title: Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acryl-amide.
abstract: 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 Å for 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 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 supra-molecular three-dimensional structure.
authors.affiliation: Food Chemistry and Toxicology, University of Kaiserslautern, 67663 Kaiserslautern, Germany.
authors.forename: Melanie N
authors.initials: MN
authors.lastname: Hemgesberg
authors.affiliation: Theoretical Chemistry, University of Kaiserslautern, 67663 Kaiserslautern, Germany.
authors.forename: Thorsten
authors.initials: T
authors.lastname: Bonck
authors.affiliation: Food Chemistry and Toxicology, University of Kaiserslautern, 67663 Kaiserslautern, Germany.
authors.forename: Karl-Heinz
authors.initials: KH
authors.lastname: Merz
authors.affiliation: Inorganic Chemistry, University of Kaiserslautern, 67663 Kaiserslautern, Germany.
authors.forename: Yu
authors.initials: Y
authors.lastname: Sun
authors.affiliation: Food Chemistry and Toxicology, University of Kaiserslautern, 67663 Kaiserslautern, Germany.
authors.forename: Dieter
authors.initials: D
authors.lastname: Schrenk
keywords: acryl­amide; crystal structure; genotoxic metabolite; glycidamide; hydrogen bonding; mutagenic; β-sheet