Reinvestigation of the crystal structure of <i>N</i>-(4-chlorobenzylidene)-2-hydroxyaniline: a three-dimensional structure containing O—H···N, O—H···O and C—H···π(arene) hydrogen bonds
Girisha, Marisiddaiah; Yathirajan, Hemmige S.; Rathore, Ravindranath S.; Glidewell, Christopher; Acta Crystallographica Section E 74 (2018) 376–379; doi:10.1107/S205698901800244X

data_2242397
_publ_section_title
;
 Reinvestigation of the crystal structure of
 <i>N</i>-(4-chlorobenzylidene)-2-hydroxyaniline: a three-dimensional
 structure containing O---H&#x00B7;&#x00B7;&#x00B7;N,
 O---H&#x00B7;&#x00B7;&#x00B7;O and C---H&#x00B7;&#x00B7;&#x00B7;\p(arene)
 hydrogen bonds
;
_journal_coeditor_code           ZL2725
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              376
_journal_page_last               379
_journal_paper_doi               10.1107/S205698901800244X
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C13 H10 Cl N O'
_chemical_formula_moiety         'C13 H10 Cl N O'
_chemical_formula_sum            'C13 H10 Cl N O'
_chemical_formula_weight         231.67
_chemical_name_systematic
;
<i>N</i>-(4-chlorobenzylidene)-2-hydroxyaniline
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 101.521(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0830(17)
_cell_length_b                   5.8746(6)
_cell_length_c                   14.825(2)
_cell_measurement_reflns_used    2571
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.554
_cell_measurement_theta_min      2.319
_cell_volume                     1116.5(2)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015<i>b</i>) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.319
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
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_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0322P)^2^+0.4436P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                1556
_reflns_number_total             2565
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            zl2725sup1.cif
_cod_data_source_block           I
_cod_database_code               2242397
_cod_database_fobs_code          2242397
_shelx_estimated_absorpt_t_min   0.928
_shelx_estimated_absorpt_t_max   0.957
_shelx_hkl_checksum              42362
_shelx_res_checksum              9617
_shelxl_version_number           2.014