{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2024,12,21]],"date-time":"2024-12-21T05:16:47Z","timestamp":1734758207812,"version":"3.32.0"},"reference-count":30,"publisher":"International Union of Crystallography (IUCr)","issue":"11","license":[{"start":{"date-parts":[[2024,10,15]],"date-time":"2024-10-15T00:00:00Z","timestamp":1728950400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2024,10,15]],"date-time":"2024-10-15T00:00:00Z","timestamp":1728950400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/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"],"accepted":{"date-parts":[[2024,9,26]]},"published-print":{"date-parts":[[2024,11,1]]},"abstract":"<jats:p>The structures of the title compounds 2-hydroxy-<jats:italic>N<\/jats:italic>\u2032-methylacetohydrazide, <jats:bold>1<\/jats:bold>, and 2-hydroxy-<jats:italic>N<\/jats:italic>-methylacetohydrazide, <jats:bold>2<\/jats:bold>, both C<jats:sub>3<\/jats:sub>H<jats:sub>8<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>, as regioisomers differ in the position of the methyl group relative to the N atoms in 2-hydroxy-acetohydrazide. In the structure of <jats:bold>1<\/jats:bold>, the 2-hydroxy-acetohydrazide core [OH\u2014C\u2014C(=O)\u2014NH\u2014NH] is almost planar and the methyl group is rotated relative to this plane. As opposed to <jats:bold>1<\/jats:bold>, in the structure of <jats:bold>2<\/jats:bold> all non-hydrogen atoms lie in the same plane. The hydroxyl and carbonyl groups in structures <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold> are in <jats:italic>trans<\/jats:italic> and <jats:italic>cis<\/jats:italic> positions, respectively. The methyl amino group and carbonyl group are in the <jats:italic>cis<\/jats:italic> position relative to the C\u2014N bond in structure <jats:bold>1<\/jats:bold>, while the amino group and carbonyl group are in the <jats:italic>trans<\/jats:italic> position relative to the C\u2014N bond in stucture <jats:bold>2.<\/jats:bold> In the crystal, molecules of <jats:bold>1<\/jats:bold> are linked by N\u2014H...O and O\u2014H...N intermolecular hydrogen bonds, forming layers parallel to the <jats:italic>ab<\/jats:italic> crystallographic plane. A Hirshfeld surface analysis showed that the H...H contacts dominate the crystal packing with a contribution of 55.3%. The contribution of the H...O\/O...H interaction is somewhat smaller, amounting to 30.8%. In the crystal, as a result of the intermolecular O\u2014H...O hydrogen bonds, molecules of <jats:bold>2<\/jats:bold> form dimers, which are linked by N\u2014H...O hydrogen bonds and a three-dimensional supramolecular network The major contributors to the Hirshfeld surface are H...H (58.5%) and H...O\/O...H contacts (31.7%).<\/jats:p>","DOI":"10.1107\/s2056989024009526","type":"journal-article","created":{"date-parts":[[2024,10,15]],"date-time":"2024-10-15T08:03:18Z","timestamp":1728979398000},"page":"1170-1174","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis, structures and Hirshfeld surface analyses of 2-hydroxy-<i>N<\/i>\u2032-methylacetohydrazide and 2-hydroxy-<i>N<\/i>-methylacetohydrazide"],"prefix":"10.1107","volume":"80","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5666-5592","authenticated-orcid":true,"given":"Oleksandr V.","family":"Vashchenko","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7058-832X","authenticated-orcid":true,"given":"Dmytro M.","family":"Khomenko","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4613-172X","authenticated-orcid":true,"given":"Viktoriya V.","family":"Dyakonenko","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8326-4535","authenticated-orcid":true,"given":"Rostyslav D.","family":"Lampeka","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2024,10,15]]},"reference":[{"key":"yz2059_bb1","doi-asserted-by":"crossref","first-page":"o2305","DOI":"10.1107\/S1600536808035964","volume":"64","author":"Abu-Safieh","year":"2008","journal-title":"Acta Cryst. 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