{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T05:12:26Z","timestamp":1736831546538,"version":"3.33.0"},"reference-count":22,"publisher":"International Union of Crystallography (IUCr)","issue":"3","license":[{"start":{"date-parts":[[2013,2,16]],"date-time":"2013-02-16T00:00:00Z","timestamp":1360972800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2013,2,16]],"date-time":"2013-02-16T00:00:00Z","timestamp":1360972800000},"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":[[2013,3,15]]},"abstract":"<jats:p>The molecular conformations of three<jats:italic>N<\/jats:italic>-alkyl-2-(methylsulfanyl)nicotinamide derivatives, namely<jats:italic>N<\/jats:italic>-cyclohexyl-2-(methylsulfanyl)nicotinamide, C<jats:sub>13<\/jats:sub>H<jats:sub>18<\/jats:sub>N<jats:sub>2<\/jats:sub>OS, (I),<jats:italic>N<\/jats:italic>-isopropyl-2-(methylsulfanyl)nicotinamide, C<jats:sub>10<\/jats:sub>H<jats:sub>14<\/jats:sub>N<jats:sub>2<\/jats:sub>OS, (II), in which there are two molecules in the asymmetric unit which were chosen to form a hydrogen-bonded pair, and<jats:italic>N<\/jats:italic>-(2-hydroxyethyl)-2-(methylsulfanyl)nicotinamide dihydrate, C<jats:sub>9<\/jats:sub>H<jats:sub>12<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>S\u00b72H<jats:sub>2<\/jats:sub>O, (III), are compared with those of four unsubstituted<jats:italic>N<\/jats:italic>-alkylnicotinamide compounds. The substituted compounds show a higher degree of torsion of the pyridine ring with respect to the amide group than do the unsubstituted compounds, with dihedral angles in the range 40\u201360\u00b0 for the former and 20\u201335\u00b0 for the latter. In (I) and (II), the supramolecular structure is defined by amide-N to carbonyl-O chains. In (III), the nicotinamide molecules are linked by hydrogen bonds to two water molecules resulting in two linked chains of rings which form the three-dimensional network.<\/jats:p>","DOI":"10.1107\/s0108270113004344","type":"journal-article","created":{"date-parts":[[2013,2,15]],"date-time":"2013-02-15T17:36:26Z","timestamp":1360949786000},"page":"293-298","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Three 2-(methysulfanyl)nicotinamides"],"prefix":"10.1107","volume":"69","author":[{"given":"Ligia R.","family":"Gomes","sequence":"first","affiliation":[]},{"given":"John Nicolson","family":"Low","sequence":"additional","affiliation":[]},{"given":"James L.","family":"Wardell","sequence":"additional","affiliation":[]},{"given":"Alessandra C.","family":"Pinheiro","sequence":"additional","affiliation":[]},{"given":"Thais C. N. de","family":"Mendon\u00e7a","sequence":"additional","affiliation":[]},{"given":"Marcus V. 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