#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/90/2019099.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_2019099
loop_
_publ_author_name
'Júnior, Anderson A. B. C.'
'De Carvalho, Gustavo S. G.'
'Marques, Lippy F.'
'Corrêa, Charlane C.'
'Da Silva, Adilson D.'
'Machado, Flávia C.'
_publ_section_title
;
 The zwitterionic structure of
 2-hydroxy-4-[(2-hydroxybenzylidene)amino]benzoic acid
;
_journal_coeditor_code           SK3499
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              934
_journal_page_last               936
_journal_paper_doi               10.1107/S0108270113018143
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C14 H11 N O4'
_chemical_formula_moiety         'C14 H11 N O4'
_chemical_formula_sum            'C14 H11 N O4'
_chemical_formula_weight         257.24
_chemical_name_systematic
;
2-{[(4-Carboxy-3-hydroxyphenyl)iminiumyl]methyl}phenolate
;
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.000
_cell_angle_beta                 96.212(2)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   3.83930(10)
_cell_length_b                   18.3309(4)
_cell_length_c                   16.4738(4)
_cell_measurement_reflns_used    16916
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.49
_cell_volume                     1152.58(5)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010) and WinGX (Farrugia, 2012)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Agilent Xcalibur diffractometer with Atlas Gemini Ultra detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            57654
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis PRO (Agilent, 2012), based on expressions derived by Clark &
Reid (1995)]
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536.00
_exptl_crystal_size_max          0.6152
_exptl_crystal_size_mid          0.3365
_exptl_crystal_size_min          0.1202
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.203
_refine_ls_extinction_coef       0.0074(18)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0370
_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)+(0.0601P)²+0.3375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                2006
_reflns_number_total             2349
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3499.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2019099
_cod_database_fobs_code          2019099
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_symmetry_multiplicity
O O1 0.8457(3) 0.38680(5) 0.32616(6) 0.0451(3) Uani d . 1 1
O O2 -0.0306(3) 0.40129(6) -0.08909(6) 0.0548(3) Uani d . 1 1
H H2 -0.1219 0.3728 -0.1235 0.082 Uiso calc R 1 1
O O3 -0.3555(3) 0.18835(6) -0.05976(7) 0.0517(3) Uani d . 1 1
H H3O -0.4509 0.1691 -0.1013 0.077 Uiso calc R 1 1
O O4 -0.3091(4) 0.28165(6) -0.14503(7) 0.0587(4) Uani d . 1 1
N N1 0.4554(3) 0.40605(6) 0.19115(6) 0.0317(3) Uani d . 1 1
H H1N 0.5294 0.3784 0.2316 0.038 Uiso calc R 1 1
C C1 -0.2603(4) 0.25408(8) -0.07654(9) 0.0390(3) Uani d . 1 1
C C2 -0.0840(3) 0.29480(7) -0.00597(8) 0.0320(3) Uani d . 1 1
C C3 -0.0210(4) 0.26326(7) 0.07081(8) 0.0350(3) Uani d . 1 1
H H3 -0.0955 0.2157 0.0784 0.042 Uiso calc R 1 1
C C4 0.1491(4) 0.30062(7) 0.13611(8) 0.0349(3) Uani d . 1 1
H H4 0.1872 0.2788 0.1873 0.042 Uiso calc R 1 1
C C5 0.2629(3) 0.37157(7) 0.12417(7) 0.0298(3) Uani d . 1 1
C C6 0.1985(4) 0.40522(7) 0.04878(8) 0.0338(3) Uani d . 1 1
H H6 0.2709 0.4530 0.0418 0.041 Uiso calc R 1 1
C C7 0.0250(4) 0.36713(7) -0.01626(8) 0.0338(3) Uani d . 1 1
C C8 0.5342(3) 0.47523(7) 0.19883(8) 0.0314(3) Uani d . 1 1
H H8 0.4479 0.5071 0.1575 0.038 Uiso calc R 1 1
C C9 0.7436(3) 0.50374(7) 0.26683(7) 0.0303(3) Uani d . 1 1
C C10 0.8951(3) 0.45695(7) 0.33079(8) 0.0329(3) Uani d . 1 1
C C11 1.0976(4) 0.49017(9) 0.39741(8) 0.0410(3) Uani d . 1 1
H H11 1.2017 0.4613 0.4397 0.049 Uiso calc R 1 1
C C12 1.1427(4) 0.56407(9) 0.40054(9) 0.0442(4) Uani d . 1 1
H H12 1.2740 0.5847 0.4455 0.053 Uiso calc R 1 1
C C13 0.9958(4) 0.60951(8) 0.33760(9) 0.0423(4) Uani d . 1 1
H H13 1.0323 0.6596 0.3406 0.051 Uiso calc R 1 1
C C14 0.7997(4) 0.58003(7) 0.27221(8) 0.0360(3) Uani d . 1 1
H H14 0.7013 0.6102 0.2305 0.043 Uiso calc R 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -1 0 0.3126
-1 1 2 0.2134
0 -1 1 0.0678
1 -1 -2 0.2994
2 2 0 0.3248
1 0 -2 0.2868
0 -1 2 0.1336
0 -2 1 0.0949
1 -2 1 0.2819
0 -2 0 0.1380
0 -1 -1 0.1456
0 2 1 0.1499
0 0 -2 0.1632
1 1 -2 0.2860
0 1 -1 0.0523
0 0 2 0.1751
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 O3 H3O 109.5 ?
C7 O2 H2 109.5 ?
C8 N1 C5 127.39(11) y
C8 N1 H1N 116.3 ?
C5 N1 H1N 116.3 ?
C6 C5 C4 120.95(12) ?
C6 C5 N1 122.00(12) ?
C4 C5 N1 117.01(11) ?
C3 C2 C7 118.54(12) ?
C3 C2 C1 121.66(12) ?
C7 C2 C1 119.80(12) ?
C8 C9 C14 119.11(12) ?
C8 C9 C10 120.99(12) ?
C14 C9 C10 119.89(12) ?
O2 C7 C6 118.00(12) ?
O2 C7 C2 121.61(12) ?
C6 C7 C2 120.39(12) ?
O4 C1 O3 123.88(13) ?
O4 C1 C2 121.55(13) ?
O3 C1 C2 114.57(12) ?
N1 C8 C9 122.95(12) y
N1 C8 H8 118.5 ?
C9 C8 H8 118.5 ?
C4 C3 C2 121.69(12) ?
C4 C3 H3 119.2 ?
C2 C3 H3 119.2 ?
C5 C6 C7 119.51(12) ?
C5 C6 H6 120.2 ?
C7 C6 H6 120.2 ?
C12 C11 C10 120.91(13) ?
C12 C11 H11 119.5 ?
C10 C11 H11 119.5 ?
C14 C13 C12 119.67(13) ?
C14 C13 H13 120.2 ?
C12 C13 H13 120.2 ?
C13 C14 C9 120.67(13) ?
C13 C14 H14 119.7 ?
C9 C14 H14 119.7 ?
C11 C12 C13 121.53(13) ?
C11 C12 H12 119.2 ?
C13 C12 H12 119.2 ?
O1 C10 C11 122.43(12) ?
O1 C10 C9 120.26(12) ?
C11 C10 C9 117.31(12) ?
C3 C4 C5 118.88(12) ?
C3 C4 H4 120.6 ?
C5 C4 H4 120.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 1.3008(17) y
O3 C1 1.2975(18) y
O3 H3O 0.8200 ?
O2 C7 1.3497(16) y
O2 H2 0.8200 ?
N1 C8 1.3067(17) y
N1 C5 1.4095(16) y
N1 H1N 0.8600 ?
O4 C1 1.2319(17) y
C5 C6 1.3848(18) ?
C5 C4 1.3929(18) ?
C2 C3 1.3879(18) ?
C2 C7 1.4062(19) ?
C2 C1 1.4820(18) ?
C9 C8 1.4069(18) ?
C9 C14 1.4163(18) ?
C9 C10 1.4323(18) ?
C7 C6 1.3873(18) ?
C8 H8 0.9300 ?
C3 C4 1.3786(19) ?
C3 H3 0.9300 ?
C6 H6 0.9300 ?
C11 C12 1.366(2) ?
C11 C10 1.4126(19) ?
C11 H11 0.9300 ?
C13 C14 1.358(2) ?
C13 C12 1.400(2) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C12 H12 0.9300 ?
C4 H4 0.9300 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N1 2.5682(15) . n
O1 O3 2.5058(15) 4_766 n
O1 C1 3.3169(18) 4_766 n
O2 C14 3.2530(17) 3_665 n
O2 O4 2.5669(17) . n
O2 C8 3.3725(17) 3_565 n
O3 O1 2.5058(15) 4_465 n
O3 C11 3.348(2) 4_465 n
O3 C10 3.2998(17) 4_465 n
O4 O2 2.5669(16) . n
N1 C10 3.4440(16) 1_455 n
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
N1 H1N O1 . 0.86 1.88 2.5682(15) 136 yes
O2 H2 O4 . 0.82 1.84 2.5669(17) 147 yes
O3 H3O O1 4_465 0.82 1.70 2.5058(15) 167 yes
C3 H3 O3 . 0.93 2.44 2.7502(18) 100 yes
C8 H8 O2 3_565 0.93 2.50 3.3725(17) 156 yes
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
_geom_torsion_publ_flag
C8 N1 C5 C4 -167.01(13) yes
C8 N1 C5 C6 15.2(2) yes
C5 N1 C8 C9 -176.72(12) yes
O3 C1 C2 C3 1.6(2) yes
O3 C1 C2 C7 -178.75(13) yes
O4 C1 C2 C3 -178.39(15) yes
O4 C1 C2 C7 1.3(2) yes
C1 C2 C7 O2 0.8(2) yes
C3 C2 C7 O2 -179.45(13) yes
C3 C4 C5 N1 -176.00(13) yes
N1 C5 C6 C7 176.29(13) yes
C5 C6 C7 O2 -179.38(13) yes
N1 C8 C9 C10 2.52(19) yes
N1 C8 C9 C14 -176.53(12) yes
C8 C9 C10 O1 1.19(18) yes
C14 C9 C10 O1 -179.78(12) yes
O1 C10 C11 C12 -179.66(13) yes
