{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T05:17:03Z","timestamp":1736831823857,"version":"3.33.0"},"reference-count":8,"publisher":"International Union of Crystallography (IUCr)","issue":"5","license":[{"start":{"date-parts":[[2015,4,18]],"date-time":"2015-04-18T00:00:00Z","timestamp":1429315200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},{"start":{"date-parts":[[2015,4,18]],"date-time":"2015-04-18T00:00:00Z","timestamp":1429315200000},"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 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"],"published-print":{"date-parts":[[2015,5,1]]},"abstract":"<jats:p>Equimolar quantities of tetraethylammonium chloride (Et<jats:sub>4<\/jats:sub>NCl) and 3,4,5,6-tetrafluoro-1,2-diiodobenzene (<jats:italic>o<\/jats:italic>-DITFB or<jats:italic>o<\/jats:italic>-C<jats:sub>6<\/jats:sub>F<jats:sub>4<\/jats:sub>I<jats:sub>2<\/jats:sub>) have been co-crystallized in a solution of dichloromethane yielding a pure halogen-bonded compound, 3,4,5,6-tetrafluoro-1,2-diiodobenzene\u2013tetraethyl ammonium chloride (2\/1), Et<jats:sub>4<\/jats:sub>N<jats:sup>+<\/jats:sup>\u00b7Cl<jats:sup>\u2212<\/jats:sup>\u00b72C<jats:sub>6<\/jats:sub>F<jats:sub>4<\/jats:sub>I<jats:sub>2<\/jats:sub>, in the form of translucent needles. [(Et<jats:sub>4<\/jats:sub>NCl)(<jats:italic>o<\/jats:italic>-C<jats:sub>6<\/jats:sub>F<jats:sub>4<\/jats:sub>I<jats:sub>2<\/jats:sub>)<jats:sub>2<\/jats:sub>] packs in the<jats:italic>C<\/jats:italic>2\/<jats:italic>c<\/jats:italic>space group. The asymmetric unit includes one molecule of DITFB, one Et<jats:sub>4<\/jats:sub>N<jats:sup>+<\/jats:sup>cation located on a twofold rotation axis, and one chloride anion also located on a twofold rotation symmetry axis. This compound has an interesting halogen-bonding environment surrounding the halide. Here, the chloride anion acts as a tetradentate halogen bond acceptor and forms a distorted square-pyramidal geometry, with I...Cl<jats:sup>\u2212<\/jats:sup>...I angles of 80.891\u2005(6) and 78.811\u2005(11)\u00b0, where two crystallographically distinct iodine atoms form halogen bonds with the chloride anion. Resulting from that square-pyramidal geometry are short contacts between some of the adjacent F atoms. Along the<jats:italic>b<\/jats:italic>axis, the halogen-bonding interaction results in a polymeric network, producing a sheet in which the two closest chloride ions are 7.8931\u2005(6)\u2005\u00c5 apart. The Et<jats:sub>4<\/jats:sub>N<jats:sup>+<\/jats:sup>cation alternates in columns with the halide ion. The expected short contacts (shorter than the sum of their van der Waals radii) are observed for the halogen bonds [3.2191\u2005(2) and 3.2968\u2005(2)\u2005\u00c5], as well as almost linear angles [170.953\u2005(6) and 173.529\u2005(6)\u00b0].<\/jats:p>","DOI":"10.1107\/s205698901500732x","type":"journal-article","created":{"date-parts":[[2015,4,17]],"date-time":"2015-04-17T08:17:51Z","timestamp":1429258671000},"page":"o319-o320","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Crystal structure of tetraethylammonium chloride 3,4,5,6-tetrafluoro-1,2-diiodobenzene"],"prefix":"10.1107","volume":"71","author":[{"given":"Jasmine","family":"Viger-Gravel","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ilia","family":"Korobkov","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"David L.","family":"Bryce","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2015,4,18]]},"reference":[{"key":"gw2151_bb1","doi-asserted-by":"crossref","first-page":"1171","DOI":"10.1016\/j.jfluchem.2009.07.005","volume":"130","author":"Abate","year":"2009","journal-title":"J. Fluor. Chem."},{"key":"gw2151_bb2","unstructured":"Bruker (2009). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA."},{"key":"gw2151_bb3","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Cryst. A"},{"key":"gw2151_bb4","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"gw2151_bb5","doi-asserted-by":"crossref","first-page":"231","DOI":"10.1515\/ncrs-1999-0241","volume":"214","author":"Staples","year":"1999","journal-title":"Z. Kristallogr. New Cryst. Struct."},{"key":"gw2151_bb10","doi-asserted-by":"crossref","first-page":"o286","DOI":"10.1107\/S2056989015006593","volume":"71","author":"Viger-Gravel","year":"2015","journal-title":"Acta Cryst. E"},{"key":"gw2151_bb6","doi-asserted-by":"crossref","first-page":"6929","DOI":"10.1021\/ja5013239","volume":"136","author":"Viger-Gravel","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"gw2151_bb7","doi-asserted-by":"crossref","first-page":"7285","DOI":"10.1039\/C4CE00345D","volume":"16","author":"Viger-Gravel","year":"2014","journal-title":"CrystEngComm"}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2015\/05\/00\/gw2151\/gw2151.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2015\/05\/00\/gw2151\/gw2151.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T10:36:12Z","timestamp":1736764572000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S205698901500732X"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,4,18]]},"references-count":8,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2015,5]]}},"alternative-id":["S205698901500732X"],"URL":"https:\/\/doi.org\/10.1107\/s205698901500732x","relation":{},"ISSN":["2056-9890"],"issn-type":[{"type":"electronic","value":"2056-9890"}],"subject":[],"published":{"date-parts":[[2015,4,18]]},"assertion":[{"value":"Acta Crystallographica Section E: Crystallographic Communications","name":"journal","label":"Journal","explanation":{"URL":"http:\/\/journals.iucr.org\/e"}},{"value":"data reports","name":"content_type","label":"Content type","explanation":{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2011\/01\/00\/me0439\/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":"12 March 2015","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"13 April 2015","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"18 April 2015","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?gw2151"}},{"value":"\u00a9 2015 Viger-Gravelet 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":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}}]}}