Acta Crystallographica Section C

Structural Chemistry

Volume 70, Part 4 (April 2014)


organic compounds



sk3540 scheme

Acta Cryst. (2014). C70, 408-415    [ doi:10.1107/S2053229614006007 ]

Four related benzazepine derivatives in a reaction pathway leading to a benzazepine carboxylic acid: hydrogen-bonded assembly in zero, one, two and three dimensions

S. A. Guerrero, C. M. Sanabría, A. Palma, J. Cobo and C. Glidewell

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-H...O hydrogen bonds, and those of compound (I) are linked into chains by C-H...[pi](arene) hydrogen bonds. A combination of O-H...O and O-H...N 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...[pi](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.

CCDC references: 992372, 992373, 992374 and 992375

Formula: C12H13NO3, C12H15NO3, C11H13NO3 and C12H10F3NO3

Keywords: crystal structure; hydrogen bonding; benzazepine derivatives; reaction pathway; supramolecular assembly.


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[ doi:10.1107/S2053229614006007/sk3540Isup6.cml ]
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Chemical Markup Language (CML) file (4.8 kbytes)
[ doi:10.1107/S2053229614006007/sk3540IIsup7.cml ]
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[ doi:10.1107/S2053229614006007/sk3540IIIsup8.cml ]
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