rac-4-(4-Chloro­phen­yl)-2-methyl­amino-3-nitro-5,6,7,8-tetra­hydro-4H-chromen-5-one

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.