title: Synthesis and structural characterization of 1-[2-(5-nitro-1H-indol-2-yl)phenyl]methylpyridinium chloride.
abstract: 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) 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)°].
authors: School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia. john_bremner@uow.edu.au
authors: John B
authors: JB
authors: Bremner
authors: Siritron
authors: S
authors: Samosorn
authors: Brian W
authors: BW
authors: Skelton
authors: Allan H
authors: AH
authors: White
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001426:Bacterial Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism; D018360:Crystallography, X-Ray; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D027425:ATP-Binding Cassette, Sub-Family C Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism; D011726:Pyridinium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013211:Staphylococcus aureus / Q000187:drug effects / Q000378:metabolism
chemical_list: D000900:Anti-Bacterial Agents; D001426:Bacterial Proteins; D007211:Indoles; D027425:ATP-Binding Cassette, Sub-Family C Proteins; D011726:Pyridinium Compounds; C568720:1-(2-(5-nitro-1H-indol-2-yl)phenyl)methylpyridinium chloride; C075040:NorA protein, Staphylococcus