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rac-3-exo-Ammonio-7-anti-carb­oxy­tricyclo­[2.2.1.0.2,6]heptane-3-endo-carboxyl­ate monohydrate

By Graham Smith, Urs D. Wermuth and Ian D. Jenkins

Abstract

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

Topics: Organic Papers
Publisher: International Union of Crystallography
OAI identifier: oai:pubmedcentral.nih.gov:3344580
Provided by: PubMed Central
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    Citations

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    5. (1979). The structures of similar tricyclic norbornane compounds are rare in the crystallographic literature. The nortricyclic keto acid which served as the precursor to (IV) in the synthesis of (I) (Fig. 3) is known

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