Hydantoin-D,L-valine: Synthesis, characterization, and non-covalent interaction analysis from crystallographic studies, DFTB calculations, and Hirshfeld surface analysis

Abstract

The title compound, hydantoin-D,L-daline or (RS)-5-isopropyl-imidazolidine-2,4‑dione, a new amino acid hydantoin derivative with formula C6H10N2O2 has been synthesized and structurally characterized by FT-IR, NMR, and X-ray diffraction techniques. Spectroscopy results are consistent with the skeleton structure. The powder X-ray diffraction data confirms the phase purity of the crystalline sample. Single-crystal X-ray diffraction analysis indicated that the title compound crystallizes in the monoclinic space group P21/c (N°14), Z = 4, and unit cell parameters a = 5.493(3) Å, b = 23.53(2) Å, c = 6.254(3) Å, β= 115.09(4)°, V = 732.1(9) Å3. The molecular structure and crystal packing are stabilized by intermolecular N–H···O, C–H···O, and C–H···π hydrogen bonds forming an infinite two-dimensional network with chains described by the graph-set notation C(5), and centrosymmetric rings with graphs R22(8) and R44(16). The non-covalent interactions were analyzed employing DFTB calculations, which reproduce the main features of the stereochemistry and geometries exhibited by X-ray diffraction. Additionally, these intermolecular interactions were analyzed using Hirshfeld surfaces analysis and 2D fingerprint plots.