N-acetyl-5-isopropyl-2-tioxoimidazolidin-4-one: Synthesis, Spectroscopic Characterization, Crystal Structure, DFT Calculations, Hirshfeld Surface Analysis and Energy Framework Study

Studies based on the role of non-covalent interactions in supramolecular structure of materials with pharmacological properties have gained considerable relevance. Herein, we report the structural characterization of a new thiohydantoin compound which are important heterocyclic scaffolds and a class of well-known molecules for their pharmacological properties. N-acetyl-5-isopropyl-2-thioxoimidazolidin4-one compound has been synthesized and characterized by FT-IR, H-1 NMR and C-13 NMR spectroscopy. Its crystal structure was also determined by single-crystal X-ray diffraction studies. This material crystallizes in the triclinic system with space group P (1) over bar (N degrees 2), Z center dot center dot center dot 4, with two independent molecules in the asymmetric unit. The crystal packing is governed by N-H center dot center dot center dot center dot O hydrogen bond-type intermolecular interactions, forming infinite one-dimensional chains with graph-set motif C(6). The manifestations of cooperative effects in the formation of supramolecular synthons observed were analyzed from the fully optimized clusters employing a DFT/B3LYP level of calculations, which reproduce the main features of the stereochemistry and geometries of the synthons exhibited by X-ray diffraction. Additionally, these intermolecular interactions were analyzed using Hirshfeld surfaces analysis, 2D finger print plots, shape index topological surfaces and 3D energy framework (crystal packing in terms on energy). (C) 2020 Elsevier B.V. All rights reserved.