Methyl 2-{[2-(4,4,5,5-tetra­methyl-1,3-dioxyl-4,5-dihydro­imidazol-2-yl)phen­yl]­oxy}acetate

Wang, H.-B.; Jing, L.-L.; Sun, X.-L.

doi:10.1107/S1600536811054018

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o217

doi:10.1107/S1600536811054018

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Methyl 2-{[2-(4,4,5,5-tetramethyl-1,3-dioxyl-4,5-dihydroimidazol-2-yl)phenyl]oxy}acetate

Hai-Bo Wang,^a Lin-Lin Jing ^b and Xiao-Li Sun ^a ^*

^aDepartment of Chemistry, School of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032, Xi-An, People's Republic of China, and ^bDepartment 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: xiaoli_sun@yahoo.cn

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

In the title compound, C₁₆H₂₁N₂O₅, 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 interactions, 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_r = 321.35
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.060
wR(F²) = 0.219
S = 0.95
3082 reflections
213 parameters
30 restraints
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.42 e Å⁻³

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) -x+1, -y+2, -z; (ii) x, y+1, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811054018/hg5154sup1.cif

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

checkCIF report

Comment top

Nitronyl nitroxides, stable organic radicals, synthesized more than 30 years ago (Osiecki et al., 1968), have received considerable attention recently because of their capability of magnetism, anticancer, antiradiation and antioxidation in biological chemistry and magnetic material fields (Soule et al. 2007).

The dihedral angle for imidazole and the phenyl rings is 88.6 (8)°. The dihedral angle is bigger than other nitronyl nitroxide reported on literature (Jing et al. 2011). In the title compound, the nitronyl nitroxide ring is almost in one plane, but the nitronyl nitroxide unit often displays a twisted or half-chair conformation for other related compounds (Wang et al.2009; Jing et al. 2011).

The crystal structure is stabilized by non-classical C—H···O and C—H···π (Table 1, Cg2 is the centroid of the phenyl ring) hydrogen bonds.

Related literature top

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 top

A mixture of 250 mg (1.0 mmol) of 2-(2'-Hydroxyl)phenyl-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl, 0.30 ml of methyl bromoacetate and 100 mg of sodium methylate in 5 ml of anhydrous tetrahydrofuran was stirred at 60°C for 5 h and TLC (CHCl₃/CH₃OH, 20:1)indicated the complete disapperance of the raw material. Then the solvent was removed to give a dark blue residue which was purified by a flash column chromatography (eluent, chloroform and methanol, the ratio ofvolume is 20 to 1) to yield the title compound as a dark red powder. Single crystals of compound were obtained from the mixed solution of n-hexaneand dichloromethane (the ratio of volume is 1 to 1).

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 for Windows (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.

Methyl 2-{[2-(4,4,5,5-tetramethyl-1,3-dioxyl- 4,5-dihydroimidazol-2-yl)phenyl]oxy}acetate top

Crystal data top

C₁₆H₂₁N₂O₅	F(000) = 684
M_r = 321.35	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.140P)²] where P = (F_o² + 2F_c²)/3
3082 reflections	(Δ/σ)_max < 0.001
213 parameters	Δρ_max = 0.42 e Å⁻³
30 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₆H₂₁N₂O₅	V = 1659.8 (16) Å³
M_r = 321.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.421 (6) Å	µ = 0.10 mm⁻¹
b = 7.381 (4) Å	T = 296 K
c = 19.700 (11) Å	0.23 × 0.21 × 0.14 mm
β = 91.832 (6)°

Data collection top

Bruker APEXII CCD diffractometer	3082 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1717 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.987	R_int = 0.049
11481 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	30 restraints
wR(F²) = 0.219	H-atom parameters constrained
S = 0.95	Δρ_max = 0.42 e Å⁻³
3082 reflections	Δρ_min = −0.42 e Å⁻³
213 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	0.2619 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₆H₂₁N₂O₅
M_r	321.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.421 (6), 7.381 (4), 19.700 (11)
β (°)	91.832 (6)
V (Å³)	1659.8 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.23 × 0.21 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.978, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	11481, 3082, 1717
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.219, 0.95
No. of reflections	3082
No. of parameters	213
No. of restraints	30
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.42

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

Hydrogen-bond geometry (Å, º) top

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

Acknowledgements

We thank the Natural Science Foundation of China (grant No. 81001398) for financial support and Yongliang Shao (Lanzhou University) for the X-ray measurements.

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Jing, L.-L., Ma, H.-P., He, L., Fan, P.-C. & Jia, Z.-P. (2011). Acta Cryst. E67, o3503. Web of Science CSD CrossRef IUCr Journals Google Scholar
Osiecki, J. H. & Ullman, E. F. (1968). J. Am. Chem. Soc. 90, 1078–1079. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soule, B. P., Hyodo, F., Matsumoto, K., Simone, N. L., Cook, J. A., Krishna, M. C. & Mitchell, J. B. (2007). Free Radic. Biol. Med. 42, 1632–1650. Web of Science CrossRef PubMed CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, H.-B., Jing, L.-L., Gao, P. & Sun, X.-L. (2009). Acta Cryst. E65, o2090. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 1| January 2012| Page o217

doi:10.1107/S1600536811054018

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

Methyl 2-{[2-(4,4,5,5-tetra­methyl-1,3-dioxyl-4,5-di­hydro­imidazol-2-yl)phen­yl]­­oxy}acetate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 2-{[2-(4,4,5,5-tetramethyl-1,3-dioxyl-4,5-dihydroimidazol-2-yl)phenyl]oxy}acetate