(IUCr) Crystallography Journals Online

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Acta Cryst. (2012). E68, o2687
[ doi:10.1107/S1600536812034757 ]

2-[(E)-({4-[(4,6-Dimethylpyrimidin-2-yl)sulfamoyl]phenyl}iminio)methyl]-6-hydroxyphenolate

M. N. Tahir, A. H. Khan, M. S. Iqbal, H. A. Shad and M. Yaqub

Abstract: The title compound, C₁₉H₁₈N₄O₄S, exists as a zwitterion in the solid state, with nominal proton transfer from a phenol group to the imine N atom. The 2,3-dihydroxybenzaldehyde fragment is oriented at a dihedral angle of 35.51 (11)° to the adajacent aniline group and makes a dihedral angle of 76.99 (6)° with the 4,6-dimethylpyrimidin-2-amine group. Intramolecular O-HO and N-HO hydrogen bonds close S(5) and S(6) rings, respectively; the same O atom accepts both bonds. In the crystal, polymeric chains along [001] are formed from molecules joined end-to-end by N-HO and O-HN hydrogen bonds; these feature R₂³(6) loops. The polymeric chains are linked by C-HO interactions and there are [pi] - [pi] interactions between the pyrimidine rings with a centroid-centroid distance of 3.446 (2) Å.