#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/20/2222025.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_2222025
loop_
_publ_author_name
'Cui, Ping'
'Shi, Lei'
_publ_section_title
;
 4-Fluoro-2-[(E)-2-pyridyliminomethyl]phenol
;
_journal_coeditor_code           HB2968
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1282
_journal_paper_doi               10.1107/S1600536809017280
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H9 F N2 O'
_chemical_formula_moiety         'C12 H9 F N2 O'
_chemical_formula_sum            'C12 H9 F N2 O'
_chemical_formula_weight         216.21
_chemical_name_systematic
;
4-Fluoro-2-[(E)-2-pyridyliminomethyl]phenol
;
_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                 113.33(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1635(11)
_cell_length_b                   6.2252(6)
_cell_length_c                   13.8235(17)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1040.2(3)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0636
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            1907
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.168
_refine_ls_extinction_coef       0.089(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1825
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0534
_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)+(0.0657P)²+0.1652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1445
_reflns_number_gt                1210
_reflns_number_total             1825
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2968.cif
_cod_data_source_block           I
_cod_original_cell_volume        1040.1(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2222025
_cod_database_fobs_code          2222025
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_disorder_assembly
_atom_site_disorder_group
C C1 0.96836(16) 0.2734(3) 0.23488(17) 0.0457(6) Uani d . 1 . .
C C2 1.06679(18) 0.2492(4) 0.21918(18) 0.0529(6) Uani d . 1 . .
C C3 1.1349(2) 0.0730(4) 0.2622(2) 0.0633(7) Uani d . 1 . .
H H3 1.1996 0.0568 0.2510 0.076 Uiso calc R 1 . .
C C4 1.1080(2) -0.0767(4) 0.3207(2) 0.0658(7) Uani d . 1 . .
H H4 1.1540 -0.1936 0.3496 0.079 Uiso calc R 1 . .
C C5 1.0116(2) -0.0506(4) 0.3357(2) 0.0619(7) Uani d . 1 . .
C C6 0.94233(19) 0.1189(3) 0.29492(19) 0.0548(6) Uani d . 1 . .
H H6 0.8779 0.1318 0.3069 0.066 Uiso calc R 1 . .
C C7 0.89393(17) 0.4506(3) 0.18913(17) 0.0484(6) Uani d . 1 . .
H H7 0.8301 0.4632 0.2022 0.058 Uiso calc R 1 . .
C C8 0.83993(18) 0.7650(3) 0.08721(17) 0.0488(6) Uani d . 1 . .
C C9 0.8652(2) 0.9050(4) 0.02246(19) 0.0591(7) Uani d . 1 . .
H H9 0.9269 0.8816 0.0070 0.071 Uiso calc R 1 . .
C C10 0.7981(2) 1.0788(4) -0.01873(19) 0.0673(7) Uani d . 1 . .
H H10 0.8141 1.1762 -0.0618 0.081 Uiso calc R 1 . .
C C11 0.7071(2) 1.1067(4) 0.0045(2) 0.0677(7) Uani d . 1 . .
H H11 0.6600 1.2231 -0.0223 0.081 Uiso calc R 1 . .
C C12 0.6870(2) 0.9583(4) 0.0684(2) 0.0660(7) Uani d . 1 . .
H H12 0.6247 0.9772 0.0835 0.079 Uiso calc R 1 . .
F F1 0.98419(14) -0.2003(2) 0.39318(14) 0.0938(6) Uani d . 1 . .
N N1 0.91366(15) 0.5906(3) 0.13106(15) 0.0514(5) Uani d . 1 . .
N N2 0.75169(16) 0.7888(3) 0.11012(15) 0.0582(6) Uani d . 1 . .
O O1 1.09729(14) 0.3937(3) 0.16264(16) 0.0721(6) Uani d . 1 . .
H H1 1.0476 0.4818 0.1364 0.108 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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
C6 C1 C2 . . 118.4(2) ?
C6 C1 C7 . . 120.12(19) ?
C2 C1 C7 . . 121.5(2) ?
O1 C2 C3 . . 118.8(2) ?
O1 C2 C1 . . 121.4(2) ?
C3 C2 C1 . . 119.7(2) ?
C4 C3 C2 . . 121.0(2) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 118.6(2) ?
C3 C4 H4 . . 120.7 ?
C5 C4 H4 . . 120.7 ?
C6 C5 F1 . . 118.9(2) ?
C6 C5 C4 . . 122.4(2) ?
F1 C5 C4 . . 118.8(2) ?
C5 C6 C1 . . 119.8(2) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
N1 C7 C1 . . 121.6(2) ?
N1 C7 H7 . . 119.2 ?
C1 C7 H7 . . 119.2 ?
N2 C8 C9 . . 122.8(2) ?
N2 C8 N1 . . 119.8(2) ?
C9 C8 N1 . . 117.3(2) ?
C10 C9 C8 . . 119.1(2) ?
C10 C9 H9 . . 120.4 ?
C8 C9 H9 . . 120.4 ?
C11 C10 C9 . . 118.9(2) ?
C11 C10 H10 . . 120.6 ?
C9 C10 H10 . . 120.6 ?
C10 C11 C12 . . 118.4(2) ?
C10 C11 H11 . . 120.8 ?
C12 C11 H11 . . 120.8 ?
N2 C12 C11 . . 123.8(2) ?
N2 C12 H12 . . 118.1 ?
C11 C12 H12 . . 118.1 ?
C7 N1 C8 . . 120.91(19) ?
C8 N2 C12 . . 117.0(2) ?
C2 O1 H1 . . 109.5 ?
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
C1 C6 . 1.399(3) ?
C1 C2 . 1.404(3) ?
C1 C7 . 1.444(3) ?
C2 O1 . 1.353(3) ?
C2 C3 . 1.392(3) ?
C3 C4 . 1.369(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.375(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.362(3) ?
C5 F1 . 1.363(3) ?
C6 H6 . 0.9300 ?
C7 N1 . 1.279(3) ?
C7 H7 . 0.9300 ?
C8 N2 . 1.328(3) ?
C8 C9 . 1.381(3) ?
C8 N1 . 1.422(3) ?
C9 C10 . 1.370(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.368(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.375(3) ?
C11 H11 . 0.9300 ?
C12 N2 . 1.335(3) ?
C12 H12 . 0.9300 ?
O1 H1 . 0.8200 ?
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 H1 N1 . 0.82 1.86 2.588(2) 147
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 O1 . . . . -179.5(2) ?
C7 C1 C2 O1 . . . . 1.6(3) ?
C6 C1 C2 C3 . . . . 0.7(3) ?
C7 C1 C2 C3 . . . . -178.2(2) ?
O1 C2 C3 C4 . . . . 179.5(2) ?
C1 C2 C3 C4 . . . . -0.6(3) ?
C2 C3 C4 C5 . . . . 0.4(4) ?
C3 C4 C5 C6 . . . . -0.2(4) ?
C3 C4 C5 F1 . . . . 179.5(2) ?
F1 C5 C6 C1 . . . . -179.4(2) ?
C4 C5 C6 C1 . . . . 0.3(4) ?
C2 C1 C6 C5 . . . . -0.5(3) ?
C7 C1 C6 C5 . . . . 178.4(2) ?
C6 C1 C7 N1 . . . . -177.70(19) ?
C2 C1 C7 N1 . . . . 1.2(3) ?
N2 C8 C9 C10 . . . . 1.3(3) ?
N1 C8 C9 C10 . . . . -178.0(2) ?
C8 C9 C10 C11 . . . . -0.9(4) ?
C9 C10 C11 C12 . . . . 0.0(4) ?
C10 C11 C12 N2 . . . . 0.6(4) ?
C1 C7 N1 C8 . . . . -179.53(19) ?
N2 C8 N1 C7 . . . . 2.8(3) ?
C9 C8 N1 C7 . . . . -177.8(2) ?
C9 C8 N2 C12 . . . . -0.8(3) ?
N1 C8 N2 C12 . . . . 178.5(2) ?
C11 C12 N2 C8 . . . . -0.2(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742358
