Supramolecular structures of three isomeric 4-(methylphenylamino)pyridine-3-sulfonamides.
The structures of the three title isomers, namely 4-(2-methylanilino)pyridine-3-sulfonamide, (I), 4-(3-methylanilino)pyridine-3-sulfonamide, (II), and 4-(4-methylanilino)pyridine-3-sulfonamide, (III), all C(12)H(13)N(3)O(2)S, differ in their hydrogen-bonding arrangements. In all three molecules, the conformation of the 4-aminopyridine-3-sulfonamide moiety is conserved by an intramolecular N-H...O hydrogen bond and a C-H...O interaction. In the supramolecular structures of all three isomers, similar C(6) chains are formed via intermolecular N-H...N hydrogen bonds. N-H...O hydrogen bonds lead to C(4) chains in (I), and to R(2)(2)(8) centrosymmetric dimers in (II) and (III). In each isomer, the overall effect of all hydrogen bonds is to form layer structures.
Kosutić Hulita
Nada
N
PLIVA Research and Development Ltd, Prilaz baruna Filipovića 29, HR-10000 Zagreb, Croatia.
Danilovski
Aleksandar
A
Filić
Darko
D
Marinković
Marina
M
Mestrović
Ernest
E
Dumić
Miljenko
M
D003460:Crystallization; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry*
D013449:Sulfonamides