{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T18:45:56Z","timestamp":1785437156623,"version":"3.56.0"},"reference-count":29,"publisher":"International Union of Crystallography (IUCr)","issue":"5","license":[{"start":{"date-parts":[[2023,4,14]],"date-time":"2023-04-14T00:00:00Z","timestamp":1681430400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2023,4,14]],"date-time":"2023-04-14T00:00:00Z","timestamp":1681430400000},"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":[[2023,4,7]]},"published-print":{"date-parts":[[2023,5,1]]},"abstract":"<jats:p>\n                    The syntheses and crystal structures of four salts of amitriptynol (C\n                    <jats:sub>20<\/jats:sub>\n                    H\n                    <jats:sub>25<\/jats:sub>\n                    NO) with different carboxylic acids are described. The salts formed directly from solutions of amitriptyline (which first hydrolysed to amitriptynol) and the corresponding acid in acetonitrile to form amitriptynolium [systematic name: (3-{2-hydroxytricyclo[9.4.0.0\n                    <jats:sup>3,8<\/jats:sup>\n                    ]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}propyl)dimethylazanium] 4-methoxybenzoate monohydrate, C\n                    <jats:sub>20<\/jats:sub>\n                    H\n                    <jats:sub>26<\/jats:sub>\n                    NO\n                    <jats:sup>+<\/jats:sup>\n                    \u00b7C\n                    <jats:sub>8<\/jats:sub>\n                    H\n                    <jats:sub>7<\/jats:sub>\n                    O\n                    <jats:sub>3<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    \u00b7H\n                    <jats:sub>2<\/jats:sub>\n                    O, (\n                    <jats:bold>I<\/jats:bold>\n                    ), amitriptynolium 3,4-dimethoxybenzoate trihydrate, C\n                    <jats:sub>20<\/jats:sub>\n                    H\n                    <jats:sub>26<\/jats:sub>\n                    NO\n                    <jats:sup>+<\/jats:sup>\n                    \u00b7C\n                    <jats:sub>9<\/jats:sub>\n                    H\n                    <jats:sub>9<\/jats:sub>\n                    O\n                    <jats:sub>4<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    \u00b73H\n                    <jats:sub>2<\/jats:sub>\n                    O, (\n                    <jats:bold>II<\/jats:bold>\n                    ), amitriptynolium 2-chlorobenzoate, C\n                    <jats:sub>20<\/jats:sub>\n                    H\n                    <jats:sub>26<\/jats:sub>\n                    NO\n                    <jats:sup>+<\/jats:sup>\n                    \u00b7C\n                    <jats:sub>7<\/jats:sub>\n                    H\n                    <jats:sub>4<\/jats:sub>\n                    ClO\n                    <jats:sub>2<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    , (\n                    <jats:bold>III<\/jats:bold>\n                    ), and amitriptynolium  thiophene-2-carboxylate monohydrate, C\n                    <jats:sub>20<\/jats:sub>\n                    H\n                    <jats:sub>26<\/jats:sub>\n                    NO\n                    <jats:sup>+<\/jats:sup>\n                    \u00b7C\n                    <jats:sub>5<\/jats:sub>\n                    H\n                    <jats:sub>3<\/jats:sub>\n                    O\n                    <jats:sub>2<\/jats:sub>\n                    S\n                    <jats:sup>\u2212<\/jats:sup>\n                    \u00b7H\n                    <jats:sub>2<\/jats:sub>\n                    O, (\n                    <jats:bold>IV<\/jats:bold>\n                    ). Compound (\n                    <jats:bold>III<\/jats:bold>\n                    ) crystallizes with two cations, two anions and six water molecules in the asymmetric unit. The different conformations of the amitriptynolium cations are determined by the torsion angles in the dimethylamino-propyl chains and the \u2013CH\n                    <jats:sub>2<\/jats:sub>\n                    \u2013CH\n                    <jats:sub>2<\/jats:sub>\n                    - bridge between the benzene rings in the tricyclic ring system, and are complicated by disorder of the bridging unit in\n                    <jats:bold>II<\/jats:bold>\n                    and\n                    <jats:bold>III<\/jats:bold>\n                    . The packing in all four salts is dominated by N\u2014H...O and O\u2014H...O hydrogen bonds. Hirshfeld surface analyses show that the amitriptynolium cations make similar inter-species contacts, despite the distinctly different packing in each salt.\n                  <\/jats:p>","DOI":"10.1107\/s2056989023003225","type":"journal-article","created":{"date-parts":[[2023,4,11]],"date-time":"2023-04-11T04:40:45Z","timestamp":1681188045000},"page":"451-457","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Syntheses, crystal structures and Hirshfeld surface analyses of four molecular salts of amitriptynol"],"prefix":"10.1107","volume":"79","author":[{"family":"Vinaya","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/012bxv356","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haleyur G.","family":"Anil Kumar","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thaluru M.","family":"Mohan Kumar","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Beliyaiah","family":"Lakshmana","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/012bxv356","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yeriyur B.","family":"Basavaraju","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/012bxv356","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9039-0273","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":[[2023,4,14]]},"reference":[{"key":"hb8061_bb1","doi-asserted-by":"crossref","first-page":"118899","DOI":"10.1016\/j.ijpharm.2019.118899","volume":"575","author":"Aree","year":"2020","journal-title":"Int. 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