Hydrogen bonding in 2,6-bis(4-fluorophenyl)-3,5-dimethylpiperidin-4-one methanol solvate

Suresh, T. and Vijayakumar, V. and Kumar, L. Jyothish and Sarveswari, S. and Jotani, Mukesh M. and Otero-de-la-Roza, Alberto and Tan, Yee Seng * and Tiekink, Edward R. T. * (2016) Hydrogen bonding in 2,6-bis(4-fluorophenyl)-3,5-dimethylpiperidin-4-one methanol solvate. Zeitschrift für Kristallographie - Crystalline Materials, 231 (6). pp. 365-374. ISSN 2194-4946

Z. Kristallogr. 2016 231 365.pdf - Accepted Version

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Official URL: http://dx.doi.org/10.1515/zkri-2015-1915


The crystal structure analysis of a 2,6-diaryl 4-piperidone derivative, isolated as a mono-methanol solvate, reveals that both the piperidone and the methanol molecule lie on a crystallographic mirror plane. A chair conformation is found for the piperidone ring with the aryl and methyl groups in equatorial positions. The most prominent feature of the molecular packing is the formation of supramolecular zigzag chains mediated by amine-N–H···O(methanol) and hydroxyl-O–H···N(amine) hydrogen bonds, i.e. the methanol molecule serves as a bridge between piperidone molecules. The molecular structure is compared with that determined in an unsolvated form and the gas-phase equilibrium structure, obtained using density-functional theory (DFT); differences relate, in the main, to the relative dispositions of the aryl rings. An analysis of the Hirshfeld surfaces of the experimental structures indicates very similar relative contributions with the notable exception being the contribution by O···H/H···O which at 13.7% in the methanol solvate is >8.5% in the unsolvated form.

Item Type: Article
Additional Information: First author is with VIT University, Centre for Organic and Medicinal Chemistry, Vellore, Tamil Nadu & Orchid Chemicals & Pharmaceuticals Ltd, R&D Centre, Chennai; 2nd, 3rd and 4th authors are with VIT University, Centre for Organic and Medicinal Chemistry, Vellore, Tamil Nadu; 5th author is with Bhavan's Sheth R. A. College of Science, Department of Physics, Ahmedabad; 6th author is with National Institute of Nanotechnology, National Research Council of Canada; 7th and 8th authors are with Sunway University, Research Centre for Crystalline Materials, Faculty of Science and Technology
Uncontrolled Keywords: conformation; crystal structure analysis; DFT; piperidin-4-one; X-ray diffraction
Subjects: Q Science > QD Chemistry
Divisions: Others > Non Sunway Academics
Sunway University > School of Engineering and Technology [formerly School of Science and Technology until 2020] > Research Centre for Crystalline Materials moved to SMLS wef 2021
Depositing User: Ms. Molly Chuah
Related URLs:
Date Deposited: 02 Nov 2017 01:27
Last Modified: 07 Oct 2020 09:50
URI: http://eprints.sunway.edu.my/id/eprint/657

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