{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,26]],"date-time":"2026-06-26T10:47:55Z","timestamp":1782470875911,"version":"3.54.5"},"reference-count":32,"publisher":"International Union of Crystallography (IUCr)","issue":"8","license":[{"start":{"date-parts":[[2021,7,27]],"date-time":"2021-07-27T00:00:00Z","timestamp":1627344000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2021,7,27]],"date-time":"2021-07-27T00:00:00Z","timestamp":1627344000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/100007875","name":"Tulane University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100007875","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Hacettepe University Scientific Research Project Unit","award":["013 D04 602 004"],"award-info":[{"award-number":["013 D04 602 004"]}]}],"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":[[2021,7,19]]},"published-print":{"date-parts":[[2021,8,1]]},"abstract":"<jats:p>The title compound {systematic name: (<jats:italic>S<\/jats:italic>,<jats:italic>E<\/jats:italic>)-3-[4-(furan-2-yl)-2,3,4,5-tetrahydro-1<jats:italic>H<\/jats:italic>-benzo[<jats:italic>b<\/jats:italic>][1,4]diazepin-2-ylidene]-6-methyl-2<jats:italic>H<\/jats:italic>-pyran-2,4(3<jats:italic>H<\/jats:italic>)-dione}, C<jats:sub>19<\/jats:sub>H<jats:sub>16<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>4<\/jats:sub>, is constructed from a benzodiazepine ring system linked to furan and pendant dihydropyran rings, where the benzene and furan rings are oriented at a dihedral angle of 48.7\u2005(2)\u00b0. The pyran ring is modestly non-planar [largest deviation of 0.029\u2005(4)\u2005\u00c5 from the least-squares plane] while the tetrahydrodiazepine ring adopts a boat conformation. The rotational orientation of the pendant dihydropyran ring is partially determined by an intramolecular N\u2014H<jats:sub>Diazp<\/jats:sub>...O<jats:sub>Dhydp<\/jats:sub> (Diazp = diazepine and Dhydp = dihydropyran) hydrogen bond. In the crystal, layers of molecules parallel to the <jats:italic>bc<\/jats:italic> plane are formed by N\u2014H<jats:sub>Diazp<\/jats:sub>...O<jats:sub>Dhydp<\/jats:sub> hydrogen bonds and slipped \u03c0\u2013\u03c0 stacking interactions. The layers are connected by additional slipped \u03c0\u2013\u03c0 stacking interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (46.8%), H...O\/O...H (23.5%) and H...C\/C...H (15.8%) interactions, indicating that van der Waals interactions are the dominant forces in the crystal packing. Computational chemistry indicates that in the crystal the N\u2014H...O hydrogen-bond energy is 57.5\u2005kJ\u2005mol<jats:sup>\u22121<\/jats:sup>.<\/jats:p>","DOI":"10.1107\/s2056989021007441","type":"journal-article","created":{"date-parts":[[2021,7,27]],"date-time":"2021-07-27T08:33:12Z","timestamp":1627374792000},"page":"834-838","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":2,"title":["Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 4-(furan-2-yl)-2-(6-methyl-2,4-dioxopyran-3-ylidene)-2,3,4,5-tetrahydro-1<i>H<\/i>-1,5-benzodiazepine"],"prefix":"10.1107","volume":"77","author":[{"given":"Mohamed","family":"El Hafi","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sanae","family":"Lahmidi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lhoussaine","family":"El Ghayati","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tuncer","family":"H\u00f6kelek","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3488-1945","authenticated-orcid":true,"given":"Joel T.","family":"Mague","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bushra","family":"Amer","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nada Kheira","family":"Sebbar","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"El Mokhtar","family":"Essassi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2021,7,27]]},"reference":[{"key":"wm5612_bb1","doi-asserted-by":"crossref","first-page":"110","DOI":"10.1111\/cbdd.12739","volume":"88","author":"An","year":"2016","journal-title":"Chem. 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