{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,6]],"date-time":"2026-05-06T23:53:27Z","timestamp":1778111607333,"version":"3.51.4"},"reference-count":21,"publisher":"International Union of Crystallography (IUCr)","issue":"7","license":[{"start":{"date-parts":[[2016,6,10]],"date-time":"2016-06-10T00:00:00Z","timestamp":1465516800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},{"start":{"date-parts":[[2016,6,10]],"date-time":"2016-06-10T00:00:00Z","timestamp":1465516800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/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"],"published-print":{"date-parts":[[2016,7,1]]},"abstract":"<jats:p>Three coumarin derivatives,<jats:italic>viz.<\/jats:italic>6-methyl-<jats:italic>N<\/jats:italic>-(3-methylphenyl)-2-oxo-2<jats:italic>H<\/jats:italic>-chromene-3-carboxamide, C<jats:sub>18<\/jats:sub>H<jats:sub>15<\/jats:sub>NO<jats:sub>3<\/jats:sub>(<jats:bold>1<\/jats:bold>),<jats:italic>N<\/jats:italic>-(3-methoxyphenyl)-6-methyl-2-oxo-2<jats:italic>H<\/jats:italic>-chromene-3-carboxamide, C<jats:sub>18<\/jats:sub>H<jats:sub>15<\/jats:sub>NO<jats:sub>4<\/jats:sub>(<jats:bold>2<\/jats:bold>), and 6-methoxy-<jats:italic>N<\/jats:italic>-(3-methoxyphenyl)-2-oxo-2<jats:italic>H<\/jats:italic>-chromene-3-carboxamide, C<jats:sub>18<\/jats:sub>H<jats:sub>15<\/jats:sub>NO<jats:sub>5<\/jats:sub>(<jats:bold>3<\/jats:bold>), were synthesized and structurally characterized. The molecules display intramolecular N\u2014H...O and weak C\u2014H...O hydrogen bonds, which probably contribute to the approximate planarity of the molecules. The supramolecular structures feature C\u2014H...O hydrogen bonds and \u03c0\u2013\u03c0 interactions, as confirmed by Hirshfeld surface analyses.<\/jats:p>","DOI":"10.1107\/s2056989016008665","type":"journal-article","created":{"date-parts":[[2016,6,10]],"date-time":"2016-06-10T08:45:06Z","timestamp":1465548306000},"page":"926-932","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":21,"title":["Crystal structures of three 6-substituted coumarin-3-carboxamide derivatives"],"prefix":"10.1107","volume":"72","author":[{"given":"L\u00edgia R.","family":"Gomes","sequence":"first","affiliation":[]},{"given":"John Nicolson","family":"Low","sequence":"additional","affiliation":[]},{"given":"Andr\u00e9","family":"Fonseca","sequence":"additional","affiliation":[]},{"given":"Maria Jo\u00e3o","family":"Matos","sequence":"additional","affiliation":[]},{"given":"Fernanda","family":"Borges","sequence":"additional","affiliation":[]}],"member":"329","published-online":{"date-parts":[[2016,6,10]]},"reference":[{"key":"hb7589_bb1","doi-asserted-by":"crossref","first-page":"4922","DOI":"10.1016\/j.bmcl.2010.06.048","volume":"20","author":"Chimenti","year":"2010","journal-title":"Bioorg. 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