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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 [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.129
Data-to-parameter ratio = 12.9
Details
Open access

Methyl 4-benzyloxy-2-hydroxybenzoate

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 Ca-Cm-O-Ca (a = aromatic and m = methylene) torsion angle is 172.6 (3)° and an intramolecular O-H...O hydrogen bond generates an S(6) ring. In the crystal, molecules are linked by C-H...O 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[Pifferi, G., Gaviraghi, G., Pinza, M. & Ventura, P. J. (1977). J. Heterocycl. Chem. 14, 1257-1259.]); Ghosh et al. (2008[Ghosh, S., Li, X. Q., Stepanenko, V. & Wurthner, F. (2008). Chem. Eur. J. 14, 11343-11357.]). For related structures and further synthetic details, see: Tangdenpaisal et al. (2009[Tangdenpaisal, K., Sualek, S., Ruchirawat, S. & Ploypradith, P. (2009). Tetrahedron, 65, 4316-4325.]); Kashi et al. (2010[Kashi, H. K. A., Palakshamurthy, B. S., VinduVahini, M., Srinivasa, H. T. & Devarajegowda, H. C. (2010). Acta Cryst. E66, o2126.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14O4

  • Mr = 258.26

  • Triclinic, [P \overline 1]

  • a = 5.7731 (10) Å

  • b = 7.9855 (14) Å

  • c = 14.046 (3) Å

  • [alpha] = 89.490 (6)°

  • [beta] = 80.111 (5)°

  • [gamma] = 87.210 (6)°

  • V = 637.16 (19) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.977, Tmax = 0.983

  • 12770 measured reflections

  • 2231 independent reflections

  • 1679 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.129

  • S = 1.07

  • 2231 reflections

  • 173 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5-C10 ring.

D-H...A D-H H...A D...A D-H...A
O2-H2...O3 0.82 1.89 2.6133 (17) 146
C19-H19C...O2i 0.96 2.54 3.469 (3) 163
C11-H11A...Cg1ii 0.97 2.78 3.5991 (19) 143
C13-H13...Cg1iii 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[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012)[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]; 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.  [ISI] [CrossRef] [ChemPort] [details]
Ghosh, S., Li, X. Q., Stepanenko, V. & Wurthner, F. (2008). Chem. Eur. J. 14, 11343-11357.  [CrossRef] [PubMed] [ChemPort]
Kashi, H. K. A., Palakshamurthy, B. S., VinduVahini, M., Srinivasa, H. T. & Devarajegowda, H. C. (2010). Acta Cryst. E66, o2126.  [CSD] [CrossRef] [details]
Pifferi, G., Gaviraghi, G., Pinza, M. & Ventura, P. J. (1977). J. Heterocycl. Chem. 14, 1257-1259.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tangdenpaisal, K., Sualek, S., Ruchirawat, S. & Ploypradith, P. (2009). Tetrahedron, 65, 4316-4325.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3382  [ doi:10.1107/S1600536812046491 ]

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