{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T21:49:40Z","timestamp":1740174580522,"version":"3.37.3"},"reference-count":40,"publisher":"International Union of Crystallography (IUCr)","issue":"10","license":[{"start":{"date-parts":[[2018,9,25]],"date-time":"2018-09-25T00:00:00Z","timestamp":1537833600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},{"start":{"date-parts":[[2018,9,25]],"date-time":"2018-09-25T00:00:00Z","timestamp":1537833600000},"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":[[2018,10,1]]},"abstract":"<jats:p>The crystal structures of three salicyaldoxime compounds, namely 2-hydroxy-4-methylbenzaldehyde oxime, C<jats:sub>8<\/jats:sub>H<jats:sub>9<\/jats:sub>NO<jats:sub>2<\/jats:sub>,<jats:bold>1<\/jats:bold>, 2,4-dihydroxybenzaldehyde oxime, C<jats:sub>7<\/jats:sub>H<jats:sub>7<\/jats:sub>NO<jats:sub>3<\/jats:sub>,<jats:bold>2<\/jats:bold>, and 2-hydroxy-4-methoxybenzaldehyde oxime, C<jats:sub>8<\/jats:sub>H<jats:sub>9<\/jats:sub>NO<jats:sub>3<\/jats:sub>,<jats:bold>3<\/jats:bold>, are discussed. In each compound, the hydroxyl groups are essentially coplanar with their attached phenyl group. The interplanar angles between the C=N\u2014O moieties of the oxime unit and their attached phenyl rings are 0.08\u2005(9), 1.08\u2005(15) and 6.65\u2005(15)\u00b0 in<jats:bold>1<\/jats:bold>,<jats:bold>2<\/jats:bold>and<jats:bold>3<\/jats:bold>, respectively. In all three molecules, the 2-hydroxy group forms an intramolecular O\u2014H...N(oxime) hydrogen bond. In compound (<jats:bold>1<\/jats:bold>), intermolecular O\u2014H(oxime)...O(hydroxyl) hydrogen bonds generate<jats:italic>R<\/jats:italic><jats:sup>2<\/jats:sup><jats:sub>2<\/jats:sub>(14) dimers, related by inversion centres. In compound<jats:bold>2<\/jats:bold>, intermolecular O\u2014H(oxime)...O(4-hydroxy) hydrogen bonds generate<jats:italic>C<\/jats:italic>9 chains along the<jats:italic>b<\/jats:italic>-axis direction, while O\u2014H(4-hydroxyl)...O(2-hydroxyl) interactions form zigzag<jats:italic>C<\/jats:italic>6 spiral chains along the c-axis direction, generated by a screw axis at 1,<jats:italic>y<\/jats:italic>, 1\/4: the combination of the two chains provides a bimolecular sheet running parallel to the<jats:italic>b<\/jats:italic>axis, which lies between 0\u20131\/2<jats:italic>c<\/jats:italic>and 1\/2\u20131<jats:italic>c<\/jats:italic>. In compound<jats:bold>3<\/jats:bold>, similar<jats:italic>C<\/jats:italic>9 chains, along the<jats:italic>b-<\/jats:italic>axis direction are generated by O\u2014H(oxime)...O(4-methoxy) hydrogen bonds. Further weaker, C\u2014H...\u03c0 (in<jats:bold>1<\/jats:bold>), \u03c0\u2013\u03c0 (in<jats:bold>2<\/jats:bold>) and both C\u2014H...\u03c0 and \u03c0\u2013\u03c0 interactions (in<jats:bold>3<\/jats:bold>) further cement the three-dimensional structures. Hirshfeld surface and fingerprint analyses are discussed.<\/jats:p>","DOI":"10.1107\/s2056989018013361","type":"journal-article","created":{"date-parts":[[2018,9,25]],"date-time":"2018-09-25T08:46:21Z","timestamp":1537865181000},"page":"1480-1485","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-<i>X<\/i>C<sub>6<\/sub>H<sub>3<\/sub>C=NOH (<i>X<\/i>= Me, OH and MeO)"],"prefix":"10.1107","volume":"74","author":[{"given":"Ligia R.","family":"Gomes","sequence":"first","affiliation":[]},{"given":"Marcus V. 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