Crystal structure, hydrogen bond patterns, Hirshfeld surface analysis, and topological studies (NCI) of 1,5,5-trimethyl-imidazolidine-2,4-dione; an organic compound with high symmetry crystallizing in the tetragonal space group I4/m

Abstract

The title compound, 1,5,5-trimethyl-imidazolidine-2,4‑dione was characterized by FT-IR, 1H NMR, and 13C NMR spectroscopy techniques. The crystal structure was established by single-crystal X-ray diffraction. The powder X-ray powder diffraction analysis confirms the phase purity of the crystalline sample. The hydantoin with formula C6H10N2O2 crystallizes in the tetragonal space group I4/m (N°87), Z=8, and unit cell parameters a=15.554(2) Å, c=6.623(6) Å. This space group is very infrequent to find in purely organic molecules and is since, in the asymmetric unit, the hydantoin ring lies on a mirror plane m. The crystalline packing is stabilized by the formation of intermolecular interactions of the strong hydrogen bond type of the N–H···O between the neighboring hydantoin rings. In addition, the crystalline structure presents the formation of weaker unconventional hydrogen bonds of the C–H···O type. These hydrogen bonds give rise to the formation of 8, 24, and 36-membered ring-type supramolecular structures described by the graphs R22(8), R44(24), and R88(36), respectively, which govern the packing of the supramolecular structure of 1,5,5-trimethyl-imidazolidine-2,4‑dione.Hirshfeld surface analysis of the crystal structure shows that the most important contributions for the crystal packing are from H···H (58.3%) and H··O/O··H (34.0%) interactions, which indicate that van der Waals interactions are the dominant forces in the crystal packing. Energy framework calculations suggest that the contacts formed between molecules are slightly electrostatic.These intermolecular interactions were also investigated through topological analysis of the electron density (ρ) employing the NCI method. Experimental and theoretical results obtained for this new hydantoin compound suggest that N–H···O and C–H···O interactions play an important role in the stabilization of its supramolecular structure.