Synthesis and structural characterization of 1-[2-(5-Nitro-1H-indol-2-yl)phenyl]methylpyridinium chloride

Authors

John B. Bremner, University of WollongongFollow
Siritron Samosorn, Srinakharinwirot UniversityFollow
Brian W. Skelton, University of Western Australia
Allan White, University of Western Australia

RIS ID

53170

Publication Details

Bremner, J. B., Samosorn, S., Skelton, B. W. and White, A. H. (2011). Synthesis and structural characterization of 1-[2-(5-Nitro-1H-indol-2-yl)phenyl]methylpyridinium chloride. Molecules, 16 (9), 7627-7633.

Abstract

In the course of studies on hybrid antibacterials incorporating 2-aryl-5-nitro-1Hindolemoieties as potential bacterial NorA efflux pump inhibitors, the compound 1-[2-(5-nitro-1H-indol-2-yl)phenyl]methylpyridinium chloride (2) was synthesized and structurallycharacterized. This pyridinium chloride salt crystallized in the monoclinic space groupP21/c with the following unit cell dimensions: a 10.274(3) A, b 13.101(4) A, c 13.439(4)A, B 107.702(7)deg, V 1723.2(9) A3, Z (f.u.) = 4; R1 = 0.048, and wR2 = 0.13. Of interest inthe single crystal X-ray structure is the (intramolecular) disposition of the pyridinium planeover the indole heterocyclic residue [interplanar dihedral angle 17.91(4)deg].