{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T05:11:39Z","timestamp":1736831499959,"version":"3.33.0"},"reference-count":11,"publisher":"International Union of Crystallography (IUCr)","issue":"5","license":[{"start":{"date-parts":[[2014,4,9]],"date-time":"2014-04-09T00:00:00Z","timestamp":1397001600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},{"start":{"date-parts":[[2014,4,9]],"date-time":"2014-04-09T00:00:00Z","timestamp":1397001600000},"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 Struct Rep Online","Acta Crystallogr E","Acta Cryst E","Acta Cryst E Struct Rep Online","Acta Cryst Sect E","Acta Cryst Sect E Struct Rep Online","Acta Crystallogr Sect E","Acta Crystallogr Sect E Struct Rep Online"],"published-print":{"date-parts":[[2014,5,1]]},"abstract":"<jats:p>The title compound, C<jats:sub>25<\/jats:sub>H<jats:sub>34<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>5<\/jats:sub>, was synthesized from 9\u03b1-hydroxyparthenolide (9\u03b1-hydroxy-4,8-dimethyl-12-methylen-3, 14-dioxa-tricyclo[9.3.0.0<jats:sup>2,4<\/jats:sup>]tetradec-7-en-13-one), which in turn was isolated from the chloroform extract of the aerial parts of<jats:italic>Anvillea radiata<\/jats:italic>. The molecule comprises a ten-membered ring fused to a five-membered ring with an additional epoxy ring system fused to the ten-membered ring. The five-membered ring also carries a 4-hydroxyphenyl-piperazin-1-ylmethyl substituent. The ten-membered ring adopts an approximate chair\u2013chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hydroxy group forming the flap. Two C atoms in the phenyl ring and the O atom of the hydroxyl group are disordered over two sites, with an occupancy ratio of 0.53\u2005(5):0.47\u2005(5). An intramolecular O\u2014H...N hydrogen-bond stabilizes the molecular conformation. In the crystal, C\u2014H...O hydrogen bonds link the molecules into zigzag chains running along the<jats:italic>a-<\/jats:italic>axis direction.<\/jats:p>","DOI":"10.1107\/s1600536814007430","type":"journal-article","created":{"date-parts":[[2014,4,8]],"date-time":"2014-04-08T08:26:40Z","timestamp":1396945600000},"page":"o530-o531","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["9\u03b1-Hydroxy-12-{[4-(4-hydroxyphenyl)piperazin-1-yl]methyl}-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0<sup>2,4<\/sup>]tetradec-7-en-13-one"],"prefix":"10.1107","volume":"70","author":[{"given":"Mohamed","family":"Loubidi","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ahmed","family":"Benharref","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lahcen","family":"El Ammari","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mohamed","family":"Saadi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Moha","family":"Berraho","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2014,4,9]]},"reference":[{"key":"sj5394_bb1","doi-asserted-by":"crossref","first-page":"403","DOI":"10.1021\/np960064g","volume":"59","author":"Abdel Sattar","year":"1996","journal-title":"J. Nat. Prod."},{"key":"sj5394_bb2","unstructured":"Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA."},{"key":"sj5394_bb3","doi-asserted-by":"crossref","first-page":"1354","DOI":"10.1021\/ja00839a011","volume":"97","author":"Cremer","year":"1975","journal-title":"J. Am. Chem. Soc."},{"key":"sj5394_bb4","doi-asserted-by":"crossref","first-page":"573","DOI":"10.1016\/j.fitote.2004.06.003","volume":"75","author":"El Hassany","year":"2004","journal-title":"Fitoterapia"},{"key":"sj5394_bb5","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1107\/S0021889812029111","volume":"45","author":"Farrugia","year":"2012","journal-title":"J. Appl. Cryst."},{"key":"sj5394_bb6","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1016\/j.bmc.2005.07.055","volume":"14","author":"Hwang","year":"2006","journal-title":"Bioorg. Med. Chem."},{"key":"sj5394_bb7","doi-asserted-by":"crossref","first-page":"o589","DOI":"10.1107\/S1600536812003662","volume":"68","author":"Moumou","year":"2012","journal-title":"Acta Cryst. E"},{"key":"sj5394_bb8","doi-asserted-by":"crossref","first-page":"4346","DOI":"10.1016\/j.bmcl.2009.05.092","volume":"19","author":"Neelakantan","year":"2009","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"sj5394_bb9","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Cryst. A"},{"key":"sj5394_bb10","doi-asserted-by":"crossref","first-page":"148","DOI":"10.1107\/S090744490804362X","volume":"65","author":"Spek","year":"2009","journal-title":"Acta Cryst. D"},{"key":"sj5394_bb11","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1107\/S0021889810022120","volume":"43","author":"Westrip","year":"2010","journal-title":"J. Appl. Cryst."}],"container-title":["Acta Crystallographica Section E Structure Reports Online"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2014\/05\/00\/sj5394\/sj5394.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2014\/05\/00\/sj5394\/sj5394.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T09:41:15Z","timestamp":1736761275000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S1600536814007430"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,4,9]]},"references-count":11,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2014,5]]}},"alternative-id":["S1600536814007430"],"URL":"https:\/\/doi.org\/10.1107\/s1600536814007430","relation":{},"ISSN":["1600-5368"],"issn-type":[{"type":"electronic","value":"1600-5368"}],"subject":[],"published":{"date-parts":[[2014,4,9]]},"assertion":[{"value":"Acta Crystallographica Section E: Structure Reports Online","name":"journal","label":"Publication","explanation":{"URL":"http:\/\/journals.iucr.org\/e"}},{"value":"organic compounds","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":"24 March 2014","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"3 April 2014","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"9 April 2014","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?sj5394"}},{"value":"\u00a9 2014 Loubidiet 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"}}]}}