{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,7,26]],"date-time":"2025-07-26T08:47:50Z","timestamp":1753519670818,"version":"3.37.3"},"reference-count":27,"publisher":"International Union of Crystallography (IUCr)","issue":"11","license":[{"start":{"date-parts":[[2022,10,4]],"date-time":"2022-10-04T00:00:00Z","timestamp":1664841600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2022,10,4]],"date-time":"2022-10-04T00:00:00Z","timestamp":1664841600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/100008524","name":"University of Montana","doi-asserted-by":"crossref","award":["325490"],"award-info":[{"award-number":["325490"]}],"id":[{"id":"10.13039\/100008524","id-type":"DOI","asserted-by":"crossref"}]},{"DOI":"10.13039\/100000057","name":"National Institutes of Health, National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["P30GM140963"],"award-info":[{"award-number":["P30GM140963"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]}],"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":[[2022,9,26]]},"published-print":{"date-parts":[[2022,11,1]]},"abstract":"<jats:p>Three hexahydroquinoline derivatives were synthesized and crystallized in an effort to study the structure\u2013activity relationships of these calcium-channel antagonists. The derivatives are ethyl 4-(2-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C<jats:sub>22<\/jats:sub>H<jats:sub>27<\/jats:sub>NO<jats:sub>4<\/jats:sub>, (I), ethyl 4-(4-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C<jats:sub>22<\/jats:sub>H<jats:sub>27<\/jats:sub>NO<jats:sub>4<\/jats:sub>, (II), and ethyl 4-(3,4-dihydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C<jats:sub>21<\/jats:sub>H<jats:sub>24<\/jats:sub>NO<jats:sub>5<\/jats:sub>, (III). In these hexahydroquinoline derivatives, common structural features such as a flat-boat conformation of the 1,4-dihydropyridine (1,4-DHP) ring, an envelope conformation of the fused cyclohexanone ring, and a substituted phenyl group at the pseudo-axial position are retained. Hydrogen bonds are the main contributors to the packing of the molecules in these crystals.<\/jats:p>","DOI":"10.1107\/s2056989022009495","type":"journal-article","created":{"date-parts":[[2022,10,4]],"date-time":"2022-10-04T08:16:55Z","timestamp":1664871415000},"page":"1089-1096","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["Synthesis, crystal structures, and Hirshfeld analysis of three hexahydroquinoline derivatives"],"prefix":"10.1107","volume":"78","author":[{"given":"Scott A.","family":"Steiger","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chun","family":"Li","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0511-1127","authenticated-orcid":true,"given":"Allen G.","family":"Oliver","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nicholas R.","family":"Natale","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2022,10,4]]},"reference":[{"key":"jy2021_bb1","doi-asserted-by":"crossref","first-page":"103187","DOI":"10.1016\/j.bioorg.2019.103187","volume":"91","author":"Ayg\u00fcn Cevher","year":"2019","journal-title":"Bioorg. 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