Ethyl 5-bromo­naphtho­[2,1-b]furan-2-carboxyl­ate

Shet Prakash, M.; Suchetan, P.A.; Mahadevan, K.M.; Vaidya, V.P.; Velumurgan, D.; Palakshamurthy, B.S.

doi:10.1107/S160053681205204X

Volume 69
Part 2
Page o198
February 2013

Received 23 December 2012
Accepted 29 December 2012
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R = 0.045
wR = 0.127
Data-to-parameter ratio = 13.1
Details

Ethyl 5-bromonaphtho[2,1-b]furan-2-carboxylate

M. Shet Prakash,^a P. A. Suchetan,^a K. M. Mahadevan,^b V. P. Vaidya,^b D. Velumurgan ^c and B. S. Palakshamurthy ^d ^*

^aDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India,^bDepartment of Chemistry, Kuvempu University, Shankaraghatta Shimoga, Karnataka, India,^cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^dDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
Correspondence e-mail: palaksha.bspm@gmail.com

In the title compound, C₁₅H₁₁BrO₃, the dihedral angle between the naphthofuran ring system (r.m.s. deviation = 0.022 Å) and the side chain is 4.50 (2)°. In the crystal, short BrBr [3.4435 (7) Å] contacts propagating along [010] in a zigzag manner and weak [pi] - [pi] interactions [shortest centroid-centroid separation = 3.573 (2) Å] directedalong [100] are observed.

Related literature

For background to the biological activity of naphthofuran derivatives, see: Vaidya et al. (2011).

Experimental

Crystal data

C₁₅H₁₁BrO₃
M_r = 319.15
Monoclinic, P 2₁ /c
a = 7.3108 (4) Å
b = 11.1545 (6) Å
c = 15.9752 (10) Å
= 100.921 (4)°
V = 1279.16 (13) Å³
Z = 4
Mo K radiation
= 3.21 mm^-1
T = 298 K
0.28 × 0.24 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.467, T_max = 0.595
10028 measured reflections
2249 independent reflections
1699 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.127
S = 1.08
2249 reflections
172 parameters
H-atom parameters constrained
_max = 0.59 e Å^-3
_min = -0.54 e Å^-3

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (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: HB7019 ).

Acknowledgements

BSPM thanks Dr H. C. Devarajegowda, Department of Physics, Yuvarajas College (constituent), University of Mysore and T. Srinivasan, Centre of Advanced Study in Crystallography and Biophysics, University of Madras Guindy Campus, Chennai for their support.

References

Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vaidya, V. P., Mahadevan, K. M., Shet Prakash, M., Sreenivas, S. & Shivananda, M. K. (2011). Res. J. Pharm. Biol. Chem. Sci. 2, 334-342.

organic compounds