M. Bolte et al., Two diastereomers of 9-(2,6-dichlorophenyl)-4a-hydroxy-3,3,6,6-tetra-methyl-1,2,3,4,4a,5,6,7,8,9a-deca-hydroxanthene-1,8-dione in the same crystal, ACT CRYST C, 57, 2001, pp. 444-445
The reaction of dimedone with 2,6-dichlorobenzaldehyde leads to the title c
ompound, C23H26Cl2O4. In principle, the reaction could yield eight differen
t stereoisomers. We have found four of them in the same crystal as two enan
tiomeric pairs of diastereomers, which means that the asymmetric unit is bu
ilt up of two different diastereomers. Two of the three chiral centres disp
lay the same configuration, while the third is different in the two molecul
es in the asymmetric unit. The packing of the molecules is stabilized by hy
drogen bonds between the hydroxy group and the carbonyl group attached to t
he cyclohexene ring, forming chains in which the different diastereomers al
ternate.