Acta Crystallographica Section C

Crystal Structure Communications

Volume 64, Part 6 (June 2008)

organic compounds

em3013 scheme

Acta Cryst. (2008). C64, o309-o312 [ doi:10.1107/S0108270108011888 ]

Similar sulfonamides with different crystal structures: sulfasymazine and sulfatriazine

M. F. Haddow, T. Gelbrich and U. J. Griesser

Abstract: The crystal structures of 4-amino-N-(4,6-diethyl-1,3,5-triazin-2-yl)benzenesulfonamide, C₁₃H₁₇N₅O₂S, and 4-amino-N-(4,6-dimethoxy-1,3,5-triazin-2-yl)benzenesulfonamide, C₁₁H₁₃N₅O₄S, also known as sulfasymazine and sulfatriazine, respectively, are dominated by hydrogen-bond interactions. All three potential hydrogen-bond donors are employed in each case, resulting in a three-dimensional network for sulfasymazine, while an entirely different hydrogen-bonded layer structure is obtained for sulfatriazine. This study demonstrates the versatile nature of the hydrogen-bonding capabilities in sulfonamides, even in structurally very similar molecules.

Formula: C₁₃H₁₇N₅O₂S and C₁₁H₁₃N₅O₄S