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

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.