# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2002

data_nof 
_database_code_CSD                  180852

_journal_coden_Cambridge      182


_publ_requested_journal       'Chemical Communications'

loop_
_publ_author_name
'Komatsu, Koichi'
'Nishinaga, Tohru'
'Wakamiya, Atsushi'

_publ_contact_author_name     	'Prof Koichi Komatsu'  
_publ_contact_author_address 
;
Prof Koichi Komatsu
Institute for Chemical Research
Kyoto University
Gokasho
Uji
Kyoto
611-0011
JAPAN
;

_publ_contact_author_email       'KOMATSU@SCL.KYOTO-U.AC.JP'

_publ_section_title
;
The stable radical cation of thiophene annelated with
bicyclo[2.2.2]octene and its reaction with triplet oxygen to give a
protonated cation of 2-butene-1,4-dione derivative
;




_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
? 
; 

_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C16 H21 O2 Sb' 
_chemical_formula_sum 
'C16 H21 F6 O2 Sb' 
_chemical_formula_weight          481.08 

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' 
'O'  'O'   0.0106   0.0060 
'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' 
'Sb'  'Sb'  -0.5866   1.5461 
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

_symmetry_cell_setting            Orthorhombic 
_symmetry_space_group_name_H-M    P2(1)2(1)2(1) 

loop_ 
_symmetry_equiv_pos_as_xyz 
'x, y, z' 
'-x+1/2, -y, z+1/2' 
'-x, y+1/2, -z+1/2' 
'x+1/2, -y+1/2, -z' 

_cell_length_a                    7.2353(5) 
_cell_length_b                    14.7165(11) 
_cell_length_c                    16.5155(13) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1758.5(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     123(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 

_exptl_crystal_description        prism 
_exptl_crystal_colour             paleyellow 
_exptl_crystal_size_max           0.40 
_exptl_crystal_size_mid           0.40 
_exptl_crystal_size_min           0.40 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.817 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              952 
_exptl_absorpt_coefficient_mu     1.636 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 

_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       123(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             10209 
_diffrn_reflns_av_R_equivalents   0.0277 
_diffrn_reflns_av_sigmaI/netI     0.0224 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -17 
_diffrn_reflns_limit_k_max        8 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          1.85 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              3104 
_reflns_number_gt                 3055 
_reflns_threshold_expression      >2sigma(I) 

_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SHELXTL' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 

_refine_special_details 
; 
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
goodness of fit S are based on F^2^, conventional R-factors R are based 
on F, with F set to zero for negative F^2^. The threshold expression of 
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F^2^ are statistically about twice as large as those based on F, and R- 
factors based on ALL data will be even larger. 
; 

_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'calc w=1/[\s^2^(Fo^2^)+(0.0357P)^2^+0.0408P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    -0.009(17) 
_refine_ls_number_reflns          3104 
_refine_ls_number_parameters      230 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0216 
_refine_ls_R_factor_gt            0.0211 
_refine_ls_wR_factor_ref          0.0510 
_refine_ls_wR_factor_gt           0.0508 
_refine_ls_goodness_of_fit_ref    1.047 
_refine_ls_restrained_S_all       1.046 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 

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 
H2 H 1.095(7) 0.242(3) 0.2302(13) 0.087(15) Uiso 1 1 d D . . 
C1 C 0.9145(4) 0.26447(18) 0.31730(17) 0.0236(6) Uani 1 1 d . . . 
C2 C 0.7719(4) 0.20995(18) 0.27413(15) 0.0223(5) Uani 1 1 d . . . 
C3 C 0.7919(4) 0.16936(18) 0.20100(15) 0.0225(6) Uani 1 1 d . . . 
C4 C 0.9555(4) 0.17448(17) 0.14744(17) 0.0241(6) Uani 1 1 d . . . 
C5 C 0.8512(4) 0.30179(18) 0.39626(15) 0.0258(6) Uani 1 1 d . . . 
H5 H 0.9524 0.3369 0.4231 0.031 Uiso 1 1 calc R . . 
C6 C 0.5969(4) 0.20922(19) 0.32344(16) 0.0241(6) Uani 1 1 d . . . 
H6 H 0.4996 0.1732 0.2948 0.029 Uiso 1 1 calc R . . 
C7 C 0.6393(4) 0.1158(2) 0.15916(16) 0.0301(6) Uani 1 1 d . . . 
H7 H 0.5299 0.1091 0.1957 0.036 Uiso 1 1 calc R . . 
C8 C 0.9248(4) 0.1335(2) 0.06564(17) 0.0302(6) Uani 1 1 d . . . 
H8 H 1.0366 0.1415 0.0307 0.036 Uiso 1 1 calc R . . 
C9 C 0.7880(4) 0.2219(2) 0.45034(16) 0.0289(6) Uani 1 1 d . . . 
H9A H 0.8949 0.1823 0.4628 0.035 Uiso 1 1 calc R . . 
H9B H 0.7383 0.2457 0.5020 0.035 Uiso 1 1 calc R . . 
C10 C 0.6832(4) 0.36375(18) 0.37855(17) 0.0279(6) Uani 1 1 d . . . 
H10A H 0.7219 0.4153 0.3439 0.033 Uiso 1 1 calc R . . 
H10B H 0.6340 0.3886 0.4299 0.033 Uiso 1 1 calc R . . 
C11 C 0.6378(4) 0.16652(18) 0.40634(16) 0.0279(6) Uani 1 1 d . . . 
H11A H 0.6804 0.1031 0.3990 0.033 Uiso 1 1 calc R . . 
H11B H 0.5236 0.1655 0.4394 0.033 Uiso 1 1 calc R . . 
C12 C 0.5312(4) 0.3078(2) 0.33495(17) 0.0280(6) Uani 1 1 d . . . 
H12A H 0.4163 0.3086 0.3675 0.034 Uiso 1 1 calc R . . 
H12B H 0.5040 0.3354 0.2816 0.034 Uiso 1 1 calc R . . 
C13 C 0.7152(5) 0.0219(2) 0.13486(18) 0.0388(7) Uani 1 1 d . . . 
H13A H 0.7517 -0.0121 0.1841 0.047 Uiso 1 1 calc R . . 
H13B H 0.6174 -0.0132 0.1069 0.047 Uiso 1 1 calc R . . 
C14 C 0.5861(4) 0.1678(2) 0.08171(19) 0.0370(7) Uani 1 1 d . . . 
H14A H 0.4899 0.1337 0.0518 0.044 Uiso 1 1 calc R . . 
H14B H 0.5348 0.2280 0.0963 0.044 Uiso 1 1 calc R . . 
C15 C 0.8833(4) 0.03191(19) 0.07862(18) 0.0360(7) Uani 1 1 d . . . 
H15A H 0.8573 0.0025 0.0259 0.043 Uiso 1 1 calc R . . 
H15B H 0.9920 0.0016 0.1031 0.043 Uiso 1 1 calc R . . 
C16 C 0.7572(4) 0.1802(2) 0.02770(18) 0.0348(7) Uani 1 1 d . . . 
H16A H 0.7329 0.1538 -0.0264 0.042 Uiso 1 1 calc R . . 
H16B H 0.7831 0.2458 0.0208 0.042 Uiso 1 1 calc R . . 
F1 F 0.8341(3) 0.36835(12) 0.15408(17) 0.0711(7) Uani 1 1 d . . . 
F2 F 0.8225(3) 0.61886(12) 0.12045(15) 0.0588(6) Uani 1 1 d . . . 
F3 F 0.5947(3) 0.49745(15) 0.18329(17) 0.0772(8) Uani 1 1 d . . . 
F4 F 1.0620(3) 0.49046(16) 0.09012(19) 0.0828(8) Uani 1 1 d . . . 
F5 F 0.9337(5) 0.5115(2) 0.23842(14) 0.1073(11) Uani 1 1 d . . . 
F6 F 0.7281(4) 0.4762(2) 0.03585(14) 0.0912(9) Uani 1 1 d . . . 
O1 O 1.0736(3) 0.28104(13) 0.29299(11) 0.0295(4) Uani 1 1 d D . . 
O2 O 1.1071(3) 0.21117(14) 0.16406(13) 0.0299(5) Uani 1 1 d D . . 
Sb1 Sb 0.82823(2) 0.493214(11) 0.137097(9) 0.02368(7) Uani 1 1 d . . . 

loop_ 
_atom_site_aniso_label 
_atom_site_aniso_U_11 
_atom_site_aniso_U_22 
_atom_site_aniso_U_33 
_atom_site_aniso_U_23 
_atom_site_aniso_U_13 
_atom_site_aniso_U_12 
C1 0.0235(14) 0.0186(14) 0.0286(14) 0.0044(12) -0.0013(12) 0.0014(11) 
C2 0.0244(13) 0.0166(13) 0.0261(13) 0.0021(11) -0.0035(11) -0.0001(10) 
C3 0.0257(14) 0.0197(13) 0.0220(13) 0.0012(10) -0.0002(10) -0.0015(11) 
C4 0.0288(14) 0.0144(12) 0.0290(14) 0.0000(11) 0.0016(12) 0.0015(10) 
C5 0.0281(15) 0.0248(13) 0.0246(13) -0.0038(11) -0.0042(12) -0.0046(13) 
C6 0.0242(13) 0.0257(15) 0.0225(12) -0.0018(12) -0.0002(10) -0.0034(11) 
C7 0.0287(14) 0.0336(15) 0.0280(14) -0.0048(12) 0.0015(11) -0.0131(13) 
C8 0.0351(15) 0.0298(16) 0.0258(15) -0.0059(12) 0.0072(12) -0.0012(13) 
C9 0.0297(15) 0.0304(16) 0.0265(14) 0.0014(12) -0.0012(11) 0.0038(12) 
C10 0.0304(14) 0.0232(13) 0.0301(14) -0.0035(11) -0.0018(11) 0.0035(12) 
C11 0.0331(15) 0.0262(13) 0.0243(13) 0.0023(11) 0.0037(12) -0.0014(12) 
C12 0.0254(14) 0.0302(15) 0.0285(14) -0.0009(12) -0.0025(11) 0.0041(12) 
C13 0.0531(18) 0.0282(16) 0.0351(15) -0.0034(13) -0.0035(13) -0.0150(14) 
C14 0.0361(15) 0.0440(19) 0.0308(15) -0.0067(15) -0.0077(13) 0.0014(14) 
C15 0.0459(17) 0.0231(14) 0.0389(15) -0.0087(13) -0.0047(13) 0.0028(13) 
C16 0.0440(17) 0.0330(17) 0.0275(14) 0.0043(13) 0.0018(14) 0.0016(13) 
F1 0.0650(13) 0.0209(9) 0.127(2) 0.0128(11) 0.0019(16) 0.0032(10) 
F2 0.0596(12) 0.0203(8) 0.0964(16) 0.0096(9) 0.0161(13) -0.0025(9) 
F3 0.0517(12) 0.0496(14) 0.130(2) 0.0228(17) 0.0500(14) 0.0097(12) 
F4 0.0440(12) 0.0553(14) 0.149(2) -0.0161(18) 0.0373(14) -0.0054(12) 
F5 0.154(3) 0.118(2) 0.0503(13) 0.0134(17) -0.0537(15) -0.051(2) 
F6 0.124(2) 0.107(2) 0.0424(12) 0.0017(13) -0.0347(13) -0.0585(18) 
O1 0.0221(10) 0.0317(11) 0.0347(11) -0.0007(9) -0.0016(8) -0.0049(8) 
O2 0.0203(10) 0.0299(11) 0.0397(12) 0.0022(9) 0.0053(8) -0.0025(8) 
Sb1 0.02682(10) 0.01849(9) 0.02572(10) -0.00036(7) -0.00272(6) -0.00087(8) 

_geom_special_details 
; 
All esds (except the esd in the dihedral angle between two l.s. planes) 
are estimated using the full covariance matrix.  The cell esds are taken 
into account individually in the estimation of esds in distances, angles 
and torsion angles; correlations between esds in cell parameters are only 
used when they are defined by crystal symmetry.  An approximate (isotropic) 
treatment of cell esds is used for estimating esds involving l.s. planes. 
; 

loop_ 
_geom_bond_atom_site_label_1 
_geom_bond_atom_site_label_2 
_geom_bond_distance 
_geom_bond_site_symmetry_2 
_geom_bond_publ_flag 
C1 O1 1.243(3) . ? 
C1 C5 1.487(4) . ? 
C1 C2 1.489(4) . ? 
C2 C3 1.355(4) . ? 
C2 C6 1.506(4) . ? 
C3 C4 1.480(4) . ? 
C3 C7 1.522(4) . ? 
C4 O2 1.253(3) . ? 
C4 C8 1.496(4) . ? 
C5 C9 1.545(4) . ? 
C5 C10 1.547(4) . ? 
C6 C11 1.535(4) . ? 
C6 C12 1.539(4) . ? 
C7 C14 1.540(4) . ? 
C7 C13 1.541(4) . ? 
C8 C16 1.528(4) . ? 
C8 C15 1.540(4) . ? 
C9 C11 1.541(4) . ? 
C10 C12 1.551(4) . ? 
C13 C15 1.537(4) . ? 
C14 C16 1.537(4) . ? 
F1 Sb1 1.8593(18) . ? 
F2 Sb1 1.8698(18) . ? 
F3 Sb1 1.8548(19) . ? 
F4 Sb1 1.861(2) . ? 
F5 Sb1 1.859(2) . ? 
F6 Sb1 1.839(2) . ? 

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 
_geom_angle_publ_flag 
O1 C1 C5 119.7(2) . . ? 
O1 C1 C2 126.4(3) . . ? 
C5 C1 C2 113.9(2) . . ? 
C3 C2 C1 126.2(3) . . ? 
C3 C2 C6 124.6(2) . . ? 
C1 C2 C6 109.1(2) . . ? 
C2 C3 C4 126.5(2) . . ? 
C2 C3 C7 123.8(2) . . ? 
C4 C3 C7 109.6(2) . . ? 
O2 C4 C3 126.3(2) . . ? 
O2 C4 C8 120.1(2) . . ? 
C3 C4 C8 113.6(2) . . ? 
C1 C5 C9 108.5(2) . . ? 
C1 C5 C10 107.1(2) . . ? 
C9 C5 C10 109.0(2) . . ? 
C2 C6 C11 108.8(2) . . ? 
C2 C6 C12 108.7(2) . . ? 
C11 C6 C12 109.6(2) . . ? 
C3 C7 C14 107.5(2) . . ? 
C3 C7 C13 108.9(2) . . ? 
C14 C7 C13 108.6(2) . . ? 
C4 C8 C16 107.9(2) . . ? 
C4 C8 C15 107.1(2) . . ? 
C16 C8 C15 109.8(2) . . ? 
C11 C9 C5 109.8(2) . . ? 
C5 C10 C12 109.4(2) . . ? 
C6 C11 C9 109.9(2) . . ? 
C6 C12 C10 109.8(2) . . ? 
C15 C13 C7 110.7(2) . . ? 
C16 C14 C7 109.8(2) . . ? 
C13 C15 C8 109.4(2) . . ? 
C8 C16 C14 110.4(2) . . ? 
F6 Sb1 F3 91.13(14) . . ? 
F6 Sb1 F5 178.82(13) . . ? 
F3 Sb1 F5 89.93(14) . . ? 
F6 Sb1 F1 90.67(13) . . ? 
F3 Sb1 F1 89.53(10) . . ? 
F5 Sb1 F1 89.87(13) . . ? 
F6 Sb1 F4 88.63(14) . . ? 
F3 Sb1 F4 179.24(11) . . ? 
F5 Sb1 F4 90.31(14) . . ? 
F1 Sb1 F4 91.19(11) . . ? 
F6 Sb1 F2 89.55(13) . . ? 
F3 Sb1 F2 90.41(10) . . ? 
F5 Sb1 F2 89.91(13) . . ? 
F1 Sb1 F2 179.77(12) . . ? 
F4 Sb1 F2 88.87(10) . . ? 

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_2 
_geom_torsion_site_symmetry_3 
_geom_torsion_site_symmetry_4 
_geom_torsion_publ_flag 
O1 C1 C2 C3 -0.1(5) . . . . ? 
C5 C1 C2 C3 179.1(2) . . . . ? 
O1 C1 C2 C6 -178.2(3) . . . . ? 
C5 C1 C2 C6 1.0(3) . . . . ? 
C1 C2 C3 C4 -3.1(4) . . . . ? 
C6 C2 C3 C4 174.7(3) . . . . ? 
C1 C2 C3 C7 -178.8(2) . . . . ? 
C6 C2 C3 C7 -1.0(4) . . . . ? 
C2 C3 C4 O2 6.1(5) . . . . ? 
C7 C3 C4 O2 -177.7(2) . . . . ? 
C2 C3 C4 C8 -171.6(2) . . . . ? 
C7 C3 C4 C8 4.6(3) . . . . ? 
O1 C1 C5 C9 -123.3(3) . . . . ? 
C2 C1 C5 C9 57.4(3) . . . . ? 
O1 C1 C5 C10 119.2(3) . . . . ? 
C2 C1 C5 C10 -60.0(3) . . . . ? 
C3 C2 C6 C11 121.8(3) . . . . ? 
C1 C2 C6 C11 -60.1(3) . . . . ? 
C3 C2 C6 C12 -118.9(3) . . . . ? 
C1 C2 C6 C12 59.2(3) . . . . ? 
C2 C3 C7 C14 114.4(3) . . . . ? 
C4 C3 C7 C14 -62.0(3) . . . . ? 
C2 C3 C7 C13 -128.1(3) . . . . ? 
C4 C3 C7 C13 55.6(3) . . . . ? 
O2 C4 C8 C16 -122.0(3) . . . . ? 
C3 C4 C8 C16 55.8(3) . . . . ? 
O2 C4 C8 C15 119.8(3) . . . . ? 
C3 C4 C8 C15 -62.3(3) . . . . ? 
C1 C5 C9 C11 -56.0(3) . . . . ? 
C10 C5 C9 C11 60.3(3) . . . . ? 
C1 C5 C10 C12 57.7(3) . . . . ? 
C9 C5 C10 C12 -59.5(3) . . . . ? 
C2 C6 C11 C9 59.5(3) . . . . ? 
C12 C6 C11 C9 -59.2(3) . . . . ? 
C5 C9 C11 C6 -0.9(3) . . . . ? 
C2 C6 C12 C10 -59.1(3) . . . . ? 
C11 C6 C12 C10 59.7(3) . . . . ? 
C5 C10 C12 C6 -0.1(3) . . . . ? 
C3 C7 C13 C15 -58.4(3) . . . . ? 
C14 C7 C13 C15 58.4(3) . . . . ? 
C3 C7 C14 C16 57.4(3) . . . . ? 
C13 C7 C14 C16 -60.4(3) . . . . ? 
C7 C13 C15 C8 1.0(3) . . . . ? 
C4 C8 C15 C13 57.3(3) . . . . ? 
C16 C8 C15 C13 -59.6(3) . . . . ? 
C4 C8 C16 C14 -58.7(3) . . . . ? 
C15 C8 C16 C14 57.8(3) . . . . ? 
C7 C14 C16 C8 2.5(4) . . . . ? 

_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    0.561 
_refine_diff_density_min   -0.387 
_refine_diff_density_rms    0.060