Methyl 4-benz­yloxy-2-hy­droxy­benzoate

Palakshamurthy, B.S.; Srinivasa, H.T.; Kumar, V.; Sreenivasa, S.; Devarajegowda, H.C.

doi:10.1107/S1600536812046491

Volume 68
Part 12
Page o3382
December 2012

Received 4 November 2012
Accepted 10 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.042
wR = 0.129
Data-to-parameter ratio = 12.9
Details

Methyl 4-benzyloxy-2-hydroxybenzoate

B. S. Palakshamurthy,^a H. T. Srinivasa,^b Vijith Kumar,^c S. Sreenivasa ^d and H. C. Devarajegowda ^a ^*

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India,^bRaman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore 560 080, Karnataka, India,^cSoild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^dDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur 572 103, Karnataka, India
Correspondence e-mail: devarajegowda@yahoo.com

In the title compound, C₁₅H₁₄O₄, the dihedral angle between the benzene rings is 67.18 (8)°. The C_a-C_m-O-C_a (a = aromatic and m = methylene) torsion angle is 172.6 (3)° and an intramolecular O-HO hydrogen bond generates an S(6) ring. In the crystal, molecules are linked by C-HO hydrogen bonds into zigzag chains propagating in [001] and C-H [pi] interactions also occur.

Related literature

For general background to benzyloxybenzoates, see: Pifferi et al. (1977); Ghosh et al. (2008). For related structures and further synthetic details, see: Tangdenpaisal et al. (2009); Kashi et al. (2010).

Experimental

Crystal data

C₁₅H₁₄O₄
M_r = 258.26
Triclinic, $[P \overline 1]$
a = 5.7731 (10) Å
b = 7.9855 (14) Å
c = 14.046 (3) Å
= 89.490 (6)°
= 80.111 (5)°
= 87.210 (6)°
V = 637.16 (19) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 293 K
0.24 × 0.22 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) T_min = 0.977, T_max = 0.983
12770 measured reflections
2231 independent reflections
1679 reflections with I > 2(I)
R_int = 0.053

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.129
S = 1.07
2231 reflections
173 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5-C10 ring.

D-HA	D-H	HA	DA	D-HA
O2-H2O3	0.82	1.89	2.6133 (17)	146
C19-H19CO2ⁱ	0.96	2.54	3.469 (3)	163
C11-H11ACg1ⁱⁱ	0.97	2.78	3.5991 (19)	143
C13-H13Cg1ⁱⁱⁱ	0.93	2.95	3.7324 (19)	142
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z; (iii) -x+1, -y, -z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6982 ).

Acknowledgements

The authors thank to Professor T. N. Guru Row, Soild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore and G. B. Sadananda, Department of Studies and Research in Physics, U.C.S. Tumkur University, Tumkur, for their help and suggestions.

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Ghosh, S., Li, X. Q., Stepanenko, V. & Wurthner, F. (2008). Chem. Eur. J. 14, 11343-11357.
Kashi, H. K. A., Palakshamurthy, B. S., VinduVahini, M., Srinivasa, H. T. & Devarajegowda, H. C. (2010). Acta Cryst. E66, o2126.
Pifferi, G., Gaviraghi, G., Pinza, M. & Ventura, P. J. (1977). J. Heterocycl. Chem. 14, 1257-1259.
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tangdenpaisal, K., Sualek, S., Ruchirawat, S. & Ploypradith, P. (2009). Tetrahedron, 65, 4316-4325.

organic compounds