##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_II
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
2,3,4,5,6-pentafluorophenol--phenazine (2/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     '2(C6 H F5 O), C12 H8 N2'
_chemical_formula_sum     'C24 H10 F10 N2 O2'
_chemical_formula_iupac     '2C6 H F5 O , C12 H8 N2'
_chemical_formula_weight     548.34
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     4.9045(3)
_cell_length_b     17.1342(10)
_cell_length_c     12.6397(6)
_cell_angle_alpha     90.00
_cell_angle_beta     90.931(5)
_cell_angle_gamma     90.00
_cell_volume     1062.03(10)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     766
_cell_measurement_theta_min     3.50
_cell_measurement_theta_max     36.68
_cell_measurement_temperature     130(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.4
_exptl_crystal_size_mid     0.02
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.715
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     548
_exptl_absorpt_coefficient_mu     1.525
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_absorpt_correction_T_min     0.36571
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
;
_diffrn_ambient_temperature     130(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_source     'Nova Cu X-ray Source'
_diffrn_radiation_monochromator     mirror
_diffrn_measurement_device_type     'Oxford SuperNova'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10876
_diffrn_reflns_av_R_equivalents     0.0386
_diffrn_reflns_av_sigmaI/netI     0.0173
_diffrn_reflns_theta_min     4.35
_diffrn_reflns_theta_max     76.43
_diffrn_reflns_theta_full     70.00
_diffrn_measured_fraction_theta_max     0.980
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R-factors based on ALL data will be
even larger.
;
_reflns_number_total     2186
_reflns_number_gt     1939
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0470
_refine_ls_R_factor_gt     0.0429
_refine_ls_wR_factor_gt     0.1213
_refine_ls_wR_factor_ref     0.1261
_refine_ls_goodness_of_fit_ref     1.106
_refine_ls_restrained_S_all     1.106
_refine_ls_number_reflns     2186
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0693P)²+0.4475P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.217
_refine_diff_density_min     -0.292
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0727 0.0534
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_cell_refinement     'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction     'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.5692(3) 0.47309(8) 0.60219(10) 0.0280(3) Uani d . 1 1 . .
    C C2 0.3726(3) 0.52675(9) 0.58729(12) 0.0277(3) Uani d . 1 1 . .
    C C3 0.2287(4) 0.55680(10) 0.67487(13) 0.0339(4) Uani d . 1 1 . .
    H H3 0.2709 0.5389 0.7444 0.041 Uiso calc R 1 1 . .
    C C4 0.0303(4) 0.61123(11) 0.65930(15) 0.0391(4) Uani d . 1 1 . .
    H H4 -0.0649 0.6311 0.7184 0.047 Uiso calc R 1 1 . .
    C C5 0.6965(3) 0.44559(9) 0.51709(12) 0.0279(3) Uani d . 1 1 . .
    C C6 0.9056(4) 0.38864(10) 0.52960(14) 0.0333(4) Uani d . 1 1 . .
    H H6 0.9533 0.3699 0.5982 0.040 Uiso calc R 1 1 . .
    C C7 1.0369(4) 0.36105(10) 0.44369(16) 0.0388(4) Uani d . 1 1 . .
    H H7 1.1754 0.3227 0.4525 0.047 Uiso calc R 1 1 . .
    O O1A 0.7405(3) 0.43417(8) 0.80095(10) 0.0376(3) Uani d . 1 1 . .
    H H1A 0.686(6) 0.4419(16) 0.735(2) 0.067(8) Uiso d . 1 1 . .
    F F2A 0.3504(2) 0.33406(6) 0.71111(7) 0.0406(3) Uani d . 1 1 . .
    F F3A -0.0011(2) 0.25622(6) 0.83397(9) 0.0419(3) Uani d . 1 1 . .
    F F4A 0.0300(2) 0.27108(7) 1.04879(9) 0.0473(3) Uani d . 1 1 . .
    F F5A 0.4192(3) 0.36459(8) 1.13705(8) 0.0514(3) Uani d . 1 1 . .
    F F6A 0.7618(2) 0.44587(6) 1.01470(8) 0.0410(3) Uani d . 1 1 . .
    C C1A 0.5628(3) 0.39347(9) 0.85879(12) 0.0294(4) Uani d . 1 1 . .
    C C2A 0.3664(4) 0.34346(10) 0.81657(12) 0.0306(4) Uani d . 1 1 . .
    C C3A 0.1879(4) 0.30303(9) 0.87859(13) 0.0318(4) Uani d . 1 1 . .
    C C4A 0.2037(4) 0.31034(10) 0.98751(14) 0.0342(4) Uani d . 1 1 . .
    C C5A 0.4003(4) 0.35782(11) 1.03161(13) 0.0347(4) Uani d . 1 1 . .
    C C6A 0.5757(4) 0.39901(10) 0.96887(13) 0.0313(4) Uani d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    N1 C5 . 1.338(2) ?
    N1 C2 . 1.343(2) ?
    C2 C3 . 1.419(2) ?
    C2 C5 3_666 1.437(2) ?
    C3 C4 . 1.360(3) ?
    C3 H3 . 0.9500 ?
    C4 C7 3_666 1.419(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.422(2) ?
    C5 C2 3_666 1.437(2) ?
    C6 C7 . 1.356(3) ?
    C6 H6 . 0.9500 ?
    C7 C4 3_666 1.419(3) ?
    C7 H7 . 0.9500 ?
    O1A C1A . 1.342(2) ?
    O1A H1A . 0.88(3) ?
    F2A C2A . 1.3437(18) ?
    F3A C3A . 1.343(2) ?
    F4A C4A . 1.341(2) ?
    F5A C5A . 1.3395(19) ?
    F6A C6A . 1.340(2) ?
    C1A C2A . 1.390(2) ?
    C1A C6A . 1.395(2) ?
    C2A C3A . 1.372(2) ?
    C3A C4A . 1.383(2) ?
    C4A C5A . 1.373(3) ?
    C5A C6A . 1.374(3) ?
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
    C5 N1 C2 . . 118.14(14) ?
    N1 C2 C3 . . 120.26(15) ?
    N1 C2 C5 . 3_666 120.83(15) ?
    C3 C2 C5 . 3_666 118.90(16) ?
    C4 C3 C2 . . 119.99(16) ?
    C4 C3 H3 . . 120.0 ?
    C2 C3 H3 . . 120.0 ?
    C3 C4 C7 . 3_666 121.14(16) ?
    C3 C4 H4 . . 119.4 ?
    C7 C4 H4 3_666 . 119.4 ?
    N1 C5 C6 . . 119.82(15) ?
    N1 C5 C2 . 3_666 121.02(15) ?
    C6 C5 C2 . 3_666 119.16(15) ?
    C7 C6 C5 . . 120.05(16) ?
    C7 C6 H6 . . 120.0 ?
    C5 C6 H6 . . 120.0 ?
    C6 C7 C4 . 3_666 120.76(17) ?
    C6 C7 H7 . . 119.6 ?
    C4 C7 H7 3_666 . 119.6 ?
    C1A O1A H1A . . 113.7(19) ?
    O1A C1A C2A . . 124.30(15) ?
    O1A C1A C6A . . 119.27(15) ?
    C2A C1A C6A . . 116.41(15) ?
    F2A C2A C3A . . 118.61(15) ?
    F2A C2A C1A . . 118.94(15) ?
    C3A C2A C1A . . 122.46(15) ?
    F3A C3A C2A . . 120.26(15) ?
    F3A C3A C4A . . 119.94(15) ?
    C2A C3A C4A . . 119.80(16) ?
    F4A C4A C5A . . 120.74(16) ?
    F4A C4A C3A . . 120.23(17) ?
    C5A C4A C3A . . 119.03(16) ?
    F5A C5A C4A . . 119.46(16) ?
    F5A C5A C6A . . 119.73(16) ?
    C4A C5A C6A . . 120.80(15) ?
    F6A C6A C5A . . 119.11(14) ?
    F6A C6A C1A . . 119.41(15) ?
    C5A C6A C1A . . 121.47(16) ?
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
    O1A H1A N1 . 0.88(3) 1.85(3) 2.7192(18) 172(3)
    C4 H4 F5A 3_567 0.95 2.54 3.441(2) 158
    C6 H6 F2A 1_655 0.95 2.47 3.276(2) 142
data_global
_journal_date_recd_electronic     2011-06-14
_journal_date_accepted     2011-07-11
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2011
_journal_volume     67
_journal_issue      9
_journal_page_first     o341
_journal_page_last     o345
_journal_paper_category     FO
_journal_coeditor_code     SU3067
_publ_contact_author_name     'Maria Gdaniec'
_publ_contact_author_address
;
Faculty of Chemistry
Adam Mickiewicz University
60-780 Poznań
Poland
;
_publ_contact_author_email     magdan@amu.edu.pl
_publ_contact_author_fax     '048 61 8658008'
_publ_contact_author_phone     '048 61 8291273'
_publ_section_title
;
5:1 and 2:1 cocrystals of 2,3,4,5,6-pentafluorophenol with phenazine
;
loop_
    _publ_author_name
    _publ_author_address
    'Czapik, Agnieszka'
;
Faculty of Chemistry
Adam Mickiewicz University
60-780 Poznań
Poland
;
    'Gdaniec, Maria'
;
Faculty of Chemistry
Adam Mickiewicz University
60-780 Poznań
Poland
;
data_I
_chemical_name_systematic
;
2,3,4,5,6-pentafluorophenol--phenazine (5/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     '5(C6 H F5 O), C12 H8 N2'
_chemical_formula_sum     'C42 H13 F25 N2 O5'
_chemical_formula_iupac     '5C6 H F5 O , C12 H8 N2'
_chemical_formula_weight     1100.54
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     16.1015(7)
_cell_length_b     4.5223(2)
_cell_length_c     27.4753(12)
_cell_angle_alpha     90.00
_cell_angle_beta     97.315(4)
_cell_angle_gamma     90.00
_cell_volume     1984.35(15)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1638
_cell_measurement_theta_min     3.38
_cell_measurement_theta_max     56.62
_cell_measurement_temperature     130(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.2
_exptl_crystal_size_mid     0.05
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.842
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1088
_exptl_absorpt_coefficient_mu     1.824
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_absorpt_correction_T_min     0.671
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details
;
;
_diffrn_ambient_temperature     130(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_source     'Nova Cu X-ray Source'
_diffrn_radiation_monochromator     mirror
_diffrn_measurement_device_type     'Oxford SuperNova'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13006
_diffrn_reflns_av_R_equivalents     0.0346
_diffrn_reflns_av_sigmaI/netI     0.0245
_diffrn_reflns_theta_min     3.24
_diffrn_reflns_theta_max     76.63
_diffrn_reflns_theta_full     70.00
_diffrn_measured_fraction_theta_max     0.980
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -20
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -5
_diffrn_reflns_limit_k_max     4
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     34
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R-factors based on ALL data will be
even larger.
;
_reflns_number_total     4098
_reflns_number_gt     3460
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0483
_refine_ls_R_factor_gt     0.0405
_refine_ls_wR_factor_gt     0.1096
_refine_ls_wR_factor_ref     0.1147
_refine_ls_goodness_of_fit_ref     1.076
_refine_ls_restrained_S_all     1.076
_refine_ls_number_reflns     4098
_refine_ls_number_parameters     342
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0645P)²+0.5930P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.273
_refine_diff_density_min     -0.262
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0727 0.0534
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_cell_refinement     'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction     'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.46750(9) 0.0873(3) 0.04301(5) 0.0265(3) Uani d . 1 1 . .
    C C2 0.53374(10) -0.0948(4) 0.04505(6) 0.0263(3) Uani d . 1 1 . .
    C C3 0.57197(12) -0.2024(4) 0.09113(6) 0.0345(4) Uani d . 1 1 . .
    H H3 0.5506 -0.1460 0.1204 0.041 Uiso calc R 1 1 . .
    C C4 0.63905(12) -0.3859(5) 0.09324(7) 0.0402(5) Uani d . 1 1 . .
    H H4 0.6643 -0.4569 0.1242 0.048 Uiso calc R 1 1 . .
    C C5 0.43300(10) 0.1837(4) -0.00133(6) 0.0260(3) Uani d . 1 1 . .
    C C6 0.36263(11) 0.3749(4) -0.00517(7) 0.0338(4) Uani d . 1 1 . .
    H H6 0.3398 0.4343 0.0235 0.041 Uiso calc R 1 1 . .
    C C7 0.32796(12) 0.4731(5) -0.04998(7) 0.0397(4) Uani d . 1 1 . .
    H H7 0.2810 0.6018 -0.0523 0.048 Uiso calc R 1 1 . .
    O O1A 0.41726(8) 0.2525(3) 0.12785(4) 0.0326(3) Uani d . 1 1 . .
    H H1A 0.4259(19) 0.186(7) 0.0983(12) 0.086(10) Uiso d . 1 1 . .
    F F2A 0.31296(7) -0.1673(3) 0.07556(4) 0.0383(3) Uani d . 1 1 . .
    F F3A 0.16114(7) -0.2883(2) 0.10186(4) 0.0363(3) Uani d . 1 1 . .
    F F4A 0.10460(7) 0.0113(2) 0.17736(4) 0.0372(3) Uani d . 1 1 . .
    F F5A 0.20255(6) 0.4366(2) 0.22530(3) 0.0328(2) Uani d . 1 1 . .
    F F6A 0.35776(6) 0.5436(2) 0.20135(3) 0.0310(2) Uani d . 1 1 . .
    C C1A 0.33918(10) 0.1912(4) 0.13791(6) 0.0251(3) Uani d . 1 1 . .
    C C2A 0.28644(11) -0.0171(4) 0.11310(6) 0.0270(4) Uani d . 1 1 . .
    C C3A 0.20859(11) -0.0785(4) 0.12605(6) 0.0276(4) Uani d . 1 1 . .
    C C4A 0.18002(10) 0.0710(4) 0.16426(6) 0.0269(3) Uani d . 1 1 . .
    C C5A 0.23054(11) 0.2843(4) 0.18903(6) 0.0255(3) Uani d . 1 1 . .
    C C6A 0.30897(10) 0.3388(4) 0.17637(5) 0.0243(3) Uani d . 1 1 . .
    O O1B 0.55409(9) 0.4472(4) 0.18868(5) 0.0427(4) Uani d . 1 1 . .
    H H1B 0.5079(19) 0.374(7) 0.1768(11) 0.076(9) Uiso d . 1 1 . .
    F F2B 0.46806(7) 0.0542(3) 0.24287(4) 0.0418(3) Uani d . 1 1 . .
    F F3B 0.51478(8) -0.0064(3) 0.34095(4) 0.0488(3) Uani d . 1 1 . .
    F F4B 0.64597(10) 0.3099(3) 0.38614(4) 0.0608(4) Uani d . 1 1 . .
    F F5B 0.73003(8) 0.6878(3) 0.33262(5) 0.0586(4) Uani d . 1 1 . .
    F F6B 0.68262(7) 0.7523(3) 0.23533(5) 0.0472(3) Uani d . 1 1 . .
    C C1B 0.57390(11) 0.4058(4) 0.23734(6) 0.0301(4) Uani d . 1 1 . .
    C C2B 0.53249(11) 0.2137(4) 0.26516(6) 0.0303(4) Uani d . 1 1 . .
    C C3B 0.55610(12) 0.1797(4) 0.31484(7) 0.0334(4) Uani d . 1 1 . .
    C C4B 0.62270(13) 0.3403(5) 0.33746(7) 0.0381(4) Uani d . 1 1 . .
    C C5B 0.66516(12) 0.5306(4) 0.31077(7) 0.0377(4) Uani d . 1 1 . .
    C C6B 0.64082(11) 0.5635(4) 0.26092(7) 0.0328(4) Uani d . 1 1 . .
    F F1C 0.47372(8) 0.5849(3) 0.42814(4) 0.0514(3) Uani d . 1 1 . .
    F F2C 0.63056(8) 0.8047(3) 0.45430(5) 0.0492(3) Uani d P 0.50 1 . .
    O O2C' 0.63056(8) 0.8047(3) 0.45430(5) 0.0492(3) Uani d P 0.50 1 . .
    H H1C 0.6131 0.6577 0.4366 0.059 Uiso d PR 0.50 1 . .
    F F3C 0.65595(7) 1.2258(3) 0.52524(4) 0.0489(3) Uani d . 1 1 . .
    C C1C 0.48623(12) 0.7905(4) 0.46366(6) 0.0368(4) Uani d . 1 1 . .
    C C2C 0.56587(12) 0.9018(5) 0.47641(7) 0.0381(4) Uani d . 1 1 . .
    C C3C 0.57900(12) 1.1134(5) 0.51284(7) 0.0364(4) Uani d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    N1 C2 . 1.343(2) ?
    N1 C5 . 1.345(2) ?
    C2 C3 . 1.421(2) ?
    C2 C5 3_655 1.433(2) ?
    C3 C4 . 1.357(3) ?
    C3 H3 . 0.9500 ?
    C4 C7 3_655 1.418(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.419(2) ?
    C5 C2 3_655 1.433(2) ?
    C6 C7 . 1.360(3) ?
    C6 H6 . 0.9500 ?
    C7 C4 3_655 1.418(3) ?
    C7 H7 . 0.9500 ?
    O1A C1A . 1.350(2) ?
    O1A H1A . 0.89(3) ?
    F2A C2A . 1.3491(18) ?
    F3A C3A . 1.3404(19) ?
    F4A C4A . 1.3374(19) ?
    F5A C5A . 1.3360(18) ?
    F6A C6A . 1.3450(18) ?
    C1A C2A . 1.388(2) ?
    C1A C6A . 1.389(2) ?
    C2A C3A . 1.374(2) ?
    C3A C4A . 1.376(2) ?
    C4A C5A . 1.384(2) ?
    C5A C6A . 1.374(2) ?
    O1B C1B . 1.348(2) ?
    O1B H1B . 0.84(3) ?
    F2B C2B . 1.345(2) ?
    F3B C3B . 1.337(2) ?
    F4B C4B . 1.349(2) ?
    F5B C5B . 1.341(2) ?
    F6B C6B . 1.340(2) ?
    C1B C6B . 1.383(3) ?
    C1B C2B . 1.383(2) ?
    C2B C3B . 1.378(3) ?
    C3B C4B . 1.376(3) ?
    C4B C5B . 1.369(3) ?
    C5B C6B . 1.384(3) ?
    F1C C1C . 1.344(2) ?
    F2C C2C . 1.345(2) ?
    F2C H1C . 0.8501 ?
    F3C C3C . 1.343(2) ?
    C1C C3C 3_676 1.372(3) ?
    C1C C2C . 1.381(3) ?
    C2C C3C . 1.381(3) ?
    C3C C1C 3_676 1.372(3) ?
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
    C2 N1 C5 . . 118.06(14) ?
    N1 C2 C3 . . 119.90(15) ?
    N1 C2 C5 . 3_655 121.09(15) ?
    C3 C2 C5 . 3_655 119.01(16) ?
    C4 C3 C2 . . 119.95(16) ?
    C4 C3 H3 . . 120.0 ?
    C2 C3 H3 . . 120.0 ?
    C3 C4 C7 . 3_655 121.01(17) ?
    C3 C4 H4 . . 119.5 ?
    C7 C4 H4 3_655 . 119.5 ?
    N1 C5 C6 . . 119.90(15) ?
    N1 C5 C2 . 3_655 120.85(15) ?
    C6 C5 C2 . 3_655 119.25(15) ?
    C7 C6 C5 . . 119.88(16) ?
    C7 C6 H6 . . 120.1 ?
    C5 C6 H6 . . 120.1 ?
    C6 C7 C4 . 3_655 120.90(18) ?
    C6 C7 H7 . . 119.5 ?
    C4 C7 H7 3_655 . 119.5 ?
    C1A O1A H1A . . 112(2) ?
    O1A C1A C2A . . 124.50(15) ?
    O1A C1A C6A . . 118.85(15) ?
    C2A C1A C6A . . 116.63(15) ?
    F2A C2A C3A . . 118.96(15) ?
    F2A C2A C1A . . 118.94(15) ?
    C3A C2A C1A . . 122.10(15) ?
    F3A C3A C2A . . 119.72(15) ?
    F3A C3A C4A . . 120.08(16) ?
    C2A C3A C4A . . 120.19(15) ?
    F4A C4A C3A . . 120.63(16) ?
    F4A C4A C5A . . 120.35(15) ?
    C3A C4A C5A . . 119.02(16) ?
    F5A C5A C6A . . 120.30(15) ?
    F5A C5A C4A . . 119.56(15) ?
    C6A C5A C4A . . 120.14(15) ?
    F6A C6A C5A . . 119.34(14) ?
    F6A C6A C1A . . 118.75(14) ?
    C5A C6A C1A . . 121.90(15) ?
    C1B O1B H1B . . 115(2) ?
    O1B C1B C6B . . 117.72(16) ?
    O1B C1B C2B . . 124.44(16) ?
    C6B C1B C2B . . 117.83(16) ?
    F2B C2B C3B . . 119.40(16) ?
    F2B C2B C1B . . 118.88(15) ?
    C3B C2B C1B . . 121.71(17) ?
    F3B C3B C4B . . 120.16(17) ?
    F3B C3B C2B . . 120.55(17) ?
    C4B C3B C2B . . 119.30(17) ?
    F4B C4B C5B . . 120.04(19) ?
    F4B C4B C3B . . 119.73(19) ?
    C5B C4B C3B . . 120.24(17) ?
    F5B C5B C4B . . 120.49(18) ?
    F5B C5B C6B . . 119.51(19) ?
    C4B C5B C6B . . 120.00(17) ?
    F6B C6B C1B . . 119.75(17) ?
    F6B C6B C5B . . 119.33(17) ?
    C1B C6B C5B . . 120.92(17) ?
    C2C F2C H1C . . 107.1 ?
    F1C C1C C3C . 3_676 120.52(18) ?
    F1C C1C C2C . . 119.01(19) ?
    C3C C1C C2C 3_676 . 120.47(19) ?
    F2C C2C C1C . . 120.94(19) ?
    F2C C2C C3C . . 119.85(18) ?
    C1C C2C C3C . . 119.21(19) ?
    F3C C3C C1C . 3_676 119.84(18) ?
    F3C C3C C2C . . 119.84(19) ?
    C1C C3C C2C 3_676 . 120.32(18) ?
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
    O1A H1A N1 . 0.89(3) 1.79(3) 2.6693(18) 167(3)
    O1B H1B O1A . 0.84(3) 1.93(3) 2.7358(19) 159(3)
    O2C' H1C F4B . 0.85 2.21 2.948(2) 146
    C6 H6 F2A 1_565 0.95 2.37 3.209(2) 147
    C7 H7 F2C/O2C 4_575 0.95 2.49 3.350(2) 151
    C4 H4 F5B 2_635 0.95 2.52 3.349(2) 145
    C4 H4 O1B 1_545 0.95 2.70 3.199(2) 114
    C3 H3 O1B 1_545 0.95 2.62 3.158(2) 116
