Abstract
The syntheses and crystal structures of 2-[2-(propan-2-yl-idene)hydrazin-yl]-1,3-benzo-thia-zol-3-ium 3-nitro-benzene-sulfonate (C(10)H(12)N(2)S(+)·C(6)H(4)NO(5)S(-)), (I), 2-[2-(3-nitro-benzene-sulfon-yl)hydrazin-yl]-1,3-benzo-thia-zole (C(13)H(10)N(4)O(4)S(2)), (II) and 2-[2-(3-nitro-benzene-sulfon-yl)hydrazin-yl]-1,3-benzo-thia-zol-3-ium 3-nitro-benzene-sulfonate (C(13)H(11)N(4)O(4)S(2)(+)·C(6)H(4)NO(5)S(-)), (III) are reported. Salt (I) arose from an unexpected reaction of 2-hydrazinylbenzo-thia-zole with the acetone solvent in the presence of 3-nitro-benzene-sulfonyl chloride, whereas (II) and (III) were recovered from the equivalent reaction carried out in methanol. The crystal of (I) features ion pairs linked by pairs of N-H⋯O(s) (s = sulfonate) hydrogen bonds; adjacent cations inter-act by way of short π-π stacking inter-actions between the thia-zole rings [centroid-centroid separation = 3.4274 (18) Å]. In (II), which crystallizes with two neutral mol-ecules in the asymmetric unit, the mol-ecules are linked by N-H⋯N and N-H⋯O(n) (n = nitro) hydrogen bonds to generate [[Formula: see text]1[Formula: see text]] chains, which are cross-linked by C-H⋯O and π-π stacking inter-actions. The crystal of (III) features centrosymmetric tetra-mers (two cations and two anions) linked by cooperative N-H⋯O hydrogen bonds; C-H⋯O and π-π inter-actions occur between tetra-mers.