Loader, J.R., Libri, S., Meijer, A.J.H.M. orcid.org/0000-0003-4803-3488 et al. (2 more authors) (2014) Highly fluorinated naphthalenes and bifurcated C–H⋯F–C hydrogen bonding. CrystEngComm, 16 (41). pp. 9711-9720.
Abstract
The synthesis and crystal structures of 1,2,4,5,6,8-hexafluoronaphthalene and 1,2,4,6,8-pentafluoronaphthalene are reported. Intermolecular interactions are dominated by offset stacking and by C–H⋯F–C hydrogen bonds. For hexafluoronaphthalene, molecules are linked in layers with (4,4) network topology via R12(6) C–H⋯(F–C)2 supramolecular synthons that are rationalised by consideration of the calculated electrostatic potential of the molecule. Such an arrangement is prevented by the additional hydrogen atom in pentafluoronaphthalene and molecules instead form tapes via an R12(8) (C–H⋯F)2 synthon. The geometric characteristics of C–H⋯(F–C)2 bifurcated hydrogen bonds have been analysed for crystal structures in the Cambridge Structural Database (6416 crystal structures; 9534 C–H⋯(F–C)2 bifurcated hydrogen bonds). A geometric analysis of these hydrogen bonds has enabled the extent of asymmetry of these hydrogen bonds to be assessed and indicates a preference for symmetrically bifurcated interactions.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2014 The Royal Society of Chemistry. This is an Open Access article distributed under the terms of the Creative Commons Attribution Licence (http://creativecommons.org/licenses/by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 27 Oct 2016 13:59 |
Last Modified: | 27 Oct 2016 13:59 |
Published Version: | https://dx.doi.org/10.1039/C4CE01322K |
Status: | Published |
Publisher: | Royal Society of Chemistry |
Refereed: | Yes |
Identification Number: | 10.1039/C4CE01322K |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:106349 |