#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/28/2212876.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_2212876
loop_
_publ_author_name
'Csöregh, Ingeborg'
'Toda, Fumio'
_publ_section_title
;
 1,1,1,3,3,3-Hexafluoro-2,2-bis(4-hydroxyphenyl)propane--benzene (2/3)
;
_journal_coeditor_code           GK2056
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1769
_journal_page_last               o1771
_journal_paper_doi               10.1107/S1600536807010677
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '2C15 H10 F6 O2 , 3C6 H6'
_chemical_formula_moiety         '2C15 H10 F6 O2 , 3C6 H6'
_chemical_formula_sum            'C48 H38 F12 O4'
_chemical_formula_weight         906.78
_chemical_name_systematic
;
1,1,1,3,3,3-Hexafluoro-2,2-bis(4-hydroxyphenyl)propane--benzene (2/3)
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 99.57(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.173(3)
_cell_length_b                   9.0580(10)
_cell_length_c                   24.218(4)
_cell_measurement_reflns_used    5000
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.80
_cell_measurement_theta_min      2.47
_cell_volume                     4363.7(11)
_computing_cell_refinement       'IPDS Software'
_computing_data_collection       'IPDS Software (Stoe & Cie, 1997)'
_computing_data_reduction        'IPDS Software'
_computing_molecular_graphics    'SHELXTL/XP (Sheldrick, 1990)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       φ
_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  0.0587
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14471
_diffrn_reflns_theta_full        25.90
_diffrn_reflns_theta_max         25.90
_diffrn_reflns_theta_min         2.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1864
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0398
_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)+(0.0385P)²+0.995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                2914
_reflns_number_total             4183
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2056.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2212876
_cod_database_fobs_code          2212876
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.28846(8) 0.57068(17) 0.35264(6) 0.0329(4) Uani d . 1
C C2 0.32657(9) 0.71803(19) 0.36147(8) 0.0428(4) Uani d . 1
F F21 0.35647(5) 0.73365(12) 0.41487(4) 0.0516(3) Uani d . 1
F F22 0.28539(6) 0.83428(11) 0.35008(5) 0.0578(3) Uani d . 1
F F23 0.37459(6) 0.73302(12) 0.32970(5) 0.0577(3) Uani d . 1
C C3 0.26583(9) 0.5486(2) 0.28882(7) 0.0409(4) Uani d . 1
F F31 0.22027(5) 0.44141(11) 0.27824(4) 0.0469(3) Uani d . 1
F F32 0.23868(6) 0.66947(12) 0.26233(4) 0.0536(3) Uani d . 1
F F33 0.31760(6) 0.51055(14) 0.26372(4) 0.0587(3) Uani d . 1
C C11 0.33243(8) 0.43694(17) 0.37374(6) 0.0306(3) Uani d . 1
C C12 0.40217(8) 0.44088(18) 0.38783(6) 0.0346(4) Uani d . 1
H H12 0.4255 0.5305 0.3841 0.041(5) Uiso calc R 1
C C13 0.43807(8) 0.31554(19) 0.40729(6) 0.0366(4) Uani d . 1
H H13 0.4856 0.3204 0.4177 0.043(5) Uiso calc R 1
C C14 0.40496(8) 0.18362(18) 0.41165(6) 0.0336(4) Uani d . 1
O O14 0.43832(6) 0.05582(13) 0.43058(5) 0.0427(3) Uani d . 1
H H14O 0.4870 0.0811 0.4415 0.079(7) Uiso d R 1
C C15 0.33584(8) 0.17674(18) 0.39640(7) 0.0360(4) Uani d . 1
H H15 0.3130 0.0857 0.3985 0.049(5) Uiso calc R 1
C C16 0.30025(8) 0.30237(17) 0.37816(6) 0.0345(4) Uani d . 1
H H16 0.2527 0.2971 0.3684 0.036(4) Uiso calc R 1
C C21 0.22800(8) 0.58251(17) 0.38415(6) 0.0308(3) Uani d . 1
C C22 0.23829(8) 0.5521(2) 0.44109(6) 0.0398(4) Uani d . 1
H H22 0.2820 0.5257 0.4594 0.043(5) Uiso calc R 1
C C23 0.18641(8) 0.5595(2) 0.47174(6) 0.0416(4) Uani d . 1
H H23 0.1946 0.5390 0.5108 0.046(5) Uiso calc R 1
C C24 0.12267(8) 0.59670(19) 0.44526(6) 0.0363(4) Uani d . 1
O O24 0.06880(6) 0.60280(15) 0.47392(5) 0.0473(3) Uani d . 1
H H24O 0.0851 0.5623 0.5091 0.088(8) Uiso d R 1
C C25 0.11167(8) 0.6302(2) 0.38895(7) 0.0392(4) Uani d . 1
H H25 0.0680 0.6574 0.3708 0.053(5) Uiso calc R 1
C C26 0.16415(8) 0.62422(18) 0.35900(6) 0.0364(4) Uani d . 1
H H26 0.1562 0.6492 0.3204 0.040(5) Uiso calc R 1
C C1B1 0.09588(13) 0.0688(3) 0.45284(9) 0.0741(7) Uani d . 1
H H1B1 0.0955 0.0293 0.4891 0.098(9) Uiso calc R 1
C C2B1 0.05507(13) 0.1858(3) 0.43426(11) 0.0806(8) Uani d . 1
H H2B1 0.0262 0.2265 0.4575 0.118(11) Uiso calc R 1
C C3B1 0.05590(14) 0.2436(3) 0.38276(13) 0.0823(8) Uani d . 1
H H3B1 0.0278 0.3249 0.3698 0.099(9) Uiso calc R 1
C C4B1 0.09799(16) 0.1831(4) 0.34942(12) 0.0906(8) Uani d . 1
H H4B1 0.0990 0.2232 0.3133 0.140(13) Uiso calc R 1
C C5B1 0.13832(13) 0.0658(3) 0.36785(10) 0.0760(7) Uani d . 1
H H5B1 0.1671 0.0247 0.3446 0.102(9) Uiso calc R 1
C C6B1 0.13721(11) 0.0085(3) 0.41927(8) 0.0610(6) Uani d . 1
H H6B1 0.1650 -0.0734 0.4321 0.074(7) Uiso calc R 1
C C1B2 0.0287 0.5101 0.2375 0.109(6) Uani d P 0.50
H H1B2 0.0483 0.4193 0.2291 0.23(5) Uiso d PR 0.50
C C2B2 0.0572 0.6430 0.2251 0.075(3) Uani d PR 0.50
H H2B2 0.0963 0.6431 0.2080 0.15(3) Uiso d PR 0.50
C C3B2 0.0286 0.7759 0.2376 0.070(3) Uani d PR 0.50
H H3B2 0.0482 0.8667 0.2291 0.12(2) Uiso d PR 0.50
C C1B3 0.0000 0.4808(4) 0.2500 0.081(6) Uani d SP 0.50
H H1B3 0.0000 0.3760 0.2500 0.15(4) Uiso d SPR 0.50
C C2B3 0.0499 0.5576(4) 0.2288 0.070(3) Uani d PR 0.50
H H2B3 0.0841 0.5051 0.2144 0.092(18) Uiso d PR 0.50
C C3B3 0.0499 0.7110(4) 0.2288 0.0485(17) Uani d PR 0.50
H H3B3 0.0841 0.7635 0.2144 0.087(17) Uiso d PR 0.50
C C4B3 0.0000 0.7878(4) 0.2500 0.052(2) Uani d SPR 0.50
H H4B3 0.0000 0.8926 0.2500 0.10(3) Uiso d SPR 0.50
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C11 . . 112.96(14)
C2 C1 C21 . . 106.76(13)
C11 C1 C21 . . 110.44(12)
C2 C1 C3 . . 107.97(13)
C11 C1 C3 . . 106.72(12)
C21 C1 C3 . . 112.05(13)
F21 C2 F22 . . 106.23(14)
F21 C2 F23 . . 106.91(15)
F22 C2 F23 . . 106.52(14)
F21 C2 C1 . . 111.12(13)
F22 C2 C1 . . 112.00(15)
F23 C2 C1 . . 113.61(14)
F31 C3 F32 . . 106.83(14)
F31 C3 F33 . . 106.91(14)
F32 C3 F33 . . 106.31(13)
F31 C3 C1 . . 111.43(13)
F32 C3 C1 . . 113.65(14)
F33 C3 C1 . . 111.32(14)
C12 C11 C16 . . 117.93(15)
C12 C11 C1 . . 124.40(14)
C16 C11 C1 . . 117.66(14)
C13 C12 C11 . . 120.79(15)
C13 C12 H12 . . 119.6
C11 C12 H12 . . 119.6
C14 C13 C12 . . 120.16(15)
C14 C13 H13 . . 119.9
C12 C13 H13 . . 119.9
C13 C14 O14 . . 122.43(14)
C13 C14 C15 . . 119.82(15)
O14 C14 C15 . . 117.75(15)
C14 O14 H14O . . 107.4
C16 C15 C14 . . 119.78(16)
C16 C15 H15 . . 120.1
C14 C15 H15 . . 120.1
C15 C16 C11 . . 121.48(15)
C15 C16 H16 . . 119.3
C11 C16 H16 . . 119.3
C26 C21 C22 . . 117.80(14)
C26 C21 C1 . . 123.71(13)
C22 C21 C1 . . 118.48(14)
C23 C22 C21 . . 121.52(15)
C23 C22 H22 . . 119.2
C21 C22 H22 . . 119.2
C24 C23 C22 . . 119.51(14)
C24 C23 H23 . . 120.2
C22 C23 H23 . . 120.2
C23 C24 C25 . . 119.86(15)
C23 C24 O24 . . 121.68(14)
C25 C24 O24 . . 118.45(14)
C24 O24 H24O . . 104.7
C24 C25 C26 . . 119.98(15)
C24 C25 H25 . . 120.0
C26 C25 H25 . . 120.0
C21 C26 C25 . . 121.27(14)
C21 C26 H26 . . 119.4
C25 C26 H26 . . 119.4
C2B1 C1B1 C6B1 . . 120.3(2)
C2B1 C1B1 H1B1 . . 119.9
C6B1 C1B1 H1B1 . . 119.9
C1B1 C2B1 C3B1 . . 120.1(2)
C1B1 C2B1 H2B1 . . 119.9
C3B1 C2B1 H2B1 . . 119.9
C2B1 C3B1 C4B1 . . 119.2(3)
C2B1 C3B1 H3B1 . . 120.4
C4B1 C3B1 H3B1 . . 120.4
C5B1 C4B1 C3B1 . . 120.6(2)
C5B1 C4B1 H4B1 . . 119.7
C3B1 C4B1 H4B1 . . 119.7
C6B1 C5B1 C4B1 . . 119.9(2)
C6B1 C5B1 H5B1 . . 120.0
C4B1 C5B1 H5B1 . . 120.0
C5B1 C6B1 C1B1 . . 119.8(2)
C5B1 C6B1 H6B1 . . 120.1
C1B1 C6B1 H6B1 . . 120.1
C2B2 C1B2 C1B2 . 2 119.9
C2B2 C1B2 H1B2 . . 120.0
C1B2 C1B2 H1B2 2 . 120.0
C1B2 C2B2 C3B2 . . 120.0
C1B2 C2B2 H2B2 . . 120.0
C3B2 C2B2 H2B2 . . 120.0
C3B2 C3B2 C2B2 2 . 120.0
C3B2 C3B2 H3B2 2 . 120.0
C2B2 C3B2 H3B2 . . 120.0
C2B3 C1B3 C2B3 . 2 120.0
C2B3 C1B3 H1B3 . . 120.0
C2B3 C1B3 H1B3 2 . 120.0
C1B3 C2B3 C3B3 . . 120.0
C1B3 C2B3 H2B3 . . 120.0
C3B3 C2B3 H2B3 . . 120.0
C4B3 C3B3 H3B3 . . 120.0
C2B3 C3B3 H3B3 . . 120.0
C3B3 C4B3 H4B3 . . 120.0
C3B3 C4B3 H4B3 2 . 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.537(2)
C1 C11 . 1.538(2)
C1 C21 . 1.546(2)
C1 C3 . 1.550(2)
C2 F21 . 1.340(2)
C2 F22 . 1.341(2)
C2 F23 . 1.340(2)
C3 F31 . 1.332(2)
C3 F32 . 1.339(2)
C3 F33 . 1.338(2)
C11 C12 . 1.392(2)
C11 C16 . 1.394(2)
C12 C13 . 1.386(2)
C12 H12 . 0.9500
C13 C14 . 1.382(2)
C13 H13 . 0.9500
C14 O14 . 1.3786(19)
C14 C15 . 1.383(2)
O14 H14O . 1.0004
C15 C16 . 1.379(2)
C15 H15 . 0.9500
C16 H16 . 0.9500
C21 C26 . 1.383(2)
C21 C22 . 1.388(2)
C22 C23 . 1.382(2)
C22 H22 . 0.9500
C23 C24 . 1.380(2)
C23 H23 . 0.9500
C24 C25 . 1.379(2)
C24 O24 . 1.3844(19)
O24 H24O . 0.9352
C25 C26 . 1.380(2)
C25 H25 . 0.9500
C26 H26 . 0.9500
C1B1 C2B1 . 1.372(4)
C1B1 C6B1 . 1.371(3)
C1B1 H1B1 . 0.9500
C2B1 C3B1 . 1.355(4)
C2B1 H2B1 . 0.9500
C3B1 C4B1 . 1.379(4)
C3B1 H3B1 . 0.9500
C4B1 C5B1 . 1.367(4)
C4B1 H4B1 . 0.9500
C5B1 C6B1 . 1.353(3)
C5B1 H5B1 . 0.9500
C6B1 H6B1 . 0.9500
C1B2 C2B2 . 1.3900
C1B2 C1B2 2 1.3903(3)
C1B2 H1B2 . 0.9500
C2B2 C3B2 . 1.3900
C2B2 H2B2 . 0.9500
C3B2 C3B2 2 1.3860
C3B2 H3B2 . 0.9500
C1B3 C2B3 . 1.3898
C1B3 C2B3 2 1.3898
C1B3 H1B3 . 0.9500
C2B3 C3B3 . 1.3900
C2B3 H2B3 . 0.9500
C3B3 C4B3 . 1.3898
C3B3 H3B3 . 0.9500
C4B3 C3B3 2 1.3898
C4B3 H4B3 . 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O14 H14O O24 3_545 1.00 1.72 2.700(2) 167 yes
O24 H24O O14 7_556 0.94 1.93 2.747(2) 144 yes
C15 H15 F22 1_545 0.95 2.58 3.397(2) 144 yes
C5B1 H5B1 F33 4_545 0.95 2.69 3.484(3) 141 yes
C1B2 H1B2 F23 4_545 0.95 2.83 3.717 155 yes
C2B3 H2B3 F23 4_545 0.95 2.86 3.700 147 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C11 C1 C2 F21 . . -52.72(17)
C21 C1 C2 F21 . . 68.87(17)
C3 C1 C2 F21 . . -170.48(13)
C11 C1 C2 F22 . . -171.36(13)
C21 C1 C2 F22 . . -49.77(17)
C3 C1 C2 F22 . . 70.88(17)
C11 C1 C2 F23 . . 67.89(18)
C21 C1 C2 F23 . . -170.53(13)
C3 C1 C2 F23 . . -49.88(19)
C2 C1 C3 F31 . . -166.17(13)
C11 C1 C3 F31 . . 72.12(16)
C21 C1 C3 F31 . . -48.89(18)
C2 C1 C3 F32 . . -45.41(19)
C11 C1 C3 F32 . . -167.12(14)
C21 C1 C3 F32 . . 71.87(18)
C2 C1 C3 F33 . . 74.59(17)
C11 C1 C3 F33 . . -47.12(18)
C21 C1 C3 F33 . . -168.13(14)
C2 C1 C11 C12 . . -13.6(2)
C21 C1 C11 C12 . . -133.07(15)
C3 C1 C11 C12 . . 104.91(17)
C2 C1 C11 C16 . . 167.50(13)
C21 C1 C11 C16 . . 48.02(18)
C3 C1 C11 C16 . . -74.00(17)
C16 C11 C12 C13 . . -2.0(2)
C1 C11 C12 C13 . . 179.12(14)
C11 C12 C13 C14 . . 1.6(2)
C12 C13 C14 O14 . . 179.80(14)
C12 C13 C14 C15 . . 0.2(2)
C13 C14 C15 C16 . . -1.5(2)
O14 C14 C15 C16 . . 178.86(14)
C14 C15 C16 C11 . . 1.1(2)
C12 C11 C16 C15 . . 0.6(2)
C1 C11 C16 C15 . . 179.62(14)
C2 C1 C21 C26 . . 95.17(18)
C11 C1 C21 C26 . . -141.66(15)
C3 C1 C21 C26 . . -22.8(2)
C2 C1 C21 C22 . . -83.70(18)
C11 C1 C21 C22 . . 39.5(2)
C3 C1 C21 C22 . . 158.29(15)
C26 C21 C22 C23 . . 1.6(3)
C1 C21 C22 C23 . . -179.50(16)
C21 C22 C23 C24 . . 0.5(3)
C22 C23 C24 C25 . . -1.8(3)
C22 C23 C24 O24 . . 178.76(17)
C23 C24 C25 C26 . . 1.0(3)
O24 C24 C25 C26 . . -179.55(16)
C22 C21 C26 C25 . . -2.4(3)
C1 C21 C26 C25 . . 178.74(16)
C24 C25 C26 C21 . . 1.1(3)
C6B1 C1B1 C2B1 C3B1 . . -0.7(4)
C1B1 C2B1 C3B1 C4B1 . . 0.2(4)
C2B1 C3B1 C4B1 C5B1 . . 0.2(4)
C3B1 C4B1 C5B1 C6B1 . . -0.1(4)
C4B1 C5B1 C6B1 C1B1 . . -0.4(4)
C2B1 C1B1 C6B1 C5B1 . . 0.8(4)
C1B2 C1B2 C2B2 C3B2 2 . 0.1
C1B2 C2B2 C3B2 C3B2 . 2 -0.1
C2B3 C1B3 C2B3 C3B3 2 . 0.0
C1B3 C2B3 C3B3 C4B3 . . 0.0
C2B3 C3B3 C4B3 C3B3 . 2 0.0
