title: Transformations of griseofulvin in strong acidic conditions--crystal structures of 2'-demethylgriseofulvin and dimerized griseofulvin.
abstract: The structure of griseofulvic acid, C16H15ClO6, at 100 K has orthorhombic (P2(1)2(1)2) symmetry. It is of interest with respect to biological activity. The structure displays intermolecular O-H...O, C-H...O hydrogen bonding as well as week C-H...pi and pi...pi interactions. In strong acidic conditions the griseofulvin undergoes dimerization. The structure of dimerized griseofulvin, C34H32C12O12 x C2H6O x H2O, at 100 K has monoclinic (P2(1)) symmetry. The molecule crystallized as a solvate with one ethanol and one water molecule. The dimeric molecules form intermolecular O-H...O hydrogen bonds to solvents molecules only but they interact via week C-H...O, C-H...pi, C-Cl...pi and pi...pi interactions with other dimerized molecules.
authors.affiliation: Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka, 44/52, PL-01 224 Warszawa, Poland.
authors.forename: Barbara
authors.initials: B
authors.lastname: Leśniewska
authors.forename: Said
authors.initials: S
authors.lastname: Jebors
authors.forename: Anthony W
authors.initials: AW
authors.lastname: Coleman
authors.forename: Kinga
authors.initials: K
authors.lastname: Suwińska
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry*; D047250:Calixarenes / Q000737:chemistry; D018360:Crystallography, X-Ray; D019281:Dimerization; D006118:Griseofulvin / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D000935:Antifungal Agents; D047250:Calixarenes; D006118:Griseofulvin; C013923:4-demethylgriseofulvin