{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,20]],"date-time":"2026-03-20T02:25:02Z","timestamp":1773973502386,"version":"3.50.1"},"reference-count":27,"publisher":"International Union of Crystallography (IUCr)","issue":"11","license":[{"start":{"date-parts":[[2019,10,22]],"date-time":"2019-10-22T00:00:00Z","timestamp":1571702400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2019,10,22]],"date-time":"2019-10-22T00:00:00Z","timestamp":1571702400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"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":[[2019,10,8]]},"published-print":{"date-parts":[[2019,11,1]]},"abstract":"<jats:p>The reactions of N-heterocyclic carbene Cu<jats:sup>I<\/jats:sup> and Ag<jats:sup>I<\/jats:sup> halides with potassium thio- or selenocyanate gave unexpected products. The attempted substitution reaction of bromido(1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene)silver (NHC*\u2014Ag\u2014Br) with KSCN yielded bis[bis(1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene)silver(I)] tris(thiocyanato)argentate(I) diethyl ether disolvate, [Ag(C<jats:sub>29<\/jats:sub>H<jats:sub>24<\/jats:sub>N<jats:sub>2<\/jats:sub>)<jats:sub>2<\/jats:sub>][Ag(NCS)<jats:sub>3<\/jats:sub>]\u00b72C<jats:sub>4<\/jats:sub>H<jats:sub>10<\/jats:sub>O or [NHC*<jats:sub>2<\/jats:sub>Ag]<jats:sub>2<\/jats:sub>[Ag(SCN)<jats:sub>3<\/jats:sub>]\u00b72Et<jats:sub>2<\/jats:sub>O, (<jats:bold>1<\/jats:bold>), while reaction with KSeCN led to bis(\u03bc-1,3-dibenzyl-4,5-diphenyl-2-selenoimidazole-\u03ba<jats:sup>2<\/jats:sup>\n                  <jats:italic>Se<\/jats:italic>:<jats:italic>Se<\/jats:italic>)bis[bromido(1,3-dibenzyl-4,5-diphenyl-2-selenoimidazole-\u03ba<jats:italic>Se<\/jats:italic>)silver(I)] dichloromethane hexasolvate, [Ag<jats:sub>2<\/jats:sub>Br<jats:sub>2<\/jats:sub>(C<jats:sub>29<\/jats:sub>H<jats:sub>24<\/jats:sub>N<jats:sub>2<\/jats:sub>Se)<jats:sub>4<\/jats:sub>]\u00b76CH<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub> or (NHC*Se)<jats:sub>4<\/jats:sub>Ag<jats:sub>2<\/jats:sub>Br<jats:sub>2<\/jats:sub>\u00b76CH<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub>, (<jats:bold>2<\/jats:bold>), <jats:italic>via<\/jats:italic> oxidation of the NHC* fragment to 2-selenoimidazole. This oxidation was observed again in the reaction of NHC*\u2014Cu\u2014Br with KSeCN, yielding <jats:italic>catena<\/jats:italic>-poly[[[(1,3-dibenzyl-4,5-diphenyl-2-selenoimidazole-\u03ba<jats:italic>Se<\/jats:italic>)copper(I)]-\u03bc-cyanido-\u03ba<jats:sup>2<\/jats:sup>\n                  <jats:italic>C<\/jats:italic>:<jats:italic>N<\/jats:italic>] acetonitrile monosolvate], {[Cu(CN)(C<jats:sub>29<\/jats:sub>H<jats:sub>24<\/jats:sub>N<jats:sub>2<\/jats:sub>Se)]\u00b7C<jats:sub>2<\/jats:sub>H<jats:sub>3<\/jats:sub>N}<jats:sub>\n                     <jats:italic>n<\/jats:italic>\n                  <\/jats:sub> or NHC*Se\u2014CuCN\u00b7CH<jats:sub>3<\/jats:sub>CN, (<jats:bold>3<\/jats:bold>). Compound (<jats:bold>1<\/jats:bold>) represents an organic\/inorganic salt with Ag<jats:sup>I<\/jats:sup> in a linear coordination in each of the two cations and in a trigonal coordination in the anion, accompanied by diethyl ether solvent molecules. The tri-blade boomerang-shaped complex anion [Ag(SCN)<jats:sub>3<\/jats:sub>]<jats:sup>2\u2212<\/jats:sup> present in (<jats:bold>1<\/jats:bold>) is characterized by X-ray diffraction for the first time. Compound (<jats:bold>2<\/jats:bold>) comprises an isolated centrosymmetric molecule with Ag<jats:sup>I<\/jats:sup> in a distorted tetrahedral BrSe<jats:sub>3<\/jats:sub> coordination, together with dichloromethane solvent molecules. Compound (<jats:bold>3<\/jats:bold>) exhibits a linear polymeric <jats:sup>1<\/jats:sup>\n                  <jats:sub>\u221e<\/jats:sub>[Cu\u2014C[triple-bond]N\u2014Cu\u2014] chain structure with a selenoimidazole moiety additionally coordinating to each Cu<jats:sup>I<\/jats:sup> atom, and completed by acetonitrile solvent molecules. Electron densities associated with an additional ether solvent molecule in (<jats:bold>1<\/jats:bold>) and two additional dichloromethane solvent molecules in (<jats:bold>2<\/jats:bold>) were removed with the SQUEEZE procedure [Spek (2015). <jats:italic>Acta Cryst.<\/jats:italic> C<jats:bold>71<\/jats:bold>, 9\u201318] in <jats:italic>PLATON<\/jats:italic>.<\/jats:p>","DOI":"10.1107\/s2056989019013719","type":"journal-article","created":{"date-parts":[[2019,10,22]],"date-time":"2019-10-22T14:48:47Z","timestamp":1571755727000},"page":"1657-1663","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":2,"title":["Unexpected reactions of NHC*\u2014Cu<sup>I<\/sup> and \u2014Ag<sup>I<\/sup> bromides with potassium thio- or selenocyanate"],"prefix":"10.1107","volume":"75","author":[{"given":"Matthias","family":"Tacke","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Daniel","family":"Marh\u00f6fer","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hessah","family":"Althani","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Helge","family":"M\u00fcller-Bunz","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2019,10,22]]},"reference":[{"key":"wm5519_bb1","doi-asserted-by":"crossref","first-page":"3452","DOI":"10.1002\/ejic.201700494","volume":"2017","author":"Bockfeld","year":"2017","journal-title":"Eur. J. Inorg. Chem."},{"key":"wm5519_bb2","unstructured":"Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany."},{"key":"wm5519_bb3","doi-asserted-by":"crossref","first-page":"745","DOI":"10.1007\/s10534-014-9766-z","volume":"27","author":"Browne","year":"2014","journal-title":"Biometals"},{"key":"wm5519_bb4","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1016\/j.jorganchem.2017.03.050","volume":"840","author":"Dada","year":"2017","journal-title":"J. Organomet. Chem."},{"key":"wm5519_bb5","first-page":"575","volume":"49","author":"Drake","year":"2005","journal-title":"Ann. Occup. Hyg."},{"key":"wm5519_bb6","doi-asserted-by":"crossref","first-page":"184","DOI":"10.1001\/archsurg.1968.01330200022004","volume":"96","author":"Fox","year":"1968","journal-title":"Arch. Surg."},{"key":"wm5519_bb7","doi-asserted-by":"crossref","first-page":"8144","DOI":"10.1039\/C4DT00624K","volume":"43","author":"Hackenberg","year":"2014","journal-title":"Dalton Trans."},{"key":"wm5519_bb8","doi-asserted-by":"crossref","first-page":"806","DOI":"10.1039\/J19700000806","volume":"A","author":"Hathaway","year":"1970","journal-title":"J. Chem. Soc."},{"key":"wm5519_bb9","doi-asserted-by":"crossref","first-page":"246","DOI":"10.1002\/ajim.20670","volume":"52","author":"Kim","year":"2009","journal-title":"Am. J. Ind. Med."},{"key":"wm5519_bb10","doi-asserted-by":"crossref","first-page":"3711","DOI":"10.1039\/c1dt10104h","volume":"40","author":"Kimani","year":"2011","journal-title":"Dalton Trans."},{"key":"wm5519_bb11","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1016\/S0305-4179(99)00108-4","volume":"26","author":"Klasen","year":"2000","journal-title":"Burns"},{"key":"wm5519_bb12","doi-asserted-by":"crossref","first-page":"62","DOI":"10.1016\/j.ejmech.2018.07.057","volume":"157","author":"Liang","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"wm5519_bb13","doi-asserted-by":"crossref","first-page":"10671","DOI":"10.1039\/C8DT01506F","volume":"47","author":"Nahra","year":"2018","journal-title":"Dalton Trans."},{"key":"wm5519_bb14","doi-asserted-by":"crossref","first-page":"74","DOI":"10.1039\/C0MT00034E","volume":"3","author":"Patil","year":"2011","journal-title":"Metallomics"},{"key":"wm5519_bb15","doi-asserted-by":"crossref","first-page":"1471","DOI":"10.1039\/C7DT04243D","volume":"47","author":"Perras","year":"2018","journal-title":"Dalton Trans."},{"key":"wm5519_bb16","unstructured":"Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, Oxfordshire, England."},{"key":"wm5519_bb17","doi-asserted-by":"crossref","first-page":"25","DOI":"10.3390\/antibiotics1010025","volume":"1","author":"Sharkey","year":"2012","journal-title":"Antibiotics"},{"key":"wm5519_bb18","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"wm5519_bb19","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"wm5519_bb20","doi-asserted-by":"crossref","first-page":"341","DOI":"10.1016\/S0168-6445(03)00047-0","volume":"27","author":"Silver","year":"2003","journal-title":"FEMS Microbiol. Rev."},{"key":"wm5519_bb21","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1107\/S2053229614024929","volume":"71","author":"Spek","year":"2015","journal-title":"Acta Cryst. C"},{"key":"wm5519_bb22","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1099\/00222615-29-2-101","volume":"29","author":"Starodub","year":"1989","journal-title":"J. Med. Microbiol."},{"key":"wm5519_bb23","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/j.jorganchem.2013.09.033","volume":"749","author":"Streciwilk","year":"2014","journal-title":"J. Organomet. Chem."},{"key":"wm5519_bb24","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1002\/zaac.19845150823","volume":"515","author":"Thiele","year":"1984","journal-title":"Z. Anorg. Allg. Chem."},{"key":"wm5519_bb25","doi-asserted-by":"crossref","first-page":"2416","DOI":"10.1002\/ejic.201500174","volume":"2015","author":"Verlinden","year":"2015","journal-title":"Eur. J. Inorg. Chem."},{"key":"wm5519_bb26","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1107\/S0021889810022120","volume":"43","author":"Westrip","year":"2010","journal-title":"J. Appl. Cryst."},{"key":"wm5519_bb27","first-page":"3","volume":"15","author":"White","year":"2002","journal-title":"Br. J. Nurs."}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2019\/11\/00\/wm5519\/wm5519.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2019\/11\/00\/wm5519\/wm5519.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T10:52:42Z","timestamp":1736765562000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989019013719"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,10,22]]},"references-count":27,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2019,11]]}},"alternative-id":["S2056989019013719"],"URL":"https:\/\/doi.org\/10.1107\/s2056989019013719","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989019013719\/wm5519sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989019013719\/wm55191sup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989019013719\/wm55192sup3.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989019013719\/wm55193sup4.hkl","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"value":"2056-9890","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,10,22]]},"assertion":[{"value":"Acta Crystallographica Section E: Crystallographic Communications","order":0,"name":"journal","label":"Publication","explanation":{"URL":"http:\/\/journals.iucr.org\/e"},"group":{"name":"general","label":"General"}},{"value":"research communications","order":1,"name":"content_type","label":"Content type","explanation":{"URL":"https:\/\/journals.iucr.org\/e\/services\/notesforauthors.html"},"group":{"name":"general","label":"General"}},{"value":"Available","URL":"http:\/\/scripts.iucr.org\/cgi-bin\/citedin?wm5519","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":"22 August 2019","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"8 October 2019","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"22 October 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?wm5519"}},{"value":"\u00a9 2019 Tacke et 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":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}}]}}