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)

• Published in: Acta crystallographica. Section B, Structural science Structural science, 1997-06, Vol.53 (3), p.513-520
• Main Authors: Ferguson, G., Coupar, P. I., Glidewell, C.
• Format: Article
• Language: English
• Subjects: Condensed matter: structure, mechanical and thermal properties; Exact sciences and technology; Heterocyclic compounds; Organic compounds; Physics; Structure of solids and liquids; crystallography; Structure of specific crystalline solids
• ISSN: 0108-7681; 1600-5740
• DOI: 10.1107/S0108768196014036

4,4′-Isopropylidenediphenol-1,4-diazabicyclo[2.2.2]octane (1/1), (1), C 15 H 16 O 2 .C 6 H 12 N 2 , monoclinic, P 2/ a , a = 11.385 (2), b = 6.5565 (12), c = 13.076 (2) Å, \beta = 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 C _{2}^2(17). 4,4′-Oxodiphenol-1,4-diazabicyclo[2.2.2]octane (1/1), (2), C 12 H 10 O 3 .C 6 H 12 N 2 , orthorhombic, P 2 1 2 1 2 1 , 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 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-l,4-diazabicyclo[2.2.2]octane (1/1), (3), C 12 H 10 O 2 S.C 6 H 12 N 2 , 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), (C 12 H 10 O 2 S) 2 .C 6 H 12 N 2 , monoclinic, P 21/ n , a = 8.3198 (9), b = 11.4006 (13), c = 15.056 (2) Å, \beta = 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 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).