Acta Cryst. (2013). C69, 538-543 [ doi:10.1107/S0108270113009487 ]
Abstract: The structures of the anhydrous proton-transfer compounds of the sulfa drug sulfamethazine with 5-nitrosalicylic acid and picric acid, namely 2-(4-aminobenzenesulfonamido)-4,6-dimethylpyrimidinium 2-hydroxy-5-nitrobenzoate, C12H15N4O2S+·C7H4NO4-, (I), and 2-(4-aminobenzenesulfonamido)-4,6-dimethylpyrimidinium 2,4,6-trinitrophenolate, C12H15N4O2S+·C6H2N3O7-, (II), respectively, have been determined. In the asymmetric unit of (I), there are two independent but conformationally similar cation-anion heterodimer pairs which are formed through duplex intermolecular N+-HOcarboxylate and N-HOcarboxylate hydrogen-bond pairs, giving a cyclic motif [graph set R22(8)]. These heterodimers form separate and different non-associated substructures through aniline N-HO hydrogen bonds, one one-dimensional, involving carboxylate O-atom acceptors, the other two-dimensional, involving both carboxylate and hydroxy O-atom acceptors. The overall two-dimensional structure is stabilized by - interactions between the pyrimidinium ring and the 5-nitrosalicylate ring in both heterodimers [minimum ring-centroid separation = 3.4580 (8) Å]. For picrate (II), the cation-anion interaction involves a slightly asymmetric chelating N-HO R21(6) hydrogen-bonding association with the phenolate O atom, together with peripheral conjoint R12(6) interactions between the same N-H groups and O atoms of the ortho-related nitro groups. An inter-unit amine N-HOsulfone hydrogen bond gives one-dimensional chains which extend along a and inter-associate through - interactions between the pyrimidinium rings [centroid-centroid separation = 3.4752 (9) Å]. The two structures reported here now bring to a total of four the crystallographically characterized examples of proton-transfer salts of sulfamethazine with strong organic acids.
Formula: C12H15N4O2S+·C7H4NO5- and C12H15N4O2S+·C6H2N3O7-
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