Crystal Structures and Spectroscopic Characterization of Radical Cations and Dications of Oligothiophenes Stabilized by Annelation with Bicyclo[2.2.2]octene Units: Sterically Segregated Cationic Oligothiophenes
Tohru Nishinaga; Atsushi Wakamiya; Daisuke Yamazaki; Koichi Komatsu; Journal of the American Chemical Society 126 (2004) 3163–3174; doi:10.1021/ja039434v

data_4112313
_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
;
 Crystal Structures and Spectroscopic Characterization of Radical Cations
 and Dications of Oligothiophenes Stabilized by Annelation with
 Bicyclo[2.2.2]octene Units: Sterically Segregated Cationic
 Oligothiophenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3163
_journal_page_last               3174
_journal_paper_doi               10.1021/ja039434v
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C30 H32 S3, F6 Sb, C H2 Cl2'
_chemical_formula_sum            'C31 H34 Cl2 F6 S3 Sb'
_chemical_formula_weight         809.41
_chemical_name_systematic
; 
4,5:4'',5''-Bis(bicyclo[2.2.2]octeno)-
3',4'-bicyclo[2.2.2]octano-2,2':5',2''-
terthiophene radical cation hexafluoroantimonate
;
_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_date             ' May 2 2003 '
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.644(5)
_cell_angle_beta                 100.024(5)
_cell_angle_gamma                98.039(5)
_cell_formula_units_Z            2
_cell_length_a                   9.653(5)
_cell_length_b                   12.687(5)
_cell_length_c                   13.237(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1571.4(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SHELXS-97 (Sheldrick, 1990)'
_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 0.963
_diffrn_measured_fraction_theta_max 0.963
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7967
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    1.306
_exptl_absorpt_correction_T_max  0.7802
_exptl_absorpt_correction_T_min  0.7802
_exptl_absorpt_correction_type   empirical(SADABS)
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_description       prism
_exptl_crystal_F_000             814
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         4.884
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         5337
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0605
_refine_ls_shift/su_max          0.370
_refine_ls_shift/su_mean         0.049
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1153P)^2^+6.9871P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1815
_refine_ls_wR_factor_ref         0.1856
_reflns_number_gt                4559
_reflns_number_total             5337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja039434v_s2.cif
_cod_data_source_block           1(3T)+
_cod_database_code               4112313