#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/61/2216112.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_2216112
loop_
_publ_author_name
'He-Bing Li'
_publ_section_title
;
 2-Methoxy-6-[(4-methylpyridin-2-yl)iminomethyl]phenol
;
_journal_coeditor_code           SG2194
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4246
_journal_page_last               o4246
_journal_paper_doi               10.1107/S1600536807048350
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H14 N2 O2'
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27
_chemical_name_systematic
;
2-Methoxy-6-[(4-methylpyridin-2-ylimino)methyl]phenol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 94.24(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.997(2)
_cell_length_b                   4.8960(10)
_cell_length_c                   24.729(5)
_cell_measurement_reflns_used    713
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.5
_cell_volume                     1207.1(4)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0597
_diffrn_reflns_av_sigmaI/netI    0.1025
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8333
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_correction_T_min  0.9794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.179
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997a)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0596
_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)+(0.0322P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1592
_reflns_number_gt                1384
_reflns_number_total             2498
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg2194.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2216112
_cod_database_fobs_code          2216112
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O O1 0.25493(18) 0.8248(4) 0.07335(7) 0.0551(6) Uani d . 1
H H1 0.1972 0.9383 0.0789 0.083 Uiso calc R 1
O O2 0.44898(18) 0.4723(4) 0.07002(7) 0.0585(6) Uani d . 1
N N1 0.08363(19) 1.0839(4) 0.12784(8) 0.0442(5) Uani d . 1
N N2 -0.0684(2) 1.3400(4) 0.17759(8) 0.0516(6) Uani d . 1
C C1 0.2269(2) 0.7364(5) 0.16759(10) 0.0407(6) Uani d . 1
C C2 0.2902(2) 0.6903(5) 0.11964(10) 0.0403(6) Uani d . 1
C C3 0.3939(2) 0.4971(5) 0.11899(10) 0.0438(6) Uani d . 1
C C4 0.4341(2) 0.3547(5) 0.16547(11) 0.0491(7) Uani d . 1
H H4 0.5037 0.2288 0.1651 0.059 Uiso calc R 1
C C5 0.3704(3) 0.3993(5) 0.21317(11) 0.0507(7) Uani d . 1
H H5 0.3974 0.3022 0.2444 0.061 Uiso calc R 1
C C6 0.2682(3) 0.5856(5) 0.21406(10) 0.0477(7) Uani d . 1
H H6 0.2259 0.6124 0.2459 0.057 Uiso calc R 1
C C7 0.5342(3) 0.2432(5) 0.06291(11) 0.0584(8) Uani d . 1
H H7A 0.6101 0.2514 0.0890 0.088 Uiso calc R 1
H H7B 0.5645 0.2463 0.0270 0.088 Uiso calc R 1
H H7C 0.4852 0.0775 0.0680 0.088 Uiso calc R 1
C C8 0.1211(2) 0.9378(5) 0.16942(10) 0.0425(6) Uani d . 1
H H8 0.0793 0.9619 0.2014 0.051 Uiso calc R 1
C C9 -0.0183(2) 1.2843(5) 0.13012(10) 0.0412(6) Uani d . 1
C C10 -0.0592(2) 1.4159(5) 0.08256(10) 0.0461(7) Uani d . 1
H H10 -0.0199 1.3710 0.0508 0.055 Uiso calc R 1
C C11 -0.1581(2) 1.6146(5) 0.08139(10) 0.0457(7) Uani d . 1
C C12 -0.2092(2) 1.6755(5) 0.13031(11) 0.0499(7) Uani d . 1
H H12 -0.2747 1.8093 0.1322 0.060 Uiso calc R 1
C C13 -0.1623(3) 1.5363(6) 0.17616(11) 0.0573(8) Uani d . 1
H H13 -0.1983 1.5816 0.2086 0.069 Uiso calc R 1
C C14 -0.2051(3) 1.7581(7) 0.02971(12) 0.0704(9) Uani d . 1
H H14A -0.2917 1.8374 0.0335 0.106 Uiso calc R 1
H H14B -0.2112 1.6291 0.0004 0.106 Uiso calc R 1
H H14C -0.1425 1.8993 0.0222 0.106 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'
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
C2 O1 H1 109.5
C3 O2 C7 117.4(2)
C8 N1 C9 121.4(2)
C9 N2 C13 115.4(2)
C6 C1 C2 118.9(2)
C6 C1 C8 120.3(2)
C2 C1 C8 120.8(2)
O1 C2 C1 122.3(2)
O1 C2 C3 117.9(2)
C1 C2 C3 119.9(2)
O2 C3 C4 125.4(2)
O2 C3 C2 114.5(2)
C4 C3 C2 120.1(2)
C3 C4 C5 120.0(2)
C3 C4 H4 120.0
C5 C4 H4 120.0
C6 C5 C4 120.3(2)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C1 120.8(2)
C5 C6 H6 119.6
C1 C6 H6 119.6
O2 C7 H7A 109.5
O2 C7 H7B 109.5
H7A C7 H7B 109.5
O2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
N1 C8 C1 121.6(2)
N1 C8 H8 119.2
C1 C8 H8 119.2
N2 C9 C10 123.2(2)
N2 C9 N1 119.5(2)
C10 C9 N1 117.3(2)
C9 C10 C11 120.9(2)
C9 C10 H10 119.6
C11 C10 H10 119.6
C12 C11 C10 116.3(2)
C12 C11 C14 122.1(2)
C10 C11 C14 121.6(2)
C13 C12 C11 119.4(2)
C13 C12 H12 120.3
C11 C12 H12 120.3
N2 C13 C12 124.9(2)
N2 C13 H13 117.6
C12 C13 H13 117.6
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.345(3)
O1 H1 0.8200
O2 C3 1.372(3)
O2 C7 1.427(3)
N1 C8 1.285(3)
N1 C9 1.419(3)
N2 C9 1.338(3)
N2 C13 1.342(3)
C1 C6 1.402(3)
C1 C2 1.403(3)
C1 C8 1.449(3)
C2 C3 1.404(3)
C3 C4 1.379(3)
C4 C5 1.399(3)
C4 H4 0.9300
C5 C6 1.370(3)
C5 H5 0.9300
C6 H6 0.9300
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 H8 0.9300
C9 C10 1.376(3)
C10 C11 1.386(3)
C10 H10 0.9300
C11 C12 1.380(3)
C11 C14 1.503(4)
C12 C13 1.375(3)
C12 H12 0.9300
C13 H13 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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
O1 H1 N1 0.82 1.86 2.588(2) 147.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655363
