#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/8/8000056.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_8000056
_journal_name_full             'Chemistry Letters'
_journal_year                  2005
_journal_volume                34
_journal_page_first            966
_publ_section_title
;
 A Bromine Adduct of 2,3,6,7,14,15-Hexamethyl-9,10-distibatriptycene.
 The First Stibonium--Stiborate Zwitterion
;
_chemical_formula_sum 'C27 H24 F3 Sb2'
loop_
_publ_author_name
 'Yosuke Uchiyama'
 'Gaku Yamamoto'
_cell_measurement_temperature  113(2)
_diffrn_ambient_temperature    113(2)
_cell_length_a       26.4096(10)
_cell_length_b       10.1131(2)
_cell_length_c       20.5028(9)
_cell_angle_alpha    90.0000(4)
_cell_angle_beta     116.9319(5)
_cell_angle_gamma    90.0000(4)
_cell_volume          4882.06
_symmetry_space_group_name_H-M    'C 2/c'
loop_
_symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
Sb1 1 0.325468(7) -0.227256(16) 0.092838(9) 1 0.01152(6) Uani d .
Sb2 1 0.411969(7) 0.032471(15) 0.221700(8) 1 0.01130(6) Uani d .
C3 1 0.46990(11) -0.2118(2) 0.31595(14) 1 0.0131(5) Uani d .
H1 1 0.4919 -0.1454 0.3496 1 0.016 Uiso calc R
C4 1 0.28608(14) 0.2389(3) -0.0314(2) 1 0.0330(7) Uani d .
C5 1 0.46179(13) -0.5873(3) 0.30444(17) 1 0.0248(6) Uani d .
H2 1 0.5008 -0.6073 0.3137 1 0.037 Uiso calc R
H3 1 0.4352 -0.6411 0.2634 1 0.037 Uiso calc R
H4 1 0.4572 -0.6075 0.3483 1 0.037 Uiso calc R
C6 1 0.39811(14) -0.0142(3) -0.10091(16) 1 0.0272(7) Uani d .
H5 1 0.3781 0.0633 -0.1299 1 0.041 Uiso calc R
H6 1 0.3773 -0.0946 -0.1249 1 0.041 Uiso calc R
H7 1 0.4365 -0.0178 -0.0969 1 0.041 Uiso calc R
F1 1 0.27892(10) 0.4040(2) 0.12033(12) 1 0.0514(6) Uani d .
C8 1 0.40599(11) -0.4046(3) 0.21798(14) 1 0.0160(5) Uani d .
H8 1 0.3839 -0.4709 0.1843 1 0.019 Uiso calc R
C9 1 0.42652(10) -0.1744(2) 0.24804(14) 1 0.0121(5) Uani d .
C10 1 0.44962(11) -0.4424(2) 0.28578(15) 1 0.0158(5) Uani d .
C11 1 0.43625(11) 0.1008(2) 0.09226(14) 1 0.0138(5) Uani d .
H9 1 0.4588 0.1672 0.1256 1 0.017 Uiso calc R
C12 1 0.37313(10) -0.0851(2) 0.06509(13) 1 0.0131(5) Uani d .
C13 1 0.28905(11) -0.0800(2) 0.13469(14) 1 0.0139(5) Uani d .
F3 1 0.32132(9) 0.2282(2) -0.06178(13) 1 0.0454(5) Uani d .
F2 1 0.35048(8) 0.3816(2) 0.05854(13) 1 0.0515(6) Uani d .
C16 1 0.14221(14) -0.0185(4) 0.1218(2) 1 0.0421(9) Uani d .
H10 1 0.1269 -0.0925 0.0875 1 0.063 Uiso calc R
H11 1 0.1221 0.0629 0.0983 1 0.063 Uiso calc R
H12 1 0.1372 -0.0361 0.1655 1 0.063 Uiso calc R
C17 1 0.40178(12) -0.0039(3) -0.02559(14) 1 0.0181(5) Uani d .
C18 1 0.20485(12) -0.0026(3) 0.14350(17) 1 0.0244(6) Uani d .
C20 1 0.23079(11) -0.0867(3) 0.11400(15) 1 0.0178(5) Uani d .
H13 1 0.2083 -0.1505 0.0788 1 0.021 Uiso calc R
C21 1 0.46680(13) 0.1937(3) 0.00136(16) 1 0.0255(6) Uani d .
H14 1 0.4941 0.1471 -0.0105 1 0.038 Uiso calc R
H15 1 0.4871 0.2553 0.0418 1 0.038 Uiso calc R
H16 1 0.4400 0.2430 -0.0416 1 0.038 Uiso calc R
C22 1 0.40603(10) 0.0131(2) 0.11406(13) 1 0.0125(5) Uani d .
C23 1 0.29496(11) 0.1046(3) 0.21150(14) 1 0.0182(5) Uani d .
H17 1 0.3168 0.1728 0.2439 1 0.022 Uiso calc R
C24 1 0.37184(11) -0.0914(3) -0.00356(14) 1 0.0159(5) Uani d .
H18 1 0.3496 -0.1582 -0.0367 1 0.019 Uiso calc R
C25 1 0.39418(11) -0.2722(2) 0.19865(14) 1 0.0129(5) Uani d .
C26 1 0.23726(12) 0.0951(3) 0.19290(16) 1 0.0240(6) Uani d .
C27 1 0.32160(11) 0.0171(2) 0.18404(14) 1 0.0141(5) Uani d .
C29 1 0.43467(11) 0.0947(3) 0.02355(15) 1 0.0177(5) Uani d .
C30 1 0.48161(10) -0.3450(3) 0.33546(14) 1 0.0147(5) Uani d .
C31 1 0.52926(11) -0.3824(3) 0.40965(15) 1 0.0190(5) Uani d .
H19 1 0.5134 -0.4285 0.4383 1 0.029 Uiso calc R
H20 1 0.5490 -0.3023 0.4356 1 0.029 Uiso calc R
H21 1 0.5562 -0.4407 0.4029 1 0.029 Uiso calc R
C32 1 0.26477(14) 0.3285(3) 0.06099(19) 1 0.0340(8) Uani d .
C33 1 0.21194(15) 0.1878(4) 0.2281(2) 1 0.0418(9) Uani d .
H22 1 0.1766 0.2254 0.1904 1 0.063 Uiso calc R
H23 1 0.2389 0.2592 0.2531 1 0.063 Uiso calc R
H24 1 0.2039 0.1389 0.2637 1 0.063 Uiso calc R
C35 1 0.30107(13) 0.3174(3) 0.0304(2) 1 0.0341(8) Uani 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
Sb1 0.01282(10) 0.01037(10) 0.01004(9) -0.00236(6) 0.00402(7) -0.00165(6)
Sb2 0.01537(10) 0.00838(10) 0.00850(9) -0.00125(5) 0.00396(7) -0.00102(6)
C3 0.0156(12) 0.0126(12) 0.0132(12) -0.0004(9) 0.0085(11) -0.0016(9)
C4 0.0263(16) 0.0255(16) 0.041(2) 0.0029(14) 0.0100(15) 0.0061(13)
C5 0.0291(15) 0.0126(13) 0.0291(16) 0.0050(11) 0.0100(13) 0.0040(11)
C6 0.0371(17) 0.0318(17) 0.0151(14) -0.0019(12) 0.0139(13) -0.0077(13)
F1 0.0535(13) 0.0448(13) 0.0425(13) -0.0181(10) 0.0101(11) -0.0078(10)
C8 0.0191(13) 0.0084(12) 0.0223(14) -0.0021(10) 0.0109(12) -0.0021(9)
C9 0.0151(12) 0.0092(11) 0.0141(12) 0.0016(9) 0.0084(10) 0.0010(9)
C10 0.0193(13) 0.0112(12) 0.0200(13) 0.0040(10) 0.0116(11) 0.0032(10)
C11 0.0164(12) 0.0104(12) 0.0111(12) 0.0004(9) 0.0033(10) 0.0003(9)
C12 0.0154(12) 0.0119(12) 0.0115(12) 0.0017(9) 0.0057(10) 0.0014(9)
C13 0.0168(12) 0.0134(12) 0.0121(12) 0.0017(9) 0.0070(10) 0.0023(10)
F3 0.0372(11) 0.0419(12) 0.0572(15) 0.0028(10) 0.0214(11) 0.0090(9)
F2 0.0301(11) 0.0472(13) 0.0627(16) -0.0147(11) 0.0082(11) -0.0130(9)
C16 0.0210(16) 0.053(2) 0.055(2) -0.0186(19) 0.0203(17) -0.0015(15)
C17 0.0212(13) 0.0208(13) 0.0110(13) 0.0019(10) 0.0061(11) 0.0017(11)
C18 0.0190(14) 0.0300(15) 0.0261(16) -0.0016(13) 0.0118(13) 0.0044(12)
C20 0.0185(13) 0.0190(13) 0.0166(13) -0.0012(10) 0.0085(11) -0.0003(10)
C21 0.0297(16) 0.0276(16) 0.0196(15) 0.0037(12) 0.0116(13) -0.0072(12)
C22 0.0133(12) 0.0134(12) 0.0086(12) 0.0020(9) 0.0030(10) 0.0017(9)
C23 0.0229(13) 0.0176(13) 0.0126(12) -0.0026(10) 0.0069(11) 0.0036(11)
C24 0.0192(13) 0.0141(13) 0.0116(12) -0.0011(9) 0.0044(11) -0.0006(10)
C25 0.0131(12) 0.0133(12) 0.0128(12) 0.0005(9) 0.0062(10) -0.0006(9)
C26 0.0250(14) 0.0254(15) 0.0232(15) -0.0049(12) 0.0122(13) 0.0072(12)
C27 0.0171(12) 0.0136(12) 0.0105(12) 0.0019(9) 0.0054(10) 0.0032(10)
C29 0.0203(13) 0.0154(13) 0.0155(13) 0.0033(10) 0.0063(11) -0.0015(10)
C30 0.0123(11) 0.0166(13) 0.0147(13) 0.0026(10) 0.0057(10) 0.0011(10)
C31 0.0195(13) 0.0198(14) 0.0167(13) 0.0060(11) 0.0072(11) 0.0052(11)
C32 0.0304(17) 0.0245(17) 0.0330(18) -0.0047(14) 0.0019(15) 0.0018(13)
C33 0.0332(18) 0.052(2) 0.046(2) -0.0202(18) 0.0236(17) 0.0076(16)
C35 0.0239(16) 0.0205(16) 0.047(2) 0.0033(14) 0.0069(15) 0.0000(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Sb1 C12 2.150(2)
Sb1 C13 2.151(2)
Sb1 C25 2.154(3)
Sb2 C22 2.149(2)
Sb2 C9 2.151(2)
Sb2 C27 2.156(3)
C3 C9 1.396(4)
C3 C30 1.399(4)
C3 H1 0.9500
C4 F3 1.339(4)
C4 C32 1.378(5)
C4 C35 1.391(5)
C5 C10 1.513(4)
C5 H2 0.9800
C5 H3 0.9800
C5 H4 0.9800
C6 C17 1.506(4)
C6 H5 0.9800
C6 H6 0.9800
C6 H7 0.9800
F1 C32 1.338(4)
C8 C25 1.391(4)
C8 C10 1.398(4)
C8 H8 0.9500
C9 C25 1.396(3)
C10 C30 1.393(4)
C11 C29 1.392(4)
C11 C22 1.395(3)
C11 H9 0.9500
C12 C24 1.394(3)
C12 C22 1.400(3)
C13 C27 1.392(4)
C13 C20 1.400(4)
F2 C35 1.332(4)
C16 C18 1.514(4)
C16 H10 0.9800
C16 H11 0.9800
C16 H12 0.9800
C17 C24 1.391(4)
C17 C29 1.404(4)
C18 C20 1.390(4)
C18 C26 1.396(4)
C20 H13 0.9500
C21 C29 1.509(4)
C21 H14 0.9800
C21 H15 0.9800
C21 H16 0.9800
C23 C26 1.396(4)
C23 C27 1.398(4)
C23 H17 0.9500
C24 H18 0.9500
C26 C33 1.511(4)
C30 C31 1.519(4)
C31 H19 0.9800
C31 H20 0.9800
C31 H21 0.9800
C32 C35 1.368(5)
C32 C4 1.378(5)
C33 H22 0.9800
C33 H23 0.9800
C33 H24 0.9800