{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T09:43:51Z","timestamp":1736847831023,"version":"3.33.0"},"reference-count":25,"publisher":"International Union of Crystallography (IUCr)","issue":"10","license":[{"start":{"date-parts":[[2019,9,10]],"date-time":"2019-09-10T00:00:00Z","timestamp":1568073600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2019,9,10]],"date-time":"2019-09-10T00:00:00Z","timestamp":1568073600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"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":[[2019,8,28]]},"published-print":{"date-parts":[[2019,10,1]]},"abstract":"<jats:p>The title compounds, 4-(5-acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl benzoate, C<jats:sub>20<\/jats:sub>H<jats:sub>19<\/jats:sub>N<jats:sub>3<\/jats:sub>O<jats:sub>4<\/jats:sub>S (<jats:bold>I<\/jats:bold>), 4-(5-acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl isobutyrate 0.25-hydrate, C<jats:sub>17<\/jats:sub>H<jats:sub>21<\/jats:sub>N<jats:sub>3<\/jats:sub>O<jats:sub>4<\/jats:sub>S\u00b70.25H<jats:sub>2<\/jats:sub>O (<jats:bold>II<\/jats:bold>), 4-(5-acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl propionate, C<jats:sub>16<\/jats:sub>H<jats:sub>19<\/jats:sub>N<jats:sub>3<\/jats:sub>O<jats:sub>4<\/jats:sub>S (<jats:bold>III<\/jats:bold>) and 4-(5-acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl cinnamate chloroform hemisolvate, C<jats:sub>22<\/jats:sub>H<jats:sub>21<\/jats:sub>N<jats:sub>3<\/jats:sub>O<jats:sub>4<\/jats:sub>S\u00b70.5CHCl<jats:sub>3<\/jats:sub> (<jats:bold>IV<\/jats:bold>), all crystallize with two independent molecules (<jats:italic>A<\/jats:italic> and <jats:italic>B<\/jats:italic>) in the asymmetric unit in the triclinic <jats:italic>P<\/jats:italic>\\overline{1} space group. Compound <jats:bold>II<\/jats:bold> crystallizes as a quaterhydrate, while compound <jats:bold>IV<\/jats:bold> crystallizes as a chloroform hemisolvate. In compounds <jats:bold>I<\/jats:bold>, <jats:bold>II<\/jats:bold>, <jats:bold>III<\/jats:bold> (molecules <jats:italic>A<\/jats:italic> and <jats:italic>B<\/jats:italic>) and <jats:bold>IV<\/jats:bold> (molecule <jats:italic>A<\/jats:italic>) the five-membered thiadiazole ring adopts an envelope conformation, with the tetrasubstituted C atom as the flap. In molecule <jats:italic>B<\/jats:italic> of <jats:bold>IV<\/jats:bold> this ring is flat (r.m.s. deviation 0.044\u2005\u00c5). The central benzene ring is in general almost normal to the mean plane of the thiadiazole ring in each molecule, with dihedral angles ranging from 75.8\u2005(1) to 85.5\u2005(2)\u00b0. In the crystals of all four compounds, the <jats:italic>A<\/jats:italic> and <jats:italic>B<\/jats:italic> molecules are linked <jats:italic>via<\/jats:italic> strong N\u2014H...O hydrogen bonds and generate centrosymmetric four-membered <jats:italic>R<\/jats:italic>\n                  <jats:sup>4<\/jats:sup>\n                  <jats:sub>4<\/jats:sub>(28) ring motifs. There are C\u2014H...O hydrogen bonds present in the crystals of all four compounds, and in <jats:bold>I<\/jats:bold> and <jats:bold>II<\/jats:bold> there are also C\u2014H...\u03c0 interactions present. The intermolecular contacts in the crystals of all four compounds were analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.<\/jats:p>","DOI":"10.1107\/s2056989019011915","type":"journal-article","created":{"date-parts":[[2019,9,10]],"date-time":"2019-09-10T09:20:46Z","timestamp":1568107246000},"page":"1436-1444","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["The crystal structures and Hirshfeld surface analyses of four 3,5-diacetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl derivatives"],"prefix":"10.1107","volume":"75","author":[{"given":"M.","family":"NizamMohideen","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"S.","family":"Syed Abuthahir","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"V.","family":"Viswanathan","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"D.","family":"Velmurugan","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"M.","family":"Karthik Ananth","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2019,9,10]]},"reference":[{"key":"su5508_bb1","doi-asserted-by":"crossref","first-page":"o2096","DOI":"10.1107\/S1600536808032108","volume":"64","author":"Aridoss","year":"2008","journal-title":"Acta Cryst. 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