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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2324611'
loop_
_audit_author_name
_audit_author_address
'Yuxi Wu '
;Wuhan Institute of Technology
China
;
_audit_update_record             
;
2024-01-10 deposited with the CCDC.	2025-09-30 downloaded from the CCDC.
;
_audit_creation_date             2024-01-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N O2 S'
_chemical_formula_sum            'C19 H21 N O2 S'
_chemical_formula_weight         327.43
_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      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                   18.752(4)
_cell_length_b                   11.319(2)
_cell_length_c                   8.2409(19)
_cell_angle_alpha                90
_cell_angle_beta                 95.542(6)
_cell_angle_gamma                90
_cell_volume                     1741.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4113
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.52
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5778
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0875 before and 0.0744 after correction.
The Ratio of minimum to maximum transmission is 0.7754.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1112
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            25738
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.198
_diffrn_reflns_theta_min         2.829
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1682
_reflns_number_total             3085
_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 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3085
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1461
_refine_ls_R_factor_gt           0.0709
_refine_ls_restrained_S_all      1.020
_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)+(0.0411P)²+2.2253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1625
_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:
 C17(H17), C16(H16), C15(H15), C10(H10), C14(H14), C4(H4), C2(H2), C5(H5),
 C1(H1)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
;
_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 0.80223(7) 0.36696(10) 0.90384(14) 0.0684(4) Uani 1 1 d . . . . .
O2 O 0.38181(15) 0.3622(3) 0.5432(3) 0.0661(8) Uani 1 1 d . . . . .
O1 O 0.66117(17) 0.4382(3) 1.0004(3) 0.0842(10) Uani 1 1 d . . . . .
N1 N 0.77507(18) 0.4351(3) 0.5091(4) 0.0604(9) Uani 1 1 d . . . . .
C13 C 0.5889(2) 0.4030(3) 0.7589(4) 0.0480(10) Uani 1 1 d . . . . .
C18 C 0.4514(2) 0.3715(4) 0.6065(5) 0.0522(10) Uani 1 1 d . . . . .
C17 C 0.5060(2) 0.2996(3) 0.5678(4) 0.0524(10) Uani 1 1 d . . . . .
H17 H 0.4968 0.2397 0.4913 0.063 Uiso 1 1 calc R U . . .
C16 C 0.5743(2) 0.3153(3) 0.6412(4) 0.0533(10) Uani 1 1 d . . . . .
H16 H 0.6112 0.2671 0.6122 0.064 Uiso 1 1 calc R U . . .
C15 C 0.5324(3) 0.4720(4) 0.7963(5) 0.0564(11) Uani 1 1 d . . . . .
H15 H 0.5410 0.5307 0.8747 0.068 Uiso 1 1 calc R U . . .
C10 C 0.7247(2) 0.4272(3) 0.6113(4) 0.0528(10) Uani 1 1 d . . . . .
H10 H 0.6786 0.4374 0.5608 0.063 Uiso 1 1 calc R U . . .
C12 C 0.6601(2) 0.4167(4) 0.8519(5) 0.0568(11) Uani 1 1 d . . . . .
C14 C 0.4649(2) 0.4586(4) 0.7246(5) 0.0569(11) Uani 1 1 d . . . . .
H14 H 0.4280 0.5069 0.7539 0.068 Uiso 1 1 calc R U . . .
C11 C 0.7265(2) 0.4070(3) 0.7761(4) 0.0514(10) Uani 1 1 d . . . . .
C3 C 0.8429(2) 0.4981(4) 0.9774(4) 0.0533(10) Uani 1 1 d . . . . .
C4 C 0.8163(2) 0.6095(4) 0.9482(5) 0.0700(13) Uani 1 1 d . . . . .
H4 H 0.7726 0.6197 0.8863 0.084 Uiso 1 1 calc R U . . .
C2 C 0.9064(2) 0.4873(5) 1.0737(6) 0.0753(14) Uani 1 1 d . . . . .
H2 H 0.9248 0.4124 1.0986 0.090 Uiso 1 1 calc R U . . .
C19 C 0.3638(2) 0.2781(4) 0.4178(6) 0.0799(14) Uani 1 1 d . . . . .
H19A H 0.3917 0.2930 0.3281 0.120 Uiso 1 1 calc R U . . .
H19B H 0.3138 0.2845 0.3813 0.120 Uiso 1 1 calc R U . . .
H19C H 0.3739 0.2000 0.4593 0.120 Uiso 1 1 calc R U . . .
C5 C 0.9431(3) 0.5841(6) 1.1334(6) 0.0836(15) Uani 1 1 d . . . . .
H5 H 0.9860 0.5735 1.1982 0.100 Uiso 1 1 calc R U . . .
C6 C 0.9194(3) 0.6946(5) 1.1019(6) 0.0773(14) Uani 1 1 d . . . . .
C9 C 0.7529(3) 0.4532(5) 0.3350(5) 0.0864(16) Uani 1 1 d . . . . .
H9A H 0.7679 0.3870 0.2739 0.130 Uiso 1 1 calc R U . . .
H9B H 0.7746 0.5240 0.2986 0.130 Uiso 1 1 calc R U . . .
H9C H 0.7017 0.4604 0.3188 0.130 Uiso 1 1 calc R U . . .
C8 C 0.8511(2) 0.4238(5) 0.5494(6) 0.0833(15) Uani 1 1 d . . . . .
H8A H 0.8657 0.4729 0.6416 0.125 Uiso 1 1 calc R U . . .
H8B H 0.8756 0.4481 0.4580 0.125 Uiso 1 1 calc R U . . .
H8C H 0.8626 0.3430 0.5755 0.125 Uiso 1 1 calc R U . . .
C1 C 0.8542(3) 0.7072(5) 1.0102(7) 0.0897(16) Uani 1 1 d . . . . .
H1 H 0.8354 0.7824 0.9899 0.108 Uiso 1 1 calc R U . . .
C7 C 0.9636(3) 0.8014(5) 1.1595(8) 0.122(2) Uani 1 1 d . . . . .
H7A H 1.0092 0.7758 1.2104 0.183 Uiso 1 1 calc R U . . .
H7B H 0.9389 0.8451 1.2366 0.183 Uiso 1 1 calc R U . . .
H7C H 0.9708 0.8509 1.0679 0.183 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 C11 1.743(4) . ?
S1 C3 1.750(4) . ?
O2 C18 1.362(5) . ?
O2 C19 1.422(5) . ?
O1 C12 1.246(4) . ?
N1 C10 1.327(5) . ?
N1 C9 1.469(5) . ?
N1 C8 1.437(5) . ?
C13 C16 1.396(5) . ?
C13 C15 1.375(5) . ?
C13 C12 1.483(5) . ?
C18 C17 1.370(5) . ?
C18 C14 1.391(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.374(5) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.353(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(5) . ?
C12 C11 1.451(5) . ?
C14 H14 0.9300 . ?
C3 C4 1.369(6) . ?
C3 C2 1.372(5) . ?
C4 H4 0.9300 . ?
C4 C1 1.384(6) . ?
C2 H2 0.9300 . ?
C2 C5 1.360(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C6 1.344(7) . ?
C6 C1 1.381(6) . ?
C6 C7 1.517(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C1 H1 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
C11 S1 C3 106.88(19) . . ?
C18 O2 C19 118.8(3) . . ?
C10 N1 C9 118.5(3) . . ?
C10 N1 C8 126.7(4) . . ?
C8 N1 C9 114.8(3) . . ?
C16 C13 C12 122.7(4) . . ?
C15 C13 C16 117.1(4) . . ?
C15 C13 C12 120.0(4) . . ?
O2 C18 C17 125.1(4) . . ?
O2 C18 C14 115.2(4) . . ?
C17 C18 C14 119.7(4) . . ?
C18 C17 H17 119.8 . . ?
C18 C17 C16 120.4(4) . . ?
C16 C17 H17 119.8 . . ?
C13 C16 H16 119.7 . . ?
C17 C16 C13 120.7(4) . . ?
C17 C16 H16 119.7 . . ?
C13 C15 H15 118.4 . . ?
C14 C15 C13 123.2(4) . . ?
C14 C15 H15 118.4 . . ?
N1 C10 H10 113.3 . . ?
N1 C10 C11 133.4(4) . . ?
C11 C10 H10 113.3 . . ?
O1 C12 C13 117.2(4) . . ?
O1 C12 C11 120.3(4) . . ?
C11 C12 C13 122.5(3) . . ?
C18 C14 H14 120.5 . . ?
C15 C14 C18 118.9(4) . . ?
C15 C14 H14 120.5 . . ?
C10 C11 S1 125.5(3) . . ?
C10 C11 C12 118.2(4) . . ?
C12 C11 S1 116.2(3) . . ?
C4 C3 S1 125.6(3) . . ?
C4 C3 C2 117.7(4) . . ?
C2 C3 S1 116.7(4) . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C1 120.4(4) . . ?
C1 C4 H4 119.8 . . ?
C3 C2 H2 119.4 . . ?
C5 C2 C3 121.2(5) . . ?
C5 C2 H2 119.4 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 C5 H5 118.9 . . ?
C6 C5 C2 122.3(5) . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 117.4(5) . . ?
C5 C6 C7 121.4(5) . . ?
C1 C6 C7 121.2(5) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C1 H1 119.5 . . ?
C6 C1 C4 121.0(5) . . ?
C6 C1 H1 119.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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 C3 C4 C1 -178.6(4) . . . . ?
S1 C3 C2 C5 178.3(4) . . . . ?
O2 C18 C17 C16 -178.8(3) . . . . ?
O2 C18 C14 C15 178.6(3) . . . . ?
O1 C12 C11 S1 25.2(5) . . . . ?
O1 C12 C11 C10 -156.2(4) . . . . ?
N1 C10 C11 S1 -8.1(7) . . . . ?
N1 C10 C11 C12 173.5(4) . . . . ?
C13 C15 C14 C18 -0.4(6) . . . . ?
C13 C12 C11 S1 -155.4(3) . . . . ?
C13 C12 C11 C10 23.2(6) . . . . ?
C18 C17 C16 C13 1.5(6) . . . . ?
C17 C18 C14 C15 1.5(6) . . . . ?
C16 C13 C15 C14 -0.2(6) . . . . ?
C16 C13 C12 O1 -138.2(4) . . . . ?
C16 C13 C12 C11 42.3(6) . . . . ?
C15 C13 C16 C17 -0.4(5) . . . . ?
C15 C13 C12 O1 36.5(5) . . . . ?
C15 C13 C12 C11 -142.9(4) . . . . ?
C12 C13 C16 C17 174.5(3) . . . . ?
C12 C13 C15 C14 -175.2(4) . . . . ?
C14 C18 C17 C16 -2.0(6) . . . . ?
C11 S1 C3 C4 4.4(4) . . . . ?
C11 S1 C3 C2 -176.2(3) . . . . ?
C3 S1 C11 C10 90.1(4) . . . . ?
C3 S1 C11 C12 -91.5(3) . . . . ?
C3 C4 C1 C6 0.3(8) . . . . ?
C3 C2 C5 C6 0.0(8) . . . . ?
C4 C3 C2 C5 -2.3(7) . . . . ?
C2 C3 C4 C1 2.0(7) . . . . ?
C2 C5 C6 C1 2.3(8) . . . . ?
C2 C5 C6 C7 -175.6(5) . . . . ?
C19 O2 C18 C17 -5.2(6) . . . . ?
C19 O2 C18 C14 177.9(4) . . . . ?
C5 C6 C1 C4 -2.5(8) . . . . ?
C9 N1 C10 C11 177.6(5) . . . . ?
C8 N1 C10 C11 -0.2(8) . . . . ?
C7 C6 C1 C4 175.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
