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Crystal structures of two chiral piperidine derivatives: 1-[(1R)-2-hy­droxy-1-phenyl­eth­yl]piperidin-4-one and 8-[(1S)-1-phenyl­eth­yl]-1,4-dioxa-8-aza­spiro­[4.5]decane-7-thione

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-hy­droxy-1-phenyl­eth­yl]piperidin-4-one, C(13)H(17)NO(2), (I), has a chair conformation, while the piperidine substituted in posit...

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Autores principales: Romero, Nancy, Bernès, Sylvain, Roa, Luis F., Terán, Joel L., Gnecco, Dino
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4647425/
https://www.ncbi.nlm.nih.gov/pubmed/26594408
http://dx.doi.org/10.1107/S2056989015017119
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author Romero, Nancy
Bernès, Sylvain
Roa, Luis F.
Terán, Joel L.
Gnecco, Dino
author_facet Romero, Nancy
Bernès, Sylvain
Roa, Luis F.
Terán, Joel L.
Gnecco, Dino
author_sort Romero, Nancy
collection PubMed
description 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-hy­droxy-1-phenyl­eth­yl]piperidin-4-one, C(13)H(17)NO(2), (I), has a chair conformation, while the piperidine substituted in position 2 with a thio­carbonyl group, 8-[(1S)-1-phenyl­eth­yl]-1,4-dioxa-8-aza­spiro­[4.5]decane-7-thione, C(15)H(19)NO(2)S, (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 mol­ecules into supra­molecular chains propagating along the b-axis direction. In the crystal of (II), the mol­ecules are linked by weak C—H⋯S contacts into supra­molecular chains propagating along the b-axis direction.
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spelling pubmed-46474252015-11-20 Crystal structures of two chiral piperidine derivatives: 1-[(1R)-2-hy­droxy-1-phenyl­eth­yl]piperidin-4-one and 8-[(1S)-1-phenyl­eth­yl]-1,4-dioxa-8-aza­spiro­[4.5]decane-7-thione Romero, Nancy Bernès, Sylvain Roa, Luis F. Terán, Joel L. Gnecco, Dino Acta Crystallogr E Crystallogr Commun Research Communications 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-hy­droxy-1-phenyl­eth­yl]piperidin-4-one, C(13)H(17)NO(2), (I), has a chair conformation, while the piperidine substituted in position 2 with a thio­carbonyl group, 8-[(1S)-1-phenyl­eth­yl]-1,4-dioxa-8-aza­spiro­[4.5]decane-7-thione, C(15)H(19)NO(2)S, (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 mol­ecules into supra­molecular chains propagating along the b-axis direction. In the crystal of (II), the mol­ecules are linked by weak C—H⋯S contacts into supra­molecular chains propagating along the b-axis direction. International Union of Crystallography 2015-09-26 /pmc/articles/PMC4647425/ /pubmed/26594408 http://dx.doi.org/10.1107/S2056989015017119 Text en © Romero et al. 2015 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/
spellingShingle Research Communications
Romero, Nancy
Bernès, Sylvain
Roa, Luis F.
Terán, Joel L.
Gnecco, Dino
Crystal structures of two chiral piperidine derivatives: 1-[(1R)-2-hy­droxy-1-phenyl­eth­yl]piperidin-4-one and 8-[(1S)-1-phenyl­eth­yl]-1,4-dioxa-8-aza­spiro­[4.5]decane-7-thione
title Crystal structures of two chiral piperidine derivatives: 1-[(1R)-2-hy­droxy-1-phenyl­eth­yl]piperidin-4-one and 8-[(1S)-1-phenyl­eth­yl]-1,4-dioxa-8-aza­spiro­[4.5]decane-7-thione
title_full Crystal structures of two chiral piperidine derivatives: 1-[(1R)-2-hy­droxy-1-phenyl­eth­yl]piperidin-4-one and 8-[(1S)-1-phenyl­eth­yl]-1,4-dioxa-8-aza­spiro­[4.5]decane-7-thione
title_fullStr Crystal structures of two chiral piperidine derivatives: 1-[(1R)-2-hy­droxy-1-phenyl­eth­yl]piperidin-4-one and 8-[(1S)-1-phenyl­eth­yl]-1,4-dioxa-8-aza­spiro­[4.5]decane-7-thione
title_full_unstemmed Crystal structures of two chiral piperidine derivatives: 1-[(1R)-2-hy­droxy-1-phenyl­eth­yl]piperidin-4-one and 8-[(1S)-1-phenyl­eth­yl]-1,4-dioxa-8-aza­spiro­[4.5]decane-7-thione
title_short Crystal structures of two chiral piperidine derivatives: 1-[(1R)-2-hy­droxy-1-phenyl­eth­yl]piperidin-4-one and 8-[(1S)-1-phenyl­eth­yl]-1,4-dioxa-8-aza­spiro­[4.5]decane-7-thione
title_sort crystal structures of two chiral piperidine derivatives: 1-[(1r)-2-hy­droxy-1-phenyl­eth­yl]piperidin-4-one and 8-[(1s)-1-phenyl­eth­yl]-1,4-dioxa-8-aza­spiro­[4.5]decane-7-thione
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4647425/
https://www.ncbi.nlm.nih.gov/pubmed/26594408
http://dx.doi.org/10.1107/S2056989015017119
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