# Supplementary Information (SI) for Chemical Science.
# 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).
# 
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# 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 
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data_cu_240405lmf_l_0m
_database_code_depnum_ccdc_archive 'CCDC 2354174'
loop_
_audit_author_name
_audit_author_address
'Ying He'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-09 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
_audit_creation_date             2024-04-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 N2 O3 S'
_chemical_formula_sum            'C23 H18 N2 O3 S'
_chemical_formula_weight         402.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0055(4)
_cell_length_b                   12.1682(5)
_cell_length_c                   14.8532(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.525(2)
_cell_angle_gamma                90
_cell_volume                     1925.52(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      68.300
_cell_measurement_theta_min      3.074
_shelx_estimated_absorpt_T_max   0.846
_shelx_estimated_absorpt_T_min   0.807
_exptl_absorpt_coefficient_mu    1.726
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1175 before and 0.0522 after correction.
The Ratio of minimum to maximum transmission is 0.8732.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            39204
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.380
_diffrn_reflns_theta_min         4.149
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3286
_reflns_number_total             3528
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3528
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+0.5014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0880
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_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
S1 S 0.05560(3) 0.45904(3) 0.23113(2) 0.04014(12) Uani 1 1 d . . . . .
O1 O -0.06011(9) 0.50926(9) 0.18132(8) 0.0529(3) Uani 1 1 d . . . . .
O2 O 0.05850(10) 0.40274(9) 0.31649(7) 0.0491(3) Uani 1 1 d . . . . .
O3 O 0.68572(11) 0.48401(10) 0.44914(10) 0.0644(3) Uani 1 1 d . . . . .
N1 N 0.29041(10) 0.55274(9) 0.29739(8) 0.0367(3) Uani 1 1 d . . . . .
N2 N 0.33628(10) 0.44756(9) 0.31932(8) 0.0388(3) Uani 1 1 d . . . . .
C1 C 0.10525(12) 0.36716(12) 0.15588(10) 0.0388(3) Uani 1 1 d . . . . .
C2 C 0.11698(13) 0.40471(13) 0.07014(11) 0.0470(3) Uani 1 1 d . . . . .
H2 H 0.102866 0.479099 0.053776 0.056 Uiso 1 1 calc R U . . .
C3 C 0.14971(15) 0.33117(15) 0.00913(11) 0.0538(4) Uani 1 1 d . . . . .
H3 H 0.157292 0.355626 -0.049247 0.065 Uiso 1 1 calc R U . . .
C4 C 0.17132(14) 0.22189(14) 0.03356(11) 0.0523(4) Uani 1 1 d . . . . .
H4 H 0.193375 0.172309 -0.008225 0.063 Uiso 1 1 calc R U . . .
C5 C 0.16055(14) 0.18563(13) 0.11913(11) 0.0484(4) Uani 1 1 d . . . . .
H5 H 0.175727 0.111372 0.135584 0.058 Uiso 1 1 calc R U . . .
C6 C 0.12751(12) 0.25789(12) 0.18104(11) 0.0420(3) Uani 1 1 d . . . . .
H6 H 0.120263 0.233131 0.239419 0.050 Uiso 1 1 calc R U . . .
C7 C 0.16521(12) 0.56609(11) 0.25033(10) 0.0382(3) Uani 1 1 d . . . . .
C8 C 0.14067(12) 0.67372(11) 0.22835(10) 0.0396(3) Uani 1 1 d . . . . .
H8 H 0.062821 0.704009 0.197408 0.048 Uiso 1 1 calc R U . . .
C9 C 0.25582(12) 0.73171(11) 0.26131(9) 0.0367(3) Uani 1 1 d . . . . .
C10 C 0.34980(12) 0.65494(11) 0.30282(9) 0.0347(3) Uani 1 1 d . . . . .
C11 C 0.47569(13) 0.68581(12) 0.33461(10) 0.0415(3) Uani 1 1 d . . . . .
H11 H 0.538337 0.634303 0.360587 0.050 Uiso 1 1 calc R U . . .
C12 C 0.50388(14) 0.79517(12) 0.32615(11) 0.0465(3) Uani 1 1 d . . . . .
H12 H 0.587825 0.818264 0.346437 0.056 Uiso 1 1 calc R U . . .
C13 C 0.41155(15) 0.87265(12) 0.28839(11) 0.0465(3) Uani 1 1 d . . . . .
H13 H 0.434415 0.946660 0.284908 0.056 Uiso 1 1 calc R U . . .
C14 C 0.28792(14) 0.84266(12) 0.25625(10) 0.0427(3) Uani 1 1 d . . . . .
H14 H 0.226167 0.895359 0.231393 0.051 Uiso 1 1 calc R U . . .
C15 C 0.43612(12) 0.43669(11) 0.38301(9) 0.0373(3) Uani 1 1 d . . . . .
H15 H 0.478230 0.498344 0.414117 0.045 Uiso 1 1 calc R U . . .
C16 C 0.48478(12) 0.32478(11) 0.40722(9) 0.0361(3) Uani 1 1 d . . . . .
C17 C 0.39838(14) 0.23865(12) 0.38894(10) 0.0432(3) Uani 1 1 d . . . . .
H17 H 0.312813 0.254436 0.364611 0.052 Uiso 1 1 calc R U . . .
C18 C 0.43583(17) 0.13097(13) 0.40580(12) 0.0524(4) Uani 1 1 d . . . . .
H18 H 0.376270 0.074028 0.392814 0.063 Uiso 1 1 calc R U . . .
C19 C 0.56105(17) 0.10713(13) 0.44181(12) 0.0567(4) Uani 1 1 d . . . . .
H19 H 0.587211 0.033647 0.452084 0.068 Uiso 1 1 calc R U . . .
C20 C 0.64798(15) 0.19081(13) 0.46279(11) 0.0500(4) Uani 1 1 d . . . . .
H20 H 0.732760 0.173482 0.488826 0.060 Uiso 1 1 calc R U . . .
C21 C 0.61298(13) 0.30088(12) 0.44625(9) 0.0390(3) Uani 1 1 d . . . . .
C22 C 0.71127(13) 0.38834(13) 0.46694(10) 0.0441(3) Uani 1 1 d . . . . .
C23 C 0.84519(16) 0.35786(18) 0.51012(14) 0.0678(5) Uani 1 1 d . . . . .
H23A H 0.877791 0.315448 0.466077 0.102 Uiso 1 1 calc R U . . .
H23B H 0.849639 0.314313 0.565556 0.102 Uiso 1 1 calc R U . . .
H23C H 0.894792 0.424106 0.526685 0.102 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
S1 O1 1.4387(10) . ?
S1 O2 1.4345(11) . ?
S1 C1 1.7618(15) . ?
S1 C7 1.7495(14) . ?
O3 C22 1.2110(19) . ?
N1 N2 1.3844(15) . ?
N1 C7 1.3895(16) . ?
N1 C10 1.3977(17) . ?
N2 C15 1.2642(18) . ?
C1 C2 1.389(2) . ?
C1 C6 1.386(2) . ?
C2 H2 0.9400 . ?
C2 C3 1.384(2) . ?
C3 H3 0.9400 . ?
C3 C4 1.383(2) . ?
C4 H4 0.9400 . ?
C4 C5 1.378(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9400 . ?
C7 C8 1.3603(19) . ?
C8 H8 0.9400 . ?
C8 C9 1.4256(19) . ?
C9 C10 1.4151(18) . ?
C9 C14 1.402(2) . ?
C10 C11 1.3984(19) . ?
C11 H11 0.9400 . ?
C11 C12 1.379(2) . ?
C12 H12 0.9400 . ?
C12 C13 1.396(2) . ?
C13 H13 0.9400 . ?
C13 C14 1.373(2) . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
C15 C16 1.4744(18) . ?
C16 C17 1.395(2) . ?
C16 C21 1.4146(18) . ?
C17 H17 0.9400 . ?
C17 C18 1.378(2) . ?
C18 H18 0.9400 . ?
C18 C19 1.378(2) . ?
C19 H19 0.9400 . ?
C19 C20 1.378(2) . ?
C20 H20 0.9400 . ?
C20 C21 1.398(2) . ?
C21 C22 1.494(2) . ?
C22 C23 1.499(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C1 108.58(7) . . ?
O1 S1 C7 104.64(6) . . ?
O2 S1 O1 118.55(7) . . ?
O2 S1 C1 108.42(7) . . ?
O2 S1 C7 110.48(7) . . ?
C7 S1 C1 105.37(6) . . ?
N2 N1 C7 118.92(11) . . ?
N2 N1 C10 132.17(11) . . ?
C7 N1 C10 108.38(11) . . ?
C15 N2 N1 118.04(12) . . ?
C2 C1 S1 119.19(11) . . ?
C6 C1 S1 119.97(11) . . ?
C6 C1 C2 120.79(14) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.13(15) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.37(15) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.05(16) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.44(15) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.20(14) . . ?
C5 C6 H6 120.4 . . ?
N1 C7 S1 123.44(10) . . ?
C8 C7 S1 126.19(10) . . ?
C8 C7 N1 110.21(12) . . ?
C7 C8 H8 126.6 . . ?
C7 C8 C9 106.75(12) . . ?
C9 C8 H8 126.6 . . ?
C10 C9 C8 108.21(12) . . ?
C14 C9 C8 132.24(13) . . ?
C14 C9 C10 119.50(13) . . ?
N1 C10 C9 106.39(11) . . ?
N1 C10 C11 131.90(12) . . ?
C11 C10 C9 121.58(13) . . ?
C10 C11 H11 121.5 . . ?
C12 C11 C10 117.06(13) . . ?
C12 C11 H11 121.5 . . ?
C11 C12 H12 119.0 . . ?
C11 C12 C13 122.02(14) . . ?
C13 C12 H12 119.0 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.19(14) . . ?
C14 C13 H13 119.4 . . ?
C9 C14 H14 120.7 . . ?
C13 C14 C9 118.56(13) . . ?
C13 C14 H14 120.7 . . ?
N2 C15 H15 120.9 . . ?
N2 C15 C16 118.26(12) . . ?
C16 C15 H15 120.9 . . ?
C17 C16 C15 117.27(12) . . ?
C17 C16 C21 119.10(13) . . ?
C21 C16 C15 123.63(12) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.39(14) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.69(15) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.13(15) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.2 . . ?
C19 C20 C21 121.53(15) . . ?
C21 C20 H20 119.2 . . ?
C16 C21 C22 122.30(12) . . ?
C20 C21 C16 118.13(14) . . ?
C20 C21 C22 119.54(13) . . ?
O3 C22 C21 121.57(13) . . ?
O3 C22 C23 118.73(15) . . ?
C21 C22 C23 119.69(14) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 -176.70(11) . . . . ?
S1 C1 C6 C5 176.87(10) . . . . ?
S1 C7 C8 C9 176.68(11) . . . . ?
O1 S1 C1 C2 53.45(12) . . . . ?
O1 S1 C1 C6 -124.12(11) . . . . ?
O1 S1 C7 N1 179.59(12) . . . . ?
O1 S1 C7 C8 4.54(15) . . . . ?
O2 S1 C1 C2 -176.50(10) . . . . ?
O2 S1 C1 C6 5.93(13) . . . . ?
O2 S1 C7 N1 50.92(14) . . . . ?
O2 S1 C7 C8 -124.14(13) . . . . ?
N1 N2 C15 C16 179.47(11) . . . . ?
N1 C7 C8 C9 1.07(16) . . . . ?
N1 C10 C11 C12 177.01(14) . . . . ?
N2 N1 C7 S1 9.31(18) . . . . ?
N2 N1 C7 C8 -174.94(12) . . . . ?
N2 N1 C10 C9 173.84(13) . . . . ?
N2 N1 C10 C11 -1.9(3) . . . . ?
N2 C15 C16 C17 -25.62(19) . . . . ?
N2 C15 C16 C21 153.49(13) . . . . ?
C1 S1 C7 N1 -65.99(13) . . . . ?
C1 S1 C7 C8 118.95(14) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C6 C1 C2 C3 0.9(2) . . . . ?
C7 S1 C1 C2 -58.20(12) . . . . ?
C7 S1 C1 C6 124.23(11) . . . . ?
C7 N1 N2 C15 -160.33(13) . . . . ?
C7 N1 C10 C9 2.52(15) . . . . ?
C7 N1 C10 C11 -173.23(14) . . . . ?
C7 C8 C9 C10 0.52(15) . . . . ?
C7 C8 C9 C14 178.07(15) . . . . ?
C8 C9 C10 N1 -1.88(15) . . . . ?
C8 C9 C10 C11 174.41(12) . . . . ?
C8 C9 C14 C13 -174.53(14) . . . . ?
C9 C10 C11 C12 1.8(2) . . . . ?
C10 N1 N2 C15 29.1(2) . . . . ?
C10 N1 C7 S1 -178.04(10) . . . . ?
C10 N1 C7 C8 -2.29(16) . . . . ?
C10 C9 C14 C13 2.8(2) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C11 C12 C13 C14 -1.2(2) . . . . ?
C12 C13 C14 C9 -0.5(2) . . . . ?
C14 C9 C10 N1 -179.79(12) . . . . ?
C14 C9 C10 C11 -3.5(2) . . . . ?
C15 C16 C17 C18 177.41(14) . . . . ?
C15 C16 C21 C20 -177.57(13) . . . . ?
C15 C16 C21 C22 0.3(2) . . . . ?
C16 C17 C18 C19 0.2(2) . . . . ?
C16 C21 C22 O3 -1.7(2) . . . . ?
C16 C21 C22 C23 178.75(14) . . . . ?
C17 C16 C21 C20 1.5(2) . . . . ?
C17 C16 C21 C22 179.38(13) . . . . ?
C17 C18 C19 C20 1.5(3) . . . . ?
C18 C19 C20 C21 -1.6(3) . . . . ?
C19 C20 C21 C16 0.1(2) . . . . ?
C19 C20 C21 C22 -177.78(15) . . . . ?
C20 C21 C22 O3 176.14(15) . . . . ?
C20 C21 C22 C23 -3.4(2) . . . . ?
C21 C16 C17 C18 -1.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_nlg_mf_0m
_database_code_depnum_ccdc_archive 'CCDC 2393057'
loop_
_audit_author_name
_audit_author_address
'Ying He'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-10-23 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
_audit_creation_date             2024-10-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 N2 O3 S'
_chemical_formula_sum            'C23 H20 N2 O3 S'
_chemical_formula_weight         404.47
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.84300(10)
_cell_length_b                   12.3300(2)
_cell_length_c                   18.0497(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1968.03(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    193.15
_cell_measurement_theta_max      68.216
_cell_measurement_theta_min      4.343
_shelx_estimated_absorpt_T_max   0.849
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    1.689
_exptl_absorpt_correction_T_max  0.3201
_exptl_absorpt_correction_T_min  0.2151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1205 before and 0.0590 after correction.
The Ratio of minimum to maximum transmission is 0.6720.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            40924
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.217
_diffrn_reflns_theta_min         4.343
_diffrn_ambient_temperature      193.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3548
_reflns_number_total             3603
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.034(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3603
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0251
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+0.1819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0672
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups, H23A of C23
 At 1.2 times of:
  H14 of C14, H4 of C4, H20 of C20, H17 of C17, H18 of C18, H7 of C7, H3A of
  C3, H22 of C22, H9 of C9, H15 of C15, H19 of C19, H5 of C5, H12 of C12, H13
  of C13, H6 of C6, H1 of C1
2.a Ternary CH refined with riding coordinates:
 C15(H15), C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3A), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13),
 C14(H14), C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), C23(H23A)
;
_atom_sites_solution_hydrogens   mixed
_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
S1 S 0.51060(5) 0.67286(3) 0.17347(2) 0.03387(13) Uani 1 1 d . . . . .
C1 C 0.3525(3) 0.79409(18) 0.07397(12) 0.0471(5) Uani 1 1 d . . . . .
H1 H 0.380849 0.741081 0.038393 0.056 Uiso 1 1 calc R U . . .
O1 O 0.65383(17) 0.71202(12) 0.19992(9) 0.0473(4) Uani 1 1 d . . . . .
N1 N 0.29886(18) 0.54946(13) 0.25147(8) 0.0329(3) Uani 1 1 d . . . . .
C2 C 0.3982(2) 0.78401(15) 0.14737(11) 0.0351(4) Uani 1 1 d . . . . .
N2 N 0.22199(17) 0.51338(11) 0.18820(8) 0.0293(3) Uani 1 1 d . . . . .
O2 O 0.51098(17) 0.59596(10) 0.11313(8) 0.0432(3) Uani 1 1 d . . . . .
O3 O 0.37653(17) 0.37904(11) 0.13087(9) 0.0464(3) Uani 1 1 d . . . . .
H3 H 0.398973 0.436189 0.108047 0.070 Uiso 1 1 calc R U . . .
C3 C 0.3580(2) 0.86043(16) 0.20009(12) 0.0419(4) Uani 1 1 d . . . . .
H3A H 0.390277 0.853145 0.250053 0.050 Uiso 1 1 calc R U . . .
C4 C 0.2698(3) 0.94779(17) 0.17836(15) 0.0510(5) Uani 1 1 d . . . . .
H4 H 0.240685 1.000873 0.213742 0.061 Uiso 1 1 calc R U . . .
C5 C 0.2241(3) 0.95799(19) 0.10558(16) 0.0583(6) Uani 1 1 d . . . . .
H5 H 0.163527 1.018087 0.091308 0.070 Uiso 1 1 calc R U . . .
C6 C 0.2654(3) 0.8820(2) 0.05340(14) 0.0588(6) Uani 1 1 d . . . . .
H6 H 0.233958 0.890075 0.003368 0.071 Uiso 1 1 calc R U . . .
C7 C 0.3779(2) 0.54665(18) 0.44597(11) 0.0413(4) Uani 1 1 d . . . . .
H7 H 0.450086 0.579365 0.477899 0.050 Uiso 1 1 calc R U . . .
C8 C 0.3789(2) 0.56826(15) 0.36933(10) 0.0342(4) Uani 1 1 d . . . . .
C9 C 0.4724(2) 0.63238(15) 0.32276(10) 0.0365(4) Uani 1 1 d . . . . .
H9 H 0.554006 0.677175 0.338099 0.044 Uiso 1 1 calc R U . . .
C10 C 0.4231(2) 0.61759(14) 0.25177(10) 0.0316(4) Uani 1 1 d . . . . .
C11 C 0.2714(2) 0.51698(14) 0.32372(10) 0.0326(4) Uani 1 1 d . . . . .
C12 C 0.1630(2) 0.44581(18) 0.35159(11) 0.0416(4) Uani 1 1 d . . . . .
H12 H 0.091813 0.411116 0.320086 0.050 Uiso 1 1 calc R U . . .
C13 C 0.1638(3) 0.42810(18) 0.42706(11) 0.0448(5) Uani 1 1 d . . . . .
H13 H 0.090072 0.381232 0.448045 0.054 Uiso 1 1 calc R U . . .
C14 C 0.2702(3) 0.47728(17) 0.47350(11) 0.0436(5) Uani 1 1 d . . . . .
H14 H 0.267958 0.462376 0.525129 0.052 Uiso 1 1 calc R U . . .
C15 C 0.0576(2) 0.54209(15) 0.18729(9) 0.0323(4) Uani 1 1 d . . . . .
H15 H 0.018281 0.542373 0.239237 0.039 Uiso 1 1 calc R U . . .
C16 C -0.0078(2) 0.44661(15) 0.14650(9) 0.0343(4) Uani 1 1 d . . . . .
C17 C -0.1540(2) 0.43269(19) 0.11958(11) 0.0443(5) Uani 1 1 d . . . . .
H17 H -0.227657 0.488302 0.124623 0.053 Uiso 1 1 calc R U . . .
C18 C -0.1892(3) 0.3352(2) 0.08513(13) 0.0565(6) Uani 1 1 d . . . . .
H18 H -0.288852 0.323684 0.067136 0.068 Uiso 1 1 calc R U . . .
C19 C -0.0821(3) 0.2545(2) 0.07648(14) 0.0605(6) Uani 1 1 d . . . . .
H19 H -0.108602 0.188784 0.052215 0.073 Uiso 1 1 calc R U . . .
C20 C 0.0632(3) 0.26879(18) 0.10293(14) 0.0510(5) Uani 1 1 d . . . . .
H20 H 0.137168 0.213542 0.097117 0.061 Uiso 1 1 calc R U . . .
C21 C 0.0989(2) 0.36546(15) 0.13814(10) 0.0365(4) Uani 1 1 d . . . . .
C22 C 0.2456(2) 0.39686(14) 0.17397(11) 0.0355(4) Uani 1 1 d . . . . .
H22 H 0.255924 0.357794 0.222255 0.043 Uiso 1 1 calc R U . . .
C23 C 0.0293(2) 0.65208(16) 0.15248(13) 0.0430(5) Uani 1 1 d . . . . .
H23A H 0.064916 0.652928 0.109351 0.065 Uiso 1 1 calc R U . . .
H23B H 0.092(3) 0.717(2) 0.1825(14) 0.049(6) Uiso 1 1 d . . . . .
H23C H -0.085(4) 0.673(3) 0.1528(17) 0.076(9) Uiso 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
S1 O1 1.4372(16) . ?
S1 C2 1.757(2) . ?
S1 O2 1.4440(13) . ?
S1 C10 1.7496(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.391(3) . ?
C1 C6 1.381(3) . ?
N1 N2 1.401(2) . ?
N1 C10 1.383(2) . ?
N1 C11 1.386(2) . ?
C2 C3 1.386(3) . ?
N2 C15 1.496(2) . ?
N2 C22 1.474(2) . ?
O3 H3 0.8400 . ?
O3 C22 1.412(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.409(3) . ?
C7 C14 1.373(3) . ?
C8 C9 1.420(3) . ?
C8 C11 1.407(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.366(3) . ?
C11 C12 1.394(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.399(3) . ?
C14 H14 0.9500 . ?
C15 H15 1.0000 . ?
C15 C16 1.504(2) . ?
C15 C23 1.515(3) . ?
C16 C17 1.392(3) . ?
C16 C21 1.384(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(3) . ?
C21 C22 1.500(3) . ?
C22 H22 1.0000 . ?
C23 H23A 0.8400 . ?
C23 H23B 1.12(3) . ?
C23 H23C 1.04(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C2 109.00(9) . . ?
O1 S1 O2 117.98(9) . . ?
O1 S1 C10 104.62(9) . . ?
O2 S1 C2 108.13(9) . . ?
O2 S1 C10 110.76(8) . . ?
C10 S1 C2 105.67(8) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
C6 C1 C2 119.2(2) . . ?
C10 N1 N2 125.55(14) . . ?
C10 N1 C11 108.12(14) . . ?
C11 N1 N2 126.17(15) . . ?
C1 C2 S1 119.31(15) . . ?
C3 C2 S1 119.42(16) . . ?
C3 C2 C1 121.27(19) . . ?
N1 N2 C15 113.90(13) . . ?
N1 N2 C22 112.50(14) . . ?
C22 N2 C15 111.48(14) . . ?
C22 O3 H3 109.5 . . ?
C2 C3 H3A 120.7 . . ?
C2 C3 C4 118.6(2) . . ?
C4 C3 H3A 120.7 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 H6 120.1 . . ?
C8 C7 H7 120.7 . . ?
C14 C7 H7 120.7 . . ?
C14 C7 C8 118.53(19) . . ?
C7 C8 C9 133.66(18) . . ?
C11 C8 C7 119.02(18) . . ?
C11 C8 C9 107.29(16) . . ?
C8 C9 H9 126.4 . . ?
C10 C9 C8 107.16(16) . . ?
C10 C9 H9 126.4 . . ?
N1 C10 S1 125.79(13) . . ?
C9 C10 S1 124.37(14) . . ?
C9 C10 N1 109.79(15) . . ?
N1 C11 C8 107.60(16) . . ?
N1 C11 C12 129.95(17) . . ?
C12 C11 C8 122.43(17) . . ?
C11 C12 H12 121.5 . . ?
C13 C12 C11 116.9(2) . . ?
C13 C12 H12 121.5 . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.8(2) . . ?
C14 C13 H13 119.1 . . ?
C7 C14 C13 121.32(18) . . ?
C7 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
N2 C15 H15 109.2 . . ?
N2 C15 C16 101.16(14) . . ?
N2 C15 C23 112.14(15) . . ?
C16 C15 H15 109.2 . . ?
C16 C15 C23 115.73(15) . . ?
C23 C15 H15 109.2 . . ?
C17 C16 C15 128.63(18) . . ?
C21 C16 C15 110.94(16) . . ?
C21 C16 C17 120.43(18) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 C16 118.1(2) . . ?
C18 C17 H17 121.0 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.4(2) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.7 . . ?
C19 C20 C21 118.7(2) . . ?
C21 C20 H20 120.7 . . ?
C16 C21 C20 121.07(19) . . ?
C16 C21 C22 110.86(16) . . ?
C20 C21 C22 128.03(19) . . ?
N2 C22 C21 101.78(14) . . ?
N2 C22 H22 109.3 . . ?
O3 C22 N2 111.33(15) . . ?
O3 C22 C21 115.55(15) . . ?
O3 C22 H22 109.3 . . ?
C21 C22 H22 109.3 . . ?
C15 C23 H23A 109.5 . . ?
C15 C23 H23B 111.0(13) . . ?
C15 C23 H23C 112.0(18) . . ?
H23A C23 H23B 104.7 . . ?
H23A C23 H23C 111.5 . . ?
H23B C23 H23C 108(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C2 C3 C4 179.74(16) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
O1 S1 C2 C1 117.70(17) . . . . ?
O1 S1 C2 C3 -61.67(17) . . . . ?
O1 S1 C10 N1 -164.92(16) . . . . ?
O1 S1 C10 C9 12.24(18) . . . . ?
N1 N2 C15 C16 -147.37(13) . . . . ?
N1 N2 C15 C23 88.72(18) . . . . ?
N1 N2 C22 O3 -87.43(18) . . . . ?
N1 N2 C22 C21 148.90(14) . . . . ?
N1 C11 C12 C13 179.4(2) . . . . ?
C2 S1 C10 N1 80.07(17) . . . . ?
C2 S1 C10 C9 -102.77(17) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
N2 N1 C10 S1 -0.1(3) . . . . ?
N2 N1 C10 C9 -177.63(16) . . . . ?
N2 N1 C11 C8 176.86(16) . . . . ?
N2 N1 C11 C12 -1.9(3) . . . . ?
N2 C15 C16 C17 -170.73(17) . . . . ?
N2 C15 C16 C21 10.26(18) . . . . ?
O2 S1 C2 C1 -11.71(18) . . . . ?
O2 S1 C2 C3 168.92(15) . . . . ?
O2 S1 C10 N1 -36.80(19) . . . . ?
O2 S1 C10 C9 140.36(16) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C6 C1 C2 S1 -179.38(18) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C7 C8 C9 C10 176.9(2) . . . . ?
C7 C8 C11 N1 -178.53(17) . . . . ?
C7 C8 C11 C12 0.4(3) . . . . ?
C8 C7 C14 C13 0.4(3) . . . . ?
C8 C9 C10 S1 -175.61(13) . . . . ?
C8 C9 C10 N1 1.9(2) . . . . ?
C8 C11 C12 C13 0.7(3) . . . . ?
C9 C8 C11 N1 -0.2(2) . . . . ?
C9 C8 C11 C12 178.73(18) . . . . ?
C10 S1 C2 C1 -130.34(16) . . . . ?
C10 S1 C2 C3 50.28(17) . . . . ?
C10 N1 N2 C15 -121.85(18) . . . . ?
C10 N1 N2 C22 110.04(19) . . . . ?
C10 N1 C11 C8 1.4(2) . . . . ?
C10 N1 C11 C12 -177.45(19) . . . . ?
C11 N1 N2 C15 63.4(2) . . . . ?
C11 N1 N2 C22 -64.7(2) . . . . ?
C11 N1 C10 S1 175.42(13) . . . . ?
C11 N1 C10 C9 -2.1(2) . . . . ?
C11 C8 C9 C10 -1.1(2) . . . . ?
C11 C12 C13 C14 -1.3(3) . . . . ?
C12 C13 C14 C7 0.8(3) . . . . ?
C14 C7 C8 C9 -178.7(2) . . . . ?
C14 C7 C8 C11 -0.9(3) . . . . ?
C15 N2 C22 O3 143.21(15) . . . . ?
C15 N2 C22 C21 19.54(18) . . . . ?
C15 C16 C17 C18 -178.26(18) . . . . ?
C15 C16 C21 C20 179.13(18) . . . . ?
C15 C16 C21 C22 1.4(2) . . . . ?
C16 C17 C18 C19 -1.0(3) . . . . ?
C16 C21 C22 N2 -12.5(2) . . . . ?
C16 C21 C22 O3 -133.30(16) . . . . ?
C17 C16 C21 C20 0.0(3) . . . . ?
C17 C16 C21 C22 -177.75(16) . . . . ?
C17 C18 C19 C20 0.7(4) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C19 C20 C21 C16 -0.4(3) . . . . ?
C19 C20 C21 C22 177.0(2) . . . . ?
C20 C21 C22 N2 169.9(2) . . . . ?
C20 C21 C22 O3 49.1(3) . . . . ?
C21 C16 C17 C18 0.7(3) . . . . ?
C22 N2 C15 C16 -18.74(18) . . . . ?
C22 N2 C15 C23 -142.65(16) . . . . ?
C23 C15 C16 C17 -49.3(3) . . . . ?
C23 C15 C16 C21 131.68(17) . . . . ?

_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_cu_240523lu_nlg_lmf_0m
_database_code_depnum_ccdc_archive 'CCDC 2359270'
loop_
_audit_author_name
_audit_author_address
'Ying He'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-30 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
_audit_creation_date             2024-05-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 N2 O3 S'
_chemical_formula_sum            'C23 H18 N2 O3 S'
_chemical_formula_weight         402.45
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.3879(8)
_cell_length_b                   12.8676(13)
_cell_length_c                   9.7824(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.619(3)
_cell_angle_gamma                90
_cell_volume                     981.56(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9835
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.457
_cell_measurement_theta_min      3.435
_shelx_estimated_absorpt_T_max   0.849
_shelx_estimated_absorpt_T_min   0.810
_exptl_absorpt_coefficient_mu    1.693
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1153 before and 0.0668 after correction.
The Ratio of minimum to maximum transmission is 0.7779.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16483
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.452
_diffrn_reflns_theta_min         5.673
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                3431
_reflns_number_total             3435
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1549 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.090(4)
_refine_ls_extinction_coef       0.032(2)
_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   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3435
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0246
_refine_ls_restrained_S_all      1.076
_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)+(0.0155P)²+0.2226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0596
_refine_ls_wR_factor_ref         0.0596
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C15(H15)
1.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C19(H19), C20(H20), C21(H21), C22(H22)
1.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_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
S1 S 0.23253(6) 0.36296(4) 0.25139(5) 0.02475(15) Uani 1 1 d . . . . .
O1 O 0.1987(2) 0.25874(12) 0.28606(17) 0.0349(4) Uani 1 1 d . . . . .
O2 O 0.35997(19) 0.38160(13) 0.18884(17) 0.0353(4) Uani 1 1 d . . . . .
O3 O 0.28994(19) 0.66773(14) 0.19832(19) 0.0392(4) Uani 1 1 d . . . . .
N1 N 0.3579(2) 0.53131(13) 0.44093(18) 0.0231(4) Uani 1 1 d . . . . .
N2 N 0.4768(2) 0.56891(13) 0.38573(18) 0.0228(4) Uani 1 1 d . . . . .
C1 C -0.1130(3) 0.39195(18) 0.1547(3) 0.0351(5) Uani 1 1 d . . . . .
H1 H -0.112016 0.343618 0.228383 0.042 Uiso 1 1 calc R U . . .
C2 C -0.2644(3) 0.4373(2) 0.0641(3) 0.0439(6) Uani 1 1 d . . . . .
H2 H -0.368897 0.421013 0.076211 0.053 Uiso 1 1 calc R U . . .
C3 C -0.2643(3) 0.5059(2) -0.0436(3) 0.0446(6) Uani 1 1 d . . . . .
H3 H -0.369523 0.535069 -0.107123 0.054 Uiso 1 1 calc R U . . .
C4 C -0.1142(4) 0.5329(2) -0.0608(3) 0.0428(6) Uani 1 1 d . . . . .
H4 H -0.116028 0.581052 -0.134966 0.051 Uiso 1 1 calc R U . . .
C5 C 0.0398(3) 0.48968(19) 0.0302(2) 0.0327(5) Uani 1 1 d . . . . .
H5 H 0.144516 0.508506 0.020306 0.039 Uiso 1 1 calc R U . . .
C6 C 0.0377(3) 0.41876(15) 0.1353(2) 0.0248(4) Uani 1 1 d . . . . .
C7 C 0.2857(2) 0.43183(16) 0.4170(2) 0.0233(4) Uani 1 1 d . . . . .
C8 C 0.2255(3) 0.40824(16) 0.5253(2) 0.0260(4) Uani 1 1 d . . . . .
H8 H 0.168426 0.346065 0.533153 0.031 Uiso 1 1 calc R U . . .
C9 C 0.2642(3) 0.49447(16) 0.6248(2) 0.0238(4) Uani 1 1 d . . . . .
C10 C 0.3477(2) 0.56912(15) 0.5696(2) 0.0217(4) Uani 1 1 d . . . . .
C11 C 0.4027(3) 0.66468(16) 0.6377(2) 0.0259(4) Uani 1 1 d . . . . .
H11 H 0.461984 0.713222 0.600594 0.031 Uiso 1 1 calc R U . . .
C12 C 0.3668(3) 0.68522(17) 0.7616(2) 0.0291(5) Uani 1 1 d . . . . .
H12 H 0.401624 0.749779 0.810622 0.035 Uiso 1 1 calc R U . . .
C13 C 0.2801(3) 0.61326(18) 0.8174(2) 0.0325(5) Uani 1 1 d . . . . .
H13 H 0.256006 0.630513 0.902240 0.039 Uiso 1 1 calc R U . . .
C14 C 0.2295(3) 0.51817(18) 0.7509(2) 0.0308(5) Uani 1 1 d . . . . .
H14 H 0.172109 0.469559 0.789834 0.037 Uiso 1 1 calc R U . . .
C15 C 0.6626(3) 0.55656(17) 0.4682(2) 0.0270(4) Uani 1 1 d . . . . .
H15 H 0.694585 0.591575 0.565886 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4337(2) 0.63908(16) 0.2712(2) 0.0236(4) Uani 1 1 d . . . . .
C17 C 0.5992(3) 0.66696(16) 0.2597(2) 0.0248(4) Uani 1 1 d . . . . .
C18 C 0.7315(3) 0.61873(16) 0.3715(2) 0.0260(4) Uani 1 1 d . . . . .
C19 C 0.8990(3) 0.63263(19) 0.3824(3) 0.0382(5) Uani 1 1 d . . . . .
H19 H 0.990941 0.601526 0.460299 0.046 Uiso 1 1 calc R U . . .
C20 C 0.9303(3) 0.6930(2) 0.2772(3) 0.0418(6) Uani 1 1 d . . . . .
H20 H 1.044667 0.701513 0.281781 0.050 Uiso 1 1 calc R U . . .
C21 C 0.7976(4) 0.7408(2) 0.1662(3) 0.0400(6) Uani 1 1 d . . . . .
H21 H 0.821977 0.782028 0.095634 0.048 Uiso 1 1 calc R U . . .
C22 C 0.6300(3) 0.72959(18) 0.1563(3) 0.0338(5) Uani 1 1 d . . . . .
H22 H 0.538651 0.763592 0.081333 0.041 Uiso 1 1 calc R U . . .
C23 C 0.7185(3) 0.4444(2) 0.4909(3) 0.0397(6) Uani 1 1 d . . . . .
H23A H 0.662650 0.409663 0.550556 0.060 Uiso 1 1 calc R U . . .
H23B H 0.843223 0.440934 0.541632 0.060 Uiso 1 1 calc R U . . .
H23C H 0.685838 0.409621 0.395336 0.060 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
S1 O1 1.4371(17) . ?
S1 O2 1.4340(16) . ?
S1 C6 1.763(2) . ?
S1 C7 1.754(2) . ?
O3 C16 1.210(3) . ?
N1 N2 1.385(2) . ?
N1 C7 1.399(3) . ?
N1 C10 1.382(3) . ?
N2 C15 1.476(3) . ?
N2 C16 1.380(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.382(4) . ?
C1 C6 1.389(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(3) . ?
C7 C8 1.364(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.432(3) . ?
C9 C10 1.408(3) . ?
C9 C14 1.402(3) . ?
C10 C11 1.394(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.406(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9500 . ?
C15 H15 1.0000 . ?
C15 C18 1.506(3) . ?
C15 C23 1.509(3) . ?
C16 C17 1.477(3) . ?
C17 C18 1.386(3) . ?
C17 C22 1.389(3) . ?
C18 C19 1.381(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.381(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.382(4) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C6 108.36(10) . . ?
O1 S1 C7 104.97(9) . . ?
O2 S1 O1 120.01(10) . . ?
O2 S1 C6 108.47(10) . . ?
O2 S1 C7 109.51(9) . . ?
C7 S1 C6 104.42(9) . . ?
N2 N1 C7 125.77(17) . . ?
C10 N1 N2 121.86(16) . . ?
C10 N1 C7 107.82(16) . . ?
N1 N2 C15 121.11(16) . . ?
C16 N2 N1 122.32(15) . . ?
C16 N2 C15 114.98(16) . . ?
C2 C1 H1 120.8 . . ?
C2 C1 C6 118.4(2) . . ?
C6 C1 H1 120.8 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.6(2) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 S1 119.03(17) . . ?
C5 C6 S1 119.09(16) . . ?
C5 C6 C1 121.9(2) . . ?
N1 C7 S1 124.31(15) . . ?
C8 C7 S1 124.31(16) . . ?
C8 C7 N1 109.59(18) . . ?
C7 C8 H8 126.3 . . ?
C7 C8 C9 107.41(18) . . ?
C9 C8 H8 126.3 . . ?
C10 C9 C8 106.74(18) . . ?
C14 C9 C8 134.3(2) . . ?
C14 C9 C10 118.87(19) . . ?
N1 C10 C9 108.40(17) . . ?
N1 C10 C11 128.72(18) . . ?
C11 C10 C9 122.86(19) . . ?
C10 C11 H11 121.7 . . ?
C12 C11 C10 116.65(19) . . ?
C12 C11 H11 121.7 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.8(2) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C9 C14 H14 120.6 . . ?
C13 C14 C9 118.7(2) . . ?
C13 C14 H14 120.6 . . ?
N2 C15 H15 109.3 . . ?
N2 C15 C18 99.89(16) . . ?
N2 C15 C23 113.05(18) . . ?
C18 C15 H15 109.3 . . ?
C18 C15 C23 115.52(19) . . ?
C23 C15 H15 109.3 . . ?
O3 C16 N2 125.71(18) . . ?
O3 C16 C17 129.90(19) . . ?
N2 C16 C17 104.38(16) . . ?
C18 C17 C16 109.43(17) . . ?
C18 C17 C22 121.7(2) . . ?
C22 C17 C16 128.91(19) . . ?
C17 C18 C15 110.66(17) . . ?
C19 C18 C15 129.4(2) . . ?
C19 C18 C17 119.9(2) . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.7(2) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.8(2) . . ?
C22 C21 H21 119.6 . . ?
C17 C22 H22 121.1 . . ?
C21 C22 C17 117.9(2) . . ?
C21 C22 H22 121.1 . . ?
C15 C23 H23A 109.5 . . ?
C15 C23 H23B 109.5 . . ?
C15 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C7 C8 C9 -166.80(15) . . . . ?
O1 S1 C6 C1 34.2(2) . . . . ?
O1 S1 C6 C5 -147.28(17) . . . . ?
O1 S1 C7 N1 167.90(16) . . . . ?
O1 S1 C7 C8 -29.0(2) . . . . ?
O2 S1 C6 C1 166.05(17) . . . . ?
O2 S1 C6 C5 -15.5(2) . . . . ?
O2 S1 C7 N1 37.81(19) . . . . ?
O2 S1 C7 C8 -159.05(18) . . . . ?
O3 C16 C17 C18 177.1(2) . . . . ?
O3 C16 C17 C22 -3.7(4) . . . . ?
N1 N2 C15 C18 -174.28(17) . . . . ?
N1 N2 C15 C23 62.4(3) . . . . ?
N1 N2 C16 O3 -7.3(3) . . . . ?
N1 N2 C16 C17 173.67(17) . . . . ?
N1 C7 C8 C9 -1.5(2) . . . . ?
N1 C10 C11 C12 176.0(2) . . . . ?
N2 N1 C7 S1 -36.5(3) . . . . ?
N2 N1 C7 C8 158.25(18) . . . . ?
N2 N1 C10 C9 -159.05(17) . . . . ?
N2 N1 C10 C11 22.7(3) . . . . ?
N2 C15 C18 C17 5.4(2) . . . . ?
N2 C15 C18 C19 -175.3(2) . . . . ?
N2 C16 C17 C18 -3.9(2) . . . . ?
N2 C16 C17 C22 175.3(2) . . . . ?
C1 C2 C3 C4 -1.8(4) . . . . ?
C2 C1 C6 S1 179.21(19) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C4 C5 C6 S1 179.82(18) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
C6 S1 C7 N1 -78.18(18) . . . . ?
C6 S1 C7 C8 84.96(19) . . . . ?
C6 C1 C2 C3 1.0(4) . . . . ?
C7 S1 C6 C1 -77.25(19) . . . . ?
C7 S1 C6 C5 101.23(18) . . . . ?
C7 N1 N2 C15 -89.7(2) . . . . ?
C7 N1 N2 C16 105.5(2) . . . . ?
C7 N1 C10 C9 -1.7(2) . . . . ?
C7 N1 C10 C11 -179.95(19) . . . . ?
C7 C8 C9 C10 0.5(2) . . . . ?
C7 C8 C9 C14 176.8(2) . . . . ?
C8 C9 C10 N1 0.8(2) . . . . ?
C8 C9 C10 C11 179.15(18) . . . . ?
C8 C9 C14 C13 -176.7(2) . . . . ?
C9 C10 C11 C12 -2.0(3) . . . . ?
C10 N1 N2 C15 63.5(3) . . . . ?
C10 N1 N2 C16 -101.4(2) . . . . ?
C10 N1 C7 S1 167.31(14) . . . . ?
C10 N1 C7 C8 2.0(2) . . . . ?
C10 C9 C14 C13 -0.7(3) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C12 C13 C14 C9 -0.8(3) . . . . ?
C14 C9 C10 N1 -176.21(18) . . . . ?
C14 C9 C10 C11 2.2(3) . . . . ?
C15 N2 C16 O3 -173.0(2) . . . . ?
C15 N2 C16 C17 8.0(2) . . . . ?
C15 C18 C19 C20 179.0(2) . . . . ?
C16 N2 C15 C18 -8.4(2) . . . . ?
C16 N2 C15 C23 -131.7(2) . . . . ?
C16 C17 C18 C15 -1.2(2) . . . . ?
C16 C17 C18 C19 179.4(2) . . . . ?
C16 C17 C22 C21 -177.7(2) . . . . ?
C17 C18 C19 C20 -1.8(3) . . . . ?
C18 C17 C22 C21 1.4(3) . . . . ?
C18 C19 C20 C21 1.8(4) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C21 C22 C17 -1.4(3) . . . . ?
C22 C17 C18 C15 179.53(19) . . . . ?
C22 C17 C18 C19 0.1(3) . . . . ?
C23 C15 C18 C17 127.0(2) . . . . ?
C23 C15 C18 C19 -53.7(3) . . . . ?

_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_cu_240608lu_nlg_lmf_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2362138'
loop_
_audit_author_name
_audit_author_address
'Ying He'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-06-12 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
_audit_creation_date             2024-06-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 N2 O3 S'
_chemical_formula_sum            'C23 H18 N2 O3 S'
_chemical_formula_weight         402.45
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.3907(4)
_cell_length_b                   12.8791(6)
_cell_length_c                   9.7624(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.3930(10)
_cell_angle_gamma                90
_cell_volume                     982.28(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.279
_cell_measurement_theta_min      3.432
_shelx_estimated_absorpt_T_max   0.849
_shelx_estimated_absorpt_T_min   0.798
_exptl_absorpt_coefficient_mu    1.691
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1170 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.7517.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15494
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.274
_diffrn_reflns_theta_min         4.865
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_full    0.876
_reflns_Friedel_fraction_max     0.873
_reflns_number_gt                3358
_reflns_number_total             3365
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 1471 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.074(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3365
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0266
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+0.2135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0667
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C18(H18)
1.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C20(H20), C21(H21), C22(H22), C23(H23)
1.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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
S1 S 0.23272(6) 0.63725(4) 0.25103(5) 0.02490(15) Uani 1 1 d . . . . .
O1 O 0.1989(2) 0.74138(14) 0.28583(18) 0.0353(4) Uani 1 1 d . . . . .
O2 O 0.3600(2) 0.61853(15) 0.18816(18) 0.0358(4) Uani 1 1 d . . . . .
O3 O 0.2907(2) 0.33221(15) 0.19849(19) 0.0392(4) Uani 1 1 d . . . . .
N1 N 0.3581(2) 0.46925(15) 0.44053(19) 0.0234(4) Uani 1 1 d . . . . .
N2 N 0.4772(2) 0.43129(15) 0.38537(19) 0.0234(4) Uani 1 1 d . . . . .
C1 C 0.2647(3) 0.50591(18) 0.6246(2) 0.0237(4) Uani 1 1 d . . . . .
C2 C 0.2298(3) 0.4822(2) 0.7513(2) 0.0312(5) Uani 1 1 d . . . . .
H2 H 0.172458 0.530719 0.790536 0.037 Uiso 1 1 calc R U . . .
C3 C 0.2804(3) 0.3872(2) 0.8175(3) 0.0322(5) Uani 1 1 d . . . . .
H3 H 0.256298 0.370081 0.902593 0.039 Uiso 1 1 calc R U . . .
C4 C 0.3667(3) 0.31522(19) 0.7618(3) 0.0294(5) Uani 1 1 d . . . . .
H4 H 0.401189 0.250716 0.810903 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4028(3) 0.33580(18) 0.6374(2) 0.0260(5) Uani 1 1 d . . . . .
H5 H 0.462244 0.287408 0.600057 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3476(3) 0.43115(17) 0.5694(2) 0.0217(4) Uani 1 1 d . . . . .
C7 C 0.2259(3) 0.59189(18) 0.5253(2) 0.0261(4) Uani 1 1 d . . . . .
H7 H 0.168833 0.653969 0.533446 0.031 Uiso 1 1 calc R U . . .
C8 C 0.2859(3) 0.56836(17) 0.4166(2) 0.0231(4) Uani 1 1 d . . . . .
C9 C 0.0381(3) 0.58144(17) 0.1352(2) 0.0251(5) Uani 1 1 d . . . . .
C10 C -0.1129(3) 0.6088(2) 0.1545(3) 0.0360(6) Uani 1 1 d . . . . .
H10 H -0.112150 0.657508 0.227886 0.043 Uiso 1 1 calc R U . . .
C11 C -0.2642(3) 0.5633(2) 0.0639(3) 0.0447(6) Uani 1 1 d . . . . .
H11 H -0.368586 0.579727 0.076109 0.054 Uiso 1 1 calc R U . . .
C12 C -0.2640(4) 0.4946(2) -0.0432(3) 0.0449(7) Uani 1 1 d . . . . .
H12 H -0.369141 0.465574 -0.106657 0.054 Uiso 1 1 calc R U . . .
C13 C -0.1136(4) 0.4669(2) -0.0601(3) 0.0431(6) Uani 1 1 d . . . . .
H13 H -0.115088 0.418362 -0.133880 0.052 Uiso 1 1 calc R U . . .
C14 C 0.0398(3) 0.5101(2) 0.0306(3) 0.0327(5) Uani 1 1 d . . . . .
H14 H 0.144459 0.490788 0.020836 0.039 Uiso 1 1 calc R U . . .
C15 C 0.4345(3) 0.36112(18) 0.2714(2) 0.0237(4) Uani 1 1 d . . . . .
C16 C 0.5998(3) 0.33335(18) 0.2596(2) 0.0248(4) Uani 1 1 d . . . . .
C17 C 0.7316(3) 0.38169(18) 0.3714(2) 0.0269(5) Uani 1 1 d . . . . .
C18 C 0.6629(3) 0.44387(19) 0.4684(3) 0.0280(5) Uani 1 1 d . . . . .
H18 H 0.694413 0.408932 0.566171 0.034 Uiso 1 1 calc R U . . .
C19 C 0.7187(3) 0.5560(2) 0.4907(3) 0.0407(6) Uani 1 1 d . . . . .
H19A H 0.684973 0.590773 0.395070 0.061 Uiso 1 1 calc R U . . .
H19B H 0.843297 0.559408 0.540137 0.061 Uiso 1 1 calc R U . . .
H19C H 0.663894 0.590536 0.551519 0.061 Uiso 1 1 calc R U . . .
C20 C 0.8996(3) 0.3677(2) 0.3829(3) 0.0389(6) Uani 1 1 d . . . . .
H20 H 0.991212 0.398764 0.460812 0.047 Uiso 1 1 calc R U . . .
C21 C 0.9310(4) 0.3073(2) 0.2776(4) 0.0430(7) Uani 1 1 d . . . . .
H21 H 1.045190 0.298939 0.281904 0.052 Uiso 1 1 calc R U . . .
C22 C 0.7987(4) 0.2592(2) 0.1667(3) 0.0402(6) Uani 1 1 d . . . . .
H22 H 0.823398 0.217886 0.096276 0.048 Uiso 1 1 calc R U . . .
C23 C 0.6309(3) 0.2705(2) 0.1568(3) 0.0341(5) Uani 1 1 d . . . . .
H23 H 0.540026 0.236189 0.082126 0.041 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
S1 O1 1.4370(19) . ?
S1 O2 1.4333(17) . ?
S1 C8 1.753(2) . ?
S1 C9 1.765(2) . ?
O3 C15 1.214(3) . ?
N1 N2 1.386(2) . ?
N1 C6 1.383(3) . ?
N1 C8 1.396(3) . ?
N2 C15 1.376(3) . ?
N2 C18 1.480(3) . ?
C1 C2 1.405(3) . ?
C1 C6 1.405(3) . ?
C1 C7 1.429(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.403(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.364(3) . ?
C9 C10 1.392(3) . ?
C9 C14 1.379(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.370(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.477(3) . ?
C16 C17 1.387(3) . ?
C16 C23 1.386(3) . ?
C17 C18 1.506(3) . ?
C17 C20 1.385(3) . ?
C18 H18 1.0000 . ?
C18 C19 1.509(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20 0.9500 . ?
C20 C21 1.388(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.383(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.383(4) . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C8 105.08(10) . . ?
O1 S1 C9 108.36(10) . . ?
O2 S1 O1 120.04(11) . . ?
O2 S1 C8 109.33(10) . . ?
O2 S1 C9 108.50(11) . . ?
C8 S1 C9 104.43(10) . . ?
N2 N1 C8 126.02(18) . . ?
C6 N1 N2 121.50(17) . . ?
C6 N1 C8 108.01(17) . . ?
N1 N2 C18 120.89(17) . . ?
C15 N2 N1 122.30(16) . . ?
C15 N2 C18 115.21(17) . . ?
C2 C1 C6 118.7(2) . . ?
C2 C1 C7 134.2(2) . . ?
C6 C1 C7 107.02(19) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 121.7 . . ?
C4 C5 C6 116.5(2) . . ?
C6 C5 H5 121.7 . . ?
N1 C6 C1 108.09(19) . . ?
N1 C6 C5 128.75(19) . . ?
C5 C6 C1 123.15(19) . . ?
C1 C7 H7 126.3 . . ?
C8 C7 C1 107.4(2) . . ?
C8 C7 H7 126.3 . . ?
N1 C8 S1 124.49(16) . . ?
C7 C8 S1 124.25(17) . . ?
C7 C8 N1 109.49(19) . . ?
C10 C9 S1 119.02(18) . . ?
C14 C9 S1 119.26(17) . . ?
C14 C9 C10 121.7(2) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.2(2) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 C13 118.9(2) . . ?
C9 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
O3 C15 N2 125.80(19) . . ?
O3 C15 C16 129.8(2) . . ?
N2 C15 C16 104.35(17) . . ?
C17 C16 C15 109.38(18) . . ?
C23 C16 C15 128.9(2) . . ?
C23 C16 C17 121.7(2) . . ?
C16 C17 C18 110.82(18) . . ?
C20 C17 C16 120.1(2) . . ?
C20 C17 C18 129.1(2) . . ?
N2 C18 C17 99.56(17) . . ?
N2 C18 H18 109.4 . . ?
N2 C18 C19 113.1(2) . . ?
C17 C18 H18 109.4 . . ?
C17 C18 C19 115.5(2) . . ?
C19 C18 H18 109.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20 120.8 . . ?
C17 C20 C21 118.4(2) . . ?
C21 C20 H20 120.8 . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 121.1(2) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.9(2) . . ?
C23 C22 H22 119.6 . . ?
C16 C23 H23 121.1 . . ?
C22 C23 C16 117.8(2) . . ?
C22 C23 H23 121.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C9 C10 C11 -179.2(2) . . . . ?
S1 C9 C14 C13 -179.8(2) . . . . ?
O1 S1 C8 N1 -167.79(17) . . . . ?
O1 S1 C8 C7 28.9(2) . . . . ?
O1 S1 C9 C10 -33.8(2) . . . . ?
O1 S1 C9 C14 147.73(19) . . . . ?
O2 S1 C8 N1 -37.7(2) . . . . ?
O2 S1 C8 C7 159.04(19) . . . . ?
O2 S1 C9 C10 -165.70(19) . . . . ?
O2 S1 C9 C14 15.9(2) . . . . ?
O3 C15 C16 C17 -177.0(2) . . . . ?
O3 C15 C16 C23 3.4(4) . . . . ?
N1 N2 C15 O3 7.1(3) . . . . ?
N1 N2 C15 C16 -173.91(19) . . . . ?
N1 N2 C18 C17 174.51(18) . . . . ?
N1 N2 C18 C19 -62.4(3) . . . . ?
N2 N1 C6 C1 158.98(18) . . . . ?
N2 N1 C6 C5 -22.4(3) . . . . ?
N2 N1 C8 S1 36.5(3) . . . . ?
N2 N1 C8 C7 -158.10(19) . . . . ?
N2 C15 C16 C17 4.1(2) . . . . ?
N2 C15 C16 C23 -175.5(2) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C1 C7 C8 S1 166.88(16) . . . . ?
C1 C7 C8 N1 1.5(2) . . . . ?
C2 C1 C6 N1 176.29(19) . . . . ?
C2 C1 C6 C5 -2.4(3) . . . . ?
C2 C1 C7 C8 -176.7(2) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 N1 -176.2(2) . . . . ?
C4 C5 C6 C1 2.3(3) . . . . ?
C6 N1 N2 C15 101.2(2) . . . . ?
C6 N1 N2 C18 -63.7(3) . . . . ?
C6 N1 C8 S1 -167.17(15) . . . . ?
C6 N1 C8 C7 -1.8(2) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C6 C1 C7 C8 -0.6(2) . . . . ?
C7 C1 C2 C3 176.6(2) . . . . ?
C7 C1 C6 N1 -0.5(2) . . . . ?
C7 C1 C6 C5 -179.24(19) . . . . ?
C8 S1 C9 C10 77.8(2) . . . . ?
C8 S1 C9 C14 -100.65(19) . . . . ?
C8 N1 N2 C15 -105.5(3) . . . . ?
C8 N1 N2 C18 89.6(3) . . . . ?
C8 N1 C6 C1 1.4(2) . . . . ?
C8 N1 C6 C5 -180.0(2) . . . . ?
C9 S1 C8 N1 78.24(19) . . . . ?
C9 S1 C8 C7 -85.0(2) . . . . ?
C9 C10 C11 C12 -1.1(4) . . . . ?
C10 C9 C14 C13 1.8(4) . . . . ?
C10 C11 C12 C13 2.0(5) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C12 C13 C14 C9 -0.9(4) . . . . ?
C14 C9 C10 C11 -0.8(4) . . . . ?
C15 N2 C18 C17 8.6(2) . . . . ?
C15 N2 C18 C19 131.7(2) . . . . ?
C15 C16 C17 C18 1.2(3) . . . . ?
C15 C16 C17 C20 -179.7(2) . . . . ?
C15 C16 C23 C22 177.9(2) . . . . ?
C16 C17 C18 N2 -5.5(2) . . . . ?
C16 C17 C18 C19 -126.9(2) . . . . ?
C16 C17 C20 C21 1.9(4) . . . . ?
C17 C16 C23 C22 -1.7(4) . . . . ?
C17 C20 C21 C22 -2.1(4) . . . . ?
C18 N2 C15 O3 172.8(2) . . . . ?
C18 N2 C15 C16 -8.2(2) . . . . ?
C18 C17 C20 C21 -179.1(3) . . . . ?
C20 C17 C18 N2 175.5(2) . . . . ?
C20 C17 C18 C19 54.0(3) . . . . ?
C20 C21 C22 C23 0.4(4) . . . . ?
C21 C22 C23 C16 1.5(4) . . . . ?
C23 C16 C17 C18 -179.2(2) . . . . ?
C23 C16 C17 C20 0.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
