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.
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 ▶).