title: 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 of N-[2-(pyridin-2-yl)ethyl]methanesulfonamide, C8H12N2O2S, (I), N-[2-(pyridin-2-yl)ethyl]benzenesulfonamide, C13H14N2O2S, (II), and N-[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 the para position 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.
authors.affiliation: Department of Chemistry, Biochemistry and Physics, Rider University, 2083 Lawrenceville Road, Lawrenceville, NJ 08648, USA.
authors.forename: Danielle L
authors.initials: DL
authors.lastname: Jacobs
authors.forename: Benny C
authors.initials: BC
authors.lastname: Chan
authors.forename: Abby R
authors.initials: AR
authors.lastname: O'Connor
mesh_terms: D001554:Benzene / Q000737:chemistry*; D056831:Coordination Complexes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008024:Ligands; D008697:Methane / Q000737:chemistry*; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*; D000096926:Benzenesulfonamides
chemical_list: D001554:Benzene; D056831:Coordination Complexes; D008024:Ligands; D008697:Methane; D011725:Pyridines; D013449:Sulfonamides; C586917:N-(2-(pyridin-2-yl)ethyl)benzenesulfonamide; D000096926:Benzenesulfonamides; C586916:N-(2-(pyridin-2-yl)ethyl)methanesulfonamide; C586918:N-(2-(pyridin-2-yl)ethyl)toluenesulfonamide
keywords: 2-vinylpyridine; N-[2-(pyridin-2-yl)ethyl]-substituted sulfonamides; crystal structure; sulfonamides