2-[3-Hy-droxy-4-(2-hy-droxy-eth-oxy)phen-yl]-4,4,5,5-tetra-methyl-2-imidazoline-1-oxyl 3-oxide.

In the title compound, C(15)H(21)N(2)O(5), 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 mol-ecules 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 = 309.34

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 1.01

2784 reflections

206 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.14 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811053979/is5030sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H21N2O5	F(000) = 660
Mr = 309.34	Dx = 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

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

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(Fo2) + (0.0486P)2 + 0.519P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2784 reflections	Δρmax = 0.21 e Å−3
206 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .