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

• Published in: Journal of molecular structure 2021-07, Vol.1236, p.130361, Article 130361
• Main Authors: Delgado, Gerzon E., Mora, Asiloé J., Seijas, Luis E., Rincón, Luis, Marroquin, Gustavo, Cisterna, Jonathan, Cárdenas, Alejandro, Brito, Iván
• Format: Article
• Language: English
• Subjects: Energy framework; Hirshfeld surface analysis; hydrogen bond patterns; NCI calculations; Powder X-ray diffraction; thiohydantoin
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2021.130361

•Crystal structure of a new thiohydantoin derivative, was determined from powder X-ray diffraction data.•The IR and NMR spectra confirmed the X-ray diffraction results.•Intermolecular interactions were examined using X-ray diffraction results and compared with those obtained by electron density analysis; NCI calculations, Hirshfeld surfaces and 2D fingerprint plots, and Energy frameworks calculations. 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, 1H-NMR, and 13C-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 P21/c, Z=4. The crystal packing is controlled by N–H···O, N–H···S and C–H···O hydrogen bond interactions, forming infinite two-dimensional sheets with graph-set motifs R22(8), R12(7), and R66(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.