# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2441924'
loop_
_audit_author_name
_audit_author_address
'Lei Hua'
;NingXia University
China
;
_audit_update_record             
;
2025-04-08 deposited with the CCDC.	2025-11-14 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            'C16 H16 S2'
_chemical_formula_weight         272.41

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.4800(13)
_cell_length_b                   7.981(2)
_cell_length_c                   33.787(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1477.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3675
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      23.22

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.341
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_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
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16429
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.411
_diffrn_reflns_theta_max         25.119
_diffrn_reflns_theta_full        25.119
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2623
_reflns_number_gt                1583
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.986

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0517P)²+0.9671P] 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_abs_structure_details 
;
 Flack x determined using 462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2623
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1287
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1421
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_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
C1 C 0.7125(14) 0.5985(9) 0.42846(18) 0.084(2) Uani 1 1 d . . . . .
H1A H 0.6590 0.5228 0.4082 0.126 Uiso 1 1 calc R U . . .
H1B H 0.8872 0.5953 0.4303 0.126 Uiso 1 1 calc R U . . .
H1C H 0.6608 0.7102 0.4221 0.126 Uiso 1 1 calc R U . . .
C2 C 0.6026(7) 0.5467(5) 0.46776(9) 0.0533(16) Uani 1 1 d G . . . .
C3 C 0.3849(7) 0.4574(5) 0.46889(9) 0.0581(17) Uani 1 1 d G . . . .
H3 H 0.3052 0.4301 0.4455 0.070 Uiso 1 1 calc R U . . .
C4 C 0.2863(6) 0.4090(5) 0.50503(12) 0.0558(16) Uani 1 1 d G . . . .
H4 H 0.1406 0.3493 0.5058 0.067 Uiso 1 1 calc R U . . .
C5 C 0.4054(7) 0.4499(5) 0.54005(9) 0.0499(16) Uani 1 1 d G . . . .
C6 C 0.6231(7) 0.5392(5) 0.53892(9) 0.0567(17) Uani 1 1 d G . . . .
H6 H 0.7028 0.5665 0.5623 0.068 Uiso 1 1 calc R U . . .
C7 C 0.7217(6) 0.5875(5) 0.50278(12) 0.0577(16) Uani 1 1 d G . . . .
H7 H 0.8673 0.6473 0.5020 0.069 Uiso 1 1 calc R U . . .
C8 C 0.4965(12) 0.3171(8) 0.61405(19) 0.0618(18) Uani 1 1 d . . . . .
H8 H 0.6538 0.3165 0.6037 0.074 Uiso 1 1 calc R U . . .
C9 C 0.4618(12) 0.2624(10) 0.65035(18) 0.0666(18) Uani 1 1 d . . . . .
H9 H 0.5964 0.2302 0.6653 0.080 Uiso 1 1 calc R U . . .
C10 C 0.2301(7) 0.2575(6) 0.72295(9) 0.0518(14) Uani 1 1 d G . . . .
C11 C 0.0653(6) 0.1746(5) 0.74732(13) 0.0618(18) Uani 1 1 d G . . . .
H11 H -0.0648 0.1161 0.7363 0.074 Uiso 1 1 calc R U . . .
C12 C 0.0948(8) 0.1791(5) 0.78817(12) 0.069(2) Uani 1 1 d G . . . .
H12 H -0.0155 0.1237 0.8045 0.083 Uiso 1 1 calc R U . . .
C13 C 0.2893(9) 0.2666(6) 0.80464(9) 0.0672(18) Uani 1 1 d G . . . .
C14 C 0.4542(7) 0.3495(5) 0.78027(13) 0.0658(19) Uani 1 1 d G . . . .
H14 H 0.5843 0.4080 0.7913 0.079 Uiso 1 1 calc R U . . .
C15 C 0.4246(7) 0.3449(5) 0.73943(13) 0.0612(18) Uani 1 1 d G . . . .
H15 H 0.5349 0.4004 0.7231 0.073 Uiso 1 1 calc R U . . .
C16 C 0.3292(16) 0.2689(11) 0.84945(19) 0.109(3) Uani 1 1 d . . . . .
H16A H 0.4889 0.2265 0.8554 0.163 Uiso 1 1 calc R U . . .
H16B H 0.2084 0.2000 0.8621 0.163 Uiso 1 1 calc R U . . .
H16C H 0.3151 0.3818 0.8590 0.163 Uiso 1 1 calc R U . . .
S1 S 0.2589(3) 0.3905(2) 0.58477(5) 0.0709(6) Uani 1 1 d . . . . .
S2 S 0.1731(3) 0.2480(3) 0.67141(5) 0.0771(6) Uani 1 1 d . . . . .


_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
C1 C2 1.515(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 S1 1.776(3) . ?
C6 C7 1.3900 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.316(8) . ?
C8 S1 1.737(7) . ?
C8 H8 0.9300 . ?
C9 S2 1.738(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.3900 . ?
C10 C15 1.3900 . ?
C10 S2 1.771(4) . ?
C11 C12 1.3900 . ?
C11 H11 0.9300 . ?
C12 C13 1.3900 . ?
C12 H12 0.9300 . ?
C13 C14 1.3900 . ?
C13 C16 1.530(7) . ?
C14 C15 1.3900 . ?
C14 H14 0.9300 . ?
C15 H15 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
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 120.0 . . ?
C3 C2 C1 120.3(4) . . ?
C7 C2 C1 119.7(4) . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 S1 116.7(2) . . ?
C6 C5 S1 123.3(2) . . ?
C5 C6 C7 120.0 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C9 C8 S1 122.3(5) . . ?
C9 C8 H8 118.9 . . ?
S1 C8 H8 118.9 . . ?
C8 C9 S2 122.4(5) . . ?
C8 C9 H9 118.8 . . ?
S2 C9 H9 118.8 . . ?
C11 C10 C15 120.0 . . ?
C11 C10 S2 116.6(3) . . ?
C15 C10 S2 123.4(3) . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 C16 119.2(5) . . ?
C12 C13 C16 120.8(5) . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 120.0 . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
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 . . ?
C8 S1 C5 103.6(3) . . ?
C9 S2 C10 103.8(3) . . ?

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
C7 C2 C3 C4 0.0 . . . . ?
C1 C2 C3 C4 179.4(4) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C3 C4 C5 S1 177.4(3) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
S1 C5 C6 C7 -177.3(3) . . . . ?
C5 C6 C7 C2 0.0 . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
C1 C2 C7 C6 -179.4(4) . . . . ?
S1 C8 C9 S2 3.5(9) . . . . ?
C15 C10 C11 C12 0.0 . . . . ?
S2 C10 C11 C12 -178.7(3) . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C11 C12 C13 C16 -178.2(5) . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C16 C13 C14 C15 178.3(5) . . . . ?
C13 C14 C15 C10 0.0 . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
S2 C10 C15 C14 178.6(3) . . . . ?
C9 C8 S1 C5 179.2(6) . . . . ?
C4 C5 S1 C8 138.6(3) . . . . ?
C6 C5 S1 C8 -44.0(3) . . . . ?
C8 C9 S2 C10 -155.9(6) . . . . ?
C11 C10 S2 C9 -150.9(3) . . . . ?
C15 C10 S2 C9 30.5(4) . . . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.045

