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_4115390
_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         'C17 H23 Cl8 O2 Sb'
_chemical_formula_sum            'C17 H23 Cl8 O2 Sb'
_chemical_formula_weight         664.70
_chemical_name_common            'protonated 2-butene-1,4-dione'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.970(2)
_cell_length_b                   13.3437(19)
_cell_length_c                   14.041(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    100(2)
_cell_volume                     2430.0(6)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12624
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    2.028
_exptl_absorpt_correction_T_max  0.816
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            paleyellow
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_description       prism
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.259
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2229
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0376
_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/[\s^2^(Fo^2^)+(0.0442P)^2^+3.4990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0887
_reflns_number_gt                1981
_reflns_number_total             2229
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja028297j-3_s2_5.cif
_cod_data_source_block           2waka
_cod_original_cell_volume        2429.9(6)
_cod_database_code               4115390