# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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
_audit_block_doi                 10.5517/ccdc.csd.cc294q9h
_database_code_depnum_ccdc_archive 'CCDC 2119696'
loop_
_audit_author_name
_audit_author_address
'Shengqing Ye'
;Taizhou University
China
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2021-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 O4 S2'
_chemical_formula_weight         346.40

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'
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 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                   12.6898(14)
_cell_length_b                   9.9051(11)
_cell_length_c                   13.0570(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.130(2)
_cell_angle_gamma                90
_cell_volume                     1604.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3643
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.11

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.349
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7891
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.192
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2819
_reflns_number_gt                2292
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0597P)²+0.6491P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2819
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_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
S2 S 0.50031(4) 0.51814(6) 0.18252(4) 0.0453(2) Uani 1 1 d . . . . .
S1 S 0.62309(6) 0.70158(9) 0.49128(5) 0.0758(3) Uani 1 1 d . . . . .
O2 O 0.60256(13) 0.52687(19) 0.15302(12) 0.0586(5) Uani 1 1 d . . . . .
O004 O 1.01415(13) 0.41929(19) 0.33855(16) 0.0670(5) Uani 1 1 d . . . . .
O3 O 0.45582(15) 0.38618(17) 0.18797(16) 0.0695(5) Uani 1 1 d . . . . .
O1 O 0.32046(15) 0.6022(3) 0.27389(18) 0.0880(7) Uani 1 1 d . . . . .
C8 C 0.50993(16) 0.6006(2) 0.30669(16) 0.0411(5) Uani 1 1 d . . . . .
C10 C 0.71464(16) 0.5683(2) 0.36144(15) 0.0406(5) Uani 1 1 d . . . . .
C15 C 0.80090(18) 0.6573(2) 0.36766(17) 0.0472(5) Uani 1 1 d . . . . .
H15 H 0.7899 0.7491 0.3759 0.057 Uiso 1 1 calc R U . . .
C11 C 0.73268(17) 0.4311(2) 0.34982(16) 0.0441(5) Uani 1 1 d . . . . .
H11 H 0.6761 0.3703 0.3457 0.053 Uiso 1 1 calc R U . . .
C9 C 0.60728(18) 0.6189(2) 0.37251(16) 0.0437(5) Uani 1 1 d . . . . .
C14 C 0.90216(19) 0.6119(2) 0.36181(18) 0.0492(6) Uani 1 1 d . . . . .
H14 H 0.9589 0.6724 0.3662 0.059 Uiso 1 1 calc R U . . .
C12 C 0.83340(18) 0.3847(2) 0.34438(18) 0.0492(6) Uani 1 1 d . . . . .
H12 H 0.8448 0.2927 0.3374 0.059 Uiso 1 1 calc R U . . .
C13 C 0.91845(17) 0.4751(2) 0.34926(17) 0.0463(5) Uani 1 1 d . . . . .
C7 C 0.4052(2) 0.6415(3) 0.3291(2) 0.0562(6) Uani 1 1 d . . . . .
C5 C 0.4040(2) 0.7335(3) 0.4180(2) 0.0580(6) Uani 1 1 d . . . . .
C17 C 0.4105(2) 0.6164(3) 0.0913(2) 0.0647(7) Uani 1 1 d . . . . .
H17A H 0.4340 0.7088 0.0963 0.097 Uiso 1 1 calc R U . . .
H17B H 0.3396 0.6107 0.1058 0.097 Uiso 1 1 calc R U . . .
H17C H 0.4090 0.5835 0.0218 0.097 Uiso 1 1 calc R U . . .
C6 C 0.4960(3) 0.7661(3) 0.49272(19) 0.0675(8) Uani 1 1 d . . . . .
C4 C 0.3051(3) 0.7907(3) 0.4270(3) 0.0763(9) Uani 1 1 d . . . . .
H4 H 0.2430 0.7714 0.3772 0.092 Uiso 1 1 calc R U . . .
C16 C 1.1074(2) 0.5039(3) 0.3531(2) 0.0754(9) Uani 1 1 d . . . . .
H16A H 1.0932 0.5796 0.3064 0.113 Uiso 1 1 calc R U . . .
H16B H 1.1671 0.4532 0.3387 0.113 Uiso 1 1 calc R U . . .
H16C H 1.1245 0.5356 0.4242 0.113 Uiso 1 1 calc R U . . .
C3 C 0.2998(4) 0.8748(4) 0.5093(3) 0.0959(13) Uani 1 1 d . . . . .
H3 H 0.2338 0.9111 0.5152 0.115 Uiso 1 1 calc R U . . .
C1 C 0.4896(3) 0.8523(4) 0.5765(2) 0.0976(12) Uani 1 1 d . . . . .
H1 H 0.5509 0.8728 0.6269 0.117 Uiso 1 1 calc R U . . .
C2 C 0.3906(4) 0.9062(4) 0.5828(3) 0.1122(16) Uani 1 1 d . . . . .
H2 H 0.3855 0.9642 0.6376 0.135 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
S2 O3 1.4314(18) . ?
S2 O2 1.4316(17) . ?
S2 C17 1.760(2) . ?
S2 C8 1.797(2) . ?
S1 C9 1.728(2) . ?
S1 C6 1.739(3) . ?
O004 C13 1.368(3) . ?
O004 C16 1.430(3) . ?
O1 C7 1.225(3) . ?
C8 C9 1.361(3) . ?
C8 C7 1.476(3) . ?
C10 C11 1.392(3) . ?
C10 C15 1.394(3) . ?
C10 C9 1.487(3) . ?
C15 C14 1.379(3) . ?
C15 H15 0.9300 . ?
C11 C12 1.374(3) . ?
C11 H11 0.9300 . ?
C14 C13 1.386(3) . ?
C14 H14 0.9300 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9300 . ?
C7 C5 1.479(4) . ?
C5 C6 1.393(4) . ?
C5 C4 1.405(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C6 C1 1.403(4) . ?
C4 C3 1.372(5) . ?
C4 H4 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C3 C2 1.372(6) . ?
C3 H3 0.9300 . ?
C1 C2 1.384(5) . ?
C1 H1 0.9300 . ?
C2 H2 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
O3 S2 O2 117.24(11) . . ?
O3 S2 C17 109.45(12) . . ?
O2 S2 C17 106.20(13) . . ?
O3 S2 C8 108.85(11) . . ?
O2 S2 C8 108.77(10) . . ?
C17 S2 C8 105.73(11) . . ?
C9 S1 C6 104.53(12) . . ?
C13 O004 C16 118.5(2) . . ?
C9 C8 C7 125.0(2) . . ?
C9 C8 S2 120.74(16) . . ?
C7 C8 S2 114.21(16) . . ?
C11 C10 C15 118.6(2) . . ?
C11 C10 C9 121.00(19) . . ?
C15 C10 C9 120.34(19) . . ?
C14 C15 C10 121.3(2) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C8 C9 C10 128.49(19) . . ?
C8 C9 S1 123.29(17) . . ?
C10 C9 S1 108.13(15) . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
O004 C13 C14 124.4(2) . . ?
O004 C13 C12 115.6(2) . . ?
C14 C13 C12 120.0(2) . . ?
O1 C7 C8 120.8(2) . . ?
O1 C7 C5 120.3(2) . . ?
C8 C7 C5 118.8(2) . . ?
C6 C5 C4 118.7(3) . . ?
C6 C5 C7 123.2(2) . . ?
C4 C5 C7 118.1(3) . . ?
S2 C17 H17A 109.5 . . ?
S2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C6 C1 120.7(3) . . ?
C5 C6 S1 123.35(19) . . ?
C1 C6 S1 116.0(3) . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
O004 C16 H16A 109.5 . . ?
O004 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O004 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C2 C1 C6 118.9(4) . . ?
C2 C1 H1 120.6 . . ?
C6 C1 H1 120.6 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 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
O3 S2 C8 C9 107.19(19) . . . . ?
O2 S2 C8 C9 -21.6(2) . . . . ?
C17 S2 C8 C9 -135.3(2) . . . . ?
O3 S2 C8 C7 -71.58(19) . . . . ?
O2 S2 C8 C7 159.61(17) . . . . ?
C17 S2 C8 C7 45.9(2) . . . . ?
C11 C10 C15 C14 0.5(3) . . . . ?
C9 C10 C15 C14 177.38(19) . . . . ?
C15 C10 C11 C12 -0.2(3) . . . . ?
C9 C10 C11 C12 -177.06(19) . . . . ?
C7 C8 C9 C10 172.8(2) . . . . ?
S2 C8 C9 C10 -5.8(3) . . . . ?
C7 C8 C9 S1 -3.3(3) . . . . ?
S2 C8 C9 S1 178.07(12) . . . . ?
C11 C10 C9 C8 -56.4(3) . . . . ?
C15 C10 C9 C8 126.7(2) . . . . ?
C11 C10 C9 S1 120.18(19) . . . . ?
C15 C10 C9 S1 -56.7(2) . . . . ?
C6 S1 C9 C8 -7.1(2) . . . . ?
C6 S1 C9 C10 176.15(16) . . . . ?
C10 C15 C14 C13 0.1(3) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C16 O004 C13 C14 7.6(3) . . . . ?
C16 O004 C13 C12 -173.9(2) . . . . ?
C15 C14 C13 O004 177.4(2) . . . . ?
C15 C14 C13 C12 -1.0(3) . . . . ?
C11 C12 C13 O004 -177.2(2) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
C9 C8 C7 O1 -168.0(3) . . . . ?
S2 C8 C7 O1 10.7(3) . . . . ?
C9 C8 C7 C5 13.4(3) . . . . ?
S2 C8 C7 C5 -167.88(18) . . . . ?
O1 C7 C5 C6 170.2(3) . . . . ?
C8 C7 C5 C6 -11.2(4) . . . . ?
O1 C7 C5 C4 -9.8(4) . . . . ?
C8 C7 C5 C4 168.8(2) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C7 C5 C6 C1 -178.9(3) . . . . ?
C4 C5 C6 S1 179.5(2) . . . . ?
C7 C5 C6 S1 -0.5(4) . . . . ?
C9 S1 C6 C5 8.9(3) . . . . ?
C9 S1 C6 C1 -172.7(2) . . . . ?
C6 C5 C4 C3 -1.1(4) . . . . ?
C7 C5 C4 C3 178.9(3) . . . . ?
C5 C4 C3 C2 0.9(5) . . . . ?
C5 C6 C1 C2 -1.0(5) . . . . ?
S1 C6 C1 C2 -179.4(3) . . . . ?
C4 C3 C2 C1 -0.7(6) . . . . ?
C6 C1 C2 C3 0.7(6) . . . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.040

