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Abstract
The title compound, C28H32N2, (I), is one of a second generation of compounds designed and synthesized based on a very potent and selective α9α10 nicotinic acetylcholine receptor antagonist ZZ161C {1,1′-[[1,1′-biphenyl]-4,4′-diylbis(prop-2-yne-3,1-diyl)]bis(3,4-dimethylpyridin-1-ium) bromide}, which has shown analgesic effects in a chemotherapy-induced neuropathy animal model. Compound (I) was synthesized by the reaction of 4,4′-bis(3-bromoprop-1-yn-1-yl)-1,1′-biphenyl with piperidine at room temperature in acetonitrile. The single-crystal used for X-ray analysis was obtained by dissolving (I) in a mixture of dichloromethane and methanol, followed by slow evaporation of the solvent. In the crystal of (I), the biphenyl moiety has a twisted conformation, with a dihedral angle of 25.93 (4)° between the benzene rings. Both piperidine head groups in (I) are in the chair conformation and are oriented so that the N-atom lone pairs of each piperidine group point away from the central biphenyl moiety.
Document Type
Article
Publication Date
6-2017
Digital Object Identifier (DOI)
https://doi.org/10.1107/S2056989017007277
Funding Information
This investigation was supported by the Arkansas Research Alliance (ARA).
Related Content
Supporting information: this article has supporting information at journals.iucr.org/e.
CCDC reference: 1550512
Crystal structure: contains datablocks global, I. DOI: https://doi.org//10.1107/S2056989017007277/sj5530sup1.cif
Structure factors: contains datablock I. DOI: https://doi.org//10.1107/S2056989017007277/sj5530Isup2.hkl
Supporting information file. DOI: https://doi.org//10.1107/S2056989017007277/sj5530Isup3.cml
3D view of crystallographic information
Repository Citation
Walbaum, Anqi; Fifer, E. Kim; Parkin, Sean R.; and Crooks, Peter A., "Crystal Structure of 4,4′-bis[3-(piperidin-1-yl)prop-1-yn-1-yl]-1,1′-biphenyl" (2017). Chemistry Faculty Publications. 95.
https://uknowledge.uky.edu/chemistry_facpub/95
Powerpoint slides
sj5530sup1.cif (887 kB)
Crystal structure: contains datablocks global, I.
sj5530Isup2.hkl (326 kB)
Structure factors: contains datablock I.
sj5530Isup3.cml (8 kB)
Supporting information file.
Notes/Citation Information
Published in Acta Crystallographica Section E: Crystallographic Communications, v. 73, part 6, p. 864-866.
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.