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

T. Suresh; V. Vijayakumar; L. Jyothish Kumar; S. Sarveswari; Mukesh M. Jotani; Alberto Otero-de-la-Roza; Yee Seng Tan; Edward R.T. Tiekink

doi:10.1515/zkri-2015-1915

Article

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

T. Suresh , V. Vijayakumar , L. Jyothish Kumar , S. Sarveswari , Mukesh M. Jotani , Alberto Otero-de-la-Roza , Yee Seng Tan and Edward R.T. Tiekink

Published/Copyright: May 12, 2016

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From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 231 Issue 6

Abstract

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.

Keywords: conformation; crystal structure analysis; DFT; piperidin-4-one; X-ray diffraction

Acknowledgments

The VIT University is thanked for providing facilities. The authors also grateful to SIF-Chemistry, VIT University, for providing the NMR and X-ray diffractometer (PXRD) facilities. AOR thanks the Spanish Malta/Consolider initiative (no. CSD2007-00045) and Alberta Innovates Technology Futures (AITF) for funding. The authors also express their gratitude to the anonymous reviewers, specifically for their suggestion to re-evaluate the literature structure.

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Supplemental Material:

The online version of this article (DOI: 10.1515/zkri-2015-1915) offers supplementary material, available to authorized users.

Received: 2015-10-1

Accepted: 2016-4-11

Published Online: 2016-5-12

Published in Print: 2016-6-1

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Keywords for this article

conformation; crystal structure analysis; DFT; piperidin-4-one; X-ray diffraction

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

Article

Abstract

Acknowledgments

References

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