Crystal engineering using bisphenols. Chains, ladders and sheets formed by the adducts of 1,4-diazabicyclo[2.2.2]octane with bisphenols: Structures of adducts with 4,4'-isopropylidenediphenol(1/1), 4,4'-oxodiphenol(1/1) and 4,4'-thiodiphenol(1/1 and 2/1)

4,4'-Isopropylidenediphenol-1,4-diazabicyclo[2.2.2]octane (1/1), (1), C15H16O2.C6H12N2, monoclinic, P2/a, a = 11.385(2), b = 6.5565(12), c = 13.076(2)Angstrom, beta = 96.240(11)degrees, with Z = 2; the two components of the adduct, which each lie across twofold axes, are joined into simple chains via O-H ... N hydrogen bonds in a motif with graph set C-2(2)(17). 4,4/-Oxodiphenol-1,4-diazabicyclo[2.2.2]octane (1/1), (2), C12H10O3.C6H12N2, orthorhombic, P2(1)2(1)2(1), a = 9.4222(11), b = 11.1886(15), c = 15.694(2), with Z = 4; diamine component is the disordered by rotation about the N ... N vector, having two orientations [populations 0.76(1) and 0.24(1)] rotated by 48(3)degrees from coincidence: the components are joined into chains via O-H ... N hydrogen bonds in a motif with graph set C-2(2)(17); pairs of these chains are joined into ladders by C-H ... O hydrogen bonds in a motif of graph set R-2(2)(22). 4,4'-Thiodiphenol-1,4-diazabicyclo[2.2.2]octane (1/1), (3), C12H10O2S.C6H12N2, isomorphous, a = 9.5785 (11), b = 11.4525 (13), c = 15.759 (2) A (and ipso facto isostructural), with (2); the diamine disorder is characterized by two equally populated orientations related by a rotation about the N ... N vector of 37.1(2)degrees and pairs of chains are now joined into ladders by C-H ... S hydrogen bonds. 4,4'-Thiodiphenol-1,4-diazabicyclo[2.2.2]octane (2/1), (5), (C12H10O2S)(2) . C6H12N2, monoclinic, P2(1)/n, a = 8.3198(9), b = 11.4006(13), c = 15.056(2)A, beta = 104.955(8)degrees, with Z = 2; the diamine component of the adduct is disordered across a centre of inversion, and the bisphenol components are linked into chains by O-H ... O hydrogen bonds in a motif with graph set C(12). These chains form cross-links via the diamine component by means of O-H ... N hydrogen bonds in a C-3(3)(19) motif to yield sheets within which are large hydrogen-bonded rings described by the unusual graph set R-8(8)(62).