Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 5 (May 2013)

organic compounds

ky3031 scheme

Acta Cryst. (2013). C69, 538-543    [ doi:10.1107/S0108270113009487 ]

Proton-transfer compounds with 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (sulfamethazine): the structures and hydrogen bonding in the salts with 5-nitrosalicylic acid and picric acid

G. Smith and U. D. Wermuth

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+-H...Ocarboxylate and N-H...Ocarboxylate hydrogen-bond pairs, giving a cyclic motif [graph set R22(8)]. These heterodimers form separate and different non-associated substructures through aniline N-H...O 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 [pi]-[pi] 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-H...O 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-H...Osulfone hydrogen bond gives one-dimensional chains which extend along a and inter-associate through [pi]-[pi] 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-

hkldisplay filedownload file

Structure factor file (CIF format) (394.2 kbytes)
[ doi:10.1107/S0108270113009487/ky3031Isup2.hkl ]
Contains datablock I

hkldisplay filedownload file

Structure factor file (CIF format) (204.4 kbytes)
[ doi:10.1107/S0108270113009487/ky3031IIsup3.hkl ]
Contains datablock II


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