{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T16:44:39Z","timestamp":1785429879828,"version":"3.56.0"},"reference-count":31,"publisher":"International Union of Crystallography (IUCr)","issue":"5","license":[{"start":{"date-parts":[[2024,4,26]],"date-time":"2024-04-26T00:00:00Z","timestamp":1714089600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2024,4,26]],"date-time":"2024-04-26T00:00:00Z","timestamp":1714089600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"name":"National Science Foundation, Major Research Instrumentation Program","award":["1625543"],"award-info":[{"award-number":["1625543"]}]},{"name":"Shippensburg University Summer Undergraduate Research Experience"},{"name":"Shippensburg University College of Arts and Sciences Faculty-Led Research Fund"},{"name":"Beres Student\/Faculty Research Endowment"}],"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":[[2024,4,17]]},"published-print":{"date-parts":[[2024,5,1]]},"abstract":"<jats:p>\n                    Two 2,4,6-trimethylaniline-based trifuloromethanesulfonate (trifluoromethanesulfonate) salts were synthesized and characterized by single-crystal X-ray diffraction.\n                    <jats:italic>N<\/jats:italic>\n                    ,2,4,6-Tetramethylanilinium trifluoromethanesulfonate, [C\n                    <jats:sub>10<\/jats:sub>\n                    H\n                    <jats:sub>14<\/jats:sub>\n                    NH\n                    <jats:sub>2<\/jats:sub>\n                    <jats:sup>+<\/jats:sup>\n                    ][CF\n                    <jats:sub>3<\/jats:sub>\n                    O\n                    <jats:sub>3<\/jats:sub>\n                    S\n                    <jats:sup>\u2212<\/jats:sup>\n                    ] (\n                    <jats:bold>1<\/jats:bold>\n                    ), was synthesized\n                    <jats:italic>via<\/jats:italic>\n                    methylation of 2,4,6-trimethylaniline.\n                    <jats:italic>N<\/jats:italic>\n                    -Isopropylidene-\n                    <jats:italic>N<\/jats:italic>\n                    ,2,4,6-tetramethylanilinium trifluoromethanesulfonate, [C\n                    <jats:sub>13<\/jats:sub>\n                    H\n                    <jats:sub>20<\/jats:sub>\n                    N\n                    <jats:sup>+<\/jats:sup>\n                    ][CF\n                    <jats:sub>3<\/jats:sub>\n                    O\n                    <jats:sub>3<\/jats:sub>\n                    S\n                    <jats:sup>\u2212<\/jats:sup>\n                    ] (\n                    <jats:bold>2<\/jats:bold>\n                    ), was synthesized in a two-step reaction where the imine,\n                    <jats:italic>N<\/jats:italic>\n                    -isopropylidene-2,4,6-trimethylaniline, was first prepared\n                    <jats:italic>via<\/jats:italic>\n                    a dehydration reaction to form the Schiff base, followed by methylation using methyl trifluoromethanesulfonate to form the iminium ion. In compound\n                    <jats:bold>1<\/jats:bold>\n                    , both hydrogen bonding and \u03c0\u2013\u03c0 interactions form the main intermolecular interactions. The primary interaction is a strong N\u2014H...O hydrogen bond with the oxygen atoms of the trifluoromethanesulfonate anions bonded to the hydrogen atoms of the ammonium nitrogen atom to generate a one-dimensional chain. The [C\n                    <jats:sub>10<\/jats:sub>\n                    H\n                    <jats:sub>14<\/jats:sub>\n                    NH\n                    <jats:sub>2<\/jats:sub>\n                    <jats:sup>+<\/jats:sup>\n                    ] cations form dimers where the benzene rings form a \u03c0\u2013\u03c0 interaction with a parallel-displaced geometry. The separation distance between the calculated centroids of the benzene rings is 3.9129\u2005(8)\u2005\u00c5, and the interplanar spacing and ring slippage between the dimers are 3.5156\u2005(5) and 1.718\u2005\u00c5, respectively. For\n                    <jats:bold>2<\/jats:bold>\n                    , the [C\n                    <jats:sub>13<\/jats:sub>\n                    H\n                    <jats:sub>20<\/jats:sub>\n                    N\n                    <jats:sup>+<\/jats:sup>\n                    ] cations also form dimers as in\n                    <jats:bold>1<\/jats:bold>\n                    , but with the benzene rings highly slipped. The distance between the calculated centroids of the benzene rings is 4.8937\u2005(8)\u2005\u00c5, and interplanar spacing and ring slippage are 3.3646\u2005(5) and 3.553\u2005\u00c5, respectively. The major intermolecular interactions in\n                    <jats:bold>2<\/jats:bold>\n                    are instead a series of weaker C\u2014H...O hydrogen bonds [C...O distances of 3.1723\u2005(17), 3.3789\u2005(18), and 3.3789\u2005(18)\u2005\u00c5], an interaction virtually absent in the structure of\n                    <jats:bold>1<\/jats:bold>\n                    . Fluorine atoms are not involved in strong directional interactions in either structure.\n                  <\/jats:p>","DOI":"10.1107\/s2056989024003438","type":"journal-article","created":{"date-parts":[[2024,4,23]],"date-time":"2024-04-23T09:44:37Z","timestamp":1713865477000},"page":"543-549","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis and crystal structures of\n                    <i>N<\/i>\n                    ,2,4,6-tetramethylanilinium trifluoromethanesulfonate and\n                    <i>N<\/i>\n                    -isopropylidene-\n                    <i>N<\/i>\n                    ,2,4,6-tetramethylanilinium trifluoromethanesulfonate"],"prefix":"10.1107","volume":"80","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7911-8559","authenticated-orcid":true,"given":"John W.","family":"Stewart","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/048arep70","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0001-3323-444X","authenticated-orcid":true,"given":"Elena M.","family":"Irons","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/048arep70","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Giovanna","family":"Osorio Abanto","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/048arep70","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3305-852X","authenticated-orcid":true,"given":"Matthias","family":"Zeller","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4831-2911","authenticated-orcid":true,"given":"Curtis M.","family":"Zaleski","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/048arep70","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniel P.","family":"Predecki","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/048arep70","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2024,4,26]]},"reference":[{"key":"ej2004_bb1","unstructured":"B\u00f6hme, H. & Viehe, H. G. (1976). Advances in Organic Chemistry: Methods and Results Vol. 9, Iminium Salts in Organic Chemistry, Part 2. edited by H. B\u00f6hme & H. G. Viehe, pp. 759-773. New York: John Wiley and Sons."},{"key":"ej2004_bb2","unstructured":"Bruker (2022). APEX4 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA."},{"key":"ej2004_bb3","doi-asserted-by":"crossref","first-page":"4336","DOI":"10.1021\/acs.joc.7b03134","volume":"83","author":"Castoldi","year":"2018","journal-title":"J. Org. Chem."},{"key":"ej2004_bb4","doi-asserted-by":"crossref","first-page":"4723","DOI":"10.1002\/chem.201700477","volume":"23","author":"Chen","year":"2017","journal-title":"Chem. Eur. J."},{"key":"ej2004_bb5","doi-asserted-by":"crossref","first-page":"o2376","DOI":"10.1107\/S1600536809034497","volume":"65","author":"Cui","year":"2009","journal-title":"Acta Cryst. E"},{"key":"ej2004_bb6","doi-asserted-by":"crossref","unstructured":"Desiraju, G. R. & Steiner, T. (2001). The Weak Hydrogen Bond In Structural Chemistry and Biology. Oxford University Press.","DOI":"10.1093\/acprof:oso\/9780198509707.001.0001"},{"key":"ej2004_bb7","doi-asserted-by":"crossref","first-page":"5416","DOI":"10.1021\/cr068388p","volume":"107","author":"Erkkil\u00e4","year":"2007","journal-title":"Chem. Rev."},{"key":"ej2004_bb8","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Cryst. B"},{"key":"ej2004_bb9","doi-asserted-by":"crossref","first-page":"1281","DOI":"10.1107\/S0021889811043202","volume":"44","author":"H\u00fcbschle","year":"2011","journal-title":"J. Appl. Cryst."},{"key":"ej2004_bb10","doi-asserted-by":"crossref","first-page":"575","DOI":"10.1524\/zksu.2007.2007.suppl_26.575","volume":"2007","author":"Ibberson","year":"2007","journal-title":"Z. Kristallogr. Suppl."},{"key":"ej2004_bb11","doi-asserted-by":"crossref","first-page":"o3263","DOI":"10.1107\/S1600536812044595","volume":"68","author":"Ikhile","year":"2012","journal-title":"Acta Cryst. E"},{"key":"ej2004_bb12","first-page":"305","volume":"17","author":"Kapoor","year":"2010","journal-title":"Indian J. Eng. Mat. Sci."},{"key":"ej2004_bb13","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1016\/j.jhazmat.2009.08.058","volume":"173","author":"Kapoor","year":"2010","journal-title":"J. Hazard. Mater."},{"key":"ej2004_bb14","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S1600576714022985","volume":"48","author":"Krause","year":"2015","journal-title":"J. Appl. Cryst."},{"key":"ej2004_bb15","doi-asserted-by":"crossref","first-page":"2481","DOI":"10.1021\/acs.organomet.8b00290","volume":"37","author":"Kreml\u00e1\u010dek","year":"2018","journal-title":"Organometallics"},{"key":"ej2004_bb16","doi-asserted-by":"crossref","first-page":"699","DOI":"10.1002\/ejoc.201101336","author":"Latham","year":"2012","journal-title":"Eur. J. Org. Chem."},{"key":"ej2004_bb17","doi-asserted-by":"crossref","first-page":"489","DOI":"10.1021\/cr60225a003","volume":"63","author":"Layer","year":"1963","journal-title":"Chem. Rev."},{"key":"ej2004_bb18","doi-asserted-by":"crossref","first-page":"o929","DOI":"10.1107\/S160053680700253X","volume":"63","author":"Lemmerer","year":"2007","journal-title":"Acta Cryst. E"},{"key":"ej2004_bb19","doi-asserted-by":"crossref","first-page":"109339","DOI":"10.1016\/j.inoche.2022.109339","volume":"139","author":"Li","year":"2022","journal-title":"Inorg. Chem. Commun."},{"key":"ej2004_bb20","doi-asserted-by":"crossref","first-page":"o3080","DOI":"10.1107\/S1600536807025718","volume":"63","author":"Long","year":"2007","journal-title":"Acta Cryst. E"},{"key":"ej2004_bb21","doi-asserted-by":"crossref","first-page":"465","DOI":"10.1021\/sc400475r","volume":"2","author":"L\u00fc","year":"2014","journal-title":"ACS Sustainable Chem. Eng."},{"key":"ej2004_bb22","doi-asserted-by":"crossref","first-page":"226","DOI":"10.1107\/S1600576719014092","volume":"53","author":"Macrae","year":"2020","journal-title":"J. Appl. Cryst."},{"key":"ej2004_bb23","doi-asserted-by":"crossref","first-page":"o2729","DOI":"10.1107\/S1600536811038086","volume":"67","author":"Rong","year":"2011","journal-title":"Acta Cryst. E"},{"key":"ej2004_bb24","doi-asserted-by":"crossref","first-page":"477","DOI":"10.1002\/asia.200600380","volume":"2","author":"Sakakura","year":"2007","journal-title":"Chem. Asian J."},{"key":"ej2004_bb25","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"ej2004_bb26","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"ej2004_bb27","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1107\/S2056989019016244","volume":"76","author":"Spek","year":"2020","journal-title":"Acta Cryst. E"},{"key":"ej2004_bb28","unstructured":"Travis, A. S. (2007). The Chemistry of Anilines, Part 1, edited by Z. Rappoport, pp. 1-73. Chichester: John Wiley and Sons."},{"key":"ej2004_bb29","doi-asserted-by":"crossref","first-page":"675","DOI":"10.1246\/bcsj.46.675","volume":"46","author":"Tsuchimoto","year":"1973","journal-title":"Bull. Chem. Soc. Jpn"},{"key":"ej2004_bb30","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1107\/S0021889810022120","volume":"43","author":"Westrip","year":"2010","journal-title":"J. Appl. Cryst."},{"key":"ej2004_bb31","doi-asserted-by":"crossref","first-page":"9841","DOI":"10.1039\/c2jm30581j","volume":"22","author":"Zhang","year":"2012","journal-title":"J. Mater. Chem."}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2024\/05\/00\/ej2004\/ej2004.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2024\/05\/00\/ej2004\/ej2004.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T06:32:46Z","timestamp":1736749966000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989024003438"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,4,26]]},"references-count":31,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2024,5]]}},"alternative-id":["S2056989024003438"],"URL":"https:\/\/doi.org\/10.1107\/s2056989024003438","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989024003438\/ej2004sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989024003438\/ej20041sup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989024003438\/ej20042sup3.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989024003438\/ej20041sup4.cml","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989024003438\/ej20042sup5.cml","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"value":"2056-9890","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,4,26]]},"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?ej2004","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":"19 February 2024","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"17 April 2024","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"26 April 2024","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?ej2004"}},{"value":"\u00a9 2024 Stewart\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"}}]}}