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Volume 69 
Part 4 
Page o509  
April 2013  

Received 26 February 2013
Accepted 4 March 2013
Online 9 March 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.080
Data-to-parameter ratio = 18.6
Details
Open access

2,4-Dichlorobenzyl 2-methoxybenzoate

aNational Institute of Technology-Karnataka, Department of Chemistry, Surathkal, Mangalore 575 025, India, and bNelson 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

In the title compound, C15H12Cl2O3, the aromatic rings make a dihedral angle of 10.78 (4)°. In the molecule, there is a short C-H...O contact. In the crystal, C-H...O contacts connect the molecules into C(7)C(8) chains along the b axis. The shortest intercentroid distance between two benzoic acid aromatic systems is 3.7416 (8) Å.

Related literature

For pharmacological properties of phenyl benzoates, see: Oxford et al. (2005[Oxford, J. S., Lambkin, R., Gibb, I., Balasingam, S., Chan, C. & Catchpole, A. (2005). Antivir. Chem. Chemother. 16, 129-134.]); Ostergaard (1994[Ostergaard, E. (1994). Acta Odontol. Scand. 52, 335-345.]). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12Cl2O3

  • Mr = 311.15

  • Monoclinic, P 21 /c

  • a = 12.1816 (5) Å

  • b = 15.2481 (6) Å

  • c = 7.4207 (4) Å

  • [beta] = 99.299 (2)°

  • V = 1360.25 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.48 mm-1

  • T = 200 K

  • 0.38 × 0.37 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.847, Tmax = 0.982

  • 12933 measured reflections

  • 3379 independent reflections

  • 2868 reflections with I > 2[sigma](I)

  • Rint = 0.015

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.080

  • S = 1.03

  • 3379 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3A...O2i 0.98 2.59 3.5433 (18) 165
C15-H15...O2i 0.95 2.51 3.3945 (15) 154
C16-H16...O3 0.95 2.48 3.3989 (15) 163
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5318 ).


Acknowledgements

AMI thanks Professor Swapan Bhattacharya, Director of the National Institute of Technology Karnataka, Surathkal, India, for encouragement and for providing research facilities. He also thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Ostergaard, E. (1994). Acta Odontol. Scand. 52, 335-345.  [ChemPort] [PubMed] [ISI]
Oxford, J. S., Lambkin, R., Gibb, I., Balasingam, S., Chan, C. & Catchpole, A. (2005). Antivir. Chem. Chemother. 16, 129-134.  [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o509  [ doi:10.1107/S1600536813006156 ]

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