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The asymmetric unit of the title compound, C20H16ClN3S, contains two independent mol­ecules, A and B. In mol­ecule A, the dihedral angles between the central benzene ring and the pendant chloro­benzene and phenyl rings are 6.37 (15) and 64.79 (15)°, respectively. The corresponding values in mol­ecule B are 28.21 (14) and 82.11 (16)°, respectively. Each mol­ecule features an intra­molecular N—H...N hydrogen bond, which generates an S(5) ring. In the crystal, mol­ecules A and B form dimers, being linked by two N—H...S hydrogen bonds with graph-set notation R22(8).

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The title compound, C10H11I2NO, was prepared by the reaction of 3,5-diiodo­salicyl­aldehyde with propyl­amine in ethanol. The mol­ecule adopts an E conformation with respect to the C=N bond and the aromatic ring. The aromatic ring and the imino unit are close to being coplanar, with a dihedral angle of 2.6 (3)° between their planes. This planarity is assisted by the formation of an intra­molecular O—H...O hydrogen bond.
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