{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,1]],"date-time":"2025-11-01T07:40:38Z","timestamp":1761982838740,"version":"build-2065373602"},"reference-count":15,"publisher":"International Union of Crystallography (IUCr)","issue":"1","license":[{"start":{"date-parts":[[2015,1,1]],"date-time":"2015-01-01T00:00:00Z","timestamp":1420070400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},{"start":{"date-parts":[[2015,1,1]],"date-time":"2015-01-01T00:00:00Z","timestamp":1420070400000},"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":[[2015,1,1]]},"abstract":"<jats:p>Four<jats:italic>N<\/jats:italic>-(4-halophenyl)-4-oxo-4<jats:italic>H<\/jats:italic>-chromene-3-carboxamides (halo = F, Cl, Br and I),<jats:italic>N<\/jats:italic>-(4-fluorophenyl)-4-oxo-4<jats:italic>H<\/jats:italic>-chromene-3-carboxamide, C<jats:sub>16<\/jats:sub>H<jats:sub>10<\/jats:sub>FNO<jats:sub>3<\/jats:sub>,<jats:italic>N<\/jats:italic>-(4-chlorophenyl)-4-oxo-4<jats:italic>H<\/jats:italic>-chromene-3-carboxamide, C<jats:sub>16<\/jats:sub>H<jats:sub>10<\/jats:sub>ClNO<jats:sub>3<\/jats:sub>,<jats:italic>N<\/jats:italic>-(4-bromophenyl)-4-oxo-4<jats:italic>H<\/jats:italic>-chromene-3-carboxamide, C<jats:sub>16<\/jats:sub>H<jats:sub>10<\/jats:sub>BrNO<jats:sub>3<\/jats:sub>,<jats:italic>N<\/jats:italic>-(4-iodophenyl)-4-oxo-4<jats:italic>H<\/jats:italic>-chromene-3-carboxamide, C<jats:sub>16<\/jats:sub>H<jats:sub>10<\/jats:sub>INO<jats:sub>3<\/jats:sub>, have been structurally characterized. The molecules are essentially planar and each exhibits an<jats:italic>anti<\/jats:italic>conformation with respect to the C\u2014N rotamer of the amide and a<jats:italic>cis<\/jats:italic>geometry with respect to the relative positions of the C<jats:sub>arom<\/jats:sub>\u2014C<jats:sub>arom<\/jats:sub>bond of the chromone ring and the carbonyl group of the amide. The structures each exhibit an intramolecular hydrogen-bonding network comprising an N\u2014H...O hydrogen bond between the amide N atom and the O atom of the carbonyl group of the pyrone ring, forming an<jats:italic>S<\/jats:italic>(6) ring, and a weak C<jats:sub>arom<\/jats:sub>\u2014H...O interaction with the O atom of the carbonyl group of the amide as acceptor, which forms another<jats:italic>S<\/jats:italic>(6) ring. All four compounds have the same supramolecular structure, consisting of<jats:italic>R<\/jats:italic><jats:sub>2<\/jats:sub><jats:sup>2<\/jats:sup>(13) rings that are propagated along the<jats:italic>a-<\/jats:italic>axis direction by unit translation. There is \u03c0\u2013\u03c0 stacking involving inversion-related molecules in each structure.<\/jats:p>","DOI":"10.1107\/s2056989014027054","type":"journal-article","created":{"date-parts":[[2014,12,19]],"date-time":"2014-12-19T11:45:29Z","timestamp":1418989529000},"page":"88-93","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":8,"title":["The crystal structures of four<i>N<\/i>-(4-halophenyl)-4-oxo-4<i>H<\/i>-chromene-3-carboxamides"],"prefix":"10.1107","volume":"71","author":[{"given":"Ligia R.","family":"Gomes","sequence":"first","affiliation":[]},{"given":"John Nicolson","family":"Low","sequence":"additional","affiliation":[]},{"given":"Fernando","family":"Cagide","sequence":"additional","affiliation":[]},{"given":"Fernanda","family":"Borges","sequence":"additional","affiliation":[]}],"member":"329","published-online":{"date-parts":[[2015,1,1]]},"reference":[{"key":"lh5743_bb1","doi-asserted-by":"crossref","first-page":"6446","DOI":"10.1016\/j.tetlet.2011.09.095","volume":"52","author":"Cagide","year":"2011","journal-title":"Tetrahedron Lett."},{"key":"lh5743_bb2","doi-asserted-by":"crossref","first-page":"683","DOI":"10.1039\/C2SC00955B","volume":"3","author":"Coles","year":"2012","journal-title":"Chem. 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