Crystal structure and Hirshfeld surface analysis of 3-eth-oxy-1-ethyl-6-nitro-quinoxalin-2(1 H)-one

Seqqat Yousra; Lhoussaine El Ghayati; Tuncer Hökelek; Fouad Ouazzani Chahdi; Joel T Mague; Youssef Kandri Rodi; Nada Kheira Sebbar

doi:10.1107/S2056989023007624

Crystal structure and Hirshfeld surface analysis of 3-eth-oxy-1-ethyl-6-nitro-quinoxalin-2(1 H)-one

Acta Crystallogr E Crystallogr Commun. 2023 Sep 8;79(Pt 10):895-898. doi: 10.1107/S2056989023007624. eCollection 2023 Oct 1.

Authors

Seqqat Yousra¹, Lhoussaine El Ghayati², Tuncer Hökelek³, Fouad Ouazzani Chahdi¹, Joel T Mague⁴, Youssef Kandri Rodi¹, Nada Kheira Sebbar^{5

2}

Affiliations

¹ Laboratory of Applied Organic Chemistry, Faculty of Science and Technology, Sidi Mohammed Ben Abdullah University, Route d'Immouzzer, BP 2202, Fez, Morocco.
² Laboratory of Heterocyclic Organic Chemistry, Medicines Science Research Center, Pharmacochemistry Competence Center, Mohammed V University in Rabat, Faculty of Sciences, Morocco.
³ Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Türkiye.
⁴ Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.
⁵ Laboratory of Organic and physical Chemistry, Applied Bioorganic Chemistry Team, Faculty of Sciences, Ibn Zohr University, Agadir, Morocco.

Abstract

The asymmetric unit of the title compound, C₁₂H₁₃N₃O₄, consists of two mol-ecules differing to a small degree in their conformations. In the crystal, layers of mol-ecules are connected by weak C-H⋯O hydrogen bonds and slipped π-stacking inter-actions. These layers lie parallel to (10) and are stacked along the normal to that plane. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing arise from H⋯H (43.5%) and H⋯O/O⋯H (30.8%) contacts. The density functional theory (DFT) optimized structure of the title compound at the B3LYP/ 6-311 G(d,p) level agrees well with the experimentally determined mol-ecular structure in the solid state.

Keywords: crystal structure; hydrogen bond; quinoxaline; π-stacking.

Grants and funding

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