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

The title compound, glycidamide (systematic name: oxirane-2-carboxamide), C3H5NO2, 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 angstrom for molecule B inverted on molecule A. In the crystal, molecules are linked by N-H center dot center dot center dot O hydrogen bonds, which lead to the formation of beta-sheet structures enclosing R-2(2)(8) and R-4(2)(8) loops. The beta-sheets are linked by weaker C-H center dot center dot center dot O hydrogen bonds, forming a supramolecular three-dimensional structure.