Diverse structural assemblies of U-shaped hydrazinyl-sulfonamides: experimental and theoretical analysis of non-covalent interactions stabilizing solid state conformations

Abstract

The present study describes the synthesis of five new hydrazinyl-sulfonamide derivatives incorporating linear and branched alkyl chains. An efficient and straightforward synthetic approach was used to achieve these sulfonamide compounds in good yields. The synthesized compounds were fully characterized by spectroscopic methods and single crystal X-ray diffraction analysis. Structural analysis of U-shaped hydrazinyl-sulfonamides reveals the presence of remarkable similarities in their crystal packing. The supramolecular architectures of these molecules were stabilized by classical hydrogen bonds and C–H⋯O interactions. Furthermore, the U-shaped conformation observed in the solid state of all the compounds has been analyzed using DFT calculations, AIM analysis and the NCI plot index. It reveals the existence of two intramolecular interactions, which are NH⋯π and unconventional π–π interactions involving the hydrazido π-system.