2-[2-(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(4), the nitronyl nitroxide unit displays a twisted conformation. The crystal structure is stabilized by non-classical C-H⋯O and C-H⋯π hydrogen bonds, which build up a three-dimensional network.

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 their coordination properties, see: Masuda 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 = 14.458 (7) Å

b = 10.187 (5) Å

c = 10.670 (5) Å

V = 1571.5 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.23 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.980, T max = 0.983

10740 measured reflections

1547 independent reflections

1245 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.107

S = 1.05

1547 reflections

195 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.11 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/S1600536811050860/rk2315sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050860/rk2315Isup2.hkl

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

C15H21N2O4	F(000) = 628
Mr = 293.34	Dx = 1.240 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2696 reflections
a = 14.458 (7) Å	θ = 2.8–23.3°
b = 10.187 (5) Å	µ = 0.09 mm−1
c = 10.670 (5) Å	T = 296 K
V = 1571.5 (13) Å3	Block, red
Z = 4	0.23 × 0.20 × 0.19 mm

Bruker APEXII CCD diffractometer	1547 independent reflections
Radiation source: fine–focus sealed tube	1245 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −17→17
Tmin = 0.980, Tmax = 0.983	k = −11→12
10740 measured reflections	l = −12→12

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0518P)2 + 0.287P] where P = (Fo2 + 2Fc2)/3
1547 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.11 e Å−3
1 restraint	Δρmin = −0.14 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.9017 (2)	0.8466 (3)	0.2894 (4)	0.0611 (10)
C2	0.9954 (3)	0.9121 (4)	0.3217 (4)	0.0651 (10)
C3	0.95885 (19)	0.7595 (3)	0.4802 (3)	0.0464 (8)
C4	0.9624 (2)	0.6861 (3)	0.5974 (3)	0.0461 (7)
C5	0.8832 (3)	0.6738 (4)	0.6705 (4)	0.0636 (10)
H5	0.8274	0.7071	0.6410	0.076*
C6	0.8859 (3)	0.6144 (4)	0.7837 (5)	0.0804 (14)
H6	0.8327	0.6074	0.8321	0.097*
C7	0.9683 (3)	0.5645 (4)	0.8264 (5)	0.0793 (12)
H7	0.9705	0.5253	0.9050	0.095*
C8	1.0473 (3)	0.5710 (3)	0.7558 (4)	0.0632 (10)
H8	1.1023	0.5356	0.7858	0.076*
C9	1.0443 (2)	0.6313 (3)	0.6386 (3)	0.0469 (8)
C10	1.2080 (2)	0.6121 (4)	0.6047 (5)	0.0749 (11)
H10A	1.2186	0.5184	0.6130	0.090*
H10B	1.2165	0.6529	0.6860	0.090*
C11	1.2719 (3)	0.6687 (6)	0.5129 (5)	0.0959 (16)
H11A	1.3346	0.6439	0.5348	0.115*
H11B	1.2584	0.6322	0.4309	0.115*
C12	0.8185 (3)	0.9359 (4)	0.3095 (8)	0.115 (2)
H12A	0.7632	0.8839	0.3127	0.173*
H12B	0.8143	0.9973	0.2415	0.173*
H12C	0.8257	0.9828	0.3869	0.173*
C13	0.8961 (4)	0.7819 (5)	0.1625 (4)	0.0905 (15)
H13A	0.9469	0.7220	0.1529	0.136*
H13B	0.8991	0.8477	0.0983	0.136*
H13C	0.8389	0.7347	0.1557	0.136*
C14	0.9919 (5)	1.0609 (4)	0.3315 (6)	0.134 (3)
H14A	0.9462	1.0858	0.3924	0.201*
H14B	0.9759	1.0975	0.2515	0.201*
H14C	1.0513	1.0934	0.3570	0.201*
C15	1.0746 (3)	0.8629 (9)	0.2416 (5)	0.139 (3)
H15A	1.1323	0.8875	0.2794	0.209*
H15B	1.0704	0.9009	0.1595	0.209*
H15C	1.0713	0.7690	0.2352	0.209*
N1	0.89542 (17)	0.7436 (3)	0.3891 (3)	0.0524 (7)
N2	1.01428 (18)	0.8600 (2)	0.4494 (3)	0.0505 (7)
O1	0.83122 (15)	0.6579 (2)	0.3892 (3)	0.0682 (7)
O2	1.07936 (16)	0.9064 (2)	0.5172 (2)	0.0612 (6)
O3	1.11657 (14)	0.6369 (2)	0.5582 (2)	0.0522 (6)
O4	1.2663 (2)	0.8039 (4)	0.5064 (5)	0.1191 (15)
H4	1.2119	0.8265	0.5099	0.179*

	U11	U22	U33	U12	U13	U23
C1	0.063 (2)	0.0458 (19)	0.074 (3)	0.0010 (16)	−0.0135 (19)	0.0018 (18)
C2	0.077 (3)	0.064 (2)	0.054 (2)	−0.0238 (19)	−0.009 (2)	0.0130 (19)
C3	0.0374 (15)	0.0421 (17)	0.060 (2)	−0.0002 (13)	0.0027 (15)	−0.0036 (14)
C4	0.0460 (16)	0.0375 (16)	0.0550 (19)	−0.0034 (13)	0.0071 (15)	−0.0021 (15)
C5	0.056 (2)	0.056 (2)	0.079 (3)	−0.0072 (17)	0.0181 (19)	−0.004 (2)
C6	0.088 (3)	0.069 (3)	0.085 (3)	−0.017 (2)	0.042 (3)	0.006 (2)
C7	0.109 (3)	0.063 (2)	0.066 (2)	−0.015 (2)	0.021 (3)	0.017 (2)
C8	0.076 (2)	0.048 (2)	0.065 (2)	−0.0004 (18)	−0.001 (2)	0.0116 (18)
C9	0.0517 (18)	0.0333 (16)	0.056 (2)	−0.0035 (13)	0.0059 (16)	−0.0031 (15)
C10	0.051 (2)	0.081 (3)	0.093 (3)	0.0064 (19)	−0.005 (2)	0.010 (3)
C11	0.052 (2)	0.135 (5)	0.101 (4)	−0.002 (3)	0.002 (3)	−0.001 (3)
C12	0.091 (3)	0.071 (3)	0.184 (6)	0.027 (2)	−0.010 (4)	0.018 (4)
C13	0.118 (4)	0.084 (3)	0.070 (3)	−0.029 (3)	−0.022 (3)	0.003 (2)
C14	0.210 (6)	0.069 (3)	0.123 (4)	−0.059 (4)	−0.085 (5)	0.045 (3)
C15	0.074 (3)	0.285 (9)	0.059 (3)	−0.037 (4)	0.007 (2)	−0.004 (4)
N1	0.0412 (14)	0.0455 (15)	0.0705 (18)	−0.0027 (12)	−0.0021 (14)	−0.0004 (14)
N2	0.0514 (15)	0.0435 (14)	0.0565 (16)	−0.0070 (12)	−0.0023 (14)	0.0029 (13)
O1	0.0477 (12)	0.0592 (15)	0.0977 (19)	−0.0149 (11)	−0.0061 (14)	−0.0009 (14)
O2	0.0633 (14)	0.0583 (14)	0.0620 (14)	−0.0200 (12)	−0.0142 (13)	0.0013 (12)
O3	0.0411 (11)	0.0581 (13)	0.0573 (15)	0.0037 (10)	0.0004 (10)	−0.0029 (11)
O4	0.0635 (18)	0.130 (3)	0.164 (4)	−0.026 (2)	−0.006 (2)	0.056 (3)

C1—N1	1.498 (5)	C10—C11	1.464 (6)
C1—C13	1.508 (6)	C10—H10A	0.9700
C1—C12	1.522 (5)	C10—H10B	0.9700
C1—C2	1.550 (5)	C11—O4	1.381 (6)
C2—N2	1.488 (5)	C11—H11A	0.9700
C2—C15	1.514 (7)	C11—H11B	0.9700
C2—C14	1.520 (6)	C12—H12A	0.9600
C3—N2	1.341 (4)	C12—H12B	0.9600
C3—N1	1.346 (4)	C12—H12C	0.9600
C3—C4	1.458 (5)	C13—H13A	0.9600
C4—C9	1.381 (4)	C13—H13B	0.9600
C4—C5	1.391 (5)	C13—H13C	0.9600
C5—C6	1.352 (6)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—C7	1.372 (6)	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C7—C8	1.369 (6)	C15—H15B	0.9600
C7—H7	0.9300	C15—H15C	0.9600
C8—C9	1.394 (5)	N1—O1	1.274 (3)
C8—H8	0.9300	N2—O2	1.277 (3)
C9—O3	1.353 (4)	O4—H4	0.8200
C10—O3	1.435 (4)
N1—C1—C13	109.1 (3)	O4—C11—C10	112.9 (4)
N1—C1—C12	105.7 (4)	O4—C11—H11A	109.0
C13—C1—C12	110.2 (4)	C10—C11—H11A	109.0
N1—C1—C2	101.3 (3)	O4—C11—H11B	109.0
C13—C1—C2	115.8 (4)	C10—C11—H11B	109.0
C12—C1—C2	113.7 (3)	H11A—C11—H11B	107.8
N2—C2—C15	105.1 (4)	C1—C12—H12A	109.5
N2—C2—C14	107.4 (3)	C1—C12—H12B	109.5
C15—C2—C14	113.3 (5)	H12A—C12—H12B	109.5
N2—C2—C1	102.1 (3)	C1—C12—H12C	109.5
C15—C2—C1	113.2 (4)	H12A—C12—H12C	109.5
C14—C2—C1	114.6 (4)	H12B—C12—H12C	109.5
N2—C3—N1	108.8 (3)	C1—C13—H13A	109.5
N2—C3—C4	125.5 (3)	C1—C13—H13B	109.5
N1—C3—C4	125.6 (3)	H13A—C13—H13B	109.5
C9—C4—C5	119.4 (3)	C1—C13—H13C	109.5
C9—C4—C3	120.7 (3)	H13A—C13—H13C	109.5
C5—C4—C3	119.9 (3)	H13B—C13—H13C	109.5
C6—C5—C4	121.1 (4)	C2—C14—H14A	109.5
C6—C5—H5	119.4	C2—C14—H14B	109.5
C4—C5—H5	119.4	H14A—C14—H14B	109.5
C5—C6—C7	119.2 (4)	C2—C14—H14C	109.5
C5—C6—H6	120.4	H14A—C14—H14C	109.5
C7—C6—H6	120.4	H14B—C14—H14C	109.5
C8—C7—C6	121.5 (4)	C2—C15—H15A	109.5
C8—C7—H7	119.2	C2—C15—H15B	109.5
C6—C7—H7	119.2	H15A—C15—H15B	109.5
C7—C8—C9	119.3 (4)	C2—C15—H15C	109.5
C7—C8—H8	120.4	H15A—C15—H15C	109.5
C9—C8—H8	120.4	H15B—C15—H15C	109.5
O3—C9—C4	116.3 (3)	O1—N1—C3	125.3 (3)
O3—C9—C8	124.3 (3)	O1—N1—C1	121.7 (3)
C4—C9—C8	119.3 (3)	C3—N1—C1	112.8 (3)
O3—C10—C11	106.3 (3)	O2—N2—C3	125.7 (3)
O3—C10—H10A	110.5	O2—N2—C2	121.4 (3)
C11—C10—H10A	110.5	C3—N2—C2	112.8 (3)
O3—C10—H10B	110.5	C9—O3—C10	119.0 (3)
C11—C10—H10B	110.5	C11—O4—H4	109.5
H10A—C10—H10B	108.7
N1—C1—C2—N2	−13.7 (3)	O3—C10—C11—O4	66.3 (5)
C13—C1—C2—N2	−131.6 (3)	N2—C3—N1—O1	−179.0 (3)
C12—C1—C2—N2	99.3 (4)	C4—C3—N1—O1	−3.2 (5)
N1—C1—C2—C15	98.7 (4)	N2—C3—N1—C1	−4.4 (4)
C13—C1—C2—C15	−19.2 (5)	C4—C3—N1—C1	171.4 (3)
C12—C1—C2—C15	−148.3 (5)	C13—C1—N1—O1	−50.7 (4)
N1—C1—C2—C14	−129.4 (4)	C12—C1—N1—O1	67.9 (4)
C13—C1—C2—C14	112.7 (5)	C2—C1—N1—O1	−173.3 (3)
C12—C1—C2—C14	−16.5 (6)	C13—C1—N1—C3	134.5 (3)
N2—C3—C4—C9	−52.9 (4)	C12—C1—N1—C3	−107.0 (4)
N1—C3—C4—C9	132.0 (3)	C2—C1—N1—C3	11.9 (4)
N2—C3—C4—C5	125.4 (3)	N1—C3—N2—O2	176.5 (3)
N1—C3—C4—C5	−49.7 (4)	C4—C3—N2—O2	0.7 (5)
C9—C4—C5—C6	3.1 (5)	N1—C3—N2—C2	−5.9 (4)
C3—C4—C5—C6	−175.3 (3)	C4—C3—N2—C2	178.3 (3)
C4—C5—C6—C7	−0.6 (6)	C15—C2—N2—O2	72.3 (4)
C5—C6—C7—C8	−1.4 (7)	C14—C2—N2—O2	−48.5 (5)
C6—C7—C8—C9	0.9 (6)	C1—C2—N2—O2	−169.4 (3)
C5—C4—C9—O3	174.4 (3)	C15—C2—N2—C3	−105.4 (4)
C3—C4—C9—O3	−7.2 (4)	C14—C2—N2—C3	133.8 (4)
C5—C4—C9—C8	−3.6 (5)	C1—C2—N2—C3	12.9 (4)
C3—C4—C9—C8	174.8 (3)	C4—C9—O3—C10	164.8 (3)
C7—C8—C9—O3	−176.2 (3)	C8—C9—O3—C10	−17.3 (5)
C7—C8—C9—C4	1.7 (5)	C11—C10—O3—C9	−160.6 (3)

Cg2 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.93	2.45	3.248 (5)	143
C6—H6···O1ii	0.93	2.50	3.364 (5)	155
C14—H14B···Cg2iii	0.96	3.00	3.513 (5)	115

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.93	2.45	3.248 (5)	143
C6—H6⋯O1ii	0.93	2.50	3.364 (5)	155
C14—H14B⋯Cg2iii	0.96	3.00	3.513 (5)	115

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