{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T08:50:23Z","timestamp":1736844623566,"version":"3.33.0"},"reference-count":18,"publisher":"International Union of Crystallography (IUCr)","issue":"10","license":[{"start":{"date-parts":[[2020,9,4]],"date-time":"2020-09-04T00:00:00Z","timestamp":1599177600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2020,9,4]],"date-time":"2020-09-04T00:00:00Z","timestamp":1599177600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"name":"The University of Western Australia"}],"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":[[2020,8,25]]},"published-print":{"date-parts":[[2020,10,1]]},"abstract":"<jats:p>The title compounds, [Ir(C<jats:sub>51<\/jats:sub>H<jats:sub>64<\/jats:sub>N<jats:sub>2<\/jats:sub>)Cl(C<jats:sub>8<\/jats:sub>H<jats:sub>12<\/jats:sub>)]\u00b7CH<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub>, (I), and [Ir(C<jats:sub>51<\/jats:sub>H<jats:sub>64<\/jats:sub>N<jats:sub>2<\/jats:sub>)Cl(C<jats:sub>8<\/jats:sub>H<jats:sub>12<\/jats:sub>)], (II), represent the first two examples of hexahydrobenzoimidazole-based <jats:italic>N<\/jats:italic>-heterocyclic carbene (NHC) iridium complexes. The diastereomeric complexes differing only in their axial chirality, which could be separated <jats:italic>via<\/jats:italic> column chromatography, show noticeable differences in their <jats:sup>1<\/jats:sup>H NMR spectra. Compound (I) crystallizes in the monoclinic system (<jats:italic>P<\/jats:italic>2<jats:sub>1<\/jats:sub>) with two independent complexes and two half-occupied dichloromethane molecules in the asymmetric unit, while compound (II) crystallizes in the orthorhombic system (<jats:italic>P<\/jats:italic>2<jats:sub>1<\/jats:sub>2<jats:sub>1<\/jats:sub>2<jats:sub>1<\/jats:sub>) with one complex in the asymmetric unit. The fused five-membered <jats:italic>N<\/jats:italic>-heterocycles of NHCs show unusually high backbone torsion angles of \u221234.1\u2005(5) and \u221230.9\u2005(5)\u00b0 for (I) and \u221231.5\u2005(7)\u00b0 for (II), but the Ir\u2014C<jats:sub>carbene<\/jats:sub> bond lengths of 2.046\u2005(6) and 2.021\u2005(6)\u2005\u00c5 for (I) and 2.045\u2005(8)\u2005\u00c5 for (II) present typical NHC\u2014Ir bond lengths. The solvent molecule in the crystal of (I) was found to be highly disordered and its contribution to the scattering was masked using the solvent-masking routine smtbx.mask in <jats:italic>OLEX2<\/jats:italic> [Dolomanov <jats:italic>et al.<\/jats:italic> (2009). <jats:italic>J. Appl. Cryst.<\/jats:italic> \n                  <jats:bold>42<\/jats:bold>, 339\u2013341]. The solvent contribution is not included in the reported chemical formula and other crystal data.<\/jats:p>","DOI":"10.1107\/s2056989020011603","type":"journal-article","created":{"date-parts":[[2020,9,4]],"date-time":"2020-09-04T11:14:11Z","timestamp":1599218051000},"page":"1543-1547","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Crystal structures of [\u03bc<sub>2<\/sub>-(<i>R<sub>a<\/sub>\n                  <\/i>,<i>S<sub>a<\/sub>\n                  <\/i>,3a<i>R<\/i>,7a<i>R<\/i>)-1,3-bis(2,7-dicyclohexylnaphthalen-1-yl)octahydro-1<i>H<\/i>-benzo[<i>d<\/i>]imidazolidin-2-ylidene]chlorido(\u03b7<sup>4<\/sup>-1,5-cyclooctadiene)iridium dichloromethane monosolvate and [\u03bc<sub>2<\/sub>-(<i>S<sub>a<\/sub>\n                  <\/i>,<i>S<sub>a<\/sub>\n                  <\/i>,3a<i>R<\/i>,7a<i>R<\/i>)-1,3-bis(2,7-dicyclohexylnaphthalen-1-yl)octahydro-1<i>H<\/i>-benzo[<i>d<\/i>]imidazolidin-2-ylidene]chlorido(\u03b7<sup>4<\/sup>-1,5-cyclooctadiene)iridium"],"prefix":"10.1107","volume":"76","author":[{"given":"Stephen A.","family":"Moggach","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Brian W.","family":"Skelton","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Daven J.","family":"Foster","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2020,9,4]]},"reference":[{"key":"is5546_bb1","doi-asserted-by":"crossref","first-page":"1576","DOI":"10.1248\/cpb.54.1576","volume":"54","author":"Arao","year":"2006","journal-title":"Chem. 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