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, C21H17N3O5, 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—HO and C—HO hydrogen bonds, forming fused R2 2(18), R3 4(30), R4 4(38) rings running along [101] and R3 3(37) and R3 3(15) rings along [001]. Hirshfeld analysis was undertaken to study the intermolecular contacts in the crystal, showing that the most significant contacts are HO/OH (30.5%), HC/CH (28.2%) and HH (29.0%). Two zones with positive (50.98 and 42.92 kcal mol1 ) potentials and two zones wit h negative (42.22 and 34.63 kcal mol1 ) potentials promote the N—HO 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 mol1 from the value for the molecule Apixaban, which was used as a positive control inhibitor. This suggests the title compound exhibits inhibitory activity.