Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 4 (April 2013)


organic compounds



qs3023 scheme

Acta Cryst. (2013). C69, 421-427    [ doi:10.1107/S0108270113006185 ]

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

B. Sandhu, S. Draguta, T. L. Kinnibrugh, V. N. Khrustalev and T. V. Timofeeva

Abstract: The target complexes, bis{(E,E)-3,5-bis[4-(diethylamino)benzylidene]-4-oxopiperidinium} butanedioate, 2C27H36N3O+·C4H4O42-, (II), and bis{(E,E)-3,5-bis[4-(diethylamino)benzylidene]-4-oxopiperidinium} decanedioate, 2C27H36N3O+·C10H16O42-, (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\overline 1] directions, respectively. Salts (II) and (III) possess increased aqueous solubility compared with the original API and thus enhance the bioavailability of the API.

Formula: 2C27H36N3O+·C4H4O42-, 2C27H36N3O+·C10H16O42- and C27H35N3O·CH4O


hkldisplay filedownload file

Structure factor file (CIF format) (295.6 kbytes)
[ doi:10.1107/S0108270113006185/qs3023Isup2.hkl ]
Contains datablock I


hkldisplay filedownload file

Structure factor file (CIF format) (486.7 kbytes)
[ doi:10.1107/S0108270113006185/qs3023IIsup3.hkl ]
Contains datablock II


hkldisplay filedownload file

Structure factor file (CIF format) (371.1 kbytes)
[ doi:10.1107/S0108270113006185/qs3023IIIsup4.hkl ]
Contains datablock III


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