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#$Date: 2025-03-04 20:21:18 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298016 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/40/7134073.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7134073
loop_
_publ_author_name
'López-Aguilar, Marcos'
'Ríos-Lombardía, Nicolás'
'Gallegos, Miguel'
'Barrena-Espés, Daniel'
'García-Álvarez, Joaquín'
'Concellón, Carmen'
'Del Amo, Vicente'
_publ_section_title
;
 Organocatalytic CS₂ insertion into epoxides in neat
 conditions: a straightforward approach for the efficient synthesis of Di-
 and tri-thiocarbonates.
;
_journal_issue                   17
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3488
_journal_page_last               3491
_journal_paper_doi               10.1039/d4cc05154h
_journal_volume                  61
_journal_year                    2025
_chemical_formula_sum            'C20 H20 O2 S2'
_chemical_formula_weight         356.48
_chemical_name_systematic        trans-(Cyclohexane-1,2-diyl)-dibenzothioate
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-09-25 deposited with the CCDC.	2024-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.489(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.7180(5)
_cell_length_b                   5.87190(10)
_cell_length_c                   27.5681(5)
_cell_measurement_reflns_used    12169
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      69.5330
_cell_measurement_theta_min      3.3080
_cell_volume                     3681.50(13)
_computing_cell_refinement
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_computing_data_collection
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_computing_data_reduction
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_computing_molecular_graphics
'MERCURY (Cambridge Crystallographic Data Centre: Cambridge, UK, 2024)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SIR-2019 (Giacovazzo, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15871
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.648
_diffrn_reflns_theta_min         3.344
_exptl_absorpt_coefficient_mu    2.686
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_type   gaussian
_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_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       prism
_exptl_crystal_F_000             1504
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.177
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00046(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0617P)²+1.2612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3226
_reflns_number_total             3431
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc05154h3.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7134071--7134073.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7134073
_shelx_shelxl_version_number     2018/3
_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'
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 . . . . .
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'
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_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_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) . . . . ?
