{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T21:49:08Z","timestamp":1740174548450,"version":"3.37.3"},"reference-count":24,"publisher":"International Union of Crystallography (IUCr)","issue":"5","license":[{"start":{"date-parts":[[2020,4,30]],"date-time":"2020-04-30T00:00:00Z","timestamp":1588204800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2020,4,30]],"date-time":"2020-04-30T00:00:00Z","timestamp":1588204800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/100007226","name":"Villanova University","doi-asserted-by":"crossref","id":[{"id":"10.13039\/100007226","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":[[2020,1,29]]},"published-print":{"date-parts":[[2020,5,1]]},"abstract":"<jats:p>The pyranopyran amide (2<jats:italic>S<\/jats:italic>,4a<jats:italic>R<\/jats:italic>,8a<jats:italic>R<\/jats:italic>)-6-oxo-2,4a,6,8a-tetrahydropyrano[3,2-<jats:italic>b<\/jats:italic>]pyran-2-carboxamide, C<jats:sub>9<\/jats:sub>H<jats:sub>9<\/jats:sub>NO<jats:sub>4<\/jats:sub>, <jats:bold>3<\/jats:bold>, was prepared by a chemoselective hydration of the corresponding nitrile, <jats:bold>2<\/jats:bold>, using a heterogeneous catalytic method based on copper(II) supported on molecular sieves, in the presence of acetaldoxime. Compound <jats:bold>3<\/jats:bold> belongs to a new class of pyranopyrans that possess antibacterial and phytotoxic activity. Crystallographic analysis of <jats:bold>3<\/jats:bold> shows a bent structure for the <jats:italic>cis<\/jats:italic>-fused bicyclic pyranopyran, similar to nitrile <jats:bold>2<\/jats:bold>. Evidence of an intramolecular hydrogen bond involving the amide group and ring oxygen was not observed; however, two separate intermolecular hydrogen-bonding interactions were observed between the amide hydrogen atoms and adjacent carbonyl oxygen atoms along the <jats:italic>b<\/jats:italic>- and <jats:italic>a<\/jats:italic>-axis directions. The latter interaction may also be supported by an intermolecular C\u2014H...O hydrogen bond. The lattice is filled out by close-packed layers of this hydrogen-bonded network along the <jats:italic>c-<\/jats:italic>axis direction, related from one to the next by a 2<jats:sub>1<\/jats:sub> screw axis.<\/jats:p>","DOI":"10.1107\/s2056989020001292","type":"journal-article","created":{"date-parts":[[2020,4,30]],"date-time":"2020-04-30T10:32:21Z","timestamp":1588242741000},"page":"761-764","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["Synthesis and crystal structure of (2<i>S<\/i>,4a<i>R<\/i>,8a<i>R<\/i>)-6-oxo-2,4a,6,8a-tetrahydropyrano[3,2-<i>b<\/i>]pyran-2-carboxamide"],"prefix":"10.1107","volume":"76","author":[{"given":"John","family":"Greene","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Noa","family":"Kopplin","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jack","family":"Roireau","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mark","family":"Bezpalko","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Scott","family":"Kassel","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Michael W.","family":"Giuliano","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Robert","family":"Giuliano","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2020,4,30]]},"reference":[{"key":"zl4038_bb1","first-page":"435","volume":"27","author":"Altomare","year":"1994","journal-title":"Appl. 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