Singh, Daljeet (57214416779); Praveena, P. (57211537258); Sarojini, B. K. (6602477214); Shah, K. K.Muhammed (59902720000); Chopra, Deepak (7006211842); Kant, R. (7004850636)Daljeet (57214416779); Praveena, P. (57211537258); Sarojini, B. K. (6602477214); Shah, K. K.Muhammed (59902720000); Chopra, Deepak (7006211842); Kant, R. (7004850636)Singh2026-02-052026-02-052026https://dx.doi.org/10.1016/j.molstruc.2025.144392https://www.scopus.com/pages/publications/105019072062https://gnanaganga.alliance.edu.in/handle/123456789/9260A hybrid heterocyclic compound, 5-(anthracen-10-yl)-1-phenyl-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole (APTDP), has been synthesized and comprehensively characterized using spectroscopic techniques (NMR, FT-IR) and LC-MS technique. The molecular structure was confirmed by single-crystal X-ray diffraction (SCXRD) and further optimized through Density Functional Theory (DFT) and Hartree-Fock calculations. The compound APTDP crystallizes in the space group P2<inf>1</inf> and exhibits structural integrity through a cohesive network of C–H···N hydrogen bonds and stabilizing C–H···? and ?···? interactions. The crystal structure obtained from SCXRD analysis (R-factor of 0.042) shows excellent correlation with the DFT-HF optimized geometry. DFT enables advanced exploration of APTDP electronic structure by analyzing frontier molecular orbitals, atomic charge distribution, and the molecular electrostatic potential surface, these studies shows that the molecule has tendency to act as an electron acceptor with significant electrophilic character. Hirshfeld surface analysis, FP analysis, and combined QTAIM and RDG studies are performed. These approaches provide deeper insights into the structural architecture, highlighting key intra- and intermolecular interactions and shows that the weak interactions play significant role in crystal structure stabilization. In-silico docking analysis of APTDP ligand against the iNOS enzyme demonstrated strong binding affinity (-12.86 kcal/mol), suggesting that APTDP may serve as a potential iNOS inhibitor and thereby supporting its potential role in future drug development efforts. © 2025 Elsevier B.V.enDensity functional theory; Heterocyclic compound; Hirshfeld surface; Molecular docking; QTAIM; RDG; SC-XRDArticle