Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acryl­amide

The title compound, glycidamide (systematic name: oxirane-2-carboxamide), C(3)H(5)NO(2), is the mutagenic and genotoxic metabolite of acryl­amide, a food contaminant and industrial chemical that has been classified as being probably carcinogenic to humans. Synthesized via the reaction of acrylo­nitrile and hydrogen peroxide, it crystallizes with both enanti­omers occurring as two crystallographically independent mol­ecules (A and B) in the asymmetric unit. They have similar conformations with an r.m.s. deviation of 0.0809 Å for mol­ecule B inverted on mol­ecule A. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds, which lead to the formation of β-sheet structures enclosing R (2) (2)(8) and R (4) (2)(8) loops. The β-sheets are linked by weaker C—H⋯O hydrogen bonds, forming a supra­molecular three-dimensional structure.