Synthesis and crystal structure of ((E)-{2-[(E)-(4-hydroxynaphthalen-1-yl)methylidene]hydrazin-1-yl}(methylsulfanyl)methylidene)azanium hydrogen sulfate monohydrate

Abstract

In the title hydrated molecular salt, C13H14N3S+·HSO4−·H2O, the protonation of the azomethine N atom in sulfuric acid medium involves the formation of the bisulfate anion. The molecular structure of the cation is obtained from the thiol tautomer of thiosemicarbazone wherein the naphthalene moiety and the conjugation of the bonds contribute to the planarity of the molecular skeleton. In the crystal, the cation, anion and water molecule 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 interactions present involving symmetry-related naphthalene rings.

Keywords

• crystal structure
• thiosemicarbazone
• synthesis
• hydrogen bonding