#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/27/2212758.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_2212758
loop_
_publ_author_name
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
'Narayana, B.'
'Vijesh, A. M.'
'Yathirajan, H. S.'
_publ_section_title
;
 (E)-2-Hydroxy-5-methyl-3-[(2-pyridylimino)methyl]benzaldehyde
;
_journal_coeditor_code           AT2241
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1916
_journal_page_last               o1918
_journal_paper_doi               10.1107/S1600536807012913
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H12 N2 O2'
_chemical_formula_moiety         'C14 H12 N2 O2'
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.26
_chemical_melting_point          .393E-305
_chemical_name_common
3-(2-pyridyliminomethyl)-5-methylsalicylaldehyde
_chemical_name_systematic
;
(E)-2-Hydroxy-5-methyl-3-[(2-pyridylimino)methyl]benzaldehyde
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 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                 108.847(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.4049(8)
_cell_length_b                   4.2957(3)
_cell_length_c                   20.154(2)
_cell_measurement_reflns_used    10246
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      2.14
_cell_volume                     606.71(10)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDSII'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10246
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'prismatic rod'
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.156
_refine_ls_extinction_coef       0.064(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1184
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0430
_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)+(0.07P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                853
_reflns_number_total             1184
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2241.cif
_cod_data_source_block           I
_cod_original_cell_volume        606.72(10)
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2212758
_cod_database_fobs_code          2212758
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, 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
C C1 0.1508(4) 0.9603(7) 0.77188(17) 0.0589(8) Uani d . 1
C C2 0.3194(4) 1.0599(7) 0.75990(17) 0.0608(8) Uani d . 1
C C3 0.4422(4) 1.2641(8) 0.80672(17) 0.0634(9) Uani d . 1
C C4 0.3982(4) 1.3660(7) 0.86578(19) 0.0626(8) Uani d . 1
H H4 0.4812 1.5023 0.8969 0.075 Uiso calc R 1
C C5 0.2348(4) 1.2696(7) 0.87913(18) 0.0620(8) Uani d . 1
C C6 0.1144(4) 1.0688(8) 0.83129(16) 0.0626(8) Uani d . 1
H H6 0.0035 1.0032 0.8393 0.075 Uiso calc R 1
C C7 0.6152(5) 1.3830(9) 0.7946(2) 0.0773(10) Uani d . 1
H H7 0.6398 1.3166 0.7545 0.093 Uiso calc R 1
C C8 0.1889(6) 1.3835(9) 0.9425(2) 0.0783(10) Uani d . 1
H H8A 0.0709 1.2929 0.9430 0.117 Uiso calc R 1
H H8B 0.1772 1.6062 0.9407 0.117 Uiso calc R 1
H H8C 0.2894 1.3241 0.9842 0.117 Uiso calc R 1
C C9 0.0206(4) 0.7485(8) 0.72540(18) 0.0621(7) Uani d . 1
H H9 -0.0883 0.6872 0.7354 0.075 Uiso calc R 1
C C10 -0.0854(5) 0.4396(7) 0.62400(18) 0.0630(8) Uani d . 1
C C11 -0.0538(5) 0.3529(8) 0.5637(2) 0.0758(10) Uani d . 1
H H11 0.0548 0.4196 0.5543 0.091 Uiso calc R 1
C C12 -0.1847(6) 0.1655(9) 0.5171(2) 0.0847(11) Uani d . 1
H H12 -0.1668 0.1045 0.4754 0.102 Uiso calc R 1
C C13 -0.3424(6) 0.0696(9) 0.5330(2) 0.0841(11) Uani d . 1
H H13 -0.4344 -0.0558 0.5023 0.101 Uiso calc R 1
C C14 -0.3604(6) 0.1640(9) 0.5955(2) 0.0844(11) Uani d . 1
H H14 -0.4660 0.0952 0.6067 0.101 Uiso calc R 1
N N1 0.0498(4) 0.6410(7) 0.67039(15) 0.0644(7) Uani d . 1
N N2 -0.2356(4) 0.3489(6) 0.64126(16) 0.0738(8) Uani d . 1
O O1 0.3616(3) 0.9620(6) 0.70300(13) 0.0784(7) Uani d . 1
H H1 0.2778 0.8437 0.6800 0.118 Uiso calc R 1
O O2 0.7275(3) 1.5603(7) 0.83302(16) 0.0938(9) Uani d . 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_publ_flag
C6 C1 C2 118.3(3) ?
C6 C1 C9 119.9(3) ?
C2 C1 C9 121.8(3) ?
O1 C2 C3 119.6(3) ?
O1 C2 C1 120.7(3) ?
C3 C2 C1 119.7(3) ?
C2 C3 C4 119.6(3) ?
C2 C3 C7 121.4(3) ?
C4 C3 C7 119.1(3) ?
C5 C4 C3 121.9(3) ?
C5 C4 H4 119.0 ?
C3 C4 H4 119.0 ?
C6 C5 C4 117.3(3) ?
C6 C5 C8 121.5(3) ?
C4 C5 C8 121.2(3) ?
C5 C6 C1 123.3(3) ?
C5 C6 H6 118.4 ?
C1 C6 H6 118.4 ?
O2 C7 C3 124.8(4) ?
O2 C7 H7 117.6 ?
C3 C7 H7 117.6 ?
C5 C8 H8A 109.5 ?
C5 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C5 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
N1 C9 C1 121.9(3) y
N1 C9 H9 119.1 ?
C1 C9 H9 119.1 ?
N2 C10 C11 123.7(3) ?
N2 C10 N1 118.6(3) ?
C11 C10 N1 117.8(3) ?
C10 C11 C12 119.0(3) ?
C10 C11 H11 120.5 ?
C12 C11 H11 120.5 ?
C13 C12 C11 118.9(4) ?
C13 C12 H12 120.5 ?
C11 C12 H12 120.5 ?
C14 C13 C12 118.0(4) ?
C14 C13 H13 121.0 ?
C12 C13 H13 121.0 ?
N2 C14 C13 124.1(4) ?
N2 C14 H14 118.0 ?
C13 C14 H14 118.0 ?
C9 N1 C10 120.5(3) y
C10 N2 C14 116.4(3) ?
C2 O1 H1 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.390(4) ?
C1 C2 1.412(4) ?
C1 C9 1.432(5) y
C2 O1 1.349(4) y
C2 C3 1.390(4) ?
C3 C4 1.402(4) ?
C3 C7 1.471(4) ?
C4 C5 1.385(4) ?
C4 H4 0.9300 ?
C5 C6 1.383(5) ?
C5 C8 1.506(5) ?
C6 H6 0.9300 ?
C7 O2 1.206(4) ?
C7 H7 0.9300 ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
C9 N1 1.282(4) y
C9 H9 0.9300 ?
C10 N2 1.326(4) ?
C10 C11 1.362(5) ?
C10 N1 1.422(4) y
C11 C12 1.372(5) ?
C11 H11 0.9300 ?
C12 C13 1.370(6) ?
C12 H12 0.9300 ?
C13 C14 1.369(6) ?
C13 H13 0.9300 ?
C14 N2 1.336(5) ?
C14 H14 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 1.85 2.585(3) 147.9
C9 H9 O2 1_445 0.93 2.79 3.620(4) 149.9
C14 H14 O1 1_445 0.93 2.71 3.546(5) 150.5
C6 H6 O2 1_445 0.93 2.77 3.612(4) 151.8
C7 H7 N2 1_665 0.93 2.73 3.606(5) 158.0
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_publ_flag
C6 C1 C2 O1 -179.9(3) ?
C9 C1 C2 O1 1.2(4) ?
C6 C1 C2 C3 -0.7(4) ?
C9 C1 C2 C3 -179.6(3) ?
O1 C2 C3 C4 179.9(3) ?
C1 C2 C3 C4 0.7(5) ?
O1 C2 C3 C7 1.6(5) ?
C1 C2 C3 C7 -177.6(3) ?
C2 C3 C4 C5 -0.1(5) ?
C7 C3 C4 C5 178.2(3) ?
C3 C4 C5 C6 -0.5(4) ?
C3 C4 C5 C8 -179.5(3) ?
C4 C5 C6 C1 0.5(5) ?
C8 C5 C6 C1 179.5(3) ?
C2 C1 C6 C5 0.1(4) ?
C9 C1 C6 C5 179.0(3) ?
C2 C3 C7 O2 180.0(3) ?
C4 C3 C7 O2 1.7(6) ?
C6 C1 C9 N1 -179.4(3) ?
C2 C1 C9 N1 -0.6(5) ?
N2 C10 C11 C12 1.1(5) ?
N1 C10 C11 C12 -178.3(3) ?
C10 C11 C12 C13 -0.5(5) ?
C11 C12 C13 C14 -0.6(6) ?
C12 C13 C14 N2 1.4(6) ?
C1 C9 N1 C10 -177.8(3) y
N2 C10 N1 C9 -4.5(4) ?
C11 C10 N1 C9 174.9(3) ?
C11 C10 N2 C14 -0.5(5) ?
N1 C10 N2 C14 178.9(3) ?
C13 C14 N2 C10 -0.8(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655191
