#------------------------------------------------------------------------------
#$Date: 2019-09-18 13:52:27 +0300 (Wed, 18 Sep 2019) $
#$Revision: 218432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/55/7215586.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_7215586
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Salmon, Debra J.'
'Smith, Michelle M.'
'Desper, John'
_publ_section_title
;
 Cyanooximes as effective and selective co-crystallizing agents
;
_journal_coden_ASTM              CRECF4
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              439
_journal_page_last               443
_journal_paper_doi               10.1039/b811322j
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety
;
(C8 H5 N2 O F)2 (C12 H10 N2)
;
_chemical_formula_sum            'C28 H20 F2 N6 O2'
_chemical_formula_weight         510.50
_chemical_name_common
'(2-fluoro-PhC(CN)(=NOH))2, 1,2-di(4-pyridyl)ethene'
_chemical_name_systematic
;
[2-fluoro-PhC(CN)(=NOH)]2, 1,2-di(4-pyridyl)ethene
;
_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                98.884(10)
_cell_angle_beta                 93.147(11)
_cell_angle_gamma                94.624(10)
_cell_formula_units_Z            1
_cell_length_a                   3.8189(6)
_cell_length_b                   11.2941(18)
_cell_length_c                   14.107(2)
_cell_measurement_reflns_used    783
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.70
_cell_measurement_theta_min      2.90
_cell_volume                     597.79(16)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1106
_diffrn_reflns_av_sigmaI/netI    0.0972
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4295
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0597
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1754
_reflns_number_gt                1734
_reflns_number_total             2606
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7200258
_cod_data_source_file            b811322j.txt
_cod_data_source_block           B5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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 

 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-18

 Marked entry as a duplicate of entry 7200258.

 Antanas Vaitkus,
 2019-09-18
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7215586
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.9413(5) 0.26002(18) 0.58790(14) 0.0299(5) Uani 1 1 d . . .
C12A C 1.1167(5) 0.3527(2) 0.55049(16) 0.0365(5) Uani 0.669(2) 1 d P A 1
F12 F 1.2186(6) 0.45468(18) 0.60662(15) 0.0501(5) Uani 0.669(2) 1 d P A 1
C12B C 1.1167(5) 0.3527(2) 0.55049(16) 0.0365(5) Uani 0.331(2) 1 d P A 2
H12 H 1.1889 0.4261 0.5921 0.044 Uiso 0.331(2) 1 calc PR A 2
C13 C 1.1896(6) 0.3426(2) 0.45607(17) 0.0442(6) Uani 1 1 d . . .
H13 H 1.3081 0.4083 0.4326 0.053 Uiso 1 1 calc R A 1
C14 C 1.0892(6) 0.2360(3) 0.39513(17) 0.0478(6) Uani 1 1 d . A .
H14 H 1.1426 0.2277 0.3296 0.057 Uiso 1 1 calc R . .
C15 C 0.9126(6) 0.1416(2) 0.42864(16) 0.0453(6) Uani 1 1 d . . .
H15 H 0.8397 0.0687 0.3865 0.054 Uiso 1 1 calc R A 1
C16A C 0.8432(5) 0.1545(2) 0.52396(16) 0.0378(5) Uani 0.669(2) 1 d P A 1
H16 H 0.7236 0.0888 0.5471 0.045 Uiso 0.669(2) 1 calc PR A 1
C16B C 0.8432(5) 0.1545(2) 0.52396(16) 0.0378(5) Uani 0.331(2) 1 d P A 2
F16 F 0.6496(11) 0.0710(4) 0.5501(3) 0.0501(5) Uani 0.331(2) 1 d P A 2
C17 C 0.8569(5) 0.27048(18) 0.68908(14) 0.0315(5) Uani 1 1 d . A .
N17 N 0.8017(4) 0.37374(17) 0.73653(12) 0.0365(5) Uani 1 1 d . . .
O17 O 0.7233(4) 0.36743(16) 0.82888(11) 0.0442(4) Uani 1 1 d . A .
H17 H 0.675(7) 0.455(3) 0.851(2) 0.066(9) Uiso 1 1 d . . .
C18 C 0.8337(6) 0.1630(2) 0.73340(16) 0.0428(6) Uani 1 1 d . . .
N18 N 0.8214(8) 0.0771(2) 0.76621(17) 0.0707(8) Uani 1 1 d . A .
N21 N 0.6016(5) 0.59158(17) 0.88855(13) 0.0390(5) Uani 1 1 d . . .
C22 C 0.4607(6) 0.6538(2) 0.82510(16) 0.0424(6) Uani 1 1 d . . .
H22 H 0.3870 0.6126 0.7624 0.051 Uiso 1 1 calc R . .
C23 C 0.4173(6) 0.7738(2) 0.84592(15) 0.0387(5) Uani 1 1 d . . .
H23 H 0.3183 0.8137 0.7977 0.046 Uiso 1 1 calc R . .
C24 C 0.5165(5) 0.83774(19) 0.93681(14) 0.0314(5) Uani 1 1 d . . .
C25 C 0.6635(5) 0.7723(2) 1.00309(15) 0.0358(5) Uani 1 1 d . . .
H25 H 0.7371 0.8109 1.0666 0.043 Uiso 1 1 calc R . .
C26 C 0.7011(6) 0.6522(2) 0.97607(15) 0.0363(5) Uani 1 1 d . . .
H26 H 0.8036 0.6098 1.0222 0.044 Uiso 1 1 calc R . .
C27 C 0.4593(5) 0.96438(19) 0.95824(15) 0.0337(5) Uani 1 1 d . . .
H27 H 0.3542 0.9993 0.9079 0.040 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
C12A C11 C16A 116.4(2) .
C12A C11 C17 122.95(18) .
C16A C11 C17 120.66(19) .
F12 C12A C13 117.7(2) .
F12 C12A C11 119.8(2) .
C13 C12A C11 122.5(2) .
C12A C13 C14 119.2(2) .
C12A C13 H13 120.4 .
C14 C13 H13 120.4 .
C15 C14 C13 120.5(2) .
C15 C14 H14 119.8 .
C13 C14 H14 119.8 .
C16A C15 C14 118.9(2) .
C16A C15 H15 120.5 .
C14 C15 H15 120.5 .
C15 C16A C11 122.5(2) .
C15 C16A H16 118.8 .
C11 C16A H16 118.8 .
N17 C17 C18 121.17(19) .
N17 C17 C11 120.14(19) .
C18 C17 C11 118.69(18) .
C17 N17 O17 112.64(18) .
N17 O17 H17 99.6(16) .
N18 C18 C17 178.0(3) .
C26 N21 C22 116.81(19) .
N21 C22 C23 123.3(2) .
N21 C22 H22 118.4 .
C23 C22 H22 118.4 .
C22 C23 C24 120.6(2) .
C22 C23 H23 119.7 .
C24 C23 H23 119.7 .
C23 C24 C25 116.0(2) .
C23 C24 C27 119.74(19) .
C25 C24 C27 124.27(19) .
C26 C25 C24 119.76(19) .
C26 C25 H25 120.1 .
C24 C25 H25 120.1 .
N21 C26 C25 123.6(2) .
N21 C26 H26 118.2 .
C25 C26 H26 118.2 .
C27 C27 C24 125.9(3) 2_677
C27 C27 H27 117.1 2_677
C24 C27 H27 117.1 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C11 C12A 1.385(3) .
C11 C16A 1.391(3) .
C11 C17 1.470(3) .
C12A F12 1.310(3) .
C12A C13 1.365(3) .
C13 C14 1.381(4) .
C13 H13 0.9500 .
C14 C15 1.374(4) .
C14 H14 0.9500 .
C15 C16A 1.373(3) .
C15 H15 0.9500 .
C16A H16 0.9500 .
C17 N17 1.291(3) .
C17 C18 1.447(3) .
N17 O17 1.364(2) .
O17 H17 1.03(3) .
C18 N18 1.136(3) .
N21 C26 1.335(3) .
N21 C22 1.337(3) .
C22 C23 1.367(3) .
C22 H22 0.9500 .
C23 C24 1.388(3) .
C23 H23 0.9500 .
C24 C25 1.399(3) .
C24 C27 1.452(3) .
C25 C26 1.373(3) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C27 C27 1.326(4) 2_677
C27 H27 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O17 H17 N21 1.03(3) 1.60(3) 2.628(3) 178(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C16A C11 C12A F12 -179.7(2) .
C17 C11 C12A F12 0.9(3) .
C16A C11 C12A C13 0.3(3) .
C17 C11 C12A C13 -179.09(19) .
F12 C12A C13 C14 179.3(2) .
C11 C12A C13 C14 -0.7(3) .
C12A C13 C14 C15 1.1(3) .
C13 C14 C15 C16A -1.1(4) .
C14 C15 C16A C11 0.8(3) .
C12A C11 C16A C15 -0.4(3) .
C17 C11 C16A C15 179.1(2) .
C12A C11 C17 N17 29.8(3) .
C16A C11 C17 N17 -149.6(2) .
C12A C11 C17 C18 -150.8(2) .
C16A C11 C17 C18 29.8(3) .
C18 C17 N17 O17 0.0(3) .
C11 C17 N17 O17 179.37(16) .
C26 N21 C22 C23 0.2(3) .
N21 C22 C23 C24 -0.8(4) .
C22 C23 C24 C25 0.7(3) .
C22 C23 C24 C27 -178.3(2) .
C23 C24 C25 C26 -0.1(3) .
C27 C24 C25 C26 178.9(2) .
C22 N21 C26 C25 0.5(3) .
C24 C25 C26 N21 -0.5(3) .
C23 C24 C27 C27 179.8(3) 2_677
C25 C24 C27 C27 0.9(4) 2_677
