2-(3-Meth­oxy­phen­oxy)benzoic acid

Zhang, Z.-F.

doi:10.1107/S1600536811011019

Volume 67
Part 5
Page o1078
May 2011

Received 19 March 2011
Accepted 24 March 2011
Online 7 April 2011

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R = 0.062
wR = 0.133
Data-to-parameter ratio = 13.3
Details

2-(3-Methoxyphenoxy)benzoic acid

Zhi-Fang Zhang ^a ^*

^aSchool of Chemistry and Chemical Engineering, Yulin University, Yulin 719000, People's Republic of China
Correspondence e-mail: zhifang889@sohu.com

In the crystal structure of the title compound, C₁₄H₁₂O₄, the molecules form classical O-HO hydrogen-bonded carboxylic acid dimers. These dimers are linked by C-Hpi; interactions into a three-dimensional network. The benzene rings are oriented at a dihedral angle of 69.6 (3)°.

Related literature

For applications of the title compound, see: Jackson et al. (1993); Gapinski et al. (1990). For related structures, see: Shi et al. (2011); Raghunathan et al. (1982). For the synthesis of the title compound, see: Pellón et al. (1995). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₄H₁₂O₄
M_r = 244.24
Orthorhombic, P b c a
a = 14.309 (3) Å
b = 8.5330 (17) Å
c = 19.432 (4) Å
V = 2372.6 (8) Å³
Z = 8
Mo K radiation
= 0.10 mm^-1
T = 295 K
0.30 × 0.10 × 0.05 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.970, T_max = 0.995
4273 measured reflections
2175 independent reflections
1056 reflections with I > 2(I)
R_int = 0.093
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.062
wR(F²) = 0.133
S = 1.00
2175 reflections
163 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2-C7 ring.

D-HA	D-H	HA	DA	D-HA
O4-H4AO3ⁱ	0.82	1.82	2.633 (3)	173
C1-H1BCg1ⁱⁱ	0.96	2.89	3.784 (4)	155
Symmetry codes: (i) -x+2, -y, -z+2; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: CAD-4 Software (Enraf-Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5013 ).

Acknowledgements

The author gratefully acknowledges financial support from the Natural Science Foundation of the Education Department of Shaanxi Provincial Government (09JK844) and is grateful for support provided by the key industry problem plan of Yulin (gygg200807) and the special research projects of Yulin University (08YK17).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans.2, pp. S1-19.
Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Gapinski, D. M., Mallett, B. E., Froelich, L. L. & Jackson, W. T. (1990). J. Med. Chem. 33, 2798-2807.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Jackson, W. T., Boyd, R. J., Froelich, L. L., Gapinski, D. M., Mallett, B. E. & Sawyer, J. S. (1993). J. Med. Chem. 36, 1726-1734.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Pellón, R. F., Carrasco, R., Milián, V.& Rodes, L. (1995). Synth. Commun. 25, 1077-1083.
Raghunathan, S., Chandrasekhar, K. & Pattabhi, V. (1982). Acta Cryst. B38, 2536-2538.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shi, L., Zhang, Q., Xiao, Q., Wu, T. & Zhu, H.-J. (2011). Acta Cryst. E67, o748.

organic compounds