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In the title compound, C20H22N2O3·0.25H2O, the water mol­ecule (occupancy 0.25) is disordered across a crystallographic inversion center. The dihedral angle between the hydroxy­phenyl ring and the benzimidazole ring system is 59.31 (9)°. In the crystal structure, mol­ecules are connected by inter­molecular O—H...N and C—H...O hydrogen bonds. The crystal structure is further stabilized by a weak C—H...π inter­action involving the imidazole ring.

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In the title compound, C32H26Cl2N2O3, the piperidone ring adopts a chair conformation and the proline and pyrrolidine rings adopt envelope conformations. The indane ring system is essentially planar with an r.m.s. deviation of 0.011 Å for the non-H atoms. The dihedral angle between the two chloro-substituted benzene rings is 63.69 (10)°. Intra­molecular C—H...O and N—H...O hydrogen bonds may influence the mol­ecular conformation. In the crystal structure, mol­ecules are connected into layers by weak inter­molecular C—H...O hydrogen bonds.
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