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) Å, = 96.240 (11)°, 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 C₂²(17). 4,4'-Oxodiphenol-1,4-diazabicyclo[2.2.2]octane (1/1), (2), C₁₂H₁₀O₃.C₆H₁₂N₂, orthorhombic, P2₁2₁2₁, a = 9.4222 (11), b = 11.1886 (15), c = 15.694 (2), with Z = 4; the diamine component is disordered by rotation about the N...N vector, having two orientations [populations 0.76 (1) and 0.24 (1)] rotated by 48 (3)° from coincidence: the components are joined into chains via O-H...N hydrogen bonds in a motif with graph set C₂²(17); pairs of these chains are joined into ladders by C-H...O hydrogen bonds in a motif of graph set R₂²(22). 4,4'-Thiodiphenol-l,4-diazabicyclo[2.2.2]octane (1/1), (3), C₁₂H₁₀O₂S.C₆H₁₂N₂, isomorphous, a = 9.5785 (11), b = 11.4525 (13), c = 15.759 (2) Å (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)° 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, P21/n, a = 8.3198 (9), b = 11.4006 (13), c = 15.056 (2) Å, = 104.955 (8)°, 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 C₃³(19) motif to yield sheets within which are large hydrogen-bonded rings described by the unusual graph set R₈⁸(62).

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