{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T05:18:33Z","timestamp":1736831913757,"version":"3.33.0"},"reference-count":22,"publisher":"International Union of Crystallography (IUCr)","issue":"12","license":[{"start":{"date-parts":[[2019,11,25]],"date-time":"2019-11-25T00:00:00Z","timestamp":1574640000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2019,11,25]],"date-time":"2019-11-25T00:00:00Z","timestamp":1574640000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["CHE-1726630","CHE-0650456"],"award-info":[{"award-number":["CHE-1726630","CHE-0650456"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr C Struct Chem","Acta Crystallogr C","Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst C Struct Chem","Acta Cryst Sect C","Acta Cryst Sect C Struct Chem","Acta Crystallogr Sect C","Acta Crystallogr Sect C Struct Chem","Acta Crystallogr Sect C Cryst Struct Commun"],"accepted":{"date-parts":[[2019,11,6]]},"published-print":{"date-parts":[[2019,12,1]]},"abstract":"<jats:p>The reactivities of two 20-membered macrocyclic ligands, each containing two N-heterocyclic carbene (NHC) and two amine groups, towards [IrCl(COD)]<jats:sub>2<\/jats:sub> (COD is cycloocta-1,5-diene) were investigated. Macrocycles containing imidazolin-2-ylidene groups formed the monometallic complex [(1,2,5,6-\u03b7)-cycloocta-1,5-diene](5,16-dibenzyl-1,5,9,12,16,20-hexaazatricyclo[18.2.1.1<jats:sup>9,12<\/jats:sup>]tetracosa-10,21-dien-21,22-diylidene)iridium(I) bromide dichloromethane monosolvate, [Ir(C<jats:sub>8<\/jats:sub>H<jats:sub>12<\/jats:sub>)(C<jats:sub>32<\/jats:sub>H<jats:sub>42<\/jats:sub>N<jats:sub>6<\/jats:sub>)]Br\u00b7CH<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub>, <jats:bold>2a<\/jats:bold>. The structure of iridium complex <jats:bold>2a<\/jats:bold> at 100\u2005K has triclinic <jats:italic>P<\/jats:italic>\\overline{1} symmetry. The ligand in <jats:bold>2a<\/jats:bold> coordinates to the Ir center through the NHC moieties in a <jats:italic>cis<\/jats:italic> fashion. Additionally, the ligand adopts an umbrella-like structure that appears to envelope the Ir center. The structure displays C\u2014H...Br interactions. Macrocycles containing benzimidazolin-2-ylidene groups formed the bimetallic complex [\u03bc-5,20-dibenzyl-1,5,9,16,20,24-hexaazapentacyclo[22.6.1.1<jats:sup>9,16<\/jats:sup>.0<jats:sup>10,15<\/jats:sup>.0<jats:sup>25,30<\/jats:sup>]dotriaconta-10(15),11,13,25(30),26,28-hexaene-31,32-diylidene]bis{bromido[(1,2,5,6-\u03b7)-cycloocta-1,5-diene]iridium(I)}, [Ir<jats:sub>2<\/jats:sub>Br<jats:sub>2<\/jats:sub>(C<jats:sub>8<\/jats:sub>H<jats:sub>12<\/jats:sub>)<jats:sub>2<\/jats:sub>(C<jats:sub>40<\/jats:sub>H<jats:sub>46<\/jats:sub>N<jats:sub>6<\/jats:sub>)], <jats:bold>2b<\/jats:bold>. The structure of complex <jats:bold>2b<\/jats:bold> at 100\u2005K has orthorhombic <jats:italic>Pbca<\/jats:italic> symmetry. Each NHC moiety in <jats:bold>2b<\/jats:bold> coordinates in a monodentate fashion to an Ir(COD) fragment. The structure exhibits disorder of the main molecule. This disorder is found in the portion of the macrocycle containing an amine group. This structure also displays C\u2014H...Br interactions. Finally, the structure of the hexafluorophosphate salt of the imidazolin-2-ylidene-containing macrocycle, namely 5,16-dibenzyl-1\u03bb<jats:sup>5<\/jats:sup>,5,9,12\u03bb<jats:sup>5<\/jats:sup>,16,20-hexaazatricyclo[18.2.1.1<jats:sup>9,12<\/jats:sup>]tetracosa-1(23),10,12(24),21-tetraene-1,12-diium bis(hexafluorophosphate), C<jats:sub>32<\/jats:sub>H<jats:sub>44<\/jats:sub>N<jats:sub>6<\/jats:sub>\n                  <jats:sup>2+<\/jats:sup>\u00b72PF<jats:sub>6<\/jats:sub>\n                  <jats:sup>\u2212<\/jats:sup>, <jats:bold>1c<\/jats:bold>, was determined. The structure of macrocycle <jats:bold>1c<\/jats:bold> at 100\u2005K has triclinic <jats:italic>P<\/jats:italic>\\overline{1} symmetry and was found to contain C\u2014H...F interactions.<\/jats:p>","DOI":"10.1107\/s2053229619015006","type":"journal-article","created":{"date-parts":[[2019,11,25]],"date-time":"2019-11-25T13:44:03Z","timestamp":1574689443000},"page":"1652-1657","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis and structural characterization of iridium(I) complexes of 20-membered macrocyclic rings bearing chelating bis(N-heterocyclic carbene) ligands"],"prefix":"10.1107","volume":"75","author":[{"given":"Rajesh","family":"Thapa","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Stefan M.","family":"Kilyanek","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2019,11,25]]},"reference":[{"key":"ky3185_bb1","doi-asserted-by":"crossref","first-page":"361","DOI":"10.1021\/ja00001a054","volume":"113","author":"Arduengo","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"ky3185_bb2","unstructured":"Bruker (2010). APEX2, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA."},{"key":"ky3185_bb3","unstructured":"Bruker (2016). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA."},{"key":"ky3185_bb4","doi-asserted-by":"crossref","first-page":"5491","DOI":"10.1002\/chem.200900027","volume":"15","author":"Danopoulos","year":"2009","journal-title":"Chem. Eur. J."},{"key":"ky3185_bb5","doi-asserted-by":"crossref","first-page":"509","DOI":"10.1002\/aoc.1650","volume":"24","author":"Diez","year":"2010","journal-title":"Appl. Organomet. Chem."},{"key":"ky3185_bb6","doi-asserted-by":"crossref","first-page":"13642","DOI":"10.1021\/ja038177r","volume":"125","author":"Eckhardt","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ky3185_bb7","doi-asserted-by":"crossref","first-page":"1290","DOI":"10.1002\/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y","volume":"41","author":"Herrmann","year":"2002","journal-title":"Angew. Chem. Int. Ed."},{"key":"ky3185_bb8","doi-asserted-by":"crossref","first-page":"485","DOI":"10.1038\/nature13384","volume":"510","author":"Hopkinson","year":"2014","journal-title":"Nature"},{"key":"ky3185_bb9","doi-asserted-by":"crossref","first-page":"4181","DOI":"10.1016\/j.ica.2010.06.028","volume":"363","author":"Joki\u0107","year":"2010","journal-title":"Inorg. Chim. Acta"},{"key":"ky3185_bb10","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S1600576714022985","volume":"48","author":"Krause","year":"2015","journal-title":"J. Appl. Cryst."},{"key":"ky3185_bb11","doi-asserted-by":"crossref","first-page":"5269","DOI":"10.1021\/om400858y","volume":"32","author":"Liske","year":"2013","journal-title":"Organometallics"},{"key":"ky3185_bb12","doi-asserted-by":"crossref","first-page":"466","DOI":"10.1107\/S0021889807067908","volume":"41","author":"Macrae","year":"2008","journal-title":"J. Appl. Cryst."},{"key":"ky3185_bb13","doi-asserted-by":"crossref","first-page":"841","DOI":"10.1016\/j.ccr.2006.06.008","volume":"251","author":"Mata","year":"2007","journal-title":"Coord. Chem. Rev."},{"key":"ky3185_bb14","doi-asserted-by":"crossref","first-page":"629","DOI":"10.1021\/om034393x","volume":"23","author":"Miecznikowski","year":"2004","journal-title":"Organometallics"},{"key":"ky3185_bb15","doi-asserted-by":"crossref","first-page":"3677","DOI":"10.1021\/cr800501s","volume":"109","author":"Poyatos","year":"2009","journal-title":"Chem. Rev."},{"key":"ky3185_bb16","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Cryst. A"},{"key":"ky3185_bb17","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"ky3185_bb18","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"ky3185_bb19","doi-asserted-by":"crossref","first-page":"148","DOI":"10.1107\/S090744490804362X","volume":"65","author":"Spek","year":"2009","journal-title":"Acta Cryst. D"},{"key":"ky3185_bb20","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1107\/S2053229614024929","volume":"71","author":"Spek","year":"2015","journal-title":"Acta Cryst. C"},{"key":"ky3185_bb21","doi-asserted-by":"crossref","first-page":"12577","DOI":"10.1039\/C9DT02147G","volume":"48","author":"Thapa","year":"2019","journal-title":"Dalton Trans."},{"key":"ky3185_bb22","doi-asserted-by":"crossref","first-page":"42924","DOI":"10.1039\/C4RA06474G","volume":"4","author":"Wang","year":"2014","journal-title":"RSC Adv."}],"container-title":["Acta Crystallographica Section C Structural Chemistry"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/c\/issues\/2019\/12\/00\/ky3185\/ky3185.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/c\/issues\/2019\/12\/00\/ky3185\/ky3185.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T10:55:35Z","timestamp":1736765735000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2053229619015006"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,11,25]]},"references-count":22,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2019,12]]}},"alternative-id":["S2053229619015006"],"URL":"https:\/\/doi.org\/10.1107\/s2053229619015006","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2053229619015006\/ky3185sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2053229619015006\/ky31851csup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2053229619015006\/ky31852asup3.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2053229619015006\/ky31852bsup4.hkl","asserted-by":"subject"}]},"ISSN":["2053-2296"],"issn-type":[{"type":"electronic","value":"2053-2296"}],"subject":[],"published":{"date-parts":[[2019,11,25]]},"assertion":[{"value":"Acta Crystallographica Section C: Structural Chemistry","order":0,"name":"journal","label":"Publication","explanation":{"URL":"http:\/\/journals.iucr.org\/c"},"group":{"name":"general","label":"General"}},{"value":"research papers","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":"http:\/\/scripts.iucr.org\/cgi-bin\/citedin?ky3185","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":"28 July 2019","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"6 November 2019","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"25 November 2019","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?ky3185"}},{"value":"\u00a9 2019 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"}}]}}