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Synthesis and Structural Characterization of 1-[2-(5-Nitro-1H-indol-2-yl)phenyl]methylpyridinium Chloride

1
School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia
2
Department of Chemistry, Srinakharinwirot University, Bangkok 10110, Thailand
3
School of Biomedical, Biomolecular and Chemical Sciences, Chemistry M313, The University of Western Australia, Crawley, W.A. 6009, Australia
*
Author to whom correspondence should be addressed.
Molecules 2011, 16(9), 7627-7633; https://doi.org/10.3390/molecules16097627
Received: 29 July 2011 / Revised: 22 August 2011 / Accepted: 25 August 2011 / Published: 6 September 2011
In the course of studies on hybrid antibacterials incorporating 2-aryl-5-nitro-1H-indole moieties as potential bacterial NorA efflux pump inhibitors, the compound 1-[2-(5-nitro-1H-indol-2-yl)phenyl]methylpyridinium chloride (2) was synthesized and structurally characterized. This pyridinium chloride salt crystallized in the monoclinic space group P21/c with the following unit cell dimensions: a 10.274(3) Å, b 13.101(4) Å, c 13.439(4) Å, b 107.702(7)°, V 1723.2(9) Å3, Z (f.u.) = 4; R1 = 0.048, and wR2 = 0.13. Of interest in the single crystal X-ray structure is the (intramolecular) disposition of the pyridinium plane over the indole heterocyclic residue [interplanar dihedral angle 17.91(4)°]. View Full-Text
Keywords: indole; pyridinium salt; X-ray crystal structure indole; pyridinium salt; X-ray crystal structure
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Bremner, J.B.; Samosorn, S.; Skelton, B.W.; White, A.H. Synthesis and Structural Characterization of 1-[2-(5-Nitro-1H-indol-2-yl)phenyl]methylpyridinium Chloride. Molecules 2011, 16, 7627-7633.

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