#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/26/7202685.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_7202685
loop_
_publ_author_name
'Gdaniec, Maria'
_publ_section_title
;
 On the polymorphs of pentafluorophenol and its 2?:?1 co-crystal with
 pentafluoroaniline
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              286
_journal_paper_doi               10.1039/b700245a
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C6 H F5 O'
_chemical_formula_sum            'C6 H F5 O'
_chemical_formula_weight         184.07
_chemical_name_systematic
;
2,3,4,5,6-pentafluorophenol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   5.1398(9)
_cell_length_b                   19.0901(16)
_cell_length_c                   19.1520(15)
_cell_measurement_reflns_used    3588
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      4
_cell_volume                     1879.2(4)
_computing_cell_refinement
;
Oxford Diffraction, CrysAlis Software, Version 1.172, 2004
;
_computing_data_collection
;
Oxford Diffraction, CrysAlis Software, Version 1.172, 2004
;
_computing_data_reduction
;
Oxford Diffraction, CrysAlis Software, Version 1.172, 2004
;
_computing_molecular_graphics
; 'Stereochemical Workstation (Siemens
Analytical X-Ray Instruments, Inc., 1989)'
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω scans'
_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  0.0746
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9704
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         4.11
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.952
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         1946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0490
_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)+(0.0514P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                1547
_reflns_number_total             1946
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b700245a.txt
_cod_data_source_block           H1
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_database_code               7202685
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'
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
O1A O 0.6676(7) 0.30583(17) 0.18317(17) 0.0306(8) Uani 1 1 d . . .
H1A H 0.5740 0.3377 0.2131 0.037 Uiso 1 1 d R . .
F2A F 0.2861(6) 0.40206(16) 0.14725(15) 0.0385(8) Uani 1 1 d . . .
F3A F 0.2705(6) 0.45782(17) 0.01658(17) 0.0478(9) Uani 1 1 d . . .
F4A F 0.6280(7) 0.41707(17) -0.08131(14) 0.0509(10) Uani 1 1 d . . .
F5A F 0.9984(6) 0.32159(16) -0.04664(16) 0.0470(9) Uani 1 1 d . . .
F6A F 1.0158(6) 0.26748(15) 0.08399(15) 0.0389(8) Uani 1 1 d . . .
C1A C 0.6520(9) 0.3353(2) 0.1176(2) 0.0266(12) Uani 1 1 d . . .
C2A C 0.4640(10) 0.3822(3) 0.0995(3) 0.0289(12) Uani 1 1 d . . .
C3A C 0.4548(10) 0.4110(3) 0.0331(3) 0.0310(13) Uani 1 1 d . . .
C4A C 0.6337(11) 0.3899(3) -0.0158(3) 0.0360(14) Uani 1 1 d . . .
C5A C 0.8215(11) 0.3425(3) 0.0015(3) 0.0321(13) Uani 1 1 d . . .
C6A C 0.8296(10) 0.3150(3) 0.0675(3) 0.0290(12) Uani 1 1 d . . .
O1B O 1.0671(7) 0.23291(18) 0.23918(17) 0.0367(9) Uani 1 1 d . . .
H1B H 0.9408 0.2501 0.2115 0.044 Uiso 1 1 d R . .
F2B F 0.7162(6) 0.14058(15) 0.17920(16) 0.0397(8) Uani 1 1 d . . .
F3B F 0.7573(7) 0.00046(16) 0.20329(17) 0.0460(8) Uani 1 1 d . . .
F4B F 1.1465(6) -0.04939(15) 0.28769(16) 0.0421(8) Uani 1 1 d . . .
F5B F 1.4848(6) 0.04160(15) 0.34751(15) 0.0430(9) Uani 1 1 d . . .
F6B F 1.4462(6) 0.18107(15) 0.32193(16) 0.0416(8) Uani 1 1 d . . .
C1B C 1.0801(10) 0.1628(3) 0.2503(2) 0.0291(12) Uani 1 1 d . . .
C2B C 0.9085(10) 0.1153(3) 0.2210(3) 0.0297(12) Uani 1 1 d . . .
C3B C 0.9281(10) 0.0444(3) 0.2331(3) 0.0303(12) Uani 1 1 d . . .
C4B C 1.1230(11) 0.0193(3) 0.2755(3) 0.0329(13) Uani 1 1 d . . .
C5B C 1.2962(10) 0.0663(3) 0.3051(3) 0.0293(12) Uani 1 1 d . . .
C6B C 1.2747(10) 0.1362(3) 0.2930(2) 0.0290(12) Uani 1 1 d . . .
O1C O 0.3564(7) 0.33624(18) 0.29755(16) 0.0329(9) Uani 1 1 d . . .
H1C H 0.2517 0.2989 0.2916 0.039 Uiso 1 1 d R . .
F2C F 0.0015(6) 0.27669(16) 0.38961(14) 0.0382(8) Uani 1 1 d . . .
F3C F 0.0265(6) 0.30438(17) 0.52814(14) 0.0464(9) Uani 1 1 d . . .
F4C F 0.4057(6) 0.39026(17) 0.57947(14) 0.0461(9) Uani 1 1 d . . .
F5C F 0.7571(6) 0.44838(17) 0.49034(16) 0.0448(8) Uani 1 1 d . . .
F6C F 0.7320(6) 0.42077(17) 0.35152(16) 0.0433(8) Uani 1 1 d . . .
C1C C 0.3661(10) 0.3487(3) 0.3683(2) 0.0266(12) Uani 1 1 d . . .
C2C C 0.1885(10) 0.3200(2) 0.4140(3) 0.0266(12) Uani 1 1 d . . .
C3C C 0.2013(10) 0.3340(3) 0.4851(2) 0.0278(12) Uani 1 1 d . . .
C4C C 0.3918(11) 0.3765(3) 0.5100(3) 0.0304(12) Uani 1 1 d . . .
C5C C 0.5699(10) 0.4063(3) 0.4659(3) 0.0308(13) Uani 1 1 d . . .
C6C C 0.5531(10) 0.3924(3) 0.3942(3) 0.0280(12) 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'
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'
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
C1A O1A H1A 104.7 . . ?
C2A C1A O1A 122.7(4) . . ?
C2A C1A C6A 118.5(5) . . ?
O1A C1A C6A 118.7(4) . . ?
F2A C2A C1A 119.6(5) . . ?
F2A C2A C3A 119.2(5) . . ?
C1A C2A C3A 121.2(5) . . ?
F3A C3A C4A 120.6(5) . . ?
F3A C3A C2A 120.3(5) . . ?
C4A C3A C2A 119.1(5) . . ?
F4A C4A C5A 119.6(5) . . ?
F4A C4A C3A 120.2(5) . . ?
C5A C4A C3A 120.2(5) . . ?
F5A C5A C4A 120.3(5) . . ?
F5A C5A C6A 119.7(5) . . ?
C4A C5A C6A 120.0(5) . . ?
F6A C6A C5A 119.5(5) . . ?
F6A C6A C1A 119.5(4) . . ?
C5A C6A C1A 120.9(5) . . ?
C1B O1B H1B 119.2 . . ?
O1B C1B C2B 123.4(5) . . ?
O1B C1B C6B 119.2(5) . . ?
C2B C1B C6B 117.4(5) . . ?
F2B C2B C3B 120.0(5) . . ?
F2B C2B C1B 118.0(4) . . ?
C3B C2B C1B 122.0(5) . . ?
F3B C3B C2B 119.7(5) . . ?
F3B C3B C4B 120.6(5) . . ?
C2B C3B C4B 119.6(5) . . ?
F4B C4B C3B 120.7(5) . . ?
F4B C4B C5B 120.4(5) . . ?
C3B C4B C5B 118.9(5) . . ?
F5B C5B C6B 120.3(5) . . ?
F5B C5B C4B 118.7(4) . . ?
C6B C5B C4B 121.0(5) . . ?
F6B C6B C5B 120.0(5) . . ?
F6B C6B C1B 118.8(4) . . ?
C5B C6B C1B 121.2(5) . . ?
C1C O1C H1C 106.4 . . ?
C6C C1C O1C 119.3(4) . . ?
C6C C1C C2C 118.6(4) . . ?
O1C C1C C2C 122.1(5) . . ?
F2C C2C C1C 119.7(4) . . ?
F2C C2C C3C 119.3(4) . . ?
C1C C2C C3C 121.0(5) . . ?
F3C C3C C4C 121.2(4) . . ?
F3C C3C C2C 119.3(5) . . ?
C4C C3C C2C 119.5(5) . . ?
F4C C4C C3C 119.8(5) . . ?
F4C C4C C5C 119.3(5) . . ?
C3C C4C C5C 120.9(5) . . ?
F5C C5C C4C 120.9(5) . . ?
F5C C5C C6C 120.1(5) . . ?
C4C C5C C6C 119.0(5) . . ?
F6C C6C C1C 120.4(4) . . ?
F6C C6C C5C 118.5(5) . . ?
C1C C6C C5C 121.0(5) . . ?
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
O1A C1A 1.379(6) . ?
O1A H1A 0.9642 . ?
F2A C2A 1.347(6) . ?
F3A C3A 1.340(6) . ?
F4A C4A 1.357(6) . ?
F5A C5A 1.354(6) . ?
F6A C6A 1.356(6) . ?
C1A C2A 1.362(7) . ?
C1A C6A 1.380(7) . ?
C2A C3A 1.387(7) . ?
C3A C4A 1.374(7) . ?
C4A C5A 1.364(7) . ?
C5A C6A 1.370(7) . ?
O1B C1B 1.358(6) . ?
O1B H1B 0.9000 . ?
F2B C2B 1.361(6) . ?
F3B C3B 1.342(6) . ?
F4B C4B 1.337(6) . ?
F5B C5B 1.351(5) . ?
F6B C6B 1.348(5) . ?
C1B C2B 1.383(7) . ?
C1B C6B 1.388(7) . ?
C2B C3B 1.377(7) . ?
C3B C4B 1.376(7) . ?
C4B C5B 1.386(7) . ?
C5B C6B 1.358(7) . ?
O1C C1C 1.377(6) . ?
O1C H1C 0.9001 . ?
F2C C2C 1.351(5) . ?
F3C C3C 1.344(5) . ?
F4C C4C 1.357(5) . ?
F5C C5C 1.338(6) . ?
F6C C6C 1.345(5) . ?
C1C C6C 1.365(7) . ?
C1C C2C 1.378(7) . ?
C2C C3C 1.389(7) . ?
C3C C4C 1.359(7) . ?
C4C C5C 1.370(7) . ?
C5C C6C 1.400(7) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1A H1A O1C 0.96 1.97 2.774(5) 140 .
O1B H1B O1A 0.90 1.84 2.703(5) 159 .
O1C H1C O1B 0.90 1.87 2.711(5) 155 1_455
