{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,4]],"date-time":"2026-04-04T15:10:36Z","timestamp":1775315436388,"version":"3.50.1"},"reference-count":41,"publisher":"International Union of Crystallography (IUCr)","issue":"9","license":[{"start":{"date-parts":[[2016,8,26]],"date-time":"2016-08-26T00:00:00Z","timestamp":1472169600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2016,8,26]],"date-time":"2016-08-26T00:00:00Z","timestamp":1472169600000},"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":[[2016,9,1]]},"abstract":"<jats:p>A path to new synthons for application in crystal engineering is the replacement of a strong hydrogen-bond acceptor, like a C=O group, with a weaker acceptor, like a C=S group, in doubly or triply hydrogen-bonded synthons. For instance, if the C=O group at the 2-position of barbituric acid is changed into a C=S group, 2-thiobarbituric acid is obtained. Each of the compounds comprises two<jats:italic>ADA<\/jats:italic>hydrogen-bonding sites (<jats:italic>D<\/jats:italic>= donor and<jats:italic>A<\/jats:italic>= acceptor). We report the results of cocrystallization experiments of barbituric acid and 2-thiobarbituric acid, respectively, with 2,4-diaminopyrimidine, which contains a complementary<jats:italic>DAD<\/jats:italic>hydrogen-bonding site and is therefore capable of forming an<jats:italic>ADA<\/jats:italic>\/<jats:italic>DAD<\/jats:italic>synthon with barbituric acid and 2-thiobarbituric acid. In addition, pure 2,4-diaminopyrimidine was crystallized in order to study its preferred hydrogen-bonding motifs. The experiments yielded one ansolvate of 2,4-diaminopyrimidine (pyrimidine-2,4-diamine, DAPY), C<jats:sub>4<\/jats:sub>H<jats:sub>6<\/jats:sub>N<jats:sub>4<\/jats:sub>, (I), three solvates of DAPY, namely 2,4-diaminopyrimidine\u20131,4-dioxane (2\/1), 2C<jats:sub>4<\/jats:sub>H<jats:sub>6<\/jats:sub>N<jats:sub>4<\/jats:sub>\u00b7C<jats:sub>4<\/jats:sub>H<jats:sub>8<\/jats:sub>O<jats:sub>2<\/jats:sub>, (II), 2,4-diaminopyrimidine\u2013<jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>-dimethylacetamide (1\/1), C<jats:sub>4<\/jats:sub>H<jats:sub>6<\/jats:sub>N<jats:sub>4<\/jats:sub>\u00b7C<jats:sub>4<\/jats:sub>H<jats:sub>9<\/jats:sub>NO, (III), and 2,4-diaminopyrimidine\u20131-methylpyrrolidin-2-one (1\/1), C<jats:sub>4<\/jats:sub>H<jats:sub>6<\/jats:sub>N<jats:sub>4<\/jats:sub>\u00b7C<jats:sub>5<\/jats:sub>H<jats:sub>9<\/jats:sub>NO, (IV), one salt of barbituric acid,<jats:italic>viz<\/jats:italic>. 2,4-diaminopyrimidinium barbiturate (barbiturate is 2,4,6-trioxopyrimidin-5-ide), C<jats:sub>4<\/jats:sub>H<jats:sub>7<\/jats:sub>N<jats:sub>4<\/jats:sub><jats:sup>+<\/jats:sup>\u00b7C<jats:sub>4<\/jats:sub>H<jats:sub>3<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>3<\/jats:sub><jats:sup>\u2212<\/jats:sup>, (V), and two solvated salts of 2-thiobarbituric acid,<jats:italic>viz<\/jats:italic>. 2,4-diaminopyrimidinium 2-thiobarbiturate\u2013<jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>-dimethylformamide (1\/2) (2-thiobarbiturate is 4,6-dioxo-2-sulfanylidenepyrimidin-5-ide), C<jats:sub>4<\/jats:sub>H<jats:sub>7<\/jats:sub>N<jats:sub>4<\/jats:sub><jats:sup>+<\/jats:sup>\u00b7C<jats:sub>4<\/jats:sub>H<jats:sub>3<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>S<jats:sup>\u2212<\/jats:sup>\u00b72C<jats:sub>3<\/jats:sub>H<jats:sub>7<\/jats:sub>NO, (VI), and 2,4-diaminopyrimidinium 2-thiobarbiturate\u2013<jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>-dimethylacetamide (1\/2), C<jats:sub>4<\/jats:sub>H<jats:sub>7<\/jats:sub>N<jats:sub>4<\/jats:sub><jats:sup>+<\/jats:sup>\u00b7C<jats:sub>4<\/jats:sub>H<jats:sub>3<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>S<jats:sup>\u2212<\/jats:sup>\u00b72C<jats:sub>4<\/jats:sub>H<jats:sub>9<\/jats:sub>NO, (VII). The<jats:italic>ADA<\/jats:italic>\/<jats:italic>DAD<\/jats:italic>synthon was succesfully formed in the salt of barbituric acid,<jats:italic>i.e.<\/jats:italic>(V), as well as in the salts of 2-thiobarbituric acid,<jats:italic>i.e.<\/jats:italic>(VI) and (VII). In the crystal structures of 2,4-diaminopyrimidine,<jats:italic>i.e.<\/jats:italic>(I)\u2013(IV),<jats:italic>R<\/jats:italic><jats:sub>2<\/jats:sub><jats:sup>2<\/jats:sup>(8) N\u2014H...N hydrogen-bond motifs are preferred and, in two structures, additional<jats:italic>R<\/jats:italic><jats:sub>3<\/jats:sub><jats:sup>2<\/jats:sup>(8) patterns were observed.<\/jats:p>","DOI":"10.1107\/s205322961601336x","type":"journal-article","created":{"date-parts":[[2016,8,26]],"date-time":"2016-08-26T14:56:40Z","timestamp":1472223400000},"page":"705-715","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":5,"title":["One barbiturate and two solvated thiobarbiturates containing the triply hydrogen-bonded<i>ADA<\/i>\/<i>DAD<\/i>synthon, plus one ansolvate and three solvates of their coformer 2,4-diaminopyrimidine"],"prefix":"10.1107","volume":"72","author":[{"given":"Wilhelm Maximilian","family":"H\u00fctzler","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ernst","family":"Egert","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Michael","family":"Bolte","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2016,8,26]]},"reference":[{"key":"sk3636_bb1","doi-asserted-by":"crossref","first-page":"387","DOI":"10.1107\/S2052520615010872","volume":"71","author":"Aaker\u00f6y","year":"2015","journal-title":"Acta Cryst. 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