# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_230316e
_database_code_depnum_ccdc_archive 'CCDC 2368219'
loop_
_audit_author_name
_audit_author_address
'Yi-Long Zhu'
;Nanjing Tech University
China
;
_audit_update_record             
;
2024-07-05 deposited with the CCDC.	2024-11-04 downloaded from the CCDC.
;
_audit_creation_date             2024-07-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        3a
_chemical_formula_moiety         'C20 H21 N O3 S'
_chemical_formula_sum            'C20 H21 N O3 S'
_chemical_formula_weight         355.44
_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 0.0033 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'

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

_cell_length_a                   9.8268(8)
_cell_length_b                   10.2332(9)
_cell_length_c                   10.4943(9)
_cell_angle_alpha                117.108(6)
_cell_angle_beta                 97.444(2)
_cell_angle_gamma                101.149(3)
_cell_volume                     892.56(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    978
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.872
_cell_measurement_theta_min      2.182
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.9764
_exptl_absorpt_correction_T_min  0.9297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_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    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0981
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4313
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.016
_diffrn_reflns_theta_max         25.016
_diffrn_reflns_theta_min         2.181
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1857
_reflns_number_total             3067
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3067
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0767
_refine_ls_restrained_S_all      1.060
_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)+(0.0732P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1651
_refine_ls_wR_factor_ref         0.1805
_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:
 C1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C18(H18),
 C19(H19)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C20(H20A,H20B,
 H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.99497(10) 0.31183(13) 0.25682(12) 0.0399(3) Uani 1 1 d . . . . .
N1 N 0.4630(3) 0.1786(4) 0.0999(4) 0.0482(9) Uani 1 1 d . . . . .
O1 O 0.3768(4) 0.1024(4) -0.1405(4) 0.0813(12) Uani 1 1 d . . . . .
O2 O 0.9855(3) 0.2409(3) 0.1013(3) 0.0507(8) Uani 1 1 d . . . . .
O3 O 1.0855(3) 0.4668(3) 0.3496(3) 0.0535(9) Uani 1 1 d . . . . .
C1 C 0.8219(4) 0.3013(5) 0.2869(5) 0.0407(10) Uani 1 1 d . . . . .
H1 H 0.805198 0.280242 0.361737 0.049 Uiso 1 1 calc R U . . .
C2 C 0.7119(4) 0.3201(4) 0.2146(4) 0.0374(10) Uani 1 1 d . . . . .
C3 C 0.5653(4) 0.2933(5) 0.2443(5) 0.0435(11) Uani 1 1 d . . . . .
C4 C 0.4712(5) 0.1837(5) -0.0252(6) 0.0526(12) Uani 1 1 d . . . . .
C5 C 0.5997(5) 0.2906(5) -0.0209(5) 0.0488(11) Uani 1 1 d . . . . .
C6 C 0.7177(4) 0.3635(5) 0.0992(5) 0.0406(10) Uani 1 1 d . . . . .
C7 C 0.8295(5) 0.4737(5) 0.1057(5) 0.0531(12) Uani 1 1 d . . . . .
H7 H 0.907684 0.526072 0.187482 0.064 Uiso 1 1 calc R U . . .
C8 C 0.8258(5) 0.5061(7) -0.0066(6) 0.0701(16) Uani 1 1 d . . . . .
H8 H 0.899972 0.582998 0.000619 0.084 Uiso 1 1 calc R U . . .
C9 C 0.7129(6) 0.4259(8) -0.1314(7) 0.0806(18) Uani 1 1 d . . . . .
H9 H 0.713722 0.443512 -0.210761 0.097 Uiso 1 1 calc R U . . .
C10 C 0.5998(6) 0.3200(7) -0.1364(6) 0.0702(15) Uani 1 1 d . . . . .
H10 H 0.522187 0.267530 -0.218827 0.084 Uiso 1 1 calc R U . . .
C11 C 0.5592(5) 0.2366(6) 0.3553(5) 0.0574(13) Uani 1 1 d . . . . .
H11A H 0.466539 0.228898 0.375882 0.086 Uiso 1 1 calc R U . . .
H11B H 0.631398 0.307463 0.445076 0.086 Uiso 1 1 calc R U . . .
H11C H 0.575970 0.137777 0.314910 0.086 Uiso 1 1 calc R U . . .
C12 C 0.5230(5) 0.4435(5) 0.3050(5) 0.0577(13) Uani 1 1 d . . . . .
H12A H 0.525671 0.480793 0.236148 0.087 Uiso 1 1 calc R U . . .
H12B H 0.588880 0.518371 0.397997 0.087 Uiso 1 1 calc R U . . .
H12C H 0.427868 0.425051 0.318849 0.087 Uiso 1 1 calc R U . . .
C13 C 0.3288(5) 0.0910(6) 0.1004(6) 0.0746(16) Uani 1 1 d . . . . .
H13A H 0.275962 0.159372 0.152200 0.112 Uiso 1 1 calc R U . . .
H13B H 0.347479 0.033933 0.148909 0.112 Uiso 1 1 calc R U . . .
H13C H 0.273911 0.021592 0.000512 0.112 Uiso 1 1 calc R U . . .
C14 C 1.0513(4) 0.1970(5) 0.3233(4) 0.0352(9) Uani 1 1 d . . . . .
C15 C 1.0296(4) 0.0435(5) 0.2278(5) 0.0449(11) Uani 1 1 d . . . . .
H15 H 0.978451 -0.001148 0.130001 0.054 Uiso 1 1 calc R U . . .
C16 C 1.0843(5) -0.0438(5) 0.2785(5) 0.0537(12) Uani 1 1 d . . . . .
H16 H 1.071420 -0.146795 0.213048 0.064 Uiso 1 1 calc R U . . .
C17 C 1.1572(4) 0.0183(6) 0.4231(5) 0.0483(11) Uani 1 1 d . . . . .
C18 C 1.1746(5) 0.1701(6) 0.5158(5) 0.0584(13) Uani 1 1 d . . . . .
H18 H 1.223365 0.214033 0.614320 0.070 Uiso 1 1 calc R U . . .
C19 C 1.1222(4) 0.2607(5) 0.4684(5) 0.0504(12) Uani 1 1 d . . . . .
H19 H 1.134874 0.363538 0.534181 0.060 Uiso 1 1 calc R U . . .
C20 C 1.2191(6) -0.0752(6) 0.4772(6) 0.0752(16) Uani 1 1 d . . . . .
H20A H 1.313866 -0.071578 0.462566 0.113 Uiso 1 1 calc R U . . .
H20B H 1.159776 -0.179378 0.423294 0.113 Uiso 1 1 calc R U . . .
H20C H 1.223325 -0.034490 0.580596 0.113 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 O2 1.434(3) . ?
S1 O3 1.441(3) . ?
S1 C1 1.762(4) . ?
S1 C14 1.753(4) . ?
N1 C3 1.488(5) . ?
N1 C4 1.350(5) . ?
N1 C13 1.446(5) . ?
O1 C4 1.228(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.334(5) . ?
C2 C3 1.513(5) . ?
C2 C6 1.471(5) . ?
C3 C11 1.522(5) . ?
C3 C12 1.538(6) . ?
C4 C5 1.483(6) . ?
C5 C6 1.386(5) . ?
C5 C10 1.376(6) . ?
C6 C7 1.384(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.360(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(7) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.377(5) . ?
C14 C19 1.369(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(6) . ?
C17 C18 1.366(6) . ?
C17 C20 1.496(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(6) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 117.96(18) . . ?
O2 S1 C1 109.68(18) . . ?
O2 S1 C14 108.54(19) . . ?
O3 S1 C1 109.3(2) . . ?
O3 S1 C14 108.29(17) . . ?
C14 S1 C1 101.89(18) . . ?
C4 N1 C3 121.7(4) . . ?
C4 N1 C13 117.2(4) . . ?
C13 N1 C3 118.4(4) . . ?
S1 C1 H1 116.2 . . ?
C2 C1 S1 127.5(3) . . ?
C2 C1 H1 116.2 . . ?
C1 C2 C3 121.1(4) . . ?
C1 C2 C6 125.1(4) . . ?
C6 C2 C3 113.8(3) . . ?
N1 C3 C2 106.8(3) . . ?
N1 C3 C11 110.3(4) . . ?
N1 C3 C12 109.0(3) . . ?
C2 C3 C11 112.8(3) . . ?
C2 C3 C12 109.6(3) . . ?
C11 C3 C12 108.3(4) . . ?
N1 C4 C5 117.9(4) . . ?
O1 C4 N1 122.0(4) . . ?
O1 C4 C5 120.1(5) . . ?
C6 C5 C4 120.8(4) . . ?
C10 C5 C4 119.3(4) . . ?
C10 C5 C6 119.9(4) . . ?
C5 C6 C2 116.5(4) . . ?
C7 C6 C2 124.5(4) . . ?
C7 C6 C5 119.0(4) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.5(4) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.6(5) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.1(5) . . ?
C10 C9 H9 120.5 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.7(5) . . ?
C9 C10 H10 119.6 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 S1 119.9(3) . . ?
C19 C14 S1 120.2(3) . . ?
C19 C14 C15 119.9(4) . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.5(4) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.5(4) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C20 121.5(5) . . ?
C18 C17 C16 117.6(4) . . ?
C18 C17 C20 120.8(4) . . ?
C17 C18 H18 118.9 . . ?
C17 C18 C19 122.3(4) . . ?
C19 C18 H18 118.9 . . ?
C14 C19 C18 119.2(4) . . ?
C14 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 174.4(3) . . . . ?
S1 C1 C2 C6 -4.0(7) . . . . ?
S1 C14 C15 C16 174.9(3) . . . . ?
S1 C14 C19 C18 -175.4(3) . . . . ?
N1 C4 C5 C6 10.6(6) . . . . ?
N1 C4 C5 C10 -167.9(4) . . . . ?
O1 C4 C5 C6 -168.9(4) . . . . ?
O1 C4 C5 C10 12.6(7) . . . . ?
O2 S1 C1 C2 -39.8(4) . . . . ?
O2 S1 C14 C15 -23.2(4) . . . . ?
O2 S1 C14 C19 154.1(3) . . . . ?
O3 S1 C1 C2 90.9(4) . . . . ?
O3 S1 C14 C15 -152.3(3) . . . . ?
O3 S1 C14 C19 24.9(4) . . . . ?
C1 S1 C14 C15 92.5(3) . . . . ?
C1 S1 C14 C19 -90.2(4) . . . . ?
C1 C2 C3 N1 -124.5(4) . . . . ?
C1 C2 C3 C11 -3.0(6) . . . . ?
C1 C2 C3 C12 117.6(4) . . . . ?
C1 C2 C6 C5 140.3(4) . . . . ?
C1 C2 C6 C7 -41.9(7) . . . . ?
C2 C6 C7 C8 179.9(4) . . . . ?
C3 N1 C4 O1 -170.3(4) . . . . ?
C3 N1 C4 C5 10.3(6) . . . . ?
C3 C2 C6 C5 -38.2(5) . . . . ?
C3 C2 C6 C7 139.6(4) . . . . ?
C4 N1 C3 C2 -41.2(5) . . . . ?
C4 N1 C3 C11 -164.1(4) . . . . ?
C4 N1 C3 C12 77.1(5) . . . . ?
C4 C5 C6 C2 4.4(6) . . . . ?
C4 C5 C6 C7 -173.6(4) . . . . ?
C4 C5 C10 C9 175.6(5) . . . . ?
C5 C6 C7 C8 -2.3(7) . . . . ?
C6 C2 C3 N1 54.1(4) . . . . ?
C6 C2 C3 C11 175.5(4) . . . . ?
C6 C2 C3 C12 -63.8(5) . . . . ?
C6 C5 C10 C9 -2.8(8) . . . . ?
C6 C7 C8 C9 -2.3(8) . . . . ?
C7 C8 C9 C10 4.3(8) . . . . ?
C8 C9 C10 C5 -1.7(8) . . . . ?
C10 C5 C6 C2 -177.1(4) . . . . ?
C10 C5 C6 C7 4.9(7) . . . . ?
C13 N1 C3 C2 158.0(4) . . . . ?
C13 N1 C3 C11 35.1(5) . . . . ?
C13 N1 C3 C12 -83.7(5) . . . . ?
C13 N1 C4 O1 -9.3(7) . . . . ?
C13 N1 C4 C5 171.3(4) . . . . ?
C14 S1 C1 C2 -154.7(4) . . . . ?
C14 C15 C16 C17 1.6(7) . . . . ?
C15 C14 C19 C18 1.8(6) . . . . ?
C15 C16 C17 C18 -0.3(7) . . . . ?
C15 C16 C17 C20 -178.7(4) . . . . ?
C16 C17 C18 C19 -0.3(7) . . . . ?
C17 C18 C19 C14 -0.5(7) . . . . ?
C19 C14 C15 C16 -2.4(6) . . . . ?
C20 C17 C18 C19 178.2(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
