4-(4-Acetyl-5-methyl-1 H-1,2,3-triazol-1-yl)benzo-nitrile: crystal structure and Hirshfeld surface analysis

Julio Zukerman-Schpector; Cássio da S Dias; Ricardo S Schwab; Mukesh M Jotani; Edward R T Tiekink

doi:10.1107/S2056989018010885

4-(4-Acetyl-5-methyl-1 H-1,2,3-triazol-1-yl)benzo-nitrile: crystal structure and Hirshfeld surface analysis

Acta Crystallogr E Crystallogr Commun. 2018 Aug 10;74(Pt 9):1195-1200. doi: 10.1107/S2056989018010885. eCollection 2018 Sep 1.

Authors

Julio Zukerman-Schpector¹, Cássio da S Dias², Ricardo S Schwab², Mukesh M Jotani³, Edward R T Tiekink⁴

Affiliations

¹ Laboratório de Cristalografia, Esterodinâmica e Modelagem Molecular, Departamento de Química, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil.
² Departamento de Química, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil.
³ Department of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380001, India.
⁴ Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia.

Abstract

The title compound, C₁₂H₁₀N₄O, comprises a central 1,2,3-triazole ring (r.m.s. deviation = 0.0030 Å) flanked by N-bound 4-cyano-phenyl and C-bound acetyl groups, which make dihedral angles of 54.64 (5) and 6.8 (3)° with the five-membered ring, indicating a twisted mol-ecule. In the crystal, the three-dimensional architecture is sustained by carbonyl-C=O⋯π(triazo-yl), cyano-C≡N⋯π(triazo-yl) (these inter-actions are shown to be attractive based on non-covalent inter-action plots) and π-π stacking inter-actions [inter-centroid separation = 3.9242 (9) Å]. An analysis of the Hirshfeld surface shows the important contributions made by H⋯H (35.9%) and N⋯H (26.2%) contacts to the overall surface, as well as notable contributions by O⋯H (9.9%), C⋯H (8.7%), C⋯C (7.3%) and C⋯N (7.2%) contacts.

Keywords: 1,2,3-triazol-1-yl; Hirshfeld surface analysis; NCI plots; crystal structure; nitrile.

Grants and funding

This work was funded by National Council for Scientific and Technological Development, CNPq grant 303207/2017–5. National Council for Scientific and Technological Development, CNPq grant 475203/2013–5. São Paulo Research Foundation-FAPESP grant 2013/06558-3. GlaxoSmithKline-FAPESP grant 2014/50249-8.