Similar sulfonamides with different crystal structures: sulfasymazine and sulfatriazine.
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.
Institut für Pharmazie, Universität Innsbruck, Josef-Moeller-Haus, Innrain 52c, 6020 Innsbruck, Austria. mairi-fiona.haddow@uibk.ac.at
Mairi F
MF
Haddow
Thomas
T
Gelbrich
Ulrich J
UJ
Griesser
D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D015394:Molecular Structure; D013424:Sulfanilamides / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*; D013457:Sulfur Compounds / Q000737:chemistry*; D014227:Triazines / Q000737:chemistry*; D000096926:Benzenesulfonamides
D013424:Sulfanilamides; D013449:Sulfonamides; D013457:Sulfur Compounds; D014227:Triazines; D000096926:Benzenesulfonamides; C005744:sulfasymazine