Four related benzazepine derivatives in a reaction pathway leading to a benzazepine carboxylic acid : hydrogen-bonded assembly in zero, one, two and three dimensions
MetadataShow full item record
(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.
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 . DOI: 10.1107/S2053229614006007
Acta Crystallographica Section C Structural Chemistry
Copyright © International Union of Crystallography
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.
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.