{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T05:09:48Z","timestamp":1736831388704,"version":"3.33.0"},"reference-count":49,"publisher":"International Union of Crystallography (IUCr)","issue":"11","license":[{"start":{"date-parts":[[2013,10,5]],"date-time":"2013-10-05T00:00:00Z","timestamp":1380931200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2013,10,5]],"date-time":"2013-10-05T00:00:00Z","timestamp":1380931200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst Sect C","Acta Crystallogr C","Acta Crystallogr Sect C","Acta Crystallogr Sect C Cryst Struct Commun"],"published-print":{"date-parts":[[2013,11,15]]},"abstract":"<jats:p>The molecular and supramolecular structures are reported of<jats:italic>N<\/jats:italic>-[2-(pyridin-2-yl)ethyl]methanesulfonamide, C<jats:sub>8<\/jats:sub>H<jats:sub>12<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>S, (I),<jats:italic>N<\/jats:italic>-[2-(pyridin-2-yl)ethyl]benzenesulfonamide, C<jats:sub>13<\/jats:sub>H<jats:sub>14<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>S, (II), and<jats:italic>N<\/jats:italic>-[2-(pyridin-2-yl)ethyl]toluenesulfonamide, C<jats:sub>14<\/jats:sub>H<jats:sub>16<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>S, (III). Although (II) and (III) are almost structurally identical, the N(amide)\u2014C(ethyl)\u2014C(ethyl)\u2014C(pyridinyl) torsion angles for (I) and (II) are more closely comparable, with magnitudes of 175.37\u2005(15)\u00b0 for (I) and 169.04\u2005(19)\u00b0 for (II). This angle decreases dramatically with an additional methyl group in the<jats:italic>para<\/jats:italic>position of the sulfonamide substituent, resulting in a value of 62.9\u2005(2)\u00b0 for (III). In each of the three compounds there is an N\u2014H...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 \u03c0\u2013\u03c0 stacking in the benzene-substituted structure (II), but distorted intramolecular T-shaped \u03c0-stacking in the toluene-substituted structure (III), with a centroid-to-centroid distance of 4.9296\u2005(10)\u2005\u00c5.<\/jats:p>","DOI":"10.1107\/s0108270113025341","type":"journal-article","created":{"date-parts":[[2013,10,4]],"date-time":"2013-10-04T15:09:59Z","timestamp":1380899399000},"page":"1397-1401","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":2,"title":["<i>N<\/i>-[2-(Pyridin-2-yl)ethyl]-derivatives of methane-, benzene- and toluenesulfonamide: prospective ligands for metal coordination"],"prefix":"10.1107","volume":"69","author":[{"given":"Danielle L.","family":"Jacobs","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Benny C.","family":"Chan","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Abby R.","family":"O'Connor","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2013,10,5]]},"reference":[{"key":"yp3050_bb1","doi-asserted-by":"crossref","first-page":"2905","DOI":"10.1021\/ja01264a055","volume":"64","author":"Bell","year":"1942","journal-title":"J. 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