{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T09:55:15Z","timestamp":1785405315750,"version":"3.56.0"},"reference-count":24,"publisher":"International Union of Crystallography (IUCr)","issue":"12","license":[{"start":{"date-parts":[[2024,11,8]],"date-time":"2024-11-08T00:00:00Z","timestamp":1731024000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2024,11,8]],"date-time":"2024-11-08T00:00:00Z","timestamp":1731024000000},"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":[[2024,11,2]]},"published-print":{"date-parts":[[2024,12,1]]},"abstract":"<jats:p>\n                    The etoxazole metabolite\n                    <jats:bold>R13<\/jats:bold>\n                    , systematic name 4-(4-\n                    <jats:italic>tert<\/jats:italic>\n                    -butyl-2-ethoxyphenyl)-2-(2,6-difluorophenyl)oxazole (C\n                    <jats:sub>21<\/jats:sub>\n                    H\n                    <jats:sub>21<\/jats:sub>\n                    F\n                    <jats:sub>2<\/jats:sub>\n                    NO\n                    <jats:sub>2<\/jats:sub>\n                    ), results from the oxidation of etoxazole, a chitin synthesis inhibitor belonging to the oxazoline class, widely used as an insecticide\/acaricide since 1998. The structure of\n                    <jats:bold>R13<\/jats:bold>\n                    features a central oxazole ring with attached 2,6-difluorophenyl and 4-\n                    <jats:italic>t<\/jats:italic>\n                    -butyl-2-ethoxyphenyl moieties. The overall conformation gives dihedral angles between these rings and the oxazole of 24.91\u2005(5)\u00b0 (with difluorophenyl) and 15.30\u2005(6)\u00b0 (with\n                    <jats:italic>t<\/jats:italic>\n                    -butyl-ethoxyphenyl), indicating an overall deviation from planarity. Additionally, torsion angles of the ethoxy and\n                    <jats:italic>t<\/jats:italic>\n                    -butyl groups define the orientation of these substituents relative to their benzene ring. In the crystal packing, no significant hydrogen bonds are present, but a Hirshfeld surface analysis highlights weak intermolecular contacts leading to \u03c0\u2013\u03c0-stacked dimers linked by weak C\u2014H...N contacts. The packing analysis confirms that most intermolecular interactions involve hydrogen atoms.\n                  <\/jats:p>","DOI":"10.1107\/s2056989024010600","type":"journal-article","created":{"date-parts":[[2024,11,6]],"date-time":"2024-11-06T05:44:42Z","timestamp":1730871882000},"page":"1270-1273","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":4,"title":["Crystal structure and Hirshfeld-surface analysis of an etoxazole metabolite designated R13"],"prefix":"10.1107","volume":"80","author":[{"given":"Thaluru M.","family":"Mohan Kumar","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Besagarahally L.","family":"Bhaskar","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Prabhakar","family":"Priyanka","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thayamma R.","family":"Divakara","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9039-0273","authenticated-orcid":true,"given":"Hemmige S.","family":"Yathirajan","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/012bxv356","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5777-3918","authenticated-orcid":true,"given":"Sean","family":"Parkin","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/02k3smh20","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2024,11,8]]},"reference":[{"key":"nx2015_bb1","unstructured":"APVMA. 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