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 R 2 2(8) and R 1 2(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.

A synthetic approach towards drug modification: 2-hydroxy-1-naphthaldehyde based imine-zwitterion preparation, single-crystal study, Hirshfeld surface analysis, and computational investigation

“…3a ). The inter-centroid separation ranges from 3.60 to 3.99 Å and ring off-set ranges from 0.580 to 2.098 Å. Cambridge structural database search provides two hints that have close similarity with the crystal structure of DSPIN with reference codes WUFFUA 47 and UTANAG. 48 The bond lengths and bond angles of DSPIN ( Table 2 ) are consistent with the corresponding structural parameters in the related structures.…”