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Crystal structures of bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate and tetrachloridocuprate
(9S,13S,14S)-3-Methoxy-17-methylmorphinan (dextromethorphan) forms two isostructural salts with (a) tetrachloridocobaltate, namely bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate, (C(18)H(26)NO)(2)[CoCl(4)], and (b) tetrachloridocuprate, namely bis[(9S,13S,14S)-3...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2017
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5209774/ https://www.ncbi.nlm.nih.gov/pubmed/28083138 http://dx.doi.org/10.1107/S2056989016019939 |
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author | Gauchat, Eric Nazarenko, Alexander Y. |
author_facet | Gauchat, Eric Nazarenko, Alexander Y. |
author_sort | Gauchat, Eric |
collection | PubMed |
description | (9S,13S,14S)-3-Methoxy-17-methylmorphinan (dextromethorphan) forms two isostructural salts with (a) tetrachloridocobaltate, namely bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate, (C(18)H(26)NO)(2)[CoCl(4)], and (b) tetrachloridocuprate, namely bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocuprate, (C(18)H(26)NO)(2)[CuCl(4)]. The distorted tetrahedral anions are located on twofold rotational axes. The dextromethorphan cation can be described as being composed of two ring systems, a tetrahydronaphthalene system A+B and a decahydroisoquinolinium subunit C+D, that are nearly perpendicular to one another: the angle between mean planes of the A+B and C+D moieties is 78.8 (1)° for (a) and 79.0 (1)° for (b). Two symmetry-related cations of protonated dextromethorphan are connected to the tetrachloridocobaltate (or tetrachloridocuprate) anions via strong N—H⋯Cl hydrogen bonds, forming neutral ion associates. These associates are packed in the (001) plane with no strong attractive bonding between them. Both compounds are attractive crystalline forms for unambiguous identification of the dextromethorphan and, presumably, of its optical isomer, levomethorphan. |
format | Online Article Text |
id | pubmed-5209774 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-52097742017-01-12 Crystal structures of bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate and tetrachloridocuprate Gauchat, Eric Nazarenko, Alexander Y. Acta Crystallogr E Crystallogr Commun Research Communications (9S,13S,14S)-3-Methoxy-17-methylmorphinan (dextromethorphan) forms two isostructural salts with (a) tetrachloridocobaltate, namely bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate, (C(18)H(26)NO)(2)[CoCl(4)], and (b) tetrachloridocuprate, namely bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocuprate, (C(18)H(26)NO)(2)[CuCl(4)]. The distorted tetrahedral anions are located on twofold rotational axes. The dextromethorphan cation can be described as being composed of two ring systems, a tetrahydronaphthalene system A+B and a decahydroisoquinolinium subunit C+D, that are nearly perpendicular to one another: the angle between mean planes of the A+B and C+D moieties is 78.8 (1)° for (a) and 79.0 (1)° for (b). Two symmetry-related cations of protonated dextromethorphan are connected to the tetrachloridocobaltate (or tetrachloridocuprate) anions via strong N—H⋯Cl hydrogen bonds, forming neutral ion associates. These associates are packed in the (001) plane with no strong attractive bonding between them. Both compounds are attractive crystalline forms for unambiguous identification of the dextromethorphan and, presumably, of its optical isomer, levomethorphan. International Union of Crystallography 2017-01-01 /pmc/articles/PMC5209774/ /pubmed/28083138 http://dx.doi.org/10.1107/S2056989016019939 Text en © Gauchat and Nazarenko 2017 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 Gauchat, Eric Nazarenko, Alexander Y. Crystal structures of bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate and tetrachloridocuprate |
title | Crystal structures of bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate and tetrachloridocuprate |
title_full | Crystal structures of bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate and tetrachloridocuprate |
title_fullStr | Crystal structures of bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate and tetrachloridocuprate |
title_full_unstemmed | Crystal structures of bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate and tetrachloridocuprate |
title_short | Crystal structures of bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate and tetrachloridocuprate |
title_sort | crystal structures of bis[(9s,13s,14s)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate and tetrachloridocuprate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5209774/ https://www.ncbi.nlm.nih.gov/pubmed/28083138 http://dx.doi.org/10.1107/S2056989016019939 |
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