Diverse supramolecular arrangement of substituted oxopyrrolidine analogues influenced by weak intermolecular interactions (C-H•••O/C-H•••π/H•••H)

Three analogues of 3-oxopyrrolidines; (S)-1-tert-butyl 2-ethyl-2-((S)-2-nitro-1-p-tolylethyl)-3- oxopyrrolidine-1,2-dicarboxylate, 1, (S)-1-tert-butyl 2-ethyl 2-((S)-1-(4-methoxyphenyl)-2-nitroethyl)- 3-oxopyrrolidine-1,2-dicarboxylate 2, and Ethyl 1-((S)-2-(((benzyloxy)carbonyl)amino)-3- phenylpropanoyl)-2-(2-nitro-1-phenylethyl)-3-oxopyrrolidine-2-carboxylate 3, were synthesized and crystallized in suitable solvents. Crystal structure analysis was carried out by single crystal X-ray diffraction to provide a detailed investigation of the packing and supramolecular arrangement of these analogues. The weak interactions such as C-H center dot center dot center dot O/C-H center dot center dot center dot pi present in the crystal structure of all these analogues (1-3) played a vital role in controlling the conformation of the molecules and construction of dissimilar supramolecular assemblies. This study provides some insight; that even though these oxopyrrolidine analogues, lack a hydrogen bond donor and acceptor system, that upon bulky substitutions, this scaffold can still form fascinating supramolecular assemblies through various weak interactions. The surface interaction was carried out by means of Hirshfeld surface analysis, which depicted the significant intermolecular interactions of a molecule with its neighbor within the structures. (C) 2016 Elsevier B.V. All rights reserved.