Acta Crystallographica Section C

Structural Chemistry

Volume 70, Part 3 (March 2014)


organic compounds



yf3057 scheme

Acta Cryst. (2014). C70, 332-337    [ doi:10.1107/S2053229614003568 ]

Three closely related dibenzazepine carb­oxy­lic acids: hydrogen-bonded aggregation in one, two and three dimensions

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

Abstract: In the structure of (6R*,11R*)-5-acetyl-11-ethyl-6,11-di­hydro-5H-dibenzo[b,e]azepine-6-carb­oxy­lic acid, C19H19NO3, (I), the mol­ecules are linked into sheets by a combination of O-H...O and C-H...O hydrogen bonds; in the structure of the monomethyl analogue (6RS,11SR)-5-acetyl-11-ethyl-2-methyl-6,11-di­hydro-5H-dibenzo[b,e]azepine-6-carb­oxy­lic acid, C20H21NO3, (II), the mol­ecules are linked into simple C(7) chains by O-H...O hydrogen bonds; and in the structure of the di­methyl analogue (6RS,11SR)-5-acetyl-11-ethyl-1,3-di­methyl-6,11-di­hydro-5H-dibenzo[b,e]azepine-6-carb­oxy­lic acid, C21H23NO3, (III), a combination of O-H...O, C-H...O and C-H...[pi](arene) hydrogen bonds links the mol­ecules into a three-dimensional framework structure. None of these structures exhibits the R22(8) dimer motif characteristic of simple carb­oxy­lic acids.

CCDC references: 987415, 987416 and 987417

Formula: C19H19NO3, C20H21NO3 and C21H23NO3

Keywords: crystal structure; dibenzo[b,e]azepine-6-carb­oxy­lic acid; hydrogen bonding; hydrogen-bonded supra­molecular aggregation.


hkldisplay filedownload file

Structure factor file (CIF format) (91.1 kbytes)
[ doi:10.1107/S2053229614003568/yf3057Isup2.hkl ]
Contains datablock I


hkldisplay filedownload file

Structure factor file (CIF format) (191.3 kbytes)
[ doi:10.1107/S2053229614003568/yf3057IIsup3.hkl ]
Contains datablock II


hkldisplay filedownload file

Structure factor file (CIF format) (162.7 kbytes)
[ doi:10.1107/S2053229614003568/yf3057IIIsup4.hkl ]
Contains datablock III


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