Crystal structure, Hirshfeld surface analysis, and DFT and mol­ecular docking studies of 6-cyanona­phthalen-2-yl 4-(benz­yloxy)benzoate

Abstract

The crystal structure of the title compound is consolidated by C—H⋯O, C—H⋯π and π–π stacking inter­actions. Hirshfeld surface analysis indicates that dispersion energy makes a dominate contribution to the isosurface.

In the title compound, C₂₅H₁₇NO₃, the torsion angle associated with the phenyl benzoate group is −173.7 (2)° and that for the benz­yloxy group is −174.8 (2)° establishing an anti-type conformation. The dihedral angles between the ten-membered cyanona­phthalene ring and the aromatic ring of the phenyl benzoate and the benz­yloxy fragments are 40.70 (10) and 87.51 (11)°, respectively, whereas the dihedral angle between the aromatic phenyl benzoate and the benz­yloxy fragments is 72.30 (13)°. In the crystal, the mol­ecules are linked by weak C—H⋯O inter­actions forming S(4) chains propagating parallel to [010]. The packing is consolidated by three C—H⋯π inter­actions and two π–π stacking inter­actions between the aromatic rings of naphthalene and phenyl benzoate with centroid-to-centroid distances of 3.9698 (15) and 3.8568 (15) Å, respectively. Inter­molecular inter­actions were qu­anti­fied using Hirshfeld surface analysis. The mol­ecular structure was further optimized by density functional theory (DFT) at the B3LYP/6–311+ G(d,p) level, revealing that the energy gap between HOMO and LUMO is 3.17 eV. Mol­ecular docking studies were carried out for the title compound as a ligand and SARS-Covid-2(PDB ID:7QF0) protein as a receptor giving a binding affinity of −9.5 kcal mol⁻¹.