{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T21:49:36Z","timestamp":1740174576565,"version":"3.37.3"},"reference-count":29,"publisher":"International Union of Crystallography (IUCr)","issue":"10","license":[{"start":{"date-parts":[[2022,9,27]],"date-time":"2022-09-27T00:00:00Z","timestamp":1664236800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2022,9,27]],"date-time":"2022-09-27T00:00:00Z","timestamp":1664236800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/501100000923","name":"Australian Research Council","doi-asserted-by":"publisher","award":["DP160100597","DP180101957"],"award-info":[{"award-number":["DP160100597","DP180101957"]}],"id":[{"id":"10.13039\/501100000923","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001164","name":"Australian Synchrotron","doi-asserted-by":"publisher","award":["13618b"],"award-info":[{"award-number":["13618b"]}],"id":[{"id":"10.13039\/501100001164","id-type":"DOI","asserted-by":"publisher"}]}],"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":[[2022,9,21]]},"published-print":{"date-parts":[[2022,10,1]]},"abstract":"<jats:p>The structure of the title compound, 2C<jats:sub>18<\/jats:sub>H<jats:sub>19<\/jats:sub>ClN<jats:sub>4<\/jats:sub>O\u00b7HCl or (CNO)<jats:sub>2<\/jats:sub>\u00b7HCl (C<jats:sub>36<\/jats:sub>H<jats:sub>39<\/jats:sub>Cl<jats:sub>3<\/jats:sub>N<jats:sub>8<\/jats:sub>O<jats:sub>2<\/jats:sub>), at 100\u2005K has tetragonal (<jats:italic>I<\/jats:italic>4\/<jats:italic>m<\/jats:italic>) symmetry. The dihedral angle between the benzene rings of the fused ring system of the CNO molecule is 40.08\u2005(6)\u00b0 and the equivalent angle between the seven-membered ring and its pendant <jats:italic>N<\/jats:italic>-oxide ring is 31.14\u2005(7)\u00b0. The structure contains a very strong, symmetrical O\u2014H...O hydrogen bond [O...O = 2.434\u2005(2)\u2005\u00c5] between two equivalent <jats:italic>R<\/jats:italic>\n                  <jats:sub>3<\/jats:sub>N<jats:sup>+<\/jats:sup>\u2014O<jats:sup>\u2212<\/jats:sup> moieties, which share a proton lying on a crystallographic twofold rotation axis. These units then form a (CNO)<jats:sub>4<\/jats:sub>\u00b7(HCl)<jats:sub>2<\/jats:sub> ring by way of two equivalent N\u2014H...Cl hydrogen bonds (Cl<jats:sup>\u2212<\/jats:sup> site symmetry <jats:italic>m<\/jats:italic>). These rings are catenated into infinite chains propagating along the <jats:italic>c<\/jats:italic>-axis direction by way of shape complementarity and directional C\u2014H...N and C\u2014H...\u03c0 interactions.<\/jats:p>","DOI":"10.1107\/s2056989022009306","type":"journal-article","created":{"date-parts":[[2022,9,27]],"date-time":"2022-09-27T07:46:04Z","timestamp":1664264764000},"page":"1056-1060","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis and structure of clozapine <i>N<\/i>-oxide hemi(hydrochloride): an infinite hydrogen-bonded poly[<i>n<\/i>]catenane"],"prefix":"10.1107","volume":"78","author":[{"given":"Phillip L. van der","family":"Peet","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rohan D.","family":"Joyce","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6602-6404","authenticated-orcid":true,"given":"Holger","family":"Ott","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sebastian M.","family":"Marcuccio","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jonathan M.","family":"White","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6341-4364","authenticated-orcid":true,"given":"Spencer J.","family":"Williams","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2022,9,27]]},"reference":[{"key":"hb8039_bb1","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1124\/jpet.118.252031","volume":"368","author":"Allen","year":"2019","journal-title":"J. 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