Crystal structure, Hirshfeld surface analysis and DFT calculations of (E)-3-[1-(2-hy-droxy-phenyl-anilino)ethyl-idene]-6-methyl-pyran-2,4-dione

Imane Faraj; Ali Oubella; Karim Chkirate; Khalil Al Mamari; Tuncer Hökelek; Joel T Mague; Lhoussaine El Ghayati; Nada Kheira Sebbar; El Mokhtar Essassi

doi:10.1107/S2056989022007514

Crystal structure, Hirshfeld surface analysis and DFT calculations of (E)-3-[1-(2-hy-droxy-phenyl-anilino)ethyl-idene]-6-methyl-pyran-2,4-dione

Acta Crystallogr E Crystallogr Commun. 2022 Jul 29;78(Pt 8):864-870. doi: 10.1107/S2056989022007514. eCollection 2022 Aug 1.

Authors

Affiliations

¹ Laboratory of Heterocyclic Organic Chemistry, Medicines Science Research Center, Pharmacochemistry Competence Center, Mohammed V University in Rabat, Faculté des Sciences, Av. Ibn Battouta, BP 1014, Rabat, Morocco.
² Laboratory of Chemistry and Environment, Applied Bioorganic Chemistry Team, Faculty of Sciences, Ibn Zohr University, Agadir, Morocco.
³ Laboratoire de Synthése Organique et Physico-Chimie Moléculaire, Département de Chimie, Faculté des Sciences, Semlalia, B.P 2390, Marrakech 40001, Morocco.
⁴ Department Of Chemistry - Faculty of Education - University of Hodiedah, Yemen.
⁵ Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey.
⁶ Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.

Abstract

The asymmetric unit of the title compound, C₁₄H₁₃NO₄, contains three independent mol-ecules, which differ slightly in conformation. Each contains an intra-molecular N-H⋯O hydrogen bond. In the crystal, O-H⋯O hydrogen bonds form chains of mol-ecules, which are linked into corrugated sheets parallel to (03) plane by C-H⋯O hydrogen bonds together with π inter-actions between the carbonyl groups and the 2-hy-droxy-phenyl rings. The layers are linked by further C-H⋯O hydrogen bonds. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (49.0%), H⋯O/O⋯H (28.3%) and H⋯C/C⋯H (10.9%) inter-actions. van der Waals inter-actions are the dominant inter-actions in the crystal packing. Moreover, density functional theory (DFT) optimized structures at the B3LYP/ 6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behavior was elucidated to determine the energy gap of 4.53 eV.

Keywords: crystal structure; hydrogen bond; phenol; pyranone.

Grants and funding

JTM acknowledged the NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory. TH is grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).