Acta Crystallographica Section C

Crystal Structure Communications

Volume 63, Part 12 (December 2007)


organic compounds



av3112 scheme

Acta Cryst. (2007). C63, o734-o738    [ doi:10.1107/S0108270107053206 ]

Hydrogen-bonding patterns in enaminones: (2Z)-1-(4-bromophenyl)-2-(pyrrolidin-2-ylidene)ethanone and its piperidin-2-ylidene and azepan-2-ylidene analogues

J. L. Balderson, M. A. Fernandes, J. P. Michael and C. B. Perry

Abstract: The title compounds, namely (2Z)-1-(4-bromophenyl)-2-(pyrrolidin-2-ylidene)ethanone, C12H12BrNO, (I), (2Z)-1-(4-bromophenyl)-2-(piperidin-2-ylidene)ethanone, C13H14BrNO, (II), and (2Z)-2-(azepan-2-ylidene)-1-(4-bromophenyl)ethanone, C14H16BrNO, (III), are characterized by bifurcated intra- and intermolecular hydrogen bonding between the secondary amine and carbonyl groups. The former establishes a six-membered hydrogen-bonded ring, while the latter leads to the formation of centrosymmetric dimers. Weak C-H...Br interactions link the individual molecules into chains that run along the [011], [101] and [101] directions in (I)-(III), respectively. Additional weak Br...O, C-H...[pi] and C-H...O interactions further stabilize the crystal structures.

Formula: C12H12BrNO, C13H14BrNO and C14H16BrNO


hkldisplay filedownload file

Structure factor file (CIF format) (124.9 kbytes)
[ doi:10.1107/S0108270107053206/av3112Isup2.hkl ]
Contains datablock I


hkldisplay filedownload file

Structure factor file (CIF format) (139.6 kbytes)
[ doi:10.1107/S0108270107053206/av3112IIsup3.hkl ]
Contains datablock II


hkldisplay filedownload file

Structure factor file (CIF format) (149.2 kbytes)
[ doi:10.1107/S0108270107053206/av3112IIIsup4.hkl ]
Contains datablock III


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