# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
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data_mo_d8v22340_0m
_database_code_depnum_ccdc_archive 'CCDC 2206931'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2022-09-13 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 N O3 S'
_chemical_formula_weight         319.41

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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.3144(3)
_cell_length_b                   12.2204(4)
_cell_length_c                   13.0932(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.9460(10)
_cell_angle_gamma                90
_cell_volume                     1648.17(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    6946
_cell_measurement_theta_min      4.562
_cell_measurement_theta_max      54.664

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.208
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4746
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19731
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.586
_diffrn_reflns_theta_max         25.998
_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             3222
_reflns_number_gt                2702
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0474P)²+0.7903P] 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         3222
_refine_ls_number_parameters     247
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.109
_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
S1 S 0.23036(5) 0.46925(4) 0.35769(4) 0.04230(18) Uani 1 1 d . . . . .
O1 O 0.16099(15) 0.41449(13) 0.27562(12) 0.0586(4) Uani 1 1 d . . . . .
O2 O 0.28506(14) 0.40859(11) 0.44268(12) 0.0537(4) Uani 1 1 d . . . . .
N1 N 0.35183(15) 0.53236(13) 0.30719(12) 0.0404(4) Uani 1 1 d . . . . .
C1 C 0.3275(2) 0.59613(19) 0.21354(16) 0.0500(5) Uani 1 1 d . . . . .
H1A H 0.2634 0.6538 0.2235 0.060 Uiso 1 1 calc R U . . .
H1B H 0.2966 0.5492 0.1567 0.060 Uiso 1 1 calc R U . . .
C2 C 0.4607(2) 0.64490(17) 0.19389(16) 0.0464(5) Uani 1 1 d D . . . .
C3 C 0.53318(18) 0.64988(17) 0.30164(16) 0.0451(5) Uani 1 1 d D . . . .
C4 C 0.4363(2) 0.60058(19) 0.37416(16) 0.0490(5) Uani 1 1 d . . . . .
H4A H 0.4812 0.5564 0.4275 0.059 Uiso 1 1 calc R U . . .
H4B H 0.3865 0.6581 0.4065 0.059 Uiso 1 1 calc R U . . .
C5 C 0.4485(3) 0.7522(2) 0.1358(2) 0.0758(8) Uani 1 1 d . . . . .
H5A H 0.5342 0.7784 0.1209 0.114 Uiso 1 1 calc R U . . .
H5B H 0.4057 0.8058 0.1770 0.114 Uiso 1 1 calc R U . . .
H5C H 0.3977 0.7408 0.0722 0.114 Uiso 1 1 calc R U . . .
C6 C 0.5790(3) 0.7620(2) 0.3385(2) 0.0724(8) Uani 1 1 d . . . . .
H6A H 0.6194 0.7557 0.4068 0.109 Uiso 1 1 calc R U . . .
H6B H 0.5054 0.8112 0.3398 0.109 Uiso 1 1 calc R U . . .
H6C H 0.6415 0.7906 0.2925 0.109 Uiso 1 1 calc R U . . .
O3 O 0.5467(5) 0.5589(4) 0.1473(3) 0.0478(11) Uani 0.6 1 d D U P A 1
C7 C 0.6547(6) 0.5338(5) 0.2158(5) 0.0425(12) Uani 0.5 1 d D U P A 1
C8 C 0.7233(7) 0.4576(7) 0.1358(5) 0.0545(16) Uani 0.5 1 d D U P A 1
H8 H 0.7003 0.4428 0.0668 0.065 Uiso 0.5 1 calc R U P A 1
C9 C 0.8197(6) 0.4220(5) 0.1936(5) 0.0776(15) Uani 0.5 1 d D U P A 1
H9A H 0.8295 0.4447 0.2622 0.093 Uiso 0.5 1 calc R U P A 1
H9B H 0.8801 0.3733 0.1671 0.093 Uiso 0.5 1 calc R U P A 1
C10 C 0.6520(7) 0.5848(5) 0.3011(5) 0.0417(13) Uani 0.6 1 d D U P A 1
H10 H 0.7162 0.5809 0.3546 0.050 Uiso 0.6 1 calc R U P A 1
O3' O 0.6335(7) 0.5606(5) 0.2729(5) 0.0435(15) Uani 0.4 1 d D U P A 2
C7' C 0.6255(7) 0.5322(5) 0.1768(5) 0.0440(12) Uani 0.5 1 d D U P A 2
C8' C 0.7468(7) 0.4582(6) 0.1760(5) 0.0480(13) Uani 0.5 1 d D U P A 2
H8' H 0.8117 0.4478 0.2282 0.058 Uiso 0.5 1 calc R U P A 2
C9' C 0.7370(6) 0.4122(4) 0.0824(5) 0.0775(17) Uani 0.5 1 d D U P A 2
H9'1 H 0.6666 0.4297 0.0369 0.093 Uiso 0.5 1 calc R U P A 2
H9'2 H 0.8007 0.3626 0.0626 0.093 Uiso 0.5 1 calc R U P A 2
C10' C 0.5209(11) 0.5780(9) 0.1210(8) 0.0456(18) Uani 0.4 1 d D U P A 2
H10' H 0.4959 0.5674 0.0516 0.055 Uiso 0.4 1 calc R U P A 2
C11 C 0.12858(17) 0.57118(15) 0.40521(14) 0.0379(4) Uani 1 1 d . . . . .
C12 C 0.1451(2) 0.60372(17) 0.50615(16) 0.0452(5) Uani 1 1 d . . . . .
H12 H 0.2083 0.5701 0.5499 0.054 Uiso 1 1 calc R U . . .
C13 C 0.0682(2) 0.68583(18) 0.54208(17) 0.0510(5) Uani 1 1 d . . . . .
H13 H 0.0781 0.7065 0.6112 0.061 Uiso 1 1 calc R U . . .
C14 C -0.02312(19) 0.73861(17) 0.47875(18) 0.0497(5) Uani 1 1 d . . . . .
C15 C -0.0381(2) 0.70477(19) 0.37835(19) 0.0544(6) Uani 1 1 d . . . . .
H15 H -0.1003 0.7394 0.3344 0.065 Uiso 1 1 calc R U . . .
C16 C 0.03613(19) 0.62113(18) 0.34086(17) 0.0481(5) Uani 1 1 d . . . . .
H16 H 0.0239 0.5985 0.2724 0.058 Uiso 1 1 calc R U . . .
C17 C -0.1036(3) 0.8303(2) 0.5193(2) 0.0740(8) Uani 1 1 d . . . . .
H17A H -0.1466 0.8692 0.4625 0.111 Uiso 1 1 calc R U . . .
H17B H -0.0478 0.8803 0.5587 0.111 Uiso 1 1 calc R U . . .
H17C H -0.1683 0.8003 0.5627 0.111 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 1.4267(16) . ?
S1 O2 1.4289(15) . ?
S1 N1 1.6392(15) . ?
S1 C11 1.7630(19) . ?
N1 C1 1.463(3) . ?
N1 C4 1.464(3) . ?
C1 C2 1.531(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 C10' 1.423(11) . ?
C2 C5 1.518(3) . ?
C2 O3 1.523(5) . ?
C2 C3 1.563(3) . ?
C3 C10 1.462(7) . ?
C3 C6 1.520(3) . ?
C3 C4 1.536(3) . ?
C3 O3' 1.563(7) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
O3 C7 1.428(6) . ?
C7 C10 1.280(8) . ?
C7 C8 1.594(11) . ?
C8 C9 1.294(8) . ?
C8 H8 0.9400 . ?
C9 H9A 0.9400 . ?
C9 H9B 0.9400 . ?
C10 H10 0.9400 . ?
O3' C7' 1.303(7) . ?
C7' C10' 1.390(9) . ?
C7' C8' 1.543(9) . ?
C8' C9' 1.348(8) . ?
C8' H8' 0.9400 . ?
C9' H9'1 0.9400 . ?
C9' H9'2 0.9400 . ?
C10' H10' 0.9400 . ?
C11 C16 1.382(3) . ?
C11 C12 1.382(3) . ?
C12 C13 1.376(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.382(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.379(3) . ?
C14 C17 1.507(3) . ?
C15 C16 1.382(3) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 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 O2 120.39(10) . . ?
O1 S1 N1 106.32(9) . . ?
O2 S1 N1 106.19(9) . . ?
O1 S1 C11 108.21(9) . . ?
O2 S1 C11 108.07(9) . . ?
N1 S1 C11 106.94(8) . . ?
C1 N1 C4 105.63(15) . . ?
C1 N1 S1 119.14(13) . . ?
C4 N1 S1 118.03(13) . . ?
N1 C1 C2 103.39(16) . . ?
N1 C1 H1A 111.1 . . ?
C2 C1 H1A 111.1 . . ?
N1 C1 H1B 111.1 . . ?
C2 C1 H1B 111.1 . . ?
H1A C1 H1B 109.0 . . ?
C10' C2 C5 100.8(4) . . ?
C5 C2 O3 115.5(2) . . ?
C10' C2 C1 108.4(5) . . ?
C5 C2 C1 111.60(19) . . ?
O3 C2 C1 110.1(2) . . ?
C10' C2 C3 115.0(4) . . ?
C5 C2 C3 116.27(19) . . ?
O3 C2 C3 97.3(2) . . ?
C1 C2 C3 104.76(15) . . ?
C10 C3 C6 104.2(3) . . ?
C10 C3 C4 111.2(3) . . ?
C6 C3 C4 111.02(19) . . ?
C10 C3 C2 109.6(3) . . ?
C6 C3 C2 116.63(18) . . ?
C4 C3 C2 104.28(16) . . ?
C6 C3 O3' 120.4(3) . . ?
C4 C3 O3' 109.6(3) . . ?
C2 C3 O3' 92.7(3) . . ?
N1 C4 C3 103.83(16) . . ?
N1 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
N1 C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 O3 C2 110.3(4) . . ?
C10 C7 O3 113.1(5) . . ?
C10 C7 C8 152.6(6) . . ?
O3 C7 C8 94.1(5) . . ?
C9 C8 C7 99.6(6) . . ?
C9 C8 H8 130.2 . . ?
C7 C8 H8 130.2 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
C7 C10 C3 108.9(5) . . ?
C7 C10 H10 125.5 . . ?
C3 C10 H10 125.5 . . ?
C7' O3' C3 114.1(5) . . ?
O3' C7' C10' 114.2(7) . . ?
O3' C7' C8' 98.7(6) . . ?
C10' C7' C8' 147.1(7) . . ?
C9' C8' C7' 103.2(6) . . ?
C9' C8' H8' 128.4 . . ?
C7' C8' H8' 128.4 . . ?
C8' C9' H9'1 120.0 . . ?
C8' C9' H9'2 120.0 . . ?
H9'1 C9' H9'2 120.0 . . ?
C7' C10' C2 103.4(8) . . ?
C7' C10' H10' 128.3 . . ?
C2 C10' H10' 128.3 . . ?
C16 C11 C12 120.20(18) . . ?
C16 C11 S1 120.12(15) . . ?
C12 C11 S1 119.63(15) . . ?
C13 C12 C11 119.46(19) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 121.5(2) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 118.13(19) . . ?
C15 C14 C17 121.4(2) . . ?
C13 C14 C17 120.4(2) . . ?
C14 C15 C16 121.5(2) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C11 C16 C15 119.2(2) . . ?
C11 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O1 S1 N1 C1 46.62(18) . . . . ?
O2 S1 N1 C1 175.96(15) . . . . ?
C11 S1 N1 C1 -68.82(17) . . . . ?
O1 S1 N1 C4 176.88(15) . . . . ?
O2 S1 N1 C4 -53.77(17) . . . . ?
C11 S1 N1 C4 61.44(16) . . . . ?
C4 N1 C1 C2 42.1(2) . . . . ?
S1 N1 C1 C2 177.76(13) . . . . ?
N1 C1 C2 C10' 97.6(4) . . . . ?
N1 C1 C2 C5 -152.32(19) . . . . ?
N1 C1 C2 O3 78.0(2) . . . . ?
N1 C1 C2 C3 -25.7(2) . . . . ?
C10' C2 C3 C10 1.7(6) . . . . ?
C5 C2 C3 C10 -115.8(3) . . . . ?
O3 C2 C3 C10 7.4(4) . . . . ?
C1 C2 C3 C10 120.6(3) . . . . ?
C10' C2 C3 C6 119.7(6) . . . . ?
C5 C2 C3 C6 2.3(3) . . . . ?
O3 C2 C3 C6 125.5(3) . . . . ?
C1 C2 C3 C6 -121.4(2) . . . . ?
C10' C2 C3 C4 -117.5(5) . . . . ?
C5 C2 C3 C4 125.1(2) . . . . ?
O3 C2 C3 C4 -111.7(2) . . . . ?
C1 C2 C3 C4 1.4(2) . . . . ?
C10' C2 C3 O3' -6.5(6) . . . . ?
C5 C2 C3 O3' -123.9(3) . . . . ?
O3 C2 C3 O3' -0.8(4) . . . . ?
C1 C2 C3 O3' 112.4(3) . . . . ?
C1 N1 C4 C3 -41.3(2) . . . . ?
S1 N1 C4 C3 -177.53(13) . . . . ?
C10 C3 C4 N1 -94.7(3) . . . . ?
C6 C3 C4 N1 149.81(18) . . . . ?
C2 C3 C4 N1 23.4(2) . . . . ?
O3' C3 C4 N1 -74.8(3) . . . . ?
C10' C2 O3 C7 157(2) . . . . ?
C5 C2 O3 C7 117.7(4) . . . . ?
C1 C2 O3 C7 -114.8(4) . . . . ?
C3 C2 O3 C7 -6.0(4) . . . . ?
C2 O3 C7 C10 2.7(6) . . . . ?
C2 O3 C7 C8 -173.5(5) . . . . ?
C10 C7 C8 C9 12.5(17) . . . . ?
O3 C7 C8 C9 -175.0(5) . . . . ?
O3 C7 C10 C3 2.5(7) . . . . ?
C8 C7 C10 C3 174.3(12) . . . . ?
C6 C3 C10 C7 -132.2(4) . . . . ?
C4 C3 C10 C7 108.1(5) . . . . ?
C2 C3 C10 C7 -6.7(6) . . . . ?
O3' C3 C10 C7 19.6(14) . . . . ?
C10 C3 O3' C7' -148(2) . . . . ?
C6 C3 O3' C7' -115.9(5) . . . . ?
C4 C3 O3' C7' 113.6(5) . . . . ?
C2 C3 O3' C7' 7.4(5) . . . . ?
C3 O3' C7' C10' -6.4(9) . . . . ?
C3 O3' C7' C8' 172.9(5) . . . . ?
O3' C7' C8' C9' 171.7(5) . . . . ?
C10' C7' C8' C9' -9.5(14) . . . . ?
O3' C7' C10' C2 1.5(10) . . . . ?
C8' C7' C10' C2 -177.1(9) . . . . ?
C5 C2 C10' C7' 129.7(6) . . . . ?
O3 C2 C10' C7' -14.3(15) . . . . ?
C1 C2 C10' C7' -113.0(6) . . . . ?
C3 C2 C10' C7' 3.9(9) . . . . ?
O1 S1 C11 C16 -29.87(19) . . . . ?
O2 S1 C11 C16 -161.74(16) . . . . ?
N1 S1 C11 C16 84.30(17) . . . . ?
O1 S1 C11 C12 152.57(16) . . . . ?
O2 S1 C11 C12 20.70(18) . . . . ?
N1 S1 C11 C12 -93.26(17) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
S1 C11 C12 C13 177.89(16) . . . . ?
C11 C12 C13 C14 -1.7(3) . . . . ?
C12 C13 C14 C15 1.7(3) . . . . ?
C12 C13 C14 C17 -178.4(2) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C17 C14 C15 C16 179.6(2) . . . . ?
C12 C11 C16 C15 0.9(3) . . . . ?
S1 C11 C16 C15 -176.68(16) . . . . ?
C14 C15 C16 C11 -0.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 O2 0.94 2.66 3.385(7) 134.7 3_666
C5 H5A O2 0.97 2.62 3.543(3) 159.4 2_655
C5 H5A O2 0.97 2.62 3.543(3) 159.4 2_655
C10 H10 O2 0.94 2.66 3.385(7) 134.7 3_666
C5 H5A O2 0.97 2.62 3.543(3) 159.4 2_655
C10 H10 O2 0.94 2.66 3.385(7) 134.7 3_666
C5 H5A O2 0.97 2.62 3.543(3) 159.4 2_655
C10 H10 O2 0.94 2.66 3.385(7) 134.7 3_666

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v23120
_database_code_depnum_ccdc_archive 'CCDC 2246469'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2023-03-06 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 Cl N O3 S2'
_chemical_formula_weight         423.95

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   19.7752(8)
_cell_length_b                   9.1254(3)
_cell_length_c                   11.5285(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.4770(10)
_cell_angle_gamma                90
_cell_volume                     2067.12(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      4.922
_cell_measurement_theta_max      50.523

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.407
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5426
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28291
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.461
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4042
_reflns_number_gt                3356
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0546P)²+0.6909P] 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     SHELXL
_refine_ls_extinction_coef       0.034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4042
_refine_ls_number_parameters     266
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.077
_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 0.93846(3) 0.18270(8) 0.53174(6) 0.0743(2) Uani 1 1 d . . . . .
S2 S 0.67311(3) 0.67096(6) 0.21568(4) 0.04654(19) Uani 1 1 d . . . . .
O1 O 0.73223(7) 0.47742(15) 0.53562(12) 0.0458(3) Uani 1 1 d . . . . .
H1A H 0.7223 0.5359 0.5850 0.069 Uiso 1 1 calc R U . . .
O2 O 0.65971(9) 0.5830(2) 0.11299(13) 0.0707(5) Uani 1 1 d . . . . .
O3 O 0.69209(8) 0.82167(17) 0.20682(15) 0.0652(5) Uani 1 1 d . . . . .
N1 N 0.73432(8) 0.59276(17) 0.29562(14) 0.0449(4) Uani 1 1 d . . . . .
C1 C 0.92419(13) 0.5586(3) 0.7528(2) 0.0685(7) Uani 1 1 d D . . . .
H1 H 0.9478 0.5375 0.8252 0.082 Uiso 1 1 calc R U . A 1
C2 C 0.94407(13) 0.6637(3) 0.6845(2) 0.0708(7) Uani 1 1 d D . . . .
H2 H 0.9814 0.7252 0.7012 0.085 Uiso 1 1 calc R U . B 1
C4 C 0.84673(9) 0.56602(19) 0.57439(15) 0.0381(4) Uani 1 1 d D . . . .
C5 C 0.78874(9) 0.53154(18) 0.48267(15) 0.0350(4) Uani 1 1 d . . . . .
C6 C 0.76665(10) 0.6616(2) 0.40400(18) 0.0447(5) Uani 1 1 d . . . . .
H6A H 0.7345 0.7231 0.4392 0.054 Uiso 1 1 calc R U . . .
H6B H 0.8055 0.7205 0.3888 0.054 Uiso 1 1 calc R U . . .
C7 C 0.74022(10) 0.4313(2) 0.30206(16) 0.0427(4) Uani 1 1 d . . . . .
H7A H 0.7473 0.3896 0.2270 0.051 Uiso 1 1 calc R U . . .
H7B H 0.7001 0.3874 0.3289 0.051 Uiso 1 1 calc R U . . .
C8 C 0.80302(9) 0.41083(19) 0.39154(15) 0.0356(4) Uani 1 1 d . . . . .
C9 C 0.80521(9) 0.25840(19) 0.44036(15) 0.0369(4) Uani 1 1 d . . . . .
C10 C 0.75096(12) 0.1416(2) 0.4417(2) 0.0556(5) Uani 1 1 d . . . . .
H10A H 0.7308 0.1117 0.3647 0.067 Uiso 1 1 calc R U . . .
H10B H 0.7163 0.1639 0.4923 0.067 Uiso 1 1 calc R U . . .
C11 C 0.80740(13) 0.0382(2) 0.4967(2) 0.0590(6) Uani 1 1 d . . . . .
H11A H 0.8021 0.0068 0.5756 0.071 Uiso 1 1 calc R U . . .
H11B H 0.8174 -0.0435 0.4477 0.071 Uiso 1 1 calc R U . . .
C12 C 0.85252(11) 0.1683(2) 0.48954(17) 0.0451(5) Uani 1 1 d . . . . .
C13 C 0.86836(10) 0.4447(2) 0.33622(17) 0.0466(5) Uani 1 1 d . . . . .
H13A H 0.9065 0.4447 0.3957 0.070 Uiso 1 1 calc R U . . .
H13B H 0.8644 0.5391 0.2994 0.070 Uiso 1 1 calc R U . . .
H13C H 0.8751 0.3713 0.2789 0.070 Uiso 1 1 calc R U . . .
C14 C 0.59979(10) 0.6695(2) 0.28877(16) 0.0436(5) Uani 1 1 d . . . . .
C15 C 0.54993(13) 0.5649(3) 0.2624(3) 0.0714(7) Uani 1 1 d . . . . .
H15 H 0.5554 0.4926 0.2074 0.086 Uiso 1 1 calc R U . . .
C16 C 0.49215(15) 0.5687(4) 0.3184(3) 0.0936(10) Uani 1 1 d . . . . .
H16 H 0.4585 0.4988 0.2995 0.112 Uiso 1 1 calc R U . . .
C17 C 0.48252(13) 0.6730(4) 0.4015(3) 0.0768(8) Uani 1 1 d . . . . .
C18 C 0.53337(12) 0.7735(3) 0.4284(2) 0.0645(6) Uani 1 1 d . . . . .
H18 H 0.5285 0.8431 0.4858 0.077 Uiso 1 1 calc R U . . .
C19 C 0.59154(10) 0.7744(2) 0.37253(18) 0.0506(5) Uani 1 1 d . . . . .
H19 H 0.6249 0.8450 0.3911 0.061 Uiso 1 1 calc R U . . .
C20 C 0.41764(17) 0.6774(5) 0.4593(4) 0.1272(16) Uani 1 1 d . . . . .
H20A H 0.4264 0.7235 0.5343 0.191 Uiso 1 1 calc R U . . .
H20B H 0.4016 0.5794 0.4688 0.191 Uiso 1 1 calc R U . . .
H20C H 0.3837 0.7322 0.4114 0.191 Uiso 1 1 calc R U . . .
S1 S 0.85410(9) 0.46641(17) 0.70043(13) 0.0581(3) Uani 0.7 1 d D U P C 1
C3 C 0.8971(6) 0.6648(13) 0.5799(11) 0.0638(18) Uani 0.6 1 d D U P C 1
H3 H 0.9014 0.7304 0.5194 0.077 Uiso 0.6 1 calc R U P C 1
S1' S 0.9044(3) 0.6968(7) 0.5615(5) 0.0646(9) Uani 0.3 1 d D U P C 2
C3' C 0.8638(7) 0.4994(14) 0.6837(10) 0.069(2) Uani 0.4 1 d D U P C 2
H3' H 0.8385 0.4230 0.7102 0.083 Uiso 0.4 1 calc R U P C 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C12 1.719(2) . ?
S2 O2 1.4304(17) . ?
S2 O3 1.4322(16) . ?
S2 N1 1.6037(16) . ?
S2 C14 1.757(2) . ?
O1 C5 1.421(2) . ?
O1 H1A 0.8200 . ?
N1 C6 1.478(2) . ?
N1 C7 1.480(2) . ?
C1 C2 1.329(4) . ?
C1 C3' 1.462(11) . ?
C1 S1 1.674(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.437(11) . ?
C2 S1' 1.570(6) . ?
C2 H2 0.9300 . ?
C4 C3 1.339(9) . ?
C4 C3' 1.405(10) . ?
C4 C5 1.503(3) . ?
C4 S1' 1.668(5) . ?
C4 S1 1.706(2) . ?
C5 C6 1.527(2) . ?
C5 C8 1.570(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.534(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.499(2) . ?
C8 C13 1.535(2) . ?
C9 C12 1.324(3) . ?
C9 C10 1.514(3) . ?
C10 C11 1.542(3) . ?
C10 C12 2.036(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.493(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.381(3) . ?
C14 C19 1.383(3) . ?
C15 C16 1.375(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(4) . ?
C17 C20 1.511(4) . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C3 H3 0.9300 . ?
C3' H3' 0.9300 . ?

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
O2 S2 O3 120.38(11) . . ?
O2 S2 N1 106.45(9) . . ?
O3 S2 N1 106.35(10) . . ?
O2 S2 C14 107.86(10) . . ?
O3 S2 C14 106.17(9) . . ?
N1 S2 C14 109.34(9) . . ?
C5 O1 H1A 109.5 . . ?
C6 N1 C7 110.91(14) . . ?
C6 N1 S2 121.53(13) . . ?
C7 N1 S2 121.48(13) . . ?
C2 C1 C3' 102.8(4) . . ?
C2 C1 S1 115.9(2) . . ?
C2 C1 H1 122.0 . . ?
S1 C1 H1 122.0 . . ?
C1 C2 C3 107.2(4) . . ?
C1 C2 S1' 121.5(3) . . ?
C1 C2 H2 126.4 . . ?
C3 C2 H2 126.4 . . ?
C3 C4 C5 132.7(5) . . ?
C3' C4 C5 128.8(5) . . ?
C3' C4 S1' 107.0(5) . . ?
C5 C4 S1' 124.2(2) . . ?
C3 C4 S1 109.1(5) . . ?
C5 C4 S1 118.22(14) . . ?
O1 C5 C4 110.20(14) . . ?
O1 C5 C6 109.82(15) . . ?
C4 C5 C6 113.55(14) . . ?
O1 C5 C8 104.67(13) . . ?
C4 C5 C8 115.92(14) . . ?
C6 C5 C8 102.06(14) . . ?
N1 C6 C5 103.82(14) . . ?
N1 C6 H6A 111.0 . . ?
C5 C6 H6A 111.0 . . ?
N1 C6 H6B 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
N1 C7 C8 102.01(15) . . ?
N1 C7 H7A 111.4 . . ?
C8 C7 H7A 111.4 . . ?
N1 C7 H7B 111.4 . . ?
C8 C7 H7B 111.4 . . ?
H7A C7 H7B 109.2 . . ?
C9 C8 C7 110.62(15) . . ?
C9 C8 C13 110.64(14) . . ?
C7 C8 C13 110.59(15) . . ?
C9 C8 C5 113.55(14) . . ?
C7 C8 C5 99.88(13) . . ?
C13 C8 C5 111.12(14) . . ?
C12 C9 C8 136.56(18) . . ?
C12 C9 C10 91.47(16) . . ?
C8 C9 C10 131.81(17) . . ?
C9 C10 C11 87.36(16) . . ?
C9 C10 C12 40.54(10) . . ?
C11 C10 C12 46.83(12) . . ?
C9 C10 H10A 114.1 . . ?
C11 C10 H10A 114.1 . . ?
C12 C10 H10A 125.0 . . ?
C9 C10 H10B 114.1 . . ?
C11 C10 H10B 114.1 . . ?
C12 C10 H10B 123.6 . . ?
H10A C10 H10B 111.3 . . ?
C12 C11 C10 84.27(15) . . ?
C12 C11 H11A 114.6 . . ?
C10 C11 H11A 114.6 . . ?
C12 C11 H11B 114.6 . . ?
C10 C11 H11B 114.6 . . ?
H11A C11 H11B 111.7 . . ?
C9 C12 C11 96.88(18) . . ?
C9 C12 Cl1 134.56(16) . . ?
C11 C12 Cl1 128.55(16) . . ?
C9 C12 C10 47.99(12) . . ?
C11 C12 C10 48.91(12) . . ?
Cl1 C12 C10 177.45(13) . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 119.7(2) . . ?
C15 C14 S2 120.44(17) . . ?
C19 C14 S2 119.89(15) . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 122.1(3) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C18 C17 C16 117.6(2) . . ?
C18 C17 C20 121.4(3) . . ?
C16 C17 C20 121.0(3) . . ?
C17 C18 C19 121.8(2) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C14 119.5(2) . . ?
C18 C19 H19 120.3 . . ?
C14 C19 H19 120.3 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 S1 C4 91.54(12) . . ?
C4 C3 C2 116.2(6) . . ?
C4 C3 H3 121.9 . . ?
C2 C3 H3 121.9 . . ?
C2 S1' C4 93.4(3) . . ?
C4 C3' C1 115.3(6) . . ?
C4 C3' H3' 122.4 . . ?
C1 C3' H3' 122.4 . . ?

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
O2 S2 N1 C6 173.64(16) . . . . ?
O3 S2 N1 C6 44.14(18) . . . . ?
C14 S2 N1 C6 -70.10(17) . . . . ?
O2 S2 N1 C7 -36.28(18) . . . . ?
O3 S2 N1 C7 -165.78(15) . . . . ?
C14 S2 N1 C7 79.98(16) . . . . ?
C3' C1 C2 C3 -0.2(9) . . . . ?
S1 C1 C2 C3 -0.8(7) . . . . ?
C3' C1 C2 S1' -0.2(8) . . . . ?
S1 C1 C2 S1' -0.9(5) . . . . ?
C3 C4 C5 O1 -149.8(9) . . . . ?
C3' C4 C5 O1 30.3(9) . . . . ?
S1' C4 C5 O1 -149.8(4) . . . . ?
S1 C4 C5 O1 29.7(2) . . . . ?
C3 C4 C5 C6 -26.1(9) . . . . ?
C3' C4 C5 C6 154.0(8) . . . . ?
S1' C4 C5 C6 -26.1(4) . . . . ?
S1 C4 C5 C6 153.36(15) . . . . ?
C3 C4 C5 C8 91.6(9) . . . . ?
C3' C4 C5 C8 -88.3(8) . . . . ?
S1' C4 C5 C8 91.6(4) . . . . ?
S1 C4 C5 C8 -88.91(18) . . . . ?
C7 N1 C6 C5 -4.0(2) . . . . ?
S2 N1 C6 C5 148.91(13) . . . . ?
O1 C5 C6 N1 -80.44(17) . . . . ?
C4 C5 C6 N1 155.69(15) . . . . ?
C8 C5 C6 N1 30.19(17) . . . . ?
C6 N1 C7 C8 -24.51(19) . . . . ?
S2 N1 C7 C8 -177.43(12) . . . . ?
N1 C7 C8 C9 161.56(14) . . . . ?
N1 C7 C8 C13 -75.51(17) . . . . ?
N1 C7 C8 C5 41.63(16) . . . . ?
O1 C5 C8 C9 -47.94(19) . . . . ?
C4 C5 C8 C9 73.66(19) . . . . ?
C6 C5 C8 C9 -162.42(15) . . . . ?
O1 C5 C8 C7 69.82(16) . . . . ?
C4 C5 C8 C7 -168.58(15) . . . . ?
C6 C5 C8 C7 -44.66(16) . . . . ?
O1 C5 C8 C13 -173.43(14) . . . . ?
C4 C5 C8 C13 -51.8(2) . . . . ?
C6 C5 C8 C13 72.09(18) . . . . ?
C7 C8 C9 C12 155.8(2) . . . . ?
C13 C8 C9 C12 32.9(3) . . . . ?
C5 C8 C9 C12 -92.8(2) . . . . ?
C7 C8 C9 C10 -18.0(3) . . . . ?
C13 C8 C9 C10 -140.9(2) . . . . ?
C5 C8 C9 C10 93.3(2) . . . . ?
C12 C9 C10 C11 -1.01(16) . . . . ?
C8 C9 C10 C11 174.77(18) . . . . ?
C8 C9 C10 C12 175.8(3) . . . . ?
C9 C10 C11 C12 0.90(15) . . . . ?
C8 C9 C12 C11 -174.4(2) . . . . ?
C10 C9 C12 C11 1.05(17) . . . . ?
C8 C9 C12 Cl1 4.4(4) . . . . ?
C10 C9 C12 Cl1 179.78(19) . . . . ?
C8 C9 C12 C10 -175.4(3) . . . . ?
C10 C11 C12 C9 -1.04(17) . . . . ?
C10 C11 C12 Cl1 -179.88(17) . . . . ?
O2 S2 C14 C15 16.5(2) . . . . ?
O3 S2 C14 C15 146.82(19) . . . . ?
N1 S2 C14 C15 -98.8(2) . . . . ?
O2 S2 C14 C19 -162.89(16) . . . . ?
O3 S2 C14 C19 -32.60(19) . . . . ?
N1 S2 C14 C19 81.75(18) . . . . ?
C19 C14 C15 C16 1.3(4) . . . . ?
S2 C14 C15 C16 -178.1(2) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C15 C16 C17 C18 -0.7(5) . . . . ?
C15 C16 C17 C20 178.3(3) . . . . ?
C16 C17 C18 C19 1.8(4) . . . . ?
C20 C17 C18 C19 -177.1(3) . . . . ?
C17 C18 C19 C14 -1.4(4) . . . . ?
C15 C14 C19 C18 -0.3(3) . . . . ?
S2 C14 C19 C18 179.16(17) . . . . ?
C2 C1 S1 C4 1.1(2) . . . . ?
C3' C1 S1 C4 -2(3) . . . . ?
C3 C4 S1 C1 -1.0(7) . . . . ?
C3' C4 S1 C1 2(4) . . . . ?
C5 C4 S1 C1 179.44(16) . . . . ?
S1' C4 S1 C1 -1.0(4) . . . . ?
C3' C4 C3 C2 0.1(13) . . . . ?
C5 C4 C3 C2 -179.8(5) . . . . ?
S1' C4 C3 C2 -180(100) . . . . ?
S1 C4 C3 C2 0.7(13) . . . . ?
C1 C2 C3 C4 0.0(13) . . . . ?
S1' C2 C3 C4 180(5) . . . . ?
C1 C2 S1' C4 0.1(6) . . . . ?
C3 C2 S1' C4 0(3) . . . . ?
C3 C4 S1' C2 0(6) . . . . ?
C3' C4 S1' C2 0.1(8) . . . . ?
C5 C4 S1' C2 -179.8(2) . . . . ?
S1 C4 S1' C2 0.7(5) . . . . ?
C3 C4 C3' C1 -0.3(13) . . . . ?
C5 C4 C3' C1 179.7(5) . . . . ?
S1' C4 C3' C1 -0.2(12) . . . . ?
S1 C4 C3' C1 -177(5) . . . . ?
C2 C1 C3' C4 0.3(12) . . . . ?
S1 C1 C3' C4 178(4) . . . . ?

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-4

