{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,6]],"date-time":"2026-05-06T23:53:39Z","timestamp":1778111619364,"version":"3.51.4"},"reference-count":32,"publisher":"International Union of Crystallography (IUCr)","issue":"7","license":[{"start":{"date-parts":[[2025,6,6]],"date-time":"2025-06-06T00:00:00Z","timestamp":1749168000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2025,6,6]],"date-time":"2025-06-06T00:00:00Z","timestamp":1749168000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"name":"RUDN University Scientific Projects Grant System","award":["021408\u20132-000"],"award-info":[{"award-number":["021408\u20132-000"]}]},{"name":"Baku Engineering University"},{"name":"Azerbaijan Medical University"}],"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":[[2025,5,29]]},"published-print":{"date-parts":[[2025,7,1]]},"abstract":"<jats:p>In the title compound, C<jats:sub>16<\/jats:sub>H<jats:sub>17<\/jats:sub>BF<jats:sub>2<\/jats:sub>N<jats:sub>2<\/jats:sub>OSi, the molecular conformation is consolidated by an intramolecular C\u2014H...O hydrogen bond, forming an <jats:italic>S<\/jats:italic>(6) motif. In the crystal, pairs of molecules are connected by C\u2014H...\u03c0 and \u03c0\u2013\u03c0 interactions [centroid-to-centroid distance = 3.6155\u2005(8)\u2005\u00c5] between the furan rings. These dimers are linked by \u03c0\u2013\u03c0 interactions [centroid-to-centroid distance = 3.4041\u2005(9)\u2005\u00c5] between similar five-membered rings of the twelve-membered ring system, forming ribbons along the <jats:italic>a<\/jats:italic>-axis direction. As a result, the van der Waals interactions between the ribbons provide crystal cohesion. Hirshfeld surface analysis indicates that H...H (48.6%), F...H\/H...F (19.8%) and C...H\/H...C (19.0%) interactions make the most significant contributions to the crystal packing.<\/jats:p>","DOI":"10.1107\/s2056989025004888","type":"journal-article","created":{"date-parts":[[2025,6,6]],"date-time":"2025-06-06T01:57:47Z","timestamp":1749175067000},"page":"582-586","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["Crystal structure and Hirshfeld surface analysis of 5,5-difluoro-10-[5-(trimethylsilyl)furan-2-yl]-5<i>H<\/i>-4\u03bb<sup>4<\/sup>,5\u03bb<sup>4<\/sup>-dipyrrolo[1,2-<i>c<\/i>:2\u2032,1\u2032-<i>f<\/i>][1,3,2]diazaborinine"],"prefix":"10.1107","volume":"81","author":[{"given":"Dmitriy M.","family":"Shchevnikov","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexandra G.","family":"Kutasevich","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8806-2975","authenticated-orcid":true,"given":"Victor N.","family":"Khrustalev","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Narmina A.","family":"Guliyeva","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Khudayar I.","family":"Hasanov","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2421-0929","authenticated-orcid":true,"given":"Mehmet","family":"Akkurt","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6098-9450","authenticated-orcid":true,"given":"Gizachew Mulugeta","family":"Manahelohe","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2025,6,6]]},"reference":[{"key":"vm2314_bb1","doi-asserted-by":"crossref","first-page":"21","DOI":"10.1016\/j.jphotochemrev.2019.04.001","volume":"40","author":"Agazzi","year":"2019","journal-title":"J. Photochem. Photobiol. Photochem. Rev."},{"key":"vm2314_bb2","doi-asserted-by":"crossref","first-page":"1007","DOI":"10.1107\/S2056989020007033","volume":"76","author":"Askerov","year":"2020","journal-title":"Acta Cryst. E"},{"key":"vm2314_bb3","doi-asserted-by":"crossref","first-page":"1555","DOI":"10.1002\/anie.199515551","volume":"34","author":"Bernstein","year":"1995","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"vm2314_bb4","doi-asserted-by":"crossref","first-page":"213024","DOI":"10.1016\/j.ccr.2019.213024","volume":"399","author":"Boens","year":"2019","journal-title":"Coord. Chem. Rev."},{"key":"vm2314_bb5","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1107\/S0021889812029111","volume":"45","author":"Farrugia","year":"2012","journal-title":"J. Appl. Cryst."},{"key":"vm2314_bb6","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Cryst. B"},{"key":"vm2314_bb7","doi-asserted-by":"crossref","first-page":"1019","DOI":"10.1039\/D1DT03755B","volume":"51","author":"Gurbanov","year":"2022","journal-title":"Dalton Trans."},{"key":"vm2314_bb8","doi-asserted-by":"crossref","first-page":"4299","DOI":"10.1080\/00958972.2012.740023","volume":"65","author":"Jun","year":"2012","journal-title":"J. Coord. Chem."},{"key":"vm2314_bb9","doi-asserted-by":"crossref","first-page":"1201","DOI":"10.1142\/S1088424612501180","volume":"16","author":"Jun","year":"2012","journal-title":"J. Porphyrins Phthalocyanines"},{"key":"vm2314_bb10","first-page":"719","volume":"66","author":"Khalilov","year":"2021","journal-title":"Rev. Roum. Chim."},{"key":"vm2314_bb11","doi-asserted-by":"crossref","first-page":"257","DOI":"10.1016\/j.ica.2011.11.017","volume":"383","author":"Khan","year":"2012","journal-title":"Inorg. Chim. Acta"},{"key":"vm2314_bb12","doi-asserted-by":"crossref","first-page":"830","DOI":"10.1016\/j.tet.2011.11.048","volume":"68","author":"Khan","year":"2012","journal-title":"Tetrahedron"},{"key":"vm2314_bb13","doi-asserted-by":"crossref","first-page":"4881","DOI":"10.1021\/ic902467h","volume":"49","author":"Kim","year":"2010","journal-title":"Inorg. Chem."},{"key":"vm2314_bb14","doi-asserted-by":"crossref","first-page":"72","DOI":"10.1016\/j.jinorgbio.2012.05.008","volume":"115","author":"Kopylovich","year":"2012","journal-title":"J. Inorg. Biochem."},{"key":"vm2314_bb15","doi-asserted-by":"crossref","first-page":"4891","DOI":"10.1021\/cr078381n","volume":"107","author":"Loudet","year":"2007","journal-title":"Chem. Rev."},{"key":"vm2314_bb16","doi-asserted-by":"crossref","first-page":"e202203861","DOI":"10.1002\/chem.202203861","volume":"29","author":"Mahmudov","year":"2023","journal-title":"Chem. Eur. J."},{"key":"vm2314_bb17","doi-asserted-by":"crossref","first-page":"213462","DOI":"10.1016\/j.ccr.2020.213462","volume":"421","author":"Poddar","year":"2020","journal-title":"Coord. Chem. Rev."},{"key":"vm2314_bb18","doi-asserted-by":"crossref","first-page":"769","DOI":"10.3762\/bjoc.15.73","volume":"15","author":"Polyanskii","year":"2019","journal-title":"Beilstein J. Org. Chem."},{"key":"vm2314_bb19","doi-asserted-by":"crossref","first-page":"777","DOI":"10.1107\/S2056989024005826","volume":"80","author":"Pronina","year":"2024","journal-title":"Acta Cryst. E"},{"key":"vm2314_bb20","unstructured":"Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England."},{"key":"vm2314_bb21","doi-asserted-by":"crossref","first-page":"72","DOI":"10.1107\/S2056989023010800","volume":"80","author":"Sadikhova","year":"2024","journal-title":"Acta Cryst. E"},{"key":"vm2314_bb22","doi-asserted-by":"crossref","first-page":"5855","DOI":"10.1039\/C6NJ00118A","volume":"40","author":"Sharma","year":"2016","journal-title":"New J. Chem."},{"key":"vm2314_bb23","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"vm2314_bb24","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"vm2314_bb25","doi-asserted-by":"crossref","first-page":"1006","DOI":"10.1107\/S1600576721002910","volume":"54","author":"Spackman","year":"2021","journal-title":"J. Appl. Cryst."},{"key":"vm2314_bb26","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1107\/S2056989019016244","volume":"76","author":"Spek","year":"2020","journal-title":"Acta Cryst. E"},{"key":"vm2314_bb27","doi-asserted-by":"crossref","first-page":"208","DOI":"10.1002\/jlac.19687180119","volume":"718","author":"Treibs","year":"1968","journal-title":"Justus Liebigs Ann. Chem."},{"key":"vm2314_bb28","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1016\/j.ccr.2017.09.029","volume":"379","author":"Turksoy","year":"2019","journal-title":"Coord. Chem. Rev."},{"key":"vm2314_bb29","doi-asserted-by":"crossref","first-page":"1184","DOI":"10.1002\/anie.200702070","volume":"47","author":"Ulrich","year":"2008","journal-title":"Angew. Chem. Int. Ed."},{"key":"vm2314_bb30","doi-asserted-by":"crossref","first-page":"6018","DOI":"10.1039\/C9CE00959K","volume":"21","author":"Vel\u00e1squez","year":"2019","journal-title":"CrystEngComm"},{"key":"vm2314_bb31","doi-asserted-by":"crossref","first-page":"6181","DOI":"10.1002\/chem.201406550","volume":"21","author":"Zhao","year":"2015","journal-title":"Chem. Eur. J."},{"key":"vm2314_bb32","doi-asserted-by":"crossref","first-page":"2239","DOI":"10.1016\/j.tet.2016.03.023","volume":"72","author":"Zubkov","year":"2016","journal-title":"Tetrahedron"}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2025\/07\/00\/vm2314\/vm2314.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2025\/07\/00\/vm2314\/vm2314.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,7,22]],"date-time":"2025-07-22T11:48:22Z","timestamp":1753184902000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989025004888"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,6,6]]},"references-count":32,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2025,7]]}},"alternative-id":["S2056989025004888"],"URL":"https:\/\/doi.org\/10.1107\/s2056989025004888","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989025004888\/vm2314sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989025004888\/vm2314Isup2.hkl","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"value":"2056-9890","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,6,6]]},"assertion":[{"value":"Acta Crystallographica Section E: Crystallographic Communications","order":0,"name":"journal","label":"Publication","explanation":{"URL":"https:\/\/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?vm2314","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":"23 May 2025","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"29 May 2025","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"6 June 2025","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?vm2314"}},{"value":"\u00a9 2025 Shchevnikov et al.","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"https:\/\/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"}}]}}