# Supplementary Information (SI) for Green 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. 
# 
#######################################################################

data_22
_database_code_depnum_ccdc_archive 'CCDC 2393039'
loop_
_audit_author_name
_audit_author_address
'Long-Yong Xie'
;Hunan University of Science and Engineering
China
;
_audit_update_record             
;
2024-10-23 deposited with the CCDC.	2024-11-05 downloaded from the CCDC.
;
_audit_creation_date             2024-10-23
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H18 N2 O6 S2'
_chemical_formula_sum            'C18 H18 N2 O6 S2'
_chemical_formula_weight         422.46
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.909(2)
_cell_length_b                   10.4158(18)
_cell_length_c                   15.096(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.127(2)
_cell_angle_gamma                90.00
_cell_volume                     2018.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4370
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.77
_cell_measurement_theta_min      2.38
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6974
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
? was used for absorption correction.
R(int) was 0.0551 before and 0.0451 after correction.
The Ratio of minimum to maximum transmission is 0.9354.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22291
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         1.59
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3215
_reflns_number_total             4628
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4628
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0661P)²+0.5313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1368
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.79122(5) 0.90659(6) 0.15622(4) 0.05317(19) Uani 1 1 d . . .
S2 S 0.63878(4) 1.12904(6) 0.01928(4) 0.05401(19) Uani 1 1 d . . .
C2 C 0.72038(16) 0.8769(2) 0.05003(13) 0.0436(5) Uani 1 1 d . . .
O3 O 0.89825(13) 0.91245(18) 0.14246(12) 0.0708(5) Uani 1 1 d . . .
C1 C 0.66497(16) 0.9644(2) 0.00267(13) 0.0456(5) Uani 1 1 d . . .
H1 H 0.6328 0.9328 -0.0510 0.055 Uiso 1 1 calc R . .
C3 C 0.73057(17) 0.7449(2) 0.01438(13) 0.0482(5) Uani 1 1 d . . .
C15 C 0.75331(17) 1.2024(2) 0.06021(15) 0.0515(5) Uani 1 1 d . . .
C10 C 0.76982(19) 0.7700(2) 0.21578(14) 0.0572(6) Uani 1 1 d . . .
O5 O 0.61219(15) 1.17567(18) -0.06913(12) 0.0799(6) Uani 1 1 d . . .
O4 O 0.74452(16) 1.01091(18) 0.19722(11) 0.0765(5) Uani 1 1 d . . .
C4 C 0.6472(2) 0.6620(3) 0.00908(18) 0.0667(7) Uani 1 1 d . . .
H4 H 0.5853 0.6866 0.0306 0.080 Uiso 1 1 calc R . .
O6 O 0.56450(13) 1.14206(19) 0.08150(15) 0.0798(6) Uani 1 1 d . . .
C9 C 0.8386(3) 0.6735(3) 0.23995(17) 0.0743(8) Uani 1 1 d . . .
C16 C 0.8458(2) 1.2041(3) 0.02192(18) 0.0650(7) Uani 1 1 d . . .
C14 C 0.7696(2) 1.2786(3) 0.13528(19) 0.0700(7) Uani 1 1 d . . .
C11 C 0.6787(2) 0.7393(3) 0.25328(16) 0.0741(8) Uani 1 1 d . . .
O2 O 0.86475(18) 1.3243(2) 0.14137(16) 0.0996(7) Uani 1 1 d U . .
N2 N 0.91433(17) 1.2752(3) 0.06897(19) 0.0838(7) Uani 1 1 d U . .
C8 C 0.8217(2) 0.7067(3) -0.01686(17) 0.0655(7) Uani 1 1 d . . .
H8 H 0.8787 0.7617 -0.0126 0.079 Uiso 1 1 calc R . .
N1 N 0.6905(3) 0.6334(3) 0.29773(16) 0.0952(8) Uani 1 1 d U . .
C6 C 0.7457(3) 0.5053(3) -0.0599(2) 0.0832(9) Uani 1 1 d . . .
H6 H 0.7505 0.4244 -0.0853 0.100 Uiso 1 1 calc R . .
O1 O 0.7938(2) 0.5913(2) 0.29061(15) 0.1062(8) Uani 1 1 d U . .
C7 C 0.8288(3) 0.5863(3) -0.0547(2) 0.0804(8) Uani 1 1 d . . .
H7 H 0.8903 0.5608 -0.0764 0.096 Uiso 1 1 calc R . .
C12 C 0.9460(3) 0.6436(3) 0.2223(3) 0.1049(11) Uani 1 1 d . . .
H12A H 0.9459 0.6138 0.1621 0.157 Uiso 1 1 calc R . .
H12B H 0.9740 0.5780 0.2626 0.157 Uiso 1 1 calc R . .
H12C H 0.9881 0.7195 0.2306 0.157 Uiso 1 1 calc R . .
C5 C 0.6560(3) 0.5423(3) -0.0283(2) 0.0865(9) Uani 1 1 d . . .
H5 H 0.5996 0.4862 -0.0318 0.104 Uiso 1 1 calc R . .
C18 C 0.8754(3) 1.1381(4) -0.0583(2) 0.0963(10) Uani 1 1 d . . .
H18A H 0.8896 1.0494 -0.0448 0.144 Uiso 1 1 calc R . .
H18B H 0.9365 1.1778 -0.0770 0.144 Uiso 1 1 calc R . .
H18C H 0.8193 1.1443 -0.1053 0.144 Uiso 1 1 calc R . .
C17 C 0.7027(3) 1.3153(4) 0.2042(2) 0.1100(13) Uani 1 1 d . . .
H17A H 0.6506 1.3748 0.1796 0.165 Uiso 1 1 calc R . .
H17B H 0.7444 1.3548 0.2532 0.165 Uiso 1 1 calc R . .
H17C H 0.6695 1.2401 0.2249 0.165 Uiso 1 1 calc R . .
C13 C 0.5778(3) 0.8074(4) 0.2485(2) 0.1109(13) Uani 1 1 d . . .
H13A H 0.5887 0.8931 0.2709 0.166 Uiso 1 1 calc R . .
H13B H 0.5318 0.7625 0.2837 0.166 Uiso 1 1 calc R . .
H13C H 0.5474 0.8108 0.1876 0.166 Uiso 1 1 calc R . .


_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 C2 1.786(2) . ?
S1 O3 1.4203(19) . ?
S1 C10 1.721(2) . ?
S1 O4 1.4166(19) . ?
S2 C1 1.771(2) . ?
S2 C15 1.720(2) . ?
S2 O5 1.4273(19) . ?
S2 O6 1.4186(19) . ?
C2 C1 1.321(3) . ?
C2 C3 1.488(3) . ?
C3 C4 1.375(3) . ?
C3 C8 1.372(3) . ?
C15 C16 1.382(3) . ?
C15 C14 1.381(3) . ?
C10 C9 1.365(4) . ?
C10 C11 1.396(4) . ?
C4 C5 1.378(4) . ?
C9 O1 1.321(3) . ?
C9 C12 1.473(5) . ?
C16 N2 1.305(3) . ?
C16 C18 1.478(4) . ?
C14 O2 1.311(3) . ?
C14 C17 1.472(4) . ?
C11 N1 1.292(4) . ?
C11 C13 1.478(5) . ?
O2 N2 1.419(3) . ?
C8 C7 1.385(4) . ?
N1 O1 1.419(4) . ?
C6 C7 1.360(4) . ?
C6 C5 1.356(4) . ?

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
O3 S1 C2 106.81(10) . . ?
O3 S1 C10 108.95(12) . . ?
C10 S1 C2 103.31(10) . . ?
O4 S1 C2 108.92(10) . . ?
O4 S1 O3 119.80(12) . . ?
O4 S1 C10 107.84(12) . . ?
C15 S2 C1 108.15(10) . . ?
O5 S2 C1 103.16(11) . . ?
O5 S2 C15 107.24(12) . . ?
O6 S2 C1 109.82(11) . . ?
O6 S2 C15 109.61(12) . . ?
O6 S2 O5 118.33(13) . . ?
C1 C2 S1 124.19(17) . . ?
C1 C2 C3 120.39(18) . . ?
C3 C2 S1 115.37(15) . . ?
C2 C1 S2 133.81(17) . . ?
C4 C3 C2 120.2(2) . . ?
C8 C3 C2 120.3(2) . . ?
C8 C3 C4 119.5(2) . . ?
C16 C15 S2 127.14(19) . . ?
C14 C15 S2 126.9(2) . . ?
C14 C15 C16 105.9(2) . . ?
C9 C10 S1 127.8(2) . . ?
C9 C10 C11 106.0(2) . . ?
C11 C10 S1 126.1(2) . . ?
C3 C4 C5 119.6(3) . . ?
C10 C9 C12 134.9(3) . . ?
O1 C9 C10 108.6(3) . . ?
O1 C9 C12 116.5(3) . . ?
C15 C16 C18 130.4(3) . . ?
N2 C16 C15 110.2(3) . . ?
N2 C16 C18 119.4(3) . . ?
C15 C14 C17 132.8(3) . . ?
O2 C14 C15 109.0(3) . . ?
O2 C14 C17 118.1(3) . . ?
C10 C11 C13 130.3(3) . . ?
N1 C11 C10 110.3(3) . . ?
N1 C11 C13 119.4(3) . . ?
C14 O2 N2 108.1(2) . . ?
C16 N2 O2 106.8(2) . . ?
C3 C8 C7 120.1(3) . . ?
C11 N1 O1 106.5(2) . . ?
C5 C6 C7 120.1(3) . . ?
C9 O1 N1 108.5(2) . . ?
C6 C7 C8 119.9(3) . . ?
C6 C5 C4 120.8(3) . . ?

