Synthesis and crystal structure of (E)-2-({2-[aza-niumyl-idene(methyl-sulfan-yl)meth-yl]hydrazinyl-idene}meth-yl)benzene-1,4-diol hydrogen sulfate.

Oussama Nehar,Thierry Roisnel,Samira Louhibi

doi:10.1107/s2056989019014233

Abstract

The title mol-ecular salt, C9H12N3O2S+·HSO4 -, was obtained through the protonation of the azomethine N atom in a sulfuric acid medium. The crystal com-prises two entities, a thio-semicarbazide cation and a hydrogen sulfate anion. The cation is essentially planar and is further stabilized by a strong intra-molecular O-H⋯N hydrogen bond. In the crystal, a three-dimensional network is established through O-H⋯O and N-H⋯O hydrogen bonds. A weak intermolecular C-H⋯O hydrogen bond is also observed. The hydrogen sulfate anion exhibits disorder over two sets of sites and was modelled with refined occupancies of 0.501 (6) and 0.499 (6).

Highlights

The title molecular salt, C9H12N3O2S+ÁHSO4À, was obtained through the protonation of the azomethine N atom in a sulfuric acid medium
A three-dimensional network is established through O—HÁ Á ÁO and N—HÁ Á ÁO hydrogen bonds
It is believed that the biological activity of these compounds has a strong relationship with the nature of the aldehydes and ketones from which those thiosemicarbazones were obtained (Teoh et al, 1999), and on the substituents attached at the +NH2 N atom (Beraldo & Gambino, 2004)

Summary

Chemical context

Thiosemicarbazones and their complexes are well known for their pharmacological properties, as antimicrobial (Plech et al, 2011; Pandeya et al, 1999; Kuc ̧ukguzel et al, 2006), antiinflammatory (Palaska et al, 2002) and antiumoural (de Oliveira et al, 2015) agents. It is believed that the biological activity of these compounds has a strong relationship with the nature of the aldehydes and ketones from which those thiosemicarbazones were obtained (Teoh et al, 1999), and on the substituents attached at the +NH2 N atom (Beraldo & Gambino, 2004). Thiosemicarbazones have an excellent capacity to complex transition metals, acting as chelating agents; this process usually takes place via dissociation of the acidic proton (Pal et al, 2002). The crystal structure of the title molecular salt was determined in order to investigate its biological and catalytic activities

Structural commentary

Supramolecular features

Synthesis and crystallization

Database survey

Refinement