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Crystal structure of (RS)-4-(3-carboxy-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 3-carboxy-5-fluorobenzoate
In the title organic salt, C(17)H(20)F(2)N(3)O(3) (+)·C(8)H(4)FO(4) (−), proton transfer leads to one protonated lomefloxacin molecule (HLf(+)) and one 3-carboxy-5-fluorobenzoate (5-F-Hip(−)) anion in the asymmetric unit. The HLf(+) cation is bent, with a dihedral angle of 38.3 (1)° between the q...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6323884/ https://www.ncbi.nlm.nih.gov/pubmed/30713736 http://dx.doi.org/10.1107/S2056989018016961 |
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author | Feng, Sheng Zhu, Gui-Liang Sun, Jia-Jia Chen, Chen Zhang, Zhi-Hui |
author_facet | Feng, Sheng Zhu, Gui-Liang Sun, Jia-Jia Chen, Chen Zhang, Zhi-Hui |
author_sort | Feng, Sheng |
collection | PubMed |
description | In the title organic salt, C(17)H(20)F(2)N(3)O(3) (+)·C(8)H(4)FO(4) (−), proton transfer leads to one protonated lomefloxacin molecule (HLf(+)) and one 3-carboxy-5-fluorobenzoate (5-F-Hip(−)) anion in the asymmetric unit. The HLf(+) cation is bent, with a dihedral angle of 38.3 (1)° between the quinoline ring and the piperazinium moiety. In the crystal, two kinds of N—H⋯O and O—H⋯O hydrogen-bonded chains cross-link each other to produce a three-dimensional network structure that is additionally stabilized by weak C—H⋯O and C—H⋯F hydrogen bonds, as well as π–π interactions. The methyl group attached to the piperazinium ring is disordered over two sets of sites [refined ratio: 0.645 (5):0.335 (5)], indicating the presence of both enantiomers of the cation in the structure. |
format | Online Article Text |
id | pubmed-6323884 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-63238842019-02-01 Crystal structure of (RS)-4-(3-carboxy-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 3-carboxy-5-fluorobenzoate Feng, Sheng Zhu, Gui-Liang Sun, Jia-Jia Chen, Chen Zhang, Zhi-Hui Acta Crystallogr E Crystallogr Commun Research Communications In the title organic salt, C(17)H(20)F(2)N(3)O(3) (+)·C(8)H(4)FO(4) (−), proton transfer leads to one protonated lomefloxacin molecule (HLf(+)) and one 3-carboxy-5-fluorobenzoate (5-F-Hip(−)) anion in the asymmetric unit. The HLf(+) cation is bent, with a dihedral angle of 38.3 (1)° between the quinoline ring and the piperazinium moiety. In the crystal, two kinds of N—H⋯O and O—H⋯O hydrogen-bonded chains cross-link each other to produce a three-dimensional network structure that is additionally stabilized by weak C—H⋯O and C—H⋯F hydrogen bonds, as well as π–π interactions. The methyl group attached to the piperazinium ring is disordered over two sets of sites [refined ratio: 0.645 (5):0.335 (5)], indicating the presence of both enantiomers of the cation in the structure. International Union of Crystallography 2019-01-01 /pmc/articles/PMC6323884/ /pubmed/30713736 http://dx.doi.org/10.1107/S2056989018016961 Text en © Feng et al. 2019 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 Feng, Sheng Zhu, Gui-Liang Sun, Jia-Jia Chen, Chen Zhang, Zhi-Hui Crystal structure of (RS)-4-(3-carboxy-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 3-carboxy-5-fluorobenzoate |
title | Crystal structure of (RS)-4-(3-carboxy-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 3-carboxy-5-fluorobenzoate |
title_full | Crystal structure of (RS)-4-(3-carboxy-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 3-carboxy-5-fluorobenzoate |
title_fullStr | Crystal structure of (RS)-4-(3-carboxy-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 3-carboxy-5-fluorobenzoate |
title_full_unstemmed | Crystal structure of (RS)-4-(3-carboxy-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 3-carboxy-5-fluorobenzoate |
title_short | Crystal structure of (RS)-4-(3-carboxy-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 3-carboxy-5-fluorobenzoate |
title_sort | crystal structure of (rs)-4-(3-carboxy-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 3-carboxy-5-fluorobenzoate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6323884/ https://www.ncbi.nlm.nih.gov/pubmed/30713736 http://dx.doi.org/10.1107/S2056989018016961 |
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