# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2023253'
loop_
_audit_author_name
_audit_author_address
'Guodong Yin'
;Hubei Normal University
China
;
_audit_update_record             
;
2020-08-14 deposited with the CCDC.	2020-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H30 S2'
_chemical_formula_weight         478.70

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P21/c   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.7800(10)
_cell_length_b                   12.5320(8)
_cell_length_c                   11.4990(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.22(2)
_cell_angle_gamma                90.00
_cell_volume                     1264.30(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1140
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      23.26

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9364
_exptl_absorpt_correction_T_max  0.9512
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6105
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_av_sigmaI/netI    0.0949
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2225
_reflns_number_gt                1262
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0100P)²+0.0700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2225
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.00912(9) 0.02116(7) 0.25604(6) 0.0642(3) Uani 1 1 d . . .
C1 C 0.4574(3) 0.4526(3) 0.3100(3) 0.0809(11) Uani 1 1 d . . .
H1A H 0.5017 0.4485 0.2351 0.121 Uiso 1 1 calc R . .
H1B H 0.5369 0.4587 0.3693 0.121 Uiso 1 1 calc R . .
H1C H 0.3922 0.5140 0.3125 0.121 Uiso 1 1 calc R . .
C2 C 0.3658(3) 0.3536(3) 0.3305(3) 0.0591(9) Uani 1 1 d . . .
C3 C 0.3508(3) 0.2746(3) 0.2478(3) 0.0635(9) Uani 1 1 d . . .
H3A H 0.4038 0.2803 0.1796 0.076 Uiso 1 1 calc R . .
C4 C 0.2594(3) 0.1876(3) 0.2640(2) 0.0602(9) Uani 1 1 d . . .
H4A H 0.2512 0.1360 0.2060 0.072 Uiso 1 1 calc R . .
C5 C 0.1793(3) 0.1743(3) 0.3639(2) 0.0493(8) Uani 1 1 d . . .
C6 C 0.1973(3) 0.2533(3) 0.4474(2) 0.0566(9) Uani 1 1 d . . .
H6A H 0.1452 0.2477 0.5160 0.068 Uiso 1 1 calc R . .
C7 C 0.2897(3) 0.3392(3) 0.4316(3) 0.0591(9) Uani 1 1 d . . .
H7A H 0.3015 0.3893 0.4909 0.071 Uiso 1 1 calc R . .
C8 C 0.0760(3) 0.0831(3) 0.3800(2) 0.0518(8) Uani 1 1 d . . .
C9 C 0.0509(3) 0.0418(2) 0.4859(2) 0.0536(9) Uani 1 1 d . . .
H9A H 0.1069 0.0716 0.5481 0.064 Uiso 1 1 calc R . .
C10 C -0.0993(3) 0.1264(3) 0.1776(2) 0.0526(8) Uani 1 1 d . . .
C11 C -0.1481(3) 0.1052(3) 0.0649(2) 0.0637(9) Uani 1 1 d . . .
H11A H -0.1235 0.0405 0.0309 0.076 Uiso 1 1 calc R . .
C12 C -0.2328(4) 0.1787(3) 0.0022(3) 0.0692(10) Uani 1 1 d . . .
H12A H -0.2662 0.1617 -0.0733 0.083 Uiso 1 1 calc R . .
C13 C -0.2701(3) 0.2765(3) 0.0469(3) 0.0573(9) Uani 1 1 d . . .
C14 C -0.2158(3) 0.2972(3) 0.1575(3) 0.0617(9) Uani 1 1 d . . .
H14A H -0.2353 0.3636 0.1899 0.074 Uiso 1 1 calc R . .
C15 C -0.1339(3) 0.2243(3) 0.2225(2) 0.0596(9) Uani 1 1 d . . .
H15A H -0.1014 0.2414 0.2982 0.072 Uiso 1 1 calc R . .
C16 C -0.3628(3) 0.3574(3) -0.0222(3) 0.0820(11) Uani 1 1 d . . .
H16A H -0.3901 0.3286 -0.0975 0.123 Uiso 1 1 calc R . .
H16B H -0.3037 0.4211 -0.0312 0.123 Uiso 1 1 calc R . .
H16C H -0.4536 0.3740 0.0180 0.123 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0892(6) 0.0557(6) 0.0473(5) -0.0021(4) -0.0047(4) -0.0010(5)
C1 0.078(2) 0.074(3) 0.091(3) 0.012(2) 0.0065(18) -0.006(2)
C2 0.0551(18) 0.059(2) 0.062(2) 0.010(2) -0.0042(17) 0.003(2)
C3 0.0605(19) 0.080(3) 0.051(2) 0.005(2) 0.0082(16) -0.002(2)
C4 0.0645(19) 0.072(2) 0.0440(18) -0.0053(18) 0.0017(15) -0.003(2)
C5 0.0568(17) 0.057(2) 0.0344(16) 0.0015(16) -0.0011(14) 0.0053(19)
C6 0.0647(18) 0.064(2) 0.0413(17) 0.0016(18) 0.0057(14) 0.003(2)
C7 0.070(2) 0.057(2) 0.0504(19) -0.0001(18) 0.0028(16) -0.001(2)
C8 0.0564(17) 0.056(2) 0.0435(17) 0.0041(16) 0.0002(14) 0.0020(18)
C9 0.0568(19) 0.059(2) 0.0443(17) -0.0017(17) -0.0021(14) 0.0026(18)
C10 0.0591(17) 0.058(2) 0.0404(17) 0.0017(16) -0.0030(14) -0.0071(19)
C11 0.083(2) 0.061(2) 0.0463(19) -0.0041(18) -0.0010(16) -0.011(2)
C12 0.086(2) 0.077(3) 0.0431(19) 0.010(2) -0.0141(17) -0.022(2)
C13 0.0561(18) 0.065(3) 0.050(2) 0.0115(19) -0.0039(15) -0.016(2)
C14 0.0606(18) 0.066(2) 0.058(2) -0.0024(19) -0.0066(15) 0.002(2)
C15 0.0661(19) 0.071(2) 0.0412(17) -0.0070(18) -0.0062(15) 0.006(2)
C16 0.072(2) 0.097(3) 0.075(2) 0.030(2) -0.0191(17) -0.012(2)

_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 C8 1.764(3) . ?
S1 C10 1.767(3) . ?
C1 C2 1.502(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.375(4) . ?
C2 C7 1.376(4) . ?
C3 C4 1.371(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.384(4) . ?
C5 C8 1.474(4) . ?
C6 C7 1.364(4) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.350(3) . ?
C9 C9 1.422(5) 3_556 ?
C9 H9A 0.9300 . ?
C10 C15 1.370(4) . ?
C10 C11 1.375(3) . ?
C11 C12 1.371(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.374(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.365(4) . ?
C13 C16 1.507(4) . ?
C14 C15 1.367(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C8 S1 C10 104.56(14) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 116.9(3) . . ?
C3 C2 C1 121.6(3) . . ?
C7 C2 C1 121.5(3) . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C3 C4 C5 121.9(3) . . ?
C3 C4 H4A 119.0 . . ?
C5 C4 H4A 119.0 . . ?
C4 C5 C6 116.3(3) . . ?
C4 C5 C8 122.3(3) . . ?
C6 C5 C8 121.4(3) . . ?
C7 C6 C5 121.7(3) . . ?
C7 C6 H6A 119.2 . . ?
C5 C6 H6A 119.2 . . ?
C6 C7 C2 121.8(3) . . ?
C6 C7 H7A 119.1 . . ?
C2 C7 H7A 119.1 . . ?
C9 C8 C5 122.3(2) . . ?
C9 C8 S1 118.8(2) . . ?
C5 C8 S1 118.9(2) . . ?
C8 C9 C9 127.9(3) . 3_556 ?
C8 C9 H9A 116.1 . . ?
C9 C9 H9A 116.1 3_556 . ?
C15 C10 C11 117.5(3) . . ?
C15 C10 S1 125.3(2) . . ?
C11 C10 S1 117.0(3) . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C13 122.3(3) . . ?
C11 C12 H12A 118.8 . . ?
C13 C12 H12A 118.8 . . ?
C14 C13 C12 116.0(3) . . ?
C14 C13 C16 121.7(3) . . ?
C12 C13 C16 122.3(3) . . ?
C13 C14 C15 122.7(3) . . ?
C13 C14 H14A 118.7 . . ?
C15 C14 H14A 118.7 . . ?
C14 C15 C10 120.8(3) . . ?
C14 C15 H15A 119.6 . . ?
C10 C15 H15A 119.6 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047
