#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/30/2213026.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_2213026
loop_
_publ_author_name
'Büyükgüngör, Orhan'
'Odabaşoğlu, Mustafa'
'Narayana, B.'
'Vijesh, A. M.'
'Yathirajan, H. S.'
_publ_section_title
(E)-2-Hydroxy-5-methyl-3-[(4-methyl-2-pyridyl)iminomethyl]benzaldehyde
_journal_coeditor_code           SJ2259
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1996
_journal_page_last               o1998
_journal_paper_doi               10.1107/S1600536807013177
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H14 N2 O2'
_chemical_formula_moiety         'C15 H14 N2 O2'
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28
_chemical_name_systematic
;
(E)-2-Hydroxy-5-methyl-3-[(4-methyl-2-pyridyl)iminomethyl]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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.273(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.4936(7)
_cell_length_b                   4.5019(3)
_cell_length_c                   20.677(2)
_cell_measurement_reflns_used    10340
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.09
_cell_volume                     658.45(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, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS-II'
_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  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0298
_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       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10340
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9540
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.423
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1303
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.946
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0319
_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)+(0.0536P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0805
_reflns_number_gt                1021
_reflns_number_total             1303
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2259.cif
_cod_data_source_block           I
_cod_original_cell_volume        658.46(10)
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2213026
_cod_database_fobs_code          2213026
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 0.4317(3) -0.0013(5) 0.57367(11) 0.0488(6) Uani d . 1
C C2 0.2426(3) -0.0952(5) 0.56069(12) 0.0501(6) Uani d . 1
C C3 0.2016(3) -0.3027(6) 0.60417(12) 0.0538(6) Uani d . 1
C C4 0.3481(3) -0.4155(6) 0.65903(13) 0.0545(6) Uani d . 1
H H4 0.3197 -0.5541 0.6875 0.065 Uiso calc R 1
C C5 0.5350(3) -0.3302(5) 0.67320(13) 0.0531(6) Uani d . 1
C C6 0.5718(3) -0.1245(6) 0.62960(13) 0.0539(6) Uani d . 1
H H6 0.6963 -0.0652 0.6380 0.065 Uiso calc R 1
C C7 0.0078(4) -0.4072(7) 0.59118(15) 0.0687(7) Uani d . 1
H H7 -0.0858 -0.3355 0.5525 0.082 Uiso calc R 1
C C8 0.6893(4) -0.4615(7) 0.73225(14) 0.0678(7) Uani d . 1
H H8A 0.7556 -0.3054 0.7622 0.081 Uiso calc R 1
H H8B 0.7758 -0.5682 0.7154 0.081 Uiso calc R 1
H H8C 0.6354 -0.5949 0.7570 0.081 Uiso calc R 1
C C9 0.4811(3) 0.2133(6) 0.53053(14) 0.0538(6) Uani d . 1
H H9 0.6070 0.2674 0.5402 0.065 Uiso calc R 1
C C10 0.4038(3) 0.5390(6) 0.43680(12) 0.0529(6) Uani d . 1
C C11 0.2599(4) 0.6570(5) 0.38320(13) 0.0579(7) Uani d . 1
H H11 0.1355 0.6016 0.3765 0.069 Uiso calc R 1
C C12 0.2991(4) 0.8583(6) 0.33903(14) 0.0613(7) Uani d . 1
C C13 0.4866(4) 0.9297(7) 0.35246(16) 0.0696(7) Uani d . 1
H H13 0.5221 1.0589 0.3238 0.084 Uiso calc R 1
C C14 0.6213(4) 0.8077(7) 0.40885(15) 0.0706(8) Uani d . 1
H H14 0.7460 0.8680 0.4182 0.085 Uiso calc R 1
C C15 0.1434(5) 0.9910(8) 0.27985(16) 0.0814(9) Uani d . 1
H H15A 0.0267 0.9844 0.2895 0.098 Uiso calc R 1
H H15B 0.1306 0.8797 0.2390 0.098 Uiso calc R 1
H H15C 0.1739 1.1936 0.2734 0.098 Uiso calc R 1
N N1 0.3543(3) 0.3305(5) 0.47917(11) 0.0544(5) Uani d . 1
N N2 0.5855(3) 0.6104(5) 0.45063(13) 0.0645(6) Uani d . 1
O O1 0.1024(2) 0.0140(4) 0.50696(9) 0.0645(5) Uani d . 1
H H1 0.1462 0.1326 0.4861 0.097 Uiso calc R 1
O O2 -0.0382(3) -0.5808(5) 0.62748(11) 0.0854(6) 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
C6 C1 C2 118.1(2)
C6 C1 C9 120.1(2)
C2 C1 C9 121.8(2)
O1 C2 C3 119.82(19)
O1 C2 C1 120.5(2)
C3 C2 C1 119.7(2)
C4 C3 C2 119.1(2)
C4 C3 C7 120.1(2)
C2 C3 C7 120.8(2)
C5 C4 C3 122.8(3)
C5 C4 H4 118.6
C3 C4 H4 118.6
C6 C5 C4 116.9(2)
C6 C5 C8 121.9(2)
C4 C5 C8 121.1(3)
C5 C6 C1 123.3(2)
C5 C6 H6 118.3
C1 C6 H6 118.3
O2 C7 C3 124.2(2)
O2 C7 H7 117.9
C3 C7 H7 117.9
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 121.1(2)
N1 C9 H9 119.5
C1 C9 H9 119.5
N2 C10 C11 123.6(2)
N2 C10 N1 119.0(2)
C11 C10 N1 117.4(2)
C10 C11 C12 120.3(2)
C10 C11 H11 119.9
C12 C11 H11 119.9
C13 C12 C11 116.4(3)
C13 C12 C15 122.4(3)
C11 C12 C15 121.2(3)
C12 C13 C14 119.4(3)
C12 C13 H13 120.3
C14 C13 H13 120.3
N2 C14 C13 124.6(3)
N2 C14 H14 117.7
C13 C14 H14 117.7
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C9 N1 C10 120.80(19)
C14 N2 C10 115.7(3)
C2 O1 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.395(3)
C1 C2 1.417(3)
C1 C9 1.443(4)
C2 O1 1.345(3)
C2 C3 1.399(3)
C3 C4 1.388(3)
C3 C7 1.464(3)
C4 C5 1.387(4)
C4 H4 0.9300
C5 C6 1.383(3)
C5 C8 1.498(4)
C6 H6 0.9300
C7 O2 1.210(3)
C7 H7 0.9300
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 N1 1.282(3)
C9 H9 0.9300
C10 N2 1.335(3)
C10 C11 1.373(4)
C10 N1 1.414(3)
C11 C12 1.385(4)
C11 H11 0.9300
C12 C13 1.377(4)
C12 C15 1.508(4)
C13 C14 1.379(4)
C13 H13 0.9300
C14 N2 1.327(4)
C14 H14 0.9300
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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 1.84 2.576(3) 148.4
C8 H8B O2 1_655 0.96 2.63 3.474(4) 146.8
C9 H9 O2 1_665 0.93 2.76 3.618(3) 153.4
C14 H14 O1 1_665 0.93 2.77 3.626(3) 152.8
C15 H15B O2 2_554 0.96 2.61 3.516(4) 157.9
C7 H7 N2 1_445 0.93 2.67 3.521(4) 152.1
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
C6 C1 C2 O1 -179.2(2)
C9 C1 C2 O1 0.2(3)
C6 C1 C2 C3 0.9(3)
C9 C1 C2 C3 -179.7(2)
O1 C2 C3 C4 179.4(2)
C1 C2 C3 C4 -0.7(3)
O1 C2 C3 C7 1.1(4)
C1 C2 C3 C7 -178.9(2)
C2 C3 C4 C5 0.4(4)
C7 C3 C4 C5 178.6(2)
C3 C4 C5 C6 -0.2(4)
C3 C4 C5 C8 -178.9(2)
C4 C5 C6 C1 0.4(3)
C8 C5 C6 C1 179.1(2)
C2 C1 C6 C5 -0.7(4)
C9 C1 C6 C5 179.8(2)
C4 C3 C7 O2 3.6(5)
C2 C3 C7 O2 -178.2(3)
C6 C1 C9 N1 -179.5(2)
C2 C1 C9 N1 1.0(3)
N2 C10 C11 C12 1.2(4)
N1 C10 C11 C12 -178.8(2)
C10 C11 C12 C13 -0.2(4)
C10 C11 C12 C15 -179.9(3)
C11 C12 C13 C14 -2.0(4)
C15 C12 C13 C14 177.8(3)
C12 C13 C14 N2 3.5(5)
C1 C9 N1 C10 -179.5(2)
N2 C10 N1 C9 0.7(3)
C11 C10 N1 C9 -179.4(2)
C13 C14 N2 C10 -2.5(4)
C11 C10 N2 C14 0.2(4)
N1 C10 N2 C14 -179.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655204
