Channel-forming solvate crystals and isostructural solvent-free powder of 5-hydroxy-6-methyl-2-pyridone

Sean R. Parkin, Edward J. Behrman

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2 Scopus citations


Crystals of 5-hydroxy-6-methyl-2-pyridone, (I), grown from a variety of solvents, are invariably trigonal (space group R3̄); these are 5-hydroxy-6-methyl-2-pyridone acetone 0.1667- solvate, C 6H 7NO 2·0.1667C 3H 6O, (Ia), and 6-methyl-5-hydroxy- 2-pyridone propan-2-ol 0.1667-solvate, C 6H 7NO 2·0.1667C 3H 8O, (Ib), and the forms from methanol, (Ic), water, (Id), benzonitrile, (Ie), and benzyl alcohol, (If). They incorporate channels running the length of the c axis that contain extensively disordered solvent molecules. A solvent-free sublimed powder of 5-hydroxy-6-methyl-2-pyridone microcrystals is essentially isostructural. Inversion-related host molecules interact via pairs of N-H⋯O hydrogen bonds to form R 2 2(8) dimers. Six of these dimers form large R 12 6(42) puckered rings, in which the O atom of each N-H⋯O hydrogen bond is also the acceptor in an O-H⋯O hydrogen bond that involves the 5-hydroxy group. The large R 12 6 (42) rings straddle the 3̄ axes and form stacked columns via π-π interactions between inversion-related molecules of (I) [mean interplanar spacing = 3.254 Å and ring centroid-centroid distance = 3.688 (2) Å]. The channels are lined by methyl groups, which all point inwards to the centre of the channels.

Original languageEnglish
Pages (from-to)o324-o328
JournalActa Crystallographica Section C: Crystal Structure Communications
Issue number8
StatePublished - Aug 2011

ASJC Scopus subject areas

  • General Biochemistry, Genetics and Molecular Biology


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