Abstract
•Tetrazolyl tryptophol hybrid achieved through a multistep synthetic approach.•Investigation of H-bonding networks and π–stacking interactions.•An insight into intermolecular interactions using Hirshfeld surface analysis.•Crystal voids analysis and intermolecular interaction energy frameworks.•DFT calculations focusing on the H-bonds and π–π interactions.
The present study reports the synthesis of a new nitrogen rich hybrid compound namely tetrazolyl tryptophol 6 achieved through a multistep synthetic approach. The structure of the target tetrazole-indole hybrid was established using FTIR, 1H- and 13C NMR, HRMS, and X-ray diffraction data. Investigation of solid state architectures in tetrazolyl tryptophol revealed that an intramolecular N5-H5N…N4 hydrogen bond links the 5-membered ring of the indole to the tetrazole ring. O1-H1O…N3 and N1-H1N…O1 hydrogen bonds and π…π contacts also emerged as crucial contributors in the formation of supramolecular topology of tetrazole-indole hybrid. Numerous centroid to centroid contacts involving the aromatic rings of both the indole ring system and the tetrazole ring link adjacent molecules in an obverse face-to-face fashion. Hirshfeld surface analysis further revealed the prevailing significance of π…π and H-bonding contacts. The mechanical stability of the crystal packing through crystal voids analysis and intermolecular interaction energies were also calculated. Finally, DFT calculations were performed to evaluate the hydrogen bonding and π…π stacking contacts with their rationalization and characterization using MEP surfaces, QTAIM and NCIPlot analysis.
Combined QTAIM and NCIplot analyses of an H-bonded trimer (a) and self-assembled dimer (b) of 6 are described. The overlap of the π-clouds as well as a weak C–H···N interaction between one CH group of 2-hydroxyethyl substituent and one N-atom of the tetrazole ring contribute to the stabilization of the system. [Display omitted]