#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/50/2005073.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2005073
loop_
_publ_author_name
'Thomas, R. Ll.'
'Welch, A. J.'
_publ_section_title
;Haloaryl Carboranes. I.
 1,4-Bis[2-phenyl-1,2-dicarba-closo-dodecaboran(12)-1-yl]-2,3,5,6-tetrafluorobenzene
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1689
_journal_page_last               1691
_journal_paper_doi               10.1107/S0108270196000029
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C22 H30 B20 F4'
_chemical_formula_sum            'C22 H30 B20 F4'
_chemical_formula_weight         586.66
_chemical_name_systematic
;
1,4-bis(1'-closo-2'-phenyl-1',2'-dicarbadodecaboryl)-2,3,5,6-
tetrafluorobenzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 102.44(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.710(3)
_cell_length_b                   12.988(2)
_cell_length_c                   14.069(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      8
_cell_volume                     1554.2(7)
_computing_data_reduction        'CADABS (Gould & Smith, 1986)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1994)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       'ω-2θ 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  0.0133
_diffrn_reflns_av_sigmaI/netI    9.2095
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2929
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        2.1
_diffrn_standards_interval_time  480
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       needle
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.110
_refine_ls_goodness_of_fit_obs   1.221
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_restrained_S_obs      1.221
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_obs          0.0463
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0825P)²+0.1663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1361
_refine_ls_wR_factor_obs         0.1312
_reflns_number_observed          2151
_reflns_number_total             2738
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ab1305.cif
_cod_data_source_block           rlphf6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0825P)^2^+0.1663P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0825P)^2^+0.1663P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2005073
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
C11 1 .3651(2) .05379(11) .44136(11) .0329(4) Uani d . C
C12 1 .4875(2) .01308(13) .40384(11) .0390(4) Uani d . C
C13 1 .6155(2) -.03630(13) .45942(12) .0388(4) Uani d . C
F12 1 .48556(14) .01763(10) .30859(7) .0650(4) Uani d . F
F13 1 .72295(13) -.06660(10) .41038(8) .0656(4) Uani d . F
C22 1 .4664(2) .33576(11) .36287(7) .0574(5) Uani d G C
C23 1 .60400(14) .38545(12) .40831(10) .0687(6) Uani d G C
C24 1 .64017(13) .39647(12) .50895(10) .0678(6) Uani d G C
C25 1 .5387(2) .35780(12) .56414(7) .0682(6) Uani d G C
C26 1 .40107(14) .30811(11) .51870(8) .0558(5) Uani d G C
C21 1 .36490(12) .29709(9) .41807(8) .0418(4) Uani d G C
H22 1 .4381(2) .3272(2) .28431(7) .092(3) Uiso calc G H
H23 1 .6832(2) .4156(2) .36524(13) .092(3) Uiso d G H
H24 1 .7476(2) .4353(2) .54443(14) .092(3) Uiso d G H
H25 1 .5669(2) .3664(2) .64270(7) .092(3) Uiso d G H
H26 1 .3219(2) .2779(2) .56179(11) .092(3) Uiso d G H
C1 1 .2231(2) .10596(12) .37936(11) .0341(4) Uani d . C
C2 1 .2196(2) .23872(12) .36755(12) .0383(4) Uani d . C
B3 1 .1019(2) .1800(2) .43629(15) .0407(5) Uani d . B
B4 1 .0393(2) .0612(2) .37677(15) .0408(5) Uani d . B
B5 1 .1246(2) .0511(2) .27346(14) .0412(5) Uani d . B
B6 1 .2414(2) .16290(15) .27022(13) .0396(5) Uani d . B
B7 1 .0311(3) .2822(2) .3562(2) .0473(5) Uani d . B
B8 1 -.0868(2) .1708(2) .3608(2) .0500(5) Uani d . B
B9 1 -.0739(3) .0918(2) .2593(2) .0492(5) Uani d . B
B10 1 .0538(3) .1541(2) .19325(15) .0476(5) Uani d . B
B11 1 .1160(3) .2717(2) .25373(15) .0452(5) Uani d . B
B12 1 -.0788(3) .2278(2) .2469(2) .0522(6) Uani d . B
H3 1 .128(2) .1905(14) .5137(14) .055(2) Uiso d . H
H4 1 .034(2) -.0058(15) .4217(13) .055(2) Uiso d . H
H5 1 .170(2) -.0215(16) .2552(14) .055(2) Uiso d . H
H6 1 .360(2) .1644(14) .2516(13) .055(2) Uiso d . H
H7 1 .019(2) .3584(15) .3895(13) .055(2) Uiso d . H
H8 1 -0.191(2) .1744(14) .4009(14) .055(2) Uiso d . H
H9 1 -0.171(2) .0397(15) .2233(14) .055(2) Uiso d . H
H10 1 .047(2) .1445(14) .1151(14) .055(2) Uiso d . H
H11 1 .157(2) .3404(15) .2215(14) .055(2) Uiso d . H
H12 1 -0.177(2) .2702(15) .2014(13) .055(2) Uiso d . H
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'
B B 0.0013 0.0007 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 C11 C12 3_656 . 112.47(14) y
C13 C11 C1 3_656 . 124.10(14) y
C12 C11 C1 . . 123.35(14) y
F12 C12 C13 . . 115.08(14) y
F12 C12 C11 . . 121.18(14) y
C13 C12 C11 . . 123.72(14) y
F13 C13 C12 . . 114.59(14) y
F13 C13 C11 . 3_656 121.63(15) y
C12 C13 C11 . 3_656 123.78(14) y
C23 C22 C21 . . 120.0 ?
C24 C23 C22 . . 120.0 ?
C25 C24 C23 . . 120.0 ?
C26 C25 C24 . . 120.0 ?
C21 C26 C25 . . 120.0 ?
C26 C21 C22 . . 120.0 ?
C26 C21 C2 . . 120.83(10) y
C22 C21 C2 . . 119.10(10) y
C11 C1 B4 . . 120.65(13) y
C11 C1 B5 . . 120.76(13) y
B4 C1 B5 . . 62.83(12) y
C11 C1 C2 . . 119.82(13) ?
B4 C1 C2 . . 109.99(12) ?
B5 C1 C2 . . 109.69(12) ?
C11 C1 B6 . . 118.69(13) ?
B4 C1 B6 . . 113.06(13) ?
B5 C1 B6 . . 62.13(11) y
C2 C1 B6 . . 59.74(10) y
C11 C1 B3 . . 118.87(13) ?
B4 C1 B3 . . 62.42(11) y
B5 C1 B3 . . 112.99(13) ?
C2 C1 B3 . . 59.69(10) y
B6 C1 B3 . . 110.48(12) ?
C21 C2 B7 . . 124.53(14) y
C21 C2 B11 . . 122.13(13) y
B7 C2 B11 . . 61.88(12) y
C21 C2 B6 . . 115.65(13) y
B7 C2 B6 . . 112.38(14) y
B11 C2 B6 . . 61.86(11) y
C21 C2 B3 . . 119.61(13) y
B7 C2 B3 . . 61.70(11) y
B11 C2 B3 . . 112.09(14) ?
B6 C2 B3 . . 111.76(13) n
C21 C2 C1 . . 117.22(12) y
B7 C2 C1 . . 109.55(13) ?
B11 C2 C1 . . 109.45(12) ?
B6 C2 C1 . . 60.43(9) y
B3 C2 C1 . . 60.53(10) y
C2 B3 C1 . . 59.78(10) n
C2 B3 B8 . . 106.35(14) n
C1 B3 B8 . . 105.36(14) ?
C2 B3 B7 . . 58.60(11) n
C1 B3 B7 . . 106.50(14) ?
B8 B3 B7 . . 60.82(12) n
C2 B3 B4 . . 106.08(14) ?
C1 B3 B4 . . 57.46(10) n
B8 B3 B4 . . 60.42(12) n
B7 B3 B4 . . 108.74(15) ?
C1 B4 B5 . . 58.87(11) n
C1 B4 B9 . . 105.98(14) ?
B5 B4 B9 . . 60.08(12) n
C1 B4 B8 . . 106.39(14) ?
B5 B4 B8 . . 108.15(14) ?
B9 B4 B8 . . 60.06(12) n
C1 B4 B3 . . 60.12(10) n
B5 B4 B3 . . 108.00(14) ?
B9 B4 B3 . . 107.18(14) ?
B8 B4 B3 . . 59.08(11) n
C1 B5 B10 . . 106.29(13) ?
C1 B5 B4 . . 58.30(10) n
B10 B5 B4 . . 108.40(15) ?
C1 B5 B9 . . 105.51(14) ?
B10 B5 B9 . . 60.51(12) n
B4 B5 B9 . . 60.04(12) n
C1 B5 B6 . . 59.91(10) n
B10 B5 B6 . . 59.34(11) n
B4 B5 B6 . . 107.64(14) ?
B9 B5 B6 . . 107.57(15) ?
C2 B6 C1 . . 59.84(10) n
C2 B6 B10 . . 106.14(15) ?
C1 B6 B10 . . 105.41(14) ?
C2 B6 B11 . . 58.63(11) n
C1 B6 B11 . . 106.45(14) ?
B10 B6 B11 . . 60.38(12) n
C2 B6 B5 . . 106.45(14) ?
C1 B6 B5 . . 57.97(10) n
B10 B6 B5 . . 60.15(11) n
B11 B6 B5 . . 108.32(15) ?
C2 B7 B11 . . 59.16(11) n
C2 B7 B3 . . 59.70(11) n
B11 B7 B3 . . 108.28(14) ?
C2 B7 B12 . . 106.1(2) ?
B11 B7 B12 . . 60.20(13) n
B3 B7 B12 . . 107.65(15) ?
C2 B7 B8 . . 106.10(14) ?
B11 B7 B8 . . 108.3(2) ?
B3 B7 B8 . . 59.41(12) n
B12 B7 B8 . . 60.07(13) n
B3 B8 B12 . . 107.6(2) ?
B3 B8 B9 . . 108.11(15) ?
B12 B8 B9 . . 59.77(13) y
B3 B8 B4 . . 60.50(11) n
B12 B8 B4 . . 107.6(2) ?
B9 B8 B4 . . 59.82(12) n
B3 B8 B7 . . 59.77(11) n
B12 B8 B7 . . 59.68(13) n
B9 B8 B7 . . 107.6(2) ?
B4 B8 B7 . . 107.97(15) ?
B12 B9 B4 . . 108.1(2) ?
B12 B9 B5 . . 108.0(2) ?
B4 B9 B5 . . 59.87(11) n
B12 B9 B8 . . 60.08(13) n
B4 B9 B8 . . 60.12(12) n
B5 B9 B8 . . 108.03(15) ?
B12 B9 B10 . . 60.19(13) n
B4 B9 B10 . . 107.56(14) ?
B5 B9 B10 . . 59.63(11) y
B8 B9 B10 . . 108.0(2) ?
B6 B10 B5 . . 60.51(11) n
B6 B10 B11 . . 60.13(11) n
B5 B10 B11 . . 108.41(14) ?
B6 B10 B12 . . 107.73(15) ?
B5 B10 B12 . . 107.6(2) ?
B11 B10 B12 . . 59.68(13) n
B6 B10 B9 . . 107.97(14) ?
B5 B10 B9 . . 59.86(12) n
B11 B10 B9 . . 107.4(2) ?
B12 B10 B9 . . 59.50(13) n
C2 B11 B7 . . 58.96(11) n
C2 B11 B6 . . 59.51(10) n
B7 B11 B6 . . 108.12(14) ?
C2 B11 B12 . . 105.99(15) ?
B7 B11 B12 . . 60.24(13) n
B6 B11 B12 . . 107.88(15) ?
C2 B11 B10 . . 106.14(13) ?
B7 B11 B10 . . 108.7(2) ?
B6 B11 B10 . . 59.50(12) n
B12 B11 B10 . . 60.51(13) n
B11 B12 B7 . . 59.56(12) n
B11 B12 B9 . . 108.20(15) ?
B7 B12 B9 . . 108.31(15) ?
B11 B12 B8 . . 107.91(15) ?
B7 B12 B8 . . 60.25(13) n
B9 B12 B8 . . 60.15(13) n
B11 B12 B10 . . 59.81(12) y
B7 B12 B10 . . 107.59(15) ?
B9 B12 B10 . . 60.31(13) n
B8 B12 B10 . . 108.17(15) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C11 C13 3_656 1.388(2) y
C11 C12 . 1.392(2) y
C11 C1 . 1.511(2) y
C12 F12 . 1.338(2) y
C12 C13 . 1.375(2) y
C13 F13 . 1.336(2) y
C13 C11 3_656 1.388(2) y
C22 C23 . 1.39 n
C22 C21 . 1.39 n
C23 C24 . 1.39 n
C24 C25 . 1.39 n
C25 C26 . 1.39 n
C26 C21 . 1.39 n
C21 C2 . 1.515(2) y
C1 B4 . 1.697(3) y
C1 B5 . 1.707(2) y
C1 C2 . 1.732(2) y
C1 B6 . 1.742(2) y
C1 B3 . 1.745(2) y
C2 B7 . 1.711(3) y
C2 B11 . 1.714(2) y
C2 B6 . 1.730(3) y
C2 B3 . 1.730(3) y
B3 B8 . 1.758(3) y
B3 B7 . 1.765(3) y
B3 B4 . 1.784(3) y
B4 B5 . 1.774(3) y
B4 B9 . 1.777(3) y
B4 B8 . 1.782(3) y
B5 B10 . 1.774(3) y
B5 B9 . 1.778(3) y
B5 B6 . 1.780(3) y
B6 B10 . 1.759(3) y
B6 B11 . 1.770(3) y
B7 B11 . 1.761(3) y
B7 B12 . 1.773(3) y
B7 B8 . 1.783(3) y
B8 B12 . 1.780(3) y
B8 B9 . 1.782(3) y
B9 B12 . 1.775(3) y
B9 B10 . 1.789(3) y
B10 B11 . 1.775(3) y
B10 B12 . 1.787(3) y
B11 B12 . 1.772(3) y
