{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,4,1]],"date-time":"2025-04-01T04:05:37Z","timestamp":1743480337870,"version":"3.40.3"},"reference-count":30,"publisher":"International Union of Crystallography (IUCr)","issue":"3","license":[{"start":{"date-parts":[[2025,2,14]],"date-time":"2025-02-14T00:00:00Z","timestamp":1739491200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2025,2,14]],"date-time":"2025-02-14T00:00:00Z","timestamp":1739491200000},"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":[[2025,2,11]]},"published-print":{"date-parts":[[2025,3,1]]},"abstract":"<jats:p>Diphenidine (<jats:bold>1a<\/jats:bold>), a dissociative anaesthetic, was first reported in 2013. Since then, a number of derivatives <jats:italic>e.g.<\/jats:italic> 2-methoxphenidine (<jats:bold>1b<\/jats:bold>) have been produced by clandestine laboratories and sold as <jats:italic>research chemicals<\/jats:italic>. Fluorinated diphenidines, namely, [1-(2,6-difluorophenyl)-2-phenylethyl]dimethylazanium chloride, C<jats:sub>16<\/jats:sub>H<jats:sub>18<\/jats:sub>F<jats:sub>2<\/jats:sub>N<jats:sup>+<\/jats:sup>\u00b7Cl<jats:sup>\u2212<\/jats:sup>, (<jats:bold>I<\/jats:bold>), [1-(2,6-difluorophenyl)-2-phenylethyl](ethyl)azanium chloride dichloromethane hemisolvate, 2C<jats:sub>16<\/jats:sub>H<jats:sub>18<\/jats:sub>F<jats:sub>2<\/jats:sub>N<jats:sup>+<\/jats:sup>\u00b72Cl<jats:sup>\u2212<\/jats:sup>\u00b7CH<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub>, (<jats:bold>II<\/jats:bold>), <jats:italic>tert<\/jats:italic>-butyl[1-(2,6-difluorophenyl)-2-phenylethyl]azanium chloride, C<jats:sub>18<\/jats:sub>H<jats:sub>22<\/jats:sub>F<jats:sub>2<\/jats:sub>N<jats:sup>+<\/jats:sup>\u00b7Cl<jats:sup>\u2212<\/jats:sup>, (<jats:bold>III<\/jats:bold>), 1-[1-(2,6-difluorophenyl)-2-phenylethyl]pyrrolidin-1-ium chloride, C<jats:sub>18<\/jats:sub>H<jats:sub>20<\/jats:sub>F<jats:sub>2<\/jats:sub>N<jats:sup>+<\/jats:sup>\u00b7Cl<jats:sup>\u2212<\/jats:sup>, (<jats:bold>IV<\/jats:bold>), and 1-[1-(2,3,4,5,6-pentafluorophenyl)-2-phenylethyl]piperidin-1-ium chloride, C<jats:sub>19<\/jats:sub>H<jats:sub>19<\/jats:sub>F<jats:sub>5<\/jats:sub>N<jats:sup>+<\/jats:sup>\u00b7Cl<jats:sup>\u2212<\/jats:sup>, (<jats:bold>V<\/jats:bold>), were synthesized and structurally characterized by <jats:sup>1<\/jats:sup>H, <jats:sup>13<\/jats:sup>C and <jats:sup>19<\/jats:sup>F NMR spectroscopy, and single-crystal X-ray diffraction. All five structures exhibit hydrogen bonding between the quaternary amine hydrogen atoms and the chlorine. The N\u2014H...Cl distances for (<jats:bold>II<\/jats:bold>) and (<jats:bold>III<\/jats:bold>) range from 2.21 to 2.31\u2005\u00c5, whereas (<jats:bold>I<\/jats:bold>), (<jats:bold>IV<\/jats:bold>) and (<jats:bold>V<\/jats:bold>) exhibit shorter N\u2014H...Cl distances (2.07\u20132.20\u2005\u00c5). Compounds (<jats:bold>IV<\/jats:bold>) and (<jats:bold>V<\/jats:bold>) include pyrrolidine and piperidine rings, respectively; the pyrrolidine ring adopts an envelope conformation whereas the piperidine ring adopts a chair conformation. The crystal packing in compounds (<jats:bold>I<\/jats:bold>)\u2013(<jats:bold>V<\/jats:bold>) is characterized by C\u2014H...\u03c0 interactions; no \u03c0\u2013\u03c0 interactions are observed.<\/jats:p>","DOI":"10.1107\/s2056989025001288","type":"journal-article","created":{"date-parts":[[2025,2,14]],"date-time":"2025-02-14T08:49:20Z","timestamp":1739522960000},"page":"229-234","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis and crystal structures of five fluorinated diphenidine derivatives"],"prefix":"10.1107","volume":"81","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3756-6505","authenticated-orcid":true,"given":"Ryan E.","family":"Mewis","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Matthew C.","family":"Hulme","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jack","family":"Marron","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Stuart K.","family":"Langley","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Oliver B.","family":"Sutcliffe","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sophie L.","family":"Benjamin","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2025,2,14]]},"reference":[{"key":"ee2011_bb1","unstructured":"Agilent (2014). 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