Structural and Computational Analysis of Organic Fluorine-Mediated Interactions in Controlling the Crystal Packing of Tetrafluorinated Secondary Amides in the Presence of Weak C–H···O═C Hydrogen Bonds

Abstract

The structural and computational analysis of small organic compounds containing four fluorine atoms is the theme of this manuscript. A library of fluorinated compounds containing a secondary amide (−CONAr2) group has been synthesized and structurally characterized to understand the influence of multiple C–F bonds in building various supramolecular synthons. The introduction of four C–F bonds in each molecule has resulted into a variety of fluorine-mediated weak hydrogen-bonded synthons and a few C–F···F–C contact-mediated molecular dimers. These molecules offer the possibility of exploring the wide variation in crystal structures resulting from different types of weak interactions offered by organic fluorine (C–F group) connected to an aromatic ring. Herein, we intend to demonstrate the significance of those interactions using structural and computational methods.