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Abstract
The structure of the title salt, C5H6NO(+)·C9H5O6 (-), (I), shows that 4-hy-droxy-pyridine has abstracted an H atom from benzene-1,3,5-tri-carb-oxy-lic acid, yielding a pyridinium cation and carboxyl-ate anion. The two ions form an extensive three-dimensional hydrogen-bonded network throughout the crystal. The hydrogen bonds that comprise the core of the network are considered strong, with O-H⋯O and N-H⋯O donor-to-acceptor distances ranging from 2.533 (2) to 2.700 (2) Å. Packing is further enhanced by π-stacking of the cations and anions with like species [centroid-centroid distance = 3.6206 (13) Å].
Highlights
The structure of the title salt, C5H6NO+C9H5O6, (I), shows that 4-hydroxypyridine has abstracted an H atom from benzene-1,3,5-tricarboxylic acid, yielding a pyridinium cation and carboxylate anion
As a study in crystal engineering utilizing hydrogen bonding between disparate molecules (Desiraju, 2003), we have been investigating the cocrystallization of various pyridine compounds with benzene carboxylic acids (Staun & Oliver, 2012)
We were surprised to find that in the case of 4-hydroxypyridin-1-ium 3,5-dicarboxybenzoate, (I), an H atom is abstracted from one carboxylic acid group, yielding a pyridinium salt
Summary
As a study in crystal engineering utilizing hydrogen bonding between disparate molecules (Desiraju, 2003), we have been investigating the cocrystallization of various pyridine compounds with benzene carboxylic acids (Staun & Oliver, 2012). We were surprised to find that in the case of 4-hydroxypyridin-1-ium 3,5-dicarboxybenzoate, (I), an H atom is abstracted from one carboxylic acid group, yielding a pyridinium salt. This result allows for the hydroxy O and pyridine N atom to both act as hydrogen-bond donors, rather than the donor/acceptor situation of the 4pyridone species. These two molecules have been incorporated as linker species in metal–organic frameworks (Guo et al, 2011)
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Schedule a callMore From: Acta crystallographica. Section E, Crystallographic communications
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