# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_330831d_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2328548'
loop_
_audit_author_name
_audit_author_address
'Xinwei He'
;Anhui Normal University
China
;
_audit_update_record             
;
2024-01-26 deposited with the CCDC.	2024-04-04 downloaded from the CCDC.
;
_audit_creation_date             2022-10-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 N2 O3 S'
_chemical_formula_sum            'C19 H16 N2 O3 S'
_chemical_formula_weight         352.40
_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                   11.45(2)
_cell_length_b                   8.899(16)
_cell_length_c                   17.03(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.80(3)
_cell_angle_gamma                90
_cell_volume                     1698(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7947
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      27.242
_cell_measurement_theta_min      2.384
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1185 before and 0.0538 after correction.
The Ratio of minimum to maximum transmission is 0.7131.
The λ/2 correction factor is Not present.
;
_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    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_mounting_method   
'The title complex was mounted in a sealed capillary.'
_exptl_crystal_recrystallization_method 
'The crystals were growth by means of evaporation of a mixture of n-hexane and toluene at RT.'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18605
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         1.818
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3156
_reflns_number_total             3868
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker SMART APEX II diffractrometer'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0612P)²+0.4056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1160
_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 Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C)
;
_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 0.57876(3) 0.35377(4) 0.68303(2) 0.03498(13) Uani 1 1 d . . . . .
O1 O 0.65421(11) 0.24903(13) 0.73486(7) 0.0479(3) Uani 1 1 d . . . . .
O3 O 0.46378(12) 0.14259(16) 0.38212(8) 0.0575(4) Uani 1 1 d . . . . .
O4 O 0.24395(11) 0.09691(16) 0.57681(8) 0.0572(3) Uani 1 1 d . . . . .
N1 N 0.44783(11) 0.29549(16) 0.64902(8) 0.0394(3) Uani 1 1 d . . . . .
N2 N 0.33363(12) 0.09455(16) 0.46657(8) 0.0414(3) Uani 1 1 d . . . . .
C1 C 0.56215(18) 0.5171(2) 0.73751(10) 0.0491(4) Uani 1 1 d . . . . .
H1A H 0.512504 0.495832 0.775263 0.074 Uiso 1 1 calc R U . . .
H1B H 0.525782 0.594428 0.701304 0.074 Uiso 1 1 calc R U . . .
H1C H 0.639088 0.550470 0.765756 0.074 Uiso 1 1 calc R U . . .
C2 C 0.64407(14) 0.40561(17) 0.60240(9) 0.0353(3) Uani 1 1 d . . . . .
C3 C 0.60127(13) 0.33934(16) 0.52649(9) 0.0342(3) Uani 1 1 d . . . . .
C4 C 0.66438(15) 0.37102(18) 0.46538(10) 0.0412(4) Uani 1 1 d . . . . .
H4 H 0.639538 0.326843 0.415255 0.049 Uiso 1 1 calc R U . . .
C5 C 0.76253(15) 0.4663(2) 0.47800(11) 0.0461(4) Uani 1 1 d . . . . .
C6 C 0.80103(16) 0.5303(2) 0.55398(12) 0.0514(4) Uani 1 1 d . . . . .
H6 H 0.866287 0.594920 0.562744 0.062 Uiso 1 1 calc R U . . .
C7 C 0.74416(15) 0.49953(19) 0.61596(11) 0.0459(4) Uani 1 1 d . . . . .
H7 H 0.772067 0.540844 0.666474 0.055 Uiso 1 1 calc R U . . .
C8 C 0.82539(19) 0.5031(3) 0.41080(14) 0.0665(6) Uani 1 1 d . . . . .
H8A H 0.821090 0.609330 0.400811 0.100 Uiso 1 1 calc R U . . .
H8B H 0.787637 0.450390 0.363164 0.100 Uiso 1 1 calc R U . . .
H8C H 0.907499 0.472999 0.425633 0.100 Uiso 1 1 calc R U . . .
C9 C 0.49587(14) 0.24705(17) 0.51683(9) 0.0346(3) Uani 1 1 d . . . . .
C10 C 0.43549(14) 0.15973(18) 0.44659(10) 0.0389(4) Uani 1 1 d . . . . .
C11 C 0.43010(13) 0.23379(16) 0.57485(9) 0.0341(3) Uani 1 1 d . . . . .
C12 C 0.32262(14) 0.13510(18) 0.54322(10) 0.0396(4) Uani 1 1 d . . . . .
C13 C 0.25148(16) -0.00671(19) 0.41356(11) 0.0470(4) Uani 1 1 d . . . . .
H13A H 0.221065 -0.080679 0.446124 0.056 Uiso 1 1 calc R U . . .
H13B H 0.295480 -0.059969 0.379211 0.056 Uiso 1 1 calc R U . . .
C14 C 0.14724(15) 0.07399(17) 0.36163(10) 0.0412(4) Uani 1 1 d . . . . .
C15 C 0.16161(17) 0.1489(2) 0.29287(11) 0.0503(4) Uani 1 1 d . . . . .
H15 H 0.235677 0.148542 0.278393 0.060 Uiso 1 1 calc R U . . .
C16 C 0.0669(2) 0.2245(2) 0.24545(12) 0.0622(5) Uani 1 1 d . . . . .
H16 H 0.077716 0.275635 0.199860 0.075 Uiso 1 1 calc R U . . .
C17 C -0.04391(19) 0.2235(2) 0.26620(14) 0.0676(6) Uani 1 1 d . . . . .
H17 H -0.107423 0.274613 0.234607 0.081 Uiso 1 1 calc R U . . .
C18 C -0.06038(18) 0.1477(3) 0.33292(15) 0.0665(6) Uani 1 1 d . . . . .
H18 H -0.135363 0.145735 0.346025 0.080 Uiso 1 1 calc R U . . .
C19 C 0.03488(17) 0.0737(2) 0.38119(12) 0.0543(5) Uani 1 1 d . . . . .
H19 H 0.023503 0.023602 0.426957 0.065 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 1.443(2) . ?
S1 N1 1.580(3) . ?
S1 C1 1.756(3) . ?
S1 C2 1.754(3) . ?
O3 C10 1.216(3) . ?
O4 C12 1.210(3) . ?
N1 C11 1.354(3) . ?
N2 C10 1.405(3) . ?
N2 C12 1.385(3) . ?
N2 C13 1.471(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.414(3) . ?
C2 C7 1.399(3) . ?
C3 C4 1.411(3) . ?
C3 C9 1.441(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(3) . ?
C5 C6 1.400(3) . ?
C5 C8 1.507(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(3) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.475(3) . ?
C9 C11 1.364(3) . ?
C11 C12 1.518(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.513(3) . ?
C14 C15 1.386(3) . ?
C14 C19 1.393(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.367(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.390(3) . ?
C19 H19 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
O1 S1 N1 114.61(12) . . ?
O1 S1 C1 109.11(15) . . ?
O1 S1 C2 110.56(13) . . ?
N1 S1 C1 105.58(11) . . ?
N1 S1 C2 108.88(13) . . ?
C2 S1 C1 107.79(13) . . ?
C11 N1 S1 115.16(12) . . ?
C10 N2 C13 124.21(17) . . ?
C12 N2 C10 111.15(14) . . ?
C12 N2 C13 124.62(16) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 S1 118.85(16) . . ?
C7 C2 S1 119.58(15) . . ?
C7 C2 C3 121.27(15) . . ?
C2 C3 C9 117.88(15) . . ?
C4 C3 C2 117.19(18) . . ?
C4 C3 C9 124.93(16) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.85(18) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 118.90(17) . . ?
C4 C5 C8 120.8(2) . . ?
C6 C5 C8 120.3(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 H7 120.3 . . ?
C6 C7 C2 119.49(18) . . ?
C6 C7 H7 120.3 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 C10 129.47(15) . . ?
C11 C9 C3 122.66(16) . . ?
C11 C9 C10 107.79(18) . . ?
O3 C10 N2 123.66(15) . . ?
O3 C10 C9 129.15(18) . . ?
N2 C10 C9 107.19(16) . . ?
N1 C11 C9 129.87(17) . . ?
N1 C11 C12 121.44(14) . . ?
C9 C11 C12 108.68(17) . . ?
O4 C12 N2 126.33(17) . . ?
O4 C12 C11 128.48(18) . . ?
N2 C12 C11 105.18(15) . . ?
N2 C13 H13A 108.9 . . ?
N2 C13 H13B 108.9 . . ?
N2 C13 C14 113.37(18) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C15 C14 C13 120.42(19) . . ?
C15 C14 C19 118.53(17) . . ?
C19 C14 C13 121.0(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.30(19) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.6(2) . . ?
C18 C19 H19 119.7 . . ?

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 N1 C11 C9 -18.7(2) . . . . ?
S1 N1 C11 C12 162.79(12) . . . . ?
S1 C2 C3 C4 -173.20(11) . . . . ?
S1 C2 C3 C9 7.84(19) . . . . ?
S1 C2 C7 C6 174.81(13) . . . . ?
O1 S1 N1 C11 -96.18(16) . . . . ?
O1 S1 C2 C3 102.15(18) . . . . ?
O1 S1 C2 C7 -71.67(19) . . . . ?
N1 S1 C2 C3 -24.61(15) . . . . ?
N1 S1 C2 C7 161.57(13) . . . . ?
N1 C11 C12 O4 -1.4(3) . . . . ?
N1 C11 C12 N2 179.40(13) . . . . ?
N2 C13 C14 C15 79.2(2) . . . . ?
N2 C13 C14 C19 -101.4(2) . . . . ?
C1 S1 N1 C11 143.72(12) . . . . ?
C1 S1 C2 C3 -138.67(14) . . . . ?
C1 S1 C2 C7 47.51(16) . . . . ?
C2 S1 N1 C11 28.22(15) . . . . ?
C2 C3 C4 C5 -1.7(2) . . . . ?
C2 C3 C9 C10 -176.91(14) . . . . ?
C2 C3 C9 C11 6.7(2) . . . . ?
C3 C2 C7 C6 1.1(3) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C3 C4 C5 C8 -177.57(16) . . . . ?
C3 C9 C10 O3 2.7(3) . . . . ?
C3 C9 C10 N2 -177.47(15) . . . . ?
C3 C9 C11 N1 -1.5(3) . . . . ?
C3 C9 C11 C12 177.10(13) . . . . ?
C4 C3 C9 C10 4.2(3) . . . . ?
C4 C3 C9 C11 -172.18(14) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C2 -1.7(3) . . . . ?
C7 C2 C3 C4 0.5(2) . . . . ?
C7 C2 C3 C9 -178.45(14) . . . . ?
C8 C5 C6 C7 179.32(17) . . . . ?
C9 C3 C4 C5 177.18(15) . . . . ?
C9 C11 C12 O4 179.78(17) . . . . ?
C9 C11 C12 N2 0.62(17) . . . . ?
C10 N2 C12 O4 179.77(16) . . . . ?
C10 N2 C12 C11 -1.05(17) . . . . ?
C10 N2 C13 C14 -92.5(2) . . . . ?
C10 C9 C11 N1 -178.62(15) . . . . ?
C10 C9 C11 C12 0.02(16) . . . . ?
C11 C9 C10 O3 179.48(17) . . . . ?
C11 C9 C10 N2 -0.65(17) . . . . ?
C12 N2 C10 O3 -179.03(16) . . . . ?
C12 N2 C10 C9 1.09(17) . . . . ?
C12 N2 C13 C14 89.2(2) . . . . ?
C13 N2 C10 O3 2.5(2) . . . . ?
C13 N2 C10 C9 -177.40(13) . . . . ?
C13 N2 C12 O4 -1.7(3) . . . . ?
C13 N2 C12 C11 177.43(13) . . . . ?
C13 C14 C15 C16 -179.30(16) . . . . ?
C13 C14 C19 C18 -179.76(17) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C15 C14 C19 C18 -0.3(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 C19 1.3(3) . . . . ?
C17 C18 C19 C14 -0.9(3) . . . . ?
C19 C14 C15 C16 1.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
