{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T21:49:32Z","timestamp":1740174572280,"version":"3.37.3"},"reference-count":22,"publisher":"International Union of Crystallography (IUCr)","issue":"12","license":[{"start":{"date-parts":[[2017,11,21]],"date-time":"2017-11-21T00:00:00Z","timestamp":1511222400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},{"start":{"date-parts":[[2017,11,21]],"date-time":"2017-11-21T00:00:00Z","timestamp":1511222400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr E Cryst Commun","Acta Cryst E","Acta Cryst Sect E","Acta Crystallogr E","Acta Crystallogr Sect E","Acta Cryst E Cryst Commun","Acta Cryst Sect E Cryst Commun"],"published-print":{"date-parts":[[2017,12,1]]},"abstract":"<jats:p>The molecule of buthalital, (I) [systematic name: 5-(2-methylpropyl)-5-(prop-2-en-1-yl)-2-sulfanylidene-1,3-diazinane-4,6-dione], C<jats:sub>11<\/jats:sub>H<jats:sub>16<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>S, exhibits a planar pyrimidine ring, whereas the pyrimidine ring of methitural, (II) [systematic name: 5-(1-methylbutyl)-5-[2-(methylsulfanyl)ethyl]-2-sulfanylidene-1,3-diazinane-4,6-dione], C<jats:sub>12<\/jats:sub>H<jats:sub>20<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>S<jats:sub>2<\/jats:sub>, is slightly puckered. (I) and (II) contain the same hydrogen-bonded chain structure in which each molecule is connected,<jats:italic>via<\/jats:italic>four N\u2014H...O=C hydrogen bonds, to two other molecules, resulting in a hydrogen-bonded chain displaying a sequence of<jats:italic>R<\/jats:italic><jats:sub>2<\/jats:sub><jats:sup>2<\/jats:sup>(8) rings. The same type of N\u2014H...O=C hydrogen-bonded chain has previously been found in several 5,5-disubstituted derivatives of barbituric acid which are chemically closely related to (I) and (II).<\/jats:p>","DOI":"10.1107\/s205698901701653x","type":"journal-article","created":{"date-parts":[[2017,11,21]],"date-time":"2017-11-21T10:17:53Z","timestamp":1511259473000},"page":"1908-1912","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Buthalital and methitural \u2013 5,5-substituted derivatives of 2-thiobarbituric acid forming the same type of hydrogen-bonded chain"],"prefix":"10.1107","volume":"73","author":[{"given":"Thomas","family":"Gelbrich","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1318-9020","authenticated-orcid":true,"given":"Ulrich J.","family":"Griesser","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2017,11,21]]},"reference":[{"key":"dx2002_bb1","doi-asserted-by":"crossref","first-page":"1555","DOI":"10.1002\/anie.199515551","volume":"34","author":"Bernstein","year":"1995","journal-title":"Angew. 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