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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/7/13/40/7134072.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_7134072
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            'C14 H16 O S3'
_chemical_formula_weight         296.45
_chemical_name_systematic
trans,cis-4-(Benzyloxy)hexahydrobenzo[d][1,3]dithiolane-2-thione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/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                 103.571(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7687(3)
_cell_length_b                   8.3272(2)
_cell_length_c                   14.0444(4)
_cell_measurement_reflns_used    5169
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      69.3180
_cell_measurement_theta_min      3.5450
_cell_volume                     1451.61(7)
_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 0.999
_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  0.0386
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10722
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.429
_diffrn_reflns_theta_min         3.561
_exptl_absorpt_coefficient_mu    4.542
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.347
_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 intense yellow'
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0626P)²+0.3416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1248
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2362
_reflns_number_total             2709
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc05154h3.cif
_cod_data_source_block           2g
_cod_depositor_comments
'Adding full bibliography for 7134071--7134073.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7134072
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.42355(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 . . . . .
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
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_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_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) . . . . ?
