14) 0.0291(6) Uani 1 1 d . . . . .
H24A H -0.011997 0.806242 0.747160 0.035 Uiso 1 1 calc R . . . .
H24B H 0.109714 0.864749 0.796765 0.035 Uiso 1 1 calc R . . . .
C25 C 0.0883(3) 0.6788(3) 0.80863(15) 0.0345(7) Uani 1 1 d . . . . .
H25A H 0.068563 0.608438 0.780216 0.052 Uiso 1 1 calc GR . . . .
H25B H 0.016007 0.683562 0.839709 0.052 Uiso 1 1 calc GR . . . .
H25C H 0.182837 0.669655 0.831855 0.052 Uiso 1 1 calc GR . . . .
C2 C 0.6219(3) 0.5943(2) 0.52724(13) 0.0220(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C19 1.900(3) . ?
Cl1 C13 1.745(3) . ?
S1 C9 1.751(3) . ?
S1 C2 1.758(3) . ?
O1 C3 1.213(3) . ?
O2 C23 1.211(3) . ?
N4 C5 1.470(4) . ?
N4 C3 1.383(3) . ?
N4 C9 1.381(3) . ?
O3 C23 1.343(3) . ?
O3 C24 1.449(3) . ?
C22 H22 0.9500 . ?
C22 C17 1.388(4) . ?
C22 C21 1.386(4) . ?
C17 C5 1.527(3) . ?
C17 C18 1.397(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C26 C7 1.502(4) . ?
N8 C7 1.413(4) . ?
N8 C9 1.284(3) . ?
C11 C12 1.403(4) . ?
C11 C10 1.461(4) . ?
C11 C16 1.402(4) . ?
C7 C6 1.353(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(4) . ?
C20 C19 1.390(4) . ?
C5 H5 1.0000 . ?
C5 C6 1.526(3) . ?
C13 C12 1.388(4) . ?
C13 C14 1.377(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(4) . ?
C12 H12 0.9500 . ?
C21 H21 0.9500 . ?
C6 C23 1.478(4) . ?
C10 H10 0.9500 . ?
C10 C2 1.347(4) . ?
C3 C2 1.483(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(4) . ?
C16 H16 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.503(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C9 S1 C2 91.69(13) . . ?
C3 N4 C5 121.9(2) . . ?
C9 N4 C5 121.7(2) . . ?
C9 N4 C3 116.2(2) . . ?
C23 O3 C24 115.7(2) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C17 120.4(3) . . ?
C22 C17 C5 119.5(2) . . ?
C22 C17 C18 120.3(2) . . ?
C18 C17 C5 120.2(2) . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C7 C26 H26A 109.5 . . ?
C7 C26 H26B 109.5 . . ?
C7 C26 H26C 109.5 . . ?
C9 N8 C7 116.6(2) . . ?
C12 C11 C10 117.5(3) . . ?
C16 C11 C12 118.5(3) . . ?
C16 C11 C10 124.1(2) . . ?
N8 C7 C26 110.7(2) . . ?
C6 C7 C26 126.4(3) . . ?
C6 C7 N8 122.9(2) . . ?
C21 C20 H20 120.6 . . ?
C21 C20 C19 118.9(2) . . ?
C19 C20 H20 120.6 . . ?
N4 C5 C17 109.5(2) . . ?
N4 C5 H5 109.0 . . ?
N4 C5 C6 109.0(2) . . ?
C17 C5 H5 109.0 . . ?
C6 C5 C17 111.5(2) . . ?
C6 C5 H5 109.0 . . ?
C12 C13 Cl1 119.2(2) . . ?
C14 C13 Cl1 119.2(2) . . ?
C14 C13 C12 121.6(3) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 C17 118.2(2) . . ?
C19 C18 H18 120.9 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.1 . . ?
C22 C21 H21 119.9 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C20 C19 Br1 117.4(2) . . ?
C18 C19 Br1 120.7(2) . . ?
C18 C19 C20 121.9(3) . . ?
C7 C6 C5 121.8(3) . . ?
C7 C6 C23 122.7(2) . . ?
C23 C6 C5 115.5(2) . . ?
C11 C10 H10 114.5 . . ?
C2 C10 C11 130.9(3) . . ?
C2 C10 H10 114.5 . . ?
O1 C3 N4 122.9(3) . . ?
O1 C3 C2 126.7(2) . . ?
N4 C3 C2 110.4(2) . . ?
N4 C9 S1 111.38(19) . . ?
N8 C9 S1 122.3(2) . . ?
N8 C9 N4 126.3(3) . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 118.9(3) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
O2 C23 O3 122.6(3) . . ?
O2 C23 C6 126.8(3) . . ?
O3 C23 C6 110.6(2) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.7(3) . . ?
C15 C16 H16 119.7 . . ?
O3 C24 H24A 110.3 . . ?
O3 C24 H24B 110.3 . . ?
O3 C24 C25 107.1(2) . . ?
H24A C24 H24B 108.6 . . ?
C25 C24 H24A 110.3 . . ?
C25 C24 H24B 110.3 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C10 C2 S1 129.2(2) . . ?
C10 C2 C3 120.7(2) . . ?
C3 C2 S1 110.10(19) . . ?

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
Cl1 C13 C12 C11 -179.74(19) . . . . ?
Cl1 C13 C14 C15 179.4(2) . . . . ?
O1 C3 C2 S1 176.4(2) . . . . ?
O1 C3 C2 C10 -3.9(4) . . . . ?
N4 C5 C6 C7 -10.5(3) . . . . ?
N4 C5 C6 C23 168.8(2) . . . . ?
N4 C3 C2 S1 -4.5(3) . . . . ?
N4 C3 C2 C10 175.3(2) . . . . ?
C22 C17 C5 N4 65.7(3) . . . . ?
C22 C17 C5 C6 -55.0(3) . . . . ?
C22 C17 C18 C19 0.7(4) . . . . ?
C17 C22 C21 C20 -0.3(4) . . . . ?
C17 C5 C6 C7 110.4(3) . . . . ?
C17 C5 C6 C23 -70.3(3) . . . . ?
C17 C18 C19 Br1 179.46(19) . . . . ?
C17 C18 C19 C20 -0.6(4) . . . . ?
C26 C7 C6 C5 177.6(2) . . . . ?
C26 C7 C6 C23 -1.7(4) . . . . ?
N8 C7 C6 C5 0.5(4) . . . . ?
N8 C7 C6 C23 -178.8(2) . . . . ?
C11 C10 C2 S1 2.1(4) . . . . ?
C11 C10 C2 C3 -177.6(2) . . . . ?
C7 N8 C9 S1 176.27(18) . . . . ?
C7 N8 C9 N4 -1.9(4) . . . . ?
C7 C6 C23 O2 -21.9(4) . . . . ?
C7 C6 C23 O3 158.0(2) . . . . ?
C5 N4 C3 O1 9.3(4) . . . . ?
C5 N4 C3 C2 -169.9(2) . . . . ?
C5 N4 C9 S1 171.70(18) . . . . ?
C5 N4 C9 N8 -10.0(4) . . . . ?
C5 C17 C18 C19 -179.6(2) . . . . ?
C5 C6 C23 O2 158.8(3) . . . . ?
C5 C6 C23 O3 -21.3(3) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C18 C17 C5 N4 -114.0(3) . . . . ?
C18 C17 C5 C6 125.4(3) . . . . ?
C12 C11 C10 C2 -177.0(3) . . . . ?
C12 C11 C16 C15 -0.6(4) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C21 C22 C17 C5 -179.9(3) . . . . ?
C21 C22 C17 C18 -0.3(4) . . . . ?
C21 C20 C19 Br1 180.0(2) . . . . ?
C21 C20 C19 C18 0.0(4) . . . . ?
C19 C20 C21 C22 0.5(4) . . . . ?
C10 C11 C12 C13 -177.9(2) . . . . ?
C10 C11 C16 C15 177.5(2) . . . . ?
C3 N4 C5 C17 67.3(3) . . . . ?
C3 N4 C5 C6 -170.5(2) . . . . ?
C3 N4 C9 S1 -3.1(3) . . . . ?
C3 N4 C9 N8 175.2(2) . . . . ?
C9 S1 C2 C10 -177.3(3) . . . . ?
C9 S1 C2 C3 2.39(19) . . . . ?
C9 N4 C5 C17 -107.2(2) . . . . ?
C9 N4 C5 C6 14.9(3) . . . . ?
C9 N4 C3 O1 -175.9(2) . . . . ?
C9 N4 C3 C2 4.9(3) . . . . ?
C9 N8 C7 C26 -171.0(2) . . . . ?
C9 N8 C7 C6 6.6(4) . . . . ?
C14 C13 C12 C11 0.5(4) . . . . ?
C14 C15 C16 C11 0.2(4) . . . . ?
C23 O3 C24 C25 -179.9(2) . . . . ?
C16 C11 C12 C13 0.2(4) . . . . ?
C16 C11 C10 C2 5.0(4) . . . . ?
C24 O3 C23 O2 6.2(4) . . . . ?
C24 O3 C23 C6 -173.8(2) . . . . ?
C2 S1 C9 N4 0.25(19) . . . . ?
C2 S1 C9 N8 -178.2(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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2451727'
loop_
_audit_author_name
_audit_author_address
'Igor Litvinov'
;Arbuzov Institute of Organic and Physical Chemistry RAS
Russia
;
_audit_update_record             
;
2025-05-16 deposited with the CCDC.	2025-09-16 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 Br Cl N2 O3 S'
_chemical_formula_sum            'C23 H18 Br Cl N2 O3 S'
_chemical_formula_weight         517.81

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8690(6)
_cell_length_b                   10.4780(7)
_cell_length_c                   10.8827(8)
_cell_angle_alpha                77.635(2)
_cell_angle_beta                 85.089(2)
_cell_angle_gamma                88.968(2)
_cell_volume                     1095.21(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      33.99


_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    2.122
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.6384

_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS DIAMOND'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29784
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.990
_diffrn_reflns_theta_max         31.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7583
_reflns_number_gt                6059
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²+0.4697P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7583
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.36668(17) 0.45427(17) 0.43193(15) 0.0143(3) Uani 1 1 d . . . . .
C3 C 0.45788(17) 0.34053(17) 0.42731(15) 0.0138(3) Uani 1 1 d . . . . .
C5 C 0.62262(17) 0.26077(16) 0.27276(15) 0.0128(3) Uani 1 1 d . . . . .
H5 H 0.671537 0.211967 0.345231 0.015 Uiso 1 1 calc R U . . .
C6 C 0.72698(17) 0.32586(17) 0.16815(16) 0.0153(3) Uani 1 1 d . . . . .
C7 C 0.70852(17) 0.44867(18) 0.10227(16) 0.0169(3) Uani 1 1 d . . . . .
C8A C 0.52522(17) 0.48304(16) 0.23528(16) 0.0145(3) Uani 1 1 d . . . . .
C9 C 0.27488(18) 0.45318(18) 0.53090(16) 0.0161(3) Uani 1 1 d . . . . .
H9 H 0.276225 0.377383 0.596786 0.019 Uiso 1 1 calc R U . . .
C10 C 0.17368(17) 0.55082(19) 0.55222(16) 0.0171(3) Uani 1 1 d . . . . .
C11 C 0.07118(19) 0.5143(2) 0.65091(17) 0.0220(4) Uani 1 1 d . . . . .
H11 H 0.072588 0.429488 0.703712 0.026 Uiso 1 1 calc R U . . .
C12 C -0.0319(2) 0.6005(2) 0.67216(18) 0.0261(4) Uani 1 1 d . . . . .
H12 H -0.101764 0.574172 0.738008 0.031 Uiso 1 1 calc R U . . .
C13 C -0.03270(19) 0.7241(2) 0.59761(19) 0.0237(4) Uani 1 1 d . . . . .
C14 C 0.0692(2) 0.7648(2) 0.5023(2) 0.0250(4) Uani 1 1 d . . . . .
H14 H 0.069138 0.851274 0.452774 0.030 Uiso 1 1 calc R U . . .
C15 C 0.17119(19) 0.6784(2) 0.48004(19) 0.0228(4) Uani 1 1 d . . . . .
H15 H 0.240927 0.706207 0.414412 0.027 Uiso 1 1 calc R U . . .
C16 C 0.53111(16) 0.16636(16) 0.23053(15) 0.0124(3) Uani 1 1 d . . . . .
C17 C 0.51186(18) 0.04030(17) 0.30165(16) 0.0161(3) Uani 1 1 d . . . . .
H17 H 0.556643 0.013104 0.376776 0.019 Uiso 1 1 calc R U . . .
C18 C 0.42785(18) -0.04630(17) 0.26405(16) 0.0171(3) Uani 1 1 d . . . . .
H18 H 0.415310 -0.132801 0.312430 0.021 Uiso 1 1 calc R U . . .
C19 C 0.36258(17) -0.00469(17) 0.15492(16) 0.0148(3) Uani 1 1 d . . . . .
C20 C 0.38028(18) 0.12001(18) 0.08197(16) 0.0164(3) Uani 1 1 d . . . . .
H20 H 0.334845 0.146926 0.007189 0.020 Uiso 1 1 calc R U . . .
C21 C 0.46575(17) 0.20515(17) 0.12009(16) 0.0159(3) Uani 1 1 d . . . . .
H21 H 0.479852 0.290855 0.070310 0.019 Uiso 1 1 calc R U . . .
C22 C 0.84275(17) 0.24193(18) 0.13871(17) 0.0174(3) Uani 1 1 d . . . . .
C23 C 0.9273(2) 0.0236(2) 0.1897(2) 0.0242(4) Uani 1 1 d . . . . .
H23A H 1.009441 0.028364 0.234830 0.029 Uiso 1 1 calc R U . . .
H23B H 0.954879 0.037377 0.098228 0.029 Uiso 1 1 calc R U . . .
C24 C 0.8595(2) -0.1065(2) 0.2361(2) 0.0334(5) Uani 1 1 d . . . . .
H24A H 0.830309 -0.117798 0.326114 0.050 Uiso 1 1 calc R U . . .
H24B H 0.923744 -0.175979 0.223615 0.050 Uiso 1 1 calc R U . . .
H24C H 0.780169 -0.111005 0.188852 0.050 Uiso 1 1 calc R U . . .
C25 C 0.7985(2) 0.5201(2) -0.00761(19) 0.0267(4) Uani 1 1 d . . . . .
H25A H 0.856043 0.581778 0.020511 0.040 Uiso 1 1 calc R U . . .
H25B H 0.742443 0.568052 -0.072357 0.040 Uiso 1 1 calc R U . . .
H25C H 0.856113 0.457389 -0.042950 0.040 Uiso 1 1 calc R U . . .
Br1 Br 0.24676(2) -0.12332(2) 0.10437(2) 0.01856(6) Uani 1 1 d . . . . .
Cl1 Cl -0.16456(5) 0.83071(6) 0.62236(5) 0.03281(12) Uani 1 1 d . . . . .
N4 N 0.53997(14) 0.36431(14) 0.31468(13) 0.0128(3) Uani 1 1 d . . . . .
N8 N 0.59801(15) 0.52797(15) 0.13188(14) 0.0176(3) Uani 1 1 d . . . . .
O3 O 0.46238(14) 0.24107(13) 0.50718(11) 0.0186(3) Uani 1 1 d . . . . .
O22 O 0.93612(14) 0.27205(14) 0.05870(15) 0.0278(3) Uani 1 1 d . . . . .
O23 O 0.82924(13) 0.12218(13) 0.21413(12) 0.0209(3) Uani 1 1 d . . . . .
S1 S 0.39452(4) 0.57532(4) 0.29295(4) 0.01624(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C9 1.345(2) . ?
C2 C3 1.487(2) . ?
C2 S1 1.7584(17) . ?
C3 O3 1.208(2) . ?
C3 N4 1.388(2) . ?
C5 N4 1.472(2) . ?
C5 C16 1.518(2) . ?
C5 C6 1.521(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.350(3) . ?
C6 C22 1.484(2) . ?
C7 N8 1.416(2) . ?
C7 C25 1.496(2) . ?
C8A N8 1.285(2) . ?
C8A N4 1.368(2) . ?
C8A S1 1.7518(18) . ?
C9 C10 1.457(3) . ?
C9 H9 0.9500 . ?
C10 C15 1.399(3) . ?
C10 C11 1.405(2) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 Cl1 1.740(2) . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.388(2) . ?
C16 C21 1.393(2) . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(2) . ?
C19 Br1 1.8990(17) . ?
C20 C21 1.387(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O22 1.209(2) . ?
C22 O23 1.346(2) . ?
C23 O23 1.453(2) . ?
C23 C24 1.497(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C9 C2 C3 120.81(15) . . ?
C9 C2 S1 128.57(14) . . ?
C3 C2 S1 110.57(12) . . ?
O3 C3 N4 123.61(16) . . ?
O3 C3 C2 126.79(15) . . ?
N4 C3 C2 109.60(14) . . ?
N4 C5 C16 109.77(13) . . ?
N4 C5 C6 107.88(13) . . ?
C16 C5 C6 112.66(13) . . ?
N4 C5 H5 108.8 . . ?
C16 C5 H5 108.8 . . ?
C6 C5 H5 108.8 . . ?
C7 C6 C22 123.27(16) . . ?
C7 C6 C5 121.21(15) . . ?
C22 C6 C5 115.36(15) . . ?
C6 C7 N8 122.67(15) . . ?
C6 C7 C25 126.35(17) . . ?
N8 C7 C25 110.98(16) . . ?
N8 C8A N4 126.39(16) . . ?
N8 C8A S1 121.71(14) . . ?
N4 C8A S1 111.88(12) . . ?
C2 C9 C10 129.70(17) . . ?
C2 C9 H9 115.1 . . ?
C10 C9 H9 115.1 . . ?
C15 C10 C11 117.80(17) . . ?
C15 C10 C9 124.22(16) . . ?
C11 C10 C9 117.98(17) . . ?
C12 C11 C10 120.82(19) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 119.74(18) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.94(19) . . ?
C12 C13 Cl1 119.53(16) . . ?
C14 C13 Cl1 119.52(17) . . ?
C15 C14 C13 119.4(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C10 121.28(18) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C17 C16 C21 119.32(16) . . ?
C17 C16 C5 120.25(14) . . ?
C21 C16 C5 120.43(15) . . ?
C18 C17 C16 120.59(15) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 118.92(16) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C20 C19 C18 121.75(16) . . ?
C20 C19 Br1 119.48(12) . . ?
C18 C19 Br1 118.77(13) . . ?
C19 C20 C21 118.67(15) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C20 C21 C16 120.73(16) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
O22 C22 O23 123.19(17) . . ?
O22 C22 C6 126.91(18) . . ?
O23 C22 C6 109.89(15) . . ?
O23 C23 C24 107.07(16) . . ?
O23 C23 H23A 110.3 . . ?
C24 C23 H23A 110.3 . . ?
O23 C23 H23B 110.3 . . ?
C24 C23 H23B 110.3 . . ?
H23A C23 H23B 108.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 C25 H25A 109.5 . . ?
C7 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C7 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C8A N4 C3 116.65(14) . . ?
C8A N4 C5 120.73(13) . . ?
C3 N4 C5 121.92(14) . . ?
C8A N8 C7 115.95(15) . . ?
C22 O23 C23 117.08(15) . . ?
C8A S1 C2 91.17(8) . . ?

_refine_diff_density_max         1.149
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.094

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2451725'
loop_
_audit_author_name
_audit_author_address
'Igor Litvinov'
;Arbuzov Institute of Organic and Physical Chemistry RAS
Russia
;
_audit_update_record             
;
2025-05-16 deposited with the CCDC.	2025-09-16 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 Br2 N2 O3 S'
_chemical_formula_sum            'C23 H18 Br2 N2 O3 S'
_chemical_formula_weight         562.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6630(4)
_cell_length_b                   10.8463(6)
_cell_length_c                   13.3597(7)
_cell_angle_alpha                105.308(2)
_cell_angle_beta                 93.899(2)
_cell_angle_gamma                91.273(2)
_cell_volume                     1067.59(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    105(2)
_cell_measurement_reflns_used    9568
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      38.01


_exptl_crystal_description       plate
_exptl_crystal_colour            yelow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    3.924
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.4090

_exptl_absorpt_correction_T_max  0.7483
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      105(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS DIAMOND'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            104500
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.948
_diffrn_reflns_theta_max         31.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7400
_reflns_number_gt                6502
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²+0.7677P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7400
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.1998(2) 0.55926(15) 0.35786(12) 0.0104(3) Uani 1 1 d . . . . .
C3 C 0.1440(2) 0.68002(15) 0.42842(12) 0.0101(3) Uani 1 1 d . . . . .
C5 C 0.1402(2) 0.78495(15) 0.61917(12) 0.0102(3) Uani 1 1 d . . . . .
H5 H 0.025971 0.824042 0.608200 0.012 Uiso 1 1 calc R U . . .
C6 C 0.1409(2) 0.74118(15) 0.71892(12) 0.0110(3) Uani 1 1 d . . . . .
C7 C 0.1909(2) 0.62353(16) 0.72257(12) 0.0117(3) Uani 1 1 d . . . . .
C8A C 0.2172(2) 0.55940(15) 0.54668(13) 0.0110(3) Uani 1 1 d . . . . .
C9 C 0.2072(2) 0.54817(16) 0.25561(13) 0.0133(3) Uani 1 1 d . . . . .
H9 H 0.168223 0.619863 0.233362 0.016 Uiso 1 1 calc R U . . .
C10 C 0.2656(2) 0.44353(16) 0.17356(13) 0.0130(3) Uani 1 1 d . . . . .
C11 C 0.3072(2) 0.32339(17) 0.18623(13) 0.0155(3) Uani 1 1 d . . . . .
H11 H 0.292030 0.305434 0.251028 0.019 Uiso 1 1 calc R U . . .
C12 C 0.3704(3) 0.22960(17) 0.10592(14) 0.0173(3) Uani 1 1 d . . . . .
H12 H 0.399892 0.148802 0.115818 0.021 Uiso 1 1 calc R U . . .
C13 C 0.3895(2) 0.25625(18) 0.01100(14) 0.0160(3) Uani 1 1 d . . . . .
C14 C 0.3447(3) 0.37250(19) -0.00544(14) 0.0197(3) Uani 1 1 d . . . . .
H14 H 0.355584 0.388519 -0.071345 0.024 Uiso 1 1 calc R U . . .
C15 C 0.2833(3) 0.46565(18) 0.07594(14) 0.0188(3) Uani 1 1 d . . . . .
H15 H 0.252818 0.545837 0.065158 0.023 Uiso 1 1 calc R U . . .
C16 C 0.2885(2) 0.88306(15) 0.62509(12) 0.0103(3) Uani 1 1 d . . . . .
C17 C 0.2554(2) 1.00690(15) 0.61983(13) 0.0118(3) Uani 1 1 d . . . . .
H17 H 0.138741 1.032260 0.610953 0.014 Uiso 1 1 calc R U . . .
C18 C 0.3963(2) 1.09276(16) 0.62782(13) 0.0133(3) Uani 1 1 d . . . . .
C19 C 0.5679(2) 1.05762(17) 0.63836(14) 0.0156(3) Uani 1 1 d . . . . .
H19 H 0.662183 1.117466 0.642242 0.019 Uiso 1 1 calc R U . . .
C20 C 0.6001(2) 0.93416(17) 0.64316(15) 0.0171(3) Uani 1 1 d . . . . .
H20 H 0.717130 0.908844 0.650583 0.020 Uiso 1 1 calc R U . . .
C21 C 0.4608(2) 0.84697(16) 0.63710(14) 0.0152(3) Uani 1 1 d . . . . .
H21 H 0.483149 0.762567 0.641177 0.018 Uiso 1 1 calc R U . . .
C22 C 0.0973(2) 0.83839(16) 0.81360(13) 0.0135(3) Uani 1 1 d . . . . .
C23 C -0.0117(3) 1.04478(17) 0.87731(14) 0.0165(3) Uani 1 1 d . . . . .
H23A H 0.084729 1.057629 0.932751 0.020 Uiso 1 1 calc R U . . .
H23B H -0.121473 1.025201 0.906090 0.020 Uiso 1 1 calc R U . . .
C24 C -0.0293(3) 1.16365(18) 0.83993(15) 0.0204(4) Uani 1 1 d . . . . .
H24A H 0.081191 1.183710 0.813616 0.031 Uiso 1 1 calc R U . . .
H24B H -0.057315 1.235280 0.897808 0.031 Uiso 1 1 calc R U . . .
H24C H -0.123223 1.149304 0.784041 0.031 Uiso 1 1 calc R U . . .
C25 C 0.2062(3) 0.57361(17) 0.81747(13) 0.0154(3) Uani 1 1 d . . . . .
H25A H 0.324803 0.592905 0.851400 0.023 Uiso 1 1 calc R U . . .
H25B H 0.182640 0.480809 0.796891 0.023 Uiso 1 1 calc R U . . .
H25C H 0.121195 0.614567 0.865997 0.023 Uiso 1 1 calc R U . . .
Br13 Br 0.47752(3) 0.13207(2) -0.09967(2) 0.02300(6) Uani 1 1 d . . . . .
Br18 Br 0.35238(2) 1.26458(2) 0.62932(2) 0.01756(5) Uani 1 1 d . . . . .
N4 N 0.15897(19) 0.67226(13) 0.53111(11) 0.0105(2) Uani 1 1 d . . . . .
N8 N 0.2380(2) 0.53081(14) 0.63347(11) 0.0134(3) Uani 1 1 d . . . . .
O3 O 0.09575(17) 0.77419(12) 0.40381(10) 0.0138(2) Uani 1 1 d . . . . .
O22 O 0.1216(2) 0.83059(14) 0.90196(11) 0.0258(3) Uani 1 1 d . . . . .
O23 O 0.02515(18) 0.94001(12) 0.78908(10) 0.0145(2) Uani 1 1 d . . . . .
S1 S 0.26088(6) 0.45050(4) 0.42939(3) 0.01292(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C9 1.345(2) . ?
C2 C3 1.488(2) . ?
C2 S1 1.7558(16) . ?
C3 O3 1.2107(19) . ?
C3 N4 1.394(2) . ?
C5 N4 1.473(2) . ?
C5 C16 1.523(2) . ?
C5 C6 1.528(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.353(2) . ?
C6 C22 1.481(2) . ?
C7 N8 1.414(2) . ?
C7 C25 1.503(2) . ?
C8A N8 1.278(2) . ?
C8A N4 1.374(2) . ?
C8A S1 1.7532(17) . ?
C9 C10 1.457(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.399(2) . ?
C10 C15 1.402(2) . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(3) . ?
C13 Br13 1.8920(18) . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.391(2) . ?
C16 C21 1.396(2) . ?
C17 C18 1.390(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 Br18 1.8962(16) . ?
C19 C20 1.384(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O22 1.208(2) . ?
C22 O23 1.349(2) . ?
C23 O23 1.454(2) . ?
C23 C24 1.506(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C9 C2 C3 120.43(14) . . ?
C9 C2 S1 129.12(13) . . ?
C3 C2 S1 110.34(11) . . ?
O3 C3 N4 123.16(15) . . ?
O3 C3 C2 126.83(15) . . ?
N4 C3 C2 109.99(13) . . ?
N4 C5 C16 109.72(13) . . ?
N4 C5 C6 108.53(12) . . ?
C16 C5 C6 111.41(13) . . ?
N4 C5 H5 109.0 . . ?
C16 C5 H5 109.0 . . ?
C6 C5 H5 109.0 . . ?
C7 C6 C22 121.61(15) . . ?
C7 C6 C5 122.07(14) . . ?
C22 C6 C5 116.15(14) . . ?
C6 C7 N8 122.36(14) . . ?
C6 C7 C25 126.39(15) . . ?
N8 C7 C25 111.25(14) . . ?
N8 C8A N4 126.87(15) . . ?
N8 C8A S1 121.40(13) . . ?
N4 C8A S1 111.72(12) . . ?
C2 C9 C10 130.17(16) . . ?
C2 C9 H9 114.9 . . ?
C10 C9 H9 114.9 . . ?
C11 C10 C15 118.01(16) . . ?
C11 C10 C9 124.33(15) . . ?
C15 C10 C9 117.65(15) . . ?
C12 C11 C10 121.38(16) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 118.80(17) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C14 C13 C12 121.46(17) . . ?
C14 C13 Br13 118.42(14) . . ?
C12 C13 Br13 120.12(14) . . ?
C13 C14 C15 119.00(17) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C10 121.30(17) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C17 C16 C21 119.93(15) . . ?
C17 C16 C5 121.45(14) . . ?
C21 C16 C5 118.62(14) . . ?
C18 C17 C16 118.69(15) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C19 C18 C17 121.92(15) . . ?
C19 C18 Br18 118.99(13) . . ?
C17 C18 Br18 119.05(13) . . ?
C18 C19 C20 119.13(16) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C19 C20 C21 119.97(17) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 120.34(16) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
O22 C22 O23 123.12(16) . . ?
O22 C22 C6 125.85(16) . . ?
O23 C22 C6 111.03(14) . . ?
O23 C23 C24 107.98(14) . . ?
O23 C23 H23A 110.1 . . ?
C24 C23 H23A 110.1 . . ?
O23 C23 H23B 110.1 . . ?
C24 C23 H23B 110.1 . . ?
H23A C23 H23B 108.4 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 C25 H25A 109.5 . . ?
C7 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C7 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C8A N4 C3 116.30(14) . . ?
C8A N4 C5 121.33(13) . . ?
C3 N4 C5 121.71(13) . . ?
C8A N8 C7 116.64(14) . . ?
C22 O23 C23 115.25(13) . . ?
C8A S1 C2 91.65(8) . . ?

_refine_diff_density_max         1.283
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.115

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2451734'
loop_
_audit_author_name
_audit_author_address
'Igor Litvinov'
;Arbuzov Institute of Organic and Physical Chemistry RAS
Russia
;
_audit_update_record             
;
2025-07-02 deposited with the CCDC.	2025-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 Br2 N2 O3 S'
_chemical_formula_sum            'C23 H18 Br2 N2 O3 S'
_chemical_formula_weight         562.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9689(16)
_cell_length_b                   10.4507(15)
_cell_length_c                   10.9158(19)
_cell_angle_alpha                77.441(7)
_cell_angle_beta                 85.094(7)
_cell_angle_gamma                88.691(7)
_cell_volume                     1105.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      23.79


_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03

_exptl_absorpt_coefficient_mu    3.788
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.6191

_exptl_absorpt_correction_T_max  0.7450

_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS DIAMOND'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39737
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.1140
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.918
_diffrn_reflns_theta_max         23.849
_diffrn_reflns_theta_full        23.849
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3374
_reflns_number_gt                2743
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3374
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.6281(4) 0.5462(3) 0.5706(3) 0.0172(8) Uani 1 1 d . . . . .
C3 C 0.5359(3) 0.6584(3) 0.5757(3) 0.0164(8) Uani 1 1 d . . . . .
C5 C 0.3730(3) 0.7373(3) 0.7311(3) 0.0164(8) Uani 1 1 d . . . . .
H5 H 0.323267 0.786023 0.659314 0.020 Uiso 1 1 calc R U . . .
C6 C 0.2712(3) 0.6710(3) 0.8364(3) 0.0177(8) Uani 1 1 d . . . . .
C7 C 0.2893(4) 0.5477(4) 0.9007(3) 0.0211(9) Uani 1 1 d . . . . .
C8A C 0.4711(4) 0.5149(3) 0.7678(3) 0.0181(8) Uani 1 1 d . . . . .
C9 C 0.7194(3) 0.5474(3) 0.4727(3) 0.0186(8) Uani 1 1 d . . . . .
H9 H 0.717171 0.623682 0.407066 0.022 Uiso 1 1 calc R U . . .
C10 C 0.8210(4) 0.4516(4) 0.4504(3) 0.0214(9) Uani 1 1 d . . . . .
C11 C 0.8260(4) 0.3235(3) 0.5232(4) 0.0264(9) Uani 1 1 d . . . . .
H11 H 0.758003 0.295012 0.589444 0.032 Uiso 1 1 calc R U . . .
C12 C 0.9279(4) 0.2381(4) 0.5003(4) 0.0273(9) Uani 1 1 d . . . . .
H12 H 0.929469 0.151212 0.549671 0.033 Uiso 1 1 calc R U . . .
C13 C 1.0276(4) 0.2800(4) 0.4051(4) 0.0263(9) Uani 1 1 d . . . . .
C14 C 1.0253(4) 0.4042(4) 0.3294(4) 0.0299(10) Uani 1 1 d . . . . .
H14 H 1.093106 0.431032 0.262641 0.036 Uiso 1 1 calc R U . . .
C15 C 0.9213(4) 0.4895(4) 0.3528(3) 0.0242(9) Uani 1 1 d . . . . .
H15 H 0.918764 0.575144 0.301120 0.029 Uiso 1 1 calc R U . . .
C16 C 0.4637(3) 0.8333(3) 0.7721(3) 0.0143(8) Uani 1 1 d . . . . .
C17 C 0.5278(3) 0.7941(3) 0.8819(3) 0.0186(8) Uani 1 1 d . . . . .
H17 H 0.513058 0.708492 0.932280 0.022 Uiso 1 1 calc R U . . .
C18 C 0.6133(4) 0.8787(3) 0.9191(3) 0.0206(8) Uani 1 1 d . . . . .
H18 H 0.657907 0.851716 0.994017 0.025 Uiso 1 1 calc R U . . .
C19 C 0.6323(3) 1.0028(3) 0.8452(3) 0.0152(8) Uani 1 1 d . . . . .
C20 C 0.5683(4) 1.0441(3) 0.7363(3) 0.0206(8) Uani 1 1 d . . . . .
H20 H 0.581752 1.130302 0.686915 0.025 Uiso 1 1 calc R U . . .
C21 C 0.4838(4) 0.9576(3) 0.6997(3) 0.0195(8) Uani 1 1 d . . . . .
H21 H 0.439757 0.984495 0.624481 0.023 Uiso 1 1 calc R U . . .
C22 C 0.1568(4) 0.7570(4) 0.8664(4) 0.0229(9) Uani 1 1 d . . . . .
C23 C 0.0716(4) 0.9749(4) 0.8171(4) 0.0301(10) Uani 1 1 d . . . . .
H23A H 0.045528 0.960384 0.908629 0.036 Uiso 1 1 calc R U . . .
H23B H -0.010365 0.971187 0.772853 0.036 Uiso 1 1 calc R U . . .
C24 C 0.1395(4) 1.1053(4) 0.7706(4) 0.0413(11) Uani 1 1 d . . . . .
H24A H 0.222757 1.106014 0.812200 0.062 Uiso 1 1 calc R U . . .
H24B H 0.079239 1.174945 0.789966 0.062 Uiso 1 1 calc R U . . .
H24C H 0.160931 1.120148 0.679323 0.062 Uiso 1 1 calc R U . . .
C25 C 0.2004(4) 0.4754(4) 1.0109(4) 0.0325(10) Uani 1 1 d . . . . .
H25A H 0.146078 0.538482 1.048551 0.049 Uiso 1 1 calc R U . . .
H25B H 0.256200 0.423982 1.073704 0.049 Uiso 1 1 calc R U . . .
H25C H 0.140820 0.416590 0.982187 0.049 Uiso 1 1 calc R U . . .
Br1 Br 1.17181(4) 0.16531(4) 0.37712(4) 0.03629(15) Uani 1 1 d . . . . .
Br2 Br 0.74980(4) 1.12091(3) 0.89340(3) 0.02150(13) Uani 1 1 d . . . . .
N4 N 0.4557(3) 0.6341(2) 0.6882(3) 0.0148(6) Uani 1 1 d . . . . .
N8 N 0.3997(3) 0.4693(3) 0.8707(3) 0.0204(7) Uani 1 1 d . . . . .
O3 O 0.5301(2) 0.7584(2) 0.4959(2) 0.0215(6) Uani 1 1 d . . . . .
O22 O 0.0665(3) 0.7260(2) 0.9492(3) 0.0341(7) Uani 1 1 d . . . . .
O23 O 0.1685(2) 0.8757(2) 0.7911(2) 0.0253(6) Uani 1 1 d . . . . .
S1 S 0.60140(9) 0.42374(8) 0.70948(8) 0.0200(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C9 1.341(5) . ?
C2 C3 1.481(5) . ?
C2 S1 1.764(3) . ?
C3 O3 1.210(4) . ?
C3 N4 1.385(4) . ?
C5 N4 1.474(4) . ?
C5 C6 1.522(5) . ?
C5 C16 1.526(4) . ?
C5 H5 1.0000 . ?
C6 C7 1.344(5) . ?
C6 C22 1.494(5) . ?
C7 N8 1.415(5) . ?
C7 C25 1.502(5) . ?
C8A N8 1.281(4) . ?
C8A N4 1.368(4) . ?
C8A S1 1.751(4) . ?
C9 C10 1.451(5) . ?
C9 H9 0.9500 . ?
C10 C15 1.394(5) . ?
C10 C11 1.403(5) . ?
C11 C12 1.379(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(6) . ?
C13 Br1 1.898(4) . ?
C14 C15 1.395(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.375(5) . ?
C16 C17 1.385(5) . ?
C17 C18 1.387(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(5) . ?
C19 Br2 1.905(3) . ?
C20 C21 1.391(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O22 1.217(4) . ?
C22 O23 1.332(4) . ?
C23 O23 1.457(4) . ?
C23 C24 1.503(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C9 C2 C3 121.6(3) . . ?
C9 C2 S1 128.1(3) . . ?
C3 C2 S1 110.2(2) . . ?
O3 C3 N4 123.6(3) . . ?
O3 C3 C2 126.5(3) . . ?
N4 C3 C2 109.9(3) . . ?
N4 C5 C6 108.0(3) . . ?
N4 C5 C16 109.8(3) . . ?
C6 C5 C16 112.8(3) . . ?
N4 C5 H5 108.7 . . ?
C6 C5 H5 108.7 . . ?
C16 C5 H5 108.7 . . ?
C7 C6 C22 123.7(3) . . ?
C7 C6 C5 121.7(3) . . ?
C22 C6 C5 114.5(3) . . ?
C6 C7 N8 122.3(3) . . ?
C6 C7 C25 126.3(3) . . ?
N8 C7 C25 111.4(3) . . ?
N8 C8A N4 126.6(3) . . ?
N8 C8A S1 122.0(3) . . ?
N4 C8A S1 111.4(2) . . ?
C2 C9 C10 130.7(3) . . ?
C2 C9 H9 114.6 . . ?
C10 C9 H9 114.6 . . ?
C15 C10 C11 117.9(3) . . ?
C15 C10 C9 118.3(3) . . ?
C11 C10 C9 123.8(3) . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.4(4) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 121.5(4) . . ?
C14 C13 Br1 118.9(3) . . ?
C12 C13 Br1 119.7(3) . . ?
C13 C14 C15 118.7(4) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C10 C15 C14 121.4(4) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C21 C16 C17 119.8(3) . . ?
C21 C16 C5 120.4(3) . . ?
C17 C16 C5 119.8(3) . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 118.7(4) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C18 C19 C20 121.6(3) . . ?
C18 C19 Br2 119.6(3) . . ?
C20 C19 Br2 118.8(2) . . ?
C19 C20 C21 119.0(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C16 C21 C20 120.3(4) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
O22 C22 O23 123.8(3) . . ?
O22 C22 C6 125.8(4) . . ?
O23 C22 C6 110.4(3) . . ?
O23 C23 C24 106.7(3) . . ?
O23 C23 H23A 110.4 . . ?
C24 C23 H23A 110.4 . . ?
O23 C23 H23B 110.4 . . ?
C24 C23 H23B 110.4 . . ?
H23A C23 H23B 108.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 C25 H25A 109.5 . . ?
C7 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C7 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C8A N4 C3 116.9(3) . . ?
C8A N4 C5 120.2(3) . . ?
C3 N4 C5 122.2(3) . . ?
C8A N8 C7 116.2(3) . . ?
C22 O23 C23 116.9(3) . . ?
C8A S1 C2 91.42(16) . . ?

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
C9 C2 C3 O3 1.4(6) . . . . ?
S1 C2 C3 O3 179.2(3) . . . . ?
C9 C2 C3 N4 -177.8(3) . . . . ?
S1 C2 C3 N4 0.0(3) . . . . ?
N4 C5 C6 C7 19.6(5) . . . . ?
C16 C5 C6 C7 -101.9(4) . . . . ?
N4 C5 C6 C22 -164.2(3) . . . . ?
C16 C5 C6 C22 74.3(4) . . . . ?
C22 C6 C7 N8 -179.3(3) . . . . ?
C5 C6 C7 N8 -3.4(6) . . . . ?
C22 C6 C7 C25 0.3(6) . . . . ?
C5 C6 C7 C25 176.2(3) . . . . ?
C3 C2 C9 C10 177.7(3) . . . . ?
S1 C2 C9 C10 0.4(6) . . . . ?
C2 C9 C10 C15 -166.7(4) . . . . ?
C2 C9 C10 C11 11.9(6) . . . . ?
C15 C10 C11 C12 1.0(6) . . . . ?
C9 C10 C11 C12 -177.7(3) . . . . ?
C10 C11 C12 C13 0.8(6) . . . . ?
C11 C12 C13 C14 -2.2(6) . . . . ?
C11 C12 C13 Br1 177.6(3) . . . . ?
C12 C13 C14 C15 1.8(6) . . . . ?
Br1 C13 C14 C15 -178.1(3) . . . . ?
C11 C10 C15 C14 -1.4(6) . . . . ?
C9 C10 C15 C14 177.3(3) . . . . ?
C13 C14 C15 C10 0.1(6) . . . . ?
N4 C5 C16 C21 108.1(4) . . . . ?
C6 C5 C16 C21 -131.5(3) . . . . ?
N4 C5 C16 C17 -70.9(4) . . . . ?
C6 C5 C16 C17 49.6(4) . . . . ?
C21 C16 C17 C18 -0.7(5) . . . . ?
C5 C16 C17 C18 178.3(3) . . . . ?
C16 C17 C18 C19 0.5(5) . . . . ?
C17 C18 C19 C20 0.2(5) . . . . ?
C17 C18 C19 Br2 -179.7(2) . . . . ?
C18 C19 C20 C21 -0.7(5) . . . . ?
Br2 C19 C20 C21 179.2(2) . . . . ?
C17 C16 C21 C20 0.1(5) . . . . ?
C5 C16 C21 C20 -178.9(3) . . . . ?
C19 C20 C21 C16 0.6(5) . . . . ?
C7 C6 C22 O22 -1.5(6) . . . . ?
C5 C6 C22 O22 -177.6(3) . . . . ?
C7 C6 C22 O23 176.9(3) . . . . ?
C5 C6 C22 O23 0.8(4) . . . . ?
N8 C8A N4 C3 -173.9(3) . . . . ?
S1 C8A N4 C3 4.1(4) . . . . ?
N8 C8A N4 C5 15.3(5) . . . . ?
S1 C8A N4 C5 -166.6(2) . . . . ?
O3 C3 N4 C8A 178.1(3) . . . . ?
C2 C3 N4 C8A -2.6(4) . . . . ?
O3 C3 N4 C5 -11.3(5) . . . . ?
C2 C3 N4 C5 167.9(3) . . . . ?
C6 C5 N4 C8A -25.0(4) . . . . ?
C16 C5 N4 C8A 98.4(3) . . . . ?
C6 C5 N4 C3 164.8(3) . . . . ?
C16 C5 N4 C3 -71.9(4) . . . . ?
N4 C8A N8 C7 3.9(5) . . . . ?
S1 C8A N8 C7 -174.0(2) . . . . ?
C6 C7 N8 C8A -9.8(5) . . . . ?
C25 C7 N8 C8A 170.6(3) . . . . ?
O22 C22 O23 C23 4.4(5) . . . . ?
C6 C22 O23 C23 -174.0(3) . . . . ?
C24 C23 O23 C22 152.5(3) . . . . ?
N8 C8A S1 C2 174.8(3) . . . . ?
N4 C8A S1 C2 -3.3(3) . . . . ?
C9 C2 S1 C8A 179.5(3) . . . . ?
C3 C2 S1 C8A 1.9(3) . . . . ?

_refine_diff_density_max         0.723
_refine_diff_density_min         -1.032
_refine_diff_density_rms         0.085

# start Validation Reply Form
_vrf_THETM01_shelx               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: poor crystal quality
;
# end Validation Reply Form

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2451730'
loop_
_audit_author_name
_audit_author_address
'Igor Litvinov'
;Arbuzov Institute of Organic and Physical Chemistry RAS
Russia
;
_audit_update_record             
;
2025-05-16 deposited with the CCDC.	2025-09-16 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 Br Cl N2 O3 S'
_chemical_formula_sum            'C23 H18 Br Cl N2 O3 S'
_chemical_formula_weight         517.81

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8663(8)
_cell_length_b                   10.3740(9)
_cell_length_c                   10.8917(9)
_cell_angle_alpha                78.015(3)
_cell_angle_beta                 85.853(3)
_cell_angle_gamma                88.601(3)
_cell_volume                     1087.59(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9664
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      31.04

_exptl_crystal_description       prismatic
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.137
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.5410

_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS DIAMOND'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59222
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.916
_diffrn_reflns_theta_max         31.126
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6974
_reflns_number_gt                5936
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0292P)²+1.2397P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6974
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0871
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.37287(17) 0.45394(16) 0.42625(15) 0.0147(3) Uani 1 1 d . . . . .
C3 C 0.46628(16) 0.34024(16) 0.42051(15) 0.0143(3) Uani 1 1 d . . . . .
C5 C 0.62838(16) 0.26017(16) 0.26433(15) 0.0140(3) Uani 1 1 d . . . . .
H5 H 0.680067 0.211648 0.335694 0.017 Uiso 1 1 calc R U . . .
C6 C 0.72906(17) 0.32606(17) 0.15960(15) 0.0167(3) Uani 1 1 d . . . . .
C7 C 0.70894(18) 0.45045(18) 0.09601(16) 0.0189(3) Uani 1 1 d . . . . .
C8A C 0.52775(17) 0.48403(16) 0.22971(15) 0.0154(3) Uani 1 1 d . . . . .
C9 C 0.28287(17) 0.45105(17) 0.52554(16) 0.0174(3) Uani 1 1 d . . . . .
H9 H 0.286524 0.374113 0.590149 0.021 Uiso 1 1 calc R U . . .
C10 C 0.18054(17) 0.54850(18) 0.54870(17) 0.0187(3) Uani 1 1 d . . . . .
C11 C 0.08117(19) 0.5112(2) 0.64682(17) 0.0240(4) Uani 1 1 d . . . . .
H11 H 0.084916 0.425427 0.698425 0.029 Uiso 1 1 calc R U . . .
C12 C -0.0229(2) 0.5969(2) 0.67042(19) 0.0275(4) Uani 1 1 d . . . . .
H12 H -0.091035 0.569542 0.736353 0.033 Uiso 1 1 calc R U . . .
C13 C -0.02646(18) 0.7221(2) 0.59721(19) 0.0240(4) Uani 1 1 d . . . . .
C14 C 0.0724(2) 0.7647(2) 0.5016(2) 0.0269(4) Uani 1 1 d . . . . .
H14 H 0.070074 0.852091 0.453122 0.032 Uiso 1 1 calc R U . . .
C15 C 0.17515(19) 0.67721(19) 0.4777(2) 0.0243(4) Uani 1 1 d . . . . .
H15 H 0.243078 0.705420 0.411803 0.029 Uiso 1 1 calc R U . . .
C16 C 0.53652(16) 0.16363(16) 0.22385(15) 0.0139(3) Uani 1 1 d . . . . .
C17 C 0.51583(18) 0.03908(16) 0.29835(16) 0.0172(3) Uani 1 1 d . . . . .
H17 H 0.560527 0.013750 0.374172 0.021 Uiso 1 1 calc R U . . .
C18 C 0.43015(18) -0.04883(17) 0.26276(16) 0.0186(3) Uani 1 1 d . . . . .
H18 H 0.416469 -0.134449 0.313327 0.022 Uiso 1 1 calc R U . . .
C19 C 0.36515(17) -0.00996(17) 0.15281(16) 0.0164(3) Uani 1 1 d . . . . .
C20 C 0.38416(18) 0.11343(17) 0.07697(16) 0.0184(3) Uani 1 1 d . . . . .
H20 H 0.338698 0.138606 0.001557 0.022 Uiso 1 1 calc R U . . .
C21 C 0.47098(17) 0.19997(17) 0.11302(15) 0.0172(3) Uani 1 1 d . . . . .
H21 H 0.485721 0.284906 0.061381 0.021 Uiso 1 1 calc R U . . .
C22 C 0.84391(18) 0.24092(19) 0.12786(17) 0.0203(3) Uani 1 1 d . . . . .
C23 C 0.9293(2) 0.0211(2) 0.1734(2) 0.0289(4) Uani 1 1 d . . . . .
H23A H 1.016033 0.030059 0.211155 0.035 Uiso 1 1 calc R U . . .
H23B H 0.947722 0.031586 0.081326 0.035 Uiso 1 1 calc R U . . .
C24 C 0.8687(3) -0.1105(2) 0.2279(3) 0.0401(5) Uani 1 1 d . . . . .
H24A H 0.850774 -0.119650 0.318915 0.060 Uiso 1 1 calc R U . . .
H24B H 0.932273 -0.179895 0.211054 0.060 Uiso 1 1 calc R U . . .
H24C H 0.783403 -0.118479 0.189366 0.060 Uiso 1 1 calc R U . . .
C25 C 0.7971(2) 0.5229(2) -0.01225(19) 0.0294(4) Uani 1 1 d . . . . .
H25A H 0.850378 0.588523 0.015869 0.044 Uiso 1 1 calc R U . . .
H25B H 0.740106 0.567384 -0.078732 0.044 Uiso 1 1 calc R U . . .
H25C H 0.858635 0.460536 -0.044976 0.044 Uiso 1 1 calc R U . . .
Br1 Br -0.17137(2) 0.83793(2) 0.62633(2) 0.03320(7) Uani 1 1 d . . . . .
Cl19 Cl 0.25606(4) -0.11987(4) 0.10965(4) 0.02186(9) Uani 1 1 d . . . . .
N4 N 0.54511(14) 0.36394(13) 0.30816(13) 0.0140(2) Uani 1 1 d . . . . .
N8 N 0.59810(16) 0.52930(15) 0.12781(14) 0.0192(3) Uani 1 1 d . . . . .
O3 O 0.47432(13) 0.24036(12) 0.50004(11) 0.0187(2) Uani 1 1 d . . . . .
O22 O 0.93482(15) 0.27066(15) 0.04750(16) 0.0323(3) Uani 1 1 d . . . . .
O23 O 0.83233(14) 0.12034(14) 0.20106(13) 0.0238(3) Uani 1 1 d . . . . .
S1 S 0.39690(4) 0.57587(4) 0.28921(4) 0.01776(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C9 1.344(2) . ?
C2 C3 1.488(2) . ?
C2 S1 1.7503(17) . ?
C3 O3 1.210(2) . ?
C3 N4 1.382(2) . ?
C5 N4 1.475(2) . ?
C5 C6 1.517(2) . ?
C5 C16 1.518(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.349(3) . ?
C6 C22 1.485(2) . ?
C7 N8 1.416(2) . ?
C7 C25 1.492(2) . ?
C8A N8 1.274(2) . ?
C8A N4 1.371(2) . ?
C8A S1 1.7521(17) . ?
C9 C10 1.457(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(2) . ?
C10 C15 1.399(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.376(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 Br1 1.8968(18) . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.387(2) . ?
C16 C21 1.389(2) . ?
C17 C18 1.389(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(2) . ?
C19 Cl19 1.7423(17) . ?
C20 C21 1.388(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O22 1.206(2) . ?
C22 O23 1.339(2) . ?
C23 O23 1.451(2) . ?
C23 C24 1.492(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C9 C2 C3 120.46(15) . . ?
C9 C2 S1 129.05(14) . . ?
C3 C2 S1 110.45(11) . . ?
O3 C3 N4 123.52(15) . . ?
O3 C3 C2 126.64(15) . . ?
N4 C3 C2 109.85(13) . . ?
N4 C5 C6 108.17(13) . . ?
N4 C5 C16 109.59(13) . . ?
C6 C5 C16 113.11(13) . . ?
N4 C5 H5 108.6 . . ?
C6 C5 H5 108.6 . . ?
C16 C5 H5 108.6 . . ?
C7 C6 C22 123.39(16) . . ?
C7 C6 C5 121.38(15) . . ?
C22 C6 C5 115.11(15) . . ?
C6 C7 N8 122.25(15) . . ?
C6 C7 C25 126.14(17) . . ?
N8 C7 C25 111.61(16) . . ?
N8 C8A N4 126.31(16) . . ?
N8 C8A S1 122.13(13) . . ?
N4 C8A S1 111.52(12) . . ?
C2 C9 C10 129.56(16) . . ?
C2 C9 H9 115.2 . . ?
C10 C9 H9 115.2 . . ?
C11 C10 C15 117.89(17) . . ?
C11 C10 C9 118.21(17) . . ?
C15 C10 C9 123.90(16) . . ?
C12 C11 C10 121.27(19) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 119.24(18) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 121.46(18) . . ?
C12 C13 Br1 119.34(14) . . ?
C14 C13 Br1 119.19(16) . . ?
C13 C14 C15 118.73(19) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C10 121.36(18) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C17 C16 C21 119.50(15) . . ?
C17 C16 C5 120.17(14) . . ?
C21 C16 C5 120.32(15) . . ?
C16 C17 C18 120.39(15) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.02(16) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 121.70(16) . . ?
C18 C19 Cl19 118.83(13) . . ?
C20 C19 Cl19 119.47(13) . . ?
C19 C20 C21 118.72(15) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C20 C21 C16 120.66(16) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
O22 C22 O23 122.91(17) . . ?
O22 C22 C6 127.10(18) . . ?
O23 C22 C6 109.98(15) . . ?
O23 C23 C24 107.50(18) . . ?
O23 C23 H23A 110.2 . . ?
C24 C23 H23A 110.2 . . ?
O23 C23 H23B 110.2 . . ?
C24 C23 H23B 110.2 . . ?
H23A C23 H23B 108.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 C25 H25A 109.5 . . ?
C7 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C7 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C8A N4 C3 116.59(14) . . ?
C8A N4 C5 120.35(13) . . ?
C3 N4 C5 122.42(13) . . ?
C8A N8 C7 116.61(15) . . ?
C22 O23 C23 116.85(15) . . ?
C2 S1 C8A 91.45(8) . . ?

_refine_diff_density_max         2.449
_refine_diff_density_min         -1.394
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2451728'
loop_
_audit_author_name
_audit_author_address
'Igor Litvinov'
;Arbuzov Institute of Organic and Physical Chemistry RAS
Russia
;
_audit_update_record             
;
2025-05-16 deposited with the CCDC.	2025-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 Br2 N2 O3 S'
_chemical_formula_sum            'C23 H18 Br2 N2 O3 S'
_chemical_formula_weight         562.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7322(10)
_cell_length_b                   11.5483(14)
_cell_length_c                   12.9685(16)
_cell_angle_alpha                74.852(4)
_cell_angle_beta                 85.203(4)
_cell_angle_gamma                73.512(4)
_cell_volume                     1071.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      28.24

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    3.908
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.5162

_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS DIAMOND'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            65380
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.899
_diffrn_reflns_theta_max         28.283
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5295
_reflns_number_gt                4463
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0390P)²+0.7712P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5295
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0729
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.5238(3) 0.59072(19) 0.75720(17) 0.0149(4) Uani 1 1 d . . . . .
C3 C 0.6302(3) 0.65542(19) 0.80038(16) 0.0141(4) Uani 1 1 d . . . . .
C5 C 0.8451(3) 0.78555(18) 0.73646(16) 0.0116(4) Uani 1 1 d . . . . .
H5 H 0.904330 0.752924 0.807882 0.014 Uiso 1 1 calc R U . . .
C6 C 0.9894(3) 0.79128(19) 0.64914(16) 0.0133(4) Uani 1 1 d . . . . .
C7 C 0.9780(3) 0.7572(2) 0.55878(17) 0.0157(4) Uani 1 1 d . . . . .
C8A C 0.7434(3) 0.67376(19) 0.62550(16) 0.0137(4) Uani 1 1 d . . . . .
C9 C 0.3972(3) 0.5449(2) 0.81866(17) 0.0160(4) Uani 1 1 d . . . . .
H9 H 0.392630 0.551146 0.890506 0.019 Uiso 1 1 calc R U . . .
C10 C 0.2662(3) 0.48753(19) 0.79341(17) 0.0156(4) Uani 1 1 d . . . . .
C11 C 0.1658(3) 0.43580(19) 0.87901(17) 0.0164(4) Uani 1 1 d . . . . .
H11 H 0.185471 0.437987 0.949725 0.020 Uiso 1 1 calc R U . . .
C12 C 0.0380(3) 0.38170(19) 0.85966(18) 0.0171(4) Uani 1 1 d . . . . .
C13 C 0.0034(3) 0.3778(2) 0.75801(18) 0.0178(4) Uani 1 1 d . . . . .
H13 H -0.086014 0.340814 0.746427 0.021 Uiso 1 1 calc R U . . .
C14 C 0.1029(3) 0.4295(2) 0.67286(18) 0.0185(4) Uani 1 1 d . . . . .
H14 H 0.081684 0.427478 0.602333 0.022 Uiso 1 1 calc R U . . .
C15 C 0.2325(3) 0.4838(2) 0.69030(17) 0.0161(4) Uani 1 1 d . . . . .
H15 H 0.299109 0.518998 0.631538 0.019 Uiso 1 1 calc R U . . .
C16 C 0.7170(3) 0.91535(19) 0.72992(16) 0.0127(4) Uani 1 1 d . . . . .
C17 C 0.6879(3) 0.96424(19) 0.81914(17) 0.0140(4) Uani 1 1 d . . . . .
H17 H 0.742166 0.916300 0.885493 0.017 Uiso 1 1 calc R U . . .
C18 C 0.5776(3) 1.0849(2) 0.80905(18) 0.0166(4) Uani 1 1 d . . . . .
C19 C 0.4951(3) 1.1550(2) 0.71422(19) 0.0193(5) Uani 1 1 d . . . . .
H19 H 0.419701 1.237106 0.708995 0.023 Uiso 1 1 calc R U . . .
C20 C 0.5233(3) 1.1045(2) 0.62657(18) 0.0194(5) Uani 1 1 d . . . . .
H20 H 0.465659 1.151827 0.561008 0.023 Uiso 1 1 calc R U . . .
C21 C 0.6352(3) 0.9853(2) 0.63370(17) 0.0163(4) Uani 1 1 d . . . . .
H21 H 0.655765 0.951609 0.572898 0.020 Uiso 1 1 calc R U . . .
C22 C 1.1322(3) 0.8463(2) 0.66742(17) 0.0160(4) Uani 1 1 d . . . . .
C23 C 1.2248(3) 0.9374(3) 0.7912(2) 0.0322(6) Uani 1 1 d . . . . .
H23A H 1.276525 0.982478 0.725902 0.039 Uiso 1 1 calc R U . . .
H23B H 1.325192 0.876439 0.835471 0.039 Uiso 1 1 calc R U . . .
C24 C 1.1165(3) 1.0274(2) 0.8525(2) 0.0232(5) Uani 1 1 d . . . . .
H24A H 1.015929 1.086146 0.808744 0.035 Uiso 1 1 calc R U . . .
H24B H 1.193486 1.073431 0.870727 0.035 Uiso 1 1 calc R U . . .
H24C H 1.069299 0.981700 0.918212 0.035 Uiso 1 1 calc R U . . .
C25 C 1.1011(3) 0.7700(2) 0.46295(18) 0.0252(5) Uani 1 1 d . . . . .
H25A H 1.191622 0.809589 0.474898 0.038 Uiso 1 1 calc R U . . .
H25B H 1.030314 0.821459 0.399734 0.038 Uiso 1 1 calc R U . . .
H25C H 1.161482 0.687258 0.451714 0.038 Uiso 1 1 calc R U . . .
Br1 Br -0.09138(3) 0.30743(2) 0.97706(2) 0.02319(7) Uani 1 1 d . . . . .
Br02 Br 0.53988(3) 1.15657(2) 0.92791(2) 0.02430(7) Uani 1 1 d . . . . .
N4 N 0.7453(2) 0.69999(16) 0.72230(13) 0.0127(3) Uani 1 1 d . . . . .
N8 N 0.8438(2) 0.70151(17) 0.54411(14) 0.0157(4) Uani 1 1 d . . . . .
O3 O 0.6193(2) 0.67078(15) 0.89016(12) 0.0187(3) Uani 1 1 d . . . . .
O22 O 1.2556(2) 0.86504(19) 0.60843(14) 0.0291(4) Uani 1 1 d . . . . .
O23 O 1.1070(2) 0.87346(17) 0.76288(13) 0.0233(4) Uani 1 1 d . . . . .
S1 S 0.58597(7) 0.59113(5) 0.62358(4) 0.01587(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C9 1.347(3) . ?
C2 C3 1.481(3) . ?
C2 S1 1.758(2) . ?
C3 O3 1.215(3) . ?
C3 N4 1.385(3) . ?
C5 N4 1.469(3) . ?
C5 C6 1.524(3) . ?
C5 C16 1.530(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.347(3) . ?
C6 C22 1.483(3) . ?
C7 N8 1.416(3) . ?
C7 C25 1.502(3) . ?
C8A N8 1.284(3) . ?
C8A N4 1.368(3) . ?
C8A S1 1.752(2) . ?
C9 C10 1.457(3) . ?
C9 H9 0.9500 . ?
C10 C15 1.397(3) . ?
C10 C11 1.402(3) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(3) . ?
C12 Br1 1.899(2) . ?
C13 C14 1.393(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.387(3) . ?
C16 C17 1.391(3) . ?
C17 C18 1.392(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(3) . ?
C18 Br02 1.897(2) . ?
C19 C20 1.383(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O22 1.205(3) . ?
C22 O23 1.340(3) . ?
C23 O23 1.446(3) . ?
C23 C24 1.497(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C9 C2 C3 119.99(19) . . ?
C9 C2 S1 129.70(18) . . ?
C3 C2 S1 110.28(15) . . ?
O3 C3 N4 123.4(2) . . ?
O3 C3 C2 126.38(19) . . ?
N4 C3 C2 110.19(18) . . ?
N4 C5 C6 108.24(16) . . ?
N4 C5 C16 110.34(16) . . ?
C6 C5 C16 110.41(16) . . ?
N4 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C16 C5 H5 109.3 . . ?
C7 C6 C22 123.18(19) . . ?
C7 C6 C5 121.47(19) . . ?
C22 C6 C5 115.16(17) . . ?
C6 C7 N8 122.32(19) . . ?
C6 C7 C25 126.5(2) . . ?
N8 C7 C25 111.18(19) . . ?
N8 C8A N4 126.6(2) . . ?
N8 C8A S1 121.61(17) . . ?
N4 C8A S1 111.80(15) . . ?
C2 C9 C10 130.8(2) . . ?
C2 C9 H9 114.6 . . ?
C10 C9 H9 114.6 . . ?
C15 C10 C11 118.8(2) . . ?
C15 C10 C9 124.3(2) . . ?
C11 C10 C9 116.88(19) . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 122.2(2) . . ?
C11 C12 Br1 118.83(17) . . ?
C13 C12 Br1 118.96(16) . . ?
C12 C13 C14 118.4(2) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 120.7(2) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C21 C16 C17 120.4(2) . . ?
C21 C16 C5 119.60(19) . . ?
C17 C16 C5 119.98(18) . . ?
C18 C17 C16 118.5(2) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C19 C18 C17 121.6(2) . . ?
C19 C18 Br02 118.60(16) . . ?
C17 C18 Br02 119.77(17) . . ?
C18 C19 C20 119.2(2) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C19 C20 C21 120.5(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 119.8(2) . . ?
C20 C21 H21 120.1 . . ?
C16 C21 H21 120.1 . . ?
O22 C22 O23 122.8(2) . . ?
O22 C22 C6 127.4(2) . . ?
O23 C22 C6 109.87(17) . . ?
O23 C23 C24 108.27(19) . . ?
O23 C23 H23A 110.0 . . ?
C24 C23 H23A 110.0 . . ?
O23 C23 H23B 110.0 . . ?
C24 C23 H23B 110.0 . . ?
H23A C23 H23B 108.4 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 C25 H25A 109.5 . . ?
C7 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C7 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C8A N4 C3 116.38(18) . . ?
C8A N4 C5 120.90(17) . . ?
C3 N4 C5 122.17(17) . . ?
C8A N8 C7 116.36(18) . . ?
C22 O23 C23 117.87(17) . . ?
C8A S1 C2 91.32(10) . . ?

_refine_diff_density_max         0.737
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.110

####################################################################### 
# 
# 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_shelx_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2451731'
loop_
_audit_author_name
_audit_author_address
'Igor Litvinov'
;Arbuzov Institute of Organic and Physical Chemistry RAS
Russia
;
_audit_update_record             
;
2025-05-16 deposited with the CCDC.	2025-09-16 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 Br Cl N2 O3 S'
_chemical_formula_sum            'C23 H18 Br Cl N2 O3 S'
_chemical_formula_weight         517.81

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6350(4)
_cell_length_b                   10.8780(6)
_cell_length_c                   13.2457(8)
_cell_angle_alpha                105.712(2)
_cell_angle_beta                 94.019(2)
_cell_angle_gamma                90.956(2)
_cell_volume                     1055.66(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9828
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      40.11

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    2.202
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.5954

_exptl_absorpt_correction_T_max  0.7479
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS DIAMOND'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50954
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.676
_diffrn_reflns_theta_max         32.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             7931
_reflns_number_gt                7007
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²+0.4460P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7931
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.20346(15) 0.55487(11) 0.35421(9) 0.01223(19) Uani 1 1 d . . . . .
C3 C 0.14802(15) 0.67705(11) 0.42478(9) 0.01209(19) Uani 1 1 d . . . . .
C5 C 0.13991(16) 0.78406(11) 0.61661(9) 0.01145(19) Uani 1 1 d . . . . .
H5 H 0.024749 0.822464 0.604885 0.014 Uiso 1 1 calc R U . . .
C6 C 0.14101(16) 0.74215(11) 0.71782(9) 0.01251(19) Uani 1 1 d . . . . .
C7 C 0.18987(16) 0.62456(12) 0.72231(9) 0.0131(2) Uani 1 1 d . . . . .
C8A C 0.21669(16) 0.55783(11) 0.54465(9) 0.01238(19) Uani 1 1 d . . . . .
C9 C 0.21259(17) 0.54242(12) 0.25075(10) 0.0144(2) Uani 1 1 d . . . . .
H9 H 0.175109 0.613998 0.227918 0.017 Uiso 1 1 calc R U . . .
C10 C 0.27080(17) 0.43661(12) 0.16851(10) 0.0148(2) Uani 1 1 d . . . . .
C11 C 0.2891(2) 0.45653(14) 0.06932(11) 0.0202(2) Uani 1 1 d . . . . .
H11 H 0.259417 0.536438 0.057930 0.024 Uiso 1 1 calc R U . . .
C12 C 0.3495(2) 0.36203(14) -0.01244(11) 0.0221(3) Uani 1 1 d . . . . .
H12 H 0.361148 0.376971 -0.079111 0.027 Uiso 1 1 calc R U . . .
C13 C 0.39276(18) 0.24552(14) 0.00443(10) 0.0190(2) Uani 1 1 d . . . . .
C14 C 0.3738(2) 0.22165(13) 0.10083(11) 0.0200(2) Uani 1 1 d . . . . .
H14 H 0.402819 0.141235 0.111407 0.024 Uiso 1 1 calc R U . . .
C15 C 0.31182(19) 0.31680(13) 0.18177(10) 0.0182(2) Uani 1 1 d . . . . .
H15 H 0.296985 0.300133 0.247506 0.022 Uiso 1 1 calc R U . . .
C16 C 0.28751(15) 0.88223(11) 0.62337(9) 0.01171(19) Uani 1 1 d . . . . .
C17 C 0.25263(16) 1.00627(11) 0.62015(9) 0.0131(2) Uani 1 1 d . . . . .
H17 H 0.135122 1.031383 0.611748 0.016 Uiso 1 1 calc R U . . .
C18 C 0.39266(17) 1.09272(11) 0.62942(10) 0.0143(2) Uani 1 1 d . . . . .
C19 C 0.56548(17) 1.05771(13) 0.63931(10) 0.0169(2) Uani 1 1 d . . . . .
H19 H 0.659563 1.117803 0.644159 0.020 Uiso 1 1 calc R U . . .
C20 C 0.59889(17) 0.93389(13) 0.64200(11) 0.0193(2) Uani 1 1 d . . . . .
H20 H 0.716636 0.908611 0.648907 0.023 Uiso 1 1 calc R U . . .
C21 C 0.46054(17) 0.84653(12) 0.63463(11) 0.0165(2) Uani 1 1 d . . . . .
H21 H 0.484113 0.761941 0.637283 0.020 Uiso 1 1 calc R U . . .
C22 C 0.09879(17) 0.84075(12) 0.81326(10) 0.0156(2) Uani 1 1 d . . . . .
C23 C -0.0145(2) 1.04605(13) 0.87769(10) 0.0192(2) Uani 1 1 d . . . . .
H23A H 0.082598 1.059390 0.933574 0.023 Uiso 1 1 calc R U . . .
H23B H -0.124239 1.026784 0.906996 0.023 Uiso 1 1 calc R U . . .
C24 C -0.0337(2) 1.16386(14) 0.84014(12) 0.0253(3) Uani 1 1 d . . . . .
H24A H 0.075401 1.182023 0.811148 0.038 Uiso 1 1 calc R U . . .
H24B H -0.057932 1.236362 0.899269 0.038 Uiso 1 1 calc R U . . .
H24C H -0.130956 1.150113 0.785498 0.038 Uiso 1 1 calc R U . . .
C25 C 0.20442(19) 0.57681(13) 0.81864(10) 0.0171(2) Uani 1 1 d . . . . .
H25A H 0.323822 0.594912 0.852566 0.026 Uiso 1 1 calc R U . . .
H25B H 0.178819 0.484421 0.798541 0.026 Uiso 1 1 calc R U . . .
H25C H 0.120137 0.619915 0.867731 0.026 Uiso 1 1 calc R U . . .
Br1 Br 0.34723(2) 1.26424(2) 0.63207(2) 0.01957(4) Uani 1 1 d . . . . .
Cl1 Cl 0.47063(6) 0.12895(4) -0.09725(3) 0.02912(8) Uani 1 1 d . . . . .
N4 N 0.16058(14) 0.67042(9) 0.52831(8) 0.01153(17) Uani 1 1 d . . . . .
N8 N 0.23505(15) 0.53041(10) 0.63276(9) 0.01531(19) Uani 1 1 d . . . . .
O3 O 0.10147(13) 0.77087(9) 0.39932(7) 0.01583(17) Uani 1 1 d . . . . .
O22 O 0.12899(19) 0.83566(11) 0.90262(8) 0.0314(3) Uani 1 1 d . . . . .
O23 O 0.02268(13) 0.94040(9) 0.78831(7) 0.01653(17) Uani 1 1 d . . . . .
S1 S 0.26079(4) 0.44720(3) 0.42694(2) 0.01475(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C9 1.3470(17) . ?
C2 C3 1.4902(16) . ?
C2 S1 1.7495(12) . ?
C3 O3 1.2096(14) . ?
C3 N4 1.3895(15) . ?
C5 N4 1.4732(15) . ?
C5 C16 1.5206(17) . ?
C5 C6 1.5280(16) . ?
C5 H5 1.0000 . ?
C6 C7 1.3538(16) . ?
C6 C22 1.4788(17) . ?
C7 N8 1.4093(16) . ?
C7 C25 1.5004(17) . ?
C8A N8 1.2797(15) . ?
C8A N4 1.3705(15) . ?
C8A S1 1.7503(12) . ?
C9 C10 1.4543(17) . ?
C9 H9 0.9500 . ?
C10 C15 1.3991(18) . ?
C10 C11 1.4041(18) . ?
C11 C12 1.3876(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3868(19) . ?
C13 Cl1 1.7286(13) . ?
C14 C15 1.3896(18) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.3911(16) . ?
C16 C21 1.3925(17) . ?
C17 C18 1.3885(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.3866(18) . ?
C18 Br1 1.8949(12) . ?
C19 C20 1.3846(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.3893(19) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O22 1.2062(16) . ?
C22 O23 1.3453(15) . ?
C23 O23 1.4574(15) . ?
C23 C24 1.5007(19) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C9 C2 C3 120.23(11) . . ?
C9 C2 S1 129.24(10) . . ?
C3 C2 S1 110.42(8) . . ?
O3 C3 N4 123.25(11) . . ?
O3 C3 C2 126.93(11) . . ?
N4 C3 C2 109.81(10) . . ?
N4 C5 C16 110.02(9) . . ?
N4 C5 C6 108.42(9) . . ?
C16 C5 C6 110.97(10) . . ?
N4 C5 H5 109.1 . . ?
C16 C5 H5 109.1 . . ?
C6 C5 H5 109.1 . . ?
C7 C6 C22 121.36(11) . . ?
C7 C6 C5 122.31(11) . . ?
C22 C6 C5 116.17(10) . . ?
C6 C7 N8 122.22(11) . . ?
C6 C7 C25 126.34(11) . . ?
N8 C7 C25 111.44(10) . . ?
N8 C8A N4 126.79(11) . . ?
N8 C8A S1 121.39(9) . . ?
N4 C8A S1 111.81(8) . . ?
C2 C9 C10 130.15(11) . . ?
C2 C9 H9 114.9 . . ?
C10 C9 H9 114.9 . . ?
C15 C10 C11 117.74(12) . . ?
C15 C10 C9 124.50(11) . . ?
C11 C10 C9 117.76(11) . . ?
C12 C11 C10 121.43(12) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 119.15(12) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 121.05(12) . . ?
C14 C13 Cl1 120.05(11) . . ?
C12 C13 Cl1 118.91(10) . . ?
C13 C14 C15 119.19(13) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C10 121.40(12) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C17 C16 C21 119.91(11) . . ?
C17 C16 C5 121.36(10) . . ?
C21 C16 C5 118.72(10) . . ?
C18 C17 C16 118.80(11) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C19 C18 C17 121.74(11) . . ?
C19 C18 Br1 118.89(10) . . ?
C17 C18 Br1 119.35(9) . . ?
C20 C19 C18 119.02(12) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 120.12(12) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 120.39(11) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
O22 C22 O23 123.20(12) . . ?
O22 C22 C6 125.65(12) . . ?
O23 C22 C6 111.14(10) . . ?
O23 C23 C24 108.13(11) . . ?
O23 C23 H23A 110.1 . . ?
C24 C23 H23A 110.1 . . ?
O23 C23 H23B 110.1 . . ?
C24 C23 H23B 110.1 . . ?
H23A C23 H23B 108.4 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 C25 H25A 109.5 . . ?
C7 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C7 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C8A N4 C3 116.35(10) . . ?
C8A N4 C5 121.60(10) . . ?
C3 N4 C5 121.46(9) . . ?
C8A N8 C7 116.86(10) . . ?
C22 O23 C23 115.14(10) . . ?
C2 S1 C8A 91.60(6) . . ?

_refine_diff_density_max         0.988
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.101

####################################################################### 
# 
# 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_shelx_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 2451726'
loop_
_audit_author_name
_audit_author_address
'Igor Litvinov'
;Arbuzov Institute of Organic and Physical Chemistry RAS
Russia
;
_audit_update_record             
;
2025-05-16 deposited with the CCDC.	2025-09-16 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 Br I N2 O3 S'
_chemical_formula_sum            'C23 H18 Br I N2 O3 S'
_chemical_formula_weight         609.26

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1225(8)
_cell_length_b                   10.4444(8)
_cell_length_c                   10.9523(8)
_cell_angle_alpha                76.930(2)
_cell_angle_beta                 85.086(2)
_cell_angle_gamma                88.512(2)
_cell_volume                     1123.75(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9295
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      34.04

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    3.324
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.6084

_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS DIAMOND'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            85068
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.440
_diffrn_reflns_theta_max         31.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             7771
_reflns_number_gt                6374
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.5011P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7771
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.61775(19) 0.54524(18) 0.57761(18) 0.0149(3) Uani 1 1 d . . . . .
C3 C 0.52556(19) 0.65764(18) 0.58180(17) 0.0140(3) Uani 1 1 d . . . . .
C5 C 0.36462(18) 0.73556(18) 0.73669(17) 0.0141(3) Uani 1 1 d . . . . .
H5 H 0.314566 0.784756 0.665599 0.017 Uiso 1 1 calc R U . . .
C6 C 0.26636(19) 0.6693(2) 0.84315(18) 0.0168(3) Uani 1 1 d . . . . .
C7 C 0.2845(2) 0.5454(2) 0.90699(19) 0.0198(4) Uani 1 1 d . . . . .
C8A C 0.46173(19) 0.51207(19) 0.77286(18) 0.0155(3) Uani 1 1 d . . . . .
C9 C 0.70853(19) 0.55047(19) 0.47998(19) 0.0167(3) Uani 1 1 d . . . . .
H9 H 0.705841 0.627974 0.415140 0.020 Uiso 1 1 calc R U . . .
C10 C 0.81051(19) 0.4555(2) 0.45824(19) 0.0176(4) Uani 1 1 d . . . . .
C11 C 0.9074(2) 0.4944(2) 0.3582(2) 0.0239(4) Uani 1 1 d . . . . .
H11 H 0.902610 0.579845 0.305378 0.029 Uiso 1 1 calc R U . . .
C12 C 1.0101(2) 0.4107(3) 0.3350(2) 0.0277(5) Uani 1 1 d . . . . .
H12 H 1.075566 0.438787 0.267262 0.033 Uiso 1 1 calc R U . . .
C13 C 1.0166(2) 0.2859(2) 0.4110(2) 0.0218(4) Uani 1 1 d . . . . .
C14 C 0.9211(2) 0.2435(2) 0.5092(2) 0.0254(4) Uani 1 1 d . . . . .
H14 H 0.925396 0.157055 0.560065 0.031 Uiso 1 1 calc R U . . .
C15 C 0.8192(2) 0.3280(2) 0.5328(2) 0.0242(4) Uani 1 1 d . . . . .
H15 H 0.754128 0.298987 0.600670 0.029 Uiso 1 1 calc R U . . .
C16 C 0.45501(18) 0.83016(18) 0.77529(17) 0.0131(3) Uani 1 1 d . . . . .
C17 C 0.5191(2) 0.79157(19) 0.88522(18) 0.0164(3) Uani 1 1 d . . . . .
H17 H 0.503782 0.706313 0.937046 0.020 Uiso 1 1 calc R U . . .
C18 C 0.6048(2) 0.8755(2) 0.92035(18) 0.0170(3) Uani 1 1 d . . . . .
H18 H 0.649241 0.848175 0.994988 0.020 Uiso 1 1 calc R U . . .
C19 C 0.62458(18) 1.00042(19) 0.84420(18) 0.0152(3) Uani 1 1 d . . . . .
C20 C 0.5613(2) 1.04150(19) 0.73553(19) 0.0183(4) Uani 1 1 d . . . . .
H20 H 0.575544 1.127480 0.684878 0.022 Uiso 1 1 calc R U . . .
C21 C 0.4764(2) 0.95589(19) 0.70063(18) 0.0170(3) Uani 1 1 d . . . . .
H21 H 0.432858 0.983337 0.625512 0.020 Uiso 1 1 calc R U . . .
C22 C 0.1563(2) 0.7547(2) 0.8767(2) 0.0208(4) Uani 1 1 d . . . . .
C23 C 0.0727(2) 0.9738(2) 0.8291(2) 0.0281(5) Uani 1 1 d . . . . .
H23A H 0.049647 0.957388 0.920930 0.034 Uiso 1 1 calc R U . . .
H23B H -0.009697 0.971126 0.787062 0.034 Uiso 1 1 calc R U . . .
C24 C 0.1380(3) 1.1052(3) 0.7825(3) 0.0383(6) Uani 1 1 d . . . . .
H24A H 0.218397 1.107194 0.825896 0.058 Uiso 1 1 calc R U . . .
H24B H 0.076719 1.174457 0.799434 0.058 Uiso 1 1 calc R U . . .
H24C H 0.161518 1.119676 0.691762 0.058 Uiso 1 1 calc R U . . .
C25 C 0.1988(2) 0.4714(3) 1.0177(2) 0.0300(5) Uani 1 1 d . . . . .
H25A H 0.135044 0.532110 1.047435 0.045 Uiso 1 1 calc R U . . .
H25B H 0.254383 0.431363 1.085325 0.045 Uiso 1 1 calc R U . . .
H25C H 0.150829 0.402493 0.992493 0.045 Uiso 1 1 calc R U . . .
Br1 Br 0.74358(2) 1.11574(2) 0.88898(2) 0.01881(5) Uani 1 1 d . . . . .
I1 I 1.17405(2) 0.16067(2) 0.37793(2) 0.02890(5) Uani 1 1 d . . . . .
N4 N 0.44549(16) 0.63213(16) 0.69378(15) 0.0139(3) Uani 1 1 d . . . . .
N8 N 0.39198(18) 0.46582(17) 0.87567(17) 0.0199(3) Uani 1 1 d . . . . .
O3 O 0.51891(15) 0.75809(14) 0.50183(13) 0.0187(3) Uani 1 1 d . . . . .
O22 O 0.07041(17) 0.72557(18) 0.96145(19) 0.0336(4) Uani 1 1 d . . . . .
O23 O 0.16597(15) 0.87497(16) 0.80002(15) 0.0232(3) Uani 1 1 d . . . . .
S1 S 0.59039(5) 0.42133(5) 0.71485(5) 0.01769(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C9 1.341(3) . ?
C2 C3 1.487(3) . ?
C2 S1 1.755(2) . ?
C3 O3 1.210(2) . ?
C3 N4 1.387(2) . ?
C5 N4 1.475(2) . ?
C5 C16 1.515(3) . ?
C5 C6 1.517(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.341(3) . ?
C6 C22 1.483(3) . ?
C7 N8 1.417(3) . ?
C7 C25 1.500(3) . ?
C8A N8 1.279(3) . ?
C8A N4 1.368(2) . ?
C8A S1 1.751(2) . ?
C9 C10 1.455(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.401(3) . ?
C10 C15 1.401(3) . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 I1 2.095(2) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.392(3) . ?
C16 C17 1.390(3) . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.377(3) . ?
C19 Br1 1.8937(19) . ?
C20 C21 1.391(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O22 1.207(3) . ?
C22 O23 1.344(3) . ?
C23 O23 1.450(3) . ?
C23 C24 1.501(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C9 C2 C3 120.43(18) . . ?
C9 C2 S1 129.24(15) . . ?
C3 C2 S1 110.29(13) . . ?
O3 C3 N4 123.38(17) . . ?
O3 C3 C2 126.70(17) . . ?
N4 C3 C2 109.93(16) . . ?
N4 C5 C16 109.26(15) . . ?
N4 C5 C6 107.98(15) . . ?
C16 C5 C6 112.89(15) . . ?
N4 C5 H5 108.9 . . ?
C16 C5 H5 108.9 . . ?
C6 C5 H5 108.9 . . ?
C7 C6 C22 123.19(18) . . ?
C7 C6 C5 121.64(17) . . ?
C22 C6 C5 115.00(18) . . ?
C6 C7 N8 122.58(18) . . ?
C6 C7 C25 126.73(19) . . ?
N8 C7 C25 110.69(19) . . ?
N8 C8A N4 126.28(18) . . ?
N8 C8A S1 121.94(15) . . ?
N4 C8A S1 111.76(14) . . ?
C2 C9 C10 129.85(19) . . ?
C2 C9 H9 115.1 . . ?
C10 C9 H9 115.1 . . ?
C11 C10 C15 117.86(19) . . ?
C11 C10 C9 118.20(19) . . ?
C15 C10 C9 123.93(18) . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.70(19) . . ?
C12 C13 I1 119.45(15) . . ?
C14 C13 I1 119.85(17) . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C10 121.1(2) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C21 C16 C17 119.20(18) . . ?
C21 C16 C5 120.60(17) . . ?
C17 C16 C5 120.20(17) . . ?
C18 C17 C16 121.03(18) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 118.65(18) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C20 C19 C18 121.45(18) . . ?
C20 C19 Br1 119.17(15) . . ?
C18 C19 Br1 119.37(14) . . ?
C19 C20 C21 119.36(18) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C16 120.30(18) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
O22 C22 O23 123.0(2) . . ?
O22 C22 C6 126.8(2) . . ?
O23 C22 C6 110.15(17) . . ?
O23 C23 C24 107.4(2) . . ?
O23 C23 H23A 110.2 . . ?
C24 C23 H23A 110.2 . . ?
O23 C23 H23B 110.2 . . ?
C24 C23 H23B 110.2 . . ?
H23A C23 H23B 108.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 C25 H25A 109.5 . . ?
C7 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C7 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C8A N4 C3 116.45(16) . . ?
C8A N4 C5 120.58(15) . . ?
C3 N4 C5 122.10(16) . . ?
C8A N8 C7 116.19(18) . . ?
C22 O23 C23 116.58(18) . . ?
C2 S1 C8A 91.49(9) . . ?

_refine_diff_density_max         2.314
_refine_diff_density_min         -1.093
_refine_diff_density_rms         0.160

