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Volume 69 
Part 2 
Page o212  
February 2013  

Received 24 December 2012
Accepted 3 January 2013
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.058
wR = 0.146
Data-to-parameter ratio = 13.7
Details
Open access

4-(Octyloxy)phenyl 2-oxo-2H-chromene-3-carboxylate

aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India,bDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur 572 103, Karnataka, India, and cRaman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore 560 080, Karnataka, India
Correspondence e-mail: devarajegowda@yahoo.com

In the title compound, C24H26O5, the 2H-chromene ring system is essentially planar, with a maximum deviation of 0.029 (2) Å from the best-fit mean plane incorporating both rings. The dihedral angle between the 2H-chromene ring system and the benzene ring is 21.00 (1)°. In the crystal, pairs of C-H...O hydrogen bonds generate an R22(8) ring pattern. These contacts are bolstered by weaker bifurcated C-H...O hydrogen bonds.

Related literature

For general background to coumarin derivatives and their biological and technological applications, see: Georgieva et al. (2004[Georgieva, I., Mihaylov, T., Bauer, G. & Trendafilova, N. (2004). Chem. Phys. 300, 119-131.]); Creaven et al. (2005[Creaven, B. S., Egan, D. A., Kavanagh, K., McCann, M., Mahon, M., Noble, A., Thati, B. & Walsh, M. (2005). Polyhedron, 24, 949-957.]); Morita et al. (2005[Morita, Y., Tasaka, T., Yamaguchi, R., Okamoto, H. & Takenaka, S. (2005). Mol. Cryst. Liq. Cryst. 439, 209-220.]); Tian et al. (2003[Tian, Y., Akiyamab, E. & Nagase, Y. (2003). J. Mater. Chem. 13, 1253-1258.]); Iliopoulos et al. (2010[Iliopoulos, K., Krupka, O., Gindre, D. & Salle, M. (2010). J. Am. Chem. Soc. 132, 14343-14345.]); Hejchman et al. (2011[Hejchman, E. B., Konc, J. T., Maciejewska, D. & Kruszewska, H. (2011). Synth. Commun. 41, 2392-2402.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C24H26O5

  • Mr = 394.45

  • Monoclinic, P 21 /n

  • a = 14.464 (3) Å

  • b = 6.7548 (15) Å

  • c = 21.381 (5) Å

  • [beta] = 91.663 (8)°

  • V = 2088.0 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.29 × 0.25 × 0.21 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.]) Tmin = 0.975, Tmax = 0.982

  • 22609 measured reflections

  • 3615 independent reflections

  • 1926 reflections with I > 2[sigma](I)

  • Rint = 0.084

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.146

  • S = 0.94

  • 3615 reflections

  • 264 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...O1i 0.93 2.59 3.513 (4) 174
C9-H9...O2i 0.93 2.51 3.420 (3) 167
C16-H16...O2i 0.93 2.71 3.551 (3) 151
C16-H16...O3i 0.93 2.63 3.338 (3) 133
Symmetry code: (i) x, y+1, 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: SJ5291 ).


Acknowledgements

The authors thank Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, and P. A. Suchetan, Department of Studies and Research in Chemistry, U·C.S. Tumkur University, Tumkur, for their help and suggestions.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Creaven, B. S., Egan, D. A., Kavanagh, K., McCann, M., Mahon, M., Noble, A., Thati, B. & Walsh, M. (2005). Polyhedron, 24, 949-957.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Georgieva, I., Mihaylov, T., Bauer, G. & Trendafilova, N. (2004). Chem. Phys. 300, 119-131.  [ISI] [CrossRef] [ChemPort]
Hejchman, E. B., Konc, J. T., Maciejewska, D. & Kruszewska, H. (2011). Synth. Commun. 41, 2392-2402.  [ISI] [CrossRef] [ChemPort]
Iliopoulos, K., Krupka, O., Gindre, D. & Salle, M. (2010). J. Am. Chem. Soc. 132, 14343-14345.  [ISI] [CrossRef] [ChemPort] [PubMed]
Morita, Y., Tasaka, T., Yamaguchi, R., Okamoto, H. & Takenaka, S. (2005). Mol. Cryst. Liq. Cryst. 439, 209-220.  [CrossRef]
Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tian, Y., Akiyamab, E. & Nagase, Y. (2003). J. Mater. Chem. 13, 1253-1258.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o212  [ doi:10.1107/S1600536813000214 ]

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