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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2015
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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. |
format | Online Article Text |
id | pubmed-4647425 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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