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Volume 68 
Part 1 
Page o129  
January 2012  

Received 28 November 2011
Accepted 9 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.049
wR = 0.174
Data-to-parameter ratio = 11.8
Details
Open access

Ethyl 2-(3,5-dinitrobenzamido)benzoate

aDepartment of Chemistry, Research Complex, Allama Iqbal Open Unicversity, Islamabad 44000, Pakistan,bNational Engineering & Scientific Commission, PO Box 2801, Islamabad, Pakistan, and cDepartment of Chemistry, The University of Hong Kong, Pokfulam Road, Pokfulam, Hong Kong SAR, People's Republic of China
Correspondence e-mail: Sohail262001@yahoo.com

The title molecule, C16H13N3O7, is slightly twisted, with the dihedral angle between the two benzene ring planes being 17.4 (1)°. An intramolecular N-H...O hydrogen bond is observed. In the crystal, weak C-H...O hydrogen bonds link the molecules into chains along the b axis.

Related literature

For background to the biological activity of N-substituted benzamides and their use in synthesis, see: Saeed et al. (2011a[Saeed, S., Jasinski, J. P. & Butcher, R. J. (2011a). Acta Cryst. E67, o279.],b[Saeed, S., Rashid, N., Ng, S. W. & Tiekink, E. R. T. (2011b). Acta Cryst. E67, o1194.]). For the structures of related chlorophenylbenzamides, see: Gowda et al. (2007a[Gowda, B. T., Sowmya, B. P., Kozísek, J., Tokarcík, M. & Fuess, H. (2007a). Acta Cryst. E63, o2906.],b[Gowda, B. T., Sowmya, B. P., Tokarcík, M., Kozísek, J. & Fuess, H. (2007b). Acta Cryst. E63, o3326.],c[Gowda, B. T., Sowmya, B. P., Tokarcík, M., Kozísek, J. & Fuess, H. (2007c). Acta Cryst. E63, o3365.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 341, 555-1573.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For ortho-hydrogen steric hindrance, see: Karle & Brockway (1944[Karle, I. L. & Brockway, L. O. (1944). J. Am. Chem. Soc. 66, 1974-1979.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13N3O7

  • Mr = 359.29

  • Monoclinic, P 21 /c

  • a = 12.4662 (4) Å

  • b = 17.7213 (5) Å

  • c = 7.4352 (2) Å

  • [beta] = 96.658 (2)°

  • V = 1631.49 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 296 K

  • 0.52 × 0.30 × 0.26 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.942, Tmax = 0.970

  • 16092 measured reflections

  • 2808 independent reflections

  • 1961 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.174

  • S = 1.11

  • 2808 reflections

  • 237 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2 0.86 1.92 2.641 (3) 140
C16-H16A...O3i 0.96 2.55 3.402 (4) 148
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FK2047 ).


Acknowledgements

Dr. Wesley T. K. Chan, Professor Z. Y. Zhou, and the Hong Kong Polytechnic University are sincerely thanked for helping to collect the X-ray data.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 341, 555-1573.
Bruker (2007). APEX2 and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA.
Gowda, B. T., Sowmya, B. P., Kozísek, J., Tokarcík, M. & Fuess, H. (2007a). Acta Cryst. E63, o2906.  [CSD] [CrossRef] [details]
Gowda, B. T., Sowmya, B. P., Tokarcík, M., Kozísek, J. & Fuess, H. (2007b). Acta Cryst. E63, o3326.  [CSD] [CrossRef] [details]
Gowda, B. T., Sowmya, B. P., Tokarcík, M., Kozísek, J. & Fuess, H. (2007c). Acta Cryst. E63, o3365.  [CSD] [CrossRef] [details]
Karle, I. L. & Brockway, L. O. (1944). J. Am. Chem. Soc. 66, 1974-1979.  [CrossRef] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Saeed, S., Jasinski, J. P. & Butcher, R. J. (2011a). Acta Cryst. E67, o279.  [CSD] [CrossRef] [details]
Saeed, S., Rashid, N., Ng, S. W. & Tiekink, E. R. T. (2011b). Acta Cryst. E67, o1194.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o129  [ doi:10.1107/S1600536811053074 ]

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