Crystal structure, Hirshfeld surface analysis, inter-action energy and energy framework calculations, as well as density functional theory (DFT) com-putation, of methyl 2-oxo-1-(prop-2-yn-yl)-1,2-di-hydro-quinoline-4-carboxyl-ate

Ayoub El-Mrabet; Amal Haoudi; Samira Dalbouha; Mohamed Khalid Skalli; Tuncer Hökelek; Frederic Capet; Youssef Kandri Rodi; Ahmed Mazzah; Nada Kheira Sebbar

doi:10.1107/S2056989023007557

Crystal structure, Hirshfeld surface analysis, inter-action energy and energy framework calculations, as well as density functional theory (DFT) com-putation, of methyl 2-oxo-1-(prop-2-yn-yl)-1,2-di-hydro-quinoline-4-carboxyl-ate

Acta Crystallogr E Crystallogr Commun. 2023 Sep 8;79(Pt 10):883-889. doi: 10.1107/S2056989023007557. eCollection 2023 Oct 1.

Authors

Ayoub El-Mrabet¹, Amal Haoudi¹, Samira Dalbouha^{2

3}, Mohamed Khalid Skalli¹, Tuncer Hökelek⁴, Frederic Capet⁵, Youssef Kandri Rodi¹, Ahmed Mazzah⁶, Nada Kheira Sebbar⁷

Affiliations

¹ Laboratory of Applied Organic Chemistry, Faculty of Science and Technology, University of Sidi Mohamed Ben Abdellah, BP 2202, Fez, Morocco.
² Laboratory of Organic Chemistry and Physical Chemistry, Research Team: Molecular Modeling, Materials and Environment, Department of Chemistry, Faculty of Sciences, University Ibn Zohr in Agadir, BP 8106 Agadir, Morocco.
³ Laboratory of Spectroscopy, Molecular Modeling, Materials, Nanomaterials, Water and Environment, CERNE2D, Faculty of Sciences, Mohammed V University in Rabat, Av. Ibn Battouta, BP 1014, Rabat, Morocco.
⁴ Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Türkiye.
⁵ University of Lille, CNRS, UMR 8181, UCCS, Unité de catalyse et Chimie du solide, F-59000 Lille, France.
⁶ University of Lille, CNRS, UAR 3290, MSAP, Miniaturization for Synthesis, Analysis and Proteomics, F-59000 Lille, France.
⁷ Laboratoire de Chimie Bioorganique Appliquée, Faculté des Sciences, Université Ibnou Zohr, Agadir, Morocco.

Abstract

In the title mol-ecule, C₁₄H₁₁NO₃, the di-hydro-quinoline core deviates slightly from planarity, indicated by the dihedral angle of 1.07 (3)° between the two six-membered rings. In the crystal, layers of mol-ecules almost parallel to the bc plane are formed by C-H⋯O hydro-gen bonds. These are joined by π-π stacking inter-actions. A Hirshfeld surface analysis revealed that the most important contributions to the crystal packing are from H⋯H (36.0%), H⋯C/C⋯H (28.9%) and H⋯O/O⋯H (23.5%) inter-actions. The evaluation of the electrostatic, dispersion and total energy frameworks indicates that the stabilization is dominated by the dispersion energy contribution. Moreover, the mol-ecular structure optimized by density functional theory (DFT) at the B3LYP/6-311G(d,p) level is com-pared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

Keywords: C—H⋯O hydrogen bonds; crystal structure; dihydroquinoline; π-stacking.

Grants and funding

Funding for this research was provided by: Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004 to T. Hökelek).