Synthesis, structure and Hirshfeld surface analysis of 1,3-bis-[(1-octyl-1 H-1,2,3-triazol-4-yl)meth-yl]-1 H-benzo[ d]imidazol-2(3 H)-one

Mustapha Zouhair; Lhoussaine El Ghayati; Hanae El Monfalouti; Hicham Abchihi; Tuncer Hökelek; Mazzah Ahmed; Joel T Mague; Nada Kheira Sebbar

doi:10.1107/S2056989023009891

Synthesis, structure and Hirshfeld surface analysis of 1,3-bis-[(1-octyl-1 H-1,2,3-triazol-4-yl)meth-yl]-1 H-benzo[ d]imidazol-2(3 H)-one

Acta Crystallogr E Crystallogr Commun. 2023 Nov 21;79(Pt 12):1179-1182. doi: 10.1107/S2056989023009891. eCollection 2023 Dec 1.

Authors

Mustapha Zouhair¹, Lhoussaine El Ghayati¹, Hanae El Monfalouti², Hicham Abchihi¹, Tuncer Hökelek³, Mazzah Ahmed⁴, Joel T Mague⁵, Nada Kheira Sebbar^{6

2}

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 Laboratory of Plant Chemistry, Organic and Bioorganic Synthesis, Faculty of Sciences, Mohammed V University in Rabat, 4 Avenue Ibn Battouta, BP 1014 RP, Morocco.
³ Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Türkiye.
⁴ Science and Technology of Lille USR 3290, Villeneuve d'ascq cedex, France.
⁵ Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.
⁶ Laboratory of Organic and Physical Chemistry, Applied Bioorganic Chemistry Team, Faculty of Sciences, Ibn Zohr University, Agadir, Morocco.

Abstract

The title mol-ecule, C₂₉H₄₄N₈O, adopts a conformation resembling a two-bladed fan with the octyl chains largely in fully extended conformations. In the crystal, C-H⋯O hydrogen bonds form chains of mol-ecules extending along the b-axis direction, which are linked by weak C-H⋯N hydrogen bonds and C-H⋯π inter-actions to generate a three-dimensional network. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (68.3%), H⋯N/N⋯H (15.7%) and H⋯C/C⋯H (10.4%) inter-actions.

Keywords: C—H⋯π(ring) interaction; benzimidazolone; crystal structure; hydrogen bond; triazole.

Grants and funding

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory. TH is grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).