{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,5,17]],"date-time":"2025-05-17T14:40:10Z","timestamp":1747492810323,"version":"3.40.5"},"reference-count":22,"publisher":"International Union of Crystallography (IUCr)","issue":"2","license":[{"start":{"date-parts":[[2015,1,24]],"date-time":"2015-01-24T00:00:00Z","timestamp":1422057600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},{"start":{"date-parts":[[2015,1,24]],"date-time":"2015-01-24T00:00:00Z","timestamp":1422057600000},"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":[[2015,2,1]]},"abstract":"<jats:p>Molecules of the title compound, C<jats:sub>14<\/jats:sub>H<jats:sub>18<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>3<\/jats:sub>[systematic name: 5-allyl-5-(hex-3-yn-2-yl)-1-methylpyrimidine-2,4,6(1<jats:italic>H<\/jats:italic>,3<jats:italic>H<\/jats:italic>,5<jats:italic>H<\/jats:italic>)-trione in the (<jats:italic>R<jats:sub>b<\/jats:sub>S<jats:sub>h<\/jats:sub><\/jats:italic>)\/(<jats:italic>S<jats:sub>b<\/jats:sub>R<jats:sub>h<\/jats:sub><\/jats:italic>) racemic form], are connected by mutual N\u2014H...O=C hydrogen bonds in which the carbonyl group at the 2-position of the pyrimidinetrione ring is employed. These interactions result in an inversion dimer which displays a central<jats:italic>R<\/jats:italic><jats:sub>2<\/jats:sub><jats:sup>2<\/jats:sup>(8) ring motif. This dimer is topologically distinct from that of the previously reported (<jats:italic>S<jats:sub>b<\/jats:sub>R<jats:sub>h<\/jats:sub><\/jats:italic>) form, which is, however, also based on an<jats:italic>R<\/jats:italic><jats:sub>2<\/jats:sub><jats:sup>2<\/jats:sup>(8) motif. The methyl group at the 1-position of the pyrimidinetrione ring in the title structure is disordered over two sets of sites in a 0.57\u2005(2):0.43\u2005(2) ratio.<\/jats:p>","DOI":"10.1107\/s205698901500105x","type":"journal-article","created":{"date-parts":[[2015,1,23]],"date-time":"2015-01-23T09:17:12Z","timestamp":1422004632000},"page":"206-209","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["Crystal structure of the \u03b1-racemate of methohexital"],"prefix":"10.1107","volume":"71","author":[{"given":"Thomas","family":"Gelbrich","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ulrich J.","family":"Griesser","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2015,1,24]]},"reference":[{"key":"wm5105_bb1","unstructured":"Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England."},{"key":"wm5105_bb2","doi-asserted-by":"crossref","first-page":"64","DOI":"10.1039\/B914365C","volume":"12","author":"Arlin","year":"2010","journal-title":"CrystEngComm"},{"key":"wm5105_bb3","doi-asserted-by":"crossref","first-page":"7074","DOI":"10.1039\/c1cc11634g","volume":"47","author":"Arlin","year":"2011","journal-title":"Chem. Commun."},{"key":"wm5105_bb4","doi-asserted-by":"crossref","first-page":"1555","DOI":"10.1002\/anie.199515551","volume":"34","author":"Bernstein","year":"1995","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"wm5105_bb5","doi-asserted-by":"crossref","first-page":"2647","DOI":"10.1021\/jp9941413","volume":"104","author":"Beyer","year":"2000","journal-title":"J. Phys. Chem. B"},{"key":"wm5105_bb6","doi-asserted-by":"crossref","first-page":"855","DOI":"10.1002\/ejoc.200390129","author":"Brunner","year":"2003","journal-title":"Eur. J. Org. Chem."},{"key":"wm5105_bb7","doi-asserted-by":"crossref","first-page":"685","DOI":"10.1107\/S0567740875003627","volume":"31","author":"Dideberg","year":"1975","journal-title":"Acta Cryst. B"},{"key":"wm5105_bb8","doi-asserted-by":"crossref","first-page":"256","DOI":"10.1107\/S0108768189012929","volume":"46","author":"Etter","year":"1990","journal-title":"Acta Cryst. B"},{"key":"wm5105_bb9","unstructured":""},{"key":"wm5105_bb10","doi-asserted-by":"crossref","first-page":"o55","DOI":"10.1107\/S0108270109054249","volume":"66","author":"Gelbrich","year":"2010","journal-title":"Acta Cryst. C"},{"key":"wm5105_bb11","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/S0022-3565(25)12877-2","volume":"125","author":"Gibson","year":"1959","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"wm5105_bb12","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1002\/anie.201306438","volume":"53","author":"Groom","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"wm5105_bb13","doi-asserted-by":"crossref","first-page":"o799","DOI":"10.1107\/S1600536805005593","volume":"61","author":"Lewis","year":"2005","journal-title":"Acta Cryst. E"},{"key":"wm5105_bb14","doi-asserted-by":"crossref","first-page":"453","DOI":"10.1107\/S002188980600731X","volume":"39","author":"Macrae","year":"2006","journal-title":"J. Appl. Cryst."},{"key":"wm5105_bb15","doi-asserted-by":"crossref","first-page":"o1004","DOI":"10.1107\/S1600536805007531","volume":"61","author":"Nichol","year":"2005","journal-title":"Acta Cryst. E"},{"key":"wm5105_bb16","doi-asserted-by":"crossref","first-page":"1672","DOI":"10.1107\/S0567740880006887","volume":"36","author":"Py\u017calska","year":"1980","journal-title":"Acta Cryst. B"},{"key":"wm5105_bb17","doi-asserted-by":"crossref","first-page":"6554","DOI":"10.1021\/jm300631e","volume":"55","author":"Savechenkov","year":"2012","journal-title":"J. Med. Chem."},{"key":"wm5105_bb18","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Cryst. A"},{"key":"wm5105_bb19","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"wm5105_bb20","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1107\/S0021889810022120","volume":"43","author":"Westrip","year":"2010","journal-title":"J. Appl. Cryst."},{"key":"wm5105_bb21","first-page":"507","volume":"5","author":"Wilhelm","year":"1976","journal-title":"Cryst. Struct. Commun."},{"key":"wm5105_bb22","doi-asserted-by":"crossref","first-page":"168","DOI":"10.1107\/S0567740873002165","volume":"29","author":"Wunderlich","year":"1973","journal-title":"Acta Cryst. B"}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2015\/02\/00\/wm5105\/wm5105.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2015\/02\/00\/wm5105\/wm5105.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,5,17]],"date-time":"2025-05-17T14:12:36Z","timestamp":1747491156000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S205698901500105X"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,1,24]]},"references-count":22,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2015,2]]}},"alternative-id":["S205698901500105X"],"URL":"https:\/\/doi.org\/10.1107\/s205698901500105x","relation":{},"ISSN":["2056-9890"],"issn-type":[{"type":"electronic","value":"2056-9890"}],"subject":[],"published":{"date-parts":[[2015,1,24]]},"assertion":[{"value":"Acta Crystallographica Section E: Crystallographic Communications","name":"journal","label":"Journal","explanation":{"URL":"http:\/\/journals.iucr.org\/e"}},{"value":"research communications","name":"content_type","label":"Content type","explanation":{"URL":"http:\/\/journals.iucr.org\/e\/services\/notesforauthors.html"}},{"value":"Yes","order":0,"name":"peer_reviewed","label":"Peer reviewed","group":{"name":"peer_review","label":"Peer review"}},{"value":"Single blind","order":1,"name":"review_process","label":"Review process","group":{"name":"peer_review","label":"Peer review"}},{"value":"15 December 2014","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"18 January 2015","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"24 January 2015","order":2,"name":"published_online","label":"Published online","group":{"name":"publication_history","label":"Publication history"}},{"value":"This article has supporting information","name":"supplementary_materials","label":"Supplementary materials","explanation":{"URL":"http:\/\/scripts.iucr.org\/cgi-bin\/sendsup?wm5105"}},{"value":"\u00a9 2015 Gelbrich and Griesser","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}},{"value":"Creative Commons Attribution (CC-BY)","order":1,"name":"license","label":"Licence","explanation":{"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}}]}}