# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 
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data_230729xl_0m
_database_code_depnum_ccdc_archive 'CCDC 2292991'
loop_
_audit_author_name
_audit_author_address
'Lei Xie'
;Liaocheng University
China
;
_audit_update_record             
;
2023-09-05 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_audit_creation_date             2023-07-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 N2 O3 S'
_chemical_formula_sum            'C19 H18 N2 O3 S'
_chemical_formula_weight         354.41
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   32.264(3)
_cell_length_b                   6.0091(5)
_cell_length_c                   19.0987(17)
_cell_angle_alpha                90
_cell_angle_beta                 110.3890(10)
_cell_angle_gamma                90
_cell_volume                     3470.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5324
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.364
_cell_measurement_theta_min      2.694
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1022 before and 0.0293 after correction.
The Ratio of minimum to maximum transmission is 0.9179.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_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  0.0153
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9891
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.364
_diffrn_reflns_theta_min         2.857
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_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                3377
_reflns_number_total             3885
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3885
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+2.1809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0876
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C13(H13), C15(H15),
 C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_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 0.72984(2) -0.04588(6) 0.66799(2) 0.03336(10) Uani 1 1 d . . . . .
O1 O 0.67792(3) 0.36125(15) 0.49842(4) 0.0324(2) Uani 1 1 d . . . . .
O2 O 0.65203(4) -0.1443(2) 0.67361(7) 0.0642(4) Uani 1 1 d . . . . .
O3 O 0.75908(3) 0.50400(17) 0.54093(6) 0.0419(2) Uani 1 1 d . . . . .
N1 N 0.70897(3) 0.28232(19) 0.56483(5) 0.0304(2) Uani 1 1 d . . . . .
N2 N 0.65034(3) 0.14421(19) 0.59226(6) 0.0338(2) Uani 1 1 d . . . . .
C1 C 0.69250(4) 0.1355(2) 0.60524(6) 0.0286(3) Uani 1 1 d . . . . .
C2 C 0.56530(5) 0.5243(3) 0.32329(9) 0.0509(4) Uani 1 1 d . . . . .
H2 H 0.544668 0.418674 0.297055 0.061 Uiso 1 1 calc R U . . .
C3 C 0.81798(5) -0.0893(3) 0.71846(8) 0.0421(3) Uani 1 1 d . . . . .
H3A H 0.818128 -0.021800 0.764093 0.063 Uiso 1 1 calc R U . . .
H3B H 0.846033 -0.065175 0.712703 0.063 Uiso 1 1 calc R U . . .
H3C H 0.812800 -0.246286 0.719998 0.063 Uiso 1 1 calc R U . . .
C4 C 0.58338(4) 0.0308(2) 0.61365(7) 0.0366(3) Uani 1 1 d . . . . .
C5 C 0.56657(5) 0.7285(3) 0.29142(9) 0.0492(4) Uani 1 1 d . . . . .
H5 H 0.546755 0.760939 0.243943 0.059 Uiso 1 1 calc R U . . .
C6 C 0.75208(4) 0.3625(2) 0.58015(7) 0.0309(3) Uani 1 1 d . . . . .
C7 C 0.59720(5) 0.8842(3) 0.32995(9) 0.0477(4) Uani 1 1 d . . . . .
H7 H 0.597942 1.022569 0.308607 0.057 Uiso 1 1 calc R U . . .
C8 C 0.62597(4) 0.6306(2) 0.43300(7) 0.0317(3) Uani 1 1 d . . . . .
C9 C 0.49402(5) 0.0811(4) 0.59084(10) 0.0608(5) Uani 1 1 d . . . . .
H9 H 0.464107 0.097827 0.583207 0.073 Uiso 1 1 calc R U . . .
C10 C 0.62705(5) 0.8359(2) 0.40061(8) 0.0391(3) Uani 1 1 d . . . . .
H10 H 0.647830 0.941662 0.426297 0.047 Uiso 1 1 calc R U . . .
C11 C 0.56128(5) 0.2236(3) 0.58180(9) 0.0473(4) Uani 1 1 d . . . . .
H11 H 0.576337 0.336580 0.567446 0.057 Uiso 1 1 calc R U . . .
C12 C 0.78140(4) 0.0143(2) 0.65262(7) 0.0322(3) Uani 1 1 d . . . . .
H12 H 0.780922 -0.056908 0.606184 0.039 Uiso 1 1 calc R U . . .
C13 C 0.59454(5) 0.4751(3) 0.39420(8) 0.0432(3) Uani 1 1 d . . . . .
H13 H 0.593112 0.337879 0.415778 0.052 Uiso 1 1 calc R U . . .
C14 C 0.63169(5) -0.0013(2) 0.62966(7) 0.0370(3) Uani 1 1 d . . . . .
C15 C 0.51670(6) 0.2488(4) 0.57121(10) 0.0590(5) Uani 1 1 d . . . . .
H15 H 0.502172 0.379843 0.550739 0.071 Uiso 1 1 calc R U . . .
C16 C 0.78687(4) 0.2629(2) 0.64691(7) 0.0349(3) Uani 1 1 d . . . . .
H16A H 0.785584 0.333605 0.691771 0.042 Uiso 1 1 calc R U . . .
H16B H 0.815765 0.293037 0.644023 0.042 Uiso 1 1 calc R U . . .
C17 C 0.51551(6) -0.1109(4) 0.62168(10) 0.0612(5) Uani 1 1 d . . . . .
H17 H 0.499971 -0.224944 0.634377 0.073 Uiso 1 1 calc R U . . .
C18 C 0.56023(5) -0.1369(3) 0.63419(9) 0.0486(4) Uani 1 1 d . . . . .
H18 H 0.574712 -0.266391 0.656294 0.058 Uiso 1 1 calc R U . . .
C19 C 0.65923(5) 0.5748(2) 0.50829(7) 0.0383(3) Uani 1 1 d . . . . .
H19A H 0.682065 0.687914 0.524107 0.046 Uiso 1 1 calc R U . . .
H19B H 0.645058 0.563399 0.545370 0.046 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 C1 1.7524(13) . ?
S1 C12 1.8234(13) . ?
O1 N1 1.3970(12) . ?
O1 C19 1.4579(16) . ?
O2 C14 1.2203(17) . ?
O3 C6 1.2055(15) . ?
N1 C1 1.3935(16) . ?
N1 C6 1.4033(16) . ?
N2 C1 1.2960(16) . ?
N2 C14 1.3914(17) . ?
C2 H2 0.9300 . ?
C2 C5 1.377(2) . ?
C2 C13 1.386(2) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3 C12 1.5256(18) . ?
C4 C11 1.385(2) . ?
C4 C14 1.4928(19) . ?
C4 C18 1.390(2) . ?
C5 H5 0.9300 . ?
C5 C7 1.373(2) . ?
C6 C16 1.4987(18) . ?
C7 H7 0.9300 . ?
C7 C10 1.388(2) . ?
C8 C10 1.3858(19) . ?
C8 C13 1.388(2) . ?
C8 C19 1.5022(18) . ?
C9 H9 0.9300 . ?
C9 C15 1.372(3) . ?
C9 C17 1.369(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C15 1.389(2) . ?
C12 H12 0.9800 . ?
C12 C16 1.513(2) . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17 0.9300 . ?
C17 C18 1.387(2) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 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
C1 S1 C12 102.42(6) . . ?
N1 O1 C19 112.31(9) . . ?
O1 N1 C6 114.71(9) . . ?
C1 N1 O1 115.24(10) . . ?
C1 N1 C6 130.04(10) . . ?
C1 N2 C14 119.29(11) . . ?
N1 C1 S1 117.94(9) . . ?
N2 C1 S1 125.56(10) . . ?
N2 C1 N1 116.49(11) . . ?
C5 C2 H2 119.8 . . ?
C5 C2 C13 120.49(15) . . ?
C13 C2 H2 119.8 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C12 C3 H3A 109.5 . . ?
C12 C3 H3B 109.5 . . ?
C12 C3 H3C 109.5 . . ?
C11 C4 C14 122.63(13) . . ?
C11 C4 C18 119.03(14) . . ?
C18 C4 C14 118.30(14) . . ?
C2 C5 H5 120.1 . . ?
C7 C5 C2 119.79(14) . . ?
C7 C5 H5 120.1 . . ?
O3 C6 N1 119.94(12) . . ?
O3 C6 C16 124.29(12) . . ?
N1 C6 C16 115.76(11) . . ?
C5 C7 H7 119.9 . . ?
C5 C7 C10 120.29(14) . . ?
C10 C7 H7 119.9 . . ?
C10 C8 C13 119.23(12) . . ?
C10 C8 C19 120.36(12) . . ?
C13 C8 C19 120.39(12) . . ?
C15 C9 H9 120.1 . . ?
C17 C9 H9 120.1 . . ?
C17 C9 C15 119.88(15) . . ?
C7 C10 H10 119.9 . . ?
C8 C10 C7 120.21(14) . . ?
C8 C10 H10 119.9 . . ?
C4 C11 H11 119.9 . . ?
C4 C11 C15 120.24(16) . . ?
C15 C11 H11 119.9 . . ?
S1 C12 H12 109.4 . . ?
C3 C12 S1 105.88(9) . . ?
C3 C12 H12 109.4 . . ?
C16 C12 S1 110.08(9) . . ?
C16 C12 C3 112.74(11) . . ?
C16 C12 H12 109.4 . . ?
C2 C13 C8 119.98(14) . . ?
C2 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
O2 C14 N2 124.79(13) . . ?
O2 C14 C4 120.30(13) . . ?
N2 C14 C4 114.89(12) . . ?
C9 C15 C11 120.25(18) . . ?
C9 C15 H15 119.9 . . ?
C11 C15 H15 119.9 . . ?
C6 C16 C12 112.58(11) . . ?
C6 C16 H16A 109.1 . . ?
C6 C16 H16B 109.1 . . ?
C12 C16 H16A 109.1 . . ?
C12 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C9 C17 H17 119.7 . . ?
C9 C17 C18 120.64(17) . . ?
C18 C17 H17 119.7 . . ?
C4 C18 H18 120.0 . . ?
C17 C18 C4 119.94(17) . . ?
C17 C18 H18 120.0 . . ?
O1 C19 C8 105.22(10) . . ?
O1 C19 H19A 110.7 . . ?
O1 C19 H19B 110.7 . . ?
C8 C19 H19A 110.7 . . ?
C8 C19 H19B 110.7 . . ?
H19A C19 H19B 108.8 . . ?

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 C12 C16 C6 -64.71(12) . . . . ?
O1 N1 C1 S1 157.28(8) . . . . ?
O1 N1 C1 N2 -22.04(16) . . . . ?
O1 N1 C6 O3 6.55(17) . . . . ?
O1 N1 C6 C16 -174.07(10) . . . . ?
O3 C6 C16 C12 -139.15(13) . . . . ?
N1 O1 C19 C8 -178.32(10) . . . . ?
N1 C6 C16 C12 41.50(16) . . . . ?
C1 S1 C12 C3 165.39(9) . . . . ?
C1 S1 C12 C16 43.27(10) . . . . ?
C1 N1 C6 O3 -173.95(13) . . . . ?
C1 N1 C6 C16 5.44(19) . . . . ?
C1 N2 C14 O2 -1.9(2) . . . . ?
C1 N2 C14 C4 176.90(12) . . . . ?
C2 C5 C7 C10 0.5(2) . . . . ?
C3 C12 C16 C6 177.33(11) . . . . ?
C4 C11 C15 C9 -1.3(3) . . . . ?
C5 C2 C13 C8 -1.3(2) . . . . ?
C5 C7 C10 C8 -0.4(2) . . . . ?
C6 N1 C1 S1 -22.23(18) . . . . ?
C6 N1 C1 N2 158.46(13) . . . . ?
C9 C17 C18 C4 -1.6(3) . . . . ?
C10 C8 C13 C2 1.3(2) . . . . ?
C10 C8 C19 O1 -128.42(13) . . . . ?
C11 C4 C14 O2 161.60(15) . . . . ?
C11 C4 C14 N2 -17.3(2) . . . . ?
C11 C4 C18 C17 0.9(2) . . . . ?
C12 S1 C1 N1 -3.84(11) . . . . ?
C12 S1 C1 N2 175.41(11) . . . . ?
C13 C2 C5 C7 0.4(3) . . . . ?
C13 C8 C10 C7 -0.5(2) . . . . ?
C13 C8 C19 O1 49.87(16) . . . . ?
C14 N2 C1 S1 -0.61(18) . . . . ?
C14 N2 C1 N1 178.65(11) . . . . ?
C14 C4 C11 C15 -177.07(14) . . . . ?
C14 C4 C18 C17 178.60(14) . . . . ?
C15 C9 C17 C18 0.8(3) . . . . ?
C17 C9 C15 C11 0.7(3) . . . . ?
C18 C4 C11 C15 0.5(2) . . . . ?
C18 C4 C14 O2 -16.0(2) . . . . ?
C18 C4 C14 N2 165.16(13) . . . . ?
C19 O1 N1 C1 94.73(13) . . . . ?
C19 O1 N1 C6 -85.69(13) . . . . ?
C19 C8 C10 C7 177.84(13) . . . . ?
C19 C8 C13 C2 -177.02(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
