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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 [sigma](C-C) = 0.006 Å
R = 0.045
wR = 0.127
Data-to-parameter ratio = 13.1
Details
Open access

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

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 Br...Br [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[Vaidya, V. P., Mahadevan, K. M., Shet Prakash, M., Sreenivas, S. & Shivananda, M. K. (2011). Res. J. Pharm. Biol. Chem. Sci. 2, 334-342.]).

[Scheme 1]

Experimental

Crystal data
  • C15H11BrO3

  • Mr = 319.15

  • Monoclinic, P 21 /c

  • a = 7.3108 (4) Å

  • b = 11.1545 (6) Å

  • c = 15.9752 (10) Å

  • [beta] = 100.921 (4)°

  • V = 1279.16 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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)[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.] Tmin = 0.467, Tmax = 0.595

  • 10028 measured reflections

  • 2249 independent reflections

  • 1699 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.127

  • S = 1.08

  • 2249 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.59 e Å-3

  • [Delta][rho]min = -0.54 e Å-3

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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 for Windows (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: 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.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Vaidya, V. P., Mahadevan, K. M., Shet Prakash, M., Sreenivas, S. & Shivananda, M. K. (2011). Res. J. Pharm. Biol. Chem. Sci. 2, 334-342.  [ChemPort]


Acta Cryst (2013). E69, o198  [ doi:10.1107/S160053681205204X ]

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