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2-{[2,8-Bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium trichloroacetate: Crystal structure and Hirshfeld surface analysis

The asymmetric unit of the centrosymmetric title salt, C17H17F6N2O+C2Cl3O2 , comprises a single ion-pair. The hydroxy-O and ammonium-N atoms lie to the same side of the cation, a disposition maintained by a charge-assisted ammonium-N—HO(hydroxy) hydrogen bond [the Oh—Cm—Cm–Na (h = hydroxy, m = meth...

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Main Authors: Wardell, James L., Jotani, Mukesh M., Tiekink, Edward R. T. *
Format: Article
Language:English
Published: 2018
Subjects:
QD Chemistry
Online Access:http://eprints.sunway.edu.my/943/1/Tiekink%202-%20%7B%5B2%2C8-%29%20Acta%20Cryst%20%282018%29%20E74%201851.pdf
http://eprints.sunway.edu.my/943/
http://doi.org/10.1107/S2056989018016389
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spelling my.sunway.eprints.9432020-10-07T08:58:48Z http://eprints.sunway.edu.my/943/ 2-{[2,8-Bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium trichloroacetate: Crystal structure and Hirshfeld surface analysis Wardell, James L. Jotani, Mukesh M. Tiekink, Edward R. T. * QD Chemistry The asymmetric unit of the centrosymmetric title salt, C17H17F6N2O+C2Cl3O2 , comprises a single ion-pair. The hydroxy-O and ammonium-N atoms lie to the same side of the cation, a disposition maintained by a charge-assisted ammonium-N—HO(hydroxy) hydrogen bond [the Oh—Cm—Cm–Na (h = hydroxy, m = methine, a = ammonium) torsion angle is 58.90 (19)⁰]. The piperidin-1-ium group is approximately perpendicular to the quinolinyl residue [Cq—Cm—Cm–Na (q = quinolinyl) is 178.90 (15)⁰] so that the cation, to a first approximation, has the shape of the letter L. The most prominent feature of the supramolecular association in the crystal is the formation of chains along the a-axis direction, being stabilized by charge-assisted hydrogen-bonds. Thus, ammonium-N+ —HO(carboxylate) hydrogen bonds are formed whereby two ammonium cations bridge a pair of carboxylate-O atoms, leading to eightmembered {OHNH}2 synthons. The resulting four-ion aggregates are linked into the supramolecular chain via charge-assisted hydroxyl-O—HO(carboxylate) hydrogen bonds. The connections between the chains, leading to a three-dimensional architecture, are of the type C—X, for X = Cl and F. The analysis of the calculated Hirshfeld surface points to the importance of XH contacts to the surface (X = F, 25.4% and X = Cl, 19.7%) along with a significant contribution from OH hydrogen-bonds (10.2%). Conversely, HH contacts, at 12.4%, make a relatively small contribution to the surface. 2018-11 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/943/1/Tiekink%202-%20%7B%5B2%2C8-%29%20Acta%20Cryst%20%282018%29%20E74%201851.pdf Wardell, James L. and Jotani, Mukesh M. and Tiekink, Edward R. T. * (2018) 2-{[2,8-Bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium trichloroacetate: Crystal structure and Hirshfeld surface analysis. Acta Crystallographica Section E Crystallographic Communications, 74 (12). pp. 1851-1856. ISSN 2056-9890 http://doi.org/10.1107/S2056989018016389 doi:10.1107/S2056989018016389
institution Sunway University
building Sunway Campus Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Sunway University
content_source Sunway Institutional Repository
url_provider http://eprints.sunway.edu.my/
language English
topic QD Chemistry
spellingShingle QD Chemistry
Wardell, James L.
Jotani, Mukesh M.
Tiekink, Edward R. T. *
2-{[2,8-Bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium trichloroacetate: Crystal structure and Hirshfeld surface analysis
description The asymmetric unit of the centrosymmetric title salt, C17H17F6N2O+C2Cl3O2 , comprises a single ion-pair. The hydroxy-O and ammonium-N atoms lie to the same side of the cation, a disposition maintained by a charge-assisted ammonium-N—HO(hydroxy) hydrogen bond [the Oh—Cm—Cm–Na (h = hydroxy, m = methine, a = ammonium) torsion angle is 58.90 (19)⁰]. The piperidin-1-ium group is approximately perpendicular to the quinolinyl residue [Cq—Cm—Cm–Na (q = quinolinyl) is 178.90 (15)⁰] so that the cation, to a first approximation, has the shape of the letter L. The most prominent feature of the supramolecular association in the crystal is the formation of chains along the a-axis direction, being stabilized by charge-assisted hydrogen-bonds. Thus, ammonium-N+ —HO(carboxylate) hydrogen bonds are formed whereby two ammonium cations bridge a pair of carboxylate-O atoms, leading to eightmembered {OHNH}2 synthons. The resulting four-ion aggregates are linked into the supramolecular chain via charge-assisted hydroxyl-O—HO(carboxylate) hydrogen bonds. The connections between the chains, leading to a three-dimensional architecture, are of the type C—X, for X = Cl and F. The analysis of the calculated Hirshfeld surface points to the importance of XH contacts to the surface (X = F, 25.4% and X = Cl, 19.7%) along with a significant contribution from OH hydrogen-bonds (10.2%). Conversely, HH contacts, at 12.4%, make a relatively small contribution to the surface.
format Article
author Wardell, James L.
Jotani, Mukesh M.
Tiekink, Edward R. T. *
author_facet Wardell, James L.
Jotani, Mukesh M.
Tiekink, Edward R. T. *
author_sort Wardell, James L.
title 2-{[2,8-Bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium trichloroacetate: Crystal structure and Hirshfeld surface analysis
title_short 2-{[2,8-Bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium trichloroacetate: Crystal structure and Hirshfeld surface analysis
title_full 2-{[2,8-Bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium trichloroacetate: Crystal structure and Hirshfeld surface analysis
title_fullStr 2-{[2,8-Bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium trichloroacetate: Crystal structure and Hirshfeld surface analysis
title_full_unstemmed 2-{[2,8-Bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium trichloroacetate: Crystal structure and Hirshfeld surface analysis
title_sort 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium trichloroacetate: crystal structure and hirshfeld surface analysis
publishDate 2018
url http://eprints.sunway.edu.my/943/1/Tiekink%202-%20%7B%5B2%2C8-%29%20Acta%20Cryst%20%282018%29%20E74%201851.pdf
http://eprints.sunway.edu.my/943/
http://doi.org/10.1107/S2056989018016389
_version_ 1680323401589194752
score 13.211869

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