{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,9]],"date-time":"2025-11-09T07:48:44Z","timestamp":1762674524557,"version":"3.33.0"},"reference-count":22,"publisher":"International Union of Crystallography (IUCr)","issue":"11","license":[{"start":{"date-parts":[[2021,10,26]],"date-time":"2021-10-26T00:00:00Z","timestamp":1635206400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2021,10,26]],"date-time":"2021-10-26T00:00:00Z","timestamp":1635206400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/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":[[2021,10,20]]},"published-print":{"date-parts":[[2021,11,1]]},"abstract":"<jats:p>The structures of the six hydrogen-bonded 1:1 compounds of 4-methylquinoline (C<jats:sub>10<\/jats:sub>H<jats:sub>9<\/jats:sub>N) with chloro- and nitro-substituted benzoic acids (C<jats:sub>7<\/jats:sub>H<jats:sub>4<\/jats:sub>ClNO<jats:sub>4<\/jats:sub>), namely, 4-methylquinolinium 2-chloro-4-nitrobenzoate, C<jats:sub>10<\/jats:sub>H<jats:sub>10<\/jats:sub>N<jats:sup>+<\/jats:sup>\u00b7C<jats:sub>7<\/jats:sub>H<jats:sub>3<\/jats:sub>ClNO<jats:sub>4<\/jats:sub>\n                  <jats:sup>\u2212<\/jats:sup>, (I), 4-methylquinoline\u20132-chloro-5-nitrobenzoic acid (1\/1), C<jats:sub>10<\/jats:sub>H<jats:sub>9<\/jats:sub>N\u00b7C<jats:sub>7<\/jats:sub>H<jats:sub>4<\/jats:sub>ClNO<jats:sub>4<\/jats:sub>, (II), 4-methylquinolinium 2-chloro-6-nitrobenzoate, C<jats:sub>10<\/jats:sub>H<jats:sub>9.63<\/jats:sub>N<jats:sup>0.63+<\/jats:sup>\u00b7C<jats:sub>7<\/jats:sub>H<jats:sub>3.37<\/jats:sub>ClNO<jats:sub>4<\/jats:sub>\n                  <jats:sup>0.63\u2212<\/jats:sup>, (III), 4-methylquinolinium 3-chloro-2-nitrobenzoate, C<jats:sub>10<\/jats:sub>H<jats:sub>9.54<\/jats:sub>N<jats:sup>0.54+<\/jats:sup>\u00b7C<jats:sub>7<\/jats:sub>H<jats:sub>3.46<\/jats:sub>ClNO<jats:sub>4<\/jats:sub>\n                  <jats:sup>0.54\u2212<\/jats:sup>, (IV), 4-methylquinolinium 4-chloro-2-nitrobenzoate, C<jats:sub>10<\/jats:sub>H<jats:sub>10<\/jats:sub>N<jats:sup>+<\/jats:sup>\u00b7C<jats:sub>7<\/jats:sub>H<jats:sub>3<\/jats:sub>ClNO<jats:sub>4<\/jats:sub>\n                  <jats:sup>\u2212<\/jats:sup>, (V), and 4-methylquinolinium 5-chloro-2-nitrobenzoate, C<jats:sub>10<\/jats:sub>H<jats:sub>10<\/jats:sub>N<jats:sup>+<\/jats:sup>\u00b7C<jats:sub>7<\/jats:sub>H<jats:sub>3<\/jats:sub>ClNO<jats:sub>4<\/jats:sub>\n                  <jats:sup>\u2212<\/jats:sup>, have been determined at 185\u2013190\u2005K. In each compound, the acid and base molecules are linked by a short hydrogen bond between a carboxy (or carboxylate) O atom and an N atom of the base. The O...N distances are 2.5652\u2005(14), 2.556\u2005(3), 2.5485\u2005(13), 2.5364\u2005(13), 2.5568\u2005(13) and 2.5252\u2005(11)\u2005\u00c5, respectively, for compounds (I)\u2013(VI). In the hydrogen-bonded acid\u2013base units of (III) and (IV), the H atoms are each disordered over two positions with O site:N site occupancies of 0.37\u2005(3):0.63\u2005(3) and 0.46\u2005(3):0.54\u2005(4), respectively, for (III) and (IV). The H atoms in the hydrogen-bonded units of (I), (V) and (VI) are located at the N-atom site, while the H atom in (II) is located at the O-atom site. In all the crystals of (I)\u2013(VI), \u03c0\u2013\u03c0 stacking interactions between the quinoline ring systems and C\u2014H...O hydrogen bonds are observed. Similar layer structures are constructed in (IV)\u2013(VI) through these interactions together with \u03c0\u2013\u03c0 interactions between the benzene rings of the adjacent acid molecules. A short Cl...Cl contact and an N\u2014O...\u03c0 interaction are present in (I), while a C\u2014H...Cl hydrogen bond and a \u03c0\u2013\u03c0 interaction between the benzene ring of the acid molecule and the quinoline ring system in (II), and a C\u2014H...\u03c0 interaction in (III) are observed. Hirshfeld surfaces for the title compounds mapped over <jats:italic>d<\/jats:italic>\n                  <jats:sub>norm<\/jats:sub> and shape index were generated to visualize the weak intermolecular interactions.<\/jats:p>","DOI":"10.1107\/s2056989021010896","type":"journal-article","created":{"date-parts":[[2021,10,26]],"date-time":"2021-10-26T07:55:49Z","timestamp":1635234949000},"page":"1144-1152","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["Role of p<i>K<\/i>\n                  <sub>a<\/sub> in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids"],"prefix":"10.1107","volume":"77","author":[{"given":"Hiroyuki","family":"Ishida","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2021,10,26]]},"reference":[{"key":"hb7991_bb1","doi-asserted-by":"crossref","first-page":"343","DOI":"10.1107\/S0021889892010331","volume":"26","author":"Altomare","year":"1993","journal-title":"J. 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