Date Published: May 01, 2012
Publisher: International Union of Crystallography
Author(s): Graham Smith, Urs D. Wermuth, Ian D. Jenkins.
The racemic title compound, C9H11NO4·H2O, a tricyclic rearranged aminonorbornane dicarboxylic acid, is a conformationally rigid analogue of glutamic acid and exists as an ammonium-carboxylate zwitterion, with the bridghead carboxylic acid group anti-related. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds involving the ammonium, carboxylic acid and water donor groups with both water and carboxyl O-atom acceptors give a three-dimensional framework structure.
For background to G-protein receptors, see: Liu & Doller (2011 ▶). For the Strecher and Bucherer–Bergs reactions, see: Strecher (1850 ▶); Bucherer & Steiner (1934 ▶). For the synthesis of aminonorbornane carboxylic acids, see: Apgar & Ludwig (1972 ▶); Tager & Christensen (1972 ▶); Wermuth (1995 ▶). For the chemistry of hydantoins, see: Avendaño López & González Trigo (1985 ▶). For the structure of a similar monocarboxylic acid tricyclic cage compound, see: Fortier et al. (1979 ▶). For graph-set analysis, see: Etter et al. (1990 ▶).