{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,27]],"date-time":"2026-08-27T01:39:29Z","timestamp":1787794769805,"version":"build-2784847793"},"reference-count":0,"publisher":"International Union of Crystallography (IUCr)","issue":"3","license":[{"start":{"date-parts":[[2023,2,9]],"date-time":"2023-02-09T00:00:00Z","timestamp":1675900800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2023,2,9]],"date-time":"2023-02-09T00:00:00Z","timestamp":1675900800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/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"],"accepted":{"date-parts":[[2023,2,3]]},"published-print":{"date-parts":[[2023,3,1]]},"abstract":"<jats:p>The title compound, C<jats:sub>16<\/jats:sub>H<jats:sub>11<\/jats:sub>N<jats:sub>3<\/jats:sub>O<jats:sub>3<\/jats:sub>, belongs to the family of azo dyes. In the light of a single-crystal X-ray study, it is evident that of the tautomeric forms (azo\u2013hydrazone), the hydrazone form is the predominant form in the solid state, namely, (1<jats:italic>E<\/jats:italic>)-1-[2-(3-nitrophenyl)hydrazin-1-ylidene]-1,2-dihydronaphthalen-2-one. The naphthol and benzene fragments attached to the \u2013N=N\u2013 moiety adopt the <jats:italic>s-trans<\/jats:italic> conformation. Furthermore, the molecules are nearly coplanar, subtending a dihedral angle of 2.63\u2005(5)\u00b0. An intramolecular N\u2014H...O hydrogen bond occurs. There are only two types of intermolecular interactions in the crystal structure: strong hydrogen-bonding C\u2014H...O interactions and \u03c0\u2013\u03c0 stacking interactions. The importance of C\u2014H...O interactions in the molecular packing is reflected by the relatively high contributions (28.5%) made by O...H\/H...O contacts to the Hirshfeld surface.<\/jats:p>","DOI":"10.1107\/s2056989023001068","type":"journal-article","created":{"date-parts":[[2023,2,9]],"date-time":"2023-02-09T16:09:42Z","timestamp":1675958982000},"page":"142-145","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":3,"title":["Crystal structure and Hirshfeld surface analysis of 1-[(<i>E<\/i>)-2-(3-nitrophenyl)diazen-1-yl]naphthalen-2-ol"],"prefix":"10.1107","volume":"79","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3603-8655","authenticated-orcid":true,"given":"Mohamed Amine","family":"Benaouida","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4829-9008","authenticated-orcid":true,"given":"Ali","family":"Benosmane","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2815-6555","authenticated-orcid":true,"given":"Mehdi","family":"Boutebdja","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hocine","family":"Merazig","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2023,2,9]]},"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2023\/03\/00\/zn2025\/zn2025.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2023\/03\/00\/zn2025\/zn2025.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T11:16:06Z","timestamp":1736766966000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989023001068"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,2,9]]},"references-count":0,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2023,3]]}},"alternative-id":["S2056989023001068"],"URL":"https:\/\/doi.org\/10.1107\/s2056989023001068","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989023001068\/zn2025sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989023001068\/zn2025Isup2.cml","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"value":"2056-9890","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,2,9]]},"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?zn2025","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":"4 January 2023","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"3 February 2023","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"9 February 2023","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?zn2025"}},{"value":"\u00a9 2023 Benaouida 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"}}]}}