IDENTIFICATION OF SUPRAMOLECULAR DIMERS \nIN THE CRYSTAL STRUCTURE OF (Z)-1-(((5-FLUOROPYRIDIN-2-YL)AMINO)METHYLENE)NAPHTHALEN-2(1H)-ONE \nvia C(sp2)–H⋯F HYDROGEN BONDING: A COMBINED \nEXPERIMENTAL AND THEORETICAL STUDY

Abstract

Abstract Title compound C 16 H 11 FN 2 O ( 1 ) is nearly planar, and adopts the keto-amine form with a strong intramolecular N–H⋯O hydrogen bond. Interestingly, the compound features an intramolecular C–H⋯N weak interaction in the crystal. In addition, the molecules of 1 form supramolecular dimers via C–F⋯H–C13 weak interactions. The nature and energies of intermolecular noncovalent interactions, which are responsible for the supramolecular dimerization, are studied theoretically using DFT calculations, and the topological analysis of the electron density distribution is performed within the formalism of Bader′s theory (QTAIM method).