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In the title compound, C10H9ClN2O4, the oxazolidinone ring adopts a near-planar conformation, with mean and maximum deviations of 0.0204 (8) and 0.0328 (8) Å, respectively. The nitro group is twisted slightly from the plane of the benzene ring, making a dihedral angle of 6.79 (3)°. The dihedral angle between the mean oxazolidinone plane and the benzene ring is 56.21 (3)°. In the crystal, N—H...O hydrogen bonds and N—O...π inter­actions [O...centroid distances = 3.478 (1) and 3.238 (1) Å] dominate the packing, forming infinite zigzag chains along the b-axis direction. Neighbouring chains are linked together through C—H...O and C—H...Cl inter­actions. The absolute configuration of the two stereogenic centres was determined using the anomalous dispersion of the Cl atom.

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The title monohydrate, C9H10N2O3·H2O, contains an aziridine ring including two contiguous stereocenters, both of which exhibit an R configuration. The methyl­hydroxy and nitro­phenyl groups are cis-disposed about the aziridine ring. The mean plane of the benzene ring is tilted to the aziridine ring by 66.65 (8)°. The nitro group is nearly coplanar with the benzene ring [dihedral angle = 2.5 (2)°]. In the crystal, the components are linked by N—H...O, O—H...N and O—H...O hydrogen bonds, generating supra­molecular layers parallel to (001).
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