Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acryl-amide.

The title compound, glycidamide (systematic name: oxirane-2-carboxamide), C3H5NO2, is the mutagenic and genotoxic metabolite of acryl-amide, a food contaminant and industrial chemical that has been classified as being probably carcinogenic to humans. Synthesized via the reaction of acrylo-nitrile and hydrogen peroxide, it crystallizes with both enanti-omers occurring as two crystallographically independent mol-ecules (A and B) in the asymmetric unit. They have similar conformations with an r.m.s. deviation of 0.0809 Šfor mol-ecule B inverted on mol-ecule A. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, which lead to the formation of ß-sheet structures enclosing R 2 (2)(8) and R 4 (2)(8) loops. The ß-sheets are linked by weaker C-H⋯O hydrogen bonds, forming a supra-molecular three-dimensional structure.