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_4112314
_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         'C40 H42 S4, 2(F6 Sb)'
_chemical_formula_sum            'C40 H42 F12 S4 Sb2'
_chemical_formula_weight         1122.54
_chemical_name_systematic
; 
4,5:4''',5'''-Bis(bicyclo[2.2.2]octeno)-
3',4':3'',4''-bis(bicyclo[2.2.2]octano)-
2,2':5',2'',5'',2'''-quarterthiophene dication 
bis(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                109.542(5)
_cell_angle_beta                 100.177(5)
_cell_angle_gamma                97.274(5)
_cell_formula_units_Z            1
_cell_length_a                   7.918(5)
_cell_length_b                   9.912(5)
_cell_length_c                   13.964(5)
_cell_measurement_temperature    100(2)
_cell_volume                     996.0(9)
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.1131
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5208
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    1.654
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.8521
_exptl_absorpt_correction_type   empirical(SADABS)
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_description       prism
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.817
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3453
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0509
_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^)+(0.0180P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                2372
_reflns_number_total             3453
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja039434v_s3.cif
_cod_data_source_block           1(4T)2+
_cod_database_code               4112314