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

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 P2(1)/c with the following unit cell dimensions: a 10.274(3) angstrom, b 13.101(4) angstrom, c 13.439(4) angstrom, beta 107.702(7)degrees, V 1723.2(9) angstrom(3), 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)degrees].