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#$Date: 2016-03-22 11:55:46 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178924 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/53/4115388.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_4115388
loop_
_publ_author_name
'Atsushi Wakamiya'
'Tohru Nishinaga'
'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
;
 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 H21 Cl6 O2 S2 Sb'
_chemical_formula_sum            'C16 H21 Cl6 O2 S2 Sb'
_chemical_formula_weight         643.90
_chemical_name_common            ' 1,2-dithiolium cation '
_chemical_name_systematic
; 
 ? 
;
_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             ' Wed July 17 2002 '
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.7860(10)
_cell_angle_beta                 92.8560(10)
_cell_angle_gamma                108.0530(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0312(6)
_cell_length_b                   11.1246(8)
_cell_length_c                   14.3052(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    100(2)
_cell_volume                     1142.25(14)
_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 0.964
_diffrn_measured_fraction_theta_max 0.964
_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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7893
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    2.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_description       prism
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.716
_refine_diff_density_min         -1.324
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         5077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0383
_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)+(0.0582P)²+1.9560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                4538
_reflns_number_total             5077
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja028297j-3_s2_3.cif
_cod_data_source_block           12dithiolium
_cod_database_code               4115388
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
Sb1 Sb 0.5000 0.5000 0.5000 0.01850(10) Uani 1 2 d S
Sb2 Sb 0.5000 0.5000 0.0000 0.01487(10) Uani 1 2 d S
Cl4 Cl 0.20712(11) 0.50211(9) 0.00193(8) 0.0241(2) Uani 1 1 d .
Cl5 Cl 0.60940(12) 0.73782(9) 0.06196(8) 0.0253(2) Uani 1 1 d .
Cl2 Cl 0.72463(18) 0.60214(16) 0.42095(10) 0.0562(4) Uani 1 1 d .
Cl3 Cl 0.2906(2) 0.55337(15) 0.41423(10) 0.0515(3) Uani 1 1 d .
Cl1 Cl 0.4351(2) 0.29735(12) 0.36692(10) 0.0514(3) Uani 1 1 d .
S1 S -0.04989(14) 0.09103(10) 0.39675(7) 0.0243(2) Uani 1 1 d .
S2 S -0.12565(15) 0.24781(11) 0.39584(7) 0.0276(2) Uani 1 1 d .
C13 C 0.2634(6) -0.2240(4) 0.2699(3) 0.0252(8) Uani 1 1 d .
H13 H 0.3112 -0.2991 0.2455 0.030 Uiso 1 1 calc R
C16 C 0.3651(5) -0.1341(5) 0.3723(3) 0.0278(9) Uani 1 1 d .
C2 C -0.0916(5) 0.1048(4) 0.2193(3) 0.0182(7) Uani 1 1 d .
C3 C -0.0468(5) 0.0309(4) 0.2724(3) 0.0183(7) Uani 1 1 d .
C7 C -0.0966(5) 0.0884(4) 0.1112(3) 0.0218(8) Uani 1 1 d .
H3 H -0.0662 0.0080 0.0740 0.026 Uiso 1 1 calc R
C1 C -0.1327(5) 0.2156(4) 0.2730(3) 0.0207(7) Uani 1 1 d .
C4 C -0.1753(6) 0.2965(4) 0.2144(3) 0.0245(8) Uani 1 1 d .
H5 H -0.2043 0.3748 0.2570 0.029 Uiso 1 1 calc R
C8 C -0.2837(6) 0.0772(4) 0.0695(3) 0.0276(9) Uani 1 1 d .
H8A H -0.2876 0.0750 -0.0003 0.033 Uiso 1 1 calc R
H8B H -0.3717 -0.0072 0.0705 0.033 Uiso 1 1 calc R
C6 C -0.0113(6) 0.3404(4) 0.1655(3) 0.0293(9) Uani 1 1 d .
H10A H 0.0905 0.4034 0.2176 0.035 Uiso 1 1 calc R
H10B H -0.0352 0.3881 0.1211 0.035 Uiso 1 1 calc R
C5 C -0.3306(6) 0.1980(4) 0.1326(3) 0.0297(9) Uani 1 1 d .
H7A H -0.3611 0.2450 0.0892 0.036 Uiso 1 1 calc R
H7B H -0.4357 0.1658 0.1633 0.036 Uiso 1 1 calc R
C9 C 0.0362(6) 0.2185(4) 0.1052(3) 0.0296(9) Uani 1 1 d .
H9A H 0.1577 0.2285 0.1318 0.036 Uiso 1 1 calc R
H9B H 0.0333 0.2140 0.0349 0.036 Uiso 1 1 calc R
C14 C 0.2918(6) -0.1446(4) 0.1979(3) 0.0246(8) Uani 1 1 d .
H11A H 0.4203 -0.1057 0.1971 0.030 Uiso 1 1 calc R
H11B H 0.2340 -0.2055 0.1299 0.030 Uiso 1 1 calc R
C15 C 0.2141(5) -0.0329(4) 0.2298(3) 0.0230(8) Uani 1 1 d .
H12A H 0.2326 0.0169 0.1823 0.028 Uiso 1 1 calc R
H12B H 0.2775 0.0307 0.2962 0.028 Uiso 1 1 calc R
Cl6 Cl 0.51576(13) 0.49747(10) 0.16390(7) 0.0270(2) Uani 1 1 d .
C10 C 0.0150(5) -0.0870(4) 0.2341(3) 0.0198(7) Uani 1 1 d .
H17 H -0.0489 -0.1407 0.1648 0.024 Uiso 1 1 calc R
C11 C -0.0255(5) -0.1790(4) 0.2972(3) 0.0227(8) Uani 1 1 d .
H18A H 0.0144 -0.1236 0.3683 0.027 Uiso 1 1 calc R
H18B H -0.1554 -0.2249 0.2876 0.027 Uiso 1 1 calc R
C12 C 0.0650(6) -0.2847(4) 0.2706(3) 0.0261(8) Uani 1 1 d .
H19A H 0.0480 -0.3328 0.3192 0.031 Uiso 1 1 calc R
H19B H 0.0076 -0.3513 0.2041 0.031 Uiso 1 1 calc R
O2 O 0.3005(4) -0.1131(3) 0.4479(2) 0.0322(7) Uani 1 1 d .
O1 O 0.5352(4) -0.0761(4) 0.3721(3) 0.0522(11) Uani 1 1 d .
H20 H 0.5814 -0.0161 0.4275 0.078 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_3
Cl1 Sb1 Cl1 180.00(5) 2_666 .
Cl1 Sb1 Cl2 88.77(5) 2_666 2_666
Cl1 Sb1 Cl2 91.23(5) . 2_666
Cl1 Sb1 Cl2 91.23(5) 2_666 .
Cl1 Sb1 Cl2 88.77(5) . .
Cl2 Sb1 Cl2 180.0 2_666 .
Cl1 Sb1 Cl3 88.93(5) 2_666 2_666
Cl1 Sb1 Cl3 91.07(5) . 2_666
Cl2 Sb1 Cl3 90.67(6) 2_666 2_666
Cl2 Sb1 Cl3 89.33(6) . 2_666
Cl1 Sb1 Cl3 91.07(5) 2_666 .
Cl1 Sb1 Cl3 88.93(5) . .
Cl2 Sb1 Cl3 89.33(6) 2_666 .
Cl2 Sb1 Cl3 90.67(6) . .
Cl3 Sb1 Cl3 180.0 2_666 .
Cl6 Sb2 Cl6 180.00(5) . 2_665
Cl6 Sb2 Cl4 89.97(3) . .
Cl6 Sb2 Cl4 90.03(3) 2_665 .
Cl6 Sb2 Cl4 90.03(3) . 2_665
Cl6 Sb2 Cl4 89.97(3) 2_665 2_665
Cl4 Sb2 Cl4 180.0 . 2_665
Cl6 Sb2 Cl5 89.76(4) . .
Cl6 Sb2 Cl5 90.24(4) 2_665 .
Cl4 Sb2 Cl5 89.84(3) . .
Cl4 Sb2 Cl5 90.16(3) 2_665 .
Cl6 Sb2 Cl5 90.24(4) . 2_665
Cl6 Sb2 Cl5 89.76(4) 2_665 2_665
Cl4 Sb2 Cl5 90.16(3) . 2_665
Cl4 Sb2 Cl5 89.84(3) 2_665 2_665
Cl5 Sb2 Cl5 180.0 . 2_665
C3 S1 S2 96.77(14) . .
C1 S2 S1 94.66(14) . .
C16 C13 C12 112.4(3) . .
C16 C13 C14 109.9(3) . .
C12 C13 C14 109.5(3) . .
O2 C16 O1 121.8(4) . .
O2 C16 C13 125.1(4) . .
O1 C16 C13 113.1(4) . .
C1 C2 C3 116.7(3) . .
C1 C2 C7 112.8(3) . .
C3 C2 C7 130.4(3) . .
C2 C3 C10 127.6(3) . .
C2 C3 S1 114.4(3) . .
C10 C3 S1 117.9(3) . .
C2 C7 C9 106.8(3) . .
C2 C7 C8 107.9(3) . .
C9 C7 C8 107.9(3) . .
C2 C1 C4 115.8(3) . .
C2 C1 S2 117.5(3) . .
C4 C1 S2 126.7(3) . .
C1 C4 C5 105.7(3) . .
C1 C4 C6 105.6(3) . .
C5 C4 C6 108.6(3) . .
C5 C8 C7 109.9(3) . .
C4 C6 C9 111.0(3) . .
C4 C5 C8 111.1(3) . .
C6 C9 C7 110.0(3) . .
C15 C14 C13 110.2(3) . .
C14 C15 C10 112.1(3) . .
C3 C10 C11 112.2(3) . .
C3 C10 C15 108.1(3) . .
C11 C10 C15 112.0(3) . .
C12 C11 C10 112.6(3) . .
C13 C12 C11 112.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sb1 Cl1 2.3514(12) 2_666
Sb1 Cl1 2.3514(12) .
Sb1 Cl2 2.3542(12) 2_666
Sb1 Cl2 2.3542(12) .
Sb1 Cl3 2.3544(13) 2_666
Sb1 Cl3 2.3544(13) .
Sb2 Cl6 2.3509(10) .
Sb2 Cl6 2.3509(10) 2_665
Sb2 Cl4 2.3610(9) .
Sb2 Cl4 2.3610(9) 2_665
Sb2 Cl5 2.3677(9) .
Sb2 Cl5 2.3677(9) 2_665
S1 C3 1.703(4) .
S1 S2 2.0206(15) .
S2 C1 1.677(4) .
C13 C16 1.513(6) .
C13 C12 1.528(6) .
C13 C14 1.532(6) .
C16 O2 1.213(5) .
C16 O1 1.318(5) .
C2 C1 1.385(5) .
C2 C3 1.385(5) .
C2 C7 1.497(5) .
C3 C10 1.503(5) .
C7 C9 1.539(6) .
C7 C8 1.542(6) .
C1 C4 1.502(5) .
C4 C5 1.533(6) .
C4 C6 1.537(6) .
C8 C5 1.540(6) .
C6 C9 1.539(6) .
C14 C15 1.517(5) .
C15 C10 1.536(5) .
C10 C11 1.535(5) .
C11 C12 1.530(5) .
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
C3 S1 S2 C1 -0.66(18)
C12 C13 C16 O2 1.5(6)
C14 C13 C16 O2 123.7(5)
C12 C13 C16 O1 -177.0(4)
C14 C13 C16 O1 -54.8(5)
C1 C2 C3 C10 -175.5(3)
C7 C2 C3 C10 1.7(6)
C1 C2 C3 S1 -0.1(4)
C7 C2 C3 S1 177.0(3)
S2 S1 C3 C2 0.5(3)
S2 S1 C3 C10 176.4(3)
C1 C2 C7 C9 58.0(4)
C3 C2 C7 C9 -119.2(4)
C1 C2 C7 C8 -57.7(4)
C3 C2 C7 C8 125.0(4)
C3 C2 C1 C4 178.1(3)
C7 C2 C1 C4 0.5(5)
C3 C2 C1 S2 -0.5(5)
C7 C2 C1 S2 -178.2(3)
S1 S2 C1 C2 0.8(3)
S1 S2 C1 C4 -177.8(3)
C2 C1 C4 C5 57.2(4)
S2 C1 C4 C5 -124.3(3)
C2 C1 C4 C6 -57.8(4)
S2 C1 C4 C6 120.8(3)
C2 C7 C8 C5 54.0(4)
C9 C7 C8 C5 -61.1(4)
C1 C4 C6 C9 54.4(4)
C5 C4 C6 C9 -58.5(4)
C1 C4 C5 C8 -56.3(4)
C6 C4 C5 C8 56.5(4)
C7 C8 C5 C4 2.8(5)
C4 C6 C9 C7 0.5(5)
C2 C7 C9 C6 -56.7(4)
C8 C7 C9 C6 59.1(4)
C16 C13 C14 C15 -64.3(4)
C12 C13 C14 C15 59.7(4)
C13 C14 C15 C10 -58.4(4)
C2 C3 C10 C11 -154.8(4)
S1 C3 C10 C11 30.0(4)
C2 C3 C10 C15 81.3(5)
S1 C3 C10 C15 -94.0(3)
C14 C15 C10 C3 176.4(3)
C14 C15 C10 C11 52.3(4)
C3 C10 C11 C12 -169.8(3)
C15 C10 C11 C12 -48.1(4)
C16 C13 C12 C11 66.0(4)
C14 C13 C12 C11 -56.5(4)
C10 C11 C12 C13 51.1(5)
