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A kryptoracemic salt: 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium (+)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
The asymmetric unit of the title salt, C(17)H(17)F(6)N(2)O(+)·C(10)H(8)F(3)O(3) (−), comprises two piperidin-1-ium cations and two carboxylate anions. The cations, each having an l-shaped conformation owing to the near orthogonal relationship between the quinolinyl and piperidin-1-ium residues, are...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4908568/ https://www.ncbi.nlm.nih.gov/pubmed/27308063 http://dx.doi.org/10.1107/S2056989016008495 |
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author | Wardell, James L. Wardell, Solange M. S. V. Tiekink, Edward R. T. |
author_facet | Wardell, James L. Wardell, Solange M. S. V. Tiekink, Edward R. T. |
author_sort | Wardell, James L. |
collection | PubMed |
description | The asymmetric unit of the title salt, C(17)H(17)F(6)N(2)O(+)·C(10)H(8)F(3)O(3) (−), comprises two piperidin-1-ium cations and two carboxylate anions. The cations, each having an l-shaped conformation owing to the near orthogonal relationship between the quinolinyl and piperidin-1-ium residues, are pseudo-enantiomeric. The anions have the same absolute configuration but differ in the relative orientations of the carboxylate, methoxy and benzene groups. Arguably, the most prominent difference between the anions occurs about the C(q)—O(m) bond as seen in the C(c)—C(q)—O(m)—C(m) torsion angles of −176.1 (3) and −67.1 (4)°, respectively (q = quaternary, m = methoxy and c = carboxylate). The presence of O(h)—H⋯O(c) and N(p)—H⋯O(c) hydrogen bonds leads to the formation of a supramolecular chain along the a axis (h = hydroxy and p = piperidin-1-ium); weak intramolecular N(p)—H⋯O(h) hydrogen bonds are also noted. Chains are connected into a three-dimensional architecture by C—H⋯F interactions. Based on a literature survey, related molecules/cations adopt a uniform conformation in the solid state based on the letter L. |
format | Online Article Text |
id | pubmed-4908568 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-49085682016-06-15 A kryptoracemic salt: 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium (+)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate Wardell, James L. Wardell, Solange M. S. V. Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications The asymmetric unit of the title salt, C(17)H(17)F(6)N(2)O(+)·C(10)H(8)F(3)O(3) (−), comprises two piperidin-1-ium cations and two carboxylate anions. The cations, each having an l-shaped conformation owing to the near orthogonal relationship between the quinolinyl and piperidin-1-ium residues, are pseudo-enantiomeric. The anions have the same absolute configuration but differ in the relative orientations of the carboxylate, methoxy and benzene groups. Arguably, the most prominent difference between the anions occurs about the C(q)—O(m) bond as seen in the C(c)—C(q)—O(m)—C(m) torsion angles of −176.1 (3) and −67.1 (4)°, respectively (q = quaternary, m = methoxy and c = carboxylate). The presence of O(h)—H⋯O(c) and N(p)—H⋯O(c) hydrogen bonds leads to the formation of a supramolecular chain along the a axis (h = hydroxy and p = piperidin-1-ium); weak intramolecular N(p)—H⋯O(h) hydrogen bonds are also noted. Chains are connected into a three-dimensional architecture by C—H⋯F interactions. Based on a literature survey, related molecules/cations adopt a uniform conformation in the solid state based on the letter L. International Union of Crystallography 2016-05-27 /pmc/articles/PMC4908568/ /pubmed/27308063 http://dx.doi.org/10.1107/S2056989016008495 Text en © Wardell et al. 2016 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Research Communications Wardell, James L. Wardell, Solange M. S. V. Tiekink, Edward R. T. A kryptoracemic salt: 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium (+)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate |
title | A kryptoracemic salt: 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium (+)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate |
title_full | A kryptoracemic salt: 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium (+)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate |
title_fullStr | A kryptoracemic salt: 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium (+)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate |
title_full_unstemmed | A kryptoracemic salt: 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium (+)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate |
title_short | A kryptoracemic salt: 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium (+)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate |
title_sort | kryptoracemic salt: 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium (+)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4908568/ https://www.ncbi.nlm.nih.gov/pubmed/27308063 http://dx.doi.org/10.1107/S2056989016008495 |
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