2,6,6-Trimethyl­cyclo­hex-2-ene­carb­oxy­lic acid

Parthasarathy, R.; Jenniefer, S.J.; Thomas Muthiah, P.; Sulochana, N.

doi:10.1107/S1600536812002668

Volume 68
Part 2
Page o536
February 2012

Received 15 January 2012
Accepted 21 January 2012
Online 31 January 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.049
wR = 0.134
Data-to-parameter ratio = 18.0
Details

2,6,6-Trimethylcyclohex-2-enecarboxylic acid

Rajasekaran Parthasarathy,^a Samson Jegan Jenniefer,^b Packianathan Thomas Muthiah ^b ^* and Nagarajan Sulochana ^c

^aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India,^bSchool of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamil Nadu, India, and ^cDepartment of Chemistry, National Institute of Technology, Karaikal 609 605, India
Correspondence e-mail: tommtrichy@yahoo.co.in

In the title crystal structure, C₁₀H₁₆O₂, inversion-related molecules are linked by pairs of O-HO hydrogen bonds involving carboxyl groups to form R₂²(8) dimers. The cyclohexene ring displays a half-chair conformation.

Related literature

For information on the title compound as used as a key intermediate in chemical synthesis, see: Eugster et al. (1969); Naef & Decorzant (1986); Snowden et al. (1982); Fehr & Galindo (1986, 1995); Heather et al. (1976). For hydrogen-bond graph-set notation, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₁₀H₁₆O₂
M_r = 168.23
Monoclinic, P 2₁ /c
a = 7.6817 (1) Å
b = 10.4137 (2) Å
c = 13.4421 (2) Å
= 112.924 (1)°
V = 990.38 (3) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 296 K
0.09 × 0.08 × 0.05 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.993, T_max = 0.996
10045 measured reflections
2158 independent reflections
1560 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.134
S = 1.03
2158 reflections
120 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.25 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AO1ⁱ	1.01 (4)	1.64 (4)	2.646 (2)	178 (4)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5406 ).

Acknowledgements

PTM and SJJ thank the DST India (FIST programme) for the use of the diffractometer at the School of Chemistry, Bharathidasan University, Tiruchirappalli, Tamil Nadu, India.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Eugster, C. H., Buchecker, R., Tscharner, C., Uhde, G. & Ohloff, G. (1969). Helv. Chim. Acta, 52, 1729-1731.
Fehr, C. & Galindo, J. (1986). Helv. Chim. Acta, 69, 228-235.
Fehr, C. & Galindo, J. (1995). Helv. Chim. Acta, 78, 539-552.
Heather, J. B., Mittal, R. S. D. & Sih, C. J. (1976). J. Am. Chem. Soc. 98, 3661-3669.
Naef, F. & Decorzant, R. (1986). Tetrahedron, 42, 3245-3250.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Snowden, R. L., Muller, B. L. & Schulte-Elte, K. H. (1982). Tetrahedron Lett. 23, 335-338.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds