Self-assembly of methacrylamides assisted by an interplay of N–H⋯O, C–H⋯O, C–H⋯π and π–π interactions

Abstract

Solid state self-assembly of methacrylamides (1–3) with intermolecular N–H⋯O and C–H⋯O hydrogen bonds are discussed. Interesting structures in the crystal lattice of 1 and 2 are ascribed to the aromatic surfaces that are orthogonal and twisted to each other along the hydrogen bonded chains. In addition, an interconnected network of face-to-face (π⋯π) and edge-to-face (C–H⋯π) interactions have been observed which are cooperative in nature. Compound 3 showed a staggered packing of adamantane groups along the H-bonded chains. In all three structures, the self-assembly was facilitated by strong hydrogen bonding, π⋯π interactions and packing forces involving bulky groups.