Acta Crystallographica Section E

Structure Reports Online

Volume 69, Part 3 (March 2013)


organic compounds



nr2039 scheme

Acta Cryst. (2013). E69, o408-o409    [ doi:10.1107/S1600536813004017 ]

4-Hydroxy-1,1'-bis[(S)-1-phenylethyl]-5,5',6,6'-tetrahydro-3,4'-bipyridine-2,2'(1H,1'H)-dione

N. Romero, D. Gnecco, J. Terán and S. Bernès

Abstract: The title bis-piperidine, C26H28N2O3, was unexpectedly obtained via a dimerization mechanism promoted by acetic acid when performing the Dieckmann cyclization of a chiral amido ester. The S,S configuration was assigned by reference to the enantiomerically pure starting material. In the molecule, two core heterocycles are linked by a [sigma] bond. One ring includes a keto-enol group, while the other presents an enone functionality. Both rings present a conformation intermediate between envelope and screw-boat, and the dihedral angle between the mean planes passing through the rings [48.9 (1)°] is large enough to avoid hindrance between ring substituents. The enol tautomeric form in one ring favors the formation of strong intermolecular O-H...O=C hydrogen bonds. The resulting one-dimensional supramolecular structure features single-stranded helices running along the 21 screw axis parallel to [100].


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