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

Palakshamurthy, B.S.; Sreenivasa, S.; Srinivasa, H.T.; Roopashree, K.R.; Devarajegowda, H.C.

doi:10.1107/S1600536813000214

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 (C-C) = 0.004 Å
R = 0.058
wR = 0.146
Data-to-parameter ratio = 13.7
Details

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

B. S. Palakshamurthy,^a S. Sreenivasa,^b H. T. Srinivasa,^c K. R. Roopashree ^a and H. C. Devarajegowda ^a ^*

^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-HO hydrogen bonds generate an R₂²(8) ring pattern. These contacts are bolstered by weaker bifurcated C-HO hydrogen bonds.

Related literature

For general background to coumarin derivatives and their biological and technological applications, see: Georgieva et al. (2004); Creaven et al. (2005); Morita et al. (2005); Tian et al. (2003); Iliopoulos et al. (2010); Hejchman et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₄H₂₆O₅
M_r = 394.45
Monoclinic, P 2₁ /n
a = 14.464 (3) Å
b = 6.7548 (15) Å
c = 21.381 (5) Å
= 91.663 (8)°
V = 2088.0 (8) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.975, T_max = 0.982
22609 measured reflections
3615 independent reflections
1926 reflections with I > 2(I)
R_int = 0.084

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.146
S = 0.94
3615 reflections
264 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4O1ⁱ	0.93	2.59	3.513 (4)	174
C9-H9O2ⁱ	0.93	2.51	3.420 (3)	167
C16-H16O2ⁱ	0.93	2.71	3.551 (3)	151
C16-H16O3ⁱ	0.93	2.63	3.338 (3)	133
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); 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.
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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Georgieva, I., Mihaylov, T., Bauer, G. & Trendafilova, N. (2004). Chem. Phys. 300, 119-131.
Hejchman, E. B., Konc, J. T., Maciejewska, D. & Kruszewska, H. (2011). Synth. Commun. 41, 2392-2402.
Iliopoulos, K., Krupka, O., Gindre, D. & Salle, M. (2010). J. Am. Chem. Soc. 132, 14343-14345.
Morita, Y., Tasaka, T., Yamaguchi, R., Okamoto, H. & Takenaka, S. (2005). Mol. Cryst. Liq. Cryst. 439, 209-220.
Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tian, Y., Akiyamab, E. & Nagase, Y. (2003). J. Mater. Chem. 13, 1253-1258.

organic compounds