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Supramolecular synthesis based on piperidone derivatives and pharmaceutically acceptable co‐formers

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The target complexes, bis{(E,E)‐3,5‐bis[4‐(diethylamino)benzylidene]‐4‐oxopiperidinium} butanedioate, 2C27H36N3O+·C4H4O4 2−, (II), and bis{(E,E)‐3,5‐bis[4‐(diethylamino)benzylidene]‐4‐oxopiperidinium} decanedioate, 2C27H36N3O+·C10H16O4 2−, (III), were obtained by solvent‐mediated crystallization of the active pharmaceutical ingredient (API) (E,E)‐3,5‐bis[4‐(diethylamino)benzylidene]‐4‐piperidone and pharmaceutically acceptable dicarboxylic (succinic and sebacic) acids from ethanol solution. They have been characterized by melting point, IR spectroscopy and single‐crystal X‐ray diffraction. For the sake of comparison, the structure of the starting API, (E,E)‐3,5‐bis[4‐(diethylamino)benzylidene]‐4‐piperidone methanol monosolvate, C27H35N3O·CH4O, (I), has also been studied. Compounds (II) and (III) represent salts containing H‐shaped centrosymmetric hydrogen‐bonded synthons, which are built from two parallel piperidinium cations and a bridging dicarboxylate dianion. In both (II) and (III), the dicarboxylate dianion resides on an inversion centre. The two cations and dianion within the H‐shaped synthon are linked by two strong intermolecular N+—H...OOC hydrogen bonds. The crystal structure of (II) includes two crystallographically independent formula units, A and B. The cation geometries of units A and B are different. The main N—C6H4—C=C—C(=O)—C=C—C6H4—N backbone of cation A has a C‐shaped conformation, while that of cation B adopts an S‐shaped conformation. The same main backbone of the cation in (III) is practically planar. In the crystal structures of both (II) and (III), intermolecular N+—H...O=C hydrogen bonds between different H‐shaped synthons further consolidate the crystal packing, forming columns in the [100] and [10] directions, respectively. Salts (II) and (III) possess increased aqueous solubility compared with the original API and thus enhance the bioavailability of the API.
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Document Type: Research Article

Publication date: April 15, 2013

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