Staff View: Crystal structure and Hirshfeld surface analysis of 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium 2-hydroxy-2-phenylacetate hemihydrate

Crystal structure and Hirshfeld surface analysis of 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium 2-hydroxy-2-phenylacetate hemihydrate

The asymmetric unit of the title salt, C17H17F6N2O+·C8H7O3-·0.5H2O, comprises a pair of pseudo-enantiomeric (i.e. related by a non-crystallographic centre of symmetry) piperidin-1-ium cations, two carboxylate anions and a water molecule of crystallization. The cations have similar conformations a...

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Main Authors:	Wardell, James L., Jotani, Mukesh M., Tiekink, Edward R. T. *
Format:	Article
Language:	English
Published:	International Union of Crystallography 2016
Subjects:	QD Chemistry
Online Access:	http://eprints.sunway.edu.my/641/1/Acta%20Cryst.%20%282016%29.%20E72%2C%201618.pdf http://eprints.sunway.edu.my/641/ http://dx.doi.org/10.1107/S2056989016016492
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spelling	my.sunway.eprints.6412020-10-07T09:57:33Z http://eprints.sunway.edu.my/641/ Crystal structure and Hirshfeld surface analysis of 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium 2-hydroxy-2-phenylacetate hemihydrate Wardell, James L. Jotani, Mukesh M. Tiekink, Edward R. T. * QD Chemistry The asymmetric unit of the title salt, C17H17F6N2O+·C8H7O3-·0.5H2O, comprises a pair of pseudo-enantiomeric (i.e. related by a non-crystallographic centre of symmetry) piperidin-1-ium cations, two carboxylate anions and a water molecule of crystallization. The cations have similar conformations approximating to a letter, L: one of them shows disorder of its -CF3 group over two sets of sites in a 0.775 (3):0.225 (3) ratio. Distinctive conformations are found for the anions, one with the carboxylate group lying to one side of the plane through the phenyl ring and the other where the oxygen atoms lie to either side of the plane. In the latter, an intramolecular hydroxy-O-H...O(carboxylate) charge-assisted hydrogen bond is found. The packing features extensive O-H...O,N hydrogen bonding, often charge-assisted; C-H...[pi] interactions are also formed. The hydrogen bonding results in the formation of five distinctive supramolecular synthons and assembles molecules in the ac plane. The quinolinyl rings lie to either side of the layer and inter-digitate with layers on either side, are approximately parallel to the b axis and are connected by [pi]-[pi] [inter-centroid separation = 3.6904 (18) Å] as well as C-F...[pi](quinolinyl) interactions to consolidate the three-dimensional crystal. The dominance of the conventional hydrogen bonding in the molecular packing is confirmed by an analysis of the Hirshfeld surface. International Union of Crystallography 2016 Article PeerReviewed text en cc_by_nc_nd http://eprints.sunway.edu.my/641/1/Acta%20Cryst.%20%282016%29.%20E72%2C%201618.pdf Wardell, James L. and Jotani, Mukesh M. and Tiekink, Edward R. T. * (2016) Crystal structure and Hirshfeld surface analysis of 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium 2-hydroxy-2-phenylacetate hemihydrate. Acta Crystallographica Section E Crystallographic Communications, 72 (11). pp. 1618-1627. ISSN 2056-9890 http://dx.doi.org/10.1107/S2056989016016492 doi:10.1107/S2056989016016492
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. * Crystal structure and Hirshfeld surface analysis of 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium 2-hydroxy-2-phenylacetate hemihydrate
description	The asymmetric unit of the title salt, C17H17F6N2O+·C8H7O3-·0.5H2O, comprises a pair of pseudo-enantiomeric (i.e. related by a non-crystallographic centre of symmetry) piperidin-1-ium cations, two carboxylate anions and a water molecule of crystallization. The cations have similar conformations approximating to a letter, L: one of them shows disorder of its -CF3 group over two sets of sites in a 0.775 (3):0.225 (3) ratio. Distinctive conformations are found for the anions, one with the carboxylate group lying to one side of the plane through the phenyl ring and the other where the oxygen atoms lie to either side of the plane. In the latter, an intramolecular hydroxy-O-H...O(carboxylate) charge-assisted hydrogen bond is found. The packing features extensive O-H...O,N hydrogen bonding, often charge-assisted; C-H...[pi] interactions are also formed. The hydrogen bonding results in the formation of five distinctive supramolecular synthons and assembles molecules in the ac plane. The quinolinyl rings lie to either side of the layer and inter-digitate with layers on either side, are approximately parallel to the b axis and are connected by [pi]-[pi] [inter-centroid separation = 3.6904 (18) Å] as well as C-F...[pi](quinolinyl) interactions to consolidate the three-dimensional crystal. The dominance of the conventional hydrogen bonding in the molecular packing is confirmed by an analysis of the Hirshfeld 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	Crystal structure and Hirshfeld surface analysis of 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium 2-hydroxy-2-phenylacetate hemihydrate
title_short	Crystal structure and Hirshfeld surface analysis of 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium 2-hydroxy-2-phenylacetate hemihydrate
title_full	Crystal structure and Hirshfeld surface analysis of 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium 2-hydroxy-2-phenylacetate hemihydrate
title_fullStr	Crystal structure and Hirshfeld surface analysis of 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium 2-hydroxy-2-phenylacetate hemihydrate
title_full_unstemmed	Crystal structure and Hirshfeld surface analysis of 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium 2-hydroxy-2-phenylacetate hemihydrate
title_sort	crystal structure and hirshfeld surface analysis of 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium 2-hydroxy-2-phenylacetate hemihydrate
publisher	International Union of Crystallography
publishDate	2016
url	http://eprints.sunway.edu.my/641/1/Acta%20Cryst.%20%282016%29.%20E72%2C%201618.pdf http://eprints.sunway.edu.my/641/ http://dx.doi.org/10.1107/S2056989016016492
_version_	1680323389155180544
score	13.211869

Crystal structure and Hirshfeld surface analysis of 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium 2-hydroxy-2-phenylacetate hemihydrate

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