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

In the title compound, C(15)H(21)N(2)O(4), the imidazoline ring displays a twisted conformation. The dihedral angle between the mean plane of the imidazoline ring and the benzene ring is 33.50 (12)°. In the crystal, mol-ecules are connected by O-H⋯O hydrogen bonds, forming a zigzag chain along the c axis. The chains are linked by C-H⋯O and C-H⋯π inter-actions.

Related literature

For the preparation of the title compound, see: Ullman et al. (1974 ▶). For biological properties of nitronyl nitroxides, see: Soule et al. (2007 ▶); Blasig et al. (2002 ▶); Qin et al. (2009 ▶); Tanaka et al. (2007 ▶). For coordination properties of nitronyl nitroxides, see: Masuda et al. (2009 ▶). For related structures, see: Wang et al. (2009 ▶); Jing et al. (2009 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For pseudorotation parameters, see: Rao et al. (1981 ▶).

Experimental

Crystal data

C15H21N2O4

M = 293.34

Orthorhombic,

a = 8.869 (3) Å

b = 16.050 (5) Å

c = 20.925 (6) Å

V = 2978.7 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.26 × 0.23 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.976, T max = 0.979

20164 measured reflections

2774 independent reflections

1928 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.163

S = 0.95

2774 reflections

195 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.25 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/S160053681104815X/is5006sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104815X/is5006Isup2.hkl

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

C15H21N2O4	F(000) = 1256
Mr = 293.34	Dx = 1.308 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3005 reflections
a = 8.869 (3) Å	θ = 2.5–21.6°
b = 16.050 (5) Å	µ = 0.10 mm−1
c = 20.925 (6) Å	T = 296 K
V = 2978.7 (16) Å3	Block, blue
Z = 8	0.26 × 0.23 × 0.22 mm

Bruker APEXII CCD diffractometer	2774 independent reflections
Radiation source: fine-focus sealed tube	1928 reflections with I > 2σ(I)
graphite	Rint = 0.054
φ and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
Tmin = 0.976, Tmax = 0.979	k = −17→19
20164 measured reflections	l = −25→25

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.1P)2 + 0.8575P] where P = (Fo2 + 2Fc2)/3
2774 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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	0.8584 (2)	1.12763 (14)	0.33524 (10)	0.0381 (5)
C2	0.8507 (3)	1.05283 (14)	0.38244 (10)	0.0401 (5)
C3	0.8131 (2)	1.00297 (13)	0.27718 (9)	0.0338 (5)
C4	0.7901 (2)	0.94682 (13)	0.22347 (9)	0.0333 (5)
C5	0.6890 (3)	0.88085 (13)	0.22601 (10)	0.0405 (5)
H5	0.6343	0.8719	0.2633	0.049*
C6	0.6678 (3)	0.82848 (13)	0.17472 (10)	0.0405 (5)
H6	0.5986	0.7851	0.1773	0.049*
C7	0.7503 (3)	0.84085 (13)	0.11912 (9)	0.0351 (5)
C8	0.8535 (3)	0.90560 (15)	0.11621 (10)	0.0417 (6)
H8	0.9098	0.9136	0.0792	0.050*
C9	0.8733 (3)	0.95792 (14)	0.16734 (10)	0.0399 (6)
H9	0.9427	1.0012	0.1647	0.048*
C10	0.6427 (3)	0.72306 (15)	0.06578 (10)	0.0463 (6)
H10A	0.5408	0.7395	0.0770	0.056*
H10B	0.6778	0.6829	0.0971	0.056*
C11	0.6449 (3)	0.68517 (19)	0.00040 (12)	0.0586 (7)
H11A	0.5780	0.6374	−0.0007	0.070*
H11B	0.6087	0.7255	−0.0305	0.070*
C12	0.7205 (3)	1.18423 (16)	0.33598 (13)	0.0550 (7)
H12A	0.7275	1.2236	0.3016	0.083*
H12B	0.7161	1.2135	0.3759	0.083*
H12C	0.6311	1.1512	0.3309	0.083*
C13	1.0013 (3)	1.17980 (17)	0.33876 (13)	0.0569 (7)
H13A	1.0871	1.1452	0.3300	0.085*
H13B	1.0106	1.2034	0.3807	0.085*
H13C	0.9962	1.2238	0.3077	0.085*
C14	0.7400 (4)	1.06293 (18)	0.43721 (12)	0.0653 (8)
H14A	0.6413	1.0741	0.4204	0.098*
H14B	0.7711	1.1085	0.4638	0.098*
H14C	0.7375	1.0126	0.4620	0.098*
C15	1.0041 (3)	1.02474 (19)	0.40759 (13)	0.0638 (8)
H15A	0.9929	0.9733	0.4305	0.096*
H15B	1.0440	1.0665	0.4357	0.096*
H15C	1.0720	1.0167	0.3724	0.096*
N1	0.8557 (2)	1.08321 (11)	0.27221 (8)	0.0368 (4)
N2	0.7976 (2)	0.98429 (11)	0.33930 (8)	0.0374 (5)
O1	0.8756 (2)	1.12342 (10)	0.21999 (7)	0.0558 (5)
O2	0.7595 (2)	0.91285 (10)	0.36180 (7)	0.0581 (5)
O3	0.73915 (18)	0.79412 (10)	0.06528 (7)	0.0464 (4)
O4	0.7906 (3)	0.66024 (15)	−0.01595 (10)	0.0783 (7)
H4	0.7890	0.6369	−0.0508	0.117*

	U11	U22	U33	U12	U13	U23
C1	0.0401 (12)	0.0392 (13)	0.0350 (11)	−0.0033 (10)	0.0006 (9)	−0.0095 (9)
C2	0.0493 (13)	0.0421 (13)	0.0288 (10)	−0.0015 (10)	−0.0004 (9)	−0.0067 (9)
C3	0.0397 (11)	0.0330 (12)	0.0289 (10)	0.0003 (10)	0.0010 (8)	0.0005 (8)
C4	0.0399 (12)	0.0319 (11)	0.0280 (10)	0.0023 (9)	−0.0011 (8)	0.0003 (8)
C5	0.0521 (13)	0.0402 (13)	0.0293 (10)	−0.0037 (11)	0.0089 (9)	−0.0004 (9)
C6	0.0537 (14)	0.0347 (12)	0.0331 (11)	−0.0076 (10)	0.0056 (10)	−0.0016 (9)
C7	0.0421 (12)	0.0342 (11)	0.0289 (10)	0.0037 (9)	−0.0009 (9)	−0.0045 (8)
C8	0.0444 (12)	0.0491 (14)	0.0315 (11)	−0.0040 (11)	0.0113 (9)	−0.0042 (9)
C9	0.0422 (13)	0.0423 (13)	0.0352 (11)	−0.0078 (10)	0.0065 (9)	−0.0050 (9)
C10	0.0536 (14)	0.0489 (14)	0.0363 (11)	−0.0112 (11)	−0.0006 (10)	−0.0037 (10)
C11	0.0661 (18)	0.0676 (18)	0.0420 (14)	−0.0164 (14)	−0.0063 (12)	−0.0132 (12)
C12	0.0545 (16)	0.0485 (15)	0.0621 (16)	0.0082 (12)	−0.0003 (12)	−0.0064 (12)
C13	0.0537 (16)	0.0619 (17)	0.0550 (15)	−0.0171 (13)	−0.0008 (12)	−0.0081 (13)
C14	0.092 (2)	0.0601 (17)	0.0438 (14)	−0.0058 (15)	0.0248 (14)	−0.0106 (12)
C15	0.0679 (18)	0.0708 (19)	0.0527 (15)	0.0060 (15)	−0.0233 (14)	0.0018 (13)
N1	0.0449 (11)	0.0363 (10)	0.0293 (9)	−0.0035 (8)	0.0014 (7)	−0.0010 (7)
N2	0.0505 (11)	0.0355 (10)	0.0261 (8)	−0.0023 (8)	0.0013 (7)	0.0005 (7)
O1	0.0892 (14)	0.0420 (10)	0.0363 (9)	−0.0110 (9)	0.0059 (8)	0.0083 (7)
O2	0.0993 (14)	0.0428 (10)	0.0322 (8)	−0.0155 (10)	0.0016 (8)	0.0072 (7)
O3	0.0640 (11)	0.0435 (9)	0.0317 (8)	−0.0112 (8)	0.0074 (7)	−0.0106 (6)
O4	0.0952 (17)	0.0864 (16)	0.0532 (12)	0.0100 (13)	0.0002 (10)	−0.0280 (10)

C1—N1	1.499 (3)	C10—C11	1.497 (3)
C1—C13	1.520 (3)	C10—H10A	0.9700
C1—C12	1.524 (3)	C10—H10B	0.9700
C1—C2	1.556 (3)	C11—O4	1.395 (3)
C2—N2	1.499 (3)	C11—H11A	0.9700
C2—C14	1.518 (3)	C11—H11B	0.9700
C2—C15	1.527 (4)	C12—H12A	0.9600
C3—N2	1.341 (3)	C12—H12B	0.9600
C3—N1	1.346 (3)	C12—H12C	0.9600
C3—C4	1.455 (3)	C13—H13A	0.9600
C4—C5	1.389 (3)	C13—H13B	0.9600
C4—C9	1.398 (3)	C13—H13C	0.9600
C5—C6	1.376 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—C7	1.389 (3)	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C7—O3	1.357 (2)	C15—H15B	0.9600
C7—C8	1.386 (3)	C15—H15C	0.9600
C8—C9	1.371 (3)	N1—O1	1.281 (2)
C8—H8	0.9300	N2—O2	1.285 (2)
C9—H9	0.9300	O4—H4	0.8200
C10—O3	1.426 (3)
N1—C1—C13	108.57 (17)	O4—C11—C10	110.7 (2)
N1—C1—C12	106.21 (18)	O4—C11—H11A	109.5
C13—C1—C12	109.9 (2)	C10—C11—H11A	109.5
N1—C1—C2	101.00 (16)	O4—C11—H11B	109.5
C13—C1—C2	115.53 (19)	C10—C11—H11B	109.5
C12—C1—C2	114.71 (19)	H11A—C11—H11B	108.1
N2—C2—C14	109.3 (2)	C1—C12—H12A	109.5
N2—C2—C15	105.71 (19)	C1—C12—H12B	109.5
C14—C2—C15	110.4 (2)	H12A—C12—H12B	109.5
N2—C2—C1	101.41 (16)	C1—C12—H12C	109.5
C14—C2—C1	115.2 (2)	H12A—C12—H12C	109.5
C15—C2—C1	114.0 (2)	H12B—C12—H12C	109.5
N2—C3—N1	108.50 (17)	C1—C13—H13A	109.5
N2—C3—C4	126.58 (19)	C1—C13—H13B	109.5
N1—C3—C4	124.91 (18)	H13A—C13—H13B	109.5
C5—C4—C9	118.04 (18)	C1—C13—H13C	109.5
C5—C4—C3	122.21 (18)	H13A—C13—H13C	109.5
C9—C4—C3	119.75 (19)	H13B—C13—H13C	109.5
C6—C5—C4	121.61 (19)	C2—C14—H14A	109.5
C6—C5—H5	119.2	C2—C14—H14B	109.5
C4—C5—H5	119.2	H14A—C14—H14B	109.5
C5—C6—C7	119.6 (2)	C2—C14—H14C	109.5
C5—C6—H6	120.2	H14A—C14—H14C	109.5
C7—C6—H6	120.2	H14B—C14—H14C	109.5
O3—C7—C8	115.21 (18)	C2—C15—H15A	109.5
O3—C7—C6	125.3 (2)	C2—C15—H15B	109.5
C8—C7—C6	119.47 (18)	H15A—C15—H15B	109.5
C9—C8—C7	120.63 (19)	C2—C15—H15C	109.5
C9—C8—H8	119.7	H15A—C15—H15C	109.5
C7—C8—H8	119.7	H15B—C15—H15C	109.5
C8—C9—C4	120.6 (2)	O1—N1—C3	125.90 (17)
C8—C9—H9	119.7	O1—N1—C1	120.55 (17)
C4—C9—H9	119.7	C3—N1—C1	113.06 (16)
O3—C10—C11	108.08 (19)	O2—N2—C3	125.57 (17)
O3—C10—H10A	110.1	O2—N2—C2	121.12 (16)
C11—C10—H10A	110.1	C3—N2—C2	112.80 (17)
O3—C10—H10B	110.1	C7—O3—C10	118.67 (16)
C11—C10—H10B	110.1	C11—O4—H4	109.5
H10A—C10—H10B	108.4
N1—C1—C2—N2	−16.7 (2)	N2—C3—N1—O1	−177.2 (2)
C13—C1—C2—N2	−133.60 (19)	C4—C3—N1—O1	3.5 (3)
C12—C1—C2—N2	97.0 (2)	N2—C3—N1—C1	−5.2 (2)
N1—C1—C2—C14	−134.5 (2)	C4—C3—N1—C1	175.45 (19)
C13—C1—C2—C14	108.6 (2)	C13—C1—N1—O1	−51.1 (3)
C12—C1—C2—C14	−20.8 (3)	C12—C1—N1—O1	67.0 (2)
N1—C1—C2—C15	96.4 (2)	C2—C1—N1—O1	−172.97 (19)
C13—C1—C2—C15	−20.5 (3)	C13—C1—N1—C3	136.5 (2)
C12—C1—C2—C15	−149.9 (2)	C12—C1—N1—C3	−105.4 (2)
N2—C3—C4—C5	29.5 (3)	C2—C1—N1—C3	14.6 (2)
N1—C3—C4—C5	−151.3 (2)	N1—C3—N2—O2	−179.3 (2)
N2—C3—C4—C9	−149.5 (2)	C4—C3—N2—O2	0.0 (4)
N1—C3—C4—C9	29.7 (3)	N1—C3—N2—C2	−7.4 (2)
C9—C4—C5—C6	−1.3 (3)	C4—C3—N2—C2	171.86 (19)
C3—C4—C5—C6	179.6 (2)	C14—C2—N2—O2	−49.8 (3)
C4—C5—C6—C7	0.7 (4)	C15—C2—N2—O2	69.0 (3)
C5—C6—C7—O3	−179.5 (2)	C1—C2—N2—O2	−171.79 (19)
C5—C6—C7—C8	0.3 (3)	C14—C2—N2—C3	138.0 (2)
O3—C7—C8—C9	179.1 (2)	C15—C2—N2—C3	−103.3 (2)
C6—C7—C8—C9	−0.8 (3)	C1—C2—N2—C3	15.9 (2)
C7—C8—C9—C4	0.2 (3)	C8—C7—O3—C10	176.0 (2)
C5—C4—C9—C8	0.8 (3)	C6—C7—O3—C10	−4.1 (3)
C3—C4—C9—C8	179.9 (2)	C11—C10—O3—C7	177.4 (2)
O3—C10—C11—O4	60.5 (3)

Cg2 is the centroid of the benzene C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2i	0.82	2.01	2.828 (3)	173
C12—H12C···O1ii	0.96	2.54	3.418 (3)	152
C15—H15C···Cg2iii	0.96	2.80	3.570 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the benzene C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O2i	0.82	2.01	2.828 (3)	173
C12—H12C⋯O1ii	0.96	2.54	3.418 (3)	152
C15—H15C⋯Cg2iii	0.96	2.80	3.570 (3)	138

Symmetry codes: (i) ; (ii) ; (iii) .