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#$Date: 2016-03-22 11:19:20 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178894 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/23/4112314.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4112314
loop_
_publ_author_name
'Tohru Nishinaga'
'Atsushi Wakamiya'
'Daisuke Yamazaki'
'Koichi Komatsu'
_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/[σ²(Fo²)+(0.0180P)²+0.0000P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F6 F 0.5721(13) 0.4908(11) 0.1192(6) 0.062(3) Uani 0.704(10) 1 d PU A 1
F3 F 0.6307(11) 0.5450(8) 0.3986(5) 0.049(3) Uani 0.704(10) 1 d PU A 1
F2 F 0.3666(9) 0.4603(8) 0.2394(7) 0.051(2) Uani 0.704(10) 1 d PU A 1
F5 F 0.8406(9) 0.5744(9) 0.2795(9) 0.073(3) Uani 0.704(10) 1 d PU A 1
F14 F 0.790(3) 0.646(2) 0.3790(13) 0.086(9) Uani 0.296(10) 1 d PU A 2
F11 F 0.478(4) 0.495(2) 0.336(3) 0.115(13) Uani 0.296(10) 1 d PU A 2
F12 F 0.471(4) 0.428(2) 0.140(2) 0.110(12) Uani 0.296(10) 1 d PU A 2
F13 F 0.784(3) 0.5743(18) 0.186(2) 0.081(9) Uani 0.296(10) 1 d PU A 2
Sb1 Sb 0.61176(7) 0.52303(5) 0.25913(4) 0.03031(17) Uani 1 1 d . . .
S2 S 1.1115(2) 0.36330(16) 0.37918(13) 0.0205(4) Uani 1 1 d . . .
S1 S 0.9424(2) -0.10363(16) 0.21454(13) 0.0228(4) Uani 1 1 d . . .
F1 F 0.5713(6) 0.7091(4) 0.2832(4) 0.0547(13) Uani 1 1 d . A .
C2 C 1.1958(8) -0.0316(7) 0.1382(5) 0.0211(15) Uani 1 1 d . . .
F4 F 0.6527(9) 0.3371(6) 0.2380(4) 0.105(2) Uani 1 1 d . A .
C18 C 0.7199(7) 0.3008(6) 0.5225(5) 0.0202(16) Uani 1 1 d . . .
H18 H 0.7147 0.4002 0.5705 0.024 Uiso 1 1 calc R . .
C4 C 1.0527(7) 0.0780(6) 0.2650(5) 0.0143(14) Uani 1 1 d . . .
C3 C 1.1855(7) 0.0967(6) 0.2149(4) 0.0173(14) Uani 1 1 d . . .
H3 H 1.2612 0.1878 0.2315 0.021 Uiso 1 1 calc R . .
C6 C 0.8748(7) 0.1777(6) 0.3992(4) 0.0165(14) Uani 1 1 d . . .
C8 C 0.9873(7) 0.4265(6) 0.4691(5) 0.0167(15) Uani 1 1 d . . .
C20 C 0.7585(9) 0.2015(7) 0.5834(5) 0.0282(17) Uani 1 1 d . . .
H20A H 0.6663 0.1921 0.6216 0.034 Uiso 1 1 calc R . .
H20B H 0.8725 0.2435 0.6349 0.034 Uiso 1 1 calc R . .
C15 C 0.7434(8) 0.0514(6) 0.3941(5) 0.0213(16) Uani 1 1 d . . .
H15 H 0.7579 -0.0432 0.3439 0.026 Uiso 1 1 calc R . .
C7 C 0.8619(8) 0.3092(6) 0.4668(5) 0.0166(14) Uani 1 1 d . . .
C16 C 0.5660(8) 0.0862(6) 0.3612(5) 0.0266(17) Uani 1 1 d . . .
H16A H 0.4720 0.0076 0.3579 0.032 Uiso 1 1 calc R . .
H16B H 0.5523 0.0912 0.2906 0.032 Uiso 1 1 calc R . .
C19 C 0.5494(8) 0.2324(6) 0.4392(5) 0.0256(17) Uani 1 1 d . . .
H19A H 0.5225 0.2992 0.4020 0.031 Uiso 1 1 calc R . .
H19B H 0.4522 0.2165 0.4726 0.031 Uiso 1 1 calc R . .
C5 C 1.0048(7) 0.1841(6) 0.3429(5) 0.0164(14) Uani 1 1 d . . .
C14 C 1.1882(8) -0.1326(7) -0.0449(5) 0.0249(16) Uani 1 1 d . . .
H14A H 1.2571 -0.1644 -0.0981 0.030 Uiso 1 1 calc R . .
H14B H 1.1298 -0.0555 -0.0576 0.030 Uiso 1 1 calc R . .
C9 C 1.0742(8) -0.2888(6) 0.0491(5) 0.0261(17) Uani 1 1 d . . .
H9 H 0.9816 -0.3698 0.0460 0.031 Uiso 1 1 calc R . .
C13 C 1.3978(8) -0.1941(7) 0.0814(5) 0.0309(18) Uani 1 1 d . . .
H13A H 1.4636 -0.2305 0.0271 0.037 Uiso 1 1 calc R . .
H13B H 1.4815 -0.1553 0.1505 0.037 Uiso 1 1 calc R . .
C1 C 1.0717(8) -0.1465(6) 0.1313(5) 0.0205(15) Uani 1 1 d . . .
C17 C 0.7636(9) 0.0503(7) 0.5051(5) 0.0321(18) Uani 1 1 d . . .
H17A H 0.8762 0.0229 0.5264 0.038 Uiso 1 1 calc R . .
H17B H 0.6679 -0.0237 0.5058 0.038 Uiso 1 1 calc R . .
C12 C 1.3096(8) -0.0715(6) 0.0634(5) 0.0230(16) Uani 1 1 d . . .
H12 H 1.3987 0.0152 0.0718 0.028 Uiso 1 1 calc R . .
C10 C 1.2596(8) -0.3180(7) 0.0766(6) 0.0318(18) Uani 1 1 d . . .
H10A H 1.2792 -0.3299 0.1451 0.038 Uiso 1 1 calc R . .
H10B H 1.2701 -0.4101 0.0233 0.038 Uiso 1 1 calc R . .
C11 C 1.0505(9) -0.2619(7) -0.0549(5) 0.0303(18) Uani 1 1 d . . .
H11A H 1.0612 -0.3504 -0.1114 0.036 Uiso 1 1 calc R . .
H11B H 0.9321 -0.2420 -0.0735 0.036 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
F11 Sb1 F12 98.4(16) .
F11 Sb1 F5 133.9(13) .
F12 Sb1 F5 124.8(12) .
F11 Sb1 F6 132.5(13) .
F12 Sb1 F6 35.6(11) .
F5 Sb1 F6 93.3(4) .
F11 Sb1 F1 91.5(6) .
F12 Sb1 F1 101.3(8) .
F5 Sb1 F1 94.8(3) .
F6 Sb1 F1 88.9(3) .
F11 Sb1 F4 87.6(6) .
F12 Sb1 F4 79.7(8) .
F5 Sb1 F4 85.2(3) .
F6 Sb1 F4 92.3(3) .
F1 Sb1 F4 178.8(2) .
F11 Sb1 F3 42.1(12) .
F12 Sb1 F3 138.9(13) .
F5 Sb1 F3 91.9(4) .
F6 Sb1 F3 174.5(5) .
F1 Sb1 F3 92.4(3) .
F4 Sb1 F3 86.4(3) .
F11 Sb1 F2 44.6(12) .
F12 Sb1 F2 55.8(12) .
F5 Sb1 F2 177.3(4) .
F6 Sb1 F2 88.0(4) .
F1 Sb1 F2 87.5(3) .
F4 Sb1 F2 92.4(3) .
F3 Sb1 F2 86.7(3) .
F11 Sb1 F14 91.1(14) .
F12 Sb1 F14 169.8(15) .
F5 Sb1 F14 47.6(7) .
F6 Sb1 F14 134.2(9) .
F1 Sb1 F14 74.7(5) .
F4 Sb1 F14 104.5(6) .
F3 Sb1 F14 51.2(7) .
F2 Sb1 F14 132.2(7) .
F11 Sb1 F13 173.0(14) .
F12 Sb1 F13 88.4(13) .
F5 Sb1 F13 40.5(7) .
F6 Sb1 F13 53.8(8) .
F1 Sb1 F13 85.4(6) .
F4 Sb1 F13 95.5(6) .
F3 Sb1 F13 131.6(9) .
F2 Sb1 F13 141.2(9) .
F14 Sb1 F13 82.0(10) .
C5 S2 C8 92.3(3) .
C1 S1 C4 90.5(3) .
C1 C2 C3 111.3(5) .
C1 C2 C12 114.0(5) .
C3 C2 C12 134.6(6) .
C7 C18 C19 106.9(5) .
C7 C18 C20 107.2(5) .
C19 C18 C20 110.1(5) .
C5 C4 C3 127.4(5) .
C5 C4 S1 121.9(4) .
C3 C4 S1 110.7(4) .
C2 C3 C4 112.8(5) .
C7 C6 C5 114.6(5) .
C7 C6 C15 114.4(5) .
C5 C6 C15 131.0(5) .
C8 C8 C7 127.8(7) 2_766
C8 C8 S2 122.0(6) 2_766
C7 C8 S2 110.3(4) .
C18 C20 C17 108.3(5) .
C6 C15 C16 105.2(5) .
C6 C15 C17 107.7(5) .
C16 C15 C17 108.4(5) .
C6 C7 C8 112.9(5) .
C6 C7 C18 113.8(5) .
C8 C7 C18 133.3(5) .
C15 C16 C19 110.2(5) .
C18 C19 C16 109.8(5) .
C4 C5 C6 132.2(5) .
C4 C5 S2 117.8(4) .
C6 C5 S2 109.8(4) .
C12 C14 C11 110.4(5) .
C1 C9 C10 105.8(5) .
C1 C9 C11 106.0(5) .
C10 C9 C11 108.4(5) .
C10 C13 C12 109.6(5) .
C2 C1 C9 114.3(5) .
C2 C1 S1 114.7(5) .
C9 C1 S1 131.0(5) .
C15 C17 C20 111.1(5) .
C2 C12 C14 106.1(5) .
C2 C12 C13 108.3(6) .
C14 C12 C13 108.5(5) .
C13 C10 C9 111.3(6) .
C14 C11 C9 110.4(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F6 Sb1 1.832(8) .
F3 Sb1 1.863(6) .
F2 Sb1 1.903(6) .
F5 Sb1 1.764(7) .
F14 Sb1 1.909(16) .
F11 Sb1 1.694(16) .
F12 Sb1 1.72(2) .
F13 Sb1 1.958(18) .
Sb1 F1 1.841(4) .
Sb1 F4 1.847(4) .
S2 C5 1.730(6) .
S2 C8 1.733(6) .
S1 C1 1.668(6) .
S1 C4 1.743(6) .
C2 C1 1.372(8) .
C2 C3 1.385(8) .
C2 C12 1.485(8) .
C18 C7 1.485(8) .
C18 C19 1.523(8) .
C18 C20 1.527(9) .
C4 C5 1.383(7) .
C4 C3 1.388(8) .
C6 C7 1.358(7) .
C6 C5 1.408(8) .
C6 C15 1.497(8) .
C8 C8 1.390(11) 2_766
C8 C7 1.417(8) .
C20 C17 1.542(8) .
C15 C16 1.518(8) .
C15 C17 1.532(9) .
C16 C19 1.532(8) .
C14 C12 1.518(8) .
C14 C11 1.524(9) .
C9 C1 1.496(8) .
C9 C10 1.539(9) .
C9 C11 1.547(9) .
C13 C10 1.513(9) .
C13 C12 1.545(9) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 S1 C4 C5 178.5(5) . . .
C1 S1 C4 C3 -0.2(5) . . .
C1 C2 C3 C4 -0.4(8) . . .
C12 C2 C3 C4 179.8(7) . . .
C5 C4 C3 C2 -178.2(6) . . .
S1 C4 C3 C2 0.4(7) . . .
C5 S2 C8 C8 178.9(8) . . 2_766
C5 S2 C8 C7 -2.1(5) . . .
C7 C18 C20 C17 -59.3(6) . . .
C19 C18 C20 C17 56.7(6) . . .
C7 C6 C15 C16 58.9(7) . . .
C5 C6 C15 C16 -118.3(7) . . .
C7 C6 C15 C17 -56.5(7) . . .
C5 C6 C15 C17 126.2(7) . . .
C5 C6 C7 C8 -1.9(8) . . .
C15 C6 C7 C8 -179.6(6) . . .
C5 C6 C7 C18 177.9(5) . . .
C15 C6 C7 C18 0.2(8) . . .
C8 C8 C7 C6 -178.4(8) 2_766 . .
S2 C8 C7 C6 2.7(7) . . .
C8 C8 C7 C18 1.8(14) 2_766 . .
S2 C8 C7 C18 -177.1(6) . . .
C19 C18 C7 C6 -58.4(7) . . .
C20 C18 C7 C6 59.6(7) . . .
C19 C18 C7 C8 121.3(7) . . .
C20 C18 C7 C8 -120.6(8) . . .
C6 C15 C16 C19 -57.9(7) . . .
C17 C15 C16 C19 57.1(7) . . .
C7 C18 C19 C16 54.4(6) . . .
C20 C18 C19 C16 -61.8(6) . . .
C15 C16 C19 C18 2.9(7) . . .
C3 C4 C5 C6 -179.6(6) . . .
S1 C4 C5 C6 2.0(10) . . .
C3 C4 C5 S2 3.9(9) . . .
S1 C4 C5 S2 -174.6(3) . . .
C7 C6 C5 C4 -176.5(7) . . .
C15 C6 C5 C4 0.7(12) . . .
C7 C6 C5 S2 0.2(7) . . .
C15 C6 C5 S2 177.5(6) . . .
C8 S2 C5 C4 178.4(5) . . .
C8 S2 C5 C6 1.1(5) . . .
C3 C2 C1 C9 179.5(5) . . .
C12 C2 C1 C9 -0.7(8) . . .
C3 C2 C1 S1 0.3(8) . . .
C12 C2 C1 S1 -179.9(4) . . .
C10 C9 C1 C2 58.0(7) . . .
C11 C9 C1 C2 -57.0(7) . . .
C10 C9 C1 S1 -122.9(6) . . .
C11 C9 C1 S1 122.1(6) . . .
C4 S1 C1 C2 -0.1(5) . . .
C4 S1 C1 C9 -179.1(6) . . .
C6 C15 C17 C20 51.5(7) . . .
C16 C15 C17 C20 -61.9(7) . . .
C18 C20 C17 C15 4.5(7) . . .
C1 C2 C12 C14 59.5(7) . . .
C3 C2 C12 C14 -120.7(8) . . .
C1 C2 C12 C13 -56.8(7) . . .
C3 C2 C12 C13 123.0(8) . . .
C11 C14 C12 C2 -57.3(7) . . .
C11 C14 C12 C13 58.9(6) . . .
C10 C13 C12 C2 52.9(7) . . .
C10 C13 C12 C14 -61.8(7) . . .
C12 C13 C10 C9 3.4(8) . . .
C1 C9 C10 C13 -57.4(7) . . .
C11 C9 C10 C13 55.9(7) . . .
C12 C14 C11 C9 1.3(7) . . .
C1 C9 C11 C14 54.4(7) . . .
C10 C9 C11 C14 -58.7(6) . . .
S2 C8 C8 S2 180.0 . 2_766 2_766
C7 C8 C8 C7 180.000(1) . 2_766 2_766
