{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T18:16:19Z","timestamp":1790187379378,"version":"4.1.0"},"reference-count":0,"publisher":"International Union of Crystallography (IUCr)","issue":"10","license":[{"start":{"date-parts":[[2004,9,4]],"date-time":"2004-09-04T00:00:00Z","timestamp":1094256000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},{"start":{"date-parts":[[2004,9,4]],"date-time":"2004-09-04T00:00:00Z","timestamp":1094256000000},"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 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"],"accepted":{"date-parts":[[2004,7,19]]},"published-print":{"date-parts":[[2004,10,1]]},"abstract":"<jats:p>The structure of hydantoin (imidazolidine-2,4-dione), C<jats:sub>3<\/jats:sub>H<jats:sub>4<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>, has been determined from a twinned crystal. The two carbonyl bond lengths are nearly equal, even though one of them adjoins electron-donating NH groups to either side while the other is adjacent to only one. <jats:italic>Ab initio<\/jats:italic> molecular-orbital calculations yield more negative L\u00f6wdin charge on the former than the latter. Hydantoin molecules form two chains linked by N\u2014H...O hydrogen bonds, from which inversion centres create a `chain of rings'. Out of 50 hydantoin moieties in 49 independent molecules of hydantoin derivatives in the Cambridge Structural Database [Version 5.25; Allen (2002). <jats:italic>Acta Cryst<\/jats:italic>. B<jats:bold>58<\/jats:bold>, 380\u2013388], five show this arrangement, six are a variant using the same O atom twice, five form a chain of edge-fused 12-membered hydrogen-bonded rings, and all but three of the remainder have one eight-membered ring and\/or one chain connecting their hydantoin rings.<\/jats:p>","DOI":"10.1107\/s0108270104017706","type":"journal-article","created":{"date-parts":[[2004,10,5]],"date-time":"2004-10-05T15:39:40Z","timestamp":1096990780000},"page":"o714-o717","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":35,"title":["Hydantoin and hydrogen-bonding patterns in hydantoin derivatives"],"prefix":"10.1107","volume":"60","author":[{"given":"Fang-Lei","family":"Yu","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Carl H.","family":"Schwalbe","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David J.","family":"Watkin","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2004,9,4]]},"container-title":["Acta Crystallographica Section C Crystal Structure Communications"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/c\/issues\/2004\/10\/00\/gd1332\/gd1332.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/c\/issues\/2004\/10\/00\/gd1332\/gd1332.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,9,13]],"date-time":"2024-09-13T12:19:09Z","timestamp":1726229949000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S0108270104017706"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2004,9,4]]},"references-count":0,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2004,10]]}},"alternative-id":["S0108270104017706"],"URL":"https:\/\/doi.org\/10.1107\/s0108270104017706","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S0108270104017706\/gd1332sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S0108270104017706\/gd1332Isup2.hkl","asserted-by":"subject"}]},"ISSN":["0108-2701"],"issn-type":[{"value":"0108-2701","type":"print"}],"subject":[],"published":{"date-parts":[[2004,9,4]]},"assertion":[{"value":"Acta Crystallographica Section C: Crystal Structure Communications","order":0,"name":"journal","label":"Publication","explanation":{"URL":"https:\/\/journals.iucr.org\/c"},"group":{"name":"general","label":"General"}},{"value":"organic compounds","order":1,"name":"content_type","label":"Content type","explanation":{"URL":"https:\/\/journals.iucr.org\/c\/services\/notesforauthors.html"},"group":{"name":"general","label":"General"}},{"value":"Available","URL":"https:\/\/scripts.iucr.org\/cgi-bin\/citedin?gd1332","order":2,"name":"article_metrics","label":"Article metrics","group":{"name":"general","label":"General"}},{"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":"21 June 2004","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"19 July 2004","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"4 September 2004","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":"https:\/\/scripts.iucr.org\/cgi-bin\/sendsup?gd1332"}},{"value":"\u00a9 2004 International Union of Crystallography","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},"group":{"name":"copyright_and_licensing","label":"Copyright and licencing"}}]}}