#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/99/2229998.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_2229998
loop_
_publ_author_name
'Yuan, Xiao-Ling'
_publ_section_title
;
 2-Ethoxy-6-[(3-methylpyridin-2-yl)iminomethyl]phenol
;
_journal_coeditor_code           HB5833
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1064
_journal_paper_doi               10.1107/S1600536811012116
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H16 N2 O2'
_chemical_formula_moiety         'C15 H16 N2 O2'
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_weight         256.30
_chemical_name_systematic
;
2-Ethoxy-6-[(3-methylpyridin-2-yl)iminomethyl]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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.381(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8200(10)
_cell_length_b                   38.385(3)
_cell_length_c                   7.207(2)
_cell_measurement_reflns_used    776
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.5
_cell_volume                     1325.1(5)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω scan'
_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  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0947
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7773
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1694
_refine_ls_R_factor_gt           0.0739
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0714P)²+0.1530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1995
_reflns_number_gt                1265
_reflns_number_total             2849
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5833.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229998
_cod_database_fobs_code          2229998
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
N N1 0.6449(5) 0.84753(6) 0.0653(4) 0.0495(7) Uani d . 1 . .
N N2 0.9399(6) 0.80518(7) 0.2233(4) 0.0604(8) Uani d . 1 . .
O O1 0.3096(5) 0.89291(6) -0.1048(3) 0.0609(7) Uani d . 1 . .
H H1 0.4207 0.8767 -0.0957 0.091 Uiso calc R 1 . .
O O2 -0.0665(5) 0.94125(6) -0.0911(3) 0.0691(7) Uani d . 1 . .
C C1 0.3479(6) 0.88351(8) 0.2257(5) 0.0508(8) Uani d . 1 . .
C C2 0.2310(6) 0.90021(8) 0.0638(4) 0.0458(8) Uani d . 1 . .
C C3 0.0320(7) 0.92615(8) 0.0768(5) 0.0550(9) Uani d . 1 . .
C C4 -0.0520(7) 0.93435(9) 0.2466(5) 0.0656(10) Uani d . 1 . .
H H4 -0.1876 0.9514 0.2543 0.079 Uiso calc R 1 . .
C C5 0.0632(8) 0.91749(10) 0.4080(5) 0.0728(11) Uani d . 1 . .
H H5 0.0057 0.9234 0.5229 0.087 Uiso calc R 1 . .
C C6 0.2592(7) 0.89243(9) 0.3978(5) 0.0625(10) Uani d . 1 . .
H H6 0.3351 0.8811 0.5058 0.075 Uiso calc R 1 . .
C C7 0.5550(7) 0.85676(8) 0.2183(5) 0.0530(9) Uani d . 1 . .
H H7 0.6260 0.8458 0.3286 0.064 Uiso calc R 1 . .
C C8 0.8476(6) 0.82108(8) 0.0640(5) 0.0482(8) Uani d . 1 . .
C C9 0.9424(7) 0.81326(8) -0.1071(5) 0.0504(8) Uani d . 1 . .
C C10 1.1400(7) 0.78743(9) -0.1066(5) 0.0603(10) Uani d . 1 . .
H H10 1.2096 0.7813 -0.2174 0.072 Uiso calc R 1 . .
C C11 1.2348(7) 0.77076(9) 0.0558(6) 0.0666(10) Uani d . 1 . .
H H11 1.3680 0.7532 0.0568 0.080 Uiso calc R 1 . .
C C12 1.1299(7) 0.78039(9) 0.2162(5) 0.0653(10) Uani d . 1 . .
H H12 1.1950 0.7690 0.3263 0.078 Uiso calc R 1 . .
C C13 0.8314(7) 0.83182(9) -0.2831(4) 0.0679(10) Uani d . 1 . .
H H13A 0.9225 0.8231 -0.3855 0.102 Uiso calc R 1 . .
H H13B 0.8669 0.8563 -0.2689 0.102 Uiso calc R 1 . .
H H13C 0.6340 0.8279 -0.3074 0.102 Uiso calc R 1 . .
C C14 -0.2849(7) 0.96607(9) -0.0914(5) 0.0684(11) Uani d . 1 . .
H H14A -0.2220 0.9861 -0.0165 0.082 Uiso calc R 1 . .
H H14B -0.4439 0.9559 -0.0399 0.082 Uiso calc R 1 . .
C C15 -0.3642(9) 0.97670(11) -0.2899(6) 0.0961(14) Uani d . 1 . .
H H15A -0.2014 0.9847 -0.3428 0.144 Uiso calc R 1 . .
H H15B -0.4995 0.9951 -0.2943 0.144 Uiso calc R 1 . .
H H15C -0.4427 0.9571 -0.3600 0.144 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C8 . . 120.5(3) ?
C12 N2 C8 . . 117.5(3) ?
C2 O1 H1 . . 109.5 ?
C3 O2 C14 . . 117.8(3) ?
C2 C1 C6 . . 119.6(3) ?
C2 C1 C7 . . 121.0(3) ?
C6 C1 C7 . . 119.3(3) ?
O1 C2 C3 . . 118.4(3) ?
O1 C2 C1 . . 122.2(3) ?
C3 C2 C1 . . 119.3(3) ?
C4 C3 O2 . . 125.6(3) ?
C4 C3 C2 . . 120.0(3) ?
O2 C3 C2 . . 114.5(3) ?
C3 C4 C5 . . 120.7(3) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 120.0(3) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C5 C6 C1 . . 120.4(3) ?
C5 C6 H6 . . 119.8 ?
C1 C6 H6 . . 119.8 ?
N1 C7 C1 . . 122.2(3) ?
N1 C7 H7 . . 118.9 ?
C1 C7 H7 . . 118.9 ?
N2 C8 C9 . . 123.5(3) ?
N2 C8 N1 . . 119.3(3) ?
C9 C8 N1 . . 117.2(3) ?
C10 C9 C8 . . 116.6(3) ?
C10 C9 C13 . . 121.7(3) ?
C8 C9 C13 . . 121.6(3) ?
C11 C10 C9 . . 120.3(3) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C12 C11 C10 . . 118.6(3) ?
C12 C11 H11 . . 120.7 ?
C10 C11 H11 . . 120.7 ?
N2 C12 C11 . . 123.4(3) ?
N2 C12 H12 . . 118.3 ?
C11 C12 H12 . . 118.3 ?
C9 C13 H13A . . 109.5 ?
C9 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C9 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
O2 C14 C15 . . 107.2(3) ?
O2 C14 H14A . . 110.3 ?
C15 C14 H14A . . 110.3 ?
O2 C14 H14B . . 110.3 ?
C15 C14 H14B . . 110.3 ?
H14A C14 H14B . . 108.5 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 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
N1 C7 . 1.279(4) ?
N1 C8 . 1.410(4) ?
N2 C12 . 1.326(4) ?
N2 C8 . 1.332(4) ?
O1 C2 . 1.342(3) ?
O1 H1 . 0.8200 ?
O2 C3 . 1.378(4) ?
O2 C14 . 1.420(4) ?
C1 C2 . 1.394(4) ?
C1 C6 . 1.399(4) ?
C1 C7 . 1.437(4) ?
C2 C3 . 1.393(4) ?
C3 C4 . 1.368(5) ?
C4 C5 . 1.392(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.356(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.394(4) ?
C9 C10 . 1.375(4) ?
C9 C13 . 1.500(4) ?
C10 C11 . 1.367(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.363(5) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 C15 . 1.496(5) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
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 1.87 2.590(3) 146
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656637
