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 [\overline{1}0\overline{1}] 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.