Crystal structure, Hirshfeld surface analysis and density functional theory study of 1-nonyl-3-phenyl-quinoxalin-2-one

Nadeem Abad; Karim Chkirate; Fares Hezam Al-Ostoot; Luc Van Meervelt; Sanae Lahmidi; Souad Ferfra; Youssef Ramli; El Mokhtar Essassi

doi:10.1107/S2056989021009737

Crystal structure, Hirshfeld surface analysis and density functional theory study of 1-nonyl-3-phenyl-quinoxalin-2-one

Acta Crystallogr E Crystallogr Commun. 2021 Sep 24;77(Pt 10):1037-1042. doi: 10.1107/S2056989021009737. eCollection 2021 Oct 1.

Authors

Nadeem Abad^{1

2}, Karim Chkirate¹, Fares Hezam Al-Ostoot², Luc Van Meervelt³, Sanae Lahmidi¹, Souad Ferfra¹, Youssef Ramli⁴, El Mokhtar Essassi¹

Affiliations

¹ Laboratory of Heterocyclic Organic Chemistry URAC 21, Pharmacochemistry Competence Center, Av. Ibn Battouta, BP 1014, Faculty of Sciences, Mohammed V University, Rabat, Morocco.
² Department of Biochemistry, Faculty of Education & Science, AlBaydha University, Yemen.
³ KU Leuven, Chemistry Department, Celestijnenlaan 200F box 2404, Leuven (Heverlee), B-3001, Belgium.
⁴ Laboratory of Medicinal Chemistry, Drug Sciences Research Center, Faculty of, Medicine and Pharmacy, Mohammed V University in Rabat, Morocco.

Abstract

In the title mol-ecule, C₂₃H₂₈N₂O, the phenyl ring is inclined to the quinoxaline ring system at a dihedral angle of 20.40 (9)°. In the crystal, C-H⋯O inter-actions between neighbouring mol-ecules form chains along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (70.6%), H⋯C/C⋯H (15.5%) and H⋯O/O⋯H (4.6%) inter-actions. The optimized structure calculated using density functional theory at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated highest occupied mol-ecular orbital (HOMO) and lowest unoccupied mol-ecular orbital (LUMO) energy gap is 3.8904 eV. Part of the n-nonyl chain attached to one of the nitro-gen atoms of the quinoxaline ring system shows disorder and was refined with a double conformation with occupancies of 0.604 (11) and 0.396 (11).

Keywords: Hirshfeld surface analysis; crystal structure; density functional theory; hydrogen bond; quinoxaline.

Grants and funding

This work was funded by Herculesstichting grant AKUL/09/0035.