Research Article: rac-3-exo-Ammonio-7-anti-carb­oxy­tricyclo­[,6]heptane-3-endo-carboxyl­ate monohydrate

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.

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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 ▶).