FourN-(4-halophenyl)-4-oxo-4H-chromene-3-carboxamides (halo = F, Cl, Br and I),N-(4-fluorophenyl)-4-oxo-4H-chromene-3-carboxamide, C₁₆H₁₀FNO₃,N-(4-chlorophenyl)-4-oxo-4H-chromene-3-carboxamide, C₁₆H₁₀ClNO₃,N-(4-bromophenyl)-4-oxo-4H-chromene-3-carboxamide, C₁₆H₁₀BrNO₃,N-(4-iodophenyl)-4-oxo-4H-chromene-3-carboxamide, C₁₆H₁₀INO₃, have been structurally characterized. The molecules are essentially planar and each exhibits ananticonformation with respect to the C—N rotamer of the amide and acisgeometry with respect to the relative positions of the C_arom—C_arombond of the chromone ring and the carbonyl group of the amide. The structures each exhibit an intramolecular hydrogen-bonding network comprising an N—H...O hydrogen bond between the amide N atom and the O atom of the carbonyl group of the pyrone ring, forming anS(6) ring, and a weak C_arom—H...O interaction with the O atom of the carbonyl group of the amide as acceptor, which forms anotherS(6) ring. All four compounds have the same supramolecular structure, consisting ofR₂²(13) rings that are propagated along thea-axis direction by unit translation. There is π–π stacking involving inversion-related molecules in each structure.