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

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o218

doi:10.1107/S1600536811053979

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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

(Received 12 December 2011; accepted 15 December 2011; online 23 December 2011)

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 ); 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
β = 93.525 (3)°
V = 1513.5 (10) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.103
S = 1.01
2784 reflections
206 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_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); 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811053979/is5030sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053979/is5030Isup2.hkl

checkCIF report

Comment top

Nitronyl nitroxides, which can react with free radicals such as OH, H₂O₂, and O₂ (Blasig et al., 2002) to protect cells from the attack of free radicals have lots of biological properities as anticancer, antiradiation and antioxidation (Qin et al., 2009; Tanaka et al., 2007; Soule et al., 2007).

The molecular structure of the title compound is shown in Fig. 1. The nitronyl nitroxide ring and the phenyl rings are twisted with respect to each other making a dihedral angle of 22.55 (5)°. The puckering parameters of the nitronyl nitroxide ring are Q(2) = 0.2645 (17) Å and ϕ = 121.9 (4)° (Cremer & Pople, 1975). The pseudorotation parameters (Rao et al., 1981) for the nitronyl nitroxide ring are P = 283.2 (2)° and τ(M) = 27.1 (1)° for the C7—N1 reference bond with the closest puckering descriptor being twisted on C8—C9. The crystal structure is stabilized by O—H···O and C—H···O hydrogen bonds (Table 1).

Related literature top

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 top

To a solution of 3-hydroxy-4-(2-hydroxyethoxy)benzaldehyde (0.91 g, 5 mmol) in methanol (20 ml), 2,3-dimethyl-2,3-bis(hydroxylamino) butane (0.74 g, 5.0 mmol) was added. The mixture was stirring for 24 h at room temperature then filtered. The resulting white powder was suspended in the solution of dichloromethane (20.0 ml). An aqueous solution of NaIO₄ (20 ml) was added to the reaction mixture and stirred for 15 min in an ice bath. The aqueous phase was extracted with CH₂Cl₂ and the combined organic layers were washed with brine (20 ml) and dried over Na₂SO₄. the solvent was removed to obtain a dark blue residue which was purified by flash column chromatography with the elution of dichloromethane/ methanol (10:1) to yield 0.70 g (45%) of the title compound as a dark blue powder. Single crystals of the title compound suitable for X-ray diffraction was recrystallized from hexane/dichloromethane (1:2).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

Fig. 1. Molecular structure of the title compound with atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.

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

Crystal data top

C₁₅H₂₁N₂O₅	F(000) = 660
M_r = 309.34	D_x = 1.358 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2979 reflections
a = 9.787 (4) Å	θ = 2.5–27.7°
b = 9.302 (3) Å	µ = 0.10 mm⁻¹
c = 16.657 (6) Å	T = 296 K
β = 93.525 (3)°	Block, blue
V = 1513.5 (10) Å³	0.25 × 0.23 × 0.21 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2784 independent reflections
Radiation source: fine-focus sealed tube	2172 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→8
T_min = 0.975, T_max = 0.979	k = −11→10
7023 measured reflections	l = −20→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0486P)² + 0.519P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2784 reflections	Δρ_max = 0.21 e Å⁻³
206 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0167 (18)

Crystal data top

C₁₅H₂₁N₂O₅	V = 1513.5 (10) Å³
M_r = 309.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.787 (4) Å	µ = 0.10 mm⁻¹
b = 9.302 (3) Å	T = 296 K
c = 16.657 (6) Å	0.25 × 0.23 × 0.21 mm
β = 93.525 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2784 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2172 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.979	R_int = 0.023
7023 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.01	Δρ_max = 0.21 e Å⁻³
2784 reflections	Δρ_min = −0.14 e Å⁻³
206 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.84569 (17)	0.65658 (17)	0.96445 (9)	0.0307 (4)
C2	0.90504 (16)	0.61269 (17)	0.89405 (9)	0.0291 (4)
C3	0.86536 (16)	0.48613 (17)	0.85697 (9)	0.0294 (4)
H3	0.9052	0.4577	0.8103	0.035*
C4	0.76514 (16)	0.39970 (17)	0.88925 (9)	0.0287 (4)
C5	0.70732 (19)	0.44374 (19)	0.95909 (10)	0.0399 (4)
H5	0.6409	0.3870	0.9812	0.048*
C6	0.74747 (19)	0.57120 (19)	0.99621 (10)	0.0403 (5)
H6	0.7078	0.5995	1.0430	0.048*
C7	0.71796 (16)	0.26786 (17)	0.84938 (9)	0.0276 (4)
C8	0.69965 (17)	0.06957 (17)	0.76020 (10)	0.0330 (4)
C9	0.58253 (17)	0.06193 (17)	0.81818 (10)	0.0330 (4)
C10	0.7809 (2)	−0.0678 (2)	0.75295 (14)	0.0548 (6)
H10A	0.8528	−0.0526	0.7172	0.082*
H10B	0.7214	−0.1428	0.7320	0.082*
H10C	0.8199	−0.0952	0.8050	0.082*
C11	0.6547 (2)	0.1276 (2)	0.67686 (11)	0.0498 (5)
H11A	0.6049	0.2156	0.6824	0.075*
H11B	0.5972	0.0582	0.6487	0.075*
H11C	0.7340	0.1456	0.6471	0.075*
C12	0.6080 (2)	−0.0420 (2)	0.88796 (12)	0.0538 (5)
H12A	0.6964	−0.0235	0.9141	0.081*
H12B	0.6050	−0.1389	0.8681	0.081*
H12C	0.5387	−0.0294	0.9257	0.081*
C13	0.44130 (18)	0.0385 (2)	0.77753 (12)	0.0476 (5)
H13A	0.3753	0.0308	0.8176	0.071*
H13B	0.4411	−0.0484	0.7464	0.071*
H13C	0.4181	0.1183	0.7428	0.071*
C14	0.8384 (2)	0.83103 (19)	1.06967 (10)	0.0397 (4)
H14A	0.8655	0.7640	1.1123	0.048*
H14B	0.7392	0.8347	1.0644	0.048*
C15	0.8949 (2)	0.9769 (2)	1.08947 (11)	0.0419 (5)
H15A	0.8817	0.9993	1.1453	0.050*
H15B	0.9924	0.9784	1.0819	0.050*
N1	0.78767 (13)	0.18428 (14)	0.80059 (8)	0.0290 (3)
N2	0.59145 (14)	0.20965 (14)	0.85370 (8)	0.0328 (3)
O1	0.91259 (12)	0.20380 (13)	0.78261 (7)	0.0408 (3)
O2	0.49072 (13)	0.26599 (15)	0.88724 (9)	0.0549 (4)
O3	1.00204 (13)	0.70239 (14)	0.86708 (8)	0.0450 (4)
H3A	1.0205	0.6781	0.8217	0.067*
O4	0.89083 (12)	0.78448 (12)	0.99533 (7)	0.0377 (3)
O5	0.82812 (16)	1.08039 (14)	1.03935 (10)	0.0603 (4)
H5A	0.8753	1.1532	1.0385	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0359 (9)	0.0251 (8)	0.0311 (8)	−0.0062 (7)	0.0024 (7)	−0.0044 (7)
C2	0.0272 (8)	0.0273 (8)	0.0335 (8)	−0.0041 (7)	0.0065 (7)	0.0005 (7)
C3	0.0293 (9)	0.0290 (9)	0.0306 (8)	−0.0009 (7)	0.0069 (7)	−0.0044 (7)
C4	0.0304 (9)	0.0261 (8)	0.0297 (8)	−0.0029 (7)	0.0026 (7)	−0.0020 (6)
C5	0.0500 (11)	0.0345 (10)	0.0366 (9)	−0.0179 (8)	0.0149 (8)	−0.0064 (8)
C6	0.0525 (12)	0.0372 (10)	0.0330 (9)	−0.0155 (9)	0.0182 (8)	−0.0096 (7)
C7	0.0282 (9)	0.0256 (8)	0.0294 (8)	−0.0014 (7)	0.0039 (7)	−0.0020 (6)
C8	0.0319 (9)	0.0275 (9)	0.0393 (9)	−0.0010 (7)	0.0008 (7)	−0.0103 (7)
C9	0.0349 (9)	0.0257 (9)	0.0383 (9)	−0.0058 (7)	0.0001 (7)	−0.0077 (7)
C10	0.0427 (12)	0.0354 (11)	0.0864 (16)	0.0029 (9)	0.0069 (11)	−0.0212 (10)
C11	0.0516 (12)	0.0604 (13)	0.0370 (10)	−0.0061 (10)	0.0010 (9)	−0.0106 (9)
C12	0.0684 (15)	0.0405 (11)	0.0520 (12)	−0.0144 (10)	−0.0018 (10)	0.0039 (9)
C13	0.0332 (10)	0.0472 (11)	0.0619 (12)	−0.0073 (9)	−0.0003 (9)	−0.0173 (10)
C14	0.0469 (11)	0.0383 (10)	0.0350 (9)	−0.0117 (8)	0.0114 (8)	−0.0096 (7)
C15	0.0455 (11)	0.0407 (11)	0.0397 (9)	−0.0105 (9)	0.0048 (8)	−0.0124 (8)
N1	0.0261 (7)	0.0283 (7)	0.0329 (7)	−0.0013 (6)	0.0037 (6)	−0.0048 (6)
N2	0.0287 (8)	0.0308 (8)	0.0397 (8)	−0.0041 (6)	0.0086 (6)	−0.0106 (6)
O1	0.0285 (7)	0.0448 (8)	0.0504 (7)	−0.0046 (5)	0.0128 (5)	−0.0120 (6)
O2	0.0346 (7)	0.0536 (9)	0.0789 (10)	−0.0084 (6)	0.0227 (7)	−0.0303 (7)
O3	0.0498 (8)	0.0398 (7)	0.0478 (8)	−0.0199 (6)	0.0229 (6)	−0.0127 (6)
O4	0.0459 (7)	0.0306 (6)	0.0380 (7)	−0.0130 (5)	0.0142 (5)	−0.0105 (5)
O5	0.0572 (9)	0.0358 (8)	0.0862 (11)	−0.0076 (7)	−0.0097 (8)	−0.0098 (7)

Geometric parameters (Å, º) top

C1—O4	1.3591 (19)	C10—H10B	0.9600
C1—C6	1.377 (2)	C10—H10C	0.9600
C1—C2	1.401 (2)	C11—H11A	0.9600
C2—O3	1.3607 (19)	C11—H11B	0.9600
C2—C3	1.374 (2)	C11—H11C	0.9600
C3—C4	1.401 (2)	C12—H12A	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C4—C5	1.387 (2)	C12—H12C	0.9600
C4—C7	1.456 (2)	C13—H13A	0.9600
C5—C6	1.383 (2)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C6—H6	0.9300	C14—O4	1.436 (2)
C7—N1	1.341 (2)	C14—C15	1.494 (2)
C7—N2	1.357 (2)	C14—H14A	0.9700
C8—N1	1.504 (2)	C14—H14B	0.9700
C8—C10	1.514 (2)	C15—O5	1.408 (2)
C8—C11	1.529 (3)	C15—H15A	0.9700
C8—C9	1.545 (2)	C15—H15B	0.9700
C9—N2	1.496 (2)	N1—O1	1.2893 (17)
C9—C13	1.517 (2)	N2—O2	1.2753 (18)
C9—C12	1.521 (3)	O3—H3A	0.8200
C10—H10A	0.9600	O5—H5A	0.8200

O4—C1—C6	125.29 (15)	C8—C11—H11A	109.5
O4—C1—C2	115.46 (14)	C8—C11—H11B	109.5
C6—C1—C2	119.24 (14)	H11A—C11—H11B	109.5
O3—C2—C3	124.08 (14)	C8—C11—H11C	109.5
O3—C2—C1	115.55 (14)	H11A—C11—H11C	109.5
C3—C2—C1	120.37 (14)	H11B—C11—H11C	109.5
C2—C3—C4	120.29 (14)	C9—C12—H12A	109.5
C2—C3—H3	119.9	C9—C12—H12B	109.5
C4—C3—H3	119.9	H12A—C12—H12B	109.5
C5—C4—C3	118.94 (15)	C9—C12—H12C	109.5
C5—C4—C7	119.81 (14)	H12A—C12—H12C	109.5
C3—C4—C7	121.21 (14)	H12B—C12—H12C	109.5
C6—C5—C4	120.59 (15)	C9—C13—H13A	109.5
C6—C5—H5	119.7	C9—C13—H13B	109.5
C4—C5—H5	119.7	H13A—C13—H13B	109.5
C1—C6—C5	120.57 (15)	C9—C13—H13C	109.5
C1—C6—H6	119.7	H13A—C13—H13C	109.5
C5—C6—H6	119.7	H13B—C13—H13C	109.5
N1—C7—N2	107.49 (13)	O4—C14—C15	108.50 (14)
N1—C7—C4	127.28 (14)	O4—C14—H14A	110.0
N2—C7—C4	125.20 (14)	C15—C14—H14A	110.0
N1—C8—C10	110.22 (14)	O4—C14—H14B	110.0
N1—C8—C11	106.28 (14)	C15—C14—H14B	110.0
C10—C8—C11	110.42 (16)	H14A—C14—H14B	108.4
N1—C8—C9	100.34 (12)	O5—C15—C14	109.76 (15)
C10—C8—C9	115.11 (15)	O5—C15—H15A	109.7
C11—C8—C9	113.64 (15)	C14—C15—H15A	109.7
N2—C9—C13	109.74 (14)	O5—C15—H15B	109.7
N2—C9—C12	106.19 (14)	C14—C15—H15B	109.7
C13—C9—C12	110.61 (16)	H15A—C15—H15B	108.2
N2—C9—C8	100.22 (12)	O1—N1—C7	125.74 (13)
C13—C9—C8	114.72 (14)	O1—N1—C8	121.41 (12)
C12—C9—C8	114.44 (15)	C7—N1—C8	112.56 (13)
C8—C10—H10A	109.5	O2—N2—C7	126.26 (14)
C8—C10—H10B	109.5	O2—N2—C9	121.51 (13)
H10A—C10—H10B	109.5	C7—N2—C9	112.12 (13)
C8—C10—H10C	109.5	C2—O3—H3A	109.5
H10A—C10—H10C	109.5	C1—O4—C14	117.73 (12)
H10B—C10—H10C	109.5	C15—O5—H5A	109.5

O4—C1—C2—O3	1.4 (2)	C11—C8—C9—C12	158.75 (15)
C6—C1—C2—O3	−179.41 (16)	O4—C14—C15—O5	74.74 (19)
O4—C1—C2—C3	−178.96 (15)	N2—C7—N1—O1	−178.94 (14)
C6—C1—C2—C3	0.2 (3)	C4—C7—N1—O1	2.8 (3)
O3—C2—C3—C4	179.57 (16)	N2—C7—N1—C8	7.18 (18)
C1—C2—C3—C4	0.0 (2)	C4—C7—N1—C8	−171.10 (15)
C2—C3—C4—C5	−0.2 (2)	C10—C8—N1—O1	42.6 (2)
C2—C3—C4—C7	177.74 (15)	C11—C8—N1—O1	−77.09 (18)
C3—C4—C5—C6	0.2 (3)	C9—C8—N1—O1	164.37 (14)
C7—C4—C5—C6	−177.73 (16)	C10—C8—N1—C7	−143.25 (16)
O4—C1—C6—C5	178.91 (17)	C11—C8—N1—C7	97.09 (16)
C2—C1—C6—C5	−0.2 (3)	C9—C8—N1—C7	−21.46 (17)
C4—C5—C6—C1	−0.1 (3)	N1—C7—N2—O2	−172.08 (16)
C5—C4—C7—N1	−155.39 (17)	C4—C7—N2—O2	6.2 (3)
C3—C4—C7—N1	26.7 (2)	N1—C7—N2—C9	11.58 (18)
C5—C4—C7—N2	26.6 (3)	C4—C7—N2—C9	−170.10 (15)
C3—C4—C7—N2	−151.31 (16)	C13—C9—N2—O2	38.3 (2)
N1—C8—C9—N2	24.92 (14)	C12—C9—N2—O2	−81.3 (2)
C10—C8—C9—N2	143.18 (15)	C8—C9—N2—O2	159.39 (15)
C11—C8—C9—N2	−88.10 (16)	C13—C9—N2—C7	−145.15 (15)
N1—C8—C9—C13	142.35 (15)	C12—C9—N2—C7	95.28 (17)
C10—C8—C9—C13	−99.39 (19)	C8—C9—N2—C7	−24.07 (16)
C11—C8—C9—C13	29.3 (2)	C6—C1—O4—C14	4.0 (3)
N1—C8—C9—C12	−88.24 (16)	C2—C1—O4—C14	−176.92 (15)
C10—C8—C9—C12	30.0 (2)	C15—C14—O4—C1	−176.62 (15)

Hydrogen-bond geometry (Å, º) top

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+1/2, −z+3/2; (ii) −x+2, −y+2, −z+2; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₁N₂O₅
M_r	309.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.787 (4), 9.302 (3), 16.657 (6)
β (°)	93.525 (3)
V (Å³)	1513.5 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.23 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.975, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	7023, 2784, 2172
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.103, 1.01
No. of reflections	2784
No. of parameters	206
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.14

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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+1/2, −z+3/2; (ii) −x+2, −y+2, −z+2; (iii) x, y−1, z.

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. Web of Science CrossRef PubMed CAS Google Scholar
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Volume 68| Part 1| January 2012| Page o218

doi:10.1107/S1600536811053979

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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