1,2-Dithiin Annelated with Bicyclo[2.2.2]octene Frameworks. One-Electron and Two-Electron Oxidations and Formation of a Novel 2,3,5,6-Tetrathiabicyclo[2.2.2]oct-7-ene Radical Cation with Remarkable Stability Owing to a Strong Transannular Interaction
Atsushi Wakamiya; Tohru Nishinaga; Koichi Komatsu; Journal of the American Chemical Society 124 (2002) 15038–15050; doi:10.1021/ja028297j

data_4115387
_publ_contact_author_address
;
    Institute for Chemical Research, Kyoto University, Gokasho, Uji, 
    Kyoto 611-0011, Japan. 
;
_publ_contact_author_email       ' komatsu@scl.kyoto-u.ac.jp'
_publ_contact_author_fax         ' +81-774-38-3178 '
_publ_contact_author_name        ' Koichi Komatsu '
_publ_contact_author_phone       ' +81-774-38-3172 '
_publ_section_title
;
 1,2-Dithiin Annelated with Bicyclo[2.2.2]octene Frameworks. One-Electron
 and Two-Electron Oxidations and Formation of a Novel
 2,3,5,6-Tetrathiabicyclo[2.2.2]oct-7-ene Radical Cation with Remarkable
 Stability Owing to a Strong Transannular Interaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15038
_journal_page_last               15050
_journal_paper_doi               10.1021/ja028297j
_journal_volume                  124
_journal_year                    2002
_chemical_formula_moiety         'C16 H20 Cl6 S4 Sb'
_chemical_formula_sum            'C16 H20 Cl6 S4 Sb'
_chemical_formula_weight         675.01
_chemical_name_common            'tetrathia radical cation'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             ' Wed July 17 2002 '
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.488(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0506(8)
_cell_length_b                   23.896(2)
_cell_length_c                   12.1284(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    123(2)
_cell_volume                     2318.3(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12811
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    2.245
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_description       prism
_exptl_crystal_F_000             1332
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         1.190
_refine_diff_density_min         -1.242
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+11.3519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                3714
_reflns_number_total             4015
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja028297j-3_s2_2.cif
_cod_data_source_block           tetrathia
_cod_database_code               4115387