Organic fluorine (C–F⋯F–C) mediated intermolecular interactions in (E)-3-(2,6-difluorophenyl)-1-(4-nitrophenyl)prop‑2-en-1-one: An intuition from an experimental and computational studies

• Structural investigation of chalcone derivative using crystal X-ray diffraction technique. • C H…O, C F…F C, and C H…H C interactions are studied. • MEP analysis helped to understand the physical properties of the molecule. • The nature of non-covalent bonding characteristics were revealed by the NCI analysis. The importance of fluorine-mediated weak intermolecular interactions in crystal lattices has been disputed for decades. Controversies have arisen from structural, computational, and theoretical insights about these interactions. To highlight the importance of "organic fluorine" in crystal structure, experimental and theoretical investigations were conducted in (E)-3-(2,6-difluorophenyl)-1-(4-nitrophenyl)prop‑2-en-1-one (F2) and compared with the similar chalcone derivative (E)-1-(4-Nitrophenyl)-3-phenylprop-2-en-1-one ( F3 ). The structure of the synthesized compound was confirmed through using single-crystal X-ray diffraction study. These results indicate that both the compounds F2 and F3 crystallizes in the monoclinic crystal system with different space group. The crystal structure of F2 is mainly stabilized by a combination of intermolecular interactions such as weak hydrogen bonds like C H⋯O, C15–F1⋯F3–C19 and π⋅⋅⋅π stacking, whereas in F3 , C H⋯O and C H⋯H C, π⋅⋅⋅π stacking interactions are involved. We confirmed the presence of intermolecular interactions using Hirshfeld surface analysis and two-dimensional fingerprint plots. Additionally, computational tools like QTAIM and NCI plot index analysis were used to assess the strength and type of intermolecular interactions. Molecular docking analysis was performed in order to investigate the potency of both the compounds ( F2 and F3 ) against the breast cancer.