{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,7]],"date-time":"2026-08-07T16:00:28Z","timestamp":1786118428956,"version":"build-2736575974"},"reference-count":0,"publisher":"International Union of Crystallography (IUCr)","issue":"8","license":[{"start":{"date-parts":[[2026,7,10]],"date-time":"2026-07-10T00:00:00Z","timestamp":1783641600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2026,7,10]],"date-time":"2026-07-10T00:00:00Z","timestamp":1783641600000},"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":[[2026,6,27]]},"published-print":{"date-parts":[[2026,8,1]]},"abstract":"\n Two\n N<\/jats:italic>\n -alkyl derivatives of 2-methoxy-5-nitroaniline, namely, 2-methoxy-\n N<\/jats:italic>\n -(4-methylbenzyl)-5-nitroaniline (C\n 15<\/jats:sub>\n H\n 16<\/jats:sub>\n N\n 2<\/jats:sub>\n O\n 3<\/jats:sub>\n , orange crystals) and 2-methoxy-5-nitro-\n N<\/jats:italic>\n -(triphenylmethyl)aniline ethanol quatersolvate (C\n 26<\/jats:sub>\n H\n 22<\/jats:sub>\n N\n 2<\/jats:sub>\n O\n 3<\/jats:sub>\n \u00b70.25C\n 2<\/jats:sub>\n H\n 5<\/jats:sub>\n OH, yellow crystals), have been prepared and analyzed by single-crystal X-ray diffraction to determine if these compounds display the same face-to-face \u03c0-stacking arrangement as observed in the un-alkylated parent compound. The triphenylmethyl derivative crystallizes with 0.25 ethanol molecules, the contribution of which has been modeled with a solvent mask due to a high degree of disorder. The UV-Vis spectra show that the benzyl derivative displays concentration-dependent shifts in the visible portion of the spectrum, shifting to longer wavelengths with higher concentration, which is attributed to aggregation in solution. This behavior is similar to that observed for the parent compound. In contrast, the triphenylmethyl derivative shows an attenuated concentration dependence on visible absorption, which does not display as great a red shift, and therefore represents a lesser tendency for aggregation in solution. The crystal packing for these compounds is distinguishing, with the benzyl derivative \u03c0-stacking in a face-to-face manner with dipole moments oriented anti-parallel, while the sterically demanding triphenylmethyl group prevents direct \u03c0-stacking for this compound. The packing observed for these compounds supports the hypothesis that an intermolecular charge-transfer process is responsible for the orange color of crystals of the benzyl derivative. It is concluded that sterically undemanding groups attached at the amino group could deliver materials which mimic the color center formation hypothesized for the parent compound. These types of structural changes may have useful applications in the field of organic semiconductors.\n <\/jats:p>","DOI":"10.1107\/s205698902600681x","type":"journal-article","created":{"date-parts":[[2026,7,10]],"date-time":"2026-07-10T09:21:09Z","timestamp":1783675269000},"page":"903-908","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Crystal structures of 2-methoxy-5-nitroaniline\n N<\/i>\n -alkyl derivatives support color-center creation by a dipole-stacking mechanism"],"prefix":"10.1107","volume":"82","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6014-3121","authenticated-orcid":true,"given":"Jonathan","family":"Filley","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ethan J.","family":"Crace","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2026,7,10]]},"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2026\/08\/00\/wm5804\/wm5804.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2026\/08\/00\/wm5804\/wm5804.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,6]],"date-time":"2026-08-06T15:46:19Z","timestamp":1786031179000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S205698902600681X"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,10]]},"references-count":0,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2026,8]]}},"alternative-id":["S205698902600681X"],"URL":"https:\/\/doi.org\/10.1107\/s205698902600681x","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S205698902600681X\/wm5804sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S205698902600681X\/wm58042sup3.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S205698902600681X\/wm58041sup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S205698902600681X\/wm58042sup4.cml","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S205698902600681X\/wm58041sup5.cml","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"value":"2056-9890","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,7,10]]},"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?wm5804","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 May 2026","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"27 June 2026","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"10 July 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?wm5804"}},{"value":"\u00a9 2026 Filley and Crace","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"}}]}}