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

Ma, H.-P.; Jing, L.-L.; He, L.; Fan, P.-C.; Jia, Z.-P.

doi:10.1107/S1600536811053979

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 (C-C) = 0.003 Å
R = 0.038
wR = 0.103
Data-to-parameter ratio = 13.5
Details

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

Hui-Ping Ma,^a Lin-Lin Jing,^a Lei He,^a Peng-Cheng Fan ^a and Zheng-Ping Jia ^a ^*

^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-HO and C-HO 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); Blasig et al. (2002); Qin et al. (2009); Tanaka et al. (2007). For puckering parameters, see: Cremer & Pople (1975). For pseudorotation parameters, see: Rao et al. (1981). For related structures, see: Jing, Ma, Fan et al. (2011); Jing, Ma, He et al. (2011).

Experimental

Crystal data

C₁₅H₂₁N₂O₅
M_r = 309.34
Monoclinic, P 2₁ /c
a = 9.787 (4) Å
b = 9.302 (3) Å
c = 16.657 (6) Å
= 93.525 (3)°
V = 1513.5 (10) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.975, T_max = 0.979
7023 measured reflections
2784 independent reflections
2172 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.103
S = 1.01
2784 reflections
206 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3AO1ⁱ	0.82	1.91	2.678 (2)	156
O5-H5AO3ⁱⁱ	0.82	2.34	2.993 (2)	137
O5-H5AO4ⁱⁱ	0.82	2.46	3.111 (2)	137
C12-H12AO5ⁱⁱⁱ	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); 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 (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: 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.
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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Jing, L.-L., Ma, H.-P., Fan, X.-F., He, L. & Jia, Z.-P. (2011). Acta Cryst. E67, o3348.
Jing, L.-L., Ma, H.-P., He, L., Fan, P.-C. & Jia, Z.-P. (2011). Acta Cryst. E67, o3503.
Qin, X. Y., Ding, G. R. & Sun, X. L. (2009). J. Chem. Res. pp. 511-514.
Rao, S. T., Westhof, E. & Sundaralingam, M. (1981). Acta Cryst. A37, 421-425.
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.
Tanaka, K., Furuichi, K., Kozaki, M., Suzuki, S., Shiomi, D., Sato, K., Takui, T. & Okada, K. (2007). Polyhedron, 26, 2021-2026.

organic compounds