#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/66/2226647.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_2226647
loop_
_publ_author_name
'Eltayeb, Naser Eltaher'
'Teoh, Siang Guan'
'Fun, Hoong-Kun'
'Chantrapromma, Suchada'
_publ_section_title
;
 (E)-4-Hydroxy-2-[(2-hydroxyphenyl)iminiomethyl]phenolate
;
_journal_coeditor_code           RZ2453
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1536
_journal_page_last               o1537
_journal_paper_doi               10.1107/S1600536810020295
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H11 N O3'
_chemical_formula_moiety         'C13 H11 N O3'
_chemical_formula_sum            'C13 H11 N O3'
_chemical_formula_weight         229.23
_chemical_name_systematic
;
(E)-4-Hydroxy-2-[(2-hydroxyphenyl)iminiomethyl]phenolate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 102.242(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.048(5)
_cell_length_b                   8.187(3)
_cell_length_c                   22.858(10)
_cell_measurement_reflns_used    2967
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.09
_cell_measurement_theta_min      1.82
_cell_volume                     2020.5(15)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD area-detector'
_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  0.0870
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            15107
_diffrn_reflns_theta_full        30.09
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_min         1.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1024P)²+0.2914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1726
_reflns_number_gt                2122
_reflns_number_total             2967
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2453.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2226647
_cod_database_fobs_code          2226647
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O O1 0.33647(12) 0.68246(15) 0.56400(5) 0.0181(3) Uani d . 1 . .
H H1O1 0.339(3) 0.792(4) 0.5686(14) 0.049(8) Uiso d . 1 . .
O O2 0.19184(11) 0.49929(14) 0.43502(5) 0.0172(3) Uani d . 1 . .
O O3 -0.15299(12) 0.01393(15) 0.36222(6) 0.0195(3) Uani d . 1 . .
H H1O3 -0.212(3) 0.001(3) 0.3867(14) 0.045(8) Uiso d . 1 . .
N N1 0.18126(13) 0.43402(17) 0.54431(6) 0.0136(3) Uani d . 1 . .
H H1N1 0.213(2) 0.484(3) 0.5165(12) 0.034(7) Uiso d . 1 . .
C C1 0.22799(14) 0.47819(19) 0.60450(7) 0.0137(3) Uani d . 1 . .
C C2 0.30862(15) 0.6115(2) 0.61334(7) 0.0147(3) Uani d . 1 . .
C C3 0.35926(16) 0.6624(2) 0.67122(8) 0.0167(3) Uani d . 1 . .
H H3 0.413(2) 0.755(3) 0.6766(10) 0.024(6) Uiso d . 1 . .
C C4 0.32876(16) 0.5824(2) 0.71942(8) 0.0177(3) Uani d . 1 . .
H H4 0.363(2) 0.614(3) 0.7600(11) 0.026(6) Uiso d . 1 . .
C C5 0.24766(16) 0.4510(2) 0.71042(8) 0.0178(3) Uani d . 1 . .
H H5 0.227(2) 0.393(3) 0.7447(11) 0.028(6) Uiso d . 1 . .
C C6 0.19743(16) 0.3972(2) 0.65277(7) 0.0161(3) Uani d . 1 . .
H H6 0.1437(19) 0.309(3) 0.6478(9) 0.016(5) Uiso d . 1 . .
C C7 0.09838(15) 0.32381(19) 0.52344(7) 0.0142(3) Uani d . 1 . .
H H7 0.0643(18) 0.254(2) 0.5512(9) 0.013(5) Uiso d . 1 . .
C C8 0.05807(15) 0.29461(19) 0.46077(7) 0.0139(3) Uani d . 1 . .
C C9 0.10800(15) 0.38498(19) 0.41820(7) 0.0139(3) Uani d . 1 . .
C C10 0.06509(16) 0.3443(2) 0.35726(7) 0.0160(3) Uani d . 1 . .
H H10 0.101(2) 0.405(3) 0.3290(11) 0.027(6) Uiso d . 1 . .
C C11 -0.02034(15) 0.2222(2) 0.34016(7) 0.0156(3) Uani d . 1 . .
H H11 -0.049(2) 0.192(3) 0.2956(11) 0.025(6) Uiso d . 1 . .
C C12 -0.06925(15) 0.1342(2) 0.38267(7) 0.0144(3) Uani d . 1 . .
C C13 -0.03095(15) 0.17081(19) 0.44220(7) 0.0146(3) Uani d . 1 . .
H H13 -0.066(2) 0.111(3) 0.4732(10) 0.024(6) Uiso 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 0.0016 '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
C2 O1 H1O1 . . 109.4(19) ?
C12 O3 H1O3 . . 112.0(17) ?
C7 N1 C1 . . 128.22(15) ?
C7 N1 H1N1 . . 114.2(17) ?
C1 N1 H1N1 . . 117.6(17) ?
C6 C1 C2 . . 120.88(14) ?
C6 C1 N1 . . 123.52(15) ?
C2 C1 N1 . . 115.60(14) ?
O1 C2 C3 . . 123.09(15) ?
O1 C2 C1 . . 117.61(14) ?
C3 C2 C1 . . 119.28(15) ?
C4 C3 C2 . . 120.03(16) ?
C4 C3 H3 . . 121.6(14) ?
C2 C3 H3 . . 118.3(14) ?
C3 C4 C5 . . 120.51(15) ?
C3 C4 H4 . . 122.0(14) ?
C5 C4 H4 . . 117.5(14) ?
C4 C5 C6 . . 120.17(16) ?
C4 C5 H5 . . 120.3(14) ?
C6 C5 H5 . . 119.5(14) ?
C5 C6 C1 . . 119.12(16) ?
C5 C6 H6 . . 118.8(13) ?
C1 C6 H6 . . 122.1(13) ?
N1 C7 C8 . . 121.96(15) ?
N1 C7 H7 . . 120.0(12) ?
C8 C7 H7 . . 118.0(12) ?
C13 C8 C9 . . 120.89(14) ?
C13 C8 C7 . . 118.07(14) ?
C9 C8 C7 . . 121.02(15) ?
O2 C9 C10 . . 121.61(14) ?
O2 C9 C8 . . 121.39(14) ?
C10 C9 C8 . . 116.99(15) ?
C11 C10 C9 . . 121.25(15) ?
C11 C10 H10 . . 122.8(14) ?
C9 C10 H10 . . 116.0(14) ?
C10 C11 C12 . . 121.19(15) ?
C10 C11 H11 . . 120.5(12) ?
C12 C11 H11 . . 118.3(12) ?
O3 C12 C13 . . 122.86(14) ?
O3 C12 C11 . . 117.72(15) ?
C13 C12 C11 . . 119.42(15) ?
C12 C13 C8 . . 120.25(14) ?
C12 C13 H13 . . 120.8(13) ?
C8 C13 H13 . . 119.0(13) ?
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
O1 C2 . 1.3608(19) ?
O1 H1O1 . 0.91(3) ?
O2 C9 . 1.316(2) ?
O3 C12 . 1.364(2) ?
O3 H1O3 . 0.95(3) ?
N1 C7 . 1.302(2) ?
N1 C1 . 1.410(2) ?
N1 H1N1 . 0.89(3) ?
C1 C6 . 1.389(2) ?
C1 C2 . 1.396(2) ?
C2 C3 . 1.387(2) ?
C3 C4 . 1.383(2) ?
C3 H3 . 0.96(2) ?
C4 C5 . 1.387(3) ?
C4 H4 . 0.96(2) ?
C5 C6 . 1.389(2) ?
C5 H5 . 0.98(2) ?
C6 H6 . 0.93(2) ?
C7 C8 . 1.427(2) ?
C7 H7 . 0.99(2) ?
C8 C13 . 1.413(2) ?
C8 C9 . 1.423(2) ?
C9 C10 . 1.413(2) ?
C10 C11 . 1.373(2) ?
C10 H10 . 0.97(2) ?
C11 C12 . 1.406(2) ?
C11 H11 . 1.03(2) ?
C12 C13 . 1.370(2) ?
C13 H13 . 1.00(2) ?
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
_geom_hbond_publ_flag
O1 H1O1 O2 7_566 0.90(3) 1.74(3) 2.625(2) 166(3) y
O3 H1O3 O2 3_445 0.95(3) 1.69(3) 2.633(2) 173(2) y
N1 H1N1 O2 1_555 0.89(3) 1.83(3) 2.581(2) 141(2) y
C13 H13 O1 3_445 1.00(2) 2.60(2) 3.411(3) 137.8(18) y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C1 C6 . . . . 5.5(3) ?
C7 N1 C1 C2 . . . . -174.41(15) ?
C6 C1 C2 O1 . . . . 178.56(15) ?
N1 C1 C2 O1 . . . . -1.6(2) ?
C6 C1 C2 C3 . . . . 0.5(2) ?
N1 C1 C2 C3 . . . . -179.68(14) ?
O1 C2 C3 C4 . . . . -178.66(15) ?
C1 C2 C3 C4 . . . . -0.7(2) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
C3 C4 C5 C6 . . . . 0.8(3) ?
C4 C5 C6 C1 . . . . -1.0(3) ?
C2 C1 C6 C5 . . . . 0.4(2) ?
N1 C1 C6 C5 . . . . -179.48(15) ?
C1 N1 C7 C8 . . . . 178.69(15) ?
N1 C7 C8 C13 . . . . 179.06(14) ?
N1 C7 C8 C9 . . . . 0.4(2) ?
C13 C8 C9 O2 . . . . -179.28(14) ?
C7 C8 C9 O2 . . . . -0.7(2) ?
C13 C8 C9 C10 . . . . -0.4(2) ?
C7 C8 C9 C10 . . . . 178.20(15) ?
O2 C9 C10 C11 . . . . 178.48(15) ?
C8 C9 C10 C11 . . . . -0.4(2) ?
C9 C10 C11 C12 . . . . 0.6(3) ?
C10 C11 C12 O3 . . . . -179.51(15) ?
C10 C11 C12 C13 . . . . 0.0(2) ?
O3 C12 C13 C8 . . . . 178.68(14) ?
C11 C12 C13 C8 . . . . -0.8(2) ?
C9 C8 C13 C12 . . . . 1.0(2) ?
C7 C8 C13 C12 . . . . -177.65(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 15251048
2 PubChem 135839390
