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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(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
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.
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