The zwitterionic structure of 2-hydroxy-4-[(2-hydroxybenzylidene)amino]benzoic acid
Júnior, Anderson A. B. C.; De Carvalho, Gustavo S. G.; Marques, Lippy F.; Corrêa, Charlane C.; Da Silva, Adilson D.; Machado, Flávia C.; Acta Crystallographica Section C 69 (2013) 934–936; doi:10.1107/S0108270113018143

data_2019099
_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 <i>et al.</i>,
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       '\w 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/[\s^2^(Fo^2^)+(0.0601P)^2^+0.3375P] where P=(Fo^2^+2Fc^2^)/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>2\s(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