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Volume 65 
Part 9 
Page o2149  
September 2009  

Received 6 August 2009
Accepted 6 August 2009
Online 15 August 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.043
wR = 0.139
Data-to-parameter ratio = 8.9
Details
Open access

Perillartine

aDepartment of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan 425100, People's Republic of China, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

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-H...N 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[\overline{1}].

Related literature

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[O'Brien Nabors, L. & Gelardi, R. C. (2001). Alternative Sweeteners, 3rd ed. Boca Raton: CRC Press.]). For the crystal structure of the racemic compound, see: Hooft et al. (1990[Hooft, R. W. W., van der Sluis, P., Kanters, J. A. & Kroon, J. (1990). Acta Cryst. C46, 1133-1135.]).

[Scheme 1]

Experimental

Crystal data
  • C10H15NO

  • Mr = 165.23

  • Triclinic, P 1

  • a = 7.2679 (6) Å

  • b = 8.1702 (7) Å

  • c = 8.9426 (8) Å

  • [alpha] = 105.150 (1)°

  • [beta] = 95.658 (1)°

  • [gamma] = 104.602 (1)°

  • V = 488.25 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 293 K

  • 0.48 × 0.42 × 0.22 mm

Data collection
  • Bruker SMART diffractometer

  • Absorption correction: none

  • 4074 measured reflections

  • 2078 independent reflections

  • 1457 reflections with I > 2[sigma](I)

  • Rint = 0.010

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.139

  • S = 1.07

  • 2078 reflections

  • 234 parameters

  • 21 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N2 0.85 (4) 2.00 (2) 2.831 (4) 164 (5)
O2-H2...N1 0.85 (4) 2.04 (2) 2.811 (4) 150 (4)

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5034 ).


Acknowledgements

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.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Hooft, R. W. W., van der Sluis, P., Kanters, J. A. & Kroon, J. (1990). Acta Cryst. C46, 1133-1135.  [CrossRef] [details]
O'Brien Nabors, L. & Gelardi, R. C. (2001). Alternative Sweeteners, 3rd ed. Boca Raton: CRC Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2009). publCIF. In preparation.


Acta Cryst (2009). E65, o2149  [ doi:10.1107/S1600536809031225 ]

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