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Geraniin, c41H2s027 X 7H20,the main tannin from Geranium thunbergii Sieb. et Zucc. is one of the most popular folk medicines and also an official antidianhetic in Japan. Conventional Xray diffractometer data at room temperature and room and]ow temperature (120K) synchrotron data (bean1line X l 1 at EMBL! DESY Hamburg with a MARRESEARCH imaging plate) were measured. The structure could not be detennined with any of the currently distributed direct methods programs but was easily solved with DIRDIF using several conformers of the hexahydroxydiphenoyl group as input fragment into a vector search. Thus a 20 atom fragment was sufficient to solve this 75 (non H)atoms problem. A molecular structure was established where a cyclohexenetrione moiety attached to 0-4 of a central glucose unit was in a hydrated six-membered hemiacetal-ring strllcture as expected from a solid state NMR study. Due to the high oligocyclic substitution the glucopyranosyl ring is in the unusual JC4 conformation. Refinement of the low temperature synchrotron data allowed the identification of almost all hydrogens even at the seven water molecules so that a rather complex system of about thirty different hydrogen bonds can be studied in some details.

Crystal structure of the tannin geraniin based on conventional X-ray and on synchrotron data