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The title compound, C17H13NO3, a coumarin analog prepared from (E)-methyl 4-(4-methoxy­phenyl)-2-oxobut-3-enoate and 2-amino­phenol, has a planar conformation. Aromatic π-stacking interactions and C—H...O hydrogen bonds stabilize the crystal structure.

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The title compound, C10H14O4, is used to cure coughs and clear up phlegm and it is also used as an inter­mediate in the synthesis of other medicinal products. The entire molecule, except for atoms C10 and O4, is essentially planar (to within 0.001 Å).

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In the title compound, C21H20O3·0.5H2O, the water mol­ecule lies on a crystallographic twofold rotation axis. The cyclo­hexa­ne ring adopts a twist–boat conformation and the cyclo­hexene ring is in an envelope conformation. In the crystal structure, the mol­ecules are linked via strong O—H...O inter­molecular hydrogen bonds to form chains along the c axis.
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