Synthesis and crystal structure of ((E)-{2-[(E)-(4-hy-droxynaphthalen-1-yl)methyl-idene]hydrazin-1-yl}(methyl-sulfan-yl)methyl-idene)azanium hydrogen sulfate monohydrate

Acta Crystallogr E Crystallogr Commun. 2016 Aug 26;72(Pt 9):1326-1329. doi: 10.1107/S2056989016013232. eCollection 2016 Sep 1.

Abstract

In the title hydrated mol-ecular salt, C13H14N3S+·HSO4-·H2O, the protonation of the azomethine N atom in sulfuric acid medium involves the formation of the bis-ulfate anion. The mol-ecular structure of the cation is obtained from the thiol tautomer of thio-semicarbazone wherein the naphthalene moiety and the conjugation of the bonds contribute to the planarity of the mol-ecular skeleton. In the crystal, the cation, anion and water mol-ecule of crystallization are linked by a series of O-H⋯O and N-H⋯O hydrogen bonds, forming a three-dimensional network. Within this network, there are also C-H⋯π inter-actions present involving symmetry-related naphthalene rings.

Keywords: crystal structure; hydrogen bonding; synthesis; thio­semicarbazone.