Acta Cryst. (2001). B57, 705-713 [doi:10.1107/S0108768101009624]
Abstract: X-ray diffraction analyses of 2-substituted cyclohexanone oximes C5H9(X)C=NOH [X = SMe (1), NMe2 (2)] and of the parent compound [X = H (3)] showed that their cyclohexyl rings are in a slightly distorted chair conformation. These compounds assume in the solid state the (E) configuration bearing the 2-substituents in the axial conformation. Compounds (1) and (2) exist as dimeric and polymeric hydrogen-bond associates, respectively. Low-temperature X-ray analysis of the cyclohexanone oxime (3) showed that the molecules are associated forming two independent trimers. The dimer in (1) and the trimer in (3) are built up via [O-H
N=C] hydrogen bonds, while the polymer of (2) is via the [OHNMe2] hydrogen bond. The comparative IR ![[bold nu]](/logos/entities/nu_bdgif.gif)
OH and C=N analysis of the title compounds, in the solid state and in CCl4 solution, fully supports the nature of the associates for (1)-(3) obtained by X-ray diffraction. The IR azomethyne frequency shift analysis (![[Delta]](/logos/entities/Delta_rmgif.gif)
C=N) also suggests the occurrence of the ![[bold pi]](/logos/entities/pi_bdgif.gif)
C=N/![[bold sigma]](/logos/entities/sigma_bdgif.gif)
*C-X orbital interaction which stabilizes the axial conformations of (1) and (2).
Online 29 September 2001
 |   Structure factor file (CIF format) (79.0 kbytes) |
| Structure factor file (CIF format) (217.5 kbytes) |
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