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The title compound, C15H10I2O, is a halogenated chalcone formed from two iodine substituted rings, one para-substituted and the other meta-substituted, linked through a prop-2-en-1-one spacer. The crystal structure shows the mol­ecules contain halogen bonds which are always between equivalent iodine atoms, either para–para or meta–meta., The title compound, C15H10I2O, is a halogenated chalcone formed from two iodine substituted rings, one para-substituted and the other meta-substituted, linked through a prop-2-en-1-one spacer. In the mol­ecule, the mean planes of the 3-iodo­phenyl and the 4-iodo­phenyl groups are twisted by 46.51 (15)°. The calculated electrostatic potential surfaces show the presence of σ-holes on both substituted iodines. In the crystal, the mol­ecules are linked through type II halogen bonds, forming a sheet structure parallel to the bc plane. Between the sheets, weak inter­molecular C—H⋯π inter­actions are observed. Hirshfeld surface analysis showed that the most significant contacts in the structure are C⋯H/H⋯C (31.9%), followed by H⋯H (21.4%), I⋯H/H⋯I (18.4%). I⋯I (14.5%) and O⋯H/H⋯O (8.1%).

In the crystal of the title compound, a supra­molecular sheet structure is formed through N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds., In the title compound, C19H19NO5, the amide carbonyl O atom is positioned anti to the other two carbonyl O atoms. The 4-hy­droxy­hydro­cinnamate fragment is disordered over two positions with an occupancy ratio of 0.729 (12):0.271 (12). The N—(C=O)—C plane of the acetamide group and the acetate O—(C=O)—C plane are almost co-planar; the acetamide plane makes dihedral angles of 1.9 (6) and 16.0 (19)°, respectively, with the acetate planes of the major and minor occupancy components. In the crystal, N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules into a supra­molecular sheet structure parallel to (102).