{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T17:53:09Z","timestamp":1791222789500,"version":"4.1.0"},"reference-count":41,"publisher":"International Union of Crystallography (IUCr)","issue":"10","license":[{"start":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T00:00:00Z","timestamp":1788825600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T00:00:00Z","timestamp":1788825600000},"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":[[2026,8,31]]},"published-print":{"date-parts":[[2026,10,1]]},"abstract":"<jats:p>\n                    The title molecule, C\n                    <jats:sub>9<\/jats:sub>\n                    H\n                    <jats:sub>10<\/jats:sub>\n                    N\n                    <jats:sub>2<\/jats:sub>\n                    , exhibits whole-molecule disorder in a 0.849\u2005(4)\/0.151\u2005(4) ratio. The bicyclic portion is planar. In the crystal, a layer structure parallel to the\n                    <jats:italic>ac<\/jats:italic>\n                    plane is generated by N\u2014H...N hydrogen bonds and C\u2014H...\u03c0(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H, C...H\/H...C and N...H\/H...N interactions.\n                  <\/jats:p>","DOI":"10.1107\/s2056989026009072","type":"journal-article","created":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T10:24:46Z","timestamp":1788431086000},"page":"1154-1159","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Crystal structure and Hirshfeld surface analysis of 2,5-dimethyl-1\n                    <i>H<\/i>\n                    -benzo[\n                    <i>d<\/i>\n                    ]imidazole"],"prefix":"10.1107","volume":"82","author":[{"ORCID":"https:\/\/orcid.org\/0009-0007-5232-2852","authenticated-orcid":true,"given":"Achrafe","family":"Oulhaj","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/00r8w8f84","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jihad","family":"Sebhaoui","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gamal","family":"Al Ati","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/00r8w8f84","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fares Hezam","family":"Al-Ostoot","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":"El Mokhtar","family":"Essassi","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/00r8w8f84","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Adam","family":"Duong","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9996-4963","authenticated-orcid":true,"given":"Karim","family":"Chkirate","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/00r8w8f84","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2026,9,8]]},"reference":[{"key":"vm2334_bb1","first-page":"e02881G","volume":"10","author":"Al Ati","year":"2025","journal-title":"Chem. Select."},{"key":"vm2334_bb2","doi-asserted-by":"crossref","first-page":"300","DOI":"10.3390\/cryst16050300","volume":"16","author":"Arzine","year":"2026","journal-title":"Crystals"},{"key":"vm2334_bb3","doi-asserted-by":"crossref","first-page":"120142","DOI":"10.1016\/j.jelechem.2026.120142","volume":"1013","author":"Azgaou","year":"2026","journal-title":"J. Electroanal. Chem."},{"key":"vm2334_bb4","doi-asserted-by":"crossref","first-page":"7847","DOI":"10.1080\/07391102.2023.2242496","volume":"42","author":"Bal","year":"2024","journal-title":"J. Biomol. Struct. Dyn."},{"key":"vm2334_bb5","unstructured":"Brandenburg, K. & Putz, H. (2012). DIAMOND Crystal Impact GbR, Bonn, Germany."},{"key":"vm2334_bb6","unstructured":"Bruker (2021). APEX4 and SAINT. Bruker AXS LLC, Madison, Wisconsin, USA."},{"key":"vm2334_bb7","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1023\/A:1021766300133","volume":"28","author":"Caira","year":"1998","journal-title":"J. Chem. Crystallogr."},{"key":"vm2334_bb8","doi-asserted-by":"crossref","first-page":"635","DOI":"10.1002\/cjoc.201300217","volume":"31","author":"Chen","year":"2013","journal-title":"Chin. J. Chem."},{"key":"vm2334_bb9","doi-asserted-by":"crossref","first-page":"6221","DOI":"10.1039\/c2ce25724f","volume":"14","author":"Chen","year":"2012","journal-title":"CrystEngComm"},{"key":"vm2334_bb10","doi-asserted-by":"crossref","first-page":"e202300331","DOI":"10.1002\/cbic.202300331","volume":"24","author":"Chkirate","year":"2023","journal-title":"ChemBioChem"},{"key":"vm2334_bb11","doi-asserted-by":"crossref","first-page":"2210","DOI":"10.1039\/C9NJ05913J","volume":"44","author":"Chkirate","year":"2020","journal-title":"New J. Chem."},{"key":"vm2334_bb12","first-page":"3097","volume":"15","author":"Deb","year":"2024","journal-title":"Med. Chem."},{"key":"vm2334_bb13","first-page":"203","volume":"15","author":"Ding","year":"2005","journal-title":"Ind. J. Heterocycl. Chem"},{"key":"vm2334_bb14","doi-asserted-by":"crossref","first-page":"o3227","DOI":"10.1107\/S1600536809049770","volume":"65","author":"Eltayeb","year":"2009","journal-title":"Acta Cryst. E"},{"key":"vm2334_bb15","doi-asserted-by":"crossref","first-page":"o1613","DOI":"10.1107\/S1600536809022478","volume":"65","author":"Eltayeb","year":"2009","journal-title":"Acta Cryst. E"},{"key":"vm2334_bb16","doi-asserted-by":"crossref","first-page":"17614","DOI":"10.1002\/anie.202006392","volume":"59","author":"Fares","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"vm2334_bb17","doi-asserted-by":"crossref","first-page":"2245","DOI":"10.1016\/j.ejmech.2010.01.067","volume":"45","author":"Gaba","year":"2010","journal-title":"Eur. J. Med. Chem."},{"key":"vm2334_bb18","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/j.inoche.2014.01.019","volume":"42","author":"Geng","year":"2014","journal-title":"Inorg. Chem. Commun."},{"key":"vm2334_bb19","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Cryst. B"},{"key":"vm2334_bb20","doi-asserted-by":"crossref","first-page":"379","DOI":"10.1021\/jm800984v","volume":"52","author":"Howard","year":"2009","journal-title":"J. Med. Chem."},{"key":"vm2334_bb21","doi-asserted-by":"crossref","first-page":"396","DOI":"10.1107\/S2056989021002723","volume":"77","author":"Idrissi","year":"2021","journal-title":"Acta Cryst. E"},{"key":"vm2334_bb22","doi-asserted-by":"crossref","first-page":"616","DOI":"10.1016\/j.ejmech.2014.10.079","volume":"89","author":"Jose","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"vm2334_bb23","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S1600576714022985","volume":"48","author":"Krause","year":"2015","journal-title":"J. Appl. Cryst."},{"key":"vm2334_bb24","first-page":"1993","volume":"13","author":"Ksama","year":"2025","journal-title":"Mor. J. Chem."},{"key":"vm2334_bb25","unstructured":"Kubicki, M. (2025). CSD Communication (refcode ARUQUD). CCDC, Cambridge, England."},{"key":"vm2334_bb26","doi-asserted-by":"crossref","first-page":"3814","DOI":"10.1039\/b704980c","author":"McKinnon","year":"2007","journal-title":"Chem. Commun."},{"key":"vm2334_bb27","doi-asserted-by":"crossref","first-page":"144829","DOI":"10.1016\/j.molstruc.2025.144829","volume":"1353","author":"Oufkir","year":"2026","journal-title":"J. Mol. Struct."},{"key":"vm2334_bb28","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1107\/S2052519213010014","volume":"69","author":"Parsons","year":"2013","journal-title":"Acta Cryst. B"},{"key":"vm2334_bb29","doi-asserted-by":"crossref","first-page":"o1184","DOI":"10.1107\/S1600536805009414","volume":"61","author":"Ravishankar","year":"2005","journal-title":"Acta Cryst. E"},{"key":"vm2334_bb30","doi-asserted-by":"crossref","first-page":"36","DOI":"10.1016\/j.poly.2014.03.047","volume":"76","author":"Seber","year":"2014","journal-title":"Polyhedron"},{"key":"vm2334_bb41","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Cryst. A"},{"key":"vm2334_bb31","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"vm2334_bb32","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"vm2334_bb33","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."},{"key":"vm2334_bb34","doi-asserted-by":"crossref","first-page":"1903","DOI":"10.1107\/S2056989018016791","volume":"74","author":"White","year":"2018","journal-title":"Acta Cryst. E"},{"key":"vm2334_bb35","unstructured":"White, J. M. & Fellowes, T. (2019). CSD Communication (refcode LOWNAP). CCDC, Cambridge, England."},{"key":"vm2334_bb36","unstructured":"White, J. M., Hu, H. & Skene, C. (2019a). CSD Communication (refcode TUBVOE). CCDC, Cambridge, England."},{"key":"vm2334_bb37","unstructured":"White, J. M., Skene, C. E. & Martin, R. F. (2014). CSD Communication (refcode HONLUT). CCDC, Cambridge, England."},{"key":"vm2334_bb38","unstructured":"White, J. M., Skene, C. E. & Martin, R. F. (2019b). CSD Communication (refcode TUBZEY). CCDC, Cambridge, England."},{"key":"vm2334_bb39","doi-asserted-by":"crossref","first-page":"o1256","DOI":"10.1107\/S1600536809016523","volume":"65","author":"Xiao","year":"2009","journal-title":"Acta Cryst. E"},{"key":"vm2334_bb40","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1007\/s10870-018-0725-3","volume":"48","author":"Yeong","year":"2018","journal-title":"J. Chem. Crystallogr."}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2026\/10\/00\/vm2334\/vm2334.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2026\/10\/00\/vm2334\/vm2334.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T17:12:26Z","timestamp":1791220346000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989026009072"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,8]]},"references-count":41,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2026,10]]}},"alternative-id":["S2056989026009072"],"URL":"https:\/\/doi.org\/10.1107\/s2056989026009072","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989026009072\/vm2334sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989026009072\/vm2334Isup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989026009072\/vm2334Isup3.cml","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"value":"2056-9890","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,8]]},"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?vm2334","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 August 2026","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"31 August 2026","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"8 September 2026","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?vm2334"}},{"value":"\u00a9 2026 Oulhaj\n                      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"}}]}}