# 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_exp_14648_auto
_database_code_depnum_ccdc_archive 'CCDC 2449045'
loop_
_audit_author_name
_audit_author_address
wanbin
;Guangxi university
China
;
_audit_update_record             
;
2025-05-06 deposited with the CCDC.	2025-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 N O2 S'
_chemical_formula_weight         321.38

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'
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'
H H 0.0000 0.0000 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   14.5392(14)
_cell_length_b                   5.8693(6)
_cell_length_c                   18.7308(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.041(9)
_cell_angle_gamma                90
_cell_volume                     1597.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.211
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11695
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.804
_diffrn_reflns_theta_max         29.424
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3694
_reflns_number_gt                2033
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0280P)²+0.2629P] 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         3694
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1365
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
S1 S 0.14764(5) 0.66286(13) 0.69663(4) 0.0556(2) Uani 1 1 d . . . . .
O2 O 0.14285(13) 0.2624(3) 0.44572(9) 0.0612(5) Uani 1 1 d . . . . .
O1 O 0.09203(15) 0.6017(3) 0.40657(10) 0.0732(6) Uani 1 1 d . . . . .
N1 N 0.08966(15) 1.0645(4) 0.72333(12) 0.0536(6) Uani 1 1 d . . . . .
C14 C 0.23982(18) 0.1335(5) 0.35167(12) 0.0439(6) Uani 1 1 d . . . . .
C6 C 0.13111(16) 0.8565(5) 0.83241(13) 0.0449(6) Uani 1 1 d . . . . .
C12 C 0.11945(18) 0.4810(5) 0.45414(14) 0.0490(7) Uani 1 1 d . . . . .
C9 C 0.11146(17) 0.8302(5) 0.62566(13) 0.0465(7) Uani 1 1 d . . . . .
C10 C 0.10777(17) 0.7512(5) 0.55270(13) 0.0506(7) Uani 1 1 d . . . . .
H10 H 0.087008 0.855355 0.518347 0.061 Uiso 1 1 calc R U . . .
C7 C 0.12186(16) 0.8805(5) 0.75459(13) 0.0455(7) Uani 1 1 d . . . . .
C11 C 0.13055(17) 0.5480(5) 0.52936(13) 0.0511(7) Uani 1 1 d . . . . .
H11 H 0.154721 0.442543 0.561981 0.061 Uiso 1 1 calc R U . . .
C8 C 0.08409(18) 1.0338(5) 0.65114(14) 0.0541(7) Uani 1 1 d . . . . .
H8 H 0.062332 1.148286 0.620661 0.065 Uiso 1 1 calc R U . . .
C15 C 0.2848(2) 0.2917(5) 0.31214(13) 0.0533(7) Uani 1 1 d . . . . .
H15 H 0.255041 0.426272 0.298987 0.064 Uiso 1 1 calc R U . . .
C5 C 0.16568(19) 0.6598(5) 0.86397(15) 0.0607(8) Uani 1 1 d . . . . .
H5 H 0.186587 0.542173 0.835501 0.073 Uiso 1 1 calc R U . . .
C19 C 0.2855(2) -0.0643(5) 0.37089(13) 0.0574(8) Uani 1 1 d . . . . .
H19 H 0.256022 -0.173479 0.397835 0.069 Uiso 1 1 calc R U . . .
C13 C 0.14277(19) 0.1703(5) 0.37320(14) 0.0617(8) Uani 1 1 d . . . . .
H13A H 0.112079 0.275809 0.340372 0.074 Uiso 1 1 calc R U . . .
H13B H 0.109519 0.027037 0.371301 0.074 Uiso 1 1 calc R U . . .
C1 C 0.10127(19) 1.0295(5) 0.87594(14) 0.0588(8) Uani 1 1 d . . . . .
H1 H 0.078631 1.163890 0.855750 0.071 Uiso 1 1 calc R U . . .
C17 C 0.4173(2) 0.0589(7) 0.31021(16) 0.0715(10) Uani 1 1 d . . . . .
H17 H 0.476898 0.034032 0.295407 0.086 Uiso 1 1 calc R U . . .
C3 C 0.1378(2) 0.8073(6) 0.97992(16) 0.0704(9) Uani 1 1 d . . . . .
H3 H 0.138747 0.789761 1.029284 0.084 Uiso 1 1 calc R U . . .
C16 C 0.3728(2) 0.2549(6) 0.29173(14) 0.0686(9) Uani 1 1 d . . . . .
H16 H 0.402420 0.364602 0.265037 0.082 Uiso 1 1 calc R U . . .
C4 C 0.1694(2) 0.6366(6) 0.93720(17) 0.0722(9) Uani 1 1 d . . . . .
H4 H 0.193470 0.504298 0.957814 0.087 Uiso 1 1 calc R U . . .
C2 C 0.10486(19) 1.0038(6) 0.94909(15) 0.0696(9) Uani 1 1 d . . . . .
H2 H 0.084658 1.121475 0.977870 0.084 Uiso 1 1 calc R U . . .
C18 C 0.3750(2) -0.1024(6) 0.35051(17) 0.0706(9) Uani 1 1 d . . . . .
H18 H 0.405850 -0.235358 0.363987 0.085 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 C9 1.720(3) . ?
S1 C7 1.726(3) . ?
O2 C12 1.338(3) . ?
O2 C13 1.462(3) . ?
O1 C12 1.196(3) . ?
N1 C7 1.307(3) . ?
N1 C8 1.364(3) . ?
C14 C15 1.369(3) . ?
C14 C19 1.379(3) . ?
C14 C13 1.497(3) . ?
C6 C1 1.381(3) . ?
C6 C5 1.384(3) . ?
C6 C7 1.466(3) . ?
C12 C11 1.466(3) . ?
C9 C8 1.352(3) . ?
C9 C10 1.442(3) . ?
C10 C11 1.317(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C8 H8 0.9300 . ?
C15 C16 1.365(4) . ?
C15 H15 0.9300 . ?
C5 C4 1.378(4) . ?
C5 H5 0.9300 . ?
C19 C18 1.387(4) . ?
C19 H19 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C1 C2 1.378(3) . ?
C1 H1 0.9300 . ?
C17 C16 1.359(4) . ?
C17 C18 1.370(4) . ?
C17 H17 0.9300 . ?
C3 C2 1.369(4) . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C16 H16 0.9300 . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
C18 H18 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
C9 S1 C7 89.79(13) . . ?
C12 O2 C13 118.2(2) . . ?
C7 N1 C8 110.0(2) . . ?
C15 C14 C19 118.5(3) . . ?
C15 C14 C13 121.4(3) . . ?
C19 C14 C13 120.1(3) . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 C7 119.8(3) . . ?
C5 C6 C7 121.6(3) . . ?
O1 C12 O2 124.0(3) . . ?
O1 C12 C11 125.4(3) . . ?
O2 C12 C11 110.5(2) . . ?
C8 C9 C10 128.1(3) . . ?
C8 C9 S1 108.51(19) . . ?
C10 C9 S1 123.3(2) . . ?
C11 C10 C9 127.2(3) . . ?
C11 C10 H10 116.4 . . ?
C9 C10 H10 116.4 . . ?
N1 C7 C6 122.9(2) . . ?
N1 C7 S1 114.33(19) . . ?
C6 C7 S1 122.7(2) . . ?
C10 C11 C12 122.8(3) . . ?
C10 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C9 C8 N1 117.3(2) . . ?
C9 C8 H8 121.3 . . ?
N1 C8 H8 121.3 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C14 C19 C18 120.8(3) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
O2 C13 C14 109.5(2) . . ?
O2 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
O2 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C2 C1 C6 120.3(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C17 C18 C19 118.9(3) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?

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
C13 O2 C12 O1 5.6(4) . . . . ?
C13 O2 C12 C11 -175.4(2) . . . . ?
C7 S1 C9 C8 0.5(2) . . . . ?
C7 S1 C9 C10 -176.3(2) . . . . ?
C8 C9 C10 C11 -176.3(3) . . . . ?
S1 C9 C10 C11 -0.2(4) . . . . ?
C8 N1 C7 C6 -176.6(2) . . . . ?
C8 N1 C7 S1 0.6(3) . . . . ?
C1 C6 C7 N1 2.9(4) . . . . ?
C5 C6 C7 N1 -179.8(3) . . . . ?
C1 C6 C7 S1 -174.0(2) . . . . ?
C5 C6 C7 S1 3.3(3) . . . . ?
C9 S1 C7 N1 -0.6(2) . . . . ?
C9 S1 C7 C6 176.5(2) . . . . ?
C9 C10 C11 C12 176.6(2) . . . . ?
O1 C12 C11 C10 2.4(4) . . . . ?
O2 C12 C11 C10 -176.5(2) . . . . ?
C10 C9 C8 N1 176.3(2) . . . . ?
S1 C9 C8 N1 -0.3(3) . . . . ?
C7 N1 C8 C9 -0.2(3) . . . . ?
C19 C14 C15 C16 0.3(4) . . . . ?
C13 C14 C15 C16 -178.9(2) . . . . ?
C1 C6 C5 C4 0.6(4) . . . . ?
C7 C6 C5 C4 -176.7(2) . . . . ?
C15 C14 C19 C18 -0.1(4) . . . . ?
C13 C14 C19 C18 179.1(2) . . . . ?
C12 O2 C13 C14 108.1(3) . . . . ?
C15 C14 C13 O2 -96.7(3) . . . . ?
C19 C14 C13 O2 84.1(3) . . . . ?
C5 C6 C1 C2 -0.9(4) . . . . ?
C7 C6 C1 C2 176.4(2) . . . . ?
C18 C17 C16 C15 -1.1(5) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C2 C3 C4 C5 -1.8(5) . . . . ?
C6 C5 C4 C3 0.8(5) . . . . ?
C4 C3 C2 C1 1.5(5) . . . . ?
C6 C1 C2 C3 -0.1(5) . . . . ?
C16 C17 C18 C19 1.3(5) . . . . ?
C14 C19 C18 C17 -0.7(4) . . . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.040

