{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T05:16:24Z","timestamp":1736831784170,"version":"3.33.0"},"reference-count":8,"publisher":"International Union of Crystallography (IUCr)","issue":"5","license":[{"start":{"date-parts":[[2015,4,9]],"date-time":"2015-04-09T00:00:00Z","timestamp":1428537600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},{"start":{"date-parts":[[2015,4,9]],"date-time":"2015-04-09T00:00:00Z","timestamp":1428537600000},"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>The crystallization of a 1:1 molar solution of 1,2-diiodo-3,4,5,6-tetrafluorobenzene (<jats:italic>o<\/jats:italic>-DITFB) and tetrabutylammonium bromide (<jats:italic>n<\/jats:italic>-Bu<jats:sub>4<\/jats:sub>NBr) from dichloromethane yielded pure white crystals of a halogen-bonded compound, C<jats:sub>16<\/jats:sub>H<jats:sub>36<\/jats:sub>N<jats:sup>+<\/jats:sup>\u00b7Br<jats:sup>\u2212<\/jats:sup>\u00b7C<jats:sub>6<\/jats:sub>F<jats:sub>4<\/jats:sub>I<jats:sub>2<\/jats:sub>\u00b70.5CH<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub>or [(<jats:italic>n<\/jats:italic>-Bu<jats:sub>4<\/jats:sub>NBr)(<jats:italic>o<\/jats:italic>-DITFB)]\u00b70.5CH<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub>. The compound may be described as a quaternary system and may be classified as a salt\u2013cocrystal solvate. The asymmetric unit contains one molecule of solvent, two<jats:italic>o<\/jats:italic>-DITFB molecules, two cations (<jats:italic>n<\/jats:italic>-Bu<jats:sub>4<\/jats:sub>N<jats:sup>+<\/jats:sup>) and two crystallographically distinct bromide ions [\u03b8<jats:sub>I<\/jats:sub><jats:bold><jats:sub>...<\/jats:sub><\/jats:bold><jats:sub>Br-<\/jats:sub><jats:bold><jats:sub>...<\/jats:sub><\/jats:bold><jats:sub>I<\/jats:sub>= 144.18\u2005(1) and 135.35\u2005(1)\u00b0]. The bromide ion is a bidentate halogen-bond acceptor which interacts with two covalently bonded iodines (<jats:italic>i.e.<\/jats:italic>halogen-bond donors), resulting in a one-dimensional polymeric zigzag chain network approximately along the<jats:italic>a<\/jats:italic>axis. The observed short contacts and angles are characteristic of the non-covalent interaction [<jats:italic>d<\/jats:italic><jats:sub>C\u2014I...Br<\/jats:sub>= 3.1593\u2005(4)\u20133.2590\u2005(5)\u2005\u00c5; \u03b8<jats:sub>C\u2014I...Br<\/jats:sub>= 174.89\u2005(7) and 178.16\u2005(7)\u00b0]. It is noted that iodine acts as both a halogen-bond donor and a weak CH hydrogen-bond acceptor, while the bromide ions act as acceptors for weak CH hydrogen bonds and halogen bonds.<\/jats:p>","DOI":"10.1107\/s2056989015006593","type":"journal-article","created":{"date-parts":[[2015,4,8]],"date-time":"2015-04-08T09:58:07Z","timestamp":1428487087000},"page":"o286-o287","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":2,"title":["Crystal structure of tetrabutylammonium bromide\u20131,2-diiodo-3,4,5,6-tetrafluorobenzene\u2013dichloromethane (2\/2\/1)"],"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":[[2015,4,9]]},"reference":[{"key":"gw2150_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":"gw2150_bb2","unstructured":"Bond, A. D. (2012). Pharmaceutical Salts and Co-crystals, RSC Drug Discovery Series, No. 16, edited by J. Wouters & L. Qu\u00e9r\u00e9, ch. 2. Cambridge: Royal Society of Chemistry."},{"key":"gw2150_bb3","unstructured":"Bruker (2005). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA."},{"key":"gw2150_bb4","unstructured":"Desiraju, G. R. & Steiner, T. (1999). In The Weak Hydrogen Bond. Oxford University Press."},{"key":"gw2150_bb5","doi-asserted-by":"crossref","first-page":"o2599","DOI":"10.1107\/S1600536811032612","volume":"67","author":"Elsegood","year":"2011","journal-title":"Acta Cryst. E"},{"key":"gw2150_bb6","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Cryst. 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