Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 5 (May 2013)

organic compounds

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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