Crystal structure, Hirshfeld surface analysis, and calculations of inter-molecular inter-action energies and energy frameworks of 1-[(1-hexyl-1 H-1,2,3-triazol-4-yl)meth-yl]-3-(1-methyl-ethen-yl)-benzimidazol-2-one

Zakaria El Atrassi; Zakaria Benzekri; Olivier Blacque; Tuncer Hökelek; Ahmed Mazzah; Hassan Cherkaoui; Nada Kheira Sebbar

doi:10.1107/S2056989024008703

Crystal structure, Hirshfeld surface analysis, and calculations of inter-molecular inter-action energies and energy frameworks of 1-[(1-hexyl-1 H-1,2,3-triazol-4-yl)meth-yl]-3-(1-methyl-ethen-yl)-benzimidazol-2-one

Acta Crystallogr E Crystallogr Commun. 2024 Sep 30;80(Pt 10):1075-1080. doi: 10.1107/S2056989024008703. eCollection 2024 Sep 1.

Authors

Zakaria El Atrassi¹, Zakaria Benzekri¹, Olivier Blacque², Tuncer Hökelek³, Ahmed Mazzah⁴, Hassan Cherkaoui¹, Nada Kheira Sebbar^{5

6}

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 University of Zurich, Department of Chemistry B, Winterthurerstrasse 190, 8057 Zurich, Switzerland.
³ Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Türkiye.
⁴ Science and Technology of Lille USR 3290, Villeneuve d'ascq cedex, France.
⁵ Laboratory of Organic and Physical Chemistry, Applied Bioorganic Chemistry Team, Faculty of Sciences, Ibnou Zohr University, Agadir, Morocco.
⁶ Laboratory of Plant Chemistry Organic and Bioorganic Synthesis Faculty of Sciences Mohammed V University in Rabat 4 Avenue Ibn Battouta BP 1014 RP Rabat Morocco.

Abstract

The benzimidazole moiety in the title mol-ecule, C₁₉H₂₅N₅O, is almost planar and oriented nearly perpendicular to the triazole ring. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into a network structure. There are no π-π inter-actions present but two weak C-H⋯π(ring) inter-actions are observed. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (62.0%), H⋯C/C⋯H (16.1%), H⋯N/N⋯H (13.7%) and H⋯O/O⋯H (7.5%) inter-actions. Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the stabilization is dominated via the dispersion energy contributions in the title compound.

Keywords: C—H⋯π(ring) interaction; benzimidazol-2-one; crystal structure; hydrogen bond; triazole.