##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# 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_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
pyrazine--2,3,5,6-tetrafluorobenzene-1,4-diol (1/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H2 F4 O2 , C4 H4 N2'
_chemical_formula_sum     'C10 H6 F4 N2 O2'
_chemical_formula_iupac     'C6 H2 F4 O2 , C4 H4 N2'
_chemical_formula_weight     262.17
_chemical_melting_point     ?
_chemical_melting_point_gt     444
_chemical_melting_point_lt     446
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     3.6671(10)
_cell_length_b     7.585(2)
_cell_length_c     9.582(2)
_cell_angle_alpha     88.14(2)
_cell_angle_beta     85.67(2)
_cell_angle_gamma     77.41(2)
_cell_volume     259.34(11)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     1281
_cell_measurement_theta_min     4
_cell_measurement_theta_max     25
_cell_measurement_temperature     294(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.679
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     132
_exptl_absorpt_coefficient_mu     0.165
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Kuma KM-4 CCD κ geometry'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     1921
_diffrn_reflns_av_R_equivalents     0.0411
_diffrn_reflns_av_sigmaI/netI     0.0352
_diffrn_reflns_theta_min     3.51
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -3
_diffrn_reflns_limit_h_max     4
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     ?
_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     917
_reflns_number_gt     791
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0562
_refine_ls_R_factor_gt     0.0482
_refine_ls_wR_factor_gt     0.1242
_refine_ls_wR_factor_ref     0.1321
_refine_ls_goodness_of_fit_ref     1.075
_refine_ls_restrained_S_all     1.075
_refine_ls_number_reflns     917
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0994P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_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     0.372
_refine_diff_density_min     -0.305
_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' 0.0033 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'
    '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'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2004)'
_computing_cell_refinement     'CrysAlis CCD (Oxford Diffraction, 2004)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2004)'
_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.,
2006)
;
_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_disorder_assembly
    _atom_site_disorder_group
    O O1 0.7507(4) 0.47473(16) 0.21929(11) 0.0489(4) Uani d . 1 . .
    H H1O 0.7952 0.3679 0.1883 0.059 Uiso d R 1 . .
    F F2 0.5369(4) 0.18462(13) 0.37105(11) 0.0566(4) Uani d . 1 . .
    F F3 0.6964(3) 0.78291(13) 0.35828(10) 0.0503(4) Uani d . 1 . .
    C C1 0.6268(4) 0.4821(2) 0.35599(15) 0.0334(4) Uani d . 1 . .
    C C2 0.5227(5) 0.3426(2) 0.43377(16) 0.0357(4) Uani d . 1 . .
    C C3 0.5985(4) 0.6411(2) 0.42691(16) 0.0337(4) Uani d . 1 . .
    N N1A 0.9210(4) 0.15481(19) 0.08028(13) 0.0400(4) Uani d . 1 . .
    C C2A 1.0880(5) -0.0050(2) 0.13160(16) 0.0398(5) Uani d . 1 . .
    H H2A 1.1431 -0.0128 0.2282 0.048 Uiso d R 1 . .
    C C3A 0.8336(5) 0.1583(2) -0.05265(16) 0.0410(5) Uani d . 1 . .
    H H3A 0.7227 0.2747 -0.0906 0.049 Uiso d R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0776(9) 0.0364(8) 0.0306(7) -0.0117(6) 0.0095(6) -0.0048(5)
    F2 0.0937(9) 0.0318(6) 0.0470(6) -0.0225(6) 0.0105(6) -0.0148(4)
    F3 0.0744(8) 0.0310(6) 0.0462(6) -0.0176(5) 0.0070(5) 0.0043(4)
    C1 0.0379(9) 0.0317(9) 0.0292(8) -0.0044(7) -0.0018(6) -0.0021(6)
    C2 0.0438(9) 0.0259(9) 0.0372(9) -0.0060(7) -0.0025(7) -0.0067(6)
    C3 0.0381(9) 0.0267(9) 0.0359(8) -0.0068(6) -0.0009(7) 0.0025(6)
    N1A 0.0463(9) 0.0385(9) 0.0344(8) -0.0088(7) 0.0036(6) -0.0057(6)
    C2A 0.0449(10) 0.0459(10) 0.0286(8) -0.0101(8) -0.0008(7) -0.0011(6)
    C3A 0.0462(10) 0.0385(10) 0.0349(8) -0.0035(7) 0.0017(7) 0.0009(7)
_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
    O1 C1 . 1.352(2) y
    O1 H1O . 0.8500 ?
    F2 C2 . 1.3473(19) ?
    F3 C3 . 1.3438(19) ?
    C1 C2 . 1.379(2) ?
    C1 C3 . 1.383(2) ?
    C3 C2 2_666 1.375(2) ?
    N1A C2A . 1.330(2) ?
    N1A C3A . 1.335(2) ?
    C2A C3A 2_755 1.373(2) ?
    C2A H2A . 0.9600 ?
    C3A H3A . 0.9601 ?
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
    C1 O1 H1O . . 112.3 ?
    O1 C1 C2 . . 125.50(15) y
    O1 C1 C3 . . 118.87(14) y
    C2 C1 C3 . . 115.62(15) y
    F2 C2 C3 . 2_666 118.52(15) ?
    F2 C2 C1 . . 118.96(14) ?
    C3 C2 C1 2_666 . 122.51(16) ?
    F3 C3 C2 . 2_666 119.02(15) ?
    F3 C3 C1 . . 119.11(14) ?
    C2 C3 C1 2_666 . 121.86(15) ?
    C2A N1A C3A . . 116.30(14) ?
    N1A C2A C3A . 2_755 122.05(14) ?
    N1A C2A H2A . . 118.2 ?
    C3A C2A H2A 2_755 . 119.7 ?
    N1A C3A C2A . 2_755 121.64(15) ?
    N1A C3A H3A . . 116.1 ?
    C2A C3A H3A 2_755 . 122.2 ?
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
    O1 H1O N1A . 0.85 1.90 2.7343(19) 167
    C2A H2A F3 1_645 0.96 2.64 3.350(2) 131
    C3A H3A O1 2_665 0.96 2.62 3.538(2) 159
data_II
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
quinoxaline--2,3,5,6-tetrafluorobenzene-1,4-diol (1/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H6 N2 , C6 H2 F4 O2'
_chemical_formula_sum     'C14 H8 F4 N2 O2'
_chemical_formula_iupac     'C8 H6 N2 , C6 H2 F4 O2'
_chemical_formula_weight     312.22
_chemical_melting_point     ?
_chemical_melting_point_gt     439
_chemical_melting_point_lt     441
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
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'
_cell_length_a     7.2094(5)
_cell_length_b     7.4290(4)
_cell_length_c     23.585(13)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1263.2(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4532
_cell_measurement_theta_min     4
_cell_measurement_theta_max     25
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.40
_exptl_crystal_density_diffrn     1.642
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     632
_exptl_absorpt_coefficient_mu     0.151
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Kuma KM-4 CCD κ geometry'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6629
_diffrn_reflns_av_R_equivalents     0.0374
_diffrn_reflns_av_sigmaI/netI     0.0249
_diffrn_reflns_theta_min     3.77
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -4
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     28
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_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     1324
_reflns_number_gt     1208
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0332
_refine_ls_R_factor_gt     0.0306
_refine_ls_wR_factor_gt     0.0817
_refine_ls_wR_factor_ref     0.0837
_refine_ls_goodness_of_fit_ref     1.063
_refine_ls_restrained_S_all     1.063
_refine_ls_number_reflns     1324
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0601P)²+0.0889P] 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     0.174
_refine_diff_density_min     -0.150
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.062(6)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    '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'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2004)'
_computing_cell_refinement     'CrysAlis CCD (Oxford Diffraction, 2004)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2004)'
_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.,
2006)
;
_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_disorder_assembly
    _atom_site_disorder_group
    O O1 0.4547(2) 0.3567(3) 0.76926(6) 0.0568(5) Uani d . 1 . .
    H H1O 0.4780 0.3742 0.7344 0.068 Uiso d R 1 . .
    F F2 0.79605(19) 0.4874(2) 0.73004(5) 0.0558(5) Uani d . 1 . .
    F F3 1.0550(2) 0.6061(3) 0.80186(5) 0.0620(5) Uani d . 1 . .
    O O4 0.9993(2) 0.6086(3) 0.91562(6) 0.0518(5) Uani d . 1 . .
    H H4O 0.9760 0.5872 0.9503 0.062 Uiso d R 1 . .
    F F5 0.65782(19) 0.4845(2) 0.95518(5) 0.0500(4) Uani d . 1 . .
    F F6 0.3983(2) 0.3604(2) 0.88326(6) 0.0576(4) Uani d . 1 . .
    C C1 0.5882(3) 0.4213(3) 0.80398(8) 0.0367(5) Uani d . 1 . .
    C C2 0.7587(3) 0.4858(3) 0.78606(8) 0.0370(5) Uani d . 1 . .
    C C3 0.8915(3) 0.5472(3) 0.82274(9) 0.0380(5) Uani d . 1 . .
    C C4 0.8635(3) 0.5477(3) 0.88086(9) 0.0357(5) Uani d . 1 . .
    C C5 0.6933(3) 0.4851(3) 0.89873(8) 0.0343(5) Uani d . 1 . .
    C C6 0.5597(3) 0.4221(3) 0.86215(9) 0.0372(5) Uani d . 1 . .
    N N1A 0.4814(3) 0.3946(3) 0.65244(7) 0.0382(5) Uani d . 1 . .
    C C2A 0.6234(3) 0.3385(3) 0.62236(10) 0.0420(6) Uani d . 1 . .
    H H2A 0.7269 0.2851 0.6417 0.050 Uiso d R 1 . .
    C C3A 0.6283(3) 0.3531(3) 0.56264(10) 0.0429(6) Uani d . 1 . .
    H H3A 0.7349 0.3081 0.5428 0.051 Uiso d R 1 . .
    N N4A 0.4930(3) 0.4245(3) 0.53347(7) 0.0393(5) Uani d . 1 . .
    C C5A 0.1906(3) 0.5625(3) 0.53483(9) 0.0398(5) Uani d . 1 . .
    H H5A 0.1920 0.5722 0.4942 0.048 Uiso d R 1 . .
    C C6A 0.0414(3) 0.6228(3) 0.56504(10) 0.0443(6) Uani d . 1 . .
    H H6A -0.0609 0.6775 0.5455 0.053 Uiso d R 1 . .
    C C7A 0.0358(3) 0.6069(3) 0.62460(10) 0.0442(6) Uani d . 1 . .
    H H7A -0.0705 0.6503 0.6450 0.053 Uiso d R 1 . .
    C C8A 0.1790(3) 0.5310(3) 0.65327(9) 0.0399(5) Uani d . 1 . .
    H H8A 0.1735 0.5192 0.6938 0.048 Uiso d R 1 . .
    C C9A 0.3366(3) 0.4690(3) 0.62353(8) 0.0325(5) Uani d . 1 . .
    C C10A 0.3422(3) 0.4848(3) 0.56344(9) 0.0333(5) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0464(9) 0.0918(14) 0.0321(8) -0.0208(11) -0.0045(7) 0.0018(9)
    F2 0.0572(9) 0.0879(11) 0.0224(6) -0.0160(9) 0.0062(6) -0.0016(7)
    F3 0.0508(8) 0.0993(12) 0.0359(7) -0.0306(9) 0.0093(7) -0.0020(8)
    O4 0.0494(9) 0.0770(12) 0.0289(8) -0.0214(10) -0.0010(7) -0.0008(8)
    F5 0.0511(8) 0.0746(10) 0.0242(7) -0.0024(8) 0.0083(6) -0.0010(6)
    F6 0.0390(7) 0.0939(11) 0.0400(7) -0.0141(8) 0.0083(6) 0.0030(8)
    C1 0.0369(11) 0.0458(12) 0.0274(10) -0.0015(11) -0.0030(9) 0.0020(9)
    C2 0.0437(12) 0.0443(12) 0.0231(9) -0.0014(11) 0.0035(9) 0.0001(9)
    C3 0.0368(12) 0.0452(13) 0.0320(11) -0.0059(10) 0.0058(9) 0.0013(10)
    C4 0.0400(11) 0.0393(11) 0.0280(10) -0.0018(10) 0.0000(9) -0.0017(9)
    C5 0.0419(12) 0.0393(11) 0.0217(10) 0.0027(11) 0.0041(8) 0.0013(8)
    C6 0.0321(11) 0.0449(12) 0.0345(10) 0.0019(11) 0.0068(9) 0.0029(10)
    N1A 0.0423(10) 0.0445(11) 0.0279(9) -0.0032(10) -0.0051(8) 0.0005(8)
    C2A 0.0403(13) 0.0484(13) 0.0372(12) 0.0015(11) -0.0060(10) 0.0001(10)
    C3A 0.0391(11) 0.0524(14) 0.0372(12) 0.0022(12) 0.0021(10) -0.0028(10)
    N4A 0.0398(10) 0.0501(11) 0.0279(8) -0.0026(9) 0.0024(8) -0.0014(9)
    C5A 0.0407(12) 0.0484(13) 0.0303(10) -0.0039(11) -0.0074(9) 0.0030(10)
    C6A 0.0395(12) 0.0481(14) 0.0453(13) -0.0025(11) -0.0095(11) 0.0021(11)
    C7A 0.0359(11) 0.0477(13) 0.0490(13) -0.0031(11) 0.0046(10) -0.0031(11)
    C8A 0.0442(12) 0.0455(12) 0.0300(11) -0.0068(12) 0.0040(9) -0.0013(9)
    C9A 0.0350(11) 0.0359(10) 0.0265(10) -0.0080(10) -0.0021(8) -0.0013(8)
    C10A 0.0358(11) 0.0370(11) 0.0270(10) -0.0073(10) -0.0025(9) -0.0001(8)
_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
    O1 C1 . 1.352(3) y
    O1 H1O . 0.8500 ?
    F2 C2 . 1.348(2) ?
    F3 C3 . 1.350(2) ?
    O4 C4 . 1.355(3) y
    O4 H4O . 0.8501 ?
    F5 C5 . 1.356(2) ?
    F6 C6 . 1.346(3) ?
    C1 C2 . 1.385(3) ?
    C1 C6 . 1.387(3) ?
    C2 C3 . 1.369(3) ?
    C3 C4 . 1.385(3) ?
    C4 C5 . 1.379(3) ?
    C5 C6 . 1.375(3) ?
    N1A C2A . 1.313(3) ?
    N1A C9A . 1.364(3) ?
    C2A C3A . 1.413(3) ?
    C2A H2A . 0.9601 ?
    C3A N4A . 1.306(3) ?
    C3A H3A . 0.9600 ?
    N4A C10A . 1.372(3) ?
    C5A C6A . 1.365(3) ?
    C5A C10A . 1.409(3) ?
    C5A H5A . 0.9600 ?
    C6A C7A . 1.410(3) ?
    C6A H6A . 0.9600 ?
    C7A C8A . 1.357(3) ?
    C7A H7A . 0.9600 ?
    C8A C9A . 1.412(3) ?
    C8A H8A . 0.9600 ?
    C9A C10A . 1.423(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
    C1 O1 H1O . . 113.0 ?
    C4 O4 H4O . . 112.1 ?
    O1 C1 C2 . . 124.73(19) y
    O1 C1 C6 . . 119.7(2) y
    C2 C1 C6 . . 115.6(2) y
    F2 C2 C3 . . 118.5(2) ?
    F2 C2 C1 . . 118.6(2) ?
    C3 C2 C1 . . 122.90(19) ?
    F3 C3 C2 . . 119.21(19) ?
    F3 C3 C4 . . 119.2(2) ?
    C2 C3 C4 . . 121.6(2) ?
    O4 C4 C5 . . 124.83(18) y
    O4 C4 C3 . . 119.6(2) y
    C5 C4 C3 . . 115.5(2) y
    F5 C5 C6 . . 118.89(19) ?
    F5 C5 C4 . . 117.97(19) ?
    C6 C5 C4 . . 123.14(18) ?
    F6 C6 C5 . . 119.30(19) ?
    F6 C6 C1 . . 119.5(2) ?
    C5 C6 C1 . . 121.2(2) ?
    C2A N1A C9A . . 117.08(18) ?
    N1A C2A C3A . . 122.2(2) ?
    N1A C2A H2A . . 118.6 ?
    C3A C2A H2A . . 119.1 ?
    N4A C3A C2A . . 122.5(2) ?
    N4A C3A H3A . . 118.8 ?
    C2A C3A H3A . . 118.7 ?
    C3A N4A C10A . . 116.94(18) ?
    C6A C5A C10A . . 119.7(2) ?
    C6A C5A H5A . . 120.3 ?
    C10A C5A H5A . . 120.0 ?
    C5A C6A C7A . . 121.0(2) ?
    C5A C6A H6A . . 119.6 ?
    C7A C6A H6A . . 119.4 ?
    C8A C7A C6A . . 120.6(2) ?
    C8A C7A H7A . . 119.8 ?
    C6A C7A H7A . . 119.6 ?
    C7A C8A C9A . . 120.0(2) ?
    C7A C8A H8A . . 120.2 ?
    C9A C8A H8A . . 119.8 ?
    N1A C9A C8A . . 119.98(18) ?
    N1A C9A C10A . . 120.63(19) ?
    C8A C9A C10A . . 119.4(2) ?
    N4A C10A C5A . . 120.13(19) ?
    N4A C10A C9A . . 120.6(2) ?
    C5A C10A C9A . . 119.3(2) ?
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
    O1 H1O N1A . 0.85 1.94 2.776(3) 168
    O4 H4O N4A 2_665 0.85 1.98 2.791(3) 160
    C2A H2A F3 3_746 0.96 2.45 3.399(3) 169
    C3A H3A O4 3_746 0.96 2.61 3.282(3) 127
    C7A H7A F2 1_455 0.96 2.53 3.156(3) 123
    C6A H6A F5 2_564 0.96 2.54 3.068(3) 114
data_III
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
phenazine--2,3,5,6-tetrafluorobenzene-1,4-diol (2/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     '2C12 H8 N2 , C6 H2 F4 O2'
_chemical_formula_sum     'C30 H18 F4 N4 O2'
_chemical_formula_iupac     '2C12 H8 N2 , C6 H2 F4 O2'
_chemical_formula_weight     542.48
_chemical_melting_point     ?
_chemical_melting_point_gt     474
_chemical_melting_point_lt     475
_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     9.1482(5)
_cell_length_b     11.0393(6)
_cell_length_c     12.4185(8)
_cell_angle_alpha     90.00
_cell_angle_beta     102.585(5)
_cell_angle_gamma     90.00
_cell_volume     1224.01(12)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4663
_cell_measurement_theta_min     4
_cell_measurement_theta_max     25
_cell_measurement_temperature     294(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.472
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     556
_exptl_absorpt_coefficient_mu     0.115
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Kuma KM-4 CCD κ geometry'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8327
_diffrn_reflns_av_R_equivalents     0.0241
_diffrn_reflns_av_sigmaI/netI     0.0219
_diffrn_reflns_theta_min     4.57
_diffrn_reflns_theta_max     26.37
_diffrn_reflns_theta_full     26.37
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_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     2476
_reflns_number_gt     1862
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0536
_refine_ls_R_factor_gt     0.0413
_refine_ls_wR_factor_gt     0.1173
_refine_ls_wR_factor_ref     0.1251
_refine_ls_goodness_of_fit_ref     1.066
_refine_ls_restrained_S_all     1.066
_refine_ls_number_reflns     2476
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0803P)²] 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     0.230
_refine_diff_density_min     -0.197
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.023(5)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    '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'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2004)'
_computing_cell_refinement     'CrysAlis CCD (Oxford Diffraction, 2004)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2004)'
_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.,
2006)
;
_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_disorder_assembly
    _atom_site_disorder_group
    O O1 0.21884(10) 0.41473(9) 0.39769(8) 0.0511(3) Uani d . 1 . .
    H H1O 0.2102 0.3950 0.3304 0.061 Uiso d R 1 . .
    F F2 0.41476(9) 0.51907(8) 0.27740(6) 0.0551(3) Uani d . 1 . .
    F F3 0.68533(9) 0.59817(8) 0.38071(6) 0.0561(3) Uani d . 1 . .
    C C1 0.35657(14) 0.45670(11) 0.44484(10) 0.0360(3) Uani d . 1 . .
    C C2 0.45577(14) 0.50828(11) 0.38841(10) 0.0363(3) Uani d . 1 . .
    C C3 0.59460(14) 0.54945(11) 0.44136(10) 0.0369(3) Uani d . 1 . .
    N N1A 0.14220(11) 0.34095(9) 0.18331(8) 0.0381(3) Uani d . 1 . .
    C C2A 0.23286(13) 0.29055(11) 0.12365(10) 0.0366(3) Uani d . 1 . .
    C C3A 0.38075(15) 0.25496(12) 0.17667(13) 0.0475(4) Uani d . 1 . .
    H H3 0.4142 0.2654 0.2549 0.057 Uiso d R 1 . .
    C C4A 0.47266(17) 0.20697(14) 0.11650(15) 0.0587(4) Uani d . 1 . .
    H H4 0.5721 0.1833 0.1530 0.070 Uiso d R 1 . .
    C C5A 0.42575(17) 0.19064(15) 0.00123(15) 0.0617(5) Uani d . 1 . .
    H H5 0.4939 0.1575 -0.0398 0.074 Uiso d R 1 . .
    C C6A 0.28522(17) 0.22220(14) -0.05211(13) 0.0531(4) Uani d . 1 . .
    H H6 0.2541 0.2101 -0.1303 0.064 Uiso d R 1 . .
    C C7A 0.18352(14) 0.27264(11) 0.00752(11) 0.0373(3) Uani d . 1 . .
    N N8A 0.04448(12) 0.30270(10) -0.04654(8) 0.0408(3) Uani d . 1 . .
    C C9A -0.04640(14) 0.35099(11) 0.01354(11) 0.0368(3) Uani d . 1 . .
    C C10A -0.19506(16) 0.38402(13) -0.03941(13) 0.0485(4) Uani d . 1 . .
    H H10 -0.2291 0.3720 -0.1174 0.058 Uiso d R 1 . .
    C C11A -0.28754(17) 0.43271(14) 0.01974(15) 0.0581(4) Uani d . 1 . .
    H H11 -0.3885 0.4524 -0.0165 0.070 Uiso d R 1 . .
    C C12A -0.23948(17) 0.45313(15) 0.13443(14) 0.0576(4) Uani d . 1 . .
    H H12 -0.3073 0.4891 0.1743 0.069 Uiso d R 1 . .
    C C13A -0.09857(16) 0.42389(13) 0.18818(12) 0.0481(4) Uani d . 1 . .
    H H13 -0.0669 0.4390 0.2659 0.058 Uiso d R 1 . .
    C C14A 0.00251(13) 0.37098(11) 0.12967(10) 0.0358(3) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0369(5) 0.0785(7) 0.0372(5) -0.0142(5) 0.0068(4) -0.0101(5)
    F2 0.0577(6) 0.0756(6) 0.0284(4) -0.0122(4) 0.0015(4) 0.0024(4)
    F3 0.0534(5) 0.0765(6) 0.0422(5) -0.0212(4) 0.0191(4) -0.0020(4)
    C1 0.0313(7) 0.0412(7) 0.0346(7) -0.0011(5) 0.0049(5) -0.0059(5)
    C2 0.0409(7) 0.0412(7) 0.0255(6) 0.0000(5) 0.0045(5) -0.0009(5)
    C3 0.0384(7) 0.0406(7) 0.0342(7) -0.0044(5) 0.0132(5) -0.0017(5)
    N1A 0.0357(6) 0.0462(6) 0.0311(6) -0.0033(5) 0.0043(5) 0.0010(5)
    C2A 0.0353(7) 0.0373(7) 0.0360(7) -0.0033(5) 0.0055(5) 0.0031(5)
    C3A 0.0372(7) 0.0549(9) 0.0472(8) 0.0000(6) 0.0019(6) 0.0035(7)
    C4A 0.0385(8) 0.0637(10) 0.0726(11) 0.0071(7) 0.0094(7) 0.0010(8)
    C5A 0.0496(9) 0.0692(10) 0.0716(12) 0.0052(8) 0.0248(8) -0.0111(8)
    C6A 0.0540(9) 0.0627(9) 0.0457(8) -0.0024(7) 0.0175(7) -0.0102(7)
    C7A 0.0377(7) 0.0382(7) 0.0355(7) -0.0043(5) 0.0069(5) -0.0011(5)
    N8A 0.0429(6) 0.0451(6) 0.0321(6) -0.0031(5) 0.0030(5) -0.0032(5)
    C9A 0.0357(7) 0.0360(7) 0.0365(7) -0.0033(5) 0.0028(5) 0.0017(5)
    C10A 0.0411(8) 0.0508(8) 0.0470(8) -0.0003(6) -0.0047(6) 0.0004(7)
    C11A 0.0363(8) 0.0612(9) 0.0726(11) 0.0071(7) 0.0024(7) 0.0006(8)
    C12A 0.0455(9) 0.0616(10) 0.0690(11) 0.0063(7) 0.0201(8) -0.0016(8)
    C13A 0.0473(8) 0.0563(8) 0.0426(8) 0.0002(7) 0.0136(6) -0.0027(6)
    C14A 0.0341(7) 0.0371(7) 0.0349(7) -0.0044(5) 0.0050(5) 0.0013(5)
_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
    O1 C1 . 1.3504(15) y
    O1 H1O . 0.8500 ?
    F2 C2 . 1.3528(14) ?
    F3 C3 . 1.3483(14) ?
    C1 C2 . 1.3843(18) ?
    C1 C3 3_666 1.3879(18) ?
    C2 C3 . 1.3740(18) ?
    C3 C1 3_666 1.3879(18) ?
    N1A C2A . 1.3469(16) ?
    N1A C14A . 1.3475(15) ?
    C2A C3A . 1.4248(18) ?
    C2A C7A . 1.4280(17) ?
    C3A C4A . 1.349(2) ?
    C3A H3 . 0.9601 ?
    C4A C5A . 1.413(2) ?
    C4A H4 . 0.9601 ?
    C5A C6A . 1.357(2) ?
    C5A H5 . 0.9600 ?
    C6A C7A . 1.4227(19) ?
    C6A H6 . 0.9601 ?
    C7A N8A . 1.3441(16) ?
    N8A C9A . 1.3425(16) ?
    C9A C10A . 1.4231(18) ?
    C9A C14A . 1.4309(18) ?
    C10A C11A . 1.347(2) ?
    C10A H10 . 0.9600 ?
    C11A C12A . 1.414(2) ?
    C11A H11 . 0.9601 ?
    C12A C13A . 1.355(2) ?
    C12A H12 . 0.9600 ?
    C13A C14A . 1.4202(18) ?
    C13A H13 . 0.9601 ?
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
    C1 O1 H1O . . 113.1 ?
    O1 C1 C2 . . 125.05(12) y
    O1 C1 C3 . 3_666 119.19(11) y
    C2 C1 C3 . 3_666 115.76(12) y
    F2 C2 C3 . . 118.73(11) ?
    F2 C2 C1 . . 119.03(11) ?
    C3 C2 C1 . . 122.23(12) ?
    F3 C3 C2 . . 118.81(11) ?
    F3 C3 C1 . 3_666 119.18(11) ?
    C2 C3 C1 . 3_666 122.00(11) ?
    C2A N1A C14A . . 117.46(11) ?
    N1A C2A C3A . . 119.76(12) ?
    N1A C2A C7A . . 121.04(11) ?
    C3A C2A C7A . . 119.20(12) ?
    C4A C3A C2A . . 119.74(14) ?
    C4A C3A H3 . . 120.6 ?
    C2A C3A H3 . . 119.7 ?
    C3A C4A C5A . . 121.51(14) ?
    C3A C4A H4 . . 119.1 ?
    C5A C4A H4 . . 119.4 ?
    C6A C5A C4A . . 120.52(14) ?
    C6A C5A H5 . . 119.7 ?
    C4A C5A H5 . . 119.8 ?
    C5A C6A C7A . . 120.25(14) ?
    C5A C6A H6 . . 119.9 ?
    C7A C6A H6 . . 119.8 ?
    N8A C7A C6A . . 119.45(12) ?
    N8A C7A C2A . . 121.79(11) ?
    C6A C7A C2A . . 118.76(12) ?
    C9A N8A C7A . . 116.98(11) ?
    N8A C9A C10A . . 119.35(12) ?
    N8A C9A C14A . . 121.73(11) ?
    C10A C9A C14A . . 118.92(12) ?
    C11A C10A C9A . . 120.05(14) ?
    C11A C10A H10 . . 120.1 ?
    C9A C10A H10 . . 119.9 ?
    C10A C11A C12A . . 121.22(14) ?
    C10A C11A H11 . . 119.3 ?
    C12A C11A H11 . . 119.5 ?
    C13A C12A C11A . . 120.78(14) ?
    C13A C12A H12 . . 119.8 ?
    C11A C12A H12 . . 119.4 ?
    C12A C13A C14A . . 120.10(13) ?
    C12A C13A H13 . . 120.0 ?
    C14A C13A H13 . . 119.9 ?
    N1A C14A C13A . . 120.09(12) ?
    N1A C14A C9A . . 120.99(11) ?
    C13A C14A C9A . . 118.92(12) ?
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
    O1 H1O N1A . 0.85 1.89 2.7257(14) 166
    C3A H3 N8A 4_666 0.96 2.60 3.4958(18) 155
    C5A H5 O1 4_665 0.96 2.48 3.4203(18) 165
    C4A H4 F3 2_645 0.96 2.53 3.3445(17) 143
data_global
_journal_date_recd_electronic     2010-05-27
_journal_date_accepted     2010-06-07
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2010
_journal_volume     66
_journal_issue      7
_journal_page_first     o356
_journal_page_last     o360
_journal_paper_category     FO
_journal_coeditor_code     SU3047
_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
;
Cocrystals of 2,3,5,6-tetrafluorobenzene-1,4-diol with diaza aromatic compounds
;
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
;
