Coupling between 2-pyridylselenyl chloride and phenylselenocyanate: synthesis, crystal structure and non-covalent interactions

Abstract

A new pyridine-fused selenodiazolium salt, 3-(phenylselanyl)[1,2,4]selenadiazolo[4,5-a]pyridin-4-ylium chloride dichloromethane 0.352-solvate, C12H9N2Se2+·Cl−·0.352CH2Cl2, was obtained from the reaction between 2-pyridylselenenyl chloride and phenylselenocyanate. Single-crystal structural analysis revealed the presence of C—H...N, C—H...Cl−, C—H...Se hydrogen bonds as well as chalcogen–chalcogen (Se...Se) and chalcogen–halogen (Se...Cl−) interactions. Non-covalent interactions were explored by DFT calculations followed by topological analysis of the electron density distribution (QTAIM analysis). The structure consists of pairs of selenodiazolium moieties arranged in a head-to-tail fashion surrounding disordered dichloromethane molecules. The assemblies are connected by C—H...Cl− and C—H...N hydrogen bonds, forming layers, which stack along the c-axis direction connected by bifurcated Se...Cl−...H—C interactions.

Keywords

• crystal structure
• non-covalent interactions
• chalcogen heterocycles
• chalcogen bonding