#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/59/4105928.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_4105928
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_moiety         'C18 H22 O S3'
_chemical_formula_sum            'C18 H22 O S3'
_chemical_formula_weight         350.54
_chemical_name_systematic
;
 ?
;
_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                99.464(3)
_cell_angle_beta                 108.734(2)
_cell_angle_gamma                92.962(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1363(4)
_cell_length_b                   9.4337(5)
_cell_length_c                   10.8331(5)
_cell_measurement_reflns_used    2375
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      70.44
_cell_measurement_theta_min      4.39
_cell_volume                     866.72(7)
_computing_cell_refinement       SAINTPLUS
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.860
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5467
_diffrn_reflns_theta_full        70.44
_diffrn_reflns_theta_max         70.44
_diffrn_reflns_theta_min         4.39
_exptl_absorpt_coefficient_mu    3.887
_exptl_absorpt_correction_T_max  0.5932
_exptl_absorpt_correction_T_min  0.2467
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.209
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0490
_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)+(0.0605P)²+1.5190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1739
_reflns_number_gt                2375
_reflns_number_total             2857
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja108865w_si_002.cif
_cod_data_source_block           16
_cod_database_code               4105928
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
C1 C 0.1100(4) 0.4258(4) 0.2853(4) 0.0372(8) Uani 1 1 d .
C2 C -0.0249(4) 0.3546(4) 0.2907(4) 0.0387(8) Uani 1 1 d .
C3 C -0.1680(4) 0.3976(5) 0.2166(4) 0.0456(10) Uani 1 1 d .
H3 H -0.2599 0.3527 0.2189 0.055 Uiso 1 1 calc R
C4 C -0.1767(4) 0.5017(5) 0.1423(4) 0.0439(9) Uani 1 1 d .
H4 H -0.2733 0.5203 0.0890 0.053 Uiso 1 1 calc R
C5 C -0.0499(5) 0.6950(4) 0.0743(4) 0.0438(9) Uani 1 1 d .
H5 H -0.1466 0.7141 0.0217 0.053 Uiso 1 1 calc R
C6 C 0.0791(5) 0.7762(4) 0.0811(4) 0.0457(9) Uani 1 1 d .
H6 H 0.0687 0.8463 0.0287 0.055 Uiso 1 1 calc R
C7 C 0.2291(5) 0.7597(4) 0.1640(4) 0.0405(9) Uani 1 1 d .
C8 C 0.2404(4) 0.6477(4) 0.2363(4) 0.0379(8) Uani 1 1 d .
C9 C 0.1074(4) 0.5500(4) 0.2235(3) 0.0357(8) Uani 1 1 d .
C10 C -0.0408(4) 0.5815(4) 0.1455(4) 0.0387(8) Uani 1 1 d .
C11 C -0.0295(5) 0.2328(5) 0.3708(4) 0.0497(10) Uani 1 1 d .
C12 C -0.1908(7) 0.2073(8) 0.3835(8) 0.095(2) Uani 1 1 d .
H12A H -0.1886 0.1387 0.4402 0.142 Uiso 1 1 calc R
H12B H -0.2659 0.1703 0.2973 0.142 Uiso 1 1 calc R
H12C H -0.2188 0.2970 0.4210 0.142 Uiso 1 1 calc R
C13 C 0.0828(7) 0.2755(6) 0.5139(5) 0.0679(14) Uani 1 1 d .
H13A H 0.0636 0.2072 0.5651 0.102 Uiso 1 1 calc R
H13B H 0.0670 0.3703 0.5522 0.102 Uiso 1 1 calc R
H13C H 0.1880 0.2758 0.5142 0.102 Uiso 1 1 calc R
C14 C 0.0017(7) 0.0890(5) 0.2998(6) 0.0706(14) Uani 1 1 d .
H14A H 0.1004 0.1011 0.2869 0.106 Uiso 1 1 calc R
H14B H -0.0789 0.0593 0.2152 0.106 Uiso 1 1 calc R
H14C H 0.0030 0.0167 0.3529 0.106 Uiso 1 1 calc R
C15 C 0.3683(5) 0.8677(5) 0.1750(4) 0.0509(10) Uani 1 1 d .
C16 C 0.3187(7) 0.9747(6) 0.0812(5) 0.0696(14) Uani 1 1 d .
H16A H 0.2386 1.0262 0.1012 0.104 Uiso 1 1 calc R
H16B H 0.2798 0.9230 -0.0090 0.104 Uiso 1 1 calc R
H16C H 0.4066 1.0422 0.0927 0.104 Uiso 1 1 calc R
C17 C 0.4337(6) 0.9619(5) 0.3160(5) 0.0617(12) Uani 1 1 d .
H17A H 0.5022 1.0425 0.3157 0.092 Uiso 1 1 calc R
H17B H 0.4901 0.9049 0.3773 0.092 Uiso 1 1 calc R
H17C H 0.3494 0.9968 0.3426 0.092 Uiso 1 1 calc R
C18 C 0.4960(6) 0.7885(6) 0.1363(5) 0.0662(13) Uani 1 1 d .
H18A H 0.4531 0.7355 0.0467 0.099 Uiso 1 1 calc R
H18B H 0.5340 0.7229 0.1953 0.099 Uiso 1 1 calc R
H18C H 0.5800 0.8580 0.1430 0.099 Uiso 1 1 calc R
S1 S 0.27975(14) 0.33666(15) 0.34036(16) 0.0715(5) Uani 1 1 d .
S2 S 0.46007(12) 0.43307(14) 0.29628(12) 0.0560(4) Uani 1 1 d .
S3 S 0.41764(12) 0.64389(13) 0.36325(11) 0.0533(3) Uani 1 1 d .
O1 O 0.4310(4) 0.4110(4) 0.1526(4) 0.0733(10) 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'
S S 0.3331 0.5567 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C9 122.3(3)
C2 C1 S1 114.5(3)
C9 C1 S1 122.7(3)
C1 C2 C3 116.7(4)
C1 C2 C11 125.1(3)
C3 C2 C11 118.2(3)
C4 C3 C2 122.8(4)
C4 C3 H3 118.6
C2 C3 H3 118.6
C3 C4 C10 120.5(4)
C3 C4 H4 119.8
C10 C4 H4 119.8
C6 C5 C10 121.1(4)
C6 C5 H5 119.4
C10 C5 H5 119.4
C5 C6 C7 123.0(4)
C5 C6 H6 118.5
C7 C6 H6 118.5
C8 C7 C6 116.6(4)
C8 C7 C15 124.2(4)
C6 C7 C15 119.1(4)
C7 C8 C9 122.3(3)
C7 C8 S3 118.0(3)
C9 C8 S3 119.1(3)
C10 C9 C1 116.9(3)
C10 C9 C8 117.0(3)
C1 C9 C8 126.1(3)
C4 C10 C5 120.6(3)
C4 C10 C9 119.9(4)
C5 C10 C9 119.5(4)
C13 C11 C14 111.8(4)
C13 C11 C12 105.1(4)
C14 C11 C12 106.7(5)
C13 C11 C2 111.5(4)
C14 C11 C2 110.9(4)
C12 C11 C2 110.7(4)
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
C16 C15 C17 105.3(4)
C16 C15 C18 106.5(4)
C17 C15 C18 111.6(4)
C16 C15 C7 111.6(4)
C17 C15 C7 110.4(3)
C18 C15 C7 111.3(4)
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C15 C17 H17A 109.5
C15 C17 H17B 109.5
H17A C17 H17B 109.5
C15 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C1 S1 S2 110.22(14)
O1 S2 S1 112.18(17)
O1 S2 S3 109.21(16)
S1 S2 S3 93.66(7)
C8 S3 S2 98.06(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.395(5)
C1 C9 1.439(5)
C1 S1 1.782(4)
C2 C3 1.417(6)
C2 C11 1.557(6)
C3 C4 1.357(6)
C3 H3 0.9300
C4 C10 1.407(6)
C4 H4 0.9300
C5 C6 1.346(6)
C5 C10 1.410(6)
C5 H5 0.9300
C6 C7 1.409(6)
C6 H6 0.9300
C7 C8 1.405(5)
C7 C15 1.549(6)
C8 C9 1.442(5)
C8 S3 1.762(4)
C9 C10 1.423(5)
C11 C13 1.532(7)
C11 C14 1.533(7)
C11 C12 1.534(7)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 C16 1.531(7)
C15 C17 1.547(6)
C15 C18 1.548(7)
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
S1 S2 2.0645(17)
S2 O1 1.470(4)
S2 S3 2.1019(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660240
