{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,25]],"date-time":"2025-11-25T20:40:36Z","timestamp":1764103236500,"version":"3.37.3"},"reference-count":9,"publisher":"International Union of Crystallography (IUCr)","issue":"10","license":[{"start":{"date-parts":[[2021,10,13]],"date-time":"2021-10-13T00:00:00Z","timestamp":1634083200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2021,10,13]],"date-time":"2021-10-13T00:00:00Z","timestamp":1634083200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/501100000038","name":"Natural Sciences and Engineering Research Council of Canada","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100000038","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["IUCrData","IUCr Data","International Union Crystallogr Data","Int Union Cryst Data"],"accepted":{"date-parts":[[2021,10,7]]},"published-print":{"date-parts":[[2021,10,28]]},"abstract":"<jats:p>The single-crystal structure of the title compound, C<jats:sub>4<\/jats:sub>H<jats:sub>10<\/jats:sub>N<jats:sub>2<\/jats:sub>\u00b72C<jats:sub>6<\/jats:sub>F<jats:sub>3<\/jats:sub>I<jats:sub>3<\/jats:sub>, features a moderately strong halogen bond between one of the three crystallographically distinct iodine atoms and the nitrogen atom. The iodine\u2013nitrogen distance is 2.820\u2005(3)\u2005\u00c5, corresponding to 80% of the sum of their van der Waals radii. The C\u2014I...N halogen bond angle is 178.0\u2005(1)\u00b0, consistent with the linear interaction of nitrogen <jats:italic>via<\/jats:italic> a \u03c3-hole opposite the carbon\u2013iodine covalent bond. The other two iodine atoms do not engage in halogen bonding. Some weak C\u2014H...F and \u2014H...I interactions are also observed. The complete piperazine molecule is generated by symmetry.<\/jats:p>","DOI":"10.1107\/s2414314621010440","type":"journal-article","created":{"date-parts":[[2021,10,13]],"date-time":"2021-10-13T18:48:56Z","timestamp":1634150936000},"update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["1,3,5-Trifluoro-2,4,6-triiodobenzene\u2013piperazine (2\/1)"],"prefix":"10.1107","volume":"6","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9467-3959","authenticated-orcid":true,"given":"Christelle","family":"Hajjar","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jeffrey S.","family":"Ovens","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":[[2021,10,13]]},"reference":[{"key":"bv4042_bb2","unstructured":"Bruker (2010). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA."},{"key":"bv4042_bb3","doi-asserted-by":"crossref","first-page":"2478","DOI":"10.1021\/acs.chemrev.5b00484","volume":"116","author":"Cavallo","year":"2016","journal-title":"Chem. Rev."},{"key":"bv4042_bb4","doi-asserted-by":"crossref","first-page":"1281","DOI":"10.1107\/S0021889811043202","volume":"44","author":"H\u00fcbschle","year":"2011","journal-title":"J. Appl. Cryst."},{"key":"bv4042_bb5","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S1600576714022985","volume":"48","author":"Krause","year":"2015","journal-title":"J. Appl. Cryst."},{"key":"bv4042_bb1","doi-asserted-by":"crossref","first-page":"226","DOI":"10.1107\/S1600576719014092","volume":"53","author":"Macrae","year":"2020","journal-title":"J. Appl. Cryst."},{"key":"bv4042_bb6","doi-asserted-by":"crossref","first-page":"2160","DOI":"10.1039\/b901473j","author":"Raatikainen","year":"2009","journal-title":"Chem. Commun."},{"key":"bv4042_bb7","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"bv4042_bb8","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"bv4042_bb9","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1107\/S2053229616015023","volume":"73","author":"Szell","year":"2017","journal-title":"Acta Cryst. C"}],"container-title":["IUCrData"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/x\/issues\/2021\/10\/00\/bv4042\/bv4042.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/x\/issues\/2021\/10\/00\/bv4042\/bv4042.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T10:41:10Z","timestamp":1736764870000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2414314621010440"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,10,13]]},"references-count":9,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2021,10]]}},"alternative-id":["S2414314621010440"],"URL":"https:\/\/doi.org\/10.1107\/s2414314621010440","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2414314621010440\/bv4042sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2414314621010440\/bv4042Isup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2414314621010440\/bv4042Isup3.cml","asserted-by":"subject"}]},"ISSN":["2414-3146"],"issn-type":[{"type":"electronic","value":"2414-3146"}],"subject":[],"published":{"date-parts":[[2021,10,13]]},"assertion":[{"value":"IUCrData","order":0,"name":"journal","label":"Publication","explanation":{"URL":"http:\/\/journals.iucr.org\/x"},"group":{"name":"general","label":"General"}},{"value":"data reports","order":1,"name":"content_type","label":"Content type","explanation":{"URL":"https:\/\/journals.iucr.org\/x\/services\/notesforauthors.html"},"group":{"name":"general","label":"General"}},{"value":"Available","URL":"https:\/\/scripts.iucr.org\/cgi-bin\/citedin?bv4042","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":"1 September 2021","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"7 October 2021","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"13 October 2021","order":2,"name":"published_online","label":"Published online","group":{"name":"publication_history","label":"Publication history"}},{"value":"This data article has supporting information","name":"supplementary_materials","label":"Supplementary materials","explanation":{"URL":"https:\/\/scripts.iucr.org\/cgi-bin\/sendsup?bv4042"}},{"value":"\u00a9 2021 Hajjar 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"}}],"article-number":"x211044"}}