Co-crystalline hydrogen bonded solids formed by helical tubuland diols

The helical tubulands are a group of alicyclic dialcohols whose inclusion compounds crystallise in the chiral space group P3(1)21 ( or enantiomorph P3(2)21) with a hydrogen bonded network structure containing parallel guest- filled tubes. Protic organic guest molecules are also included within these host tubes, with the exception of phenols which form co- crystalline adducts. The diol 3 includes non- protic guests within the usual tubular lattice, but forms a 1 : 1 adduct with hydroquinone in space group C2/ c whose crystal structure is entirely different from typical diol - phenol compounds like ( 2)(2).( hydroquinone) in space group P2(1)/ c. Unexpectedly, diol 3 also forms the unprecedented co- crystalline diol - alcohol compound ( 3).( methanol). This substance does have close structural similarities to the earlier co- crystalline diol - phenol compounds in space group P2(1)/ c.