Expected and unexpected products of reactions of 2-hydrazinylbenzo-thia-zole with 3-nitro-benzene-sulfonyl chloride in different solvents

Acta Crystallographica. Section E, Crystallographic Communications
Alexandra MorscherWilliam T A Harrison

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 (C10H12N2S+·C6H4NO5S-), (I), 2-[2-(3-nitro-benzene-sulfon-yl)hydrazin-yl]-1,3-benzo-thia-zole (C13H10N4O4S2), (II) and 2-[2-(3-nitro-benzene-sulfon-yl)hydrazin-yl]-1,3-benzo-thia-zol-3-ium 3-nitro-benzene-sulfonate (C13H11N4O4S2+·C6H4NO5S-), (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⋯Os (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⋯On (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) linke...Continue Reading

References

Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Aug 13, 2011·Acta Crystallographica. Section E, Structure Reports Online·Xu-Feng LiuShao-Liang Jiang
Mar 14, 2012·Acta Crystallographica. Section E, Structure Reports Online·Hoong-Kun FunB Narayana
Aug 21, 2012·Acta Crystallographica. Section E, Structure Reports Online·Hoong-Kun FunB Narayana
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Apr 7, 2016·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Colin R GroomSuzanna C Ward

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Citations

Jun 5, 2019·Acta Crystallographica. Section E, Crystallographic Communications·Thomas C BaddeleyEdward R T Tiekink
Nov 18, 2018·Acta Crystallographica. Section E, Crystallographic Communications·Nikhila PaiB Thimme Gowda

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