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Four related benzazepine derivatives in a reaction pathway leading to a benzazepine carboxylic acid : hydrogen-bonded assembly in zero, one, two and three dimensions
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dc.contributor.author | Guerrero, S.A. | |
dc.contributor.author | Sanabría, C.M. | |
dc.contributor.author | Palma, A. | |
dc.contributor.author | Cobo, J. | |
dc.contributor.author | Glidewell, C. | |
dc.date.accessioned | 2014-08-27T14:31:03Z | |
dc.date.available | 2014-08-27T14:31:03Z | |
dc.date.issued | 2014-04-01 | |
dc.identifier.citation | Guerrero , 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/S2053229614006007 | en |
dc.identifier.issn | 2053-2296 | |
dc.identifier.other | PURE: 143748030 | |
dc.identifier.other | PURE UUID: 7d5a7764-308b-4e74-945d-63e893da5090 | |
dc.identifier.other | Scopus: 84905452860 | |
dc.identifier.other | WOS: 000334050600015 | |
dc.identifier.uri | https://hdl.handle.net/10023/5258 | |
dc.description | The 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.extent | 8 | |
dc.language.iso | eng | |
dc.relation.ispartof | Acta Crystallographica Section C Structural Chemistry | en |
dc.rights | Copyright © International Union of Crystallography | en |
dc.subject | Crystal structure | en |
dc.subject | Hydrogen bonding | en |
dc.subject | Benzazepine derivatives | en |
dc.subject | Reaction pathway | en |
dc.subject | Supramolecular assembly | en |
dc.subject | QD Chemistry | en |
dc.subject.lcc | QD | en |
dc.title | Four related benzazepine derivatives in a reaction pathway leading to a benzazepine carboxylic acid : hydrogen-bonded assembly in zero, one, two and three dimensions | en |
dc.type | Journal article | en |
dc.description.version | Publisher PDF | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | https://doi.org/10.1107/S2053229614006007 | |
dc.description.status | Peer reviewed | en |
dc.identifier.url | http://www.scopus.com/inward/record.url?eid=2-s2.0-84905452860&partnerID=8YFLogxK | en |
dc.identifier.url | http://scripts.iucr.org/cgi-bin/sendsup?cnor=sk3540&type=supplementarymaterials | en |
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