{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,27]],"date-time":"2026-08-27T19:44:56Z","timestamp":1787859896955,"version":"build-2784847793"},"reference-count":0,"publisher":"International Union of Crystallography (IUCr)","issue":"4","license":[{"start":{"date-parts":[[2006,7,12]],"date-time":"2006-07-12T00:00:00Z","timestamp":1152662400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},{"start":{"date-parts":[[2006,7,12]],"date-time":"2006-07-12T00:00:00Z","timestamp":1152662400000},"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 B Struct Sci","Acta Cryst B","Acta Cryst Sect B","Acta Crystallogr B","Acta Crystallogr Sect B","Acta Crystallogr Sect B Struct Sci"],"accepted":{"date-parts":[[2006,3,29]]},"published-print":{"date-parts":[[2006,8,1]]},"abstract":"<jats:p>The structures of four selenium analogues of the antithyroid drug 6-<jats:italic>n<\/jats:italic>-propyl-2-thiouracil [systematic name: 2,3-dihydro-6-<jats:italic>n<\/jats:italic>-propyl-2-thioxopyrimidin-4(1<jats:italic>H<\/jats:italic>)-one], namely 6-methyl-2-selenouracil, C<jats:sub>5<\/jats:sub>H<jats:sub>6<\/jats:sub>N<jats:sub>2<\/jats:sub>OSe (1), 6-ethyl-2-selenouracil, C<jats:sub>6<\/jats:sub>H<jats:sub>8<\/jats:sub>N<jats:sub>2<\/jats:sub>OSe (2), 6-<jats:italic>n<\/jats:italic>-propyl-2-selenouracil, C<jats:sub>7<\/jats:sub>H<jats:sub>10<\/jats:sub>N<jats:sub>2<\/jats:sub>OSe (3), and 6-isopropyl-2-selenouracil, C<jats:sub>7<\/jats:sub>H<jats:sub>10<\/jats:sub>N<jats:sub>2<\/jats:sub>OSe (4), are described, along with that of the dichloromethane monosolvate of 6-isopropyl-2-selenouracil, C<jats:sub>7<\/jats:sub>H<jats:sub>10<\/jats:sub>N<jats:sub>2<\/jats:sub>OSe\u00b7CH<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub> (4\u00b7CH<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub>). The extended structure of (1) is a two-dimensional sheet of topology 6<jats:sup>3<\/jats:sup> with a brick-wall architecture. The extended structures of (2) and (4) are analogous, being based on a chain of eight-membered <jats:italic>R<\/jats:italic>\n                  <jats:sub>8<\/jats:sub>\n                  <jats:sup>6<\/jats:sup>(32) hydrogen-bonded rings. In (3) and (4\u00b7CH<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub>), <jats:italic>R<\/jats:italic>\n                  <jats:sub>2<\/jats:sub>\n                  <jats:sup>2<\/jats:sup>(8) hydrogen bonding links molecules into chains. 6-<jats:italic>n<\/jats:italic>-Propyl-2-selenouracil\u00b7I<jats:sub>2<\/jats:sub>, C<jats:sub>7<\/jats:sub>H<jats:sub>10<\/jats:sub>N<jats:sub>2<\/jats:sub>OSe\u00b7I<jats:sub>2<\/jats:sub> (7), is a charge-transfer complex with a `spoke' structure, the extended structure of which is based on a linear chain formed principally by intermolecular N\u2014H...O hydrogen bonds. Re-crystallization of 6-ethyl-2-selenouracil or (7) from acetone gave crystals of the diselenides [<jats:italic>N<\/jats:italic>-(6\u2032-ethyl-4\u2032-pyrimidone)(6-ethyl-2-selenouracil)<jats:sub>2<\/jats:sub>(Se\u2014Se)]\u00b72H<jats:sub>2<\/jats:sub>O (9\u00b72H<jats:sub>2<\/jats:sub>O) or [<jats:italic>N<\/jats:italic>-(6\u2032-<jats:italic>n<\/jats:italic>-propyl-4\u2032-pyrimidone)(6-<jats:italic>n<\/jats:italic>-propyl-2-selenouracil)<jats:sub>2<\/jats:sub>(Se\u2014Se)] (10), respectively: these have similar extended chain structures formed <jats:italic>via<\/jats:italic> N\u2014H...O and C\u2014H...O hydrogen bonds, stacked to give two-dimensional sheets. Re-crystallization of (7) from methanol\/acetonitrile led <jats:italic>via<\/jats:italic> deselenation to the formation of crystals of 6-<jats:italic>n<\/jats:italic>-propyl-2-uracil (11), in which six symmetry-related molecules combine to form a six-membered <jats:italic>R<\/jats:italic>\n                  <jats:sub>6<\/jats:sub>\n                  <jats:sup>6<\/jats:sup>(24) hydrogen-bonded ring, with each pair of molecules linked by an <jats:italic>R<\/jats:italic>\n                  <jats:sub>2<\/jats:sub>\n                  <jats:sup>2<\/jats:sup>(8) motif.<\/jats:p>","DOI":"10.1107\/s0108768106011426","type":"journal-article","created":{"date-parts":[[2006,7,13]],"date-time":"2006-07-13T13:20:29Z","timestamp":1152796829000},"page":"580-591","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":18,"title":["Structural characterization of selenium and selenium-diiodine analogues of the antithyroid drug 6-<i>n<\/i>-propyl-2-thiouracil and its alkyl derivatives"],"prefix":"10.1107","volume":"62","author":[{"given":"Constantinos D.","family":"Antoniadis","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander J.","family":"Blake","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sotiris K.","family":"Hadjikakou","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nick","family":"Hadjiliadis","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter","family":"Hubberstey","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin","family":"Schr\u00f6der","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claire","family":"Wilson","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2006,7,12]]},"container-title":["Acta Crystallographica Section B Structural Science"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/b\/issues\/2006\/04\/00\/so5003\/so5003.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/b\/issues\/2006\/04\/00\/so5003\/so5003.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,11]],"date-time":"2025-01-11T14:15:06Z","timestamp":1736604906000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S0108768106011426"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2006,7,12]]},"references-count":0,"journal-issue":{"issue":"4","published-print":{"date-parts":[[2006,8]]}},"alternative-id":["S0108768106011426"],"URL":"https:\/\/doi.org\/10.1107\/s0108768106011426","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S0108768106011426\/so5003sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S0108768106011426\/so50031sup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S0108768106011426\/so50032sup3.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S0108768106011426\/so50033sup4.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S0108768106011426\/so50034sup5.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S0108768106011426\/so50034.CH2Cl2sup6.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S0108768106011426\/so50037sup7.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S0108768106011426\/so50039sup8.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S0108768106011426\/so500310sup9.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S0108768106011426\/so500311sup10.hkl","asserted-by":"subject"}]},"ISSN":["0108-7681"],"issn-type":[{"value":"0108-7681","type":"print"}],"subject":[],"published":{"date-parts":[[2006,7,12]]},"assertion":[{"value":"Acta 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