{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,7]],"date-time":"2025-10-07T00:15:13Z","timestamp":1759796113930,"version":"build-2065373602"},"reference-count":25,"publisher":"International Union of Crystallography (IUCr)","issue":"10","license":[{"start":{"date-parts":[[2025,9,9]],"date-time":"2025-09-09T00:00:00Z","timestamp":1757376000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2025,9,9]],"date-time":"2025-09-09T00:00:00Z","timestamp":1757376000000},"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":[[2025,9,3]]},"published-print":{"date-parts":[[2025,10,1]]},"abstract":"<jats:p>The crystal structures of two hydrochloride salts of pyridoxal\u2013<jats:italic>N<\/jats:italic>-acylhydrazone\u2013Q (Q = heterocyclic aromatic ring) derivatives, <jats:italic>viz<\/jats:italic>. (<jats:italic>E<\/jats:italic>)-3-hydroxy-5-(hydroxymethyl)-2-methyl-4-{[(pyridin-4-ylformamido)imino]methyl}pyridin-1-ium chloride dihydrate, C<jats:sub>14<\/jats:sub>H<jats:sub>15<\/jats:sub>N<jats:sub>4<\/jats:sub>O<jats:sub>3<\/jats:sub>\n                  <jats:sup>+<\/jats:sup>\u00b7Cl<jats:sup>\u2212<\/jats:sup>\u00b72H<jats:sub>2<\/jats:sub>O, (<jats:bold>I<\/jats:bold>), and (<jats:italic>E<\/jats:italic>)-3-hydroxy-5-(hydroxymethyl)-2-methyl-4-{[(pyrimidin-2-ylformamido)imino]methyl}pyridin-1-ium chloride dihydrate, C<jats:sub>13<\/jats:sub>H<jats:sub>14<\/jats:sub>N<jats:sub>5<\/jats:sub>O<jats:sub>3<\/jats:sub>\n                  <jats:sup>+<\/jats:sup>\u00b7Cl<jats:sup>\u2212<\/jats:sup>\u00b72H<jats:sub>2<\/jats:sub>O, (<jats:bold>II<\/jats:bold>) are described. The cations, which are protonated at the pyridine N atom of the pyridoxal ring, have similar overall conformations: the dihedral angles between the pyridoxal ring and the terminal aromatic ring are 12.63\u2005(12) and 6.11\u2005(15)\u00b0 for (<jats:bold>I<\/jats:bold>) and (<jats:bold>II<\/jats:bold>), respectively. Each cation features an intramolecular O\u2014H...N hydrogen bond, which closes an <jats:italic>S<\/jats:italic>(6) ring, but a difference arises in the conformation of the C\u2014C\u2014C\u2014O fragment terminated by the the ring carbon atom bonded to the side chain and the O atom of the hydroxymethyl group: <jats:italic>gauche<\/jats:italic> for (<jats:bold>I<\/jats:bold>) and <jats:italic>anti<\/jats:italic> for (<jats:bold>II<\/jats:bold>). The extended structures of (<jats:bold>I<\/jats:bold>) and (<jats:bold>II<\/jats:bold>) feature numerous strong (N\u2014H and O\u2014H donors) and weak (C\u2014H donor) hydrogen bonds. In (<jats:bold>I<\/jats:bold>), the NH<jats:sub>p<\/jats:sub> (pyridine) grouping links to the terminal N atom of the pendant unprotonated pyridine ring of an adjacent cation to generate [010] chains, whereas the NH<jats:sub>h<\/jats:sub> (hydrazide) and OH<jats:sub>hm<\/jats:sub> (hydroxymethyl) moieties link to chloride ion acceptors. In (<jats:bold>II<\/jats:bold>), the NH<jats:sub>p<\/jats:sub> and OH<jats:sub>hm<\/jats:sub> groupings bond to chloride anions whereas NH<jats:sub>h<\/jats:sub> bonds to a water molecule. Hydrogen-bonded chains of water molecules occur in (<jats:bold>I<\/jats:bold>) and centrosymmetric tetramers in (<jats:bold>II<\/jats:bold>). The Hirshfeld surfaces of (<jats:bold>I<\/jats:bold>) and (<jats:bold>II<\/jats:bold>) are computed and the structures of related compounds are briefly compared.<\/jats:p>","DOI":"10.1107\/s2056989025007856","type":"journal-article","created":{"date-parts":[[2025,9,9]],"date-time":"2025-09-09T07:37:47Z","timestamp":1757403467000},"page":"938-943","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Different packing motifs mediated by hydrogen bonds in the hydrochloride salts of two pyridoxal <i>N<\/i>-acylhydrazone derivatives"],"prefix":"10.1107","volume":"81","author":[{"given":"Thais C. M.","family":"Nogueira","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Marcus V. 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