Synthesis, crystal structure, Hirshfeld surface analysis, MEP study and mol­ecular docking of N-{3-[(4-meth­oxy­phen­yl)carbamo­yl]phen­yl}-3-nitro­benzamide as a promising inhibitor of hfXa

The title compound, C(21)H(17)N(3)O(5), consists of three rings, A, B and C, linked by amide bonds with the benzene rings A and C being inclined to the mean plane of the central benzene ring B by 2.99 (18) and 4.57 (18)°, respectively. In the crystal, mol­ecules are linked via N—H⋯O and C—H⋯O hydrogen bonds, forming fused R (2) (2)(18), R (3) (4)(30), R (4) (4)(38) rings running along [[Image: see text]0[Image: see text]] and R (3) (3)(37) and R (3) (3)(15) rings along [001]. Hirshfeld analysis was undertaken to study the inter­molecular contacts in the crystal, showing that the most significant contacts are H⋯O/O⋯H (30.5%), H⋯C/C⋯H (28.2%) and H⋯H (29.0%). Two zones with positive (50.98 and 42.92 kcal mol(−1)) potentials and two zones with negative (−42.22 and −34.63 kcal mol(−1)) potentials promote the N—H⋯O inter­actions in the crystal. An evaluation of the mol­ecular coupling of the title compound and the protein with enzymatic properties known as human coagulation factor Xa (hfXa) showed the potential for coupling in three arrangements with a similar minimum binding energy, which differs by approximately 3 kcal mol(−1) from the value for the mol­ecule Apixaban, which was used as a positive control inhibitor. This suggests the title compound exhibits inhibitory activity.