Acta Crystallographica Section B

Structural Science

Volume 58, Part 6 (December 2002)

research papers

Acta Cryst. (2002). B58, 1057-1066 [ doi:10.1107/S0108768102015987 ]

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

I. D. H. Oswald, D. R. Allan, P. A. McGregor, W. D. S. Motherwell, S. Parsons and C. R. Pulham

Abstract: 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 OHO=C interactions [C(9) chains in graph-set notation] or NHO=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 [bold 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.

Keywords: paracetamol; hydrogen bonding.


	Structure factor file (CIF format) (171.6 kbytes) Contains datablock parody

	Structure factor file (CIF format) (133.8 kbytes) Contains datablock pardmp

	Structure factor file (CIF format) (120.1 kbytes) Contains datablock parnmm

	Structure factor file (CIF format) (113.5 kbytes) Contains datablock ppip02

	Structure factor file (CIF format) (380.0 kbytes) Contains datablock pardip

	Structure factor file (CIF format) (231.9 kbytes) Contains datablock pmor02

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