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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The Crystal Structure of Indospicine Hydrochloride Hydrate

MP Hegarty, CHL Kennard, KA Byriel and G Smith

Australian Journal of Chemistry 45(6) 1021 - 1025
Published: 1992

Abstract

The crystal structure of the hepatotoxic amino acid indospicine [L-6-amidino-2-aminohexanoic acid, (S)-2,7-diamino-7-iminoheptanoic acid], as its hydrochloride hydrate, has been determined by X-ray diffraction and refined to a residual R 0.036 for 845 observed reflections collected at 173 K. Crystals are orthorhombic, space group P 22121 with 8 molecules in a cell of dimensions a 5.1541(4), b 14.083(1), c 31.781(3) Å . The structure is consistent with the one previously derived from chemical data but with the presence of a terminal amidinium ion and an α-amino acid zwitterion pair. The two independent molecules in the asymmetric unit are conformationally different and form a head-to-tail packing motif linked by NH(amidino)…O(carboxyl) hydrogenbonds (N…O,2.80, 2.85 Å ). The structure also features extensive hydrogen bonding involving the water of solvation.

https://doi.org/10.1071/CH9921021

© CSIRO 1992

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