{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T05:56:18Z","timestamp":1785477378273,"version":"3.56.0"},"reference-count":20,"publisher":"International Union of Crystallography (IUCr)","issue":"9","license":[{"start":{"date-parts":[[2022,8,8]],"date-time":"2022-08-08T00:00:00Z","timestamp":1659916800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2022,8,8]],"date-time":"2022-08-08T00:00:00Z","timestamp":1659916800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/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"],"accepted":{"date-parts":[[2022,8,2]]},"published-print":{"date-parts":[[2022,9,1]]},"abstract":"<jats:p>\n                    Two new 1,2,4-triazine-containing sulfonamide derivatives, namely, 4-bromo-\n                    <jats:italic>N<\/jats:italic>\n                    -(5,6-diphenyl-2\n                    <jats:italic>H<\/jats:italic>\n                    -1,2,4-triazin-3-ylidene)benzenesulfonamide, C\n                    <jats:sub>21<\/jats:sub>\n                    H\n                    <jats:sub>15<\/jats:sub>\n                    BrN\n                    <jats:sub>4<\/jats:sub>\n                    O\n                    <jats:sub>4<\/jats:sub>\n                    S,\n                    <jats:bold>3a<\/jats:bold>\n                    , and methyl 2-{[(5,6-diphenyl-1,2,4-triazin-3-yl)sulfamoyl]methyl}benzoate, C\n                    <jats:sub>24<\/jats:sub>\n                    H\n                    <jats:sub>20<\/jats:sub>\n                    N\n                    <jats:sub>4<\/jats:sub>\n                    O\n                    <jats:sub>4<\/jats:sub>\n                    S,\n                    <jats:bold>3b<\/jats:bold>\n                    , which crystallize in the different sulfonimide and sulfonamide tautomeric forms, respectively, were synthesized and characterized by spectroscopic, X-ray diffraction and theoretical calculation methods. Both molecules adopt a very similar conformation of the common part of the structure and the differences occur within the substituents on the sulfonamide group. The amino groups characteristic for the existing tautomeric forms are involved in strong intermolecular N\u2014H...N and N\u2014H...O hydrogen bonds in\n                    <jats:bold>3a<\/jats:bold>\n                    and\n                    <jats:bold>3b<\/jats:bold>\n                    , respectively. The Hirshfeld surface analysis showed that H...H contacts constitute a high percentage of the intermolecular interactions. Theoretical calculations at the\n                    <jats:italic>ab initio<\/jats:italic>\n                    DFT\/B3LYP\/6-311++G(d,p) level showed that the two tautomeric forms observed for\n                    <jats:bold>3a<\/jats:bold>\n                    and\n                    <jats:bold>3b<\/jats:bold>\n                    can co-exist in chloroform, ethanol and water solutions, with a distinct predominance of the sulfonamide form; the participation of the sulfonimide form increases with increasing solvent polarity.\n                  <\/jats:p>","DOI":"10.1107\/s2053229622007781","type":"journal-article","created":{"date-parts":[[2022,8,8]],"date-time":"2022-08-08T10:36:51Z","timestamp":1659955011000},"page":"462-469","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":3,"title":["Synthesis, structure and sulfonamide\u2013sulfonimide tautomerism of sulfonamide\u20131,2,4-triazine derivatives"],"prefix":"10.1107","volume":"78","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5317-0965","authenticated-orcid":true,"given":"Danuta","family":"Branowska","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3205-114X","authenticated-orcid":true,"given":"Waldemar","family":"Wysocki","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8487-261X","authenticated-orcid":true,"given":"Ewa","family":"Woli\u0144ska","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Karolina","family":"Koc","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Katarzyna","family":"Sta\u0144ska","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5765-4641","authenticated-orcid":true,"given":"Barbara","family":"Miros\u0142aw","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/015h0qg34","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zbigniew","family":"Karczmarzyk","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2022,8,8]]},"reference":[{"key":"ef3031_bb1","unstructured":"Agilent (2014). 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