Synthesis, crystal structure and Hirshfeld surface analysis of 2-(perfluoro-phen-yl)acetamide in comparison with some related compounds

Anton P Novikov; Alexey A Bezdomnikov; Mikhail S Grigoriev; Konstantin E German

doi:10.1107/S2056989021013359

Synthesis, crystal structure and Hirshfeld surface analysis of 2-(perfluoro-phen-yl)acetamide in comparison with some related compounds

Acta Crystallogr E Crystallogr Commun. 2022 Jan 1;78(Pt 1):80-83. doi: 10.1107/S2056989021013359.

Authors

Anton P Novikov^{1

2}, Alexey A Bezdomnikov², Mikhail S Grigoriev², Konstantin E German²

Affiliations

¹ Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya, St, 117198, Moscow, Russian Federation.
² Frumkin Institute of Physical Chemistry and Electrochemistry Russian, Academy of Sciences, 31 Leninsky Prospekt bldg 4, 119071 Moscow, Russian Federation.

Abstract

The mol-ecular and crystal structures of the title compound, C₈H₄F₅NO, were examined by single-crystal X-ray diffraction and Hirshfeld surface analysis. The title compound was synthesized by a new method at the interface of aqueous solutions of LiOH and penta-fluoro-phenyl-aceto-nitrile. In the crystal, hydrogen bonds and π-halogen inter-actions connect the mol-ecules into double layers. Analysis of the Hirshfeld surface showed that the most important contributions to the crystal packing are made by F⋯F (30.4%), C⋯F/F⋯C (22.9%), O⋯H/H⋯O (14.9%), H⋯F/F⋯H (14.0%) and H⋯H (10.2%) contacts. The Hirshfeld surfaces of analogues of the title compound were compared and the effect of perfluorination on the crystal packing was shown.

Keywords: Hirshfeld surface analysis; acetamide; crystal structure; hydrogen bonds; perfluorophenyl.

Grants and funding

This work was funded by Ministry of Science and Higher Education of the Russian Federation grant AAAA-A18-118040590105-4.