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The formation of paracetamol (acetaminophen) adducts with hydrogen-bond acceptors

Oswald, I D H and Allan, D R and Motherwell, W D S and Parsons, S and Pulham, C R and McGregor, P.A. (2002) The formation of paracetamol (acetaminophen) adducts with hydrogen-bond acceptors. Acta Crystallographica Section B: Structural Science, 58 (Part 6). pp. 1057-1066. ISSN 0108-7681

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The crystal structures of five hemiadducts of paracetamol with 1,4-dioxane, N-methylmorpholine, morpholine, N,N-dimethylpiperazine and piperazine and a related 1:1 adduct of paracetamol with 4,4'-bipyridine are described. All structures are characterized by the formation of chains of paracetamol molecules, which are linked via either OH...O==C interactions [C(9) chains in graph-set notation] or NH...O==C interactions [C(4) chains], depending on the presence or absence of substituent groups on the guest molecule. In all cases except for the morpholine and bipyridine adducts these chains are connected by hydrogen-bond interactions with the guest molecules, which reside on crystallographic inversion centres. In the bipyridine adduct this linkage also involves a pi-stacking interaction; in the morpholine adduct it is formed between the OH groups of two opposed paracetamol molecules. Most adducts ( that with 4,4'-bipyridine is an exception) decompose on heating to give monoclinic paracetamol. This is the first systematic study of a series of co-crystals containing paracetamol.