Synthesis, Structural Investigation and Hirshfeld Surface Analyses of Two Imidazolinone Based Heterocyclic Compounds

Two derivatives of imidazolinones, specifically DMPI {(4Z)-4-(4-(dimethylamino)benzylidene)-2-methyl-1,4-dihydro-5H-imidazolin-5-one} and MMPI {(4Z)-4-(4-methoxybenzylidene)-2-methyl-1-((pyridin-3-yl)methyl)-1,4-dihydro-5H-imidazolin-5-one} are reported which were synthesized under reflux conditions. Both the ligands are characterized with different analytical techniques including NMR spectroscopy, mass spectrometry, IR Spectroscopy. The subsequent elucidation of their solid-state structures was achieved through the single crystal X-ray diffraction method, providing detailed insights into their molecular arrangements. In the crystalline lattice, the asymmetric unit of DMPI comprises a solitary DMPI molecule, whereas MMPI reveals a more intricate arrangement with four molecules within its asymmetric unit. Various types of supramolecular interactions such as C–H⋯O, C–H⋯N, C–H⋯π and π⋯π interactions are observed in the X-ray structures where a trifurcated C–H⋯O bonds are also observed in both the ligands. All these interactions guide the formation of 3D supramolecular architecture in the solid-state of both compounds. Besides these, the 2D fingerprint and Hirshfeld surface analysis computations were served to prove and quantify various supramolecular interactions within the crystal lattice.