The syntheses and crystal structures of exo-2,exo-6-dihydroxybicyclo[3.3.1]nonane and exo-2,exo-6-dihydroxy-2,6-diethylbicyclo[3.3.1]nonane which do not contain the host helical canals of crystalline exo-2,exo-6-dihydroxy-2,6-dimethylbicyclo[3.3.1]nonane

Abstract

In an attempt to modify the dimensions of the hydrogen-bonded helical canal host structure of crystalline exo-2,exo-6-dihydroxy-2,6-dimethylbicyclo[3.3.1]nonane (2), the title compounds which involve a minor substituent change at the 2,6 positions were synthesised. Crystals of exo-2,exo-6-dihydroxybicyclo[3.3.1]nonane (1) and exo-2,exo-6-dihydroxy-2,6-diethylbicyclo[3.3.1]nonane (3) represent two fully hydrogen-bonded structure types distinctly different from the canal structure of (2) and from each other. Stereochemical analysis has not revealed any significant correlation of crystal structure with molecular structure in these compounds: crystal data, (1)P2₁/c, a 1 297.0(2), b 1 359.1 (2), c 1 115.0(2) pm, β 118.68(2)°, Z 8(×C₉H₁₆O₂), R 0.046 (3 049 data); (3)Fdd2, a 1 275.6(2), b 1 666.1(2), c 2 326.6(3) pm, Z 16(× C₁₃H₂₄O₂), R 0.050 (1 083 data).