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

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 P2(1)/c (N degrees 14), Z = 4, and unit cell parameters a = 5.493(3) & Aring;, b = 23.53(2) & Aring;, c = 6.254(3) & Aring;, beta= 115.09(4)degrees, V = 732.1(9) & Aring;(3). The molecular structure and crystal packing are stabilized by intermolecular N-HO, C-HO, and C-Hpi hydrogen bonds forming an infinite two-dimensional network with chains described by the graph-set notation C(5), and centrosymmetric rings with graphs R-2(2)(8) and R-4(4)(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.