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Volume 69 
Part 5 
Page o734  
May 2013  

Received 2 January 2013
Accepted 10 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.053
wR = 0.141
Data-to-parameter ratio = 17.7
Details
Open access

(1R*,2R*,3S*,4R*)-Diethyl 4-hydroxy-4-methyl-2-(4-methylphenyl)-6-oxocyclohexane-1,3-dicarboxylate

aBaku State University, Z. Khalilov St 23, Baku AZ-1148, Azerbaijan, and bVladimir State University, Qor'ky St. 87, Vladimir 600000, Russian Federation
Correspondence e-mail: kushvarlab7@gmail.com

The title compound, C20H26O6, is chiral and crystallizes as a racemate: the relative configuration of the stereogenic centres is 1R*,2R*,3S*,4R*. The cyclohexane ring has a chair conformation. The ethyl fragment of the ethoxycarbonyl group in the 3-position is disordered over two sets of sites in a 0.650 (6):0.350 (6) ratio. The hydroxy group acts as a bifurcated hydrogen-bond donor, forming both intra- and intermolecular hydrogen bonds with ester carbonyl O atoms. The intermolecular hydrogen bonds form inversion dimers in the crystal.

Related literature

For applications of related compounds as synthetic intermediates, see: Gein et al. (2003[Gein, V. L., Gein, N. V. & Krivenko, A. P. (2003). Russ. J. Gen. Chem. 73, 490-491.], 2004[Gein, V. L., Gein, N. V., Potemkin, K. D. & Krivenko, A. P. (2004). Russ. J. Gen. Chem. 74, 1564-1568.]); Sorokin et al. (2000[Sorokin, V. V., Grigor'ev, A. V., Ramazanov, A. K. & Krivenko, A. P. (2000). Russ. J. Org. Chem. 36, 781-784.]).

[Scheme 1]

Experimental

Crystal data
  • C20H26O6

  • Mr = 362.41

  • Triclinic, [P \overline 1]

  • a = 5.8062 (4) Å

  • b = 9.9267 (7) Å

  • c = 18.4548 (13) Å

  • [alpha] = 103.281 (2)°

  • [beta] = 92.490 (2)°

  • [gamma] = 104.741 (2)°

  • V = 995.26 (12) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.974, Tmax = 0.983

  • 10589 measured reflections

  • 4344 independent reflections

  • 2735 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.141

  • S = 1.01

  • 4344 reflections

  • 245 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O6-H6...O1 0.91 (4) 2.28 (4) 2.884 (2) 124 (3)
O6-H6...O1i 0.91 (4) 2.28 (4) 3.066 (2) 145 (3)
Symmetry code: (i) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2087 ).


Acknowledgements

We thank Baku State University and Vladimir State University for supporting this study.

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Gein, V. L., Gein, N. V. & Krivenko, A. P. (2003). Russ. J. Gen. Chem. 73, 490-491.  [ISI] [CrossRef] [ChemPort]
Gein, V. L., Gein, N. V., Potemkin, K. D. & Krivenko, A. P. (2004). Russ. J. Gen. Chem. 74, 1564-1568.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sorokin, V. V., Grigor'ev, A. V., Ramazanov, A. K. & Krivenko, A. P. (2000). Russ. J. Org. Chem. 36, 781-784.  [ChemPort]


Acta Cryst (2013). E69, o734  [ doi:10.1107/S1600536813009872 ]

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