[:pb]Expected and unexpected products of reactions of 2-hydrazinylbenzothiazole with 3-nitrobenzenesulfonyl chloride in different solventes[:]

[:pb]Authors: Morscher, A.; De Souza, M. V. N.; Wardell, J. L.; Harrison, W. T. A.
Source: Acta Crystallographica Section e, Crystallographic Communications, v. 74, p. 673-677, 2018
Publisher: Science Direct

Abstract

The syntheses and crystal structures of 2-[2-(propan-2-yl­idene)hydrazin­yl]-1,3-benzo­thia­zol-3-ium 3-nitro­benzene­sulfonate (C₁₀H₁₂N₂S⁺·C₆H₄NO₅S⁻), (I), 2-[2-(3-nitro­benzene­sulfon­yl)hydrazin­yl]-1,3-benzo­thia­zole (C₁₃H₁₀N₄O₄S₂), (II) and 2-[2-(3-nitro­benzene­sulfon­yl)hydrazin­yl]-1,3-benzo­thia­zol-3-ium 3-nitro­benzene­sulfonate (C₁₃H₁₁N₄O₄S₂⁺·C₆H₄NO₅S⁻), (III) are reported. Salt (I) arose from an unexpected reaction of 2-hydrazinylbenzo­thia­zole with the acetone solvent in the presence of 3-nitro­benzene­sulfonyl 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—HO_s (s = sulfonate) hydrogen bonds; adjacent cations inter­act by way of short π–π stacking inter­actions between the thia­zole rings [centroid–centroid separation = 3.4274 (18) Å]. In (II), which crystallizes with two neutral mol­ecules in the asymmetric unit, the mol­ecules are linked by N—HN and N—HO_n (n = nitro) hydrogen bonds to generate [1] chains, which are cross-linked by C—HO and π–π stacking inter­actions. The crystal of (III) features centrosymmetric tetra­mers (two cations and two anions) linked by cooperative N—HO hydrogen bonds; C—HO and π–π inter­actions occur between tetra­mers.

Keywords: crystal structure, hydrazinyl­benzo­thiazole, hydrogen bonds, molecular salt

Document Type: Research Article

DOI: 10.1107/S2056989018005595

Publication date: 2018

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