Crystal structure, Hirshfeld surface analysis and density functional theory study of 6-methyl-2-[(5-methyl-isoxazol-3-yl)meth-yl]-1 H-benzimidazole

Ahlam Idrissi; Karim Chkirate; Nadeem Abad; Bahia Djerrari; Redouane Achour; El Mokhtar Essassi; Luc Van Meervelt

doi:10.1107/S2056989021002723

Crystal structure, Hirshfeld surface analysis and density functional theory study of 6-methyl-2-[(5-methyl-isoxazol-3-yl)meth-yl]-1 H-benzimidazole

Acta Crystallogr E Crystallogr Commun. 2021 Mar 19;77(Pt 4):396-401. doi: 10.1107/S2056989021002723. eCollection 2021 Apr 1.

Authors

Ahlam Idrissi¹, Karim Chkirate¹, Nadeem Abad², Bahia Djerrari¹, Redouane Achour¹, El Mokhtar Essassi¹, Luc Van Meervelt³

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, Al-Baydha University, Yemen.
³ KU Leuven, Chemistry Department, Celestijnenlaan 200F box 2404, Leuven, (Heverlee), B-3001, Belgium.

Abstract

In the title mol-ecule, C₁₃H₁₃N₃O, the isoxazole ring is inclined to the benzimidazole ring at a dihedral angle of 69.28 (14)°. In the crystal, N-H⋯N hydrogen bonds between neighboring benzimidazole rings form chains along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (48.8%), H⋯C/C⋯H (20.9%) and H⋯N/N⋯H (19.3%) 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 4.9266 eV.

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