Structure directing interactions in the crystals of o-hydroxyaryl/naphthyl derived aldimines: X-ray structure, Hirshfeld surface analysis, DFT and Molecular docking studies

We have synthesized and thoroughly analyzed many intermolecular interactions interactions present in (E)-1-(((3-nitrophenyl)amino)methylene)naphthalen-2(1H)-one (a), (E)-5-(diethylamino)-2-(((3-nitrophenyl)imino)methyl)phenol(b) and (E)-2-(((3-nitrophenyl)imino)methyl)phenol (c). Compounds a (keto-amine tautomeric form) and b, which have one molecule in the asymmetric unit, crystallize in the monoclinic crystal system with space groups P21/n and C2/c, respectively. Compound C, on the other hand, crystallizes in an orthorhombic crystal structure with the space group Pca21. The structural analysis showed that the construction of ring motifs to stabilize the crystal packing involves several interactions, including pi stacking interactions, N-H…O, and C-H…O interactions. Hirshfeld surface analysis has been used to examine their solid-state structures, including the evaluation of several energy frameworks. The results show that hydrogen bonds play a major role in the formation of the molecular sheets, and that electrostatic energy contribution dominates stability. Using fingerprint plots, it was possible to examine the variations and commonalities in the target compounds' relative contributions from noncovalent interactions. In addition, B3LYP hybrid functional with 6- 311G (d, p) level basis set was used in the density functional theory computations to optimize the structural coordinates. Through the examination of the molecular electrostatic potential surface, the chemically active areas of the target imine molecules were located. Additionally, using the internal ribosome entry site of the Hepatitis C virus ED42 (PDB-ID 3T4B), molecular docking of the title compounds was performed based on PASS analysis and literature findings.