Mr. Caira et al., ANNULATED BICYCLO[2.2.2]OCTENONES - 9-HYDROXY-9-CHLOROMETHYL-ENDO-TRICYCLO )]UNDECA-4,10-DIENE-3-SPIRO(1'-CYCLOPROPANE)-8-ONE AND -ENDO-TRICYCLO[8.2.2.0(2,9)]TETRADECA-13-EN-11-ONE, Journal of chemical crystallography, 25(9), 1995, pp. 583-587
A single crystal X-ray diffraction study of two annulated bicyclo[2.2.
2]octenones has been carried out to establish their precise stereostru
ctures. The compounds, with their crystal data, are: 1, ]undeca-4,10-d
iene-3-spiro(1'-cyclopropane)-8-one, C14H15O2Cl, space group P2(1)/c,
a = 10.540(2), b = 9.668(1), c = 11.841(4)Angstrom, beta = 95.67(2)deg
rees, Z = 4, and 3 -chloromethyl-endotricyclo[8.2.2.0(2,9)]tetradeca-
-13-en-11-one, C15H21O2Cl, space group C2/c, a = 20.747(8), b = 6.498(
1), c = 20.525(3)Angstrom, beta = 93.04(3)degrees, Z = 8. The molecule
of 1 has endo stereochemistry at the ring junction and the spirocyclo
propane ring is proximal to the hydroxyl group. In 2, the eight member
ed ring deviates from a chair conformation and one ring atom is disord
ered. Crystals of 1 and 2 contain centrosymmetric dimers formed by C=O
... O-H hydrogen bonds.