Synthesis, crystal structure, hydrogen bond patterns and Hirshfeld surface analysis of (S)-5-(4-hydroxybenzyl)-imidazolidine-2,4‑dione

Abstract

The title compound, (S)-5-(4-hydroxybenzyl)-imidazolidine-2,4‑dione, a new α-amino acid hydantoin derivative with formula C10H10N2O3 has been synthesized and structurally characterized by MS, 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 crystallizes in the orthorhombic space group P212121 (N°19), Z = 4, and unit cell parameters a = 6.217(3) Å, b = 7.653(3) Å, c = 19.824(8) Å. The molecular structure and crystal packing are stabilized by intermolecular N–H···O and O–H···O hydrogen formed infinite two-dimensional chains, with graph-set C(6), C(5) and C(11) that run along the a, b and c directions forming a two-dimensional network. Hirshfeld surface analysis confirm that the most important contributions for the crystal packing are from N–H··O and O–H··O interactions. Energy framework calculations suggest that the contacts formed between molecules are slightly electrostatic and revealed that interactions exhibit approximately complex zig-zag shape topology in the crystal structure.