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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 [sigma](C-C) = 0.005 Å
R = 0.060
wR = 0.219
Data-to-parameter ratio = 14.5
Details
Open access

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

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-H...O 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[Osiecki, J. H. & Ullman, E. F. (1968). J. Am. Chem. Soc. 90, 1078-1079.]). For their biological activity, see: Soule et al. (2007[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.]). For related structures, see: Wang et al. (2009[Wang, H.-B., Jing, L.-L., Gao, P. & Sun, X.-L. (2009). Acta Cryst. E65, o2090.]); Jing et al. (2011[Jing, L.-L., Ma, H.-P., He, L., Fan, P.-C. & Jia, Z.-P. (2011). Acta Cryst. E67, o3503.]).

[Scheme 1]

Experimental

Crystal data
  • C16H21N2O5

  • Mr = 321.35

  • Monoclinic, P 21 /c

  • a = 11.421 (6) Å

  • b = 7.381 (4) Å

  • c = 19.700 (11) Å

  • [beta] = 91.832 (6)°

  • V = 1659.8 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.987

  • 11481 measured reflections

  • 3082 independent reflections

  • 1717 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.219

  • S = 0.95

  • 3082 reflections

  • 213 parameters

  • 30 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the phenyl ring.

D-H...A D-H H...A D...A D-H...A
C3-H3A...O4i 0.97 2.51 3.327 (5) 141
C3-H3B...O4ii 0.97 2.44 3.195 (5) 134
C8-H8...Cg2iii 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[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [CrossRef] [details]
Jing, L.-L., Ma, H.-P., He, L., Fan, P.-C. & Jia, Z.-P. (2011). Acta Cryst. E67, o3503.  [CrossRef] [details]
Osiecki, J. H. & Ullman, E. F. (1968). J. Am. Chem. Soc. 90, 1078-1079.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
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.  [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wang, H.-B., Jing, L.-L., Gao, P. & Sun, X.-L. (2009). Acta Cryst. E65, o2090.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o217  [ doi:10.1107/S1600536811054018 ]

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