# Supplementary Information (SI) for ChemComm.
# 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_2f
_database_code_depnum_ccdc_archive 'CCDC 2386775'
loop_
_audit_author_name
_audit_author_address
'Marcos Lopez Aguilar'
;Universidad de Oviedo
Spain
;
_audit_update_record             
;
2024-09-25 deposited with the CCDC.	2024-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
trans,cis-4-Hydroxyhexahydrobenzo[d][1,3]dithiolane-2-thione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 O2 S6'
_chemical_formula_weight         412.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.5479(4)
_cell_length_b                   11.0961(8)
_cell_length_c                   12.0292(8)
_cell_angle_alpha                103.921(6)
_cell_angle_beta                 97.793(5)
_cell_angle_gamma                98.661(5)
_cell_volume                     951.10(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3621
_cell_measurement_theta_min      3.8140
_cell_measurement_theta_max      69.3230

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.135
_exptl_absorpt_coefficient_mu    6.666
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.46723
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10237
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.848
_diffrn_reflns_theta_max         69.523
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3533
_reflns_number_gt                2668
_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       
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_computing_cell_refinement       
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_computing_data_reduction        
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_computing_structure_solution    'SIR-2019 (Giacovazzo, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'MERCURY (Cambridge Crystallographic Data Centre: Cambridge, UK, 2024)'
_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)+(0.0831P)²+0.2538P] 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         3533
_refine_ls_number_parameters     281
_refine_ls_number_restraints     98
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1629
_refine_ls_wR_factor_gt          0.1470
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.053
_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
C1 C -0.0040(5) 0.7970(3) 1.4440(3) 0.0794(9) Uani 1 1 d . . . . .
C2 C -0.3146(4) 0.8433(3) 1.3493(3) 0.0747(8) Uani 1 1 d . . . . .
H2A H -0.3049 0.9283 1.4004 0.090 Uiso 1 1 calc R U . . .
C3 C -0.5091(5) 0.8001(5) 1.2858(4) 0.0922(11) Uani 1 1 d . . . . .
H3A H -0.5242 0.7155 1.2348 0.111 Uiso 1 1 calc R U . . .
H3B H -0.5903 0.7974 1.3414 0.111 Uiso 1 1 calc R U . . .
C4 C -0.5566(5) 0.8896(5) 1.2151(4) 0.1051(13) Uani 1 1 d . . . . .
H4A H -0.6766 0.8555 1.1677 0.126 Uiso 1 1 calc R U . . .
H4B H -0.5618 0.9700 1.2675 0.126 Uiso 1 1 calc R U . . .
C5 C -0.4226(5) 0.9114(5) 1.1377(4) 0.0934(11) Uani 1 1 d . . . . .
H5A H -0.4506 0.9785 1.1034 0.112 Uiso 1 1 calc R U . . .
H5B H -0.4373 0.8352 1.0747 0.112 Uiso 1 1 calc R U . . .
C6 C -0.2255(5) 0.9465(4) 1.1988(3) 0.0825(9) Uani 1 1 d . . . . .
H6 H -0.2065 1.0304 1.2535 0.099 Uiso 1 1 calc R U . . .
C7 C -0.1855(4) 0.8533(3) 1.2667(3) 0.0711(7) Uani 1 1 d . . . . .
H7 H -0.2043 0.7702 1.2106 0.085 Uiso 1 1 calc R U . . .
C8 C 0.1310(5) 0.5761(4) 0.8838(3) 0.0809(9) Uani 1 1 d . . . . .
C9 C -0.120(3) 0.6976(18) 0.827(2) 0.074(6) Uani 0.536(8) 1 d D U P A 1
H9 H -0.0589 0.7330 0.7715 0.089 Uiso 0.536(8) 1 calc R U P A 1
C10 C -0.2783(9) 0.7622(6) 0.8442(7) 0.0666(16) Uani 0.536(8) 1 d D U P A 1
H10 H -0.3430 0.7262 0.8975 0.080 Uiso 0.536(8) 1 calc R U P A 1
C11 C -0.412(3) 0.7399(17) 0.7318(18) 0.077(4) Uani 0.536(8) 1 d D U P A 1
H11A H -0.5194 0.7734 0.7499 0.092 Uiso 0.536(8) 1 calc R U P A 1
H11B H -0.3570 0.7866 0.6827 0.092 Uiso 0.536(8) 1 calc R U P A 1
C12 C -0.470(2) 0.6028(13) 0.6649(13) 0.098(7) Uani 0.536(8) 1 d D U P A 1
H12A H -0.5514 0.5606 0.7055 0.118 Uiso 0.536(8) 1 calc R U P A 1
H12B H -0.5383 0.5979 0.5890 0.118 Uiso 0.536(8) 1 calc R U P A 1
C13 C -0.3158(13) 0.5330(7) 0.6480(7) 0.082(2) Uani 0.536(8) 1 d D U P A 1
H13A H -0.2474 0.5611 0.5932 0.099 Uiso 0.536(8) 1 calc R U P A 1
H13B H -0.3619 0.4428 0.6184 0.099 Uiso 0.536(8) 1 calc R U P A 1
C14 C -0.197(2) 0.5622(19) 0.7657(14) 0.073(4) Uani 0.536(8) 1 d D U P A 1
H14 H -0.2709 0.5286 0.8163 0.087 Uiso 0.536(8) 1 calc R U P A 1
O2 O -0.214(2) 0.8923(11) 0.8985(11) 0.070(3) Uani 0.536(8) 1 d D . P A 1
H2 H -0.1028 0.9076 0.9095 0.105 Uiso 0.536(8) 1 calc R U P A 1
S4 S 0.0492(4) 0.7106(2) 0.9455(3) 0.0814(11) Uani 0.536(8) 1 d . U P A 1
S6 S 0.0025(7) 0.4788(4) 0.7594(4) 0.0944(11) Uani 0.536(8) 1 d . U P A 1
C9A C -0.147(4) 0.685(2) 0.827(2) 0.063(5) Uani 0.464(8) 1 d D U P A 2
H9A H -0.2069 0.6700 0.8904 0.075 Uiso 0.464(8) 1 calc R U P A 2
C10A C -0.2288(10) 0.7876(6) 0.7896(7) 0.0634(18) Uani 0.464(8) 1 d D U P A 2
H10A H -0.1786 0.8003 0.7214 0.076 Uiso 0.464(8) 1 calc R U P A 2
C11A C -0.431(3) 0.738(2) 0.749(2) 0.085(7) Uani 0.464(8) 1 d D U P A 2
H11C H -0.4868 0.7344 0.8171 0.102 Uiso 0.464(8) 1 calc R U P A 2
H11D H -0.4835 0.7971 0.7137 0.102 Uiso 0.464(8) 1 calc R U P A 2
C12A C -0.480(2) 0.6088(17) 0.6642(14) 0.083(6) Uani 0.464(8) 1 d D U P A 2
H12C H -0.4509 0.6158 0.5895 0.099 Uiso 0.464(8) 1 calc R U P A 2
H12D H -0.6099 0.5782 0.6534 0.099 Uiso 0.464(8) 1 calc R U P A 2
C13A C -0.3800(12) 0.5141(8) 0.7038(9) 0.079(2) Uani 0.464(8) 1 d D U P A 2
H13C H -0.4041 0.4370 0.6410 0.095 Uiso 0.464(8) 1 calc R U P A 2
H13D H -0.4293 0.4937 0.7689 0.095 Uiso 0.464(8) 1 calc R U P A 2
C14A C -0.175(2) 0.558(2) 0.7407(18) 0.071(5) Uani 0.464(8) 1 d D U P A 2
H14A H -0.1259 0.5705 0.6720 0.085 Uiso 0.464(8) 1 calc R U P A 2
S4A S 0.0986(4) 0.7322(2) 0.8902(4) 0.0776(10) Uani 0.464(8) 1 d . U P A 2
S6A S -0.0502(6) 0.4617(4) 0.7987(5) 0.0887(10) Uani 0.464(8) 1 d . U P A 2
O2A O -0.200(3) 0.9082(14) 0.8710(13) 0.078(4) Uani 0.464(8) 1 d D . P A 2
H2A1 H -0.1383 0.9068 0.9320 0.117 Uiso 0.464(8) 1 calc R U P A 2
O1 O -0.1041(4) 0.9511(3) 1.1194(3) 0.1047(9) Uani 1 1 d . . . . .
H1 H -0.1257 1.0027 1.0832 0.157 Uiso 1 1 calc R U . . .
S1 S -0.23373(13) 0.74669(11) 1.43871(9) 0.0916(3) Uani 1 1 d . . . . .
S2 S 0.15370(16) 0.76053(12) 1.53104(9) 0.1047(4) Uani 1 1 d . . . . .
S3 S 0.04382(11) 0.88454(9) 1.34787(8) 0.0813(3) Uani 1 1 d . . . . .
S5 S 0.31694(15) 0.54281(13) 0.94740(11) 0.1096(4) 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 S2 1.640(3) . ?
C1 S3 1.720(4) . ?
C1 S1 1.727(4) . ?
C2 C7 1.495(5) . ?
C2 C3 1.509(5) . ?
C2 S1 1.803(3) . ?
C2 H2A 0.9800 . ?
C3 C4 1.506(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.497(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.516(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O1 1.414(4) . ?
C6 C7 1.503(5) . ?
C6 H6 0.9800 . ?
C7 S3 1.808(3) . ?
C7 H7 0.9800 . ?
C8 S5 1.641(3) . ?
C8 S6 1.691(5) . ?
C8 S6A 1.733(6) . ?
C8 S4 1.740(4) . ?
C8 S4A 1.770(4) . ?
C9 C14 1.492(16) . ?
C9 C10 1.498(16) . ?
C9 S4 1.74(2) . ?
C9 H9 0.9800 . ?
C10 O2 1.412(12) . ?
C10 C11 1.517(16) . ?
C10 H10 0.9800 . ?
C11 C12 1.506(13) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.503(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.504(14) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 S6 1.881(19) . ?
C14 H14 0.9800 . ?
O2 H2 0.8200 . ?
C9A C10A 1.500(15) . ?
C9A C14A 1.503(16) . ?
C9A S4A 1.85(3) . ?
C9A H9A 0.9800 . ?
C10A O2A 1.422(15) . ?
C10A C11A 1.514(17) . ?
C10A H10A 0.9800 . ?
C11A C12A 1.506(16) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C12A C13A 1.511(14) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C13A C14A 1.522(16) . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C14A S6A 1.73(3) . ?
C14A H14A 0.9800 . ?
O2A H2A1 0.8200 . ?
O1 H1 0.8200 . ?

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
S2 C1 S3 123.3(2) . . ?
S2 C1 S1 122.4(2) . . ?
S3 C1 S1 114.24(19) . . ?
C7 C2 C3 111.3(3) . . ?
C7 C2 S1 107.1(2) . . ?
C3 C2 S1 116.0(3) . . ?
C7 C2 H2A 107.4 . . ?
C3 C2 H2A 107.4 . . ?
S1 C2 H2A 107.4 . . ?
C4 C3 C2 109.9(3) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 112.8(3) . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C4 C5 C6 114.3(3) . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
O1 C6 C7 110.0(3) . . ?
O1 C6 C5 111.8(3) . . ?
C7 C6 C5 109.8(3) . . ?
O1 C6 H6 108.4 . . ?
C7 C6 H6 108.4 . . ?
C5 C6 H6 108.4 . . ?
C2 C7 C6 111.5(3) . . ?
C2 C7 S3 108.0(2) . . ?
C6 C7 S3 115.2(3) . . ?
C2 C7 H7 107.2 . . ?
C6 C7 H7 107.2 . . ?
S3 C7 H7 107.2 . . ?
S5 C8 S6 122.3(2) . . ?
S5 C8 S6A 123.3(3) . . ?
S5 C8 S4 121.4(2) . . ?
S6 C8 S4 116.3(2) . . ?
S5 C8 S4A 123.6(2) . . ?
S6A C8 S4A 113.1(2) . . ?
C14 C9 C10 106.7(17) . . ?
C14 C9 S4 110.8(12) . . ?
C10 C9 S4 119.6(14) . . ?
C14 C9 H9 106.3 . . ?
C10 C9 H9 106.3 . . ?
S4 C9 H9 106.3 . . ?
O2 C10 C9 109.6(12) . . ?
O2 C10 C11 112.1(10) . . ?
C9 C10 C11 112.4(13) . . ?
O2 C10 H10 107.5 . . ?
C9 C10 H10 107.5 . . ?
C11 C10 H10 107.5 . . ?
C12 C11 C10 113.9(14) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 114.5(12) . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C14 106.4(11) . . ?
C12 C13 H13A 110.5 . . ?
C14 C13 H13A 110.5 . . ?
C12 C13 H13B 110.5 . . ?
C14 C13 H13B 110.5 . . ?
H13A C13 H13B 108.6 . . ?
C9 C14 C13 117.8(17) . . ?
C9 C14 S6 106.2(11) . . ?
C13 C14 S6 111.5(11) . . ?
C9 C14 H14 106.9 . . ?
C13 C14 H14 106.9 . . ?
S6 C14 H14 106.9 . . ?
C10 O2 H2 109.5 . . ?
C8 S4 C9 96.3(5) . . ?
C8 S6 C14 95.3(5) . . ?
C10A C9A C14A 118.6(18) . . ?
C10A C9A S4A 114.3(16) . . ?
C14A C9A S4A 107.5(13) . . ?
C10A C9A H9A 105.0 . . ?
C14A C9A H9A 105.0 . . ?
S4A C9A H9A 105.0 . . ?
O2A C10A C9A 118.2(12) . . ?
O2A C10A C11A 109.3(14) . . ?
C9A C10A C11A 107.6(16) . . ?
O2A C10A H10A 107.1 . . ?
C9A C10A H10A 107.1 . . ?
C11A C10A H10A 107.1 . . ?
C12A C11A C10A 114.5(18) . . ?
C12A C11A H11C 108.6 . . ?
C10A C11A H11C 108.6 . . ?
C12A C11A H11D 108.6 . . ?
C10A C11A H11D 108.6 . . ?
H11C C11A H11D 107.6 . . ?
C11A C12A C13A 112.7(15) . . ?
C11A C12A H12C 109.1 . . ?
C13A C12A H12C 109.1 . . ?
C11A C12A H12D 109.1 . . ?
C13A C12A H12D 109.1 . . ?
H12C C12A H12D 107.8 . . ?
C12A C13A C14A 115.0(14) . . ?
C12A C13A H13C 108.5 . . ?
C14A C13A H13C 108.5 . . ?
C12A C13A H13D 108.5 . . ?
C14A C13A H13D 108.5 . . ?
H13C C13A H13D 107.5 . . ?
C9A C14A C13A 105.8(18) . . ?
C9A C14A S6A 109.8(13) . . ?
C13A C14A S6A 118.6(15) . . ?
C9A C14A H14A 107.4 . . ?
C13A C14A H14A 107.4 . . ?
S6A C14A H14A 107.4 . . ?
C8 S4A C9A 94.9(6) . . ?
C14A S6A C8 99.2(6) . . ?
C10A O2A H2A1 109.5 . . ?
C6 O1 H1 109.5 . . ?
C1 S1 C2 96.83(17) . . ?
C1 S3 C7 96.44(16) . . ?

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 -57.2(4) . . . . ?
S1 C2 C3 C4 -180.0(3) . . . . ?
C2 C3 C4 C5 52.1(6) . . . . ?
C3 C4 C5 C6 -50.3(6) . . . . ?
C4 C5 C6 O1 172.9(4) . . . . ?
C4 C5 C6 C7 50.6(5) . . . . ?
C3 C2 C7 C6 60.0(4) . . . . ?
S1 C2 C7 C6 -172.2(3) . . . . ?
C3 C2 C7 S3 -172.4(3) . . . . ?
S1 C2 C7 S3 -44.6(3) . . . . ?
O1 C6 C7 C2 -178.4(3) . . . . ?
C5 C6 C7 C2 -55.0(4) . . . . ?
O1 C6 C7 S3 58.0(4) . . . . ?
C5 C6 C7 S3 -178.5(3) . . . . ?
C14 C9 C10 O2 -178.2(14) . . . . ?
S4 C9 C10 O2 55(2) . . . . ?
C14 C9 C10 C11 -53(2) . . . . ?
S4 C9 C10 C11 -179.5(15) . . . . ?
O2 C10 C11 C12 174.4(15) . . . . ?
C9 C10 C11 C12 50(2) . . . . ?
C10 C11 C12 C13 -49(2) . . . . ?
C11 C12 C13 C14 49(2) . . . . ?
C10 C9 C14 C13 60(2) . . . . ?
S4 C9 C14 C13 -167.8(13) . . . . ?
C10 C9 C14 S6 -173.8(12) . . . . ?
S4 C9 C14 S6 -42.0(18) . . . . ?
C12 C13 C14 C9 -58(2) . . . . ?
C12 C13 C14 S6 179.1(11) . . . . ?
S5 C8 S4 C9 171.7(9) . . . . ?
S6 C8 S4 C9 -11.5(9) . . . . ?
S6A C8 S4 C9 -35.7(9) . . . . ?
S4A C8 S4 C9 68.1(9) . . . . ?
C14 C9 S4 C8 33.6(16) . . . . ?
C10 C9 S4 C8 158.4(15) . . . . ?
S5 C8 S6 C14 168.1(7) . . . . ?
S6A C8 S6 C14 67.9(8) . . . . ?
S4 C8 S6 C14 -8.7(7) . . . . ?
S4A C8 S6 C14 -38.5(7) . . . . ?
C9 C14 S6 C8 29.9(15) . . . . ?
C13 C14 S6 C8 159.5(12) . . . . ?
C14A C9A C10A O2A -179.5(18) . . . . ?
S4A C9A C10A O2A -51(2) . . . . ?
C14A C9A C10A C11A 56(3) . . . . ?
S4A C9A C10A C11A -175.3(15) . . . . ?
O2A C10A C11A C12A -178.9(17) . . . . ?
C9A C10A C11A C12A -49(2) . . . . ?
C10A C11A C12A C13A 49(3) . . . . ?
C11A C12A C13A C14A -51(2) . . . . ?
C10A C9A C14A C13A -56(3) . . . . ?
S4A C9A C14A C13A 171.9(14) . . . . ?
C10A C9A C14A S6A 174.4(17) . . . . ?
S4A C9A C14A S6A 42.8(19) . . . . ?
C12A C13A C14A C9A 51(2) . . . . ?
C12A C13A C14A S6A 174.8(11) . . . . ?
S5 C8 S4A C9A -169.4(8) . . . . ?
S6 C8 S4A C9A 37.6(8) . . . . ?
S6A C8 S4A C9A 13.0(8) . . . . ?
S4 C8 S4A C9A -74.4(8) . . . . ?
C10A C9A S4A C8 -167.1(13) . . . . ?
C14A C9A S4A C8 -33.1(16) . . . . ?
C9A C14A S6A C8 -31.4(17) . . . . ?
C13A C14A S6A C8 -153.1(12) . . . . ?
S5 C8 S6A C14A -170.0(8) . . . . ?
S6 C8 S6A C14A -74.8(9) . . . . ?
S4 C8 S6A C14A 38.0(8) . . . . ?
S4A C8 S6A C14A 7.6(8) . . . . ?
S2 C1 S1 C2 170.3(2) . . . . ?
S3 C1 S1 C2 -11.4(2) . . . . ?
C7 C2 S1 C1 34.3(3) . . . . ?
C3 C2 S1 C1 159.2(3) . . . . ?
S2 C1 S3 C7 168.0(2) . . . . ?
S1 C1 S3 C7 -10.3(2) . . . . ?
C2 C7 S3 C1 34.0(3) . . . . ?
C6 C7 S3 C1 159.3(3) . . . . ?

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_2g
_database_code_depnum_ccdc_archive 'CCDC 2386777'
loop_
_audit_author_name
_audit_author_address
'Marcos Lopez Aguilar'
;Universidad de Oviedo
Spain
;
_audit_update_record             
;
2024-09-25 deposited with the CCDC.	2024-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
trans,cis-4-(Benzyloxy)hexahydrobenzo[d][1,3]dithiolane-2-thione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 O S3'
_chemical_formula_weight         296.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.7687(3)
_cell_length_b                   8.3272(2)
_cell_length_c                   14.0444(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.571(3)
_cell_angle_gamma                90
_cell_volume                     1451.61(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5169
_cell_measurement_theta_min      3.5450
_cell_measurement_theta_max      69.3180

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.158
_exptl_absorpt_coefficient_mu    4.542
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.347
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10722
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.561
_diffrn_reflns_theta_max         69.429
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2709
_reflns_number_gt                2362
_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       
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_computing_cell_refinement       
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_computing_data_reduction        
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_computing_structure_solution    'SIR-2019 (Giacovazzo, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'MERCURY (Cambridge Crystallographic Data Centre: Cambridge, UK, 2024)'
_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)+(0.0626P)²+0.3416P] 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         2709
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
C1 C 0.42355(19) 0.0979(3) 0.7931(2) 0.0761(7) Uani 1 1 d . . . . .
C2 C 0.33309(17) 0.1020(3) 0.94400(16) 0.0605(5) Uani 1 1 d . . . . .
H2 H 0.334358 -0.014755 0.952918 0.073 Uiso 1 1 calc R U . . .
C3 C 0.24540(16) 0.1422(2) 0.85472(15) 0.0542(4) Uani 1 1 d . . . . .
H3 H 0.240745 0.259257 0.847915 0.065 Uiso 1 1 calc R U . . .
C4 C 0.13731(16) 0.0793(2) 0.86542(15) 0.0554(5) Uani 1 1 d . . . . .
H4 H 0.139944 -0.038068 0.870868 0.067 Uiso 1 1 calc R U . . .
C5 C 0.11327(19) 0.1516(3) 0.95787(18) 0.0680(6) Uani 1 1 d . . . . .
H5A H 0.103171 0.266537 0.949020 0.082 Uiso 1 1 calc R U . . .
H5B H 0.046635 0.106379 0.967807 0.082 Uiso 1 1 calc R U . . .
C6 C 0.2032(2) 0.1202(3) 1.04857(18) 0.0745(6) Uani 1 1 d . . . . .
H6A H 0.186328 0.173981 1.104384 0.089 Uiso 1 1 calc R U . . .
H6B H 0.207559 0.005876 1.062130 0.089 Uiso 1 1 calc R U . . .
C7 C 0.3117(2) 0.1793(3) 1.03557(17) 0.0739(6) Uani 1 1 d . . . . .
H7A H 0.310791 0.295242 1.029072 0.089 Uiso 1 1 calc R U . . .
H7B H 0.368053 0.150211 1.092216 0.089 Uiso 1 1 calc R U . . .
C8 C -0.04133(18) 0.0509(3) 0.76826(19) 0.0726(6) Uani 1 1 d . . . . .
H8A H -0.074107 0.086938 0.820213 0.087 Uiso 1 1 calc R U . . .
H8B H -0.032421 -0.064701 0.773668 0.087 Uiso 1 1 calc R U . . .
C9 C -0.11319(16) 0.0926(2) 0.67064(17) 0.0587(5) Uani 1 1 d . . . . .
C10 C -0.22337(18) 0.1035(3) 0.66223(19) 0.0667(5) Uani 1 1 d . . . . .
H10 H -0.250724 0.090810 0.717586 0.080 Uiso 1 1 calc R U . . .
C11 C -0.29270(18) 0.1329(3) 0.5730(2) 0.0734(6) Uani 1 1 d . . . . .
H11 H -0.366412 0.138971 0.568638 0.088 Uiso 1 1 calc R U . . .
C12 C -0.25425(19) 0.1532(3) 0.49078(19) 0.0711(6) Uani 1 1 d . . . . .
H12 H -0.301480 0.172847 0.430636 0.085 Uiso 1 1 calc R U . . .
C13 C -0.1447(2) 0.1443(3) 0.49776(19) 0.0699(6) Uani 1 1 d . . . . .
H13 H -0.117942 0.158441 0.442172 0.084 Uiso 1 1 calc R U . . .
C14 C -0.07449(17) 0.1143(3) 0.58733(18) 0.0640(5) Uani 1 1 d . . . . .
H14 H -0.000793 0.108767 0.591544 0.077 Uiso 1 1 calc R U . . .
O1 O 0.06048(11) 0.12496(18) 0.77854(11) 0.0619(4) Uani 1 1 d . . . . .
S1 S 0.45806(5) 0.16174(9) 0.91444(5) 0.0829(2) Uani 1 1 d . . . . .
S2 S 0.51057(7) 0.07549(15) 0.72596(7) 0.1188(4) Uani 1 1 d . . . . .
S3 S 0.28667(4) 0.06002(8) 0.74931(4) 0.0703(2) 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 S2 1.628(3) . ?
C1 S1 1.740(3) . ?
C1 S3 1.740(3) . ?
C2 C3 1.510(3) . ?
C2 C7 1.519(3) . ?
C2 S1 1.810(2) . ?
C2 H2 0.9800 . ?
C3 C4 1.516(3) . ?
C3 S3 1.818(2) . ?
C3 H3 0.9800 . ?
C4 O1 1.426(3) . ?
C4 C5 1.526(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.524(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.520(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.415(3) . ?
C8 C9 1.501(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.385(3) . ?
C9 C10 1.387(3) . ?
C10 C11 1.376(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.368(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9300 . ?
C14 H14 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
S2 C1 S1 123.50(16) . . ?
S2 C1 S3 122.65(18) . . ?
S1 C1 S3 113.86(13) . . ?
C3 C2 C7 111.32(19) . . ?
C3 C2 S1 105.69(14) . . ?
C7 C2 S1 114.92(16) . . ?
C3 C2 H2 108.2 . . ?
C7 C2 H2 108.2 . . ?
S1 C2 H2 108.2 . . ?
C2 C3 C4 110.86(16) . . ?
C2 C3 S3 107.03(14) . . ?
C4 C3 S3 113.28(14) . . ?
C2 C3 H3 108.5 . . ?
C4 C3 H3 108.5 . . ?
S3 C3 H3 108.5 . . ?
O1 C4 C3 106.40(15) . . ?
O1 C4 C5 112.78(17) . . ?
C3 C4 C5 108.50(18) . . ?
O1 C4 H4 109.7 . . ?
C3 C4 H4 109.7 . . ?
C5 C4 H4 109.7 . . ?
C6 C5 C4 112.38(19) . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 111.9(2) . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C2 C7 C6 108.3(2) . . ?
C2 C7 H7A 110.0 . . ?
C6 C7 H7A 110.0 . . ?
C2 C7 H7B 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
O1 C8 C9 110.02(18) . . ?
O1 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
O1 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C14 C9 C10 118.4(2) . . ?
C14 C9 C8 122.64(19) . . ?
C10 C9 C8 118.9(2) . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.5(2) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.5(2) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C8 O1 C4 113.70(16) . . ?
C1 S1 C2 96.10(11) . . ?
C1 S3 C3 95.89(11) . . ?

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 -61.5(2) . . . . ?
S1 C2 C3 C4 173.12(14) . . . . ?
C7 C2 C3 S3 174.55(15) . . . . ?
S1 C2 C3 S3 49.14(16) . . . . ?
C2 C3 C4 O1 179.26(16) . . . . ?
S3 C3 C4 O1 -60.40(18) . . . . ?
C2 C3 C4 C5 57.7(2) . . . . ?
S3 C3 C4 C5 177.99(14) . . . . ?
O1 C4 C5 C6 -172.56(18) . . . . ?
C3 C4 C5 C6 -54.9(2) . . . . ?
C4 C5 C6 C7 55.4(3) . . . . ?
C3 C2 C7 C6 58.5(3) . . . . ?
S1 C2 C7 C6 178.60(17) . . . . ?
C5 C6 C7 C2 -55.2(3) . . . . ?
O1 C8 C9 C14 33.9(3) . . . . ?
O1 C8 C9 C10 -148.8(2) . . . . ?
C14 C9 C10 C11 0.9(3) . . . . ?
C8 C9 C10 C11 -176.5(2) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C10 C9 C14 C13 -0.8(3) . . . . ?
C8 C9 C14 C13 176.5(2) . . . . ?
C12 C13 C14 C9 0.2(3) . . . . ?
C9 C8 O1 C4 -174.32(18) . . . . ?
C3 C4 O1 C8 169.10(18) . . . . ?
C5 C4 O1 C8 -72.1(2) . . . . ?
S2 C1 S1 C2 -164.97(18) . . . . ?
S3 C1 S1 C2 15.14(16) . . . . ?
C3 C2 S1 C1 -39.14(17) . . . . ?
C7 C2 S1 C1 -162.30(18) . . . . ?
S2 C1 S3 C3 -171.04(17) . . . . ?
S1 C1 S3 C3 8.85(16) . . . . ?
C2 C3 S3 C1 -35.81(16) . . . . ?
C4 C3 S3 C1 -158.29(15) . . . . ?

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.043



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2386776'
loop_
_audit_author_name
_audit_author_address
'Marcos Lopez Aguilar'
;Universidad de Oviedo
Spain
;
_audit_update_record             
;
2024-09-25 deposited with the CCDC.	2024-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        trans-(Cyclohexane-1,2-diyl)-dibenzothioate
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 O2 S2'
_chemical_formula_weight         356.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   23.7180(5)
_cell_length_b                   5.87190(10)
_cell_length_c                   27.5681(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.489(2)
_cell_angle_gamma                90
_cell_volume                     3681.50(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    12169
_cell_measurement_theta_min      3.3080
_cell_measurement_theta_max      69.5330

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.177
_exptl_absorpt_coefficient_mu    2.686
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15871
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.344
_diffrn_reflns_theta_max         69.648
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3431
_reflns_number_gt                3226
_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       
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_computing_cell_refinement       
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_computing_data_reduction        
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_computing_structure_solution    'SIR-2019 (Giacovazzo, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'MERCURY (Cambridge Crystallographic Data Centre: Cambridge, UK, 2024)'
_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)+(0.0617P)²+1.2612P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00046(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3431
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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 0.21079(6) -0.2081(2) 0.05613(5) 0.0456(3) Uani 1 1 d . . . . .
C2 C 0.17977(7) -0.4113(3) 0.04659(7) 0.0568(4) Uani 1 1 d . . . . .
H2 H 0.184902 -0.520114 0.071987 0.068 Uiso 1 1 calc R U . . .
C3 C 0.14130(8) -0.4521(3) -0.00052(7) 0.0671(5) Uani 1 1 d . . . . .
H3 H 0.120369 -0.588111 -0.006683 0.080 Uiso 1 1 calc R U . . .
C4 C 0.13370(8) -0.2919(3) -0.03862(7) 0.0654(5) Uani 1 1 d . . . . .
H4 H 0.108009 -0.320615 -0.070417 0.078 Uiso 1 1 calc R U . . .
C5 C 0.16431(8) -0.0896(3) -0.02930(6) 0.0617(4) Uani 1 1 d . . . . .
H5 H 0.159034 0.018781 -0.054797 0.074 Uiso 1 1 calc R U . . .
C6 C 0.20280(7) -0.0474(3) 0.01776(6) 0.0530(4) Uani 1 1 d . . . . .
H6 H 0.223470 0.089210 0.023818 0.064 Uiso 1 1 calc R U . . .
C7 C 0.25266(6) -0.1744(3) 0.10740(5) 0.0470(3) Uani 1 1 d . . . . .
C8 C 0.32687(6) 0.0717(3) 0.18451(5) 0.0477(3) Uani 1 1 d . . . . .
H8 H 0.345644 -0.078476 0.188128 0.057 Uiso 1 1 calc R U . . .
C9 C 0.28957(8) 0.0887(3) 0.22117(7) 0.0624(4) Uani 1 1 d . . . . .
H9A H 0.268957 0.233324 0.216339 0.075 Uiso 1 1 calc R U . . .
H9B H 0.260429 -0.031892 0.214006 0.075 Uiso 1 1 calc R U . . .
C10 C 0.32709(9) 0.0697(4) 0.27568(7) 0.0727(5) Uani 1 1 d . . . . .
H10A H 0.302417 0.085624 0.298162 0.087 Uiso 1 1 calc R U . . .
H10B H 0.345494 -0.079244 0.281294 0.087 Uiso 1 1 calc R U . . .
C11 C 0.37400(10) 0.2525(4) 0.28742(7) 0.0774(6) Uani 1 1 d . . . . .
H11A H 0.398627 0.234473 0.321903 0.093 Uiso 1 1 calc R U . . .
H11B H 0.355535 0.401233 0.284575 0.093 Uiso 1 1 calc R U . . .
C12 C 0.41177(8) 0.2381(4) 0.25126(7) 0.0653(5) Uani 1 1 d . . . . .
H12A H 0.432963 0.094768 0.256370 0.078 Uiso 1 1 calc R U . . .
H12B H 0.440442 0.360402 0.258606 0.078 Uiso 1 1 calc R U . . .
C13 C 0.37468(7) 0.2553(3) 0.19616(6) 0.0490(3) Uani 1 1 d . . . . .
H13 H 0.356010 0.405670 0.190417 0.059 Uiso 1 1 calc R U . . .
C14 C 0.44969(7) 0.4974(3) 0.15543(6) 0.0524(4) Uani 1 1 d . . . . .
C15 C 0.49296(7) 0.5253(3) 0.12576(6) 0.0534(4) Uani 1 1 d . . . . .
C16 C 0.49914(9) 0.3670(4) 0.09058(7) 0.0677(5) Uani 1 1 d . . . . .
H16 H 0.475594 0.237519 0.084469 0.081 Uiso 1 1 calc R U . . .
C17 C 0.54029(11) 0.4007(5) 0.06445(9) 0.0855(6) Uani 1 1 d . . . . .
H17 H 0.544283 0.294512 0.040624 0.103 Uiso 1 1 calc R U . . .
C18 C 0.57541(11) 0.5922(5) 0.07376(10) 0.0915(7) Uani 1 1 d . . . . .
H18 H 0.603447 0.614112 0.056488 0.110 Uiso 1 1 calc R U . . .
C19 C 0.56906(11) 0.7499(4) 0.10837(11) 0.0910(7) Uani 1 1 d . . . . .
H19 H 0.592641 0.879259 0.114328 0.109 Uiso 1 1 calc R U . . .
C20 C 0.52796(9) 0.7184(3) 0.13449(9) 0.0717(5) Uani 1 1 d . . . . .
H20 H 0.523751 0.826425 0.157888 0.086 Uiso 1 1 calc R U . . .
O1 O 0.26577(6) -0.3260(2) 0.13830(4) 0.0659(3) Uani 1 1 d . . . . .
O2 O 0.43666(7) 0.6511(2) 0.17921(6) 0.0801(4) Uani 1 1 d . . . . .
S1 S 0.28071(2) 0.10461(6) 0.11966(2) 0.05772(16) Uani 1 1 d . . . . .
S2 S 0.42115(2) 0.22028(7) 0.15435(2) 0.05795(16) 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 1.387(2) . ?
C1 C6 1.390(2) . ?
C1 C7 1.492(2) . ?
C2 C3 1.380(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.2101(19) . ?
C7 S1 1.7643(15) . ?
C8 C9 1.523(2) . ?
C8 C13 1.531(2) . ?
C8 S1 1.8226(15) . ?
C8 H8 0.9800 . ?
C9 C10 1.518(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.514(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.520(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.527(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 S2 1.8186(16) . ?
C13 H13 0.9800 . ?
C14 O2 1.206(2) . ?
C14 C15 1.492(2) . ?
C14 S2 1.7592(16) . ?
C15 C16 1.381(3) . ?
C15 C20 1.385(3) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(3) . ?
C19 H19 0.9300 . ?
C20 H20 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
C2 C1 C6 119.31(14) . . ?
C2 C1 C7 117.92(13) . . ?
C6 C1 C7 122.76(13) . . ?
C3 C2 C1 120.09(16) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.35(16) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.78(16) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.20(16) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.27(15) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O1 C7 C1 122.56(14) . . ?
O1 C7 S1 122.73(11) . . ?
C1 C7 S1 114.70(10) . . ?
C9 C8 C13 110.45(12) . . ?
C9 C8 S1 110.09(11) . . ?
C13 C8 S1 109.51(10) . . ?
C9 C8 H8 108.9 . . ?
C13 C8 H8 108.9 . . ?
S1 C8 H8 108.9 . . ?
C10 C9 C8 111.37(14) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 110.38(16) . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C12 110.77(16) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 111.60(15) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C8 110.19(13) . . ?
C12 C13 S2 109.95(11) . . ?
C8 C13 S2 109.46(10) . . ?
C12 C13 H13 109.1 . . ?
C8 C13 H13 109.1 . . ?
S2 C13 H13 109.1 . . ?
O2 C14 C15 122.53(15) . . ?
O2 C14 S2 122.99(13) . . ?
C15 C14 S2 114.45(12) . . ?
C16 C15 C20 119.68(17) . . ?
C16 C15 C14 122.52(16) . . ?
C20 C15 C14 117.80(16) . . ?
C15 C16 C17 120.1(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 119.9(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.5(2) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
C15 C20 H20 120.1 . . ?
C7 S1 C8 100.26(7) . . ?
C14 S2 C13 100.61(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
C6 C1 C2 C3 -0.2(2) . . . . ?
C7 C1 C2 C3 -178.87(16) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C7 C1 C6 C5 178.69(15) . . . . ?
C2 C1 C7 O1 9.4(2) . . . . ?
C6 C1 C7 O1 -169.25(16) . . . . ?
C2 C1 C7 S1 -169.82(12) . . . . ?
C6 C1 C7 S1 11.56(19) . . . . ?
C13 C8 C9 C10 -57.08(19) . . . . ?
S1 C8 C9 C10 -178.14(13) . . . . ?
C8 C9 C10 C11 57.5(2) . . . . ?
C9 C10 C11 C12 -56.8(2) . . . . ?
C10 C11 C12 C13 56.7(2) . . . . ?
C11 C12 C13 C8 -55.9(2) . . . . ?
C11 C12 C13 S2 -176.62(14) . . . . ?
C9 C8 C13 C12 55.60(18) . . . . ?
S1 C8 C13 C12 177.00(12) . . . . ?
C9 C8 C13 S2 176.63(11) . . . . ?
S1 C8 C13 S2 -61.97(12) . . . . ?
O2 C14 C15 C16 -166.41(18) . . . . ?
S2 C14 C15 C16 15.4(2) . . . . ?
O2 C14 C15 C20 13.8(2) . . . . ?
S2 C14 C15 C20 -164.39(14) . . . . ?
C20 C15 C16 C17 0.3(3) . . . . ?
C14 C15 C16 C17 -179.48(18) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C17 C18 C19 C20 0.5(4) . . . . ?
C18 C19 C20 C15 0.2(4) . . . . ?
C16 C15 C20 C19 -0.6(3) . . . . ?
C14 C15 C20 C19 179.19(19) . . . . ?
O1 C7 S1 C8 -0.39(16) . . . . ?
C1 C7 S1 C8 178.80(11) . . . . ?
C9 C8 S1 C7 -81.81(12) . . . . ?
C13 C8 S1 C7 156.57(11) . . . . ?
O2 C14 S2 C13 -0.77(17) . . . . ?
C15 C14 S2 C13 177.38(11) . . . . ?
C12 C13 S2 C14 -82.00(13) . . . . ?
C8 C13 S2 C14 156.83(11) . . . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.041



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
