Some thio­ether-ketones and their related derivatives

Abstract

Structures are reported for two thio­ether-ketones, and for some derived hydrazones, and instances of conformational enanti­omerism are delineated. Various types of hydrogen bonds, such as weak C—H⋯S and stronger N—H⋯N and N—H⋯S hydrogen bridges are noted, and inter­molecular cases examined via DFT calculations.

Structural characteristics are reported for two thio­ether–ketones, Dtdpe and Mtdp [2-({2-[(2-oxo-2-phenyl­eth­yl)sulfan­yl]eth­yl}sulfan­yl)-1-phenyl­ethan-1-one, C₁₈H₁₈O₂S₂, and 2-[(2-oxo-2-phenyl­eth­yl)sulfan­yl]-1-phenyl­ethan-1-one, C₁₆H₁₄O₂S], and for related derivatives, the bis­(pyridyl­hydrazones) Dhpk and Prpsb [2-((2E)-2-{(2Z)-2-phenyl-2-[2-(pyridin-2-yl)hydrazin-1-yl­idene]ethyl­idene}hydrazin-1-yl)pyridine, C₁₈H₁₆N₆, and 2-[(2Z,12Z)-3,12-diphenyl-14-(pyridin-2-yl)-5,10-di­thia-1,2,13,14-tetra­aza­tetra­deca-2,12-dien-1-yl]pyridine, C₃₀H₃₂N₆S₂], as well as for the macrocyclic thio­carbohydrazide derivative Ctrsp[(3E,8Z)-3,9-dimethyl-1,11-di­thia-4,5,7,8-tetra­aza­cyclo­tetra­deca-3,8-diene-6-thione, C₁₀H₁₈N₄S₃]. Three of the five compounds exhibit conformational enanti­omerism in the solid state. The occurrence of intra- and inter­molecular hydrogen bonding is commented upon through quantum mechanical (DFT) calculations. Weak C—H⋯S inter­actions are noted, while stronger N—H⋯N and N—H⋯S hydrogen bridges are delineated.