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Volume 69 
Part 4 
Page o502  
April 2013  

Received 20 February 2013
Accepted 26 February 2013
Online 6 March 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.049
wR = 0.114
Data-to-parameter ratio = 20.4
Details
Open access

Ethyl 2-[(2-oxo-2H-chromen-7-yl)oxy]acetate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and cDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C13H12O5, the mean plane of the 2H-chromene ring system (r.m.s deviation = 0.026 Å) forms a dihedral angle of 81.71 (6)° with the mean plane of ethyl 2-hydroxyacetate moiety (r.m.s deviation = 0.034 Å). In the crystal, C-H...O hydrogen bonds result in the formation of zigzag layers parallel to the bc plane.

Related literature

For general background to and the high emission quantum yield, photo stability and good solubility in common solvents of coumarin derivatives, see: Xie et al. (2012[Xie, L., Chen, Y., Wu, W., Guo, H., Zhao, J. & Yu, X. (2012). Dyes Pigm. 92, 1361-1369.]); Liu et al. (2012[Liu, X., Cole, J. M., Waddell, P. G., Lin, T. C., Radia, J. & Zeidler, A. (2012). J. Phys. Chem. A, 116, 727-737.]). For standard bond-length data, 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.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]). For related structures, see: Arshad et al. (2010a[Arshad, A., Osman, H., Lam, C. K., Quah, C. K. & Fun, H.-K. (2010a). Acta Cryst. E66, o1632-o1633.],b[Arshad, A., Osman, H., Lam, C. K., Quah, C. K. & Fun, H.-K. (2010b). Acta Cryst. E66, o1446-o1447.]).

[Scheme 1]

Experimental

Crystal data
  • C13H12O5

  • Mr = 248.23

  • Monoclinic, P 21 /c

  • a = 8.1435 (2) Å

  • b = 16.4887 (4) Å

  • c = 10.5506 (3) Å

  • [beta] = 125.882 (2)°

  • V = 1147.84 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 100 K

  • 0.31 × 0.24 × 0.11 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.966, Tmax = 0.988

  • 12656 measured reflections

  • 3344 independent reflections

  • 2308 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.114

  • S = 1.04

  • 3344 reflections

  • 164 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1A...O2i 0.93 2.38 3.2913 (19) 166
C5-H5A...O5ii 0.93 2.55 3.373 (2) 147
C10-H10B...O2i 0.97 2.48 3.353 (2) 149
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) -x, -y+2, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: RZ5046 ).


Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the RUC grant (Structure Determination of 50 kDa Outer Membrane Proteins from S. typhi by X-ray Protein Crystallography, No. 1001/PSKBP/8630013) and APEX DE2012 grant (No.1002/PFIZIK/910323). The authors also thank the CSIR and DST, Government of India, for financial support.

References

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.
Arshad, A., Osman, H., Lam, C. K., Quah, C. K. & Fun, H.-K. (2010a). Acta Cryst. E66, o1632-o1633.  [CSD] [CrossRef] [details]
Arshad, A., Osman, H., Lam, C. K., Quah, C. K. & Fun, H.-K. (2010b). Acta Cryst. E66, o1446-o1447.  [CSD] [CrossRef] [details]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Liu, X., Cole, J. M., Waddell, P. G., Lin, T. C., Radia, J. & Zeidler, A. (2012). J. Phys. Chem. A, 116, 727-737.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Xie, L., Chen, Y., Wu, W., Guo, H., Zhao, J. & Yu, X. (2012). Dyes Pigm. 92, 1361-1369.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o502  [ doi:10.1107/S1600536813005539 ]

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