Sulfur Monoxide Transfer from peri-Substituted Trisulfide-2-oxides to Dienes: Substituent Effects, Mechanistic Studies and Application in Thiophene Synthesis
Richard S. Grainger; Bhaven Patel; Benson M. Kariuki; Louise Male; Neil Spencer; Journal of the American Chemical Society 133 (2011) 5843–5852; doi:10.1021/ja108865w

data_4105927
_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       \w
_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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0422P)^2^+0.1141P] where P=(Fo^2^+2Fc^2^)/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