2-(Biphenyl-4-yl­oxy)acetic acid

Wang, E.-J.; Chen, G.-Y.

doi:10.1107/S1600536811002777

Volume 67
Part 2
Page o521
February 2011

Received 4 December 2010
Accepted 20 January 2011
Online 29 January 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.047
wR = 0.139
Data-to-parameter ratio = 14.9
Details

2-(Biphenyl-4-yloxy)acetic acid

En-Ju Wang ^a ^* and Guang-Ying Chen ^a

^aHainan Provincial Key Laboratory of Tropical Pharmaceutical Herb Chemistry, School of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, People's Republic of China
Correspondence e-mail: enjuwang@163.com

In the title compound, C₁₄H₁₂O₃, the phenyl and benzene rings make a dihedral angle of 47.51 (4)°. In the crystal, molecules are dimerized by double O-HO hydrogen bonds, forming centrosymmetric R₂²(8) ring motifs. The dimers are interlinked by C-H [pi] interactions into zigzag layers.

Related literature

For biological studies of biphenyl compounds, see: Kamoda et al. (2006); Kumar et al. (2008); Malamas et al. (2000). For related structures, see: Ali et al. (2008); Cao (2009); Margraf et al. (2009); Li et al. (2009); Charbonneau & Delugeard (1977); Brett et al. (1999). For hydrogen-bond motifs, see: Etter (1990).

Experimental

Crystal data

C₁₄H₁₂O₃
M_r = 228.24
Monoclinic, P 2₁ /n
a = 5.9118 (1) Å
b = 28.5786 (3) Å
c = 6.9017 (1) Å
= 109.631 (2)°
V = 1098.27 (3) Å³
Z = 4
Cu K radiation
= 0.79 mm^-1
T = 293 K
0.43 × 0.42 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.727, T_max = 0.742
11989 measured reflections
2306 independent reflections
2223 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.139
S = 1.12
2306 reflections
155 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C9-C14 ring.

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.82	1.81	2.6235 (13)	169
C12-H12Cgⁱⁱ	0.93	2.86	3.6392 (16)	142
Symmetry codes: (i) -x+1, -y, -z-1; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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: BH2330 ).

Acknowledgements

We are grateful for financial support from the Natural Science Foundation of Hainan Province (No. 808145)

References

Ali, Q., Shah, M. R. & VanDerveer, D. (2008). Acta Cryst. E64, o910.
Brett, T. J., Stezowski, J. J., Liu, S. & Coppens, P. (1999). Chem. Commun. pp. 551-552.
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cao, Y.-J. (2009). Acta Cryst. E65, o1851.
Charbonneau, G. P. & Delugeard, Y. (1977). Acta Cryst. B33, 1586-1588.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.
Kamoda, O., Anzai, K., Mizoguchi, J., Shiojiri, M., Yanagi, T., Nishino, T. & Kamiya, S. (2006). Antimicrob. Agents Chemother. 50, 3062-3069.
Kumar, H., Javed, S. A., Khan, S. A. & Amir, M. (2008). Eur. J. Med. Chem. 43, 2688-2698.
Li, F., Wang, W.-W., Ji, X., Cao, C.-C. & Zhu, D.-Y. (2009). Acta Cryst. E65, o244.
Malamas, M. S., Sredy, J., Moxham, C., Katz, A., Xu, W., McDevitt, R., Adebayo, F. O., Sawicki, D. R., Seestaller, L., Sullivan, D. & Taylor, J. R. (2000). J. Med. Chem. 43, 1293-1310.
Margraf, D., Schuetz, D., Prisner, T. F. & Bats, J. W. (2009). Acta Cryst. E65, o1784.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds