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Volume 69 
Part 5 
Page o775  
May 2013  

Received 1 April 2013
Accepted 14 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.033
wR = 0.076
Data-to-parameter ratio = 12.7
Details
Open access

Ethyl 3-amino-5-bromo-1-benzofuran-2-carboxylate

aDepartment of Chemistry, Kuvempu University, Jnana Sahyadri, Shankaraghatta 577 451, India,bDepartment of Biotechnology, PES Institute of Technology, BSK III Stg, Bangalore 560 085, India, and cDepartment of Chemistry, SSMRV College, 4th T Block, Jayanagar, Bangalore 560 041, India
Correspondence e-mail: girija.shivakumar@rediffmail.com

The title compound, C11H10BrNO3, is close to planar with the benzofuran unit and the ester group subtending a dihedral angle of 5.25 (2)°. The molecular structure features an intramolecular N-H...O interaction. In the crystal, N-H...O hydrogen bonds involving carboxyl O-atom acceptors generate a chain extending along [201].

Related literature

For the biological activity of benzofuran derivatives, see: Oter et al. (2007[Oter, O., Ertekin, K., Kirilmis, C., Koca, M. & Ahmedzade, M. (2007). Sens. Actuators B, 122, 450-456.]); Habermann et al. (1999[Habermann, J., Ley, S. V., Scicinski, J. J., Scott, J. S., Smits, R. & Thomas, A. W. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 2425-2427.]). For a similar structure, see: Karunakar et al. (2013[Karunakar, P., Krishnamurthy, V., Girija, C. R., Krishna, V., Vaidya, V. P. & Yamuna, A. J. (2013). Acta Cryst. E69, o342.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10BrNO3

  • Mr = 284.11

  • Monoclinic, P 21 /c

  • a = 5.775 (5) Å

  • b = 25.550 (2) Å

  • c = 7.640 (1) Å

  • [beta] = 98.292 (1)°

  • V = 1115.5 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.68 mm-1

  • T = 293 K

  • 0.20 × 0.15 × 0.10 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.591, Tmax = 0.732

  • 10542 measured reflections

  • 1957 independent reflections

  • 1658 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.076

  • S = 1.08

  • 1957 reflections

  • 154 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O2i 0.82 (2) 2.17 (2) 2.977 (4) 171 (3)
N1-H1B...O3 0.82 (2) 2.31 (3) 2.835 (4) 123 (3)
Symmetry code: (i) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); 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.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2255 ).


Acknowledgements

The authors thank Sophisticated Analytical Instrument Facility (SAIF), Indian Institute of Technology (IIT), Chennai, India, for the data collection. They also thank Dr K. M. Mahadevan, Department of Chemistry, and Dr V. Krishna, Department of Biotechnology of Kuvempu University, Jnana Sahyadri, Shankaraghatta, for their support.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Bruker (2004). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Habermann, J., Ley, S. V., Scicinski, J. J., Scott, J. S., Smits, R. & Thomas, A. W. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 2425-2427.  [CrossRef]
Karunakar, P., Krishnamurthy, V., Girija, C. R., Krishna, V., Vaidya, V. P. & Yamuna, A. J. (2013). Acta Cryst. E69, o342.  [CrossRef] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Oter, O., Ertekin, K., Kirilmis, C., Koca, M. & Ahmedzade, M. (2007). Sens. Actuators B, 122, 450-456.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o775  [ doi:10.1107/S1600536813010209 ]

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