The novel benzamide derivative NNN pincer type, N,N′-(azanediylbis(2,1-phenylene))bis(3-chlorobenzamide) (H3L), was synthesized from bis(2-nitrophenyl)amine starting material. The pincer ligand was characterized by 1H NMR, 13C NMR, COSY, HMQC, and FT-IR techniques. The geometry of pincer ligand was also confirmed by a single-crystal X-ray diffraction anal. Structural anal. demonstrate that H3L is monoclinic and space group P21/n with Z = 4. It was find out the mol. conformation of the structure is promoted by intramol. (N-H···O, N-H···N, and C-H···O) and intermol. (N(2)-H(2)···O(2)i, symmetry code (i) = 1/2 + x, 3/2-y, 1/2 + z) hydrogen bonds. The theor. study of H3L was performed in the gaseous phase by B3LYP/6-311G(d,p) method to determine the structural properties of the title mol., as a consequence the obtained data showed that the considerable agreement between the exptl. and theor. results. The reactivity and stability of the mol. were evaluated by calculating the HOMO-LUMO energy gap which was found as 6.5163 eV. In addition, FMO, NBO, NLO, DOS, RDG, MEP surface, and Mulliken at. charge analyses were carried out. Hirshfeld surface anal. and two-dimensional fingerprint plots were investigated and the obtained data exposed that the most significant contributions to the crystal packing are from C···H/H···C (33.2%), H···H (31.5%), and H···Cl/Cl··H (18.9%) contacts. Furthermore, the mol. docking studies were performed to reveal the binding affinity between the title compound and the main protease (6LU7) of COVID-19 coronavirus.