{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T21:49:10Z","timestamp":1740174550696,"version":"3.37.3"},"reference-count":21,"publisher":"International Union of Crystallography (IUCr)","issue":"7","license":[{"start":{"date-parts":[[2020,6,19]],"date-time":"2020-06-19T00:00:00Z","timestamp":1592524800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2020,6,19]],"date-time":"2020-06-19T00:00:00Z","timestamp":1592524800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"name":"Swiss National Science Foundation and the University of Neuch\u00e2tel"}],"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":[[2020,6,14]]},"published-print":{"date-parts":[[2020,7,1]]},"abstract":"<jats:p>In the molecule of 6,8-dimethoxy-3-methyl-1<jats:italic>H<\/jats:italic>-isochromen-1-one, C<jats:sub>12<\/jats:sub>H<jats:sub>12<\/jats:sub>O<jats:sub>4<\/jats:sub>, (<jats:bold>I<\/jats:bold>), the two methoxy groups are directed <jats:italic>anti<\/jats:italic> with respect to each other. In the molecule of the brominated derivative, 5-bromo-6,8-dimethoxy-3-methyl-1<jats:italic>H<\/jats:italic>-isochromen-1-one, that crystallized as a chloroform monosolvate, C<jats:sub>12<\/jats:sub>H<jats:sub>11<\/jats:sub>BrO<jats:sub>4<\/jats:sub>\u00b7CHCl<jats:sub>3<\/jats:sub>, (<jats:bold>II\u00b7CHCl<jats:sub>3<\/jats:sub>\n                  <\/jats:bold>), the methoxy groups are directed <jats:italic>syn<\/jats:italic> to each other. In the crystal of <jats:bold>I<\/jats:bold>, molecules are linked by bifurcated C\u2014H...O hydrogen bonds, forming chains along the <jats:italic>c<\/jats:italic>-axis direction. The chains are linked by C\u2014H...\u03c0 interactions, forming a supramolecular framework. In the crystal of <jats:bold>II\u00b7CHCl<jats:sub>3<\/jats:sub>\n                  <\/jats:bold>, molecules are linked by C\u2014H...O hydrogen bonds forming 2<jats:sub>1<\/jats:sub> helices parallel to the <jats:italic>b<\/jats:italic>-axis direction. The chloroform solvate molecules are linked to the helices by C\u2014H...O(carbonyl) hydrogen bonds. The helices stack up the <jats:italic>c<\/jats:italic>-axis direction and are linked by offset \u03c0\u2013\u03c0 interactions [intercentroid distance = 3.517\u2005(3)\u2005\u00c5], forming layers parallel to the (100) plane. Compound <jats:bold>II\u00b7CHCl<jats:sub>3<\/jats:sub>\n                  <\/jats:bold> was refined as a two-component twin. Two chlorine atoms of the chloroform solvate are disordered over two positions and were refined with a fixed occupancy ratio of 0.5:0.5.<\/jats:p>","DOI":"10.1107\/s2056989020007975","type":"journal-article","created":{"date-parts":[[2020,6,19]],"date-time":"2020-06-19T08:28:27Z","timestamp":1592555307000},"page":"1107-1112","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Crystal structures and Hirshfeld surface analyses of 6,8-dimethoxy-3-methyl-1<i>H<\/i>-isochromen-1-one and 5-bromo-6,8-dimethoxy-3-methyl-1<i>H<\/i>-isochromen-1-one chloroform monosolvate"],"prefix":"10.1107","volume":"76","author":[{"given":"Mustapha","family":"Tiouabi","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rapha\u00ebl","family":"Tabacchi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9960-3869","authenticated-orcid":true,"given":"Helen","family":"Stoeckli-Evans","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2020,6,19]]},"reference":[{"key":"dj2010_bb1","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1039\/p19910000089","volume":"1","author":"Botha","year":"1991","journal-title":"J. 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