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Crystal structure of metronidazolium tetrachloridoaurate(III)
Metronidazole (MET) [systematic names: 1-(2-hydroxyethyl)-2-methyl-5-nitro-1H-imidazole and 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol] is a medication that is used to treat infections from a variety of anaerobic organisms. As with other imidazole derivatives, metronidazole is also susceptible...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2015
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4518979/ https://www.ncbi.nlm.nih.gov/pubmed/26279873 http://dx.doi.org/10.1107/S2056989015010798 |
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author | Quinlivan, Patrick J. Wu, Ja-Shin Upmacis, Rita K. |
author_facet | Quinlivan, Patrick J. Wu, Ja-Shin Upmacis, Rita K. |
author_sort | Quinlivan, Patrick J. |
collection | PubMed |
description | Metronidazole (MET) [systematic names: 1-(2-hydroxyethyl)-2-methyl-5-nitro-1H-imidazole and 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol] is a medication that is used to treat infections from a variety of anaerobic organisms. As with other imidazole derivatives, metronidazole is also susceptible to protonation. However, there are few reports of the structures of metronidazolium derivatives. In the title compound, (C(6)H(10)N(3)O(3))[AuCl(4)] [systematic name: 1-(2-hydroxyethyl)-2-methyl-5-nitro-1H-imidazol-3-ium tetrachloridoaurate(III)], the asymmetric unit consists of a metronidazolium cation, [H(MET)](+), and a tetrachloridoaurate(III) anion, [AuCl(4)](−), in which the Au(III) ion is in a slightly distorted square-planar coordination environment. In the cation, the nitro group is essentially coplanar with the imidazole ring, as indicated by an O N—C=C torsion angle of −0.2 (4)°, while the hydroxyethyl group is in a coiled conformation, with an O(H)—C—C—N torsion angle of 62.3 (3)°. In the crystal, the anion and cation are linked by an intermolecular O—H⋯Cl hydrogen bond. In addition, the N—H group of the metronidazolium ion serves as a hydrogen-bond donor to the O atom of the hydroxyethyl group of a symmetry-related molecule, leading to the formation of chains along [010]. |
format | Online Article Text |
id | pubmed-4518979 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-45189792015-08-14 Crystal structure of metronidazolium tetrachloridoaurate(III) Quinlivan, Patrick J. Wu, Ja-Shin Upmacis, Rita K. Acta Crystallogr E Crystallogr Commun Research Communications Metronidazole (MET) [systematic names: 1-(2-hydroxyethyl)-2-methyl-5-nitro-1H-imidazole and 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol] is a medication that is used to treat infections from a variety of anaerobic organisms. As with other imidazole derivatives, metronidazole is also susceptible to protonation. However, there are few reports of the structures of metronidazolium derivatives. In the title compound, (C(6)H(10)N(3)O(3))[AuCl(4)] [systematic name: 1-(2-hydroxyethyl)-2-methyl-5-nitro-1H-imidazol-3-ium tetrachloridoaurate(III)], the asymmetric unit consists of a metronidazolium cation, [H(MET)](+), and a tetrachloridoaurate(III) anion, [AuCl(4)](−), in which the Au(III) ion is in a slightly distorted square-planar coordination environment. In the cation, the nitro group is essentially coplanar with the imidazole ring, as indicated by an O N—C=C torsion angle of −0.2 (4)°, while the hydroxyethyl group is in a coiled conformation, with an O(H)—C—C—N torsion angle of 62.3 (3)°. In the crystal, the anion and cation are linked by an intermolecular O—H⋯Cl hydrogen bond. In addition, the N—H group of the metronidazolium ion serves as a hydrogen-bond donor to the O atom of the hydroxyethyl group of a symmetry-related molecule, leading to the formation of chains along [010]. International Union of Crystallography 2015-06-17 /pmc/articles/PMC4518979/ /pubmed/26279873 http://dx.doi.org/10.1107/S2056989015010798 Text en © Quinlivan 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 Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Research Communications Quinlivan, Patrick J. Wu, Ja-Shin Upmacis, Rita K. Crystal structure of metronidazolium tetrachloridoaurate(III) |
title | Crystal structure of metronidazolium tetrachloridoaurate(III) |
title_full | Crystal structure of metronidazolium tetrachloridoaurate(III) |
title_fullStr | Crystal structure of metronidazolium tetrachloridoaurate(III) |
title_full_unstemmed | Crystal structure of metronidazolium tetrachloridoaurate(III) |
title_short | Crystal structure of metronidazolium tetrachloridoaurate(III) |
title_sort | crystal structure of metronidazolium tetrachloridoaurate(iii) |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4518979/ https://www.ncbi.nlm.nih.gov/pubmed/26279873 http://dx.doi.org/10.1107/S2056989015010798 |
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