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Volume 69 
Part 5 
Page o671  
May 2013  

Received 27 March 2013
Accepted 1 April 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.107
Data-to-parameter ratio = 15.1
Details
Open access

Methyl 2-{2-[(2-methylphenoxy)methyl]phenyl}-2-oxoacetate

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and dDepartment of Chemistry, G. Madegowda Institute of Technology (GMIT), Bharathinagara 571 422, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C17H16O4, the dihedral angle between the benzene rings is 4.4 (2)°. In the crystal, weak C-H...O hydrogen bonds connect molecules along [001].

Related literature

The title compound is used in organic synthesis as a fungicide intermediate. For background to agrochemical fungicidal activity, see: Balba (2007[Balba, H. (2007). J. Environ. Sci. Health Part B, 42, 441-451.]); Cash & Cronan (2001[Cash, H. & Cronan, J. M. Jr (2001). US Patent Appl. WO2001-US964920010323.]); Ammermann et al. (2000[Ammermann, E., Lorenz, G., Schelberger, K., Mueller, B., Kirstgen, R. & Sauter, H. (2000). Proceedings of the Brighton Crop Protection Conference-Pests and Diseases, Vol. 2, pp. 541-548. Alton, Hampshire, England: BCPC Publications.]); For related structures see: Chopra et al. (2004[Chopra, D., Mohan, T. P., Rao, K. S. & Guru Row, T. N. (2004). Acta Cryst. E60, o2421-o2423.]); Kant et al. (2012[Kant, R., Gupta, V. K., Kapoor, K., Shripanavar, C. S. & Banerjee, K. (2012). Acta Cryst. E68, o2425.]). For standard bond lengths, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16O4

  • Mr = 284.30

  • Monoclinic, C 2/c

  • a = 31.6697 (11) Å

  • b = 7.5883 (2) Å

  • c = 12.5915 (6) Å

  • [beta] = 108.514 (4)°

  • V = 2869.4 (2) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.77 mm-1

  • T = 123 K

  • 0.47 × 0.34 × 0.14 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.921, Tmax = 1.000

  • 5506 measured reflections

  • 2897 independent reflections

  • 2551 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.107

  • S = 1.07

  • 2897 reflections

  • 192 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C17-H17A...O2i 0.98 2.44 3.3712 (18) 158
Symmetry code: (i) [x, -y, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5601 ).


Acknowledgements

MK thanks the UOM for research facilities. RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
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.
Ammermann, E., Lorenz, G., Schelberger, K., Mueller, B., Kirstgen, R. & Sauter, H. (2000). Proceedings of the Brighton Crop Protection Conference-Pests and Diseases, Vol. 2, pp. 541-548. Alton, Hampshire, England: BCPC Publications.
Balba, H. (2007). J. Environ. Sci. Health Part B, 42, 441-451.  [CrossRef] [ChemPort]
Cash, H. & Cronan, J. M. Jr (2001). US Patent Appl. WO2001-US964920010323.
Chopra, D., Mohan, T. P., Rao, K. S. & Guru Row, T. N. (2004). Acta Cryst. E60, o2421-o2423.  [CSD] [CrossRef] [ChemPort] [details]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Kant, R., Gupta, V. K., Kapoor, K., Shripanavar, C. S. & Banerjee, K. (2012). Acta Cryst. E68, o2425.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o671  [ doi:10.1107/S1600536813008878 ]

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