{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T05:12:01Z","timestamp":1736831521846,"version":"3.33.0"},"reference-count":14,"publisher":"International Union of Crystallography (IUCr)","issue":"4","license":[{"start":{"date-parts":[[2014,3,29]],"date-time":"2014-03-29T00:00:00Z","timestamp":1396051200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},{"start":{"date-parts":[[2014,3,29]],"date-time":"2014-03-29T00:00:00Z","timestamp":1396051200000},"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":[[2014,4,15]]},"abstract":"<jats:p>The title compound, C<jats:sub>25<\/jats:sub>H<jats:sub>33<\/jats:sub>BrN<jats:sub>2<\/jats:sub>O<jats:sub>4<\/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 was isolated from the chloroform extract of the aerial parts of<jats:italic>Anvillea radiata<\/jats:italic>. The molecule is built up from two fused five- and ten-membered rings with an additional epoxy ring system and a bromophenylpiperazine group as a substituent. The ten-membered ring adopts an approximate chair\u2013chair\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. An intramolecular O\u2014H...N hydrogen bond stabilizes the molecular conformation. The crystal packing features C\u2014H...O hydrogen bonds, which link the molecules into zigzag chains running along the<jats:italic>b-<\/jats:italic>axis direction.<\/jats:p>","DOI":"10.1107\/s1600536814006473","type":"journal-article","created":{"date-parts":[[2014,3,28]],"date-time":"2014-03-28T21:30:27Z","timestamp":1396042227000},"page":"o497-o498","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["12-{[4-(4-Bromophenyl)piperazin-1-yl]methyl}-9\u03b1-hydroxy-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":[[2014,3,29]]},"reference":[{"key":"bt6970_bb1","doi-asserted-by":"crossref","first-page":"403","DOI":"10.1021\/np960064g","volume":"59","author":"Abdel Sattar","year":"1996","journal-title":"J. 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