Different spatial orientations of amide derivatives on anion coordination

Abstract

The N-[2-(4-methoxypheny)-ethyl]-2-(quinolin-8-yl-amino)acetamide is a stretched amide, whose protonated perchlorate salt has a tweezer-like geometry. The self assembly of the salt molecules through weak C–H⋯π and C–H⋯O interactions gives a channel like structure. The crystal structure of two salts of N-quinolin-8-yl-2-(quinolin-8-yloxy)acetamide (II) is determined. The corresponding perchlorate salt arises from di-protonatation of the parent amide derivative, whereas the tetrafluroborate salt formed is a mono-protonated species of the amide derivative II. The di-protonated species has a concave shape but mono-protonated species adopts an S-shaped geometry.