Received 6 August 2009
The chiral title compound [systematic name: 4-(1-methylvinyl)cyclohexene-1-carbaldehyde oxime], C10H15NO, crystallizes with two molecules in the asymmetric unit, one of which shows disorder of its propenyl substituent over two sets of sites in a 50:50 ratio. In both molecules, the six-membered carbaldehyde oxime ring adopts an approximate envelope conformation in which the C atom bearing the propenyl substituent represents the flap position. In both molecules, the plane passing through the propenyl substituent is nearly perpendicular to the mean plane of the six-membered ring [dihedral angles = 84.6 (6) and 87.4 (3)°]. In the crystal, the two independent molecules are linked by a pair O-HN hydrogen bonds across a pseudo-inversion centre, generating a dimer. The unit cell of the known racemate of the title compound is similar to the cell found here, but with space group P.
Perillartine or perillartin [(S)-4-(prop-1-en-2-yl)cyclohex-1-ene carbaldehyde oxime], the oxime of perillaldehyde, is 2000 times sweeter than sucrose; see the handbook of artificial sweeteners by O'Brien Nabors & Gelardi (2001). For the crystal structure of the racemic compound, see: Hooft et al. (1990).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5034 ).
We thank the Key Subject Construction Project of Hunan Province (No. 2006-180), the Key Scientific Research Project of Hunan Provincial Education Department (No. 08 A023), the NSF of Hunan Province (No. 09 J J3028) and the University of Malaya for supporting this study.
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