Intermolecular interactions in the crystal structures of potential HIV-1 integrase inhibitors

2-[(2,5-dichloro-4-nitro-phenylamino)-methoxy-methyl]-8-hydroxy-quinoline 1 and 2-methyl-quinoline-5,8-dione-5-oxime 2 were obtained as potential HIV-1 integrase inhibitors. They were synthesized and analyzed by X-ray crystallography. Semiempirical theoretical calculations of energy preferred conformations were also carried out. The crystal structures of both compounds are stabilized via hydrogen bonds and π-π stacking interactions. The planarity of compound 1 is caused by intramolecular hydrogen bonds.