Methyl 2-{[2-(4,4,5,5-tetra­methyl-1,3-dioxyl-4,5-dihydro­imidazol-2-yl)phen­yl]­oxy}acetate

Wang, H.-B.; Jing, L.-L.; Sun, X.-L.

doi:10.1107/S1600536811054018

Volume 68
Part 1
Page o217
January 2012

Received 12 December 2011
Accepted 15 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R = 0.060
wR = 0.219
Data-to-parameter ratio = 14.5
Details

Methyl 2-{[2-(4,4,5,5-tetramethyl-1,3-dioxyl-4,5-dihydroimidazol-2-yl)phenyl]oxy}acetate

Hai-Bo Wang,^a Lin-Lin Jing ^b and Xiao-Li Sun ^a ^*

^aDepartment of Chemistry, School of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032, Xi-An, People's Republic of China, and ^bDepartment of Pharmacy, Lanzhou General Hospital of PLA, Key laboratory of the Prevention and Cure for the Plateau Environment Damage, PLA, 730050 Lanzhou Gansu, People's Republic of China
Correspondence e-mail: xiaoli_sun@yahoo.cn

In the title compound, C₁₆H₂₁N₂O₅, the benzene ring is nearly perpendicular to the imidazole ring, making a torsion angle of 88.6 (8)°·The crystal structure is stabilized by non-classical C-HO and C-H [pi] interactions, which build up a three-dimensional network.

Related literature

For the chemical and physical properties of nitronyl nitroxides, see: Osiecki & Ullman (1968). For their biological activity, see: Soule et al. (2007). For related structures, see: Wang et al. (2009); Jing et al. (2011).

Experimental

Crystal data

C₁₆H₂₁N₂O₅
M_r = 321.35
Monoclinic, P 2₁ /c
a = 11.421 (6) Å
b = 7.381 (4) Å
c = 19.700 (11) Å
= 91.832 (6)°
V = 1659.8 (16) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 296 K
0.23 × 0.21 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007) T_min = 0.978, T_max = 0.987
11481 measured reflections
3082 independent reflections
1717 reflections with I > 2(I)
R_int = 0.049

Refinement

R[F² > 2(F²)] = 0.060
wR(F²) = 0.219
S = 0.95
3082 reflections
213 parameters
30 restraints
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.42 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the phenyl ring.

D-HA	D-H	HA	DA	D-HA
C3-H3AO4ⁱ	0.97	2.51	3.327 (5)	141
C3-H3BO4ⁱⁱ	0.97	2.44	3.195 (5)	134
C8-H8Cg2ⁱⁱⁱ	0.93	2.99	3.896 (5)	164
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x, y+1, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5154 ).

Acknowledgements

We thank the Natural Science Foundation of China (grant No. 81001398) for financial support and Yongliang Shao (Lanzhou University) for the X-ray measurements.

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Jing, L.-L., Ma, H.-P., He, L., Fan, P.-C. & Jia, Z.-P. (2011). Acta Cryst. E67, o3503.
Osiecki, J. H. & Ullman, E. F. (1968). J. Am. Chem. Soc. 90, 1078-1079.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Soule, B. P., Hyodo, F., Matsumoto, K., Simone, N. L., Cook, J. A., Krishna, M. C. & Mitchell, J. B. (2007). Free Radic. Biol. Med. 42, 1632-1650.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, H.-B., Jing, L.-L., Gao, P. & Sun, X.-L. (2009). Acta Cryst. E65, o2090.

organic compounds