Crystal structure, Hirshfeld surface analysis and DFT calculations of (<i>E</i>)-3-[1-(2-hydroxyphenylanilino)ethylidene]-6-methylpyran-2,4-dione
Faraj, Imane; Oubella, Ali; Chkirate, Karim; Al Mamari, Khalil; Hökelek, Tuncer; Mague, Joel T.; El Ghayati, Lhoussaine; Sebbar, Nada Kheira; Essassi, El Mokhtar; Acta Crystallographica Section E 78 (2022) 864–870; doi:10.1107/S2056989022007514

data_2244140
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and DFT calculations of
 (<i>E</i>)-3-[1-(2-hydroxyphenylanilino)ethylidene]-6-methylpyran-2,4-dione
;
_journal_coeditor_code           ZN2020
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              864
_journal_page_last               870
_journal_paper_doi               10.1107/S2056989022007514
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C14 H13 N O4'
_chemical_formula_moiety         'C14 H13 N O4'
_chemical_formula_sum            'C14 H13 N O4'
_chemical_formula_weight         259.25
_chemical_name_systematic
;
(<i>E</i>)-3-[1-(2-Hydroxyphenylanilino)ethylidene]-6-methylpyran-2,4-dione
;
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.038(2)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   11.6407(4)
_cell_length_b                   7.4412(2)
_cell_length_c                   42.2828(12)
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      72.3117
_cell_measurement_theta_min      3.9975
_cell_volume                     3657.42(19)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>SAINT</i>  (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
<i>SHELXTL</i> (Sheldrick, 2008)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT5</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            30476
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         72.384
_diffrn_reflns_theta_min         3.890
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    0.871
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.430
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     520
_refine_ls_number_reflns         7135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0561
_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^)+(0.0569P)^2^+2.3750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1460
_reflns_number_gt                5024
_reflns_number_total             7135
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            zn2020sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2244140
_shelx_estimated_absorpt_t_min   0.801
_shelx_estimated_absorpt_t_max   0.945
_shelx_hkl_checksum              33471
_shelx_res_checksum              8719
_cod_database_fobs_code 2244140