Strychnine-8-ammonio-2-naphthalenesulfonate-water (1/1/3.5): The first structure of a strychnine or brucine compound with a zwitterionic species | Zendy

Graham Smith | Zendy; U.D. Wermuth | Zendy; Peter C. Healy | Zendy; David James Young | Zendy

Open Access

Strychnine-8-ammonio-2-naphthalenesulfonate-water (1/1/3.5): The first structure of a strychnine or brucine compound with a zwitterionic species

Author(s) -

Graham Smith,

U.D. Wermuth,

Peter C. Healy,

David James Young

Publication year - 2006

Publication title -

journal of chemical crystallography

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.143

H-Index - 34

eISSN - 1572-8854

pISSN - 1074-1542

DOI - 10.1007/s10870-006-9085-5

Subject(s) - brucine , strychnine , chemistry , crystal structure , hydrogen bond , orthorhombic crystal system , hydrate , zwitterion , adduct , stereochemistry , crystallography , molecule , organic chemistry , biochemistry

The crystal structure of the 1:1 adduct hydrate of strychnine with 1,7-Cleve's acid (8-amino-2-naphthalenesulfonic acid), namely strychnine-8-ammonio-2-naphthalenesulfonate-water (1/1/3.5) has been determined and provides a unique example of a neutral association involving strychnine and an achiral zwitterionic acid species, previously unobserved in the structures of either strychnine or brucine addition compounds. Crystals are orthorhombic, space group P212121, with Z=4 in a cell with dimensions a=10.4484(8), b=30.850(3), c=9.4998(11) Å. Hydrogen bonding involving all available proton-donor and acceptor sites on all species gives rise to a three-dimensional framework polymer structure. The crystallographic literature for strychnine and brucine and their compounds is also reviewed. © Springer Science+Business Media, LLC 2006

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