{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T21:49:23Z","timestamp":1740174563528,"version":"3.37.3"},"reference-count":16,"publisher":"International Union of Crystallography (IUCr)","issue":"5","license":[{"start":{"date-parts":[[2017,4,11]],"date-time":"2017-04-11T00:00:00Z","timestamp":1491868800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},{"start":{"date-parts":[[2017,4,11]],"date-time":"2017-04-11T00:00:00Z","timestamp":1491868800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"}],"funder":[{"DOI":"10.13039\/501100003130","name":"Fonds Wetenschappelijk Onderzoek","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003130","id-type":"DOI","asserted-by":"publisher"}]}],"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"],"accepted":{"date-parts":[[2017,3,31]]},"published-print":{"date-parts":[[2017,5,1]]},"abstract":"<jats:p>The title compound, C<jats:sub>17<\/jats:sub>H<jats:sub>12<\/jats:sub>BrN<jats:sub>3<\/jats:sub>O<jats:sub>2<\/jats:sub>, was unexpectedly isolated during an attempt to synthesize pyridodiazepinediones and identified as an oxazolonaphthyridinone derivative. The almost planar oxazolonaphthyridinone ring (r.m.s. deviation = 0.016\u2005\u00c5) makes a dihedral angle of 61.6\u2005(2)\u00b0 with the phenyl ring. In the crystal, columns of molecules stacked along the <jats:italic>a<\/jats:italic> axis are formed by \u03c0\u2013\u03c0 interactions between the six-membered rings of the oxazolonaphthyridone moieties [centroid-to-centroid distances = 3.494\u2005(2)\u20133.906\u2005(3)\u2005\u00c5], which further interact through C\u2014H...\u03c0 contacts with the phenyl rings.<\/jats:p>","DOI":"10.1107\/s2056989017005023","type":"journal-article","created":{"date-parts":[[2017,4,11]],"date-time":"2017-04-11T08:11:27Z","timestamp":1491898287000},"page":"687-690","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Crystal structure of 5-benzyl-8-bromo-2-methyl-1,3-oxazolo[4,5-<i>c<\/i>][1,8]naphthyridin-4(5<i>H<\/i>)-one"],"prefix":"10.1107","volume":"73","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8085-3390","authenticated-orcid":true,"given":"Johannes","family":"Vrijdag","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"An","family":"Van den Bogaert","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Wim","family":"De Borggraeve","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2186-5209","authenticated-orcid":true,"given":"Luc","family":"Van Meervelt","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2017,4,11]]},"reference":[{"key":"rz5210_bb1","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1080\/08893118708081678","volume":"1","author":"Blessing","year":"1987","journal-title":"Crystallogr. Rev."},{"key":"rz5210_bb2","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Cryst."},{"key":"rz5210_bb3","unstructured":"Enraf-Nonius (1989). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands."},{"key":"rz5210_bb4","doi-asserted-by":"crossref","first-page":"553","DOI":"10.1080\/00397918908050699","volume":"19","author":"Gero","year":"1989","journal-title":"Synth. Commun."},{"key":"rz5210_bb5","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Cryst. B"},{"key":"rz5210_bb6","doi-asserted-by":"crossref","first-page":"528","DOI":"10.1055\/s-2002-20959","author":"Hach\u00e9","year":"2002","journal-title":"Synthesis"},{"key":"rz5210_bb7","unstructured":"Ho, P. S., Yoon, D. O., Han, S. Y., Lee, W. I., Kim, J. S., Park, W. S., Ahn, S. O. & Kim, H. J. (2013). WO Patent 048214."},{"key":"rz5210_bb8","doi-asserted-by":"crossref","first-page":"4640","DOI":"10.1002\/ejoc.200800550","author":"Latypov","year":"2008","journal-title":"Eur. J. Org. Chem."},{"key":"rz5210_bb9","doi-asserted-by":"crossref","first-page":"351","DOI":"10.1107\/S0567739468000707","volume":"24","author":"North","year":"1968","journal-title":"Acta Cryst. A"},{"key":"rz5210_bb10","unstructured":"Ratcliffe, A., Huxley, A., Lyth, D., Noonan, G., Kirk, R., Uosis-Martin, M. & Stokes, N. (2015). WO Patent 155549."},{"key":"rz5210_bb11","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Cryst. A"},{"key":"rz5210_bb12","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"rz5210_bb13","doi-asserted-by":"crossref","first-page":"5397","DOI":"10.1002\/ejoc.201000549","author":"Van den Bogaert","year":"2010","journal-title":"Eur. J. Org. Chem."},{"key":"rz5210_bb14","doi-asserted-by":"crossref","first-page":"1465","DOI":"10.1002\/ejoc.201700020","author":"Vrijdag","year":"2017","journal-title":"Eur. J. Org. Chem."},{"key":"rz5210_bb15","doi-asserted-by":"crossref","first-page":"1052","DOI":"10.1021\/ol4000444","volume":"15","author":"Vrijdag","year":"2013","journal-title":"Org. Lett."},{"key":"rz5210_bb16","unstructured":"Washton, A. M. & Zweben, J. E. (2011). Treating Alcohol and Drug Problems in Psychotherapy Practice, p. 47. New York: Guilford Press."}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2017\/05\/00\/rz5210\/rz5210.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2017\/05\/00\/rz5210\/rz5210.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T10:13:23Z","timestamp":1736763203000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989017005023"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,4,11]]},"references-count":16,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2017,5]]}},"alternative-id":["S2056989017005023"],"URL":"https:\/\/doi.org\/10.1107\/s2056989017005023","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989017005023\/rz5210sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989017005023\/rz5210Isup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989017005023\/rz5210Isup3.cml","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"type":"electronic","value":"2056-9890"}],"subject":[],"published":{"date-parts":[[2017,4,11]]},"assertion":[{"value":"Acta Crystallographica Section E: Crystallographic Communications","order":0,"name":"journal","label":"Publication","explanation":{"URL":"http:\/\/journals.iucr.org\/e"},"group":{"name":"general","label":"General"}},{"value":"research communications","order":1,"name":"content_type","label":"Content type","explanation":{"URL":"https:\/\/journals.iucr.org\/e\/services\/notesforauthors.html"},"group":{"name":"general","label":"General"}},{"value":"Available","URL":"https:\/\/scripts.iucr.org\/cgi-bin\/citedin?rz5210","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":"24 March 2017","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"31 March 2017","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"11 April 2017","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?rz5210"}},{"value":"\u00a9 2017 Vrijdag et al.","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"}}]}}