1-{[(E)-(4-{[(2Z)-2,3-Dihydro-1,3-thiazol-2-ylidene]sulfamoyl}phenyl)iminiumyl]methyl}naphthalen-2-olate

Abstract

In the title zwitterionic compound, C20H15N3O3S2, the 2-hydroxynaphthalene-1-carbaldehyde group A, the anilinic unit B and the 1,3-thiazol-2(3H)-imine group C are each approximately planar with r.m.s. deviation of 0.0721, 0.0412 and 0.0125 Å, respectively. The dihedral angles between A/B, A/C and B/C are 24.70 (10), 79.97 (7) and 83.14 (6)°, respectively. There is an intramolecular S(6) motif involving the imine N—H and the naphtholate O atom. In the crystal, inversion-related molecules form dimers as a result of N—H...N and N—H...O hydrogen bonds with R22(8) and R12(4) motifs, respectively. Weak π–π interactions between the benzene and naphthyl rings of inversion-related molecules have ring centroid–centroid distances of 3.638 (2) and 4.041 (2) Å. A C—H...π interaction occurs between the thiazol ring and the benzene ring of an adjacent molecule.

Keywords

• crystal structure
• zwitterionic compound
• sulfathiazole
• hydrogen bonding
• C—H...π interactions
• π–π interactions