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...

Descripción completa

Detalles Bibliográficos
Autores principales: Wardell, James L., Wardell, Solange M. S. V., Jotani, Mukesh M., Tiekink, Edward R. T.
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