{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T21:49:25Z","timestamp":1740174565058,"version":"3.37.3"},"reference-count":55,"publisher":"International Union of Crystallography (IUCr)","issue":"11","license":[{"start":{"date-parts":[[2021,10,5]],"date-time":"2021-10-05T00:00:00Z","timestamp":1633392000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2021,10,5]],"date-time":"2021-10-05T00:00:00Z","timestamp":1633392000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/501100007684","name":"Ministry of Education and Science of Ukraine","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100007684","id-type":"DOI","asserted-by":"publisher"}]}],"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":[[2021,9,28]]},"published-print":{"date-parts":[[2021,11,1]]},"abstract":"<jats:p>The title compound, C<jats:sub>17<\/jats:sub>H<jats:sub>7<\/jats:sub>F<jats:sub>8<\/jats:sub>N<jats:sub>3<\/jats:sub>O, was obtained <jats:italic>via<\/jats:italic> the reaction of 1-azido-2,3,4,5,6-pentafluorobenzene with 4,4,4-trifluoro-1-(<jats:italic>p<\/jats:italic>-tolyl)butane-1,3-dione using triethylamine as a base catalyst and solvent. The dihedral angles between the pentafluorophenyl (<jats:italic>A<\/jats:italic>), triazole (<jats:italic>B<\/jats:italic>) and <jats:italic>p<\/jats:italic>-tolyl (<jats:italic>C<\/jats:italic>) rings are <jats:italic>A<\/jats:italic>\/<jats:italic>B<\/jats:italic> = 62.3\u2005(2), <jats:italic>B<\/jats:italic>\/<jats:italic>C<\/jats:italic> = 43.9\u2005(3) and <jats:italic>A<\/jats:italic>\/<jats:italic>C<\/jats:italic> = 19.1\u2005(3)\u00b0. In the crystal, the molecules are linked by C\u2014H...F and C\u2014H...O hydrogen bonds as well as by aromatic \u03c0\u2013\u03c0 stacking interactions into a three-dimensional network. To further analyse the intermolecular interactions, a Hirshfeld surface analysis was performed.<\/jats:p>","DOI":"10.1107\/s2056989021010070","type":"journal-article","created":{"date-parts":[[2021,10,5]],"date-time":"2021-10-05T07:49:19Z","timestamp":1633420159000},"page":"1067-1071","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["Synthesis, crystal structure and Hirshfeld surface analysis of (4-methylphenyl)[1-(pentafluorophenyl)-5-(trifluoromethyl)-1<i>H<\/i>-1,2,3-triazol-4-yl]methanone"],"prefix":"10.1107","volume":"77","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8222-5008","authenticated-orcid":true,"given":"Nazariy T.","family":"Pokhodylo","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yurii","family":"Slyvka","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Evgeny","family":"Goreshnik","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Roman","family":"Lytvyn","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2021,10,5]]},"reference":[{"key":"hb7985_bb1","doi-asserted-by":"crossref","first-page":"o638","DOI":"10.1107\/S1600536813008246","volume":"69","author":"Abdel-Wahab","year":"2013","journal-title":"Acta Cryst. E"},{"key":"hb7985_bb2","doi-asserted-by":"crossref","first-page":"3676","DOI":"10.1021\/ol501458p","volume":"16","author":"Berry","year":"2014","journal-title":"Org. Lett."},{"key":"hb7985_bb3","doi-asserted-by":"crossref","first-page":"3156","DOI":"10.1002\/asia.201701277","volume":"12","author":"Birkenfelder","year":"2017","journal-title":"Chem. Asian J."},{"key":"hb7985_bb4","doi-asserted-by":"crossref","first-page":"7045","DOI":"10.1002\/slct.201801344","volume":"3","author":"Blastik","year":"2018","journal-title":"ChemistrySelect"},{"key":"hb7985_bb5","doi-asserted-by":"crossref","first-page":"o818","DOI":"10.1107\/S1600536814014603","volume":"70","author":"Bunev","year":"2014","journal-title":"Acta Cryst. E"},{"key":"hb7985_bb6","doi-asserted-by":"crossref","first-page":"3584","DOI":"10.1002\/chem.201002775","volume":"17","author":"Danence","year":"2011","journal-title":"Chem. Eur. J."},{"key":"hb7985_bb7","doi-asserted-by":"crossref","first-page":"109493","DOI":"10.1016\/j.dyepig.2021.109493","volume":"193","author":"Danyliv","year":"2021","journal-title":"Dyes Pigments"},{"key":"hb7985_bb8","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Cryst."},{"key":"hb7985_bb11","doi-asserted-by":"crossref","unstructured":"El-Hiti, G. A., Abdel-Wahab, B. F., Alotaibi, M. H., Hegazy, A. S. & Kariuki, B. M. (2017). IUCrData, 2, x171782.","DOI":"10.1107\/S241431461701820X"},{"key":"hb7985_bb12","unstructured":"El-Hiti, G. A., Abdel-Wahab, B. F., Alotaibi, M. H., Hegazy, A. S. & Kariuki, B. M. (2018). IUCrData, 3, x171841."},{"key":"hb7985_bb13","doi-asserted-by":"crossref","first-page":"1297","DOI":"10.1002\/cjoc.202100188","volume":"39","author":"Feng","year":"2021","journal-title":"Chin. J. Chem."},{"key":"hb7985_bb14","doi-asserted-by":"crossref","first-page":"1812","DOI":"10.1021\/ic3018419","volume":"52","author":"Fern\u00e1ndez-Hern\u00e1ndez","year":"2013","journal-title":"Inorg. Chem."},{"key":"hb7985_bb15","doi-asserted-by":"crossref","first-page":"1344","DOI":"10.1002\/ejoc.202001638","author":"Funabiki","year":"2021","journal-title":"Eur. J. Org. Chem."},{"key":"hb7985_bb16","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1016\/j.dyepig.2016.08.015","volume":"136","author":"Gavlik","year":"2017","journal-title":"Dyes Pigments"},{"key":"hb7985_bb17","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Cryst. B"},{"key":"hb7985_bb18","doi-asserted-by":"crossref","first-page":"1137","DOI":"10.1021\/ja310680x","volume":"135","author":"He","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"hb7985_bb19","doi-asserted-by":"crossref","first-page":"5322","DOI":"10.1021\/ol402582p","volume":"15","author":"He","year":"2013","journal-title":"Org. Lett."},{"key":"hb7985_bb20","doi-asserted-by":"crossref","first-page":"13179","DOI":"10.1039\/C8TC04867C","volume":"6","author":"Hladka","year":"2018","journal-title":"J. Mater. Chem. C."},{"key":"hb7985_bb21","doi-asserted-by":"crossref","first-page":"11791","DOI":"10.1039\/c1jm10901d","volume":"21","author":"Ichikawa","year":"2011","journal-title":"J. Mater. Chem."},{"key":"hb7985_bb22","doi-asserted-by":"crossref","first-page":"9987","DOI":"10.1039\/C8NJ00606G","volume":"42","author":"Kandhadi","year":"2018","journal-title":"New J. Chem."},{"key":"hb7985_bb23","doi-asserted-by":"crossref","first-page":"2816","DOI":"10.1002\/asia.201100404","volume":"6","author":"Kloss","year":"2011","journal-title":"Chem. Asian J."},{"key":"hb7985_bb24","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1070\/RC2005v074n04ABEH000893","volume":"74","author":"Krivopalov","year":"2005","journal-title":"Russ. Chem. Rev."},{"key":"hb7985_bb25","doi-asserted-by":"crossref","first-page":"474","DOI":"10.1016\/j.molcata.2016.07.002","volume":"426","author":"Lavoie","year":"2017","journal-title":"J. Mol. Catal. A Chem."},{"key":"hb7985_bb26","doi-asserted-by":"crossref","first-page":"3003","DOI":"10.1039\/C4GC00406J","volume":"16","author":"Li","year":"2014","journal-title":"Green Chem."},{"key":"hb7985_bb27","doi-asserted-by":"crossref","first-page":"7598","DOI":"10.1021\/ic2005985","volume":"50","author":"Liu","year":"2011","journal-title":"Inorg. Chem."},{"key":"hb7985_bb28","doi-asserted-by":"crossref","first-page":"8857","DOI":"10.1016\/j.tet.2012.08.061","volume":"68","author":"Lu","year":"2012","journal-title":"Tetrahedron"},{"key":"hb7985_bb29","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1016\/j.synthmet.2016.05.010","volume":"219","author":"Luke\u0161","year":"2016","journal-title":"Synth. Met."},{"key":"hb7985_bb30","doi-asserted-by":"crossref","first-page":"8830","DOI":"10.1016\/j.tet.2008.06.079","volume":"64","author":"Matsui","year":"2008","journal-title":"Tetrahedron"},{"key":"hb7985_bb31","doi-asserted-by":"crossref","first-page":"6422","DOI":"10.1039\/C6SC01974A","volume":"7","author":"Maugeri","year":"2016","journal-title":"Chem. Sci."},{"key":"hb7985_bb32","doi-asserted-by":"crossref","first-page":"1986","DOI":"10.1021\/acs.joc.6b02822","volume":"82","author":"Maugeri","year":"2017","journal-title":"J. Org. Chem."},{"key":"hb7985_bb33","doi-asserted-by":"crossref","first-page":"737","DOI":"10.1126\/science.1261043","volume":"347","author":"Milo","year":"2015","journal-title":"Science"},{"key":"hb7985_bb34","unstructured":"Mohamed, H. A., Alotaibi, H. A., Kariuki, B. M. & El-Hiti, G. A. (2021). CSD Communication (CCDC 1861196). CCDC, Cambridge, England. https:\/\/doi.org\/10.5517\/ccdc.csd.cc20gqlt."},{"key":"hb7985_bb35","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1016\/j.jfluchem.2019.05.008","volume":"224","author":"Moseev","year":"2019","journal-title":"J. Fluor. Chem."},{"key":"hb7985_bb36","doi-asserted-by":"crossref","first-page":"1241","DOI":"10.1134\/S107042801908027X","volume":"55","author":"Pokhodylo","year":"2019","journal-title":"Russ. J. Org. Chem."},{"key":"hb7985_bb37","doi-asserted-by":"crossref","first-page":"1096","DOI":"10.1080\/00397911.2017.1313427","volume":"47","author":"Pokhodylo","year":"2017","journal-title":"Synth. Commun."},{"key":"hb7985_bb38","doi-asserted-by":"crossref","first-page":"260","DOI":"10.1002\/slct.201904688","volume":"5","author":"Pokhodylo","year":"2020","journal-title":"ChemistrySelect"},{"key":"hb7985_bb39","doi-asserted-by":"crossref","first-page":"5871","DOI":"10.1002\/slct.201700577","volume":"2","author":"Pokhodylo","year":"2017","journal-title":"ChemistrySelect"},{"key":"hb7985_bb40","doi-asserted-by":"crossref","first-page":"1002","DOI":"10.1080\/00397911.2013.840729","volume":"44","author":"Pokhodylo","year":"2014","journal-title":"Synth. Commun."},{"key":"hb7985_bb41","doi-asserted-by":"crossref","first-page":"773","DOI":"10.1007\/s10593-018-2348-1","volume":"54","author":"Pokhodylo","year":"2018","journal-title":"Chem. Heterocycl. Compd"},{"key":"hb7985_bb42","doi-asserted-by":"crossref","first-page":"9143","DOI":"10.1002\/chem.200801325","volume":"14","author":"Ramachary","year":"2008","journal-title":"Chem. Eur. J."},{"key":"hb7985_bb43","unstructured":"Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Tokyo, Japan."},{"key":"hb7985_bb44","doi-asserted-by":"crossref","first-page":"11014","DOI":"10.1002\/anie.201205831","volume":"51","author":"Rillahan","year":"2012","journal-title":"Angew. Chem. Int. Ed."},{"key":"hb7985_bb45","doi-asserted-by":"crossref","first-page":"614","DOI":"10.1016\/j.tet.2011.10.110","volume":"68","author":"Rozin","year":"2012","journal-title":"Tetrahedron"},{"key":"hb7985_bb46","doi-asserted-by":"crossref","first-page":"704","DOI":"10.1007\/s10593-019-02525-2","volume":"55","author":"Shafran","year":"2019","journal-title":"Chem. Heterocycl. Compd"},{"key":"hb7985_bb47","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"hb7985_bb50","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"hb7985_bb51","doi-asserted-by":"crossref","unstructured":"Singh, S., El-Sakkary, N., Skinner, D. E., Sharma, P. P., Ottilie, S., Antonova-Koch, Y., Kumar, P., Winzeler, E., Caffrey, C. R. & Rathi, B. (2020). Pharmaceuticals, 13, 25. https:\/\/doi.org\/10.3390\/ph13020025.","DOI":"10.3390\/ph13020025"},{"key":"hb7985_bb52","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1039\/B818330A","volume":"11","author":"Spackman","year":"2009","journal-title":"CrystEngComm"},{"key":"hb7985_bb53","doi-asserted-by":"crossref","first-page":"278","DOI":"10.1016\/j.dyepig.2012.08.012","volume":"96","author":"Tomkute-Luksiene","year":"2013","journal-title":"Dyes Pigments"},{"key":"hb7985_bb54","unstructured":"Turner, M. J., Mckinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17. The University of Western Australia. http:\/\/hirshfeldsurface.net"},{"key":"hb7985_bb55","doi-asserted-by":"crossref","first-page":"o1724","DOI":"10.1107\/S1600536813029425","volume":"69","author":"Vinutha","year":"2013","journal-title":"Acta Cryst. E"},{"key":"hb7985_bb56","doi-asserted-by":"crossref","first-page":"2633","DOI":"10.1016\/j.tetlet.2013.03.030","volume":"54","author":"Wang","year":"2013","journal-title":"Tetrahedron Lett."},{"key":"hb7985_bb57","doi-asserted-by":"crossref","first-page":"2958","DOI":"10.1021\/ja511457g","volume":"137","author":"Xie","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"hb7985_bb58","doi-asserted-by":"crossref","first-page":"4295","DOI":"10.1039\/c1ob05176h","volume":"9","author":"Zeghada","year":"2011","journal-title":"Org. Biomol. Chem."},{"key":"hb7985_bb59","doi-asserted-by":"crossref","first-page":"1195","DOI":"10.1107\/S2056989018010885","volume":"74","author":"Zukerman-Schpector","year":"2018","journal-title":"Acta Cryst. E"}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2021\/11\/00\/hb7985\/hb7985.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2021\/11\/00\/hb7985\/hb7985.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T10:40:25Z","timestamp":1736764825000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989021010070"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,10,5]]},"references-count":55,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2021,11]]}},"alternative-id":["S2056989021010070"],"URL":"https:\/\/doi.org\/10.1107\/s2056989021010070","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989021010070\/hb7985sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989021010070\/hb7985Isup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989021010070\/hb7985Isup4.cml","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989021010070\/hb7985sup3.pdf","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"type":"electronic","value":"2056-9890"}],"subject":[],"published":{"date-parts":[[2021,10,5]]},"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":"https:\/\/scripts.iucr.org\/cgi-bin\/citedin?hb7985","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":"20 September 2021","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"28 September 2021","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"5 October 2021","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":"https:\/\/scripts.iucr.org\/cgi-bin\/sendsup?hb7985"}},{"value":"\u00a9 2021 Pokhodylo 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"}}]}}