#------------------------------------------------------------------------------
#$Date: 2025-08-22 13:33:34 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301861 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/01/7150164.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_7150164
loop_
_publ_author_name
'Spivey, Alan C.'
'Colley, Jacqueline'
'Sprigens, Lindsey'
'Hancock, Susan M.'
'Cameron, D. Stuart'
'Chigboh, Kordi I.'
'Veitch, Gemma'
'Frampton, Christopher S.'
'Adams, Harry'
_publ_section_title
;
 The synthesis of water soluble decalin-based thiols and
 S-nitrosothiols--model systems for studying the reactions of nitric
 oxide with protein thiols.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1942
_journal_page_last               1952
_journal_paper_doi               10.1039/b503758a
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C14 H22 O5 S'
_chemical_formula_weight         302.38
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.400(8)
_cell_angle_beta                 105.284(9)
_cell_angle_gamma                92.286(9)
_cell_formula_units_Z            2
_cell_length_a                   6.8076(9)
_cell_length_b                   9.3008(12)
_cell_length_c                   12.2010(18)
_cell_measurement_reflns_used    4343
_cell_measurement_temperature    123(1)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      1.74
_cell_volume                     738.62(18)
_computing_cell_refinement       'SMART V5.060/SAINT V6.02a (Bruker AXS, 1999)'
_computing_data_collection       'SMART V5.060 (Bruker AXS, 1999)'
_computing_data_reduction        'SAINT V6.02a (Bruker AXS, 1997)'
_computing_molecular_graphics    'SHELXTL V5.10 (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL V5.10 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXTL V5.10 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL V5.10 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(1)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker AXS 1K CCD area detector'
_diffrn_measurement_method       'narrow frame ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6317
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                2426
_reflns_number_total             2987
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b503758a.txt
_cod_data_source_block           csf94s
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        738.62(17)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150164
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.33160(6) 0.83743(4) 0.26431(4) 0.02268(14) Uani 1 1 d . . .
O1 O -0.19803(16) 1.21422(12) 0.24921(9) 0.0200(3) Uani 1 1 d . . .
O2 O 0.38069(19) 1.24089(13) 0.17006(10) 0.0264(3) Uani 1 1 d . . .
H2C H 0.508(4) 1.226(2) 0.2055(19) 0.044(6) Uiso 1 1 d . . .
O3 O 0.36431(16) 1.00833(12) 0.29487(9) 0.0226(3) Uani 1 1 d . . .
O4 O 0.12262(18) 0.79255(13) 0.25165(11) 0.0303(3) Uani 1 1 d . . .
O5 O 0.4864(2) 0.78265(14) 0.35029(11) 0.0347(3) Uani 1 1 d . . .
C1 C 0.1895(2) 1.09970(17) 0.27155(14) 0.0197(3) Uani 1 1 d . . .
H1A H 0.0842 1.0581 0.1999 0.024 Uiso 1 1 calc R . .
C2 C 0.0991(2) 1.11222(17) 0.37333(14) 0.0214(4) Uani 1 1 d . . .
H2A H 0.0340 1.0168 0.3780 0.026 Uiso 1 1 calc R . .
H2B H 0.2100 1.1392 0.4447 0.026 Uiso 1 1 calc R . .
C3 C -0.0573(2) 1.22432(17) 0.36397(13) 0.0187(3) Uani 1 1 d . . .
C4 C -0.1588(3) 1.24122(18) 0.46010(14) 0.0232(4) Uani 1 1 d . . .
H4A H -0.2598 1.1578 0.4496 0.028 Uiso 1 1 calc R . .
H4B H -0.0543 1.2381 0.5334 0.028 Uiso 1 1 calc R . .
C5 C -0.2647(2) 1.37872(18) 0.46808(15) 0.0253(4) Uani 1 1 d . . .
H5A H -0.3381 1.3920 0.5243 0.030 Uiso 1 1 calc R . .
C6 C -0.2636(2) 1.48273(18) 0.40289(15) 0.0257(4) Uani 1 1 d . . .
H6A H -0.3370 1.5651 0.4151 0.031 Uiso 1 1 calc R . .
C7 C -0.1543(2) 1.47976(17) 0.31073(14) 0.0240(4) Uani 1 1 d . . .
H7A H -0.0496 1.5623 0.3306 0.029 Uiso 1 1 calc R . .
H7B H -0.2536 1.4940 0.2379 0.029 Uiso 1 1 calc R . .
C8 C -0.0521(2) 1.34181(17) 0.29203(13) 0.0194(3) Uani 1 1 d . . .
C9 C 0.1106(2) 1.35139(17) 0.22850(14) 0.0225(4) Uani 1 1 d . . .
H9A H 0.1744 1.4517 0.2449 0.027 Uiso 1 1 calc R . .
H9B H 0.0438 1.3325 0.1452 0.027 Uiso 1 1 calc R . .
C10 C 0.2780(2) 1.24732(18) 0.25809(14) 0.0215(3) Uani 1 1 d . . .
H10A H 0.3773 1.2880 0.3323 0.026 Uiso 1 1 calc R . .
C11 C 0.3890(3) 0.80118(18) 0.12760(14) 0.0239(4) Uani 1 1 d . . .
C12 C 0.2502(3) 0.8861(2) 0.04137(15) 0.0321(4) Uani 1 1 d . . .
H12A H 0.2700 0.8595 -0.0348 0.048 Uiso 1 1 calc R . .
H12B H 0.2844 0.9903 0.0647 0.048 Uiso 1 1 calc R . .
H12C H 0.1074 0.8628 0.0391 0.048 Uiso 1 1 calc R . .
C13 C 0.3424(3) 0.63728(19) 0.09066(16) 0.0310(4) Uani 1 1 d . . .
H13A H 0.3782 0.6106 0.0187 0.046 Uiso 1 1 calc R . .
H13B H 0.1966 0.6124 0.0795 0.046 Uiso 1 1 calc R . .
H13C H 0.4226 0.5843 0.1502 0.046 Uiso 1 1 calc R . .
C14 C 0.6145(3) 0.8443(2) 0.14388(17) 0.0337(4) Uani 1 1 d . . .
H14A H 0.6478 0.8246 0.0705 0.051 Uiso 1 1 calc R . .
H14B H 0.6982 0.7881 0.1997 0.051 Uiso 1 1 calc R . .
H14C H 0.6424 0.9480 0.1719 0.051 Uiso 1 1 calc R . .
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'
O O 0.0106 0.0060 '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'
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
O4 S1 O5 118.73(8) . . ?
O4 S1 O3 109.34(7) . . ?
O5 S1 O3 104.71(7) . . ?
O4 S1 C11 109.47(8) . . ?
O5 S1 C11 109.00(8) . . ?
O3 S1 C11 104.61(7) . . ?
C3 O1 C8 60.61(10) . . ?
C10 O2 H2C 104.2(14) . . ?
C1 O3 S1 120.79(10) . . ?
O3 C1 C2 109.10(12) . . ?
O3 C1 C10 105.36(12) . . ?
C2 C1 C10 110.14(13) . . ?
O3 C1 H1A 110.7 . . ?
C2 C1 H1A 110.7 . . ?
C10 C1 H1A 110.7 . . ?
C3 C2 C1 111.78(13) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
O1 C3 C8 59.91(9) . . ?
O1 C3 C4 114.46(12) . . ?
C8 C3 C4 121.03(13) . . ?
O1 C3 C2 112.80(12) . . ?
C8 C3 C2 119.94(13) . . ?
C4 C3 C2 115.34(13) . . ?
C5 C4 C3 114.15(14) . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 C4 124.95(15) . . ?
C6 C5 H5A 117.5 . . ?
C4 C5 H5A 117.5 . . ?
C5 C6 C7 124.45(15) . . ?
C5 C6 H6A 117.8 . . ?
C7 C6 H6A 117.8 . . ?
C6 C7 C8 114.49(14) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 C3 59.48(9) . . ?
O1 C8 C7 112.94(13) . . ?
C3 C8 C7 120.72(14) . . ?
O1 C8 C9 113.62(13) . . ?
C3 C8 C9 120.39(13) . . ?
C7 C8 C9 115.62(13) . . ?
C8 C9 C10 115.03(13) . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
O2 C10 C1 112.89(13) . . ?
O2 C10 C9 107.15(12) . . ?
C1 C10 C9 110.79(12) . . ?
O2 C10 H10A 108.6 . . ?
C1 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C14 C11 C12 111.88(14) . . ?
C14 C11 C13 110.91(14) . . ?
C12 C11 C13 110.33(15) . . ?
C14 C11 S1 108.66(12) . . ?
C12 C11 S1 108.83(11) . . ?
C13 C11 S1 106.03(11) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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
S1 O4 1.4299(13) . ?
S1 O5 1.4318(13) . ?
S1 O3 1.5846(12) . ?
S1 C11 1.8103(17) . ?
O1 C3 1.4639(18) . ?
O1 C8 1.4705(18) . ?
O2 C10 1.4250(18) . ?
O2 H2C 0.89(2) . ?
O3 C1 1.4749(18) . ?
C1 C2 1.520(2) . ?
C1 C10 1.520(2) . ?
C1 H1A 1.0000 . ?
C2 C3 1.512(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.481(2) . ?
C3 C4 1.508(2) . ?
C4 C5 1.499(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.320(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.502(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.507(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.515(2) . ?
C9 C10 1.522(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 1.0000 . ?
C11 C14 1.527(2) . ?
C11 C12 1.531(2) . ?
C11 C13 1.536(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2C O1 0.89(2) 1.94(2) 2.8052(17) 165(2) 1_655
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
O4 S1 O3 C1 -19.19(13) . . . . ?
O5 S1 O3 C1 -147.42(11) . . . . ?
C11 S1 O3 C1 97.98(12) . . . . ?
S1 O3 C1 C2 87.31(14) . . . . ?
S1 O3 C1 C10 -154.47(10) . . . . ?
O3 C1 C2 C3 170.37(12) . . . . ?
C10 C1 C2 C3 55.19(17) . . . . ?
C8 O1 C3 C4 113.01(15) . . . . ?
C8 O1 C3 C2 -112.47(14) . . . . ?
C1 C2 C3 O1 44.43(17) . . . . ?
C1 C2 C3 C8 -22.9(2) . . . . ?
C1 C2 C3 C4 178.53(13) . . . . ?
O1 C3 C4 C5 -63.58(18) . . . . ?
C8 C3 C4 C5 4.8(2) . . . . ?
C2 C3 C4 C5 163.07(14) . . . . ?
C3 C4 C5 C6 -3.7(2) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 3.4(2) . . . . ?
C3 O1 C8 C7 -113.23(15) . . . . ?
C3 O1 C8 C9 112.53(15) . . . . ?
C4 C3 C8 O1 -102.11(15) . . . . ?
C2 C3 C8 O1 100.55(15) . . . . ?
O1 C3 C8 C7 100.13(15) . . . . ?
C4 C3 C8 C7 -2.0(2) . . . . ?
C2 C3 C8 C7 -159.32(14) . . . . ?
O1 C3 C8 C9 -101.15(16) . . . . ?
C4 C3 C8 C9 156.74(15) . . . . ?
C2 C3 C8 C9 -0.6(2) . . . . ?
C6 C7 C8 O1 64.94(17) . . . . ?
C6 C7 C8 C3 -2.1(2) . . . . ?
C6 C7 C8 C9 -161.78(14) . . . . ?
O1 C8 C9 C10 -75.49(17) . . . . ?
C3 C8 C9 C10 -8.2(2) . . . . ?
C7 C8 C9 C10 151.55(14) . . . . ?
O3 C1 C10 O2 57.44(16) . . . . ?
C2 C1 C10 O2 174.97(13) . . . . ?
O3 C1 C10 C9 177.62(12) . . . . ?
C2 C1 C10 C9 -64.85(17) . . . . ?
C8 C9 C10 O2 163.70(13) . . . . ?
C8 C9 C10 C1 40.2(2) . . . . ?
O4 S1 C11 C14 -177.82(11) . . . . ?
O5 S1 C11 C14 -46.45(14) . . . . ?
O3 S1 C11 C14 65.10(13) . . . . ?
O4 S1 C11 C12 60.12(13) . . . . ?
O5 S1 C11 C12 -168.51(12) . . . . ?
O3 S1 C11 C12 -56.96(13) . . . . ?
O4 S1 C11 C13 -58.55(13) . . . . ?
O5 S1 C11 C13 72.82(13) . . . . ?
O3 S1 C11 C13 -175.63(11) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11392478
