N-[2-(Pyridin-2-yl)ethyl]-derivatives of methane-, benzene- and toluenesulfonamide: prospective ligands for metal coordination

Abstract

The molecular and supramolecular structures are reported ofN-[2-(pyridin-2-yl)ethyl]methanesulfonamide, C8H12N2O2S, (I),N-[2-(pyridin-2-yl)ethyl]benzenesulfonamide, C13H14N2O2S, (II), andN-[2-(pyridin-2-yl)ethyl]toluenesulfonamide, C14H16N2O2S, (III). Although (II) and (III) are almost structurally identical, the N(amide)—C(ethyl)—C(ethyl)—C(pyridinyl) torsion angles for (I) and (II) are more closely comparable, with magnitudes of 175.37 (15)° for (I) and 169.04 (19)° for (II). This angle decreases dramatically with an additional methyl group in theparaposition of the sulfonamide substituent, resulting in a value of 62.9 (2)° for (III). In each of the three compounds there is an N—H...N hydrogen bond between the sulfonamide of one molecule and the pyridine N atom of a neighbor. Compound (I) forms hydrogen-bonded dimers, (II) uses its hydrogen bonding to connect supramolecular layers, and the hydrogen bonding of (III) connects linear chains to form layers. For arene-substituted (II) and (III), the different conformations afforded by the variable dihedral angles promote intermolecular π–π stacking in the benzene-substituted structure (II), but distorted intramolecular T-shaped π-stacking in the toluene-substituted structure (III), with a centroid-to-centroid distance of 4.9296 (10) Å.