Unusual synthesis and crystal structure of 4-tricyclanol

Here we report the synthesis of 4-tricyclanol, 6, via an unusual route and its characterisation, by single crystal X-ray diffraction studies. The crystal structure of 6 shows extended hydrophobic channels and catenated hydrogen bonding. Both of these structural features are, to our knowledge, unique in multicyclic cage alcohols. The structures of similar compounds such as 1-adamantanol and cis-verbinol are based on small aggregate hydrogen-bonded clusters. We propose that the catenated hydrogen-bonded structure of the crystal phase of the title compound leads to the unusual morphology of the crystalline sample. Whereas crystals of other multicyclic cage alcohols are typically cuboid in shape, those of 4-tricyclanol, are very long (20–30 mm) needles with flat rectangular cross-sections (1–2×0.3 mm). The long axis of these crystals extends in the direction of the catenated hydrogen bonding.