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The title compound, C16H15ClN2O4, contains a chiral centre and crystallizes as a racemate. The methyl­ene group β-positioned to the carbonyl group is partially (21%) disordered. It flips to the opposite sides of the corresponding six-membered carbocycle by −0.304 (3) and 0.197 (11) Å, producing alternative envelope conformations. The planes of the pyran and chloro­phenyl rings form a dihedral angle of 86.25 (9)°. The mol­ecular structure is characterized by an intra­molecular N—H...O inter­action, which generates an S(6) ring motif. The corresponding amino N atom deviates from the plane of the pyran ring by 0.1634 (19) Å. In the crystal, mol­ecules are linked via C—H...O hydrogen bonds, forming C(8) chains running parallel to the b-axis direction. The crystal structure also features C—H...π inter­actions.

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In the title compound, C19H14N2O5, the spiro junction links an oxindole moeity and a furan ring, which subtend a dihedral angle of 83.49 (6)°. The mol­ecular structure features an N—H...O hydrogen bond, which generates an S(6) ring motif. The crystal packing is governed by two N—H...O inter­actions, one of which generates a centrosymmetric R22(14) dimer. The other N—H...O inter­action along with a C—H...O hydrogen bond contributes to the formation of a C22[R22(9)] dimeric chain running along the b-axis direction.
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