Research Article: 4-(4-Amino­phenyl­sulfon­yl)aniline–1,3,5-trinitro­benzene (1/2)

Date Published: February 01, 2012

Publisher: International Union of Crystallography

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


The asymmetric unit of the title co-crystalline 1:2 adduct, C12H12N2O2·2C6H3N3O6, contains two independent mol­ecules of bis­(4-amino­phen­yl) sulfone (the drug Dapsone) and four mol­ecules of 1,3,5-trinitro­benzene and is extended into a two-dimensional hydrogen-bonded network structure through amino N—H⋯O hydrogen-bonding associations with nitro O-atom acceptors. In the two independent Dapsone mol­ecules, the inter-ring dihedral anges are 69.6 (3) and 63.63 (9)°. Aromatic π–π inter­actions are also found between one of the Dapsone aromatic rings and a trinitro­benzene ring [minimum ring centroid separation = 3.596 (3) Å]. A 4-amino­phenyl ring moiety of one of the Dapsone mol­ecules and two nitro groups of a trinitro­benzene are disordered in a 50:50 ratio.

Partial Text

For drug applications of Dapsone, see: Wilson et al. (1991 ▶). For the structures of Dapsone and its partial hydrate, see: Dickenson et al. (1970 ▶); Kus’mina et al. (1981 ▶). For the deca­rboxylation of 2,4,6-trinitro­benzoic acid and resultant co-crystal adduct structure, see: Smith et al. (2002 ▶).