Ethyl 4-(2-fur­yl)-2-oxochroman-3-carboxyl­ate

Prabhakar, M.; Reddy, J.S.N.; Kumar, N.R.; Ganesh, S.V.; Solomon, K.A.

doi:10.1107/S1600536810016193

Volume 66
Part 6
Page o1310
June 2010

Received 15 April 2010
Accepted 3 May 2010
Online 12 May 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.042
wR = 0.111
Data-to-parameter ratio = 11.9
Details

Ethyl 4-(2-furyl)-2-oxochroman-3-carboxylate

Maddela Prabhakar,^a J. S. N. Reddy,^a N. Ravi Kumar,^a S. Viswanadha Ganesh ^a and K. Anand Solomon ^a ^*

^aInstitute of Life Sciences, University of Hyderabad Campus, Hyderabad 500 046, India
Correspondence e-mail: anandsolomonk@ilsresearch.org

The title compound, C₁₆H₁₄O₅, was prepared from the reaction of 3-carbethoxycoumarin with furan in the presence of AlCl₃ as catalyst. In the crystal, intermolecular C-HO hydrogen-bonding interactions between four molecules lead to a tetramer in the unit cell. The furan ring is antiperiplanar [C-C-C-O = 167.9 (13)°] and the ethoxycarbonyl group is (-)anticlinal [C-C-C-O = -128.6 (14)°] to the lactone ring.

Related literature

For the medicinal and biological activity of coumarins and their derivatives, see: Borges et al. (2005); Kontogiorgis & Hadjipavlou-Litina (2005); Gursoy & Karali (2003); Prabhakar et al. (2010). For the assignment of conformations and the orientation of the substituents, see: Nardelli (1983, 1995); Klyne & Prelog (1960).

Experimental

Crystal data

C₁₆H₁₄O₅
M_r = 286.27
Monoclinic, P 2₁ /c
a = 10.393 (3) Å
b = 8.459 (3) Å
c = 15.819 (5) Å
= 95.464 (5)°
V = 1384.5 (8) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 298 K
0.34 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003) T_min = 0.966, T_max = 0.980
13767 measured reflections
2711 independent reflections
2099 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.111
S = 1.04
2711 reflections
227 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.18 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3O3ⁱ	0.972 (15)	2.696 (15)	3.576 (2)	150.8 (11)
C16-H16BO2ⁱⁱ	0.96	2.70	3.549 (3)	148
C16-H16AO2ⁱⁱⁱ	0.96	2.96	3.841 (3)	153
C8-H8O3^iv	0.96 (2)	2.94 (2)	3.611 (3)	128.2 (15)
C11-H11O4^v	0.93 (2)	2.73 (2)	3.501 (3)	140.9 (17)
C13-H13O2^vi	1.01 (2)	2.54 (2)	3.456 (3)	151.0 (17)
C12-H12O4^vii	0.95 (2)	2.74 (2)	3.478 (3)	134.9 (16)
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) x, y-1, z; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) -x+2, -y+2, -z+2; (v) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ ; (vii) x, y+1, z.

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2028 ).

Acknowledgements

We thank the Director, Institute of Life Sciences, for support and also the Dean, School of Chemistry, University of Hyderabad, for the X-ray crystallographic data.

References

Borges, F., Roleira, F., Milhazes, N., Santana, L. & Uriarte, E. (2005). Curr. Med. Chem. 12, 887-916.
Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Gursoy, A. & &Karali, N. (2003). Turk. J. Chem. 27, 545-551.
Klyne, W. & Prelog, V. (1960). Experientia, 16, 521-568.
Kontogiorgis, C. A. & Hadjipavlou-Litina, D. J. (2005). J. Med. Chem. 48, 6400-6408.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Prabhakar, M., Narendar Reddy, G., Srinu, G., Manjulatha, K., Venkata Prasad, J., Pramod Kumar, S., Srinivas, O., Iqbal, J. & Anil Kumar, K. (2010). Synlett, pp. 947-951.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds