#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/26/7202684.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_7202684
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         '2C6F5OH, C6F5NH2'
_chemical_formula_sum            'C18 H4 F15 N O2'
_chemical_formula_weight         551.22
_chemical_name_systematic
;
2,3,4,5,6-pentafluorophenol 2,3,4,5,6-pentafluoroaniline 2:1 adduct
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                90.00
_cell_angle_beta                 114.797(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.1635(16)
_cell_length_b                   5.6554(4)
_cell_length_c                   16.5577(13)
_cell_measurement_reflns_used    2644
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      4
_cell_volume                     1799.0(3)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2004)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2004)
;
_computing_data_reduction
;
CrysAlis RED
;
_computing_molecular_graphics
; Stereochemical Workstation (Siemens, 1989).
Mercury, Version 1.4
(Bruno et al., 2002)
;
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(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  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6745
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         4.08
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.035
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         1975
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0313
_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)+(0.0350P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0608
_reflns_number_gt                1625
_reflns_number_total             1975
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b700245a.txt
_cod_data_source_block           cocryst
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7202684
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'
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 0.56149(13) 0.9079(4) 0.46573(19) 0.0213(6) Uani 1 1 d . . .
H1A H 0.554(2) 0.916(8) 0.411(3) 0.058(14) Uiso 1 1 d . . .
F2A F 0.56938(11) 0.8382(3) 0.63027(15) 0.0244(5) Uani 1 1 d . . .
F3A F 0.51307(11) 0.4533(4) 0.67157(15) 0.0270(6) Uani 1 1 d . . .
F4A F 0.44144(11) 0.1290(4) 0.54291(16) 0.0303(6) Uani 1 1 d . . .
F5A F 0.43034(11) 0.1930(4) 0.37390(17) 0.0274(6) Uani 1 1 d . . .
F6A F 0.48683(10) 0.5785(4) 0.33319(14) 0.0229(5) Uani 1 1 d . . .
C1A C 0.52978(18) 0.7162(6) 0.4814(3) 0.0170(8) Uani 1 1 d . . .
C2A C 0.53455(19) 0.6773(7) 0.5666(3) 0.0190(9) Uani 1 1 d . . .
C3A C 0.50530(19) 0.4835(6) 0.5870(3) 0.0191(8) Uani 1 1 d . . .
C4A C 0.46967(19) 0.3205(6) 0.5230(3) 0.0204(9) Uani 1 1 d . . .
C5A C 0.46394(19) 0.3519(6) 0.4378(3) 0.0202(9) Uani 1 1 d . . .
C6A C 0.49328(18) 0.5476(6) 0.4175(3) 0.0174(8) Uani 1 1 d . . .
O1B O 0.64107(13) 1.2521(5) 0.58357(18) 0.0223(6) Uani 1 1 d . . .
H1B H 0.622(2) 1.115(9) 0.554(3) 0.069(15) Uiso 1 1 d . . .
F2B F 0.70606(11) 1.6347(4) 0.68067(16) 0.0276(6) Uani 1 1 d . . .
F3B F 0.84425(11) 1.7026(4) 0.73586(15) 0.0337(6) Uani 1 1 d . . .
F4B F 0.92226(11) 1.3835(4) 0.69226(17) 0.0373(7) Uani 1 1 d . . .
F5B F 0.85938(12) 0.9907(4) 0.59556(17) 0.0340(6) Uani 1 1 d . . .
F6B F 0.72109(11) 0.9223(3) 0.54248(15) 0.0261(6) Uani 1 1 d . . .
C1B C 0.71063(18) 1.2762(6) 0.6102(3) 0.0167(8) Uani 1 1 d . . .
C2B C 0.7440(2) 1.4736(6) 0.6601(3) 0.0221(10) Uani 1 1 d . . .
C3B C 0.8140(2) 1.5096(6) 0.6874(3) 0.0237(9) Uani 1 1 d . . .
C4B C 0.85334(19) 1.3485(7) 0.6661(3) 0.0245(9) Uani 1 1 d . . .
C5B C 0.8223(2) 1.1506(7) 0.6182(3) 0.0222(9) Uani 1 1 d . . .
C6B C 0.75159(19) 1.1170(6) 0.5909(3) 0.0188(9) Uani 1 1 d . . .
N1C N 0.56934(16) 1.0483(6) 0.3114(2) 0.0231(7) Uani 1 1 d . . .
H2C H 0.5525(19) 0.932(6) 0.271(2) 0.035(11) Uiso 1 1 d . . .
H1C H 0.540(2) 1.173(7) 0.288(3) 0.045(12) Uiso 1 1 d . . .
F2C F 0.65843(12) 0.7561(4) 0.27249(16) 0.0280(5) Uani 1 1 d . . .
F3C F 0.79531(12) 0.8555(4) 0.32815(17) 0.0287(6) Uani 1 1 d . . .
F4C F 0.84932(10) 1.2595(4) 0.42088(15) 0.0287(6) Uani 1 1 d . . .
F5C F 0.76447(12) 1.5650(4) 0.45587(16) 0.0263(6) Uani 1 1 d . . .
F6C F 0.62755(12) 1.4668(4) 0.39942(18) 0.0286(6) Uani 1 1 d . . .
C1C C 0.63949(19) 1.1082(6) 0.3345(3) 0.0176(8) Uani 1 1 d . . .
C2C C 0.6840(2) 0.9582(6) 0.3175(3) 0.0180(9) Uani 1 1 d . . .
C3C C 0.75423(19) 1.0072(6) 0.3460(3) 0.0167(8) Uani 1 1 d . . .
C4C C 0.78117(18) 1.2103(6) 0.3916(3) 0.0197(9) Uani 1 1 d . . .
C5C C 0.7379(2) 1.3669(6) 0.4096(3) 0.0193(9) Uani 1 1 d . . .
C6C C 0.6687(2) 1.3133(6) 0.3813(3) 0.0204(9) 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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A O1A H1A 111(3) . . ?
O1A C1A C2A 119.4(3) . . ?
O1A C1A C6A 124.2(4) . . ?
C2A C1A C6A 116.4(3) . . ?
F2A C2A C3A 120.1(4) . . ?
F2A C2A C1A 118.0(3) . . ?
C3A C2A C1A 122.0(3) . . ?
F3A C3A C4A 120.4(3) . . ?
F3A C3A C2A 119.1(3) . . ?
C4A C3A C2A 120.5(4) . . ?
F4A C4A C3A 120.7(4) . . ?
F4A C4A C5A 119.9(4) . . ?
C3A C4A C5A 119.4(3) . . ?
F5A C5A C4A 120.7(4) . . ?
F5A C5A C6A 119.4(4) . . ?
C4A C5A C6A 119.9(4) . . ?
F6A C6A C5A 119.6(3) . . ?
F6A C6A C1A 118.6(3) . . ?
C5A C6A C1A 121.9(4) . . ?
C1B O1B H1B 116(3) . . ?
O1B C1B C6B 124.3(3) . . ?
O1B C1B C2B 119.0(3) . . ?
C6B C1B C2B 116.7(3) . . ?
F2B C2B C3B 119.5(3) . . ?
F2B C2B C1B 119.0(3) . . ?
C3B C2B C1B 121.5(3) . . ?
F3B C3B C2B 119.6(4) . . ?
F3B C3B C4B 120.1(4) . . ?
C2B C3B C4B 120.3(4) . . ?
F4B C4B C5B 119.8(4) . . ?
F4B C4B C3B 120.6(4) . . ?
C5B C4B C3B 119.6(4) . . ?
F5B C5B C4B 120.9(4) . . ?
F5B C5B C6B 119.5(4) . . ?
C4B C5B C6B 119.5(4) . . ?
F6B C6B C1B 118.6(3) . . ?
F6B C6B C5B 119.1(3) . . ?
C1B C6B C5B 122.3(3) . . ?
C1C N1C H2C 115(2) . . ?
C1C N1C H1C 112(3) . . ?
H2C N1C H1C 106(3) . . ?
C2C C1C C6C 116.4(3) . . ?
C2C C1C N1C 121.8(3) . . ?
C6C C1C N1C 121.6(3) . . ?
F2C C2C C1C 118.9(3) . . ?
F2C C2C C3C 118.8(3) . . ?
C1C C2C C3C 122.2(3) . . ?
F3C C3C C4C 120.2(3) . . ?
F3C C3C C2C 120.0(3) . . ?
C4C C3C C2C 119.8(3) . . ?
F4C C4C C3C 120.7(3) . . ?
F4C C4C C5C 119.6(3) . . ?
C3C C4C C5C 119.7(3) . . ?
F5C C5C C6C 120.7(3) . . ?
F5C C5C C4C 119.9(3) . . ?
C6C C5C C4C 119.3(3) . . ?
F6C C6C C5C 118.6(3) . . ?
F6C C6C C1C 118.9(3) . . ?
C5C C6C C1C 122.5(3) . . ?
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 1.356(4) . ?
O1A H1A 0.85(4) . ?
F2A C2A 1.353(4) . ?
F3A C3A 1.351(4) . ?
F4A C4A 1.343(4) . ?
F5A C5A 1.342(4) . ?
F6A C6A 1.356(4) . ?
C1A C2A 1.388(5) . ?
C1A C6A 1.393(5) . ?
C2A C3A 1.369(5) . ?
C3A C4A 1.368(6) . ?
C4A C5A 1.376(6) . ?
C5A C6A 1.377(6) . ?
O1B C1B 1.355(4) . ?
O1B H1B 0.92(5) . ?
F2B C2B 1.349(4) . ?
F3B C3B 1.347(4) . ?
F4B C4B 1.351(4) . ?
F5B C5B 1.350(4) . ?
F6B C6B 1.356(4) . ?
C1B C6B 1.376(5) . ?
C1B C2B 1.393(5) . ?
C2B C3B 1.371(5) . ?
C3B C4B 1.375(6) . ?
C4B C5B 1.370(5) . ?
C5B C6B 1.382(5) . ?
N1C C1C 1.410(5) . ?
N1C H2C 0.90(4) . ?
N1C H1C 0.91(4) . ?
F2C C2C 1.347(4) . ?
F3C C3C 1.340(4) . ?
F4C C4C 1.344(4) . ?
F5C C5C 1.341(4) . ?
F6C C6C 1.350(4) . ?
C1C C2C 1.381(5) . ?
C1C C6C 1.388(5) . ?
C2C C3C 1.386(5) . ?
C3C C4C 1.361(5) . ?
C4C C5C 1.392(5) . ?
C5C C6C 1.372(5) . ?
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 N1C 0.85(4) 1.96(4) 2.747(5) 153(4) .
O1B H1B O1A 0.92(5) 1.88(5) 2.771(4) 161(4) .
O1B H1B F2A 0.92(5) 2.54(5) 3.060(3) 116(3) .
N1C H1C F4B 0.91(4) 2.35(4) 2.929(3) 121(3) 4_474
N1C H2C F2C 0.90(4) 2.44(4) 2.778(4) 102(3) .
N1C H2C F3A 0.90(4) 2.65(4) 3.537(4) 172(3) 2_564
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21149224
