{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T14:12:23Z","timestamp":1785420743618,"version":"3.56.0"},"reference-count":30,"publisher":"International Union of Crystallography (IUCr)","issue":"10","license":[{"start":{"date-parts":[[2024,9,24]],"date-time":"2024-09-24T00:00:00Z","timestamp":1727136000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2024,9,24]],"date-time":"2024-09-24T00:00:00Z","timestamp":1727136000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/501100002923","name":"Consejo Nacional de Investigaciones Cient\u00edficas y T\u00e9cnicas","doi-asserted-by":"crossref","award":["PIP 2021-0765"],"award-info":[{"award-number":["PIP 2021-0765"]}],"id":[{"id":"10.13039\/501100002923","id-type":"DOI","asserted-by":"crossref"}]},{"DOI":"10.13039\/501100003074","name":"Agencia Nacional de Promoci\u00f3n Cient\u00edfica y Tecnol\u00f3gica","doi-asserted-by":"crossref","award":["PICT 2022-03-0139"],"award-info":[{"award-number":["PICT 2022-03-0139"]}],"id":[{"id":"10.13039\/501100003074","id-type":"DOI","asserted-by":"crossref"}]}],"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":[[2024,9,19]]},"published-print":{"date-parts":[[2024,10,1]]},"abstract":"<jats:p>\n                    The molecular salt sulfamethoxazolium {or 4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]anilinium methyl sulfate monohydrate}, C\n                    <jats:sub>10<\/jats:sub>\n                    H\n                    <jats:sub>12<\/jats:sub>\n                    N\n                    <jats:sub>3<\/jats:sub>\n                    O\n                    <jats:sub>3<\/jats:sub>\n                    S\n                    <jats:sup>+<\/jats:sup>\n                    \u00b7CH\n                    <jats:sub>3<\/jats:sub>\n                    O\n                    <jats:sub>4<\/jats:sub>\n                    S\n                    <jats:sup>\u2212<\/jats:sup>\n                    \u00b7H\n                    <jats:sub>2<\/jats:sub>\n                    O, was prepared by the reaction of sulfamethoxazole and H\n                    <jats:sub>2<\/jats:sub>\n                    SO\n                    <jats:sub>4<\/jats:sub>\n                    in methanol and crystallized from methanol\u2013ether\u2013water. Protonation takes place at the nitrogen atom of the primary amino group. In the crystal, N\u2014H...O hydrogen bonds (water and methylsulfate anion) and intermolecular N\u2014H...N interactions involving the sulfonamide and isoxazole nitrogen atoms, link the components into a tri-dimensional network, additional cohesion being provided by face-to-face \u03c0\u2013\u03c0 interactions between the phenyl rings of adjacent molecules. A Hirshfeld surface analysis was used to verify the contributions of the different intermolecular interactions, showing that the three most important contributions for the crystal packing are from H...O (54.1%), H...H (29.2%) and H...N (5.0%) interactions.\n                  <\/jats:p>","DOI":"10.1107\/s2056989024009204","type":"journal-article","created":{"date-parts":[[2024,9,23]],"date-time":"2024-09-23T03:16:37Z","timestamp":1727061397000},"page":"1064-1068","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":2,"title":["Synthesis, crystal structure and Hirshfeld surface analysis of sulfamethoxazolium methylsulfate monohydrate"],"prefix":"10.1107","volume":"80","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0351-478X","authenticated-orcid":true,"given":"Aldana B.","family":"Moroni","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/02tphfq59","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tiago","family":"Bottoso","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/02tphfq59","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7270-8540","authenticated-orcid":true,"given":"Diego F.","family":"Lionello","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7124-2507","authenticated-orcid":true,"given":"Daniel R.","family":"Vega","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3173-2178","authenticated-orcid":true,"given":"Teodoro S.","family":"Kaufman","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/02tphfq59","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1099-3686","authenticated-orcid":true,"given":"Natalia L.","family":"Calvo","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/02tphfq59","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2024,9,24]]},"reference":[{"key":"ex2088_bb1","doi-asserted-by":"crossref","first-page":"3902","DOI":"10.1021\/acs.cgd.8b00216","volume":"18","author":"Alsubaie","year":"2018","journal-title":"Cryst. Growth Des."},{"key":"ex2088_bb2","doi-asserted-by":"crossref","first-page":"431","DOI":"10.3109\/03639048809151875","volume":"14","author":"Bettinetti","year":"1988","journal-title":"Drug Dev. Ind. Pharm."},{"key":"ex2088_bb3","unstructured":"Bruker (2019). APEX4 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA."},{"key":"ex2088_bb4","unstructured":"Cason, C. J. (2004). POV-RAY for Windows. Persistence of Vision, Raytracer Pty Ltd, Victoria, Australia. http:\/\/www. povray. org"},{"key":"ex2088_bb5","doi-asserted-by":"crossref","first-page":"2514","DOI":"10.2174\/092986709788682038","volume":"16","author":"Cushion","year":"2009","journal-title":"Curr. Med. Chem."},{"key":"ex2088_bb6","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1107\/S0021889812029111","volume":"45","author":"Farrugia","year":"2012","journal-title":"J. Appl. Cryst."},{"key":"ex2088_bb7","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Cryst. B"},{"key":"ex2088_bb8","doi-asserted-by":"crossref","first-page":"6559","DOI":"10.1039\/D0CE00924E","volume":"22","author":"Guti\u00e9rrez","year":"2020","journal-title":"CrystEngComm"},{"key":"ex2088_bb9","doi-asserted-by":"crossref","first-page":"130903","DOI":"10.1016\/j.molstruc.2021.130903","volume":"1244","author":"Habila","year":"2021","journal-title":"J. Mol. Struct."},{"key":"ex2088_bb10","doi-asserted-by":"crossref","first-page":"5525","DOI":"10.1021\/ja00170a016","volume":"112","author":"Hunter","year":"1990","journal-title":"J. Am. Chem. Soc."},{"key":"ex2088_bb11","doi-asserted-by":"crossref","first-page":"3885","DOI":"10.1039\/b003010o","author":"Janiak","year":"2000","journal-title":"J. Chem. Soc. Dalton Trans."},{"key":"ex2088_bb12","doi-asserted-by":"crossref","first-page":"586","DOI":"10.4269\/ajtmh.2003.68.586","volume":"68","author":"Khalil","year":"2003","journal-title":"Am. J. Trop. Med. Hyg."},{"key":"ex2088_bb13","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S1600576714022985","volume":"48","author":"Krause","year":"2015","journal-title":"J. Appl. Cryst."},{"key":"ex2088_bb14","doi-asserted-by":"crossref","first-page":"226","DOI":"10.1107\/S1600576719014092","volume":"53","author":"Macrae","year":"2020","journal-title":"J. Appl. Cryst."},{"key":"ex2088_bb15","doi-asserted-by":"crossref","first-page":"618","DOI":"10.1107\/S2056989015008701","volume":"71","author":"Malathy","year":"2015","journal-title":"Acta Cryst. E"},{"key":"ex2088_bb16","doi-asserted-by":"crossref","first-page":"e56916","DOI":"10.1371\/journal.pone.0056916","volume":"8","author":"Manyando","year":"2013","journal-title":"PLoS One"},{"key":"ex2088_bb17","doi-asserted-by":"crossref","first-page":"3814","DOI":"10.1039\/b704980c","author":"McKinnon","year":"2007","journal-title":"Chem. Commun."},{"key":"ex2088_bb18","doi-asserted-by":"crossref","first-page":"10250","DOI":"10.1039\/C9NJ00586B","volume":"43","author":"Moura Oliveira","year":"2019","journal-title":"New J. Chem."},{"key":"ex2088_bb19","doi-asserted-by":"crossref","unstructured":"Papich, M. G. (2021). Neostigmine. In Papich Handbook of Veterinary Drugs, 5th ed., pp. 648-650. Amsterdam: Elsevier.","DOI":"10.1016\/B978-0-323-70957-6.00377-0"},{"key":"ex2088_bb20","doi-asserted-by":"crossref","first-page":"5512","DOI":"10.1021\/ja042561m","volume":"127","author":"Price","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ex2088_bb21","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Cryst. A"},{"key":"ex2088_bb22","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"ex2088_bb23","doi-asserted-by":"crossref","first-page":"378","DOI":"10.1039\/B203191B","volume":"4","author":"Spackman","year":"2002","journal-title":"CrystEngComm"},{"key":"ex2088_bb24","doi-asserted-by":"crossref","first-page":"1006","DOI":"10.1107\/S1600576721002910","volume":"54","author":"Spackman","year":"2021","journal-title":"J. Appl. Cryst."},{"key":"ex2088_bb25","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1107\/S2056989019016244","volume":"76","author":"Spek","year":"2020","journal-title":"Acta Cryst. E"},{"key":"ex2088_bb26","doi-asserted-by":"crossref","first-page":"o4312","DOI":"10.1107\/S1600536807049446","volume":"63","author":"Subashini","year":"2007","journal-title":"Acta Cryst. E"},{"key":"ex2088_bb27","doi-asserted-by":"crossref","first-page":"m250","DOI":"10.1107\/S1600536807067190","volume":"64","author":"Subashini","year":"2008","journal-title":"Acta Cryst. E"},{"key":"ex2088_bb28","doi-asserted-by":"crossref","first-page":"197","DOI":"10.1016\/S0924-2031(01)00089-3","volume":"25","author":"Takasuka","year":"2001","journal-title":"Vib. Spectrosc."},{"key":"ex2088_bb29","first-page":"590","volume":"21","author":"Thompson","year":"1987","journal-title":"Drug Intell. Clin. Pharm."},{"key":"ex2088_bb30","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1107\/S0021889810022120","volume":"43","author":"Westrip","year":"2010","journal-title":"J. Appl. Cryst."}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2024\/10\/00\/ex2088\/ex2088.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2024\/10\/00\/ex2088\/ex2088.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,10,9]],"date-time":"2024-10-09T01:02:44Z","timestamp":1728435764000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989024009204"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,9,24]]},"references-count":30,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2024,10]]}},"alternative-id":["S2056989024009204"],"URL":"https:\/\/doi.org\/10.1107\/s2056989024009204","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989024009204\/ex2088sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989024009204\/ex2088Isup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989024009204\/ex2088Isup3.cml","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"value":"2056-9890","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,9,24]]},"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?ex2088","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":"1 September 2024","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"19 September 2024","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"24 September 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?ex2088"}},{"value":"\u00a9 2024 Moroni\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"}}]}}