#------------------------------------------------------------------------------
#$Date: 2023-12-08 16:16:31 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/42/7114297.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_7114297
loop_
_publ_author_name
'Vangala, Venu R.'
'Nangia, Ashwini'
'Lynch, Vincent M.'
_publ_section_title
;
 Interplay of phenyl--perfluorophenyl stacking, C--H⋯F,
 C--F⋯π and F⋯F interactions in some crystalline aromatic
 azinesElectronic supplementary information (ESI) available: experimental
 powder X-ray diffraction spectra. See
 http://www.rsc.org/suppdata/cc/b2/b202181a/
;
_journal_issue                   12
_journal_name_full               'Chemical Communications'
_journal_page_first              1304
_journal_paper_doi               10.1039/b202181a
_journal_year                    2002
_chemical_formula_moiety         'C14 H2 F10 N2 . C14 H12 N2'
_chemical_formula_sum            'C28 H14 F10 N4'
_chemical_formula_weight         596.43
_chemical_melting_point          391
_chemical_name_common
'1:1 Complex of Benzalazine : bis(Pentafluorophenylmethylidenehydrazone)'
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.052(2)
_cell_angle_beta                 93.590(2)
_cell_angle_gamma                113.3100(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2820(2)
_cell_length_b                   7.9073(2)
_cell_length_c                   11.9305(4)
_cell_measurement_reflns_used    2210
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     627.37(3)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection
'Collect data collection software, Nonius 1998.'
_computing_data_reduction        SCALEPACK
_computing_molecular_graphics    'ORTEP and PLUTON'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal focus for the X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4453
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        'less than 1'
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.9854
_exptl_absorpt_correction_T_min  0.9544
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0526
_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)+(0.0362P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                1819
_reflns_number_total             2836
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b202181a.txt
_cod_data_source_block           compound4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '391K' was changed to '391' - the
value should be numeric and without a unit
designator.

'_symmetry_cell_setting' value 'Triclinic' changed to
'triclinic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

data name '_atom_site_symmetry_multiplicit' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C14 H2 F10 N2 . C14 H12 N2'
_cod_database_code               7114297
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
F1 F 0.6085(2) 0.5480(2) 0.39763(12) 0.0421(4) Uani 1 1 d
F2 F 0.3051(2) 0.4290(3) 0.02804(13) 0.0491(5) Uani 1 1 d
F4 F 0.3057(3) -0.0637(2) 0.22549(13) 0.0479(5) Uani 1 1 d
F6 F 0.5132(3) 0.6723(2) 0.20745(14) 0.0507(5) Uani 1 1 d
F9 F 0.2103(3) 0.0632(3) 0.03926(13) 0.0565(5) Uani 1 1 d
N3 N 0.4668(3) 0.0086(3) 0.44437(16) 0.0297(5) Uani 1 1 d
C8 C 0.3591(4) 0.1194(3) 0.2262(2) 0.0295(5) Uani 1 1 d
C11 C 0.5081(4) 0.4235(3) 0.31046(19) 0.0287(5) Uani 1 1 d
C13 C 0.4587(3) 0.2368(3) 0.32116(18) 0.0252(5) Uani 1 1 d
C14 C 0.4603(4) 0.4898(3) 0.2136(2) 0.0324(6) Uani 1 1 d
C15 C 0.5111(4) 0.1781(3) 0.42872(19) 0.0269(5) Uani 1 1 d
H15A H 0.586(4) 0.278(4) 0.486(2) 0.032 Uiso 1 1 d
C19 C 0.3583(4) 0.3683(4) 0.1226(2) 0.0346(6) Uani 1 1 d
C21 C 0.3089(4) 0.1829(4) 0.1287(2) 0.0350(6) Uani 1 1 d
N5 N 1.0137(3) 0.0842(3) 0.47705(17) 0.0331(5) Uani 1 1 d
C7 C 0.8666(4) 0.3286(4) 0.1394(2) 0.0348(6) Uani 1 1 d
H7A H 0.808(4) 0.305(4) 0.060(2) 0.042 Uiso 1 1 d
C10 C 0.9552(4) 0.5074(4) 0.1895(2) 0.0361(6) Uani 1 1 d
H10A H 0.959(4) 0.609(4) 0.145(2) 0.043 Uiso 1 1 d
C12 C 0.9393(4) 0.2136(3) 0.31309(19) 0.0281(5) Uani 1 1 d
C16 C 1.0286(4) 0.3948(4) 0.3624(2) 0.0305(6) Uani 1 1 d
H16A H 1.088(4) 0.415(4) 0.439(2) 0.037 Uiso 1 1 d
C17 C 1.0355(4) 0.5407(4) 0.3009(2) 0.0357(6) Uani 1 1 d
H17A H 1.099(4) 0.664(4) 0.337(2) 0.043 Uiso 1 1 d
C18 C 0.9301(4) 0.0576(3) 0.3763(2) 0.0299(6) Uani 1 1 d
H18A H 0.854(4) -0.072(4) 0.340(2) 0.036 Uiso 1 1 d
C20 C 0.8570(4) 0.1814(4) 0.2007(2) 0.0315(6) Uani 1 1 d
H20A H 0.798(4) 0.061(4) 0.169(2) 0.038 Uiso 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'
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_3
C15 N3 N3 110.4(2) 2_656
F4 C8 C21 116.6(2) .
F4 C8 C13 121.1(2) .
C21 C8 C13 122.3(2) .
F1 C11 C14 117.3(2) .
F1 C11 C13 119.6(2) .
C14 C11 C13 123.1(2) .
C8 C13 C11 115.5(2) .
C8 C13 C15 125.2(2) .
C11 C13 C15 119.3(2) .
F6 C14 C19 120.0(2) .
F6 C14 C11 120.6(2) .
C19 C14 C11 119.4(2) .
N3 C15 C13 122.3(2) .
N3 C15 H15A 122.4(15) .
C13 C15 H15A 115.3(15) .
F2 C19 C14 120.6(2) .
F2 C19 C21 119.8(2) .
C14 C19 C21 119.6(2) .
F9 C21 C19 119.8(2) .
F9 C21 C8 120.1(2) .
C19 C21 C8 120.1(2) .
C18 N5 N5 111.7(3) 2_756
C10 C7 C20 120.1(2) .
C10 C7 H7A 119.8(16) .
C20 C7 H7A 120.1(16) .
C7 C10 C17 120.2(2) .
C7 C10 H10A 118.9(17) .
C17 C10 H10A 120.9(17) .
C16 C12 C20 119.1(2) .
C16 C12 C18 121.3(2) .
C20 C12 C18 119.6(2) .
C17 C16 C12 120.3(2) .
C17 C16 H16A 121.5(16) .
C12 C16 H16A 118.2(16) .
C10 C17 C16 120.1(3) .
C10 C17 H17A 121.4(17) .
C16 C17 H17A 118.5(17) .
N5 C18 C12 120.7(2) .
N5 C18 H18A 120.2(15) .
C12 C18 H18A 119.0(15) .
C7 C20 C12 120.1(3) .
C7 C20 H20A 121.5(17) .
C12 C20 H20A 118.3(17) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C11 1.346(3) .
F2 C19 1.343(3) .
F4 C8 1.342(3) .
F6 C14 1.345(3) .
F9 C21 1.344(3) .
N3 C15 1.276(3) .
N3 N3 1.416(4) 2_656
C8 C21 1.376(3) .
C8 C13 1.387(3) .
C11 C14 1.375(3) .
C11 C13 1.390(3) .
C13 C15 1.466(3) .
C14 C19 1.369(4) .
C15 H15A 0.98(3) .
C19 C21 1.372(4) .
N5 C18 1.281(3) .
N5 N5 1.412(4) 2_756
C7 C10 1.383(4) .
C7 C20 1.388(4) .
C7 H7A 1.00(3) .
C10 C17 1.386(4) .
C10 H10A 0.97(3) .
C12 C16 1.395(4) .
C12 C20 1.401(3) .
C12 C18 1.461(3) .
C16 C17 1.387(3) .
C16 H16A 0.96(3) .
C17 H17A 0.96(3) .
C18 H18A 1.01(3) .
C20 H20A 0.93(3) .
