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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| Format: | Article |
| Language: | English |
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2018
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| Online Access: | http://eprints.sunway.edu.my/943/ http://eprints.sunway.edu.my/943/1/Tiekink%202-%20%7B%5B2%2C8-%29%20Acta%20Cryst%20%282018%29%20E74%201851.pdf |
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| 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. |
| building | SU Institutional Repository |
| collection | Online Access |
| 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. |
| first_indexed | 2025-11-14T21:15:20Z |
| format | Article |
| id | sunway-943 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:15:20Z |
| publishDate | 2018 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-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 |
| 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 |
| title | 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_short | 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 |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/943/ http://eprints.sunway.edu.my/943/ http://eprints.sunway.edu.my/943/ http://eprints.sunway.edu.my/943/1/Tiekink%202-%20%7B%5B2%2C8-%29%20Acta%20Cryst%20%282018%29%20E74%201851.pdf |