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dc.contributor.authorGuerrero, S.A.
dc.contributor.authorSanabría, C.M.
dc.contributor.authorPalma, A.
dc.contributor.authorCobo, J.
dc.contributor.authorGlidewell, C.
dc.date.accessioned2014-08-27T14:31:03Z
dc.date.available2014-08-27T14:31:03Z
dc.date.issued2014-04-01
dc.identifier.citationGuerrero , S A , Sanabría , C M , Palma , A , Cobo , J & Glidewell , C 2014 , ' Four related benzazepine derivatives in a reaction pathway leading to a benzazepine carboxylic acid : hydrogen-bonded assembly in zero, one, two and three dimensions ' , Acta Crystallographica Section C Structural Chemistry , vol. 70 , no. 4 , pp. 408-415 . https://doi.org/10.1107/S2053229614006007en
dc.identifier.issn2053-2296
dc.identifier.otherPURE: 143748030
dc.identifier.otherPURE UUID: 7d5a7764-308b-4e74-945d-63e893da5090
dc.identifier.otherScopus: 84905452860
dc.identifier.otherWOS: 000334050600015
dc.identifier.urihttps://hdl.handle.net/10023/5258
dc.descriptionThe authors thank ‘Centro de Instrumentacion Cientıfico-Tecnica of Universidad de Jaen’ and the staff for data collection. AP, SAG and CMS thank Colciencias for financial support (grant No. 1102–521–28229). JC thanks the Consejerıa de Innovacion, Ciencia y Empresa (Junta de Andalucıa, Spain) and the Universidad de Jaen for financial support.en
dc.description.abstract(2R*,4S*)-Methyl 2,3,4,5-tetra­hydro-1,4-ep­oxy-1H-benz[b]azepine-2-carboxyl­ate, C12H13NO3, (I), and its reduction product (2R*,4S*)-methyl 4-hy­droxy-2,3,4,5-tetra­hydro-1H-benz[b]azepine-2-carboxyl­ate, C12H15NO3, (II), both crystallize as single enanti­omers in the space group P212121, while the hydrolysis product (2RS,4SR)-4-hy­droxy-2,3,4,5-tetra­hydro-1H-benz[b]azepine-2-carb­oxy­lic acid, C11H13NO3, (III), and the lactone (2RS,5SR)-8-(trifluoromethoxy)-5,6-dihydro-1H-2,5-methanobenz[e][1,4]oxazocin-3(2H)-one, C12H10F3NO3, (IV), both crystallize as racemic mixtures in the space group P21/c. The mol­ecules of compound (IV) are linked into centrosymmetric R22(10) dimers by N-HO hydrogen bonds, and those of compound (I) are linked into chains by C-H(arene) hydrogen bonds. A combination of O-HO and O-HN hydrogen bonds links the mol­ecules of com­pound (III) into sheets containing equal numbers of R44(14) and R44(26) rings, and a combination of C-H(arene) hydrogen bonds and three-centre O-H(N,O) hydrogen bonds links the mol­ecules of compound (II) into a three-dimensional frame­work structure. Comparisons are made with some related compounds.
dc.format.extent8
dc.language.isoeng
dc.relation.ispartofActa Crystallographica Section C Structural Chemistryen
dc.rightsCopyright © International Union of Crystallographyen
dc.subjectCrystal structureen
dc.subjectHydrogen bondingen
dc.subjectBenzazepine derivativesen
dc.subjectReaction pathwayen
dc.subjectSupramolecular assemblyen
dc.subjectQD Chemistryen
dc.subject.lccQDen
dc.titleFour related benzazepine derivatives in a reaction pathway leading to a benzazepine carboxylic acid : hydrogen-bonded assembly in zero, one, two and three dimensionsen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.identifier.doihttps://doi.org/10.1107/S2053229614006007
dc.description.statusPeer revieweden
dc.identifier.urlhttp://www.scopus.com/inward/record.url?eid=2-s2.0-84905452860&partnerID=8YFLogxKen
dc.identifier.urlhttp://scripts.iucr.org/cgi-bin/sendsup?cnor=sk3540&type=supplementarymaterialsen


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