Combined DFT calculation, Hirshfeld surface analysis, and Energy framework study of non-covalent interactions in the crystal structure of (Z)-5-ethylidene-2-thiohydantoin determined by powder X-ray diffraction

The thiohydantoin core is used in the synthesis and development of new drugs. Furthermore, the study of these materials allows us to analyze the role that non-covalent interactions play in their supramolecular structure and how they can influence their pharmacological properties. Herein, a novel thiohydantoin compound, namely (Z)-5-ethylidene-2-thiohydantoin was synthesized and characterized by FT-IR, H-1-NMR, and C-13-NMR spectroscopy. Its crystal structure was determined and refined by powder X-ray diffraction techniques. This material crystallizes in the monoclinic system with space group P2(1)/c, Z=4. The crystal packing is controlled by N-H center dot center dot center dot O, N-H center dot center dot center dot S and C-H center dot center dot center dot O hydrogen bond interactions, forming infinite two-dimensional sheets with graph-set motifs R-2(2)(8), R-2(1) (7), and R-6(6) (26). NCI calculations, Hirshfeld surface analysis, and the Energy framework study reproduce in good agreement the crystal packing exhibited by the X-ray diffraction study. (C) 2021 Elsevier B.V. All rights reserved.