#------------------------------------------------------------------------------
#$Date: 2016-02-18 13:25:00 +0100 (jue 18 de feb de 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/00/00/8000056.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
loop_
_publ_author_name
'Yosuke Uchiyama'
'Gaku Yamamoto'
_publ_section_title
;
 A Bromine Adduct of 2,3,6,7,14,15-Hexamethyl-9,10-distibatriptycene.
 The First Stibonium--Stiborate Zwitterion
;
_journal_issue                   7
_journal_name_full               'Chemistry Letters'
_journal_page_first              966
_journal_paper_doi               10.1246/cl.2005.966
_journal_volume                  34
_journal_year                    2005
_chemical_formula_moiety         'C24 H24 Sb2, C3 F3'
_chemical_formula_sum            'C27 H24 F3 Sb2'
_chemical_formula_weight         648.96
_chemical_melting_point          288(3)
_chemical_name_common            9,10-distibatriptycene
_chemical_name_systematic
; 
2,3,6,7,14,15-Hexamethyl-9,10-distibatriptycene
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0000(4)
_cell_angle_beta                 116.9319(5)
_cell_angle_gamma                90.0000(4)
_cell_formula_units_Z            8
_cell_length_a                   26.4096(10)
_cell_length_b                   10.1131(2)
_cell_length_c                   20.5028(9)
_cell_measurement_temperature    113(2)
_cell_volume                     4882.1(3)
_computing_cell_refinement       Crystalclear
_computing_data_collection       Crystalclear
_computing_data_reduction        YadokariXG
_computing_molecular_graphics    'ORTEP-III ver.1.0.3'
_computing_publication_material  YadokariXG
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16932
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    2.248
_exptl_absorpt_correction_T_max  0.6620
_exptl_absorpt_correction_T_min  0.6620
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2520
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0258
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0394P)²+2.8269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0660
_reflns_number_gt                4987
_reflns_number_total             5283
_reflns_threshold_expression     >2sigma(I)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '285-290' was changed to '288(3)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               8000056
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_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 0.325468(7) -0.227256(16) 0.092838(9) 0.01152(6) Uani 1 1 d .
Sb2 Sb 0.411969(7) 0.032471(15) 0.221700(8) 0.01130(6) Uani 1 1 d .
C3 C 0.46990(11) -0.2118(2) 0.31595(14) 0.0131(5) Uani 1 1 d .
H1 H 0.4919 -0.1454 0.3496 0.016 Uiso 1 1 calc R
C4 C 0.28608(14) 0.2389(3) -0.0314(2) 0.0330(7) Uani 1 1 d .
C5 C 0.46179(13) -0.5873(3) 0.30444(17) 0.0248(6) Uani 1 1 d .
H2 H 0.5008 -0.6073 0.3137 0.037 Uiso 1 1 calc R
H3 H 0.4352 -0.6411 0.2634 0.037 Uiso 1 1 calc R
H4 H 0.4572 -0.6075 0.3483 0.037 Uiso 1 1 calc R
C6 C 0.39811(14) -0.0142(3) -0.10091(16) 0.0272(7) Uani 1 1 d .
H5 H 0.3781 0.0633 -0.1299 0.041 Uiso 1 1 calc R
H6 H 0.3773 -0.0946 -0.1249 0.041 Uiso 1 1 calc R
H7 H 0.4365 -0.0178 -0.0969 0.041 Uiso 1 1 calc R
F1 F 0.27892(10) 0.4040(2) 0.12033(12) 0.0514(6) Uani 1 1 d .
C8 C 0.40599(11) -0.4046(3) 0.21798(14) 0.0160(5) Uani 1 1 d .
H8 H 0.3839 -0.4709 0.1843 0.019 Uiso 1 1 calc R
C9 C 0.42652(10) -0.1744(2) 0.24804(14) 0.0121(5) Uani 1 1 d .
C10 C 0.44962(11) -0.4424(2) 0.28578(15) 0.0158(5) Uani 1 1 d .
C11 C 0.43625(11) 0.1008(2) 0.09226(14) 0.0138(5) Uani 1 1 d .
H9 H 0.4588 0.1672 0.1256 0.017 Uiso 1 1 calc R
C12 C 0.37313(10) -0.0851(2) 0.06509(13) 0.0131(5) Uani 1 1 d .
C13 C 0.28905(11) -0.0800(2) 0.13469(14) 0.0139(5) Uani 1 1 d .
F3 F 0.32132(9) 0.2282(2) -0.06178(13) 0.0454(5) Uani 1 1 d .
F2 F 0.35048(8) 0.3816(2) 0.05854(13) 0.0515(6) Uani 1 1 d .
C16 C 0.14221(14) -0.0185(4) 0.1218(2) 0.0421(9) Uani 1 1 d .
H10 H 0.1269 -0.0925 0.0875 0.063 Uiso 1 1 calc R
H11 H 0.1221 0.0629 0.0983 0.063 Uiso 1 1 calc R
H12 H 0.1372 -0.0361 0.1655 0.063 Uiso 1 1 calc R
C17 C 0.40178(12) -0.0039(3) -0.02559(14) 0.0181(5) Uani 1 1 d .
C18 C 0.20485(12) -0.0026(3) 0.14350(17) 0.0244(6) Uani 1 1 d .
C20 C 0.23079(11) -0.0867(3) 0.11400(15) 0.0178(5) Uani 1 1 d .
H13 H 0.2083 -0.1505 0.0788 0.021 Uiso 1 1 calc R
C21 C 0.46680(13) 0.1937(3) 0.00136(16) 0.0255(6) Uani 1 1 d .
H14 H 0.4941 0.1471 -0.0105 0.038 Uiso 1 1 calc R
H15 H 0.4871 0.2553 0.0418 0.038 Uiso 1 1 calc R
H16 H 0.4400 0.2430 -0.0416 0.038 Uiso 1 1 calc R
C22 C 0.40603(10) 0.0131(2) 0.11406(13) 0.0125(5) Uani 1 1 d .
C23 C 0.29496(11) 0.1046(3) 0.21150(14) 0.0182(5) Uani 1 1 d .
H17 H 0.3168 0.1728 0.2439 0.022 Uiso 1 1 calc R
C24 C 0.37184(11) -0.0914(3) -0.00356(14) 0.0159(5) Uani 1 1 d .
H18 H 0.3496 -0.1582 -0.0367 0.019 Uiso 1 1 calc R
C25 C 0.39418(11) -0.2722(2) 0.19865(14) 0.0129(5) Uani 1 1 d .
C26 C 0.23726(12) 0.0951(3) 0.19290(16) 0.0240(6) Uani 1 1 d .
C27 C 0.32160(11) 0.0171(2) 0.18404(14) 0.0141(5) Uani 1 1 d .
C29 C 0.43467(11) 0.0947(3) 0.02355(15) 0.0177(5) Uani 1 1 d .
C30 C 0.48161(10) -0.3450(3) 0.33546(14) 0.0147(5) Uani 1 1 d .
C31 C 0.52926(11) -0.3824(3) 0.40965(15) 0.0190(5) Uani 1 1 d .
H19 H 0.5134 -0.4285 0.4383 0.029 Uiso 1 1 calc R
H20 H 0.5490 -0.3023 0.4356 0.029 Uiso 1 1 calc R
H21 H 0.5562 -0.4407 0.4029 0.029 Uiso 1 1 calc R
C32 C 0.26477(14) 0.3285(3) 0.06099(19) 0.0340(8) Uani 1 1 d .
C33 C 0.21194(15) 0.1878(4) 0.2281(2) 0.0418(9) Uani 1 1 d .
H22 H 0.1766 0.2254 0.1904 0.063 Uiso 1 1 calc R
H23 H 0.2389 0.2592 0.2531 0.063 Uiso 1 1 calc R
H24 H 0.2039 0.1389 0.2637 0.063 Uiso 1 1 calc R
C35 C 0.30107(13) 0.3174(3) 0.0304(2) 0.0341(8) Uani 1 1 d .
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'
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
_geom_angle_site_symmetry_3
C12 Sb1 C13 93.67(10) . .
C12 Sb1 C25 94.61(9) . .
C13 Sb1 C25 93.97(9) . .
C22 Sb2 C9 95.21(9) . .
C22 Sb2 C27 94.10(9) . .
C9 Sb2 C27 93.58(9) . .
C9 C3 C30 121.4(2) . .
C9 C3 H1 119.3 . .
C30 C3 H1 119.3 . .
F3 C4 C32 119.9(3) . 7
F3 C4 C35 119.9(3) . .
C32 C4 C35 120.2(3) 7 .
C10 C5 H2 109.5 . .
C10 C5 H3 109.5 . .
H2 C5 H3 109.5 . .
C10 C5 H4 109.5 . .
H2 C5 H4 109.5 . .
H3 C5 H4 109.5 . .
C17 C6 H5 109.5 . .
C17 C6 H6 109.5 . .
H5 C6 H6 109.5 . .
C17 C6 H7 109.5 . .
H5 C6 H7 109.5 . .
H6 C6 H7 109.5 . .
C25 C8 C10 121.6(2) . .
C25 C8 H8 119.2 . .
C10 C8 H8 119.2 . .
C3 C9 C25 119.2(2) . .
C3 C9 Sb2 119.12(18) . .
C25 C9 Sb2 121.72(18) . .
C30 C10 C8 119.2(2) . .
C30 C10 C5 120.7(2) . .
C8 C10 C5 120.1(2) . .
C29 C11 C22 122.5(2) . .
C29 C11 H9 118.8 . .
C22 C11 H9 118.8 . .
C24 C12 C22 118.7(2) . .
C24 C12 Sb1 119.18(18) . .
C22 C12 Sb1 122.15(18) . .
C27 C13 C20 119.1(2) . .
C27 C13 Sb1 122.53(18) . .
C20 C13 Sb1 118.32(19) . .
C18 C16 H10 109.5 . .
C18 C16 H11 109.5 . .
H10 C16 H11 109.5 . .
C18 C16 H12 109.5 . .
H10 C16 H12 109.5 . .
H11 C16 H12 109.5 . .
C24 C17 C29 118.5(2) . .
C24 C17 C6 120.5(2) . .
C29 C17 C6 121.1(3) . .
C20 C18 C26 119.2(3) . .
C20 C18 C16 119.7(3) . .
C26 C18 C16 121.2(3) . .
C18 C20 C13 122.0(3) . .
C18 C20 H13 119.0 . .
C13 C20 H13 119.0 . .
C29 C21 H14 109.5 . .
C29 C21 H15 109.5 . .
H14 C21 H15 109.5 . .
C29 C21 H16 109.5 . .
H14 C21 H16 109.5 . .
H15 C21 H16 109.5 . .
C11 C22 C12 118.7(2) . .
C11 C22 Sb2 118.99(18) . .
C12 C22 Sb2 122.28(18) . .
C26 C23 C27 122.2(3) . .
C26 C23 H17 118.9 . .
C27 C23 H17 118.9 . .
C17 C24 C12 122.8(2) . .
C17 C24 H18 118.6 . .
C12 C24 H18 118.6 . .
C8 C25 C9 119.4(2) . .
C8 C25 Sb1 117.91(18) . .
C9 C25 Sb1 122.71(18) . .
C18 C26 C23 118.8(2) . .
C18 C26 C33 121.8(3) . .
C23 C26 C33 119.4(3) . .
C13 C27 C23 118.8(2) . .
C13 C27 Sb2 122.01(18) . .
C23 C27 Sb2 119.18(19) . .
C11 C29 C17 118.9(2) . .
C11 C29 C21 120.8(2) . .
C17 C29 C21 120.3(2) . .
C10 C30 C3 119.3(2) . .
C10 C30 C31 120.6(2) . .
C3 C30 C31 120.1(2) . .
C30 C31 H19 109.5 . .
C30 C31 H20 109.5 . .
H19 C31 H20 109.5 . .
C30 C31 H21 109.5 . .
H19 C31 H21 109.5 . .
H20 C31 H21 109.5 . .
F1 C32 C35 119.9(3) . .
F1 C32 C4 119.9(3) . 7
C35 C32 C4 120.2(3) . 7
C26 C33 H22 109.5 . .
C26 C33 H23 109.5 . .
H22 C33 H23 109.5 . .
C26 C33 H24 109.5 . .
H22 C33 H24 109.5 . .
H23 C33 H24 109.5 . .
F2 C35 C32 120.9(3) . .
F2 C35 C4 119.5(3) . .
C32 C35 C4 119.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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) 7
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) 7
C33 H22 0.9800 .
C33 H23 0.9800 .
C33 H24 0.9800 .
