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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—H
O 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 π–π interactions between the pyrimidine rings with a centroid–centroid distance of 3.446 (2) Å.
O 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 π–π interactions between the pyrimidine rings with a centroid–centroid distance of 3.446 (2) Å.organic compoundsOpen access
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In the title compound, C15H14BrNO, the dihedral angle between the aromatic rings is 4.10 (11)° and the molecule is close to planar (r.m.s. deviation for the non-H atoms = 0.053 Å). An intramolecular O—HN hydrogen bond closes an S(6) ring. In the crystal, very weak C—Hπ interactions are observed.
N hydrogen bond closes an S(6) ring. In the crystal, very weak C—Hπ interactions are observed.
