Helical self-assembly of 2-(1,4,7,10-tetraazacyclododecan-1-yl)cyclohexan-1-ol (cycyclen).

The title macrocyclic amino alcohol compound, C(14)H(30)N(4)O, is investigated as a solid-state synthon for the design of a self-assembled tubular structure. It crystallizes in a helical column constructed by stereospecific O-H···N and N-H···N interactions. The hydrogen-bonding interactions, dependent upon macrocyclic ring helicity and molecular conformation, link R,R and S,S enantiomers in a head-to-tail fashion, forming a continuous hydrophilic inner core.