{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T21:21:59Z","timestamp":1740172919512,"version":"3.37.3"},"reference-count":34,"publisher":"International Union of Crystallography (IUCr)","issue":"1","license":[{"start":{"date-parts":[[2022,1,1]],"date-time":"2022-01-01T00:00:00Z","timestamp":1640995200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2022,1,1]],"date-time":"2022-01-01T00:00:00Z","timestamp":1640995200000},"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"],"accepted":{"date-parts":[[2021,11,24]]},"published-print":{"date-parts":[[2022,1,1]]},"abstract":"<jats:p>The structures of novel cocrystals of 4-nitropyridine<jats:italic>N<\/jats:italic>-oxide with benzenesulfonamide derivatives, namely, 4-nitrobenzenesulfonamide\u20134-nitropyridine<jats:italic>N<\/jats:italic>-oxide (1\/1), C<jats:sub>5<\/jats:sub>H<jats:sub>4<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>3<\/jats:sub>\u00b7C<jats:sub>6<\/jats:sub>H<jats:sub>6<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>4<\/jats:sub>S, and 4-chlorobenzenesulfonamide\u20134-nitropyridine<jats:italic>N<\/jats:italic>-oxide (1\/1), C<jats:sub>6<\/jats:sub>H<jats:sub>6<\/jats:sub>ClNO<jats:sub>2<\/jats:sub>S\u00b7C<jats:sub>5<\/jats:sub>H<jats:sub>4<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>3<\/jats:sub>, are stabilized by N\u2014H...O hydrogen bonds, with the sulfonamide group acting as a proton donor. The O atoms of the<jats:italic>N<\/jats:italic>-oxide and nitro groups are acceptors in these interactions. The latter is a double acceptor of bifurcated hydrogen bonds. Previous studies on similar crystal structures indicated competition between these functional groups in the formation of hydrogen bonds, with the priority being for the<jats:italic>N<\/jats:italic>-oxide group. In contrast, the present X-ray studies indicate the existence of a hydrogen-bonding synthon including N\u2014H...O(<jats:italic>N<\/jats:italic>-oxide) and N\u2014H...O(nitro) bridges. We present here a more detailed analysis of the<jats:italic>N<\/jats:italic>-oxide\u2013sulfonamide\u2013nitro N\u2014H...O ternary complex with quantum theory computations and the Quantum Theory of Atoms in Molecules (QTAIM) approach. Both interactions are present in the crystals, but the O atom of the<jats:italic>N<\/jats:italic>-oxide group is found to be a more effective proton acceptor in hydrogen bonds, with an interaction energy about twice that of the nitro-group O atoms.<\/jats:p>","DOI":"10.1107\/s2053229621012511","type":"journal-article","created":{"date-parts":[[2021,12,7]],"date-time":"2021-12-07T08:58:21Z","timestamp":1638867501000},"page":"7-13","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":2,"title":["A novel hydrogen-bonding<i>N<\/i>-oxide\u2013sulfonamide\u2013nitro N\u2014H...O synthon determining the architecture of benzenesulfonamide cocrystals"],"prefix":"10.1107","volume":"78","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0498-1128","authenticated-orcid":true,"given":"Kinga","family":"Wzgarda-Raj","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Agnieszka J.","family":"Rybarczyk-Pirek","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5535-4525","authenticated-orcid":true,"given":"S\u0142awomir","family":"Wojtulewski","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0032-0878","authenticated-orcid":true,"given":"Marcin","family":"Palusiak","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2022,1,1]]},"reference":[{"key":"zo3015_bb1","doi-asserted-by":"crossref","first-page":"380","DOI":"10.1107\/S0108768110012048","volume":"66","author":"Allen","year":"2010","journal-title":"Acta Cryst. 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