Acta Crystallographica Section C

Crystal Structure Communications

Volume 65, Part 6 (June 2009)

organic compounds

gd3286 scheme

Acta Cryst. (2009). C65, o273-o277 [ doi:10.1107/S010827010901525X ]

Hydrogen-bonded structures of the isomeric 2-, 3- and 4-carbamoylpyridinium hydrogen chloranilates

K. Gotoh, H. Nagoshi and H. Ishida

Abstract: In the three isomeric salts, all C₆H₇N₂O⁺·C₆HCl₂O₄^-, of chloranilic acid (2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with 2-, 3- and 4-carbamoylpyridine, namely, 2-carbamoylpyridinium hydrogen chloranilate (systematic name: 2-carbamoylpyridinium 2,5-dichloro-4-hydroxy-3,6-dioxocyclohexa-1,4-dienolate), (I), 3-carbamoylpyridinium hydrogen chloranilate, (II), and 4-carbamoylpyridinium hydrogen chloranilate, (III), acid-base interactions involving H-atom transfer are observed. The shortest interactions between the cation and the anion in (I) and (II) are pyridinium N-H(O,O) bifurcated hydrogen bonds, which act as the primary intermolecular interaction in each crystal structure. In (III), an amide N-H(O,O) bifurcated hydrogen bond, which is much weaker than the bifurcated hydrogen bonds in (I) and (II), connects the cation and the anion.

Formula: Three isomers of C₆H₇N₂O⁺·C₆HCl₂O₄^-


	Structure factor file (CIF format) (176.3 kbytes) [ doi:10.1107/S010827010901525X/gd3286Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (156.5 kbytes) [ doi:10.1107/S010827010901525X/gd3286IIsup3.hkl ] Contains datablock II

	Structure factor file (CIF format) (156.3 kbytes) [ doi:10.1107/S010827010901525X/gd3286IIIsup4.hkl ] Contains datablock III

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