{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T05:16:49Z","timestamp":1736831809896,"version":"3.33.0"},"reference-count":28,"publisher":"International Union of Crystallography (IUCr)","issue":"7","license":[{"start":{"date-parts":[[2015,6,16]],"date-time":"2015-06-16T00:00:00Z","timestamp":1434412800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2015,6,16]],"date-time":"2015-06-16T00:00:00Z","timestamp":1434412800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr C Struct Chem","Acta Crystallogr C","Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst C Struct Chem","Acta Cryst Sect C","Acta Cryst Sect C Struct Chem","Acta Crystallogr Sect C","Acta Crystallogr Sect C Struct Chem","Acta Crystallogr Sect C Cryst Struct Commun"],"published-print":{"date-parts":[[2015,7,1]]},"abstract":"<jats:p>In the solid state, crystals of both 1-(7-chloro-1,4-dihydroquinolin-4-ylidene)thiosemicarbazide\u2013methanol\u2013water (2\/1\/1), 2C<jats:sub>10<\/jats:sub>H<jats:sub>9<\/jats:sub>ClN<jats:sub>4<\/jats:sub>S\u00b7CH<jats:sub>3<\/jats:sub>OH\u00b7H<jats:sub>2<\/jats:sub>O, (I), and its hydrochloride salt {systematic name: [(7-chloro-1,4-dihydroquinolin-4-ylidene)azaniumyl]thiourea chloride}, C<jats:sub>10<\/jats:sub>H<jats:sub>10<\/jats:sub>ClN<jats:sub>4<\/jats:sub>S<jats:sup>+<\/jats:sup>\u00b7Cl<jats:sup>\u2212<\/jats:sup>, (II), assume the imine tautomeric form, contrary to other 4-amino-7-chloroquinolines. Of particular interest are the N\u2014C bond lengths, which have appreciable double-bond character, and the C\u2014N\u2014C aromatic ring bond angle. Both of these parameters have been studied extensively in 4-amino-substituted quinolines. The crystal structures of (I) and (II) in this study provide interesting examples of the amino\u2013imino tautomerism which exists in this class of compound and is, to the best of our knowledge, hitherto unreported.<\/jats:p>","DOI":"10.1107\/s2053229615010311","type":"journal-article","created":{"date-parts":[[2015,6,15]],"date-time":"2015-06-15T13:11:44Z","timestamp":1434373904000},"page":"564-569","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":2,"title":["1-(7-Chloro-1,4-dihydroquinolin-4-ylidene)thiosemicarbazide and its hydrochloride: evidence for the existence of a stable imine tautomer in the solid state of 4-aminoquinoline free bases, an anomalous case in nitrogen heterocycles"],"prefix":"10.1107","volume":"71","author":[{"given":"Rafael C.","family":"Machado","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Richard M.","family":"Grazul","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Renata","family":"Diniz","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2015,6,16]]},"reference":[{"unstructured":"Agilent (2014). 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