Synthesis, crystal structure and Hirshfeld surface analysis of (4-methyl-phen-yl)[1-(penta-fluoro-phen-yl)-5-(tri-fluoro-meth-yl)-1 H-1,2,3-triazol-4-yl]methanone

Nazariy T Pokhodylo; Yurii Slyvka; Evgeny Goreshnik; Roman Lytvyn

doi:10.1107/S2056989021010070

Synthesis, crystal structure and Hirshfeld surface analysis of (4-methyl-phen-yl)[1-(penta-fluoro-phen-yl)-5-(tri-fluoro-meth-yl)-1 H-1,2,3-triazol-4-yl]methanone

Acta Crystallogr E Crystallogr Commun. 2021 Oct 5;77(Pt 11):1067-1071. doi: 10.1107/S2056989021010070. eCollection 2021 Nov 1.

Authors

Nazariy T Pokhodylo¹, Yurii Slyvka², Evgeny Goreshnik³, Roman Lytvyn¹

Affiliations

¹ Department of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya, 6, Lviv, 79005, Ukraine.
² Department of Inorganic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya, 6, Lviv, 79005, Ukraine.
³ Department of Inorganic Chemistry and Technology, Jozef Stefan Institute, Jamova 39, SI-1000 Ljubljana, Slovenia.

Abstract

The title compound, C₁₇H₇F₈N₃O, was obtained via the reaction of 1-azido-2,3,4,5,6-penta-fluoro-benzene with 4,4,4-tri-fluoro-1-(p-tol-yl)butane-1,3-dione using tri-ethyl-amine as a base catalyst and solvent. The dihedral angles between the penta-fluoro-phenyl (A), triazole (B) and p-tolyl (C) rings are A/B = 62.3 (2), B/C = 43.9 (3) and A/C = 19.1 (3)°. In the crystal, the mol-ecules are linked by C-H⋯F and C-H⋯O hydrogen bonds as well as by aromatic π-π stacking inter-actions into a three-dimensional network. To further analyse the inter-molecular inter-actions, a Hirshfeld surface analysis was performed.

Keywords: 1,2,3-triazole; Hirshfeld surface analysis; crystal structure.

Grants and funding

This work was funded by Ministry of Education and Science of Ukraine.