Volume 57, Issue 4 pp. 444-445

Two diastereomers of 9-(2,6-di­chloro­phenyl)-4a-hydroxy-3,3,6,6-tetra­methyl-1,2,3,4,4a,5,6,7,8,9a-deca­hydro­xanthene-1,8-dione in the same crystal

Michael Bolte

Michael Bolte

Institut für Organische Chemie, J. W. Goethe-Universität Frankfurt, Marie-Curie-Straße 11, 60439 Frankfurt/Main, Germany

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Alexander Degen

Alexander Degen

Institut für Organische Chemie, J. W. Goethe-Universität Frankfurt, Marie-Curie-Straße 11, 60439 Frankfurt/Main, Germany

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Stephan Rühl

Stephan Rühl

Institut für Organische Chemie, J. W. Goethe-Universität Frankfurt, Marie-Curie-Straße 11, 60439 Frankfurt/Main, Germany

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First published: 23 June 2004
Michael Bolte, e-mail: [email protected]

Abstract

The reaction of dimedone with 2,6-di­chloro­benz­aldehyde leads to the title compound, C23H26Cl2O4. In principle, the reaction could yield eight different stereoisomers. We have found four of them in the same crystal as two enantiomeric pairs of diastereomers, which means that the asymmetric unit is built up of two different diastereomers. Two of the three chiral centres display the same configuration, while the third is different in the two mol­ecules in the asymmetric unit. The packing of the mol­ecules is stabilized by hydrogen bonds between the hydroxy group and the carbonyl group attached to the cyclo­hexene ring, forming chains in which the different diastereomers alternate.

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