Cargando…
Racemic mefloquinium chlorodifluoroacetate: crystal structure and Hirshfeld surface analysis
In the racemic title molecular salt, C(17)H(17)F(6)N(2)O(+)·C(2)ClF(2)O(3) (−) (systematic name: 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium chlorodifluoroacetate), the cation, which is protonated at the piperidine N atom, has the shape of the letter, L, with t...
Autores principales: | , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2018
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6038619/ https://www.ncbi.nlm.nih.gov/pubmed/30002881 http://dx.doi.org/10.1107/S2056989018007703 |
_version_ | 1783338532562010112 |
---|---|
author | Wardell, James L. Wardell, Solange M. S. V. Jotani, Mukesh M. Tiekink, Edward R. T. |
author_facet | Wardell, James L. Wardell, Solange M. S. V. Jotani, Mukesh M. Tiekink, Edward R. T. |
author_sort | Wardell, James L. |
collection | PubMed |
description | In the racemic title molecular salt, C(17)H(17)F(6)N(2)O(+)·C(2)ClF(2)O(3) (−) (systematic name: 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium chlorodifluoroacetate), the cation, which is protonated at the piperidine N atom, has the shape of the letter, L, with the piperidin-1-ium group being approximately orthogonal to the quinolinyl residue [the C(q)—C(m)—C(m)–N(a) (q = quinolinyl; m = methine; a = ammonium) torsion angle is 177.79 (18)°]. An intramolecular, charge-assisted ammonium-N—H⋯O(hydroxyl) hydrogen bond ensures the hydroxy-O and ammonium-N atoms lie to the same side of the molecule [O(h)—C(m)—C(m)—N(a) (h = hydroxyl) = −59.7 (2)°]. In the crystal, charge-assisted hydroxyl-O—H⋯O(−)(carboxylate) and ammonium-N(+)—H⋯O(−)(carboxylate) hydrogen bonds generate a supramolecular chain along [010]; the chain is consolidated by C—H⋯O interactions. Links between chains to form supramolecular layers are of the type C—Cl⋯π(quinolinyl-C(6)) and the layers thus formed stack along the a-axis direction without directional interactions between them. The analysis of the calculated Hirshfeld surface points to the dominance of F⋯H contacts to the surface (40.8%) with significant contributions from F⋯F (10.5%) and C⋯F (7.0%) contacts. |
format | Online Article Text |
id | pubmed-6038619 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-60386192018-07-12 Racemic mefloquinium chlorodifluoroacetate: crystal structure and Hirshfeld surface analysis Wardell, James L. Wardell, Solange M. S. V. Jotani, Mukesh M. Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications In the racemic title molecular salt, C(17)H(17)F(6)N(2)O(+)·C(2)ClF(2)O(3) (−) (systematic name: 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium chlorodifluoroacetate), the cation, which is protonated at the piperidine N atom, has the shape of the letter, L, with the piperidin-1-ium group being approximately orthogonal to the quinolinyl residue [the C(q)—C(m)—C(m)–N(a) (q = quinolinyl; m = methine; a = ammonium) torsion angle is 177.79 (18)°]. An intramolecular, charge-assisted ammonium-N—H⋯O(hydroxyl) hydrogen bond ensures the hydroxy-O and ammonium-N atoms lie to the same side of the molecule [O(h)—C(m)—C(m)—N(a) (h = hydroxyl) = −59.7 (2)°]. In the crystal, charge-assisted hydroxyl-O—H⋯O(−)(carboxylate) and ammonium-N(+)—H⋯O(−)(carboxylate) hydrogen bonds generate a supramolecular chain along [010]; the chain is consolidated by C—H⋯O interactions. Links between chains to form supramolecular layers are of the type C—Cl⋯π(quinolinyl-C(6)) and the layers thus formed stack along the a-axis direction without directional interactions between them. The analysis of the calculated Hirshfeld surface points to the dominance of F⋯H contacts to the surface (40.8%) with significant contributions from F⋯F (10.5%) and C⋯F (7.0%) contacts. International Union of Crystallography 2018-06-05 /pmc/articles/PMC6038619/ /pubmed/30002881 http://dx.doi.org/10.1107/S2056989018007703 Text en © Wardell et al. 2018 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 Wardell, James L. Wardell, Solange M. S. V. Jotani, Mukesh M. Tiekink, Edward R. T. Racemic mefloquinium chlorodifluoroacetate: crystal structure and Hirshfeld surface analysis |
title | Racemic mefloquinium chlorodifluoroacetate: crystal structure and Hirshfeld surface analysis |
title_full | Racemic mefloquinium chlorodifluoroacetate: crystal structure and Hirshfeld surface analysis |
title_fullStr | Racemic mefloquinium chlorodifluoroacetate: crystal structure and Hirshfeld surface analysis |
title_full_unstemmed | Racemic mefloquinium chlorodifluoroacetate: crystal structure and Hirshfeld surface analysis |
title_short | Racemic mefloquinium chlorodifluoroacetate: crystal structure and Hirshfeld surface analysis |
title_sort | racemic mefloquinium chlorodifluoroacetate: crystal structure and hirshfeld surface analysis |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6038619/ https://www.ncbi.nlm.nih.gov/pubmed/30002881 http://dx.doi.org/10.1107/S2056989018007703 |
work_keys_str_mv | AT wardelljamesl racemicmefloquiniumchlorodifluoroacetatecrystalstructureandhirshfeldsurfaceanalysis AT wardellsolangemsv racemicmefloquiniumchlorodifluoroacetatecrystalstructureandhirshfeldsurfaceanalysis AT jotanimukeshm racemicmefloquiniumchlorodifluoroacetatecrystalstructureandhirshfeldsurfaceanalysis AT tiekinkedwardrt racemicmefloquiniumchlorodifluoroacetatecrystalstructureandhirshfeldsurfaceanalysis |