Methyl 2-{[2-(4,4,5,5-tetra-methyl-1,3-dioxyl-4,5-dihydro-imidazol-2-yl)phen-yl]-oxy}acetate.

In the title compound, C(16)H(21)N(2)O(5), the benzene ring is nearly perpendicular to the imidazole ring, making a torsion angle of 88.6 (8)°·The crystal structure is stabilized by non-classical C-H⋯O and C-H⋯π inter-actions, which build up a three-dimensional network.

Related literature

For the chemical and physical properties of nitronyl nitroxides, see: Osiecki & Ullman (1968 ▶). For their biological activity, see: Soule et al. (2007 ▶). For related structures, see: Wang et al. (2009 ▶); Jing et al. (2011 ▶).

Experimental

Crystal data

C16H21N2O5

M = 321.35

Monoclinic,

a = 11.421 (6) Å

b = 7.381 (4) Å

c = 19.700 (11) Å

β = 91.832 (6)°

V = 1659.8 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.23 × 0.21 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.978, T max = 0.987

11481 measured reflections

3082 independent reflections

1717 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.219

S = 0.95

3082 reflections

213 parameters

30 restraints

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.42 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 for Windows (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/S1600536811054018/hg5154sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054018/hg5154Isup2.hkl

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

C16H21N2O5	F(000) = 684
Mr = 321.35	Dx = 1.286 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1441 reflections
a = 11.421 (6) Å	θ = 2.7–20.5°
b = 7.381 (4) Å	µ = 0.10 mm−1
c = 19.700 (11) Å	T = 296 K
β = 91.832 (6)°	Block, red
V = 1659.8 (16) Å3	0.23 × 0.21 × 0.14 mm
Z = 4

Bruker APEXII CCD diffractometer	3082 independent reflections
Radiation source: fine-focus sealed tube	1717 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ and ω scans	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −13→13
Tmin = 0.978, Tmax = 0.987	k = −8→8
11481 measured reflections	l = −23→21

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.219	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.140P)2] where P = (Fo2 + 2Fc2)/3
3082 reflections	(Δ/σ)max < 0.001
213 parameters	Δρmax = 0.42 e Å−3
30 restraints	Δρmin = −0.42 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	0.2619 (4)	1.4589 (6)	−0.1296 (2)	0.0838 (13)
H1A	0.2219	1.3511	−0.1447	0.126*
H1B	0.2999	1.5138	−0.1673	0.126*
H1C	0.2065	1.5424	−0.1117	0.126*
C2	0.3169 (3)	1.2963 (5)	−0.03053 (17)	0.0527 (9)
C3	0.4199 (3)	1.2593 (4)	0.01652 (17)	0.0524 (9)
H3A	0.4869	1.2222	−0.0092	0.063*
H3B	0.4409	1.3678	0.0419	0.063*
C4	0.4695 (3)	1.0655 (4)	0.10896 (18)	0.0509 (9)
C5	0.5846 (3)	1.1206 (5)	0.1134 (2)	0.0616 (10)
H5	0.6130	1.2036	0.0825	0.074*
C6	0.6575 (3)	1.0515 (5)	0.1642 (2)	0.0705 (11)
H6	0.7353	1.0887	0.1670	0.085*
C7	0.6184 (3)	0.9304 (5)	0.2103 (2)	0.0749 (12)
H7	0.6684	0.8865	0.2446	0.090*
C8	0.5027 (3)	0.8732 (5)	0.2053 (2)	0.0667 (11)
H8	0.4753	0.7893	0.2362	0.080*
C9	0.4280 (3)	0.9395 (4)	0.15493 (18)	0.0505 (9)
C10	0.3067 (3)	0.8761 (4)	0.14568 (16)	0.0461 (8)
C11	0.1010 (3)	0.8621 (4)	0.14948 (16)	0.0476 (8)
C12	0.1454 (3)	0.7110 (4)	0.10154 (17)	0.0505 (9)
C13	0.0269 (4)	1.0061 (6)	0.1154 (2)	0.0898 (14)
H13A	0.0068	1.0963	0.1482	0.135*
H13B	−0.0434	0.9523	0.0965	0.135*
H13C	0.0699	1.0616	0.0798	0.135*
C14	0.0445 (5)	0.7921 (6)	0.2134 (2)	0.1018 (17)
H14A	0.0916	0.6966	0.2330	0.153*
H14B	−0.0324	0.7465	0.2020	0.153*
H14C	0.0385	0.8891	0.2456	0.153*
C15	0.1063 (6)	0.7353 (9)	0.0277 (2)	0.124 (2)
H15A	0.1267	0.8547	0.0129	0.186*
H15B	0.0230	0.7195	0.0233	0.186*
H15C	0.1445	0.6470	0.0003	0.186*
C16	0.1231 (4)	0.5185 (5)	0.1239 (3)	0.0999 (17)
H16A	0.1644	0.4363	0.0954	0.150*
H16B	0.0407	0.4934	0.1203	0.150*
H16C	0.1501	0.5035	0.1702	0.150*
N1	0.2724 (2)	0.7420 (4)	0.10481 (18)	0.0709 (10)
N2	0.2136 (2)	0.9510 (4)	0.17210 (14)	0.0554 (8)
O1	0.3482 (2)	1.4130 (3)	−0.07761 (13)	0.0671 (8)
O2	0.2212 (2)	1.2324 (4)	−0.02691 (14)	0.0769 (9)
O3	0.38813 (19)	1.1206 (3)	0.06102 (13)	0.0623 (7)
O4	0.3397 (3)	0.6491 (5)	0.0681 (2)	0.1186 (12)
O5	0.2140 (2)	1.0877 (5)	0.21176 (16)	0.1025 (12)

	U11	U22	U33	U12	U13	U23
C1	0.102 (3)	0.079 (3)	0.069 (3)	−0.011 (2)	−0.021 (2)	0.010 (2)
C2	0.053 (2)	0.052 (2)	0.053 (2)	−0.0063 (16)	0.0076 (16)	−0.0013 (17)
C3	0.0467 (18)	0.049 (2)	0.061 (2)	−0.0090 (15)	0.0073 (16)	0.0017 (17)
C4	0.0395 (17)	0.053 (2)	0.060 (2)	−0.0063 (15)	0.0010 (16)	0.0017 (17)
C5	0.046 (2)	0.058 (2)	0.080 (3)	−0.0111 (16)	0.0016 (18)	0.002 (2)
C6	0.046 (2)	0.063 (3)	0.101 (3)	−0.0059 (18)	−0.011 (2)	−0.003 (2)
C7	0.062 (2)	0.062 (2)	0.100 (3)	0.0017 (19)	−0.022 (2)	0.007 (2)
C8	0.067 (2)	0.058 (2)	0.075 (3)	−0.0052 (18)	−0.008 (2)	0.013 (2)
C9	0.0442 (17)	0.049 (2)	0.058 (2)	−0.0058 (15)	0.0019 (16)	−0.0013 (17)
C10	0.0486 (18)	0.0436 (19)	0.0463 (19)	−0.0044 (15)	0.0057 (15)	0.0049 (16)
C11	0.0458 (17)	0.0477 (19)	0.0496 (19)	−0.0064 (14)	0.0043 (14)	0.0001 (16)
C12	0.0446 (17)	0.054 (2)	0.053 (2)	−0.0072 (15)	0.0036 (15)	−0.0041 (17)
C13	0.084 (3)	0.071 (3)	0.112 (3)	0.021 (2)	−0.037 (3)	−0.017 (3)
C14	0.135 (4)	0.087 (3)	0.087 (3)	−0.029 (3)	0.064 (3)	−0.011 (3)
C15	0.146 (5)	0.161 (5)	0.065 (3)	0.050 (4)	−0.009 (3)	−0.027 (3)
C16	0.094 (3)	0.054 (3)	0.155 (5)	−0.019 (2)	0.056 (3)	−0.017 (3)
N1	0.0510 (16)	0.0576 (18)	0.106 (2)	−0.0131 (14)	0.0310 (16)	−0.0363 (17)
N2	0.0490 (16)	0.0664 (19)	0.0506 (17)	−0.0029 (14)	0.0012 (13)	−0.0165 (15)
O1	0.0691 (16)	0.0705 (17)	0.0612 (16)	−0.0152 (13)	−0.0052 (13)	0.0127 (13)
O2	0.0480 (15)	0.094 (2)	0.089 (2)	−0.0201 (14)	−0.0036 (13)	0.0184 (16)
O3	0.0472 (13)	0.0689 (17)	0.0704 (16)	−0.0189 (11)	−0.0041 (11)	0.0219 (13)
O4	0.0707 (18)	0.099 (2)	0.189 (3)	−0.0214 (15)	0.0467 (19)	−0.074 (2)
O5	0.076 (2)	0.124 (3)	0.107 (2)	−0.0052 (17)	−0.0016 (17)	−0.075 (2)

C1—O1	1.439 (5)	C10—N1	1.328 (4)
C1—H1A	0.9600	C11—N2	1.498 (4)
C1—H1B	0.9600	C11—C13	1.503 (5)
C1—H1C	0.9600	C11—C14	1.524 (5)
C2—O2	1.194 (4)	C11—C12	1.557 (4)
C2—O1	1.324 (4)	C12—N1	1.468 (4)
C2—C3	1.500 (5)	C12—C16	1.512 (5)
C3—O3	1.403 (4)	C12—C15	1.518 (6)
C3—H3A	0.9700	C13—H13A	0.9600
C3—H3B	0.9700	C13—H13B	0.9600
C4—O3	1.365 (4)	C13—H13C	0.9600
C4—C5	1.376 (4)	C14—H14A	0.9600
C4—C9	1.392 (5)	C14—H14B	0.9600
C5—C6	1.378 (5)	C14—H14C	0.9600
C5—H5	0.9300	C15—H15A	0.9600
C6—C7	1.360 (5)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—C8	1.388 (5)	C16—H16A	0.9600
C7—H7	0.9300	C16—H16B	0.9600
C8—C9	1.377 (5)	C16—H16C	0.9600
C8—H8	0.9300	N1—O4	1.272 (4)
C9—C10	1.468 (4)	N2—O5	1.276 (4)
C10—N2	1.320 (4)
O1—C1—H1A	109.5	C13—C11—C12	115.2 (3)
O1—C1—H1B	109.5	C14—C11—C12	114.4 (3)
H1A—C1—H1B	109.5	N1—C12—C16	108.0 (3)
O1—C1—H1C	109.5	N1—C12—C15	106.5 (3)
H1A—C1—H1C	109.5	C16—C12—C15	110.1 (4)
H1B—C1—H1C	109.5	N1—C12—C11	101.7 (2)
O2—C2—O1	124.6 (3)	C16—C12—C11	115.8 (3)
O2—C2—C3	126.3 (3)	C15—C12—C11	113.9 (3)
O1—C2—C3	109.1 (3)	C11—C13—H13A	109.5
O3—C3—C2	107.8 (3)	C11—C13—H13B	109.5
O3—C3—H3A	110.2	H13A—C13—H13B	109.5
C2—C3—H3A	110.2	C11—C13—H13C	109.5
O3—C3—H3B	110.2	H13A—C13—H13C	109.5
C2—C3—H3B	110.2	H13B—C13—H13C	109.5
H3A—C3—H3B	108.5	C11—C14—H14A	109.5
O3—C4—C5	125.7 (3)	C11—C14—H14B	109.5
O3—C4—C9	114.3 (3)	H14A—C14—H14B	109.5
C5—C4—C9	120.0 (3)	C11—C14—H14C	109.5
C4—C5—C6	119.4 (4)	H14A—C14—H14C	109.5
C4—C5—H5	120.3	H14B—C14—H14C	109.5
C6—C5—H5	120.3	C12—C15—H15A	109.5
C7—C6—C5	121.6 (3)	C12—C15—H15B	109.5
C7—C6—H6	119.2	H15A—C15—H15B	109.5
C5—C6—H6	119.2	C12—C15—H15C	109.5
C6—C7—C8	119.0 (4)	H15A—C15—H15C	109.5
C6—C7—H7	120.5	H15B—C15—H15C	109.5
C8—C7—H7	120.5	C12—C16—H16A	109.5
C9—C8—C7	120.6 (4)	C12—C16—H16B	109.5
C9—C8—H8	119.7	H16A—C16—H16B	109.5
C7—C8—H8	119.7	C12—C16—H16C	109.5
C8—C9—C4	119.4 (3)	H16A—C16—H16C	109.5
C8—C9—C10	122.4 (3)	H16B—C16—H16C	109.5
C4—C9—C10	118.1 (3)	O4—N1—C10	125.1 (3)
N2—C10—N1	109.0 (3)	O4—N1—C12	120.3 (3)
N2—C10—C9	125.9 (3)	C10—N1—C12	114.5 (3)
N1—C10—C9	124.9 (3)	O5—N2—C10	125.8 (3)
N2—C11—C13	106.8 (3)	O5—N2—C11	121.0 (3)
N2—C11—C14	106.5 (3)	C10—N2—C11	113.2 (3)
C13—C11—C14	111.2 (3)	C2—O1—C1	117.2 (3)
N2—C11—C12	101.6 (2)	C4—O3—C3	117.7 (2)
O2—C2—C3—O3	6.6 (5)	N2—C10—N1—O4	175.5 (4)
O1—C2—C3—O3	−173.5 (3)	C9—C10—N1—O4	0.3 (6)
O3—C4—C5—C6	−179.1 (3)	N2—C10—N1—C12	−1.5 (4)
C9—C4—C5—C6	−0.8 (5)	C9—C10—N1—C12	−176.7 (3)
C4—C5—C6—C7	−0.2 (6)	C16—C12—N1—O4	61.9 (5)
C5—C6—C7—C8	1.0 (6)	C15—C12—N1—O4	−56.3 (5)
C6—C7—C8—C9	−0.7 (6)	C11—C12—N1—O4	−175.8 (4)
C7—C8—C9—C4	−0.3 (6)	C16—C12—N1—C10	−121.0 (4)
C7—C8—C9—C10	176.9 (3)	C15—C12—N1—C10	120.8 (4)
O3—C4—C9—C8	179.5 (3)	C11—C12—N1—C10	1.4 (4)
C5—C4—C9—C8	1.1 (5)	N1—C10—N2—O5	−177.4 (3)
O3—C4—C9—C10	2.2 (5)	C9—C10—N2—O5	−2.3 (6)
C5—C4—C9—C10	−176.2 (3)	N1—C10—N2—C11	1.0 (4)
C8—C9—C10—N2	93.2 (5)	C9—C10—N2—C11	176.1 (3)
C4—C9—C10—N2	−89.6 (4)	C13—C11—N2—O5	57.3 (4)
C8—C9—C10—N1	−92.4 (5)	C14—C11—N2—O5	−61.6 (4)
C4—C9—C10—N1	84.8 (4)	C12—C11—N2—O5	178.3 (3)
N2—C11—C12—N1	−0.7 (3)	C13—C11—N2—C10	−121.2 (3)
C13—C11—C12—N1	114.3 (3)	C14—C11—N2—C10	119.9 (3)
C14—C11—C12—N1	−115.0 (4)	C12—C11—N2—C10	−0.1 (3)
N2—C11—C12—C16	116.1 (3)	O2—C2—O1—C1	−3.0 (5)
C13—C11—C12—C16	−128.9 (4)	C3—C2—O1—C1	177.1 (3)
C14—C11—C12—C16	1.7 (5)	C5—C4—O3—C3	−7.2 (5)
N2—C11—C12—C15	−114.8 (4)	C9—C4—O3—C3	174.5 (3)
C13—C11—C12—C15	0.2 (5)	C2—C3—O3—C4	−179.6 (3)
C14—C11—C12—C15	130.9 (4)

Cg2 is the centroid of the phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O4i	0.97	2.51	3.327 (5)	141
C3—H3B···O4ii	0.97	2.44	3.195 (5)	134
C8—H8···Cg2iii	0.93	2.99	3.896 (5)	164

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O4i	0.97	2.51	3.327 (5)	141
C3—H3B⋯O4ii	0.97	2.44	3.195 (5)	134
C8—H8⋯Cg2iii	0.93	2.99	3.896 (5)	164

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