ArticleActa crystallographica. Section E, Crystallographic communications2015
Crystal structures of two chiral piperidine derivatives: 1-[(1R)-2-hy-droxy-1-phenyl-eth-yl]piperidin-4-one and 8-[(1S)-1-phenyl-eth-yl]-1,4-dioxa-8-aza-spiro-[4.5]decane-7-thione.
Article in Acta crystallographica. Section E, Crystallographic communications, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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1 citing paper in PubMed.
- Recent advances in piperidones as privileged scaffolds for drug discovery and development.Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents · 2026Review
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5 authors.
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Abstract
The crystal structures of the two title piperidine derivatives show different conformations for the six-membered heterocycle. The N-substituted 4-piperidinone 1-[(1R)-2-hy-droxy-1-phenyl-eth-yl]piperidin-4-one, C13H17NO2, (I), has a chair conformation, while the piperidine substituted in position 2 with a thio-carbonyl group, 8-[(1S)-1-phenyl-eth-yl]-1,4-dioxa-8-aza-spiro-[4.5]decane-7-thione, C15H19NO2S, (II), features a half-chair conformation. Comparison of the two structures, and data retrieved from the literature, suggests that the conformational flexibility is mainly related to the hybridization state of the C atom α to the piperidinic N atom: a Csp (3) atom favours the chair conformer, while a Csp (2) atom distorts the ring towards a half-chair conformer. In the crystal structure of (I), weak C-H⋯O hydrogen bonds link the mol-ecules into supra-molecular chains propagating along the b-axis direction. In the crystal of (II), the mol-ecules are linked by weak C-H⋯S contacts into supra-molecular chains propagating along the b-axis direction.
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