#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/59/4105927.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_4105927
loop_
_publ_author_name
'Richard S. Grainger'
'Bhaven Patel'
'Benson M. Kariuki'
'Louise Male'
'Neil Spencer'
_publ_contact_author
;
Dr B.M. Kariuki
School of Chemistry, Cardiff University
Main Building
Park Place
Cardiff
CF10 3AT
;
_publ_contact_author_email       kariukib@cf.ac.uk
_publ_section_title
;
 Sulfur Monoxide Transfer from peri-Substituted Trisulfide-2-oxides to
 Dienes: Substituent Effects, Mechanistic Studies and Application in
 Thiophene Synthesis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5843
_journal_page_last               5852
_journal_paper_doi               10.1021/ja108865w
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C10 H6 O S3'
_chemical_formula_weight         238.33
_chemical_name_common            apsph
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7520(4)
_cell_length_b                   13.1500(4)
_cell_length_c                   15.3530(11)
_cell_measurement_temperature    120(2)
_cell_volume                     959.39(11)
_computing_cell_refinement       'Nonius Collect'
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'XSeed interface to POVRay'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       ω
_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  0.0643
_diffrn_reflns_av_sigmaI/netI    0.0753
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5097
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  0.9645
_exptl_absorpt_correction_T_min  0.8111
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.24(11)
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0422P)²+0.1141P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                1863
_reflns_number_total             2117
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja108865w_si_001.cif
_cod_data_source_block           15
_cod_database_code               4105927
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.90462(17) 0.37763(6) 0.73064(5) 0.0255(2) Uani 1 1 d .
O1 O 0.5507(5) 0.52335(19) 0.63568(15) 0.0334(6) Uani 1 1 d .
C1 C 0.6647(6) 0.3965(2) 0.81760(17) 0.0156(6) Uani 1 1 d .
S2 S 0.85190(16) 0.50835(6) 0.65483(5) 0.0201(2) Uani 1 1 d .
C2 C 0.5488(6) 0.3074(2) 0.84861(19) 0.0193(6) Uani 1 1 d .
H2 H 0.5961 0.2449 0.8212 0.023 Uiso 1 1 calc R
S3 S 0.96921(15) 0.61042(6) 0.75324(5) 0.0208(2) Uani 1 1 d .
C3 C 0.3628(7) 0.3068(2) 0.9196(2) 0.0203(6) Uani 1 1 d .
H3 H 0.2918 0.2444 0.9418 0.024 Uiso 1 1 calc R
C4 C 0.2850(6) 0.3974(2) 0.95669(19) 0.0202(7) Uani 1 1 d .
H4 H 0.1564 0.3974 1.0041 0.024 Uiso 1 1 calc R
C5 C 0.3016(6) 0.5836(2) 0.96403(19) 0.0188(6) Uani 1 1 d .
H5 H 0.1712 0.5816 1.0109 0.023 Uiso 1 1 calc R
C6 C 0.3975(6) 0.6755(2) 0.9350(2) 0.0190(6) Uani 1 1 d .
H6 H 0.3321 0.7367 0.9608 0.023 Uiso 1 1 calc R
C7 C 0.5933(6) 0.6786(2) 0.86670(19) 0.0185(6) Uani 1 1 d .
H7 H 0.6577 0.7424 0.8458 0.022 Uiso 1 1 calc R
C8 C 0.6942(6) 0.5900(2) 0.82926(17) 0.0148(6) Uani 1 1 d .
C9 C 0.5925(5) 0.4923(2) 0.85545(17) 0.0145(6) Uani 1 1 d .
C10 C 0.3928(6) 0.4906(2) 0.92561(18) 0.0148(6) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0290(4) 0.0191(4) 0.0286(4) 0.0000(3) 0.0146(3) 0.0052(3)
O1 0.0250(12) 0.0517(16) 0.0235(11) -0.0008(11) -0.0110(10) 0.0025(11)
C1 0.0155(14) 0.0180(14) 0.0134(13) 0.0002(12) 0.0011(11) 0.0018(12)
S2 0.0210(4) 0.0255(4) 0.0138(4) -0.0006(3) 0.0010(3) -0.0004(3)
C2 0.0203(15) 0.0167(14) 0.0208(15) -0.0009(13) -0.0009(13) 0.0020(12)
S3 0.0197(4) 0.0221(4) 0.0207(4) -0.0037(3) 0.0063(3) -0.0052(3)
C3 0.0217(15) 0.0175(14) 0.0218(15) 0.0063(13) 0.0001(13) -0.0028(13)
C4 0.0157(14) 0.0289(17) 0.0159(15) 0.0042(13) 0.0022(11) 0.0007(13)
C5 0.0166(14) 0.0255(16) 0.0142(14) -0.0037(13) 0.0019(12) 0.0015(12)
C6 0.0170(14) 0.0220(15) 0.0179(14) -0.0063(12) -0.0021(13) 0.0011(13)
C7 0.0198(15) 0.0155(14) 0.0201(14) -0.0031(12) -0.0017(13) -0.0036(12)
C8 0.0112(13) 0.0208(14) 0.0125(13) -0.0002(12) -0.0026(11) -0.0016(11)
C9 0.0118(13) 0.0193(14) 0.0125(13) -0.0012(12) -0.0030(10) 0.0020(12)
C10 0.0143(13) 0.0175(13) 0.0125(13) 0.0004(12) -0.0032(10) 0.0007(12)
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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S1 S2 103.11(10)
C2 C1 C9 120.8(3)
C2 C1 S1 113.4(2)
C9 C1 S1 125.8(2)
O1 S2 S1 109.71(11)
O1 S2 S3 108.43(11)
S1 S2 S3 95.35(4)
C1 C2 C3 121.6(3)
C8 S3 S2 100.47(10)
C4 C3 C2 119.1(3)
C3 C4 C10 121.1(3)
C6 C5 C10 121.5(3)
C5 C6 C7 119.4(3)
C8 C7 C6 121.1(3)
C7 C8 C9 121.5(3)
C7 C8 S3 113.7(2)
C9 C8 S3 124.7(2)
C1 C9 C8 126.6(2)
C1 C9 C10 116.8(3)
C8 C9 C10 116.6(3)
C4 C10 C5 119.7(3)
C4 C10 C9 120.4(3)
C5 C10 C9 119.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.773(3)
S1 S2 2.0910(11)
O1 S2 1.475(2)
C1 C2 1.380(4)
C1 C9 1.428(4)
S2 S3 2.0965(10)
C2 C3 1.404(4)
S3 C8 1.773(3)
C3 C4 1.371(4)
C4 C10 1.411(4)
C5 C6 1.366(4)
C5 C10 1.425(4)
C6 C7 1.402(4)
C7 C8 1.384(4)
C8 C9 1.431(4)
C9 C10 1.436(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9439926
