2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl N-methyl­carbamate

Duan, G.-Y.; Xia, C.-C.; Xiao, Y.-L.

doi:10.1107/S1600536808041676

Volume 65
Part 1
Page o116
January 2009

Received 30 November 2008
Accepted 9 December 2008
Online 13 December 2008

Key indicators
Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.002 Å
R = 0.031
wR = 0.089
Data-to-parameter ratio = 13.2
Details

2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl N-methylcarbamate

Gui-Yun Duan,^a ^* Cheng-Cai Xia ^a and Yu-Liang Xiao ^a

^aCollege of Pharmaceutical Sciences, Taishan Medical University, Tai'an 271016, People's Republic of China
Correspondence e-mail: duanguiyun@yahoo.cn

In the title compound, C₈H₁₂N₄O₄, the essentially planar methylcarbamoyloxymethyl group [maximum deviation 0.038 (3) Å] and the imidazole ring make a dihedral angle of 48.47 (3)°. The crystal packing is stabilized by intermolecular N-HN and C-HO hydrogen bonds, which link the molecules into infinite ribbons running along the a axis, and by weak [pi] - [pi] stacking interactions [centroid-centroid distance = 3.894 (2) Å].

Related literature

For biological activity, see: Cina et al. (1996); Karamanakos et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₈H₁₂N₄O₄
M_r = 228.22
Monoclinic, P 2₁ /n
a = 9.6959 (12) Å
b = 7.2898 (9) Å
c = 15.589 (2) Å
= 101.400 (2)°
V = 1080.1 (2) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 273 (2) K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
5515 measured reflections
1921 independent reflections
1622 reflections with I > 2(I)
R_int = 0.015

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.089
S = 1.05
1921 reflections
146 parameters
H-atom parameters constrained
_max = 0.19 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H4N1ⁱ	0.86	2.20	3.0416 (17)	165
C2-H2O4ⁱⁱ	0.93	2.34	3.2492 (18)	166
C8-H8BO4ⁱⁱⁱ	0.96	2.57	3.498 (2)	164
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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: HG2452 ).

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.
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin.
Cina, S. J., Russell, R. A. & Conradi, S. E. (1996). Am. J. Foren. Med. Path. 17, 343-346.
Karamanakos, P. N., Pappas, P., Boumba, V. A., Thomas, C., Malamas, M., Vougiouklakis, T. & Marselos, M. (2007). Int. J. Toxicol. 26, 423-432.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds