4,4,5,5-Tetra-methyl-2-(3,4,5-trimethoxy-phen-yl)imidazolidine-1-oxyl 3-oxide.

In the title nitronyl nitroxide radical compound, C(16)C(23)N(2)O(5), the imidazole and benzene rings are twisted with respect to each other, making a dihedral angle of 26.2 (4)°. The imidazole ring adopts a half-chair conformation. Weak C-H⋯π inter-actions are also found.

Related literature

For the preparation of the title compound see: Ullman et al. (1974 ▶). For related structures, see: Feher et al. (2008 ▶); Gao et al. (2009 ▶); Qin et al. (2009 ▶); Cirujeda et al. (1995 ▶); Matsushita et al. (1997 ▶). For the coordination properties of the title compound and its use in the formation of mol­ecule-based magnetic materials, see: Takui et al. (2009 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C16H23N2O5

M = 323.36

Orthorhombic,

a = 20.623 (3) Å

b = 7.2168 (12) Å

c = 22.831 (4) Å

V = 3398.0 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.32 × 0.25 × 0.17 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: none

15858 measured reflections

3027 independent reflections

1519 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.119

S = 1.06

3027 reflections

216 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.23 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: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809029274/dn2472sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029274/dn2472Isup2.hkl

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

C16H23N2O5	F(000) = 1384
Mr = 323.36	Dx = 1.264 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1322 reflections
a = 20.623 (3) Å	θ = 3.1–18.2°
b = 7.2168 (12) Å	µ = 0.09 mm−1
c = 22.831 (4) Å	T = 296 K
V = 3398.0 (10) Å3	Block, blue
Z = 8	0.32 × 0.25 × 0.17 mm

Bruker SMART APEX2 diffractometer	1519 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.062
graphite	θmax = 25.1°, θmin = 1.8°
Detector resolution: 0 pixels mm-1	h = −12→24
φ and ω scans	k = −8→8
15858 measured reflections	l = −27→26
3027 independent reflections

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
3027 reflections	Δρmax = 0.17 e Å−3
216 parameters	Δρmin = −0.23 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: 0.0019 (5)

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
N1	0.06793 (9)	0.2073 (3)	0.49665 (8)	0.0570 (5)
N2	0.15280 (9)	0.0432 (3)	0.47376 (8)	0.0576 (5)
O1	0.01712 (9)	0.2652 (3)	0.52296 (7)	0.0913 (6)
O2	0.20243 (8)	−0.0630 (3)	0.47707 (7)	0.0903 (6)
O3	0.07153 (8)	0.1394 (2)	0.72841 (6)	0.0717 (5)
O4	0.12645 (7)	−0.1894 (2)	0.74689 (6)	0.0720 (5)
O5	0.17240 (8)	−0.3947 (2)	0.65885 (7)	0.0743 (5)
C1	0.08745 (10)	0.2830 (3)	0.43780 (9)	0.0511 (6)
C2	0.13132 (10)	0.1227 (3)	0.41649 (9)	0.0548 (6)
C3	0.11082 (10)	0.0839 (3)	0.51744 (9)	0.0506 (6)
C4	0.11306 (10)	0.0103 (3)	0.57690 (9)	0.0505 (6)
C5	0.14140 (10)	−0.1615 (3)	0.58697 (10)	0.0533 (6)
H5	0.1574	−0.2313	0.5559	0.064*
C6	0.14551 (10)	−0.2276 (3)	0.64375 (10)	0.0550 (6)
C7	0.12210 (10)	−0.1231 (3)	0.69035 (10)	0.0542 (6)
C8	0.09320 (11)	0.0479 (3)	0.67984 (9)	0.0543 (6)
C9	0.08840 (10)	0.1132 (3)	0.62324 (9)	0.0539 (6)
H9	0.0686	0.2266	0.6161	0.065*
C10	0.03918 (13)	0.3130 (4)	0.71996 (10)	0.0823 (8)
H10A	0.0693	0.4022	0.7047	0.123*
H10B	0.0224	0.3562	0.7567	0.123*
H10C	0.0041	0.2971	0.6928	0.123*
C11	0.18747 (13)	−0.1598 (5)	0.77318 (11)	0.1017 (10)
H11A	0.2203	−0.2234	0.7511	0.153*
H11B	0.1868	−0.2064	0.8126	0.153*
H11C	0.1968	−0.0295	0.7737	0.153*
C12	0.19952 (13)	−0.5035 (4)	0.61337 (12)	0.0869 (8)
H12A	0.1663	−0.5354	0.5857	0.130*
H12B	0.2177	−0.6146	0.6296	0.130*
H12C	0.2329	−0.4343	0.5940	0.130*
C13	0.12386 (12)	0.4629 (3)	0.45043 (11)	0.0726 (7)
H13A	0.0965	0.5449	0.4724	0.109*
H13B	0.1358	0.5209	0.4141	0.109*
H13C	0.1622	0.4360	0.4727	0.109*
C14	0.02814 (11)	0.3224 (3)	0.40075 (10)	0.0722 (7)
H14A	0.0019	0.2129	0.3984	0.108*
H14B	0.0414	0.3586	0.3621	0.108*
H14C	0.0035	0.4207	0.4183	0.108*
C15	0.18983 (12)	0.1816 (4)	0.38065 (10)	0.0783 (8)
H15A	0.2168	0.2619	0.4037	0.117*
H15B	0.1756	0.2462	0.3462	0.117*
H15C	0.2141	0.0739	0.3694	0.117*
C16	0.09402 (13)	−0.0316 (3)	0.38572 (10)	0.0765 (8)
H16A	0.1214	−0.1385	0.3818	0.115*
H16B	0.0808	0.0099	0.3476	0.115*
H16C	0.0564	−0.0633	0.4084	0.115*

	U11	U22	U33	U12	U13	U23
N1	0.0488 (12)	0.0639 (13)	0.0583 (12)	0.0123 (10)	0.0125 (10)	0.0033 (10)
N2	0.0509 (11)	0.0636 (13)	0.0583 (13)	0.0127 (11)	0.0095 (10)	0.0047 (10)
O1	0.0890 (14)	0.1057 (15)	0.0792 (11)	0.0366 (11)	0.0233 (11)	0.0175 (10)
O2	0.0745 (12)	0.1091 (15)	0.0872 (12)	0.0401 (11)	0.0215 (10)	0.0192 (10)
O3	0.0827 (13)	0.0798 (12)	0.0526 (10)	0.0157 (10)	0.0074 (8)	−0.0006 (9)
O4	0.0655 (12)	0.0913 (13)	0.0591 (11)	−0.0002 (9)	−0.0019 (9)	0.0204 (9)
O5	0.0798 (12)	0.0648 (12)	0.0783 (11)	0.0196 (10)	0.0001 (10)	0.0135 (10)
C1	0.0527 (14)	0.0518 (15)	0.0487 (13)	0.0028 (12)	0.0001 (11)	0.0055 (11)
C2	0.0590 (15)	0.0580 (15)	0.0474 (13)	0.0022 (12)	0.0058 (11)	0.0036 (12)
C3	0.0454 (13)	0.0516 (14)	0.0548 (14)	0.0060 (12)	0.0035 (12)	0.0021 (11)
C4	0.0450 (13)	0.0560 (15)	0.0504 (14)	−0.0007 (12)	0.0011 (11)	0.0049 (12)
C5	0.0475 (14)	0.0561 (16)	0.0561 (15)	0.0046 (11)	0.0013 (11)	−0.0007 (12)
C6	0.0453 (14)	0.0575 (16)	0.0623 (16)	0.0001 (12)	−0.0007 (12)	0.0082 (13)
C7	0.0478 (14)	0.0651 (17)	0.0496 (14)	−0.0037 (13)	0.0000 (11)	0.0112 (13)
C8	0.0517 (14)	0.0636 (16)	0.0474 (15)	−0.0029 (13)	0.0051 (11)	−0.0016 (12)
C9	0.0533 (14)	0.0544 (14)	0.0539 (15)	0.0038 (12)	0.0032 (11)	0.0032 (12)
C10	0.096 (2)	0.081 (2)	0.0701 (16)	0.0165 (17)	0.0143 (15)	−0.0100 (15)
C11	0.089 (2)	0.144 (3)	0.0727 (17)	−0.012 (2)	−0.0241 (17)	0.0182 (18)
C12	0.087 (2)	0.0655 (18)	0.108 (2)	0.0200 (15)	0.0072 (18)	0.0042 (16)
C13	0.0812 (19)	0.0569 (16)	0.0797 (17)	−0.0028 (14)	0.0029 (14)	0.0004 (13)
C14	0.0669 (17)	0.0819 (19)	0.0679 (15)	0.0090 (14)	−0.0072 (13)	0.0070 (14)
C15	0.0740 (19)	0.087 (2)	0.0736 (16)	0.0027 (15)	0.0289 (14)	0.0119 (14)
C16	0.097 (2)	0.0662 (17)	0.0662 (16)	−0.0037 (15)	−0.0008 (15)	−0.0077 (13)

N1—O1	1.278 (2)	C8—C9	1.379 (3)
N1—C3	1.342 (2)	C9—H9	0.9300
N1—C1	1.506 (3)	C10—H10A	0.9600
N2—O2	1.281 (2)	C10—H10B	0.9600
N2—C3	1.353 (2)	C10—H10C	0.9600
N2—C2	1.495 (3)	C11—H11A	0.9600
O3—C8	1.366 (2)	C11—H11B	0.9600
O3—C10	1.433 (3)	C11—H11C	0.9600
O4—C7	1.380 (2)	C12—H12A	0.9600
O4—C11	1.410 (3)	C12—H12B	0.9600
O5—C6	1.372 (3)	C12—H12C	0.9600
O5—C12	1.417 (3)	C13—H13A	0.9600
C1—C14	1.514 (3)	C13—H13B	0.9600
C1—C13	1.527 (3)	C13—H13C	0.9600
C1—C2	1.547 (3)	C14—H14A	0.9600
C2—C15	1.519 (3)	C14—H14B	0.9600
C2—C16	1.525 (3)	C14—H14C	0.9600
C3—C4	1.459 (3)	C15—H15A	0.9600
C4—C9	1.389 (3)	C15—H15B	0.9600
C4—C5	1.390 (3)	C15—H15C	0.9600
C5—C6	1.384 (3)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—C7	1.391 (3)	C16—H16C	0.9600
C7—C8	1.391 (3)
O1—N1—C3	126.26 (18)	O3—C10—H10A	109.5
O1—N1—C1	121.31 (18)	O3—C10—H10B	109.5
C3—N1—C1	112.36 (17)	H10A—C10—H10B	109.5
O2—N2—C3	126.70 (19)	O3—C10—H10C	109.5
O2—N2—C2	121.20 (17)	H10A—C10—H10C	109.5
C3—N2—C2	111.83 (17)	H10B—C10—H10C	109.5
C8—O3—C10	117.76 (17)	O4—C11—H11A	109.5
C7—O4—C11	113.82 (18)	O4—C11—H11B	109.5
C6—O5—C12	117.56 (18)	H11A—C11—H11B	109.5
N1—C1—C14	110.53 (17)	O4—C11—H11C	109.5
N1—C1—C13	105.77 (17)	H11A—C11—H11C	109.5
C14—C1—C13	110.08 (19)	H11B—C11—H11C	109.5
N1—C1—C2	99.52 (16)	O5—C12—H12A	109.5
C14—C1—C2	115.92 (18)	O5—C12—H12B	109.5
C13—C1—C2	114.05 (18)	H12A—C12—H12B	109.5
N2—C2—C15	110.07 (18)	O5—C12—H12C	109.5
N2—C2—C16	105.78 (18)	H12A—C12—H12C	109.5
C15—C2—C16	110.91 (19)	H12B—C12—H12C	109.5
N2—C2—C1	100.67 (16)	C1—C13—H13A	109.5
C15—C2—C1	115.15 (19)	C1—C13—H13B	109.5
C16—C2—C1	113.33 (18)	H13A—C13—H13B	109.5
N1—C3—N2	107.77 (18)	C1—C13—H13C	109.5
N1—C3—C4	126.3 (2)	H13A—C13—H13C	109.5
N2—C3—C4	125.9 (2)	H13B—C13—H13C	109.5
C9—C4—C5	120.32 (19)	C1—C14—H14A	109.5
C9—C4—C3	120.2 (2)	C1—C14—H14B	109.5
C5—C4—C3	119.5 (2)	H14A—C14—H14B	109.5
C6—C5—C4	119.2 (2)	C1—C14—H14C	109.5
C6—C5—H5	120.4	H14A—C14—H14C	109.5
C4—C5—H5	120.4	H14B—C14—H14C	109.5
O5—C6—C5	124.3 (2)	C2—C15—H15A	109.5
O5—C6—C7	115.1 (2)	C2—C15—H15B	109.5
C5—C6—C7	120.6 (2)	H15A—C15—H15B	109.5
O4—C7—C6	120.4 (2)	C2—C15—H15C	109.5
O4—C7—C8	119.8 (2)	H15A—C15—H15C	109.5
C6—C7—C8	119.9 (2)	H15B—C15—H15C	109.5
O3—C8—C9	124.9 (2)	C2—C16—H16A	109.5
O3—C8—C7	115.40 (19)	C2—C16—H16B	109.5
C9—C8—C7	119.7 (2)	H16A—C16—H16B	109.5
C8—C9—C4	120.3 (2)	C2—C16—H16C	109.5
C8—C9—H9	119.8	H16A—C16—H16C	109.5
C4—C9—H9	119.8	H16B—C16—H16C	109.5
O1—N1—C1—C14	−36.5 (3)	C2—N2—C3—C4	172.4 (2)
C3—N1—C1—C14	146.39 (19)	N1—C3—C4—C9	−26.4 (3)
O1—N1—C1—C13	82.7 (2)	N2—C3—C4—C9	151.8 (2)
C3—N1—C1—C13	−94.5 (2)	N1—C3—C4—C5	155.1 (2)
O1—N1—C1—C2	−158.87 (19)	N2—C3—C4—C5	−26.7 (3)
C3—N1—C1—C2	24.0 (2)	C9—C4—C5—C6	−0.9 (3)
O2—N2—C2—C15	−40.2 (3)	C3—C4—C5—C6	177.65 (19)
C3—N2—C2—C15	145.36 (19)	C12—O5—C6—C5	2.1 (3)
O2—N2—C2—C16	79.7 (2)	C12—O5—C6—C7	−177.4 (2)
C3—N2—C2—C16	−94.8 (2)	C4—C5—C6—O5	−179.98 (19)
O2—N2—C2—C1	−162.2 (2)	C4—C5—C6—C7	−0.5 (3)
C3—N2—C2—C1	23.4 (2)	C11—O4—C7—C6	82.3 (3)
N1—C1—C2—N2	−25.95 (19)	C11—O4—C7—C8	−98.7 (3)
C14—C1—C2—N2	−144.43 (19)	O5—C6—C7—O4	−0.3 (3)
C13—C1—C2—N2	86.2 (2)	C5—C6—C7—O4	−179.84 (19)
N1—C1—C2—C15	−144.27 (19)	O5—C6—C7—C8	−179.30 (19)
C14—C1—C2—C15	97.3 (2)	C5—C6—C7—C8	1.2 (3)
C13—C1—C2—C15	−32.1 (3)	C10—O3—C8—C9	2.5 (3)
N1—C1—C2—C16	86.5 (2)	C10—O3—C8—C7	−177.7 (2)
C14—C1—C2—C16	−31.9 (3)	O4—C7—C8—O3	0.7 (3)
C13—C1—C2—C16	−161.33 (18)	C6—C7—C8—O3	179.72 (19)
O1—N1—C3—N2	172.6 (2)	O4—C7—C8—C9	−179.5 (2)
C1—N1—C3—N2	−10.4 (2)	C6—C7—C8—C9	−0.5 (3)
O1—N1—C3—C4	−8.9 (4)	O3—C8—C9—C4	178.9 (2)
C1—N1—C3—C4	168.07 (19)	C7—C8—C9—C4	−0.9 (3)
O2—N2—C3—N1	176.8 (2)	C5—C4—C9—C8	1.6 (3)
C2—N2—C3—N1	−9.1 (2)	C3—C4—C9—C8	−176.9 (2)
O2—N2—C3—C4	−1.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···Cg2i	0.96	2.80	3.644 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯Cg2i	0.96	2.80	3.644 (2)	147

Symmetry code: (i) . Cg2 is the centroid of the phenyl ring.