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

Abstract

The title compound, C19H18N4O 4S, exists as a zwitterion in the solid state, with nominal proton transfer from a phenol group to the imine N atom. The 2,3-dihydroxy-benzaldehyde 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-dimethyl-pyrimidin-2-amine group. intramolecular O - H⋯O and N - H⋯O 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 - H⋯O and O - H⋯N hydrogen bonds; these feature R23(6) loops. The polymeric chains are linked by C - H⋯O interactions and there are π-π interactions between the pyrimidine rings with a centroid-centroid distance of 3.446 (2) Å.