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Volume 68 
Part 1 
Page o209  
January 2012  

Received 12 December 2011
Accepted 14 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.067
wR = 0.162
Data-to-parameter ratio = 11.8
Details
Open access

N-Methyl-3,5-dinitrobenzamide

aMOE Key Laboratory of Laser Life Science & Institute of Laser Life Science, College of Biophotonics, South China Normal University, Guangzhou 510631, People's Republic of China, and bThe First Affiliated Hospital of Hunan University of Chinese Medicine, Changsha 410007, People's Republic of China
Correspondence e-mail: zhang_heming88@yahoo.com.cn

The asymmetric unit of the title compound, C8H7N3O5, contains two independent molecules in which the amide plane is oriented at dihedral angles of 29.82 (2) and 31.17 (2)° with respect to the benzene ring. In the crystal, molecules are connected via intermolecular N-H...O hydrogen bonds, forming chains running along the b axis.

Related literature

For general background to the biological activity of benzamide derivatives, see: Lee et al. (2009[Lee, S., Song, K. H., Choe, J., Ju, J. & Jo, Y. (2009). J. Org. Chem. 74, 6358-6361.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C8H7N3O5

  • Mr = 225.16

  • Orthorhombic, P b c a

  • a = 10.716 (2) Å

  • b = 10.057 (2) Å

  • c = 36.101 (7) Å

  • V = 3890.6 (13) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.962, Tmax = 0.987

  • 4711 measured reflections

  • 3402 independent reflections

  • 1653 reflections with I > 2[sigma](I)

  • Rint = 0.0582

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.067

  • wR(F2) = 0.162

  • S = 0.96

  • 3402 reflections

  • 289 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...O5i 0.86 2.06 2.900 (4) 165
N6-H6A...O10i 0.86 2.12 2.955 (4) 164
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z].

Data collection: CAD-4 Software (Enraf-Nonius, 1985[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5409 ).


Acknowledgements

This work was supported by the National Natural Science Foundation of China (30940094) and the Science Foundation for Excellent Youth Scholars of the Education Commission of Hunan Province, China (10B077).

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.
Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Lee, S., Song, K. H., Choe, J., Ju, J. & Jo, Y. (2009). J. Org. Chem. 74, 6358-6361.  [PubMed]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o209  [ doi:10.1107/S1600536811053888 ]

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