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Updated: May 24, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
4-(4-Amino-phenyl-sulfon-yl)aniline-1,3,5-trinitro-benzene (1/2)
1Faculty of Science and Technology, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia.
Abstract:
The asymmetric unit of the title co-crystalline 1:2 adduct, C(12)H(12)N(2)O(2)·2C(6)H(3)N(3)O(6), contains two independent mol-ecules of bis-(4-amino-phen-yl) sulfone (the drug Dapsone) and four mol-ecules of 1,3,5-trinitro-benzene 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 mol-ecules, the inter-ring dihedral anges are 69.6 (3) and 63.63 (9)°. Aromatic π-π inter-actions are also found between one of the Dapsone aromatic rings and a trinitro-benzene ring [minimum ring centroid separation = 3.596 (3) Å]. A 4-amino-phenyl ring moiety of one of the Dapsone mol-ecules and two nitro groups of a trinitro-benzene are disordered in a 50:50 ratio.
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