2-Hy­droxy-6-isopropyl-3-methyl­benzoic acid

Betz, R.; Gerber, T.; Schalekamp, H.

doi:10.1107/S1600536811011998

Volume 67
Part 5
Page o1063
May 2011

Received 17 March 2011
Accepted 31 March 2011
Online 7 April 2011

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.003 Å
R = 0.054
wR = 0.154
Data-to-parameter ratio = 19.3
Details

2-Hydroxy-6-isopropyl-3-methylbenzoic acid

Richard Betz,^a ^* Thomas Gerber ^a and Henk Schalekamp ^a

^aNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

The title compound, C₁₁H₁₄O₃, is a multiple-substituted derivative of benzoic acid. Intracyclic C-C-C angles span a range of 117.16 (19)-122.32 (19)°. Apart from intramolecular hydrogen bonds between hydroxyl and carboxyl groups, intermolecular hydrogen bonds are present in the crystal structure, the latter ones giving rise to centrosymmetric carboxylic acid dimers.

Related literature

For the X-ray crystal structure of benzoic acid, see: Bruno & Randaccio (1980). For the crystal structure of benzoic acid applying neutron radiation, see: Wilson et al. (1996). For the crystal structure of meta-methylbenzoic acid (without three-dimensional coordinates), see: Ellas & García-Blanco (1963). For a recent crystal structure analysis of salicylic acid, see: Munshi & Guru Row (2006). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₁₁H₁₄O₃
M_r = 194.22
Orthorhombic, P b c a
a = 16.8864 (17) Å
b = 6.6653 (7) Å
c = 18.238 (2) Å
V = 2052.7 (4) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 200 K
0.51 × 0.16 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
10325 measured reflections
2546 independent reflections
1365 reflections with I > 2(I)
R_int = 0.073

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.154
S = 0.99
2546 reflections
132 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3O2	0.84	1.77	2.5171 (19)	146
O1-H1O2ⁱ	0.84	1.81	2.6475 (19)	174
Symmetry code: (i) -x, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2346 ).

Acknowledgements

The authors thank Mrs Hazel Kendrick for helpful discussions.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2010). APEX2 and SAINT Bruker AXS Inc., Madison, USA.
Bruno, G. & Randaccio, L. (1980). Acta Cryst. B36, 1711-1712.
Ellas, J. L. & García-Blanco, S. (1963). Acta Cryst. 16, 434.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Munshi, P. & Guru Row, T. N. (2006). Acta Cryst. B62, 612-626.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wilson, C. C., Shankland, N. & Florence, A. J. (1996). J. Chem. Soc. Faraday Trans. pp. 5051-5057.

organic compounds