#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/38/2233806.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_2233806
loop_
_publ_author_name
'Zheng, Zhen Nu'
'Lee, Soon W.'
_publ_section_title
;
 (E)-2-{4-[(Pyridin-2-yl)methylideneamino]phenyl}acetic acid
;
_journal_coeditor_code           FY2044
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o774
_journal_paper_doi               10.1107/S1600536812006472
_journal_volume                  68
_journal_year                    2012
_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_name_systematic
;
(E)-2-{4-[(Pyridin-2-yl)methylideneamino]phenyl}acetic acid
;
_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                 96.6230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.15580(10)
_cell_length_b                   25.7790(5)
_cell_length_c                   11.2213(2)
_cell_measurement_reflns_used    6688
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      2.42
_cell_volume                     1194.14(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2007)'
_computing_publication_material  'SHELXTL (Bruker, 2007'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19023
_diffrn_reflns_theta_full        28.42
_diffrn_reflns_theta_max         28.42
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.189
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0423
_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)+(0.0594P)²+0.0884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                2113
_reflns_number_total             2999
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fy2044.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233806
_cod_database_fobs_code          2233806
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
_atom_site_symmetry_multiplicity
O O1 0.0141(3) 0.59412(4) 0.29429(8) 0.0559(3) Uani d . 1 1
O O2 -0.1260(4) 0.62479(4) 0.11244(10) 0.0854(4) Uani d . 1 1
N N1 0.6832(3) 0.31705(4) 0.64271(10) 0.0498(3) Uani d . 1 1
N N2 0.2167(3) 0.35524(4) 0.37215(9) 0.0468(3) Uani d . 1 1
C C1 0.5054(3) 0.30923(5) 0.53680(11) 0.0433(3) Uani d . 1 1
C C2 0.4438(4) 0.25998(5) 0.49147(14) 0.0582(4) Uani d . 1 1
H H2 0.3247 0.2554 0.4168 0.070 Uiso calc R 1 1
C C3 0.5605(4) 0.21775(6) 0.55782(16) 0.0686(5) Uani d . 1 1
H H3 0.5219 0.1843 0.5285 0.082 Uiso calc R 1 1
C C4 0.7336(4) 0.22551(6) 0.66725(15) 0.0671(5) Uani d . 1 1
H H4 0.8104 0.1975 0.7146 0.081 Uiso calc R 1 1
C C5 0.7917(4) 0.27542(6) 0.70586(13) 0.0626(4) Uani d . 1 1
H H5 0.9130 0.2806 0.7799 0.075 Uiso calc R 1 1
C C6 0.3776(3) 0.35647(5) 0.47493(11) 0.0439(3) Uani d . 1 1
H H6 0.4165 0.3884 0.5126 0.053 Uiso calc R 1 1
C C7 0.0845(3) 0.40250(4) 0.32274(11) 0.0405(3) Uani d . 1 1
C C8 -0.0533(3) 0.43940(5) 0.39151(11) 0.0452(3) Uani d . 1 1
H H8 -0.0541 0.4341 0.4735 0.054 Uiso calc R 1 1
C C9 -0.1887(3) 0.48373(5) 0.33884(12) 0.0457(3) Uani d . 1 1
H H9 -0.2835 0.5078 0.3858 0.055 Uiso calc R 1 1
C C10 -0.1870(3) 0.49330(4) 0.21741(11) 0.0400(3) Uani d . 1 1
C C11 -0.0539(3) 0.45583(5) 0.14942(11) 0.0433(3) Uani d . 1 1
H H11 -0.0518 0.4612 0.0676 0.052 Uiso calc R 1 1
C C12 0.0758(3) 0.41058(5) 0.20048(11) 0.0449(3) Uani d . 1 1
H H12 0.1575 0.3855 0.1526 0.054 Uiso calc R 1 1
C C13 -0.3321(3) 0.54233(5) 0.16057(13) 0.0491(3) Uani d . 1 1
H H13A -0.3663 0.5372 0.0744 0.059 Uiso calc R 1 1
H H13B -0.5432 0.5474 0.1877 0.059 Uiso calc R 1 1
C C14 -0.1385(3) 0.59138(5) 0.18526(12) 0.0448(3) Uani d . 1 1
H HO1 0.130(5) 0.6261(9) 0.3040(17) 0.097(6) Uiso d . 1 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
C14 O1 HO1 109.6(12)
C5 N1 C1 117.88(11)
C6 N2 C7 118.28(10)
N1 C1 C2 121.65(11)
N1 C1 C6 115.24(10)
C2 C1 C6 123.11(11)
C3 C2 C1 119.33(13)
C3 C2 H2 120.3
C1 C2 H2 120.3
C4 C3 C2 119.17(13)
C4 C3 H3 120.4
C2 C3 H3 120.4
C3 C4 C5 118.54(13)
C3 C4 H4 120.7
C5 C4 H4 120.7
N1 C5 C4 123.39(14)
N1 C5 H5 118.3
C4 C5 H5 118.3
N2 C6 C1 122.27(11)
N2 C6 H6 118.9
C1 C6 H6 118.9
C12 C7 C8 118.82(11)
C12 C7 N2 118.70(11)
C8 C7 N2 122.37(11)
C9 C8 C7 120.28(11)
C9 C8 H8 119.9
C7 C8 H8 119.9
C8 C9 C10 121.46(12)
C8 C9 H9 119.3
C10 C9 H9 119.3
C11 C10 C9 117.72(11)
C11 C10 C13 121.11(11)
C9 C10 C13 121.16(12)
C12 C11 C10 121.46(11)
C12 C11 H11 119.3
C10 C11 H11 119.3
C11 C12 C7 120.18(12)
C11 C12 H12 119.9
C7 C12 H12 119.9
C14 C13 C10 116.48(10)
C14 C13 H13A 108.2
C10 C13 H13A 108.2
C14 C13 H13B 108.2
C10 C13 H13B 108.2
H13A C13 H13B 107.3
O2 C14 O1 123.01(13)
O2 C14 C13 123.00(12)
O1 C14 C13 113.99(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C14 1.3135(15)
O1 HO1 0.95(2)
O2 C14 1.1925(15)
N1 C5 1.3353(16)
N1 C1 1.3404(16)
N2 C6 1.2651(15)
N2 C7 1.4222(15)
C1 C2 1.3806(17)
C1 C6 1.4703(16)
C2 C3 1.375(2)
C2 H2 0.9300
C3 C4 1.364(2)
C3 H3 0.9300
C4 C5 1.370(2)
C4 H4 0.9300
C5 H5 0.9300
C6 H6 0.9300
C7 C12 1.3840(17)
C7 C8 1.3895(18)
C8 C9 1.3766(17)
C8 H8 0.9300
C9 C10 1.3856(18)
C9 H9 0.9300
C10 C11 1.3852(18)
C10 C13 1.5097(17)
C11 C12 1.3813(17)
C11 H11 0.9300
C12 H12 0.9300
C13 C14 1.5070(19)
C13 H13A 0.9700
C13 H13B 0.9700
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 HO1 N1 3_666 0.95(2) 1.73(2) 2.6686(15) 165.9(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657489
