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Volume 69 
Part 3 
Page o342  
March 2013  

Received 17 January 2013
Accepted 29 January 2013
Online 6 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.038
wR = 0.102
Data-to-parameter ratio = 11.9
Details
Open access

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

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

In the title compound, C14H14BrNO5, the ester group is disordered [occupancy ratio 0.52 (2):0.48 (2)]. The major component is nearly coplanar with the benzofuran plane, subtending a dihedral angle of 7.84 (2)°, while the amide group is twisted out of the benzofuran plane making a dihedral angle of 39.69 (2)°. An intramolecular N-H...O hydrogen bond occurs. In the crystal, pairs of weak C-H...O hydrogen bonds link the molecules into inversion dimers, which are further linked via strong N-H...O hydrogen bonds, generating a zigzag chain extending along [100].

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, 17, 2425-2427.]).

[Scheme 1]

Experimental

Crystal data
  • C14H14BrNO5

  • Mr = 356.17

  • Monoclinic, P 21 /c

  • a = 14.1960 (7) Å

  • b = 4.8050 (2) Å

  • c = 22.128 (1) Å

  • [beta] = 90.653 (1)°

  • V = 1509.29 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.74 mm-1

  • T = 293 K

  • 0.35 × 0.30 × 0.30 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 = 0.426, Tmax = 0.500

  • 14023 measured reflections

  • 2660 independent reflections

  • 1969 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.102

  • S = 1.07

  • 2660 reflections

  • 223 parameters

  • 73 restraints

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

  • [Delta][rho]max = 0.62 e Å-3

  • [Delta][rho]min = -0.60 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O4 0.89 (1) 2.40 (3) 2.909 (4) 117 (3)
N1-H1...O2i 0.89 (1) 2.27 (2) 3.021 (4) 142 (3)
C10-H10B...O4ii 0.97 (1) 2.66 (2) 3.427 (4) 135 (3)
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y-1, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and 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: HG5285 ).


Acknowledgements

The authors thank the Sophisticated Analytical Instrument Facility (SAIF), Indian Institute of Technology (IIT), Chennai, India, for the data collection. PK and CRG also thank the Rashtriya Sikshana Samithi Trust (RSST) and the Principal, Sri Sivananda Sarma Memorial Rashtriya Vidyalaya (SSMRV) College, Bangalore, for their constant support and encouragement in carrying out this work.

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, 17, 2425-2427.  [CrossRef]
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]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o342  [ doi:10.1107/S1600536813002997 ]

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