#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/77/2017731.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_2017731
loop_
_publ_author_name
'Czapik, Agnieszka'
'Gdaniec, Maria'
_publ_section_title
;
 Cocrystals of 2,3,5,6-tetrafluorobenzene-1,4-diol with diaza aromatic
 compounds
;
_journal_coeditor_code           SU3047
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o356
_journal_page_last               o360
_journal_paper_doi               10.1107/S0108270110021736
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H2 F4 O2 , C4 H4 N2'
_chemical_formula_moiety         'C6 H2 F4 O2 , C4 H4 N2'
_chemical_formula_sum            'C10 H6 F4 N2 O2'
_chemical_formula_weight         262.17
_chemical_melting_point_gt       444
_chemical_melting_point_lt       446
_chemical_name_systematic
;
pyrazine--2,3,5,6-tetrafluorobenzene-1,4-diol (1/1)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                88.14(2)
_cell_angle_beta                 85.67(2)
_cell_angle_gamma                77.41(2)
_cell_formula_units_Z            1
_cell_length_a                   3.6671(10)
_cell_length_b                   7.585(2)
_cell_length_c                   9.582(2)
_cell_measurement_reflns_used    1281
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      4
_cell_volume                     259.34(11)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2004)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2004)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2004)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Kuma KM-4 CCD κ geometry'
_diffrn_measurement_method       ω
_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  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1921
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.51
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             132
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.305
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0482
_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)+(0.0994P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                791
_reflns_number_total             917
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su3047.cif
_cod_data_source_block           I
_cod_database_code               2017731
_cod_database_fobs_code          2017731
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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)
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'
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_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_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
