Crystal structure, Hirshfeld surface analysis, and DFT and mol-ecular docking studies of 6-cyanona-phthalen-2-yl 4-(benz-yloxy)benzoate

Abstract

In the title compound, C₂₅H₁₇NO₃, the torsion angle associated with the phenyl benzoate group is -173.7 (2)° and that for the benz-yloxy group is -174.8 (2)° establishing an anti-type conformation. The dihedral angles between the ten-membered cyanona-phthalene ring and the aromatic ring of the phenyl benzoate and the benz-yloxy fragments are 40.70 (10) and 87.51 (11)°, respectively, whereas the dihedral angle between the aromatic phenyl benzoate and the benz-yloxy fragments is 72.30 (13)°. In the crystal, the mol-ecules are linked by weak C-H⋯O inter-actions forming S(4) chains propagating parallel to [010]. The packing is consolidated by three C-H⋯π inter-actions and two π-π stacking inter-actions between the aromatic rings of naphthalene and phenyl benzoate with centroid-to-centroid distances of 3.9698 (15) and 3.8568 (15) Å, respectively. Inter-molecular inter-actions were qu-anti-fied using Hirshfeld surface analysis. The mol-ecular 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. Mol-ecular 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.

Keywords: 4-(benz­yloxy)benzoate; DFT; Hirshfeld surface; crystal structure; cyanona­pthalene and mol­ecular docking; inter­molecular inter­actions.

Figure 1

The mol­ecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.

Figure 2

The mol­ecular packing of (I) with C—H ⋯π inter­actions depicted by dashed lines.

Figure 3

The mol­ecular packing of (I) with π–π inter­actions depicted by pale-green dashed lines.

Figure 4

C—H⋯O inter­action in (I) forming an S(4) chain running parallel to [010]; symmetry code as in Table 2 ▸.

Figure 5

Hirshfeld surface of (I) plotted over d_norm; the dashed lines indicate the C—H⋯O inter­actions.

Figure 6

Two-dimensional fingerprint plots for the title compound, showing all inter­actions, and delineated into H⋯H, C⋯H/H⋯C, H⋯O/O⋯H, N⋯H/H⋯N, and C⋯C inter­actions.

Figure 7

Energy frameworks calculated for the title compound, viewed along the a axis direction, showing (a) Coulomb potential force, (b) dispersion force and (c, d) total energy diagrams. The cylindrical radii are proportional to the relative strength of the corresponding energies; they were adjusted to a cutoff value of 5 kJ mol⁻¹.

Figure 8

HOMO and LUMO of (I) with the energy band gap E_g.

Figure 9

MEP plots of the title compound; regions of attractive potential appear in red and those of repulsive potential appear in blue.

Figure 10

A three-dimensional view of the SARS-Covid-2(PDB ID:7QF0) protein and two-dimensional view of the mol­ecular inter­action between the ligand and amino acid residues.