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Volume 69 
Part 10 
Page o1592  
October 2013  

Received 17 September 2013
Accepted 23 September 2013
Online 28 September 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.099
Data-to-parameter ratio = 14.4
Details
Open access

N-(2-Nitrophenyl)furan-2-carboxamide

aDepartamento de Química - Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia,bWestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland, and cInstituto de Química de São Carlos, IFSC, Universidade de São Paulo, USP, São Carlos, SP, Brazil
Correspondence e-mail: rodimo26@yahoo.es

In the title furancarboxamide derivative, C11H8N2O4, the benzene and furan rings are rotated from the mean plane of the central fragment by 2.68 (5) and 7.03 (4)°, respectively. The nitro group forms a dihedral angle of 10.15 (5)° with the adjacent benzene ring. In the crystal, molecules are linked by weak C-H...O interactions, forming helical chains running along [010].

Related literature

For similar furancarboxamide compounds, see: Pavlovic et al. (2004)[Pavlovic, G., Tralic-Kulenovic, V. & Popovic, Z. (2004). Acta Cryst. E60, o631-o633.] and for similar 2-nitrophenylamino compounds, see: Glidewell et al. (2004[Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2004). Acta Cryst. C60, o120-o124.]). For hydrogen-bonding information, see: Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]). For hydrogen-bond motifs, see: Etter et al. (1990[Etter, M. (1990). Acc. Chem. Res. 23, 120-126.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C11H8N2O4

  • Mr = 232.19

  • Monoclinic, P 21 /c

  • a = 7.0380 (5) Å

  • b = 12.8072 (9) Å

  • c = 11.3701 (9) Å

  • [beta] = 97.819 (6)°

  • V = 1015.34 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 123 K

  • 0.35 × 0.33 × 0.25 mm

Data collection
  • Oxford Diffraction Xcalibur E diffractometer

  • 4090 measured reflections

  • 2649 independent reflections

  • 1859 reflections with I > 2[sigma](I)

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.099

  • S = 1.04

  • 2649 reflections

  • 158 parameters

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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O2i 0.95 2.55 3.3857 (18) 146
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.]) 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2129 ).


Acknowledgements

RMF thanks the Universidad del Valle, Colombia, for partial financial support.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
Etter, M. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2004). Acta Cryst. C60, o120-o124.  [CrossRef] [IUCr Journals]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [IUCr Journals]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Pavlovic, G., Tralic-Kulenovic, V. & Popovic, Z. (2004). Acta Cryst. E60, o631-o633.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1592  [ doi:10.1107/S1600536813026202 ]

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