Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Gauchat, Eric, Nazarenko, Alexander Y.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
Materias:
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
_version_ 1782490793016033280
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
work_keys_str_mv AT gauchateric crystalstructuresofbis9s13s14s3methoxy17methylmorphinaniumtetrachloridocobaltateandtetrachloridocuprate
AT nazarenkoalexandery crystalstructuresofbis9s13s14s3methoxy17methylmorphinaniumtetrachloridocobaltateandtetrachloridocuprate