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Volume 68 
Part 1 
Page o218  
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) = 0.003 Å
R = 0.038
wR = 0.103
Data-to-parameter ratio = 13.5
Details
Open access

2-[3-Hydroxy-4-(2-hydroxyethoxy)phenyl]-4,4,5,5-tetramethyl-2-imidazoline-1-oxyl 3-oxide

aDepartment 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: zhengping_jia@yahoo.cn

In the title compound, C15H21N2O5, the imidazoline ring displays a twisted conformation. The mean plane of the imidazoline ring makes a dihedral angle of 22.55 (5)° with the benzene ring. In the crystal, O-H...O and C-H...O hydrogen bonds link the molecules into a layer parallel to the bc plane.

Related literature

For the biological activity of nitronyl nitroxides, 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.]); Blasig et al. (2002[Blasig, I. E., Mertsch, K. & Haseloff, R. F. (2002). Neuropharmacology, 43, 1006-1014.]); Qin et al. (2009[Qin, X. Y., Ding, G. R. & Sun, X. L. (2009). J. Chem. Res. pp. 511-514.]); Tanaka et al. (2007[Tanaka, K., Furuichi, K., Kozaki, M., Suzuki, S., Shiomi, D., Sato, K., Takui, T. & Okada, K. (2007). Polyhedron, 26, 2021-2026.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For pseudorotation parameters, see: Rao et al. (1981[Rao, S. T., Westhof, E. & Sundaralingam, M. (1981). Acta Cryst. A37, 421-425.]). For related structures, see: Jing, Ma, Fan et al. (2011[Jing, L.-L., Ma, H.-P., Fan, X.-F., He, L. & Jia, Z.-P. (2011). Acta Cryst. E67, o3348.]); Jing, Ma, He 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
  • C15H21N2O5

  • Mr = 309.34

  • Monoclinic, P 21 /c

  • a = 9.787 (4) Å

  • b = 9.302 (3) Å

  • c = 16.657 (6) Å

  • [beta] = 93.525 (3)°

  • V = 1513.5 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.25 × 0.23 × 0.21 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 = 0.975, Tmax = 0.979

  • 7023 measured reflections

  • 2784 independent reflections

  • 2172 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.103

  • S = 1.01

  • 2784 reflections

  • 206 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3A...O1i 0.82 1.91 2.678 (2) 156
O5-H5A...O3ii 0.82 2.34 2.993 (2) 137
O5-H5A...O4ii 0.82 2.46 3.111 (2) 137
C12-H12A...O5iii 0.96 2.57 3.410 (3) 146
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+2, -y+2, -z+2; (iii) x, y-1, z.

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 (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: IS5030 ).


Acknowledgements

We thank the Natural Science Foundation of Gansu (grant No. 1107RJZA100) for financial support.

References

Blasig, I. E., Mertsch, K. & Haseloff, R. F. (2002). Neuropharmacology, 43, 1006-1014.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Jing, L.-L., Ma, H.-P., Fan, X.-F., He, L. & Jia, Z.-P. (2011). Acta Cryst. E67, o3348.  [CrossRef] [details]
Jing, L.-L., Ma, H.-P., He, L., Fan, P.-C. & Jia, Z.-P. (2011). Acta Cryst. E67, o3503.  [CrossRef] [details]
Qin, X. Y., Ding, G. R. & Sun, X. L. (2009). J. Chem. Res. pp. 511-514.  [ISI] [CrossRef] [ChemPort]
Rao, S. T., Westhof, E. & Sundaralingam, M. (1981). Acta Cryst. A37, 421-425.  [CrossRef] [details]
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]
Tanaka, K., Furuichi, K., Kozaki, M., Suzuki, S., Shiomi, D., Sato, K., Takui, T. & Okada, K. (2007). Polyhedron, 26, 2021-2026.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o218  [ doi:10.1107/S1600536811053979 ]

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