Crystal engineering using bisphenols and trisphenols. Complexes with 1,10-phenanthroline: hydrogen-bonded chains in adducts with 4,4 '-biphenol (1/1)and 4,4 '-sulfonyldiphenol (2/3), pi-pi stacked chains in the (1/2) adductwith 4,4 '-thiodiphenol, and pairwise-interwoven nets in 1,1,1-tris(4-hydroxyphenyl)ethane-1,10-phenanthroline-methanol (1/1/1)

In 4,4'-biphenol-1,10-phenanthroline (1/1) [systematic name: 4,4'-biphenyld iol-1,10-phenanthroline (1/1)] the diphenol molecules lie across centres of inversion and the phenanthroline molecules lie across twofold rotation axe s; the phenanthroline molecules act as chain-building units and the molecul ar components are linked into steeply zigzag C(16) chains parallel to [101] by means of O-H ... N hydrogen bonds. In the structure of 4,4'-thiodipheno l-1,10-phenanthroline (1/2) the phenanthroline molecules act as chain-termi nating units; the supramolecular aggregation is finite, with the bisphenol linked to each phenanthroline molecule by means of a single O-H ... N hydro gen bond. pi-pi stacking interactions between the phenanthroline molecules in neighbouring hydrogen-bonded aggregates serve to link these aggregates i nto a continuous two-dimensional array. The phenanthroline molecules in 4,4 '-sulfonyldiphenol-1,10-phenanthroline (2/3) play two roles: molecules in g eneral positions act as chain-terminating units and are linked to the sulfo nyldiphenol molecules by means of three-centre O-H ...(N)(2) hydrogen bonds , while those lying across twofold rotation axes act as chain builders and are linked to two different sulfonyldiphenol molecules by means of a two-ce ntre O-H ... N hydrogen bond in each case; the resulting U-shaped five-comp onent aggregates are further linked by C-H ... O=S hydrogen bonds into a C- 3(3)(17)[R-2(2)(12)] 'chain of rings' along [001]. In 1,1,1-tris(4-hydroxyp henyl)ethane-1,10-phenanthroline -methanol (1/1/1) [systematic name: 4,4',4 "-ethylidynetriphenol-1, 10-phenanthroline-methanol (1/1/1)] the phenanthr oline molecules again act as chain-terminating units: the trisphenol molecu les and the methanol molecules are linked by O-H ... O hydrogen bonds into two-dimensional nets built from R-6(6)(42) rings, and pairs of these nets a re interwoven. The formation of each net utilizes two hydroxyl groups per t risphenol molecule as hydrogen-bond donors and the remaining hydroxyl group acts as donor to the phenanthroline molecule in a three-centre O-H ...(N)( 2) hydrogen bond.