Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[(2-hydroxy-5-methylbenzylidene)amino]benzonitrile
Faizi, Md. Serajul Haque; Cinar, Emine Berrin; Aydin, Alev Sema; Agar, Erbil; Dege, Necmi; Mashrai, Ashraf; Acta Crystallographica Section E 76 (2020) 1195–1200; doi:10.1107/S2056989020008907

data_2243473
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and DFT studies of
 2-[(2-hydroxy-5-methylbenzylidene)amino]benzonitrile
;
_journal_coeditor_code           ZL2787
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1195
_journal_page_last               1200
_journal_paper_doi               10.1107/S2056989020008907
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C15 H12 N2 O'
_chemical_formula_moiety         'C15 H12 N2 O'
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.27
_chemical_name_systematic
;
2-[(2-Hydroxy-5-methylbenzylidene)amino]benzonitrile
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.8139(3)
_cell_length_b                   27.0470(10)
_cell_length_c                   11.7683(5)
_cell_measurement_reflns_used    13160
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.84
_cell_measurement_theta_min      1.51
_cell_volume                     2487.14(17)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2002)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009),
Mercury (Macrae <i>et al.</i>,  2020)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), PLATON (Spek, 2020),
<i>SHELXL2018/3</i> (Sheldrick, 2015b)
and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2018/3</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15314
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.329
_diffrn_reflns_theta_min         1.506
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           45
_diffrn_source_power             2.25
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.9510
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2002)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.730
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.087
_refine_ls_extinction_coef       0.0048(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2018/3 (Sheldrick 2018)
;
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0529P)^2^+0.0539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                1552
_reflns_number_total             2270
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            zl2787sup1.cif
_cod_data_source_block           I
_cod_database_code               2243473
_cod_database_fobs_code          2243473
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.981
_shelx_hkl_checksum              22810
_shelx_res_checksum              8945