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A 1 : 1 co-crystal of quinol and pyridine

Oswald, I D H and Motherwell, W D S and Parsons, S (2004) A 1 : 1 co-crystal of quinol and pyridine. Acta Crystallographica Section E: Structure Reports, 60 (Part 1). O1967-O1969. ISSN 1600-5368

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A co-crystal of quinol and pyridine would be expected to form with 1:2 stoichiometry because quinol has two hydrogen-bond donors and pyridine has one hydrogen-bond acceptor which is more basic than phenolic oxygen. We report the structure of a 1:1 co-crystal, viz. quinol-pyridine (1/1), C6H6O2.C5H5N, which does not conform to this expectation. Its stability appears to imply that a combination of individually relatively weak C-H...O, C-H...pi and pi-pi stacking interactions are energetically competitive with O-H...N hydrogen bonds. Quinol molecules lie on inversion centres, while pyridine is in a general position.