{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,30]],"date-time":"2026-04-30T14:38:05Z","timestamp":1777559885158,"version":"3.51.4"},"reference-count":0,"publisher":"International Union of Crystallography (IUCr)","issue":"9","license":[{"start":{"date-parts":[[2014,8,27]],"date-time":"2014-08-27T00:00:00Z","timestamp":1409097600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2014,8,27]],"date-time":"2014-08-27T00:00:00Z","timestamp":1409097600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr C Struct Chem","Acta Crystallogr C","Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst C Struct Chem","Acta Cryst Sect C","Acta Cryst Sect C Struct Chem","Acta Crystallogr Sect C","Acta Crystallogr Sect C Struct Chem","Acta Crystallogr Sect C Cryst Struct Commun"],"published-print":{"date-parts":[[2014,9,1]]},"abstract":"<jats:p>Proton transfer to the sulfa drug sulfadiazine [systematic name: 4-amino-<jats:italic>N<\/jats:italic>-(pyrimidin-2-yl)benzenesulfonamide] gave eight salt forms. These are the monohydrate and methanol hemisolvate forms of the chloride (2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium chloride monohydrate, C<jats:sub>10<\/jats:sub>H<jats:sub>11<\/jats:sub>N<jats:sub>4<\/jats:sub>O<jats:sub>2<\/jats:sub>S<jats:sup>+<\/jats:sup>\u00b7Cl<jats:sup>\u2212<\/jats:sup>\u00b7H<jats:sub>2<\/jats:sub>O, (I), and 2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium chloride methanol hemisolvate, C<jats:sub>10<\/jats:sub>H<jats:sub>11<\/jats:sub>N<jats:sub>4<\/jats:sub>O<jats:sub>2<\/jats:sub>S<jats:sup>+<\/jats:sup>\u00b7Cl<jats:sup>\u2212<\/jats:sup>\u00b70.5CH<jats:sub>3<\/jats:sub>OH, (II)); a bromide monohydrate (2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium bromide monohydrate, C<jats:sub>10<\/jats:sub>H<jats:sub>11<\/jats:sub>N<jats:sub>4<\/jats:sub>O<jats:sub>2<\/jats:sub>S<jats:sup>+<\/jats:sup>\u00b7Br<jats:sup>\u2212<\/jats:sup>\u00b7H<jats:sub>2<\/jats:sub>O, (III)), which has a disordered water channel; a species containing the unusual tetraiodide dianion [bis(2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium) tetraiodide, 2C<jats:sub>10<\/jats:sub>H<jats:sub>11<\/jats:sub>N<jats:sub>4<\/jats:sub>O<jats:sub>2<\/jats:sub>S<jats:sup>+<\/jats:sup>\u00b7I<jats:sub>4<\/jats:sub><jats:sup>2\u2212<\/jats:sup>, (IV)], where the [I<jats:sub>4<\/jats:sub>]<jats:sup>2\u2212<\/jats:sup>ion is located at a crystallographic inversion centre; a tetrafluoroborate monohydrate (2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium tetrafluoroborate monohydrate, C<jats:sub>10<\/jats:sub>H<jats:sub>11<\/jats:sub>N<jats:sub>4<\/jats:sub>O<jats:sub>2<\/jats:sub>S<jats:sup>+<\/jats:sup>\u00b7BF<jats:sub>4<\/jats:sub><jats:sup>\u2212<\/jats:sup>\u00b7H<jats:sub>2<\/jats:sub>O, (V)); a nitrate (2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium nitrate, C<jats:sub>10<\/jats:sub>H<jats:sub>11<\/jats:sub>N<jats:sub>4<\/jats:sub>O<jats:sub>2<\/jats:sub>S<jats:sup>+<\/jats:sup>\u00b7NO<jats:sub>3<\/jats:sub><jats:sup>\u2212<\/jats:sup>, (VI)); an ethanesulfonate {4-[(pyrimidin-2-yl)sulfamoyl]anilinium ethanesulfonate, C<jats:sub>10<\/jats:sub>H<jats:sub>11<\/jats:sub>N<jats:sub>4<\/jats:sub>O<jats:sub>2<\/jats:sub>S<jats:sup>+<\/jats:sup>\u00b7C<jats:sub>2<\/jats:sub>H<jats:sub>5<\/jats:sub>SO<jats:sub>3<\/jats:sub><jats:sup>\u2212<\/jats:sup>, (VII)}; and a dihydrate of the 4-hydroxybenzenesulfonate {4-[(pyrimidin-2-yl)sulfamoyl]anilinium 4-hydroxybenzenesulfonate dihydrate, C<jats:sub>10<\/jats:sub>H<jats:sub>11<\/jats:sub>N<jats:sub>4<\/jats:sub>O<jats:sub>2<\/jats:sub>S<jats:sup>+<\/jats:sup>\u00b7HOC<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>SO<jats:sub>3<\/jats:sub><jats:sup>\u2212<\/jats:sup>\u00b72H<jats:sub>2<\/jats:sub>O, (VIII)}. All these structures feature alternate layers of cations and of anions where any solvent is associated with the anion layers. The two sulfonate salts are protonated at the aniline N atom and the amide N atom of sulfadiazine, a tautomeric form of the sulfadiazine cation that has not been crystallographically described before. All the other salt forms are instead protonated at the aniline group and on one N atom of the pyrimidine ring. Whilst all eight species are based upon hydrogen-bonded centrosymetric dimers with graph set<jats:italic>R<\/jats:italic><jats:sub>2<\/jats:sub><jats:sup>2<\/jats:sup>(8), the two sulfonate structures also differ in that these dimers do not link into one-dimensional chains of cations through NH<jats:sub>3<\/jats:sub>-to-SO<jats:sub>2<\/jats:sub>hydrogen-bonding interactions, whilst the other six species do. The chloride methanol hemisolvate and the tetraiodide are isostructural and a packing analysis of the cation positions shows that the chloride monohydrate structure is also closely related to these.<\/jats:p>","DOI":"10.1107\/s2053229614018725","type":"journal-article","created":{"date-parts":[[2014,10,30]],"date-time":"2014-10-30T13:23:53Z","timestamp":1414675433000},"page":"900-907","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":7,"title":["Eight salt forms of sulfadiazine"],"prefix":"10.1107","volume":"70","author":[{"given":"Amanda R.","family":"Buist","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lynn","family":"Dennany","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alan R.","family":"Kennedy","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Craig","family":"Manzie","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Katherine","family":"McPhie","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Brandon","family":"Walker","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2014,8,27]]},"container-title":["Acta Crystallographica Section C Structural Chemistry"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/c\/issues\/2014\/09\/00\/lg3144\/lg3144.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/c\/issues\/2014\/09\/00\/lg3144\/lg3144.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T09:59:07Z","timestamp":1736762347000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2053229614018725"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,8,27]]},"references-count":0,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2014,9]]}},"alternative-id":["S2053229614018725"],"URL":"https:\/\/doi.org\/10.1107\/s2053229614018725","relation":{},"ISSN":["2053-2296"],"issn-type":[{"value":"2053-2296","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,8,27]]},"assertion":[{"value":"Acta Crystallographica Section C: Structural Chemistry","name":"journal","label":"Journal","explanation":{"URL":"http:\/\/journals.iucr.org\/c"}},{"value":"research papers","name":"content_type","label":"Content type","explanation":{"URL":"http:\/\/journals.iucr.org\/c\/issues\/2011\/01\/00\/me0438\/index.html"}},{"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":"4 August 2014","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"18 August 2014","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"27 August 2014","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":"http:\/\/scripts.iucr.org\/cgi-bin\/sendsup?lg3144"}},{"value":"\u00a9 2014 International Union of Crystallography","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},"group":{"name":"copyright_and_licensing","label":"Copyright and licencing"}}]}}