# Electronic Supplementary Material (ESI) for Chemical Science.
# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2250745'
loop_
_audit_author_name
_audit_author_address
Xanthate
;Northwest University
China
;
_audit_update_record             
;
2023-03-22 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_audit_creation_date             2023-03-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 N O3 S2'
_chemical_formula_sum            'C11 H9 N O3 S2'
_chemical_formula_weight         267.31
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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                   10.3474(8)
_cell_length_b                   14.3530(10)
_cell_length_c                   8.1480(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.271(4)
_cell_angle_gamma                90
_cell_volume                     1194.30(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8568
_cell_measurement_temperature    260.00
_cell_measurement_theta_max      56.927
_cell_measurement_theta_min      2.679
_shelx_estimated_absorpt_T_max   0.742
_shelx_estimated_absorpt_T_min   0.619
_exptl_absorpt_coefficient_mu    2.650
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.4662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1586 before and 0.0642 after correction.
The Ratio of minimum to maximum transmission is 0.6206.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17614
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.106
_diffrn_reflns_theta_min         3.766
_diffrn_ambient_temperature      260.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.19985679999999997
_diffrn_source_voltage           69.88
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1846
_reflns_number_total             2442
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2442
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.141
_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)+(0.0738P)²+0.1734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1335
_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. Rigid bond restraints
 S2, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C7(H7), C8(H8)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.21464(6) 0.37611(4) 0.39588(7) 0.0450(2) Uani 1 1 d . . . . .
S2 S -0.06518(6) 0.37874(4) 0.38610(8) 0.0489(2) Uani 1 1 d . U . . .
O1 O 0.11018(14) 0.37468(9) 0.66364(18) 0.0385(4) Uani 1 1 d . . . . .
O2 O 0.36404(15) 0.21141(11) 0.5800(2) 0.0532(4) Uani 1 1 d . . . . .
O3 O 0.37564(17) 0.53088(10) 0.5953(2) 0.0532(4) Uani 1 1 d . . . . .
N1 N 0.34492(17) 0.37201(11) 0.5489(2) 0.0387(4) Uani 1 1 d . . . . .
C5 C 0.5113(2) 0.31801(14) 0.7488(3) 0.0365(5) Uani 1 1 d . . . . .
C10 C 0.5130(2) 0.41512(14) 0.7575(3) 0.0372(5) Uani 1 1 d . . . . .
C11 C 0.4070(2) 0.45126(15) 0.6298(3) 0.0385(5) Uani 1 1 d . . . . .
C3 C 0.0796(2) 0.37639(12) 0.5000(3) 0.0356(5) Uani 1 1 d . U . . .
C4 C 0.4018(2) 0.28856(14) 0.6209(3) 0.0384(5) Uani 1 1 d . . . . .
C6 C 0.6015(2) 0.26489(16) 0.8533(3) 0.0463(5) Uani 1 1 d . . . . .
H6 H 0.601741 0.200206 0.846623 0.056 Uiso 1 1 calc R U . . .
C9 C 0.6028(2) 0.46222(17) 0.8714(3) 0.0465(6) Uani 1 1 d . . . . .
H9 H 0.603854 0.526952 0.876458 0.056 Uiso 1 1 calc R U . . .
C1 C 0.0617(3) 0.37946(16) 0.9388(3) 0.0508(6) Uani 1 1 d . . . . .
H1A H 0.127239 0.332056 0.964948 0.076 Uiso 1 1 calc R U . . .
H1B H -0.005057 0.371273 1.006810 0.076 Uiso 1 1 calc R U . . .
H1C H 0.101252 0.439702 0.959752 0.076 Uiso 1 1 calc R U . . .
C7 C 0.6916(2) 0.31232(19) 0.9682(3) 0.0536(6) Uani 1 1 d . . . . .
H7 H 0.753325 0.278585 1.040045 0.064 Uiso 1 1 calc R U . . .
C2 C 0.0023(2) 0.37226(14) 0.7602(3) 0.0455(6) Uani 1 1 d . . . . .
H2A H -0.046312 0.314492 0.739839 0.055 Uiso 1 1 calc R U . . .
H2B H -0.057177 0.423849 0.729027 0.055 Uiso 1 1 calc R U . . .
C8 C 0.6916(2) 0.40876(19) 0.9786(3) 0.0548(6) Uani 1 1 d . . . . .
H8 H 0.752176 0.438252 1.058616 0.066 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 N1 1.6832(19) . ?
S1 C3 1.747(2) . ?
S2 C3 1.631(2) . ?
O1 C3 1.320(3) . ?
O1 C2 1.466(3) . ?
O2 C4 1.204(3) . ?
O3 C11 1.209(3) . ?
N1 C11 1.416(3) . ?
N1 C4 1.419(3) . ?
C5 C10 1.396(3) . ?
C5 C4 1.472(3) . ?
C5 C6 1.386(3) . ?
C10 C11 1.479(3) . ?
C10 C9 1.380(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.388(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.392(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.490(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 H8 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
N1 S1 C3 104.36(10) . . ?
C3 O1 C2 117.59(16) . . ?
C11 N1 S1 124.46(14) . . ?
C11 N1 C4 111.00(17) . . ?
C4 N1 S1 124.42(14) . . ?
C10 C5 C4 108.92(19) . . ?
C6 C5 C10 121.1(2) . . ?
C6 C5 C4 129.9(2) . . ?
C5 C10 C11 108.24(19) . . ?
C9 C10 C5 121.7(2) . . ?
C9 C10 C11 130.1(2) . . ?
O3 C11 N1 124.5(2) . . ?
O3 C11 C10 129.5(2) . . ?
N1 C11 C10 105.97(17) . . ?
S2 C3 S1 117.18(13) . . ?
O1 C3 S1 114.22(15) . . ?
O1 C3 S2 128.60(17) . . ?
O2 C4 N1 124.5(2) . . ?
O2 C4 C5 129.7(2) . . ?
N1 C4 C5 105.74(17) . . ?
C5 C6 H6 121.4 . . ?
C5 C6 C7 117.2(2) . . ?
C7 C6 H6 121.4 . . ?
C10 C9 H9 121.4 . . ?
C10 C9 C8 117.2(2) . . ?
C8 C9 H9 121.4 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.6(2) . . ?
C8 C7 H7 119.2 . . ?
O1 C2 C1 107.00(18) . . ?
O1 C2 H2A 110.3 . . ?
O1 C2 H2B 110.3 . . ?
C1 C2 H2A 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
C9 C8 H8 119.4 . . ?
C7 C8 C9 121.2(2) . . ?
C7 C8 H8 119.4 . . ?

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 O3 -2.0(3) . . . . ?
S1 N1 C11 C10 178.34(14) . . . . ?
S1 N1 C4 O2 0.6(3) . . . . ?
S1 N1 C4 C5 -179.62(13) . . . . ?
N1 S1 C3 S2 -179.23(10) . . . . ?
N1 S1 C3 O1 0.81(16) . . . . ?
C5 C10 C11 O3 -179.5(2) . . . . ?
C5 C10 C11 N1 0.2(2) . . . . ?
C5 C10 C9 C8 -0.3(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C10 C5 C4 O2 -176.9(2) . . . . ?
C10 C5 C4 N1 3.4(2) . . . . ?
C10 C5 C6 C7 1.2(3) . . . . ?
C10 C9 C8 C7 1.5(3) . . . . ?
C11 N1 C4 O2 176.9(2) . . . . ?
C11 N1 C4 C5 -3.3(2) . . . . ?
C11 C10 C9 C8 179.5(2) . . . . ?
C3 S1 N1 C11 -87.84(18) . . . . ?
C3 S1 N1 C4 87.98(18) . . . . ?
C3 O1 C2 C1 -174.93(16) . . . . ?
C4 N1 C11 O3 -178.30(19) . . . . ?
C4 N1 C11 C10 2.0(2) . . . . ?
C4 C5 C10 C11 -2.2(2) . . . . ?
C4 C5 C10 C9 177.61(19) . . . . ?
C4 C5 C6 C7 -177.2(2) . . . . ?
C6 C5 C10 C11 179.18(19) . . . . ?
C6 C5 C10 C9 -1.0(3) . . . . ?
C6 C5 C4 O2 1.6(4) . . . . ?
C6 C5 C4 N1 -178.2(2) . . . . ?
C6 C7 C8 C9 -1.3(4) . . . . ?
C9 C10 C11 O3 0.7(4) . . . . ?
C9 C10 C11 N1 -179.6(2) . . . . ?
C2 O1 C3 S1 -178.40(13) . . . . ?
C2 O1 C3 S2 1.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
