Research Article: 2,4,6-Trinitro-N-[4-(phenyl­diazen­yl)phen­yl]aniline

Date Published: April 01, 2011

Publisher: International Union of Crystallography

Author(s): Graham Smith, Urs D. Wermuth.


The title compound, C18H12N6O6, was prepared from the reaction of 4-(phenyl­diazen­yl)aniline (aniline yellow) with picryl­sulfonic acid. The dihedral angle formed by the two benzene rings of the diphenyl­diazenyl ring system is 6.55 (13)° and that formed by the rings of the picrate–aniline ring system is 48.76 (12)°. The mol­ecule contains an intra­molecular aniline–nitro N—H⋯O hydrogen bond.

Partial Text

For the reaction of picryl chloride with isomeric amino­benzoic acids, see: Crocker & Matthews (1911 ▶). For the application of the title compound in dyeing technology, see: Beretta (1926 ▶);. For structural data on N-picryl-substituted anilines, see: Forlani et al. (1992 ▶); Pan et al. (2007 ▶); Smith et al. (2007) ▶; Braun et al. (2008 ▶); Smith et al. (2009 ▶). For diazenyl-protonated salts of aniline yellow, see: Mahmoudkhani & Langer (2001 ▶); Smith et al. (2009 ▶, 2011 ▶).




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