# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_20191011LI_SZZ_HFE_12Z_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2025337'
loop_
_audit_author_name
_audit_author_address
'Jiefeng Hu'
;Nanjing University
China
;
_audit_update_record             
;
2020-08-25 deposited with the CCDC.	2021-01-18 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            'C20 H20 N O2 S2'
_chemical_formula_weight         370.49

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'
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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                   12.3021(11)
_cell_length_b                   7.9076(7)
_cell_length_c                   18.7346(17)
_cell_angle_alpha                90
_cell_angle_beta                 97.095(3)
_cell_angle_gamma                90
_cell_volume                     1808.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    5215
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             780
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.308
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6488
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14733
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.106
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4132
_reflns_number_gt                3112
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0473P)²+1.5676P] 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         4132
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1209
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
S1 S 0.52055(6) 0.30006(9) 0.60265(4) 0.03561(19) Uani 1 1 d . . . . .
S2 S 1.05450(5) 0.68587(8) 0.59645(3) 0.02871(17) Uani 1 1 d . . . . .
O1 O 1.03554(15) 0.7342(2) 0.52214(9) 0.0341(4) Uani 1 1 d . . . . .
O2 O 1.14769(15) 0.5811(2) 0.61915(11) 0.0389(5) Uani 1 1 d . . . . .
N14 N 0.94757(18) 0.5894(3) 0.62313(11) 0.0296(5) Uani 1 1 d . . . . .
H14 H 0.945266 0.564879 0.668731 0.036 Uiso 1 1 calc R U . . .
C1 C 0.4156(2) 0.2032(3) 0.54689(15) 0.0330(6) Uani 1 1 d . . . . .
C2 C 0.3186(2) 0.1377(4) 0.56636(17) 0.0416(7) Uani 1 1 d . . . . .
H2 H 0.302467 0.144326 0.614585 0.050 Uiso 1 1 calc R U . . .
C3 C 0.2468(2) 0.0631(4) 0.51381(18) 0.0463(8) Uani 1 1 d . . . . .
H3 H 0.180013 0.017750 0.525959 0.056 Uiso 1 1 calc R U . . .
C4 C 0.2698(2) 0.0525(4) 0.44333(18) 0.0428(7) Uani 1 1 d . . . . .
H4 H 0.218749 -0.000629 0.408170 0.051 Uiso 1 1 calc R U . . .
C5 C 0.3648(2) 0.1175(3) 0.42361(15) 0.0357(6) Uani 1 1 d . . . . .
H5 H 0.379620 0.109827 0.375143 0.043 Uiso 1 1 calc R U . . .
C6 C 0.4397(2) 0.1952(3) 0.47562(14) 0.0304(6) Uani 1 1 d . . . . .
C7 C 0.5417(2) 0.2741(3) 0.46807(14) 0.0310(6) Uani 1 1 d . . . . .
H7 H 0.569693 0.283630 0.423204 0.037 Uiso 1 1 calc R U . . .
C8 C 0.5956(2) 0.3346(3) 0.53065(14) 0.0297(6) Uani 1 1 d . . . . .
C9 C 0.6989(2) 0.4205(3) 0.53460(14) 0.0299(6) Uani 1 1 d . . . . .
H9 H 0.718616 0.455778 0.489455 0.036 Uiso 1 1 calc R U . . .
C10 C 0.7733(2) 0.4598(3) 0.59178(13) 0.0285(5) Uani 1 1 d . . . . .
C11 C 0.7656(2) 0.4125(3) 0.66857(14) 0.0347(6) Uani 1 1 d . . . . .
H11A H 0.839422 0.380947 0.691898 0.042 Uiso 1 1 calc R U . . .
H11B H 0.717894 0.311830 0.669380 0.042 Uiso 1 1 calc R U . . .
C12 C 0.7205(3) 0.5528(4) 0.71199(17) 0.0579(9) Uani 1 1 d . . . . .
H12A H 0.717393 0.513676 0.761317 0.087 Uiso 1 1 calc R U . . .
H12B H 0.646763 0.583297 0.689900 0.087 Uiso 1 1 calc R U . . .
H12C H 0.768457 0.651993 0.712722 0.087 Uiso 1 1 calc R U . . .
C13 C 0.8683(2) 0.5516(3) 0.57514(13) 0.0277(5) Uani 1 1 d . . . . .
H13 H 0.872019 0.585179 0.526816 0.033 Uiso 1 1 calc R U . . .
C17 C 1.0632(2) 0.8698(3) 0.64944(13) 0.0270(5) Uani 1 1 d . . . . .
C18 C 1.1123(2) 0.8633(3) 0.72009(15) 0.0370(6) Uani 1 1 d . . . . .
H18 H 1.137836 0.758849 0.740875 0.044 Uiso 1 1 calc R U . . .
C19 C 1.1236(2) 1.0108(4) 0.75987(14) 0.0380(7) Uani 1 1 d . . . . .
H19 H 1.157355 1.006929 0.808269 0.046 Uiso 1 1 calc R U . . .
C20 C 1.0866(2) 1.1648(3) 0.73045(14) 0.0312(6) Uani 1 1 d . . . . .
C21 C 1.0987(3) 1.3255(4) 0.77340(16) 0.0449(7) Uani 1 1 d . . . . .
H21A H 1.120348 1.417488 0.743047 0.067 Uiso 1 1 calc R U . . .
H21B H 1.155029 1.310336 0.814712 0.067 Uiso 1 1 calc R U . . .
H21C H 1.028783 1.353602 0.790481 0.067 Uiso 1 1 calc R U . . .
C22 C 1.0381(2) 1.1675(3) 0.65937(15) 0.0336(6) Uani 1 1 d . . . . .
H22 H 1.013363 1.271943 0.638171 0.040 Uiso 1 1 calc R U . . .
C23 C 1.0255(2) 1.0214(3) 0.61913(14) 0.0303(6) Uani 1 1 d . . . . .
H23 H 0.991066 1.024820 0.570882 0.036 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 C1 1.736(3) . ?
S1 C8 1.748(3) . ?
S2 O1 1.4347(18) . ?
S2 O2 1.4357(19) . ?
S2 N14 1.651(2) . ?
S2 C17 1.757(3) . ?
N14 C13 1.278(3) . ?
N14 H14 0.8800 . ?
C1 C2 1.390(4) . ?
C1 C6 1.405(4) . ?
C2 C3 1.371(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.424(4) . ?
C7 C8 1.361(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.435(4) . ?
C9 C10 1.356(3) . ?
C9 H9 0.9500 . ?
C10 C13 1.442(4) . ?
C10 C11 1.501(4) . ?
C11 C12 1.520(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C17 C23 1.382(3) . ?
C17 C18 1.386(4) . ?
C18 C19 1.382(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(4) . ?
C19 H19 0.9500 . ?
C20 C22 1.390(4) . ?
C20 C21 1.502(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.378(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

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
C1 S1 C8 91.68(13) . . ?
O1 S2 O2 117.98(12) . . ?
O1 S2 N14 112.13(11) . . ?
O2 S2 N14 106.31(11) . . ?
O1 S2 C17 108.61(11) . . ?
O2 S2 C17 108.65(12) . . ?
N14 S2 C17 101.93(12) . . ?
C13 N14 S2 117.57(19) . . ?
C13 N14 H14 121.2 . . ?
S2 N14 H14 121.2 . . ?
C2 C1 C6 121.4(3) . . ?
C2 C1 S1 127.3(2) . . ?
C6 C1 S1 111.3(2) . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 129.5(3) . . ?
C1 C6 C7 111.5(2) . . ?
C8 C7 C6 114.2(2) . . ?
C8 C7 H7 122.9 . . ?
C6 C7 H7 122.9 . . ?
C7 C8 C9 123.1(2) . . ?
C7 C8 S1 111.2(2) . . ?
C9 C8 S1 125.69(19) . . ?
C10 C9 C8 131.0(2) . . ?
C10 C9 H9 114.5 . . ?
C8 C9 H9 114.5 . . ?
C9 C10 C13 115.5(2) . . ?
C9 C10 C11 125.7(2) . . ?
C13 C10 C11 118.8(2) . . ?
C10 C11 C12 113.6(2) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N14 C13 C10 122.3(2) . . ?
N14 C13 H13 118.9 . . ?
C10 C13 H13 118.9 . . ?
C23 C17 C18 120.6(2) . . ?
C23 C17 S2 119.47(19) . . ?
C18 C17 S2 119.85(19) . . ?
C19 C18 C17 119.1(2) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 121.3(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C22 118.3(2) . . ?
C19 C20 C21 121.5(2) . . ?
C22 C20 C21 120.2(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 121.1(2) . . ?
C23 C22 H22 119.4 . . ?
C20 C22 H22 119.4 . . ?
C22 C23 C17 119.5(2) . . ?
C22 C23 H23 120.2 . . ?
C17 C23 H23 120.2 . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.061



