#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/82/2018229.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_2018229
loop_
_publ_author_name
'Czapik, Agnieszka'
'Gdaniec, Maria'
_publ_section_title
;
 5:1 and 2:1 cocrystals of 2,3,4,5,6-pentafluorophenol with phenazine
;
_journal_coeditor_code           SU3067
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o341
_journal_page_last               o345
_journal_paper_doi               10.1107/S0108270111027843
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '2C6 H F5 O , C12 H8 N2'
_chemical_formula_moiety         '2(C6 H F5 O), C12 H8 N2'
_chemical_formula_sum            'C24 H10 F10 N2 O2'
_chemical_formula_weight         548.34
_chemical_name_systematic
;
2,3,4,5,6-pentafluorophenol--phenazine (2/1)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.931(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.9045(3)
_cell_length_b                   17.1342(10)
_cell_length_c                   12.6397(6)
_cell_measurement_reflns_used    766
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      36.68
_cell_measurement_theta_min      3.50
_cell_volume                     1062.03(10)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Oxford SuperNova'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova Cu X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10876
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         76.43
_diffrn_reflns_theta_min         4.35
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.525
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.292
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0693P)²+0.4475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                1939
_reflns_number_total             2186
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su3067.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2018229
_cod_database_fobs_code          2018229
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'
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
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
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'
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
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_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
