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#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/58/1545875.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_1545875
loop_
_publ_author_name
'Cerda, Matthew M.'
'Hammers, Matthew D.'
'Earp, Mary S.'
'Zakharov, Lev N.'
'Pluth, Michael D.'
_publ_section_title
;
 Applications of Synthetic Organic Tetrasulfides as H2S Donors.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2314
_journal_page_last               2317
_journal_paper_doi               10.1021/acs.orglett.7b00858
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C14 H14 S4'
_chemical_formula_weight         310.49
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.306(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0418(4)
_cell_length_b                   6.1192(2)
_cell_length_c                   17.3990(5)
_cell_measurement_reflns_used    3632
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.60
_cell_measurement_theta_min      3.21
_cell_volume                     1465.99(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker Apex-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8807
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        66.617
_diffrn_reflns_theta_max         66.617
_diffrn_reflns_theta_min         3.209
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    5.770
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       cut-block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0356
_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)+(0.0571P)²+0.5010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2213
_reflns_number_total             2535
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b00858_si_002.cif
_cod_data_source_block           cu_mplu44_0m
_cod_depositor_comments          'Adding full bibliography for 1545875.cif.'
_cod_database_code               1545875
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.596
_shelx_estimated_absorpt_t_max   0.802
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
S1 S 0.33318(4) 1.29751(12) 0.47911(4) 0.03027(18) Uani 1 1 d
S2 S 0.23583(4) 1.43490(11) 0.53927(4) 0.02892(18) Uani 1 1 d
S3 S 0.12649(4) 1.21110(11) 0.53807(3) 0.02591(17) Uani 1 1 d
S4 S 0.03214(4) 1.24685(10) 0.43348(3) 0.02568(17) Uani 1 1 d
C1 C 0.41159(15) 1.1432(4) 0.55166(13) 0.0237(5) Uani 1 1 d
C2 C 0.38256(17) 0.9416(5) 0.57533(16) 0.0306(6) Uani 1 1 d
C3 C 0.44532(18) 0.8195(5) 0.62969(16) 0.0335(6) Uani 1 1 d
C4 C 0.53865(16) 0.8932(5) 0.66124(14) 0.0298(6) Uani 1 1 d
C5 C 0.56673(17) 1.0941(5) 0.63619(15) 0.0322(6) Uani 1 1 d
C6 C 0.50434(18) 1.2202(5) 0.58244(15) 0.0289(6) Uani 1 1 d
C7 C 0.6065(2) 0.7588(7) 0.7202(2) 0.0438(8) Uani 1 1 d
C8 C 0.08296(14) 1.0734(4) 0.36903(13) 0.0215(5) Uani 1 1 d
C9 C 0.11624(17) 0.8647(4) 0.39086(14) 0.0265(5) Uani 1 1 d
C10 C 0.15565(17) 0.7386(4) 0.33934(14) 0.0252(5) Uani 1 1 d
C11 C 0.15975(15) 0.8123(4) 0.26431(13) 0.0241(5) Uani 1 1 d
C12 C 0.12377(16) 1.0201(4) 0.24265(14) 0.0259(5) Uani 1 1 d
C13 C 0.08584(15) 1.1519(4) 0.29474(14) 0.0250(5) Uani 1 1 d
C14 C 0.2017(2) 0.6726(6) 0.20824(16) 0.0343(6) Uani 1 1 d
H2 H 0.319(2) 0.883(6) 0.5553(17) 0.043(8) Uiso 1 1 d
H3 H 0.428(2) 0.685(5) 0.6433(17) 0.033(8) Uiso 1 1 d
H5 H 0.626(3) 1.149(6) 0.660(2) 0.056(10) Uiso 1 1 d
H6 H 0.5241(19) 1.353(5) 0.5685(17) 0.034(8) Uiso 1 1 d
H7A H 0.672(3) 0.782(7) 0.721(2) 0.082(14) Uiso 1 1 d
H7B H 0.598(4) 0.614(10) 0.709(3) 0.102(18) Uiso 1 1 d
H7C H 0.596(3) 0.764(8) 0.769(3) 0.094(16) Uiso 1 1 d
H9 H 0.113(2) 0.806(5) 0.4413(18) 0.036(8) Uiso 1 1 d
H10 H 0.177(2) 0.593(5) 0.3551(17) 0.035(8) Uiso 1 1 d
H12 H 0.123(2) 1.069(5) 0.1899(18) 0.035(7) Uiso 1 1 d
H13 H 0.0654(19) 1.300(5) 0.2820(15) 0.025(7) Uiso 1 1 d
H14A H 0.201(4) 0.521(9) 0.216(3) 0.102(17) Uiso 1 1 d
H14B H 0.171(3) 0.711(7) 0.159(3) 0.079(14) Uiso 1 1 d
H14C H 0.272(4) 0.708(8) 0.211(3) 0.092(15) Uiso 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'
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
C1 S1 S2 103.70(8)
S3 S2 S1 106.99(4)
S4 S3 S2 106.90(4)
C8 S4 S3 103.06(8)
C2 C1 C6 119.7(2)
C2 C1 S1 120.44(17)
C6 C1 S1 119.8(2)
C3 C2 C1 120.0(2)
C3 C2 H2 118(2)
C1 C2 H2 122(2)
C2 C3 C4 121.3(3)
C2 C3 H3 120.5(19)
C4 C3 H3 118.1(18)
C5 C4 C3 117.8(2)
C5 C4 C7 121.2(3)
C3 C4 C7 120.9(3)
C6 C5 C4 121.7(2)
C6 C5 H5 120(2)
C4 C5 H5 118(2)
C5 C6 C1 119.5(3)
C5 C6 H6 119.7(18)
C1 C6 H6 120.8(18)
C4 C7 H7A 115(3)
C4 C7 H7B 111(3)
H7A C7 H7B 103(4)
C4 C7 H7C 115(3)
H7A C7 H7C 109(4)
H7B C7 H7C 101(4)
C13 C8 C9 120.3(2)
C13 C8 S4 117.79(19)
C9 C8 S4 121.89(18)
C10 C9 C8 119.6(2)
C10 C9 H9 118.9(18)
C8 C9 H9 121.5(18)
C9 C10 C11 121.6(2)
C9 C10 H10 118.4(17)
C11 C10 H10 119.9(17)
C10 C11 C12 118.0(2)
C10 C11 C14 121.2(2)
C12 C11 C14 120.8(2)
C11 C12 C13 121.1(2)
C11 C12 H12 118.4(18)
C13 C12 H12 120.4(18)
C8 C13 C12 119.3(2)
C8 C13 H13 118.6(15)
C12 C13 H13 121.9(15)
C11 C14 H14A 117(3)
C11 C14 H14B 107(3)
H14A C14 H14B 112(4)
C11 C14 H14C 110(3)
H14A C14 H14C 104(4)
H14B C14 H14C 106(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.775(2)
S1 S2 2.0572(9)
S2 S3 2.0545(9)
S3 S4 2.0418(8)
S4 C8 1.791(2)
C1 C2 1.387(4)
C1 C6 1.390(3)
C2 C3 1.379(4)
C2 H2 0.97(3)
C3 C4 1.393(4)
C3 H3 0.90(3)
C4 C5 1.387(4)
C4 C7 1.502(4)
C5 C6 1.384(4)
C5 H5 0.91(4)
C6 H6 0.91(3)
C7 H7A 0.93(5)
C7 H7B 0.91(6)
C7 H7C 0.89(5)
C8 C13 1.387(3)
C8 C9 1.387(4)
C9 C10 1.378(4)
C9 H9 0.96(3)
C10 C11 1.393(3)
C10 H10 0.96(3)
C11 C12 1.393(4)
C11 C14 1.501(4)
C12 C13 1.394(3)
C12 H12 0.96(3)
C13 H13 0.96(3)
C14 H14A 0.94(5)
C14 H14B 0.91(5)
C14 H14C 1.00(5)
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
S2 S1 C1 C2 78.2(2)
S2 S1 C1 C6 -104.67(19)
C6 C1 C2 C3 0.6(4)
S1 C1 C2 C3 177.7(2)
C1 C2 C3 C4 -0.7(4)
C2 C3 C4 C5 0.0(4)
C2 C3 C4 C7 -179.8(3)
C3 C4 C5 C6 0.9(4)
C7 C4 C5 C6 -179.3(3)
C4 C5 C6 C1 -1.0(4)
C2 C1 C6 C5 0.2(4)
S1 C1 C6 C5 -176.88(19)
S3 S4 C8 C13 -136.97(16)
S3 S4 C8 C9 44.8(2)
C13 C8 C9 C10 2.5(3)
S4 C8 C9 C10 -179.33(18)
C8 C9 C10 C11 -2.4(4)
C9 C10 C11 C12 0.8(3)
C9 C10 C11 C14 -179.2(2)
C10 C11 C12 C13 0.8(3)
C14 C11 C12 C13 -179.2(2)
C9 C8 C13 C12 -0.9(3)
S4 C8 C13 C12 -179.18(17)
C11 C12 C13 C8 -0.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 12414244
