{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T05:09:32Z","timestamp":1736831372012,"version":"3.33.0"},"reference-count":18,"publisher":"International Union of Crystallography (IUCr)","issue":"11","license":[{"start":{"date-parts":[[2013,10,31]],"date-time":"2013-10-31T00:00:00Z","timestamp":1383177600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2013,10,31]],"date-time":"2013-10-31T00:00:00Z","timestamp":1383177600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"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"],"published-print":{"date-parts":[[2013,11,15]]},"abstract":"<jats:p>The absolute configuration has been established of the enantiopure<jats:italic>anti<\/jats:italic>-head-to-head cyclodimer of anthracene-2-carboxylic acid (AC) cocrystallized with L-propinol and dichloromethane [systematic name: (<jats:italic>S<\/jats:italic>)-2-(hydroxymethyl)pyrrolidin-1-ium (5<jats:italic>R<\/jats:italic>,6<jats:italic>S<\/jats:italic>,11<jats:italic>R<\/jats:italic>,12<jats:italic>S<\/jats:italic>)-8-carboxy-5,6,11,12-tetrahydro-5,12:6,11-bis([1,2]benzeno)dibenzo[<jats:italic>a<\/jats:italic>,<jats:italic>e<\/jats:italic>][8]annulene-2-carboxylate dichloromethane monosolvate], C<jats:sub>5<\/jats:sub>H<jats:sub>12<\/jats:sub>NO<jats:sup>+<\/jats:sup>\u00b7C<jats:sub>30<\/jats:sub>H<jats:sub>19<\/jats:sub>O<jats:sub>4<\/jats:sub><jats:sup>\u2212<\/jats:sup>\u00b7CH<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub>. In the crystal structure, the AC dimer interacts with L-prolinol through a nine-membered hydrogen-bonded ring [<jats:italic>R<\/jats:italic><jats:sub>2<\/jats:sub><jats:sup>2<\/jats:sup>(9)], while the dichloromethane molecule is incorporated to fill the void space. The absolute configuration determined in this study verifies a recent assignment made by comparing theoretical<jats:italic>versus<\/jats:italic>experimental circular dichroism spectra.<\/jats:p>","DOI":"10.1107\/s0108270113028461","type":"journal-article","created":{"date-parts":[[2013,10,31]],"date-time":"2013-10-31T17:37:15Z","timestamp":1383241035000},"page":"1411-1413","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":3,"title":["Absolute configuration determination of the<i>anti<\/i>-head-to-head photocyclodimer of anthracene-2-carboxylic acid through cocrystallization with<scp>L<\/scp>-prolinol"],"prefix":"10.1107","volume":"69","author":[{"given":"Yuko","family":"Kawanami","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hidekazu","family":"Tanaka","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jun-ichi","family":"Mizoguchi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nobuko","family":"Kanehisa","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gaku","family":"Fukuhara","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masaki","family":"Nishijima","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tadashi","family":"Mori","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yoshihisa","family":"Inoue","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2013,10,31]]},"reference":[{"key":"sk3506_bb1","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1021\/cr00017a008","volume":"93","author":"Becker","year":"1993","journal-title":"Chem. Rev."},{"key":"sk3506_bb18","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":"sk3506_bb2","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1039\/a801821i","volume":"29","author":"Bouas-Laurent","year":"2000","journal-title":"Chem. Soc. Rev."},{"key":"sk3506_bb3","doi-asserted-by":"crossref","first-page":"248","DOI":"10.1039\/b006013p","volume":"30","author":"Bouas-Laurent","year":"2001","journal-title":"Chem. Soc. Rev."},{"key":"sk3506_bb4","doi-asserted-by":"crossref","first-page":"876","DOI":"10.1107\/S0108767383001762","volume":"39","author":"Flack","year":"1983","journal-title":"Acta Cryst. A"},{"key":"sk3506_bb5","doi-asserted-by":"crossref","first-page":"9156","DOI":"10.1039\/c2cc34880b","volume":"48","author":"Fukuhara","year":"2012","journal-title":"Chem. Commun."},{"key":"sk3506_bb6","doi-asserted-by":"crossref","first-page":"7908","DOI":"10.1021\/jo901792t","volume":"74","author":"Kawanami","year":"2009","journal-title":"J. Org. Chem."},{"key":"sk3506_bb7","doi-asserted-by":"crossref","first-page":"6051","DOI":"10.1021\/ol062501g","volume":"8","author":"Mizoguchi","year":"2006","journal-title":"Org. Lett."},{"key":"sk3506_bb8","doi-asserted-by":"crossref","first-page":"966","DOI":"10.1021\/ja016238k","volume":"125","author":"Nakamura","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"sk3506_bb9","doi-asserted-by":"crossref","first-page":"3478","DOI":"10.1021\/ja068475z","volume":"129","author":"Nishijima","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"sk3506_bb10","doi-asserted-by":"crossref","first-page":"786","DOI":"10.1107\/S0021889807029238","volume":"40","author":"Palatinus","year":"2007","journal-title":"J. Appl. Cryst."},{"key":"sk3506_bb11","first-page":"1973","volume":"11","author":"Qui","year":"2009","journal-title":"Org. Lett."},{"key":"sk3506_bb12","unstructured":"Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan."},{"key":"sk3506_bb13","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Cryst. A"},{"key":"sk3506_bb14","doi-asserted-by":"crossref","first-page":"7492","DOI":"10.1021\/ja034641g","volume":"125","author":"Wada","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"sk3506_bb15","doi-asserted-by":"crossref","first-page":"4990","DOI":"10.1021\/ja300522y","volume":"134","author":"Wakai","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"sk3506_bb16","doi-asserted-by":"crossref","first-page":"158","DOI":"10.1107\/S0108767383000252","volume":"39","author":"Walker","year":"1983","journal-title":"Acta Cryst. A"},{"key":"sk3506_bb17","doi-asserted-by":"crossref","first-page":"13786","DOI":"10.1021\/ja202020x","volume":"133","author":"Yang","year":"2011","journal-title":"J. Am. Chem. Soc."}],"container-title":["Acta Crystallographica Section C Crystal Structure Communications"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/c\/issues\/2013\/11\/00\/sk3506\/sk3506.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/c\/issues\/2013\/11\/00\/sk3506\/sk3506.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T09:20:25Z","timestamp":1736760025000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S0108270113028461"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,10,31]]},"references-count":18,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2013,11]]}},"alternative-id":["S0108270113028461"],"URL":"https:\/\/doi.org\/10.1107\/s0108270113028461","relation":{},"ISSN":["0108-2701"],"issn-type":[{"type":"print","value":"0108-2701"}],"subject":[],"published":{"date-parts":[[2013,10,31]]},"assertion":[{"value":"Acta Crystallographica Section C: Crystal Structure Communications","name":"journal","label":"Journal","explanation":{"URL":"http:\/\/journals.iucr.org\/c"}},{"value":"organic compounds","name":"content_type","label":"Content type","explanation":{"URL":"http:\/\/journals.iucr.org\/c\/issues\/2011\/01\/00\/me0438\/index.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":"9 August 2013","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"16 October 2013","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"31 October 2013","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?sk3506"}},{"value":"\u00a9 2013 International Union of Crystallography","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},"group":{"name":"copyright_and_licensing","label":"Copyright and licencing"}}]}}