Racemic mefloquinium chlorodifluoroacetate: Crystal structure and Hirshfeld surface analysis
In the racemic title molecular salt, C17H17F6N2O+.C2ClF2O3 -(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 be...
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International Union of Crystallography
2018
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my.sunway.eprints.8362020-10-07T09:06:08Z http://eprints.sunway.edu.my/836/ Racemic mefloquinium chlorodifluoroacetate: Crystal structure and Hirshfeld surface analysis Wardell, James L. Wardell, Solange M. S. V. Jotani, Mukesh M. Tiekink, Edward R. T. * QD Chemistry In the racemic title molecular salt, C17H17F6N2O+.C2ClF2O3 -(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 Cq—Cm—Cm–Na (q = quinolinyl; m = methine; a = ammonium) torsion angle is 177.79 (18)⁰]. 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 [Oh—Cm—Cm—Na (h = hydroxyl) = -59.7 (2)⁰]. 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-C6) 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 2018-05-23 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/836/1/Tiekink%20Racemic%20mefloquinium.pdf Wardell, James L. and Wardell, Solange M. S. V. and Jotani, Mukesh M. and Tiekink, Edward R. T. * (2018) Racemic mefloquinium chlorodifluoroacetate: Crystal structure and Hirshfeld surface analysis. Acta Crystallographica Section E Crystallographic Communications, 74 (7). pp. 895-900. ISSN 2056-9890 http://doi.org/10.1107/S2056989018007703 doi:10.1107/S2056989018007703 |
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QD Chemistry Wardell, James L. Wardell, Solange M. S. V. Jotani, Mukesh M. Tiekink, Edward R. T. * Racemic mefloquinium chlorodifluoroacetate: Crystal structure and Hirshfeld surface analysis |
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In the racemic title molecular salt, C17H17F6N2O+.C2ClF2O3
-(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 Cq—Cm—Cm–Na (q = quinolinyl; m = methine; a = ammonium) torsion angle is 177.79 (18)⁰]. 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 [Oh—Cm—Cm—Na (h = hydroxyl) = -59.7 (2)⁰]. 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-C6) 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. |
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Article |
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. |
title |
Racemic mefloquinium chlorodifluoroacetate: Crystal structure and Hirshfeld surface analysis |
title_short |
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_sort |
racemic mefloquinium chlorodifluoroacetate: crystal structure and hirshfeld surface analysis |
publisher |
International Union of Crystallography |
publishDate |
2018 |
url |
http://eprints.sunway.edu.my/836/1/Tiekink%20Racemic%20mefloquinium.pdf http://eprints.sunway.edu.my/836/ http://doi.org/10.1107/S2056989018007703 |
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1680323398317637632 |
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13.19449 |