Abstract
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.
Highlights
The asymmetric unit of the title co-crystalline 1:2 adduct, C12H12N2O22C6H3N3O6, contains two independent molecules of bis(4-aminophenyl) sulfone and four molecules of 1,3,5-trinitrobenzene and is extended into a twodimensional hydrogen-bonded network structure through amino N—H O hydrogen-bonding associations with nitro
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
Our attempted preparation of Dapsone with 2,4,6-trinitrobenzoic acid (TNBA) resulted in the title compound, the TNB adduct molecules resulting from the common facile decarboxylation of the parent acid (Smith et al, 2002)
Summary
The asymmetric unit of the title co-crystalline 1:2 adduct, C12H12N2O22C6H3N3O6, 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 twodimensional hydrogen-bonded network structure through amino N—H O hydrogen-bonding associations with nitro. In the two independent Dapsone molecules, the inter-ring dihedral anges are 69.6 (3) and 63.63 (9). Aromatic – interactions are 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
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