N-Methyl-3,5-dinitro­benzamide

Deng, G.-M.; Wang, C.-R.; Chen, Z.; Zhang, H.-M.

doi:10.1107/S1600536811053888

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 (C-C) = 0.005 Å
R = 0.067
wR = 0.162
Data-to-parameter ratio = 11.8
Details

N-Methyl-3,5-dinitrobenzamide

Gui-Ming Deng,^a,^b Chao-Run Wang,^b Zhen Chen ^b and He-Ming Zhang ^a ^*

^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-HO 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). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₈H₇N₃O₅
M_r = 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 radiation
= 0.13 mm^-1
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.962, T_max = 0.987
4711 measured reflections
3402 independent reflections
1653 reflections with I > 2(I)
R_int = 0.0582
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.067
wR(F²) = 0.162
S = 0.96
3402 reflections
289 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3AO5ⁱ	0.86	2.06	2.900 (4)	165
N6-H6AO10ⁱ	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); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); 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.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds