4,4,5,5-Tetra­methyl-2-(4-pyridyl)­imidazolidin-1-oxyl-3-oxide trichloroacetic acid solvate

Chen, H.-X.; Li, Z.-S.; Sun, B.-W.

doi:10.1107/S1600536808016085

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1197

doi:10.1107/S1600536808016085

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4,4,5,5-Tetramethyl-2-(4-pyridyl)imidazolidin-1-oxyl-3-oxide trichloroacetic acid solvate

Hong-Xian Chen,^a Zhong-Shu Li ^b and Bai-Wang Sun ^b ^*

^aDepartment of Chemistry, Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan University, Kunming 650091, People's Republic of China, and ^bOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 9 May 2008; accepted 28 May 2008; online 7 June 2008)

In the title compound, C₁₂H₁₆N₃O₂·C₂HCl₃O₂, the imidazolidine ring adopts a twist conformation. The crystal structure is stabilized by intermolecular O—H⋯N hydrogen bonds.

Related literature

For related literature, see: Zhang et al. (2006 ); Ullman et al. (1972 ); Oshio et al. (2002 ); Vostrikova et al. (2000 ).

Experimental

Crystal data

C₁₂H₁₆N₃O₂·C₂HCl₃O₂
M_r = 397.66
Monoclinic, P 2₁ /c
a = 10.003 (2) Å
b = 21.036 (4) Å
c = 9.2796 (19) Å
β = 115.33 (3)°
V = 1764.9 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.54 mm⁻¹
T = 293 (2) K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.895, T_max = 0.898
14888 measured reflections
3100 independent reflections
2041 reflections with I > 2σ(I)
R_int = 0.098

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.132
S = 1.06
3100 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4B⋯N1ⁱ	0.82	1.75	2.567 (7)	173
Symmetry code: (i) -x+2, -y, -z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016085/rz2217sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016085/rz2217Isup2.hkl

checkCIF report

Comment top

Transition metal compounds containing nitroxide radical ligands are of great interest, as these compounds play an important role in molecule-based magnetic materials (Oshio et al., 2002; Vostrikova et al., 2000). In order to investigate the crystal structure of such ligands, the title compound has been synthesized and its crystal structure is reported here.

In the title compound (Fig. 1), the imidazole ring adopts a twist conformation, with atoms C7 and C10 displaced by 0.218 (4) and 0.240 (4) Å respectively on opposite sides of the plane through atoms N2, N3, C6. The dihedral angle between the pyridine and the mean plane of the imidazole ring is 20.31 (27)°. This angle is smaller than that of 25.66 (15)° observed in the unsolvated compound (Zhang et al., 2006). In the crystal structure, an intermolecular hydrogen bonding interaction involving the hydroxyl group of the trichloroacetic acid and the N atom of the pyridine ring is observed (Table 1).

Related literature top

For related literature, see: Zhang et al. (2006); Ullman et al. (1972); Oshio et al. (2002); Vostrikova et al. (2000).

Experimental top

4,4,5,5-Tetramethyl-2-(4-pyridyl)imidazolin-1-oxyl-3-oxide was prepared according to the published method (Ullman et al., 1972). All chemicals used (reagent grade) were commercially available. 2-(4-Pyridyl)-4,4,5,5-teramethylimidazolin-1-oxyl-3-oxide (0.024 g, 0.1 mmol) was dissolved in ethanol (10 ml). Trichloroacetic acid (0.016 g, 0.1 mmol) was added slowly with stirring. The resulted solution was continuously stirred for about 30 min at room temperature and then filtered. The filtrate was slowly evaporated at room temperature over several days, to give colourless crystals suitable for X-ray analysis.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. All hydrogen atoms are omitted except for H4B. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound viewed along the b axis. Hydrogen bonds are shown as dashed lines. All hydrogen atoms are omitted except for H4B.

4,4,5,5-Tetramethyl-2-(4-pyridyl)imidazolidin-1-oxyl-3-oxide trichloroacetic acid solvate top

Crystal data top

C₁₂H₁₆N₃O₂·C₂HCl₃O₂	F(000) = 820
M_r = 397.66	D_x = 1.497 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12720 reflections
a = 10.003 (2) Å	θ = 1.0–27.6°
b = 21.036 (4) Å	µ = 0.54 mm⁻¹
c = 9.2796 (19) Å	T = 293 K
β = 115.33 (3)°	Prism, colourless
V = 1764.9 (7) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3100 independent reflections
Radiation source: fine-focus sealed tube	2041 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.098
Detector resolution: 8.192 pixels mm^-1	θ_max = 25.0°, θ_min = 2.5°
thin–slice ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −25→25
T_min = 0.895, T_max = 0.898	l = −11→11
14888 measured reflections

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0424P)² + 1.1663P] where P = (F_o² + 2F_c²)/3
3100 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₂H₁₆N₃O₂·C₂HCl₃O₂	V = 1764.9 (7) Å³
M_r = 397.66	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.003 (2) Å	µ = 0.54 mm⁻¹
b = 21.036 (4) Å	T = 293 K
c = 9.2796 (19) Å	0.20 × 0.20 × 0.20 mm
β = 115.33 (3)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3100 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2041 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.898	R_int = 0.098
14888 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.06	Δρ_max = 0.36 e Å⁻³
3100 reflections	Δρ_min = −0.26 e Å⁻³
217 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
Cl1	0.23783 (13)	0.11481 (6)	0.16145 (14)	0.0544 (4)
Cl2	0.44021 (13)	0.19710 (5)	0.40583 (14)	0.0544 (4)
Cl3	0.50692 (15)	0.06513 (6)	0.41125 (15)	0.0620 (4)
N3	1.0715 (4)	−0.17317 (15)	0.4059 (4)	0.0378 (8)
O1	0.9245 (3)	−0.03239 (13)	0.2203 (3)	0.0485 (8)
N2	0.9604 (3)	−0.08379 (15)	0.2999 (4)	0.0330 (8)
N1	1.3320 (4)	−0.10702 (18)	0.0574 (4)	0.0431 (9)
C14	0.5057 (4)	0.1426 (2)	0.1725 (5)	0.0396 (10)
C6	1.0677 (4)	−0.12466 (18)	0.3092 (4)	0.0326 (9)
O4	0.5301 (4)	0.09179 (15)	0.1183 (4)	0.0594 (9)
H4B	0.5706	0.0995	0.0598	0.089*
C3	1.1616 (4)	−0.11841 (18)	0.2243 (4)	0.0318 (9)
O2	1.1539 (4)	−0.22208 (15)	0.4388 (4)	0.0679 (10)
O3	0.5285 (4)	0.19655 (16)	0.1466 (4)	0.0700 (10)
C7	0.8677 (4)	−0.11090 (19)	0.3775 (5)	0.0365 (10)
C10	0.9750 (4)	−0.15972 (19)	0.4916 (5)	0.0363 (10)
C5	1.3255 (5)	−0.1617 (2)	0.1249 (5)	0.0456 (11)
H5A	1.3779	−0.1963	0.1134	0.055*
C13	0.4289 (4)	0.13093 (18)	0.2862 (5)	0.0369 (10)
C4	1.2440 (4)	−0.16910 (19)	0.2113 (5)	0.0396 (10)
H4A	1.2443	−0.2077	0.2604	0.048*
C2	1.1702 (5)	−0.0613 (2)	0.1541 (5)	0.0513 (12)
H2A	1.1178	−0.0260	0.1622	0.062*
C12	0.9050 (5)	−0.2207 (2)	0.5118 (6)	0.0630 (14)
H12A	0.8399	−0.2370	0.4090	0.094*
H12B	0.8498	−0.2125	0.5727	0.094*
H12C	0.9809	−0.2514	0.5667	0.094*
C9	0.7334 (5)	−0.1403 (2)	0.2419 (5)	0.0587 (13)
H9A	0.7651	−0.1739	0.1936	0.088*
H9B	0.6828	−0.1084	0.1636	0.088*
H9C	0.6677	−0.1573	0.2832	0.088*
C11	1.0795 (5)	−0.1329 (2)	0.6540 (5)	0.0599 (13)
H11A	1.1223	−0.0940	0.6393	0.090*
H11B	1.1566	−0.1631	0.7088	0.090*
H11C	1.0252	−0.1247	0.7160	0.090*
C1	1.2570 (5)	−0.0571 (2)	0.0721 (5)	0.0537 (13)
H1B	1.2633	−0.0186	0.0262	0.064*
C8	0.8203 (5)	−0.0578 (2)	0.4560 (6)	0.0582 (13)
H8A	0.9059	−0.0399	0.5413	0.087*
H8B	0.7546	−0.0744	0.4976	0.087*
H8C	0.7705	−0.0254	0.3786	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0439 (7)	0.0609 (8)	0.0638 (8)	−0.0087 (6)	0.0282 (6)	−0.0041 (6)
Cl2	0.0639 (8)	0.0492 (7)	0.0615 (8)	−0.0039 (6)	0.0378 (6)	−0.0122 (6)
Cl3	0.0845 (9)	0.0510 (7)	0.0616 (8)	0.0196 (7)	0.0417 (7)	0.0269 (6)
N3	0.043 (2)	0.0336 (19)	0.043 (2)	0.0057 (17)	0.0234 (17)	0.0060 (16)
O1	0.0541 (19)	0.0439 (18)	0.059 (2)	0.0196 (15)	0.0354 (16)	0.0186 (15)
N2	0.0348 (19)	0.0324 (19)	0.034 (2)	0.0051 (16)	0.0171 (16)	0.0023 (15)
N1	0.042 (2)	0.053 (2)	0.041 (2)	0.0010 (19)	0.0237 (18)	−0.0032 (18)
C14	0.032 (2)	0.052 (3)	0.037 (3)	0.001 (2)	0.016 (2)	0.007 (2)
C6	0.034 (2)	0.034 (2)	0.031 (2)	0.004 (2)	0.0153 (19)	0.0018 (18)
O4	0.071 (2)	0.069 (2)	0.061 (2)	0.0061 (19)	0.0502 (19)	−0.0005 (17)
C3	0.031 (2)	0.036 (2)	0.028 (2)	0.0002 (19)	0.0128 (18)	−0.0016 (17)
O2	0.082 (2)	0.053 (2)	0.093 (3)	0.0336 (19)	0.061 (2)	0.0324 (18)
O3	0.100 (3)	0.055 (2)	0.077 (3)	−0.011 (2)	0.058 (2)	0.0171 (18)
C7	0.030 (2)	0.044 (3)	0.042 (3)	0.001 (2)	0.022 (2)	0.000 (2)
C10	0.036 (2)	0.043 (3)	0.035 (2)	−0.001 (2)	0.021 (2)	0.0006 (19)
C5	0.037 (2)	0.046 (3)	0.061 (3)	0.003 (2)	0.027 (2)	−0.012 (2)
C13	0.041 (2)	0.033 (2)	0.043 (3)	0.0003 (19)	0.024 (2)	0.0059 (19)
C4	0.043 (3)	0.030 (2)	0.052 (3)	0.000 (2)	0.026 (2)	−0.0032 (19)
C2	0.060 (3)	0.049 (3)	0.062 (3)	0.019 (2)	0.043 (3)	0.016 (2)
C12	0.061 (3)	0.057 (3)	0.084 (4)	0.000 (3)	0.044 (3)	0.019 (3)
C9	0.036 (3)	0.079 (4)	0.051 (3)	−0.012 (3)	0.010 (2)	0.005 (3)
C11	0.055 (3)	0.075 (4)	0.045 (3)	0.007 (3)	0.017 (2)	0.002 (2)
C1	0.065 (3)	0.055 (3)	0.058 (3)	0.017 (3)	0.041 (3)	0.023 (2)
C8	0.064 (3)	0.065 (3)	0.064 (3)	0.012 (3)	0.045 (3)	0.007 (3)

Geometric parameters (Å, º) top

Cl1—C13	1.793 (4)	C10—C12	1.512 (6)
Cl2—C13	1.754 (4)	C10—C11	1.528 (6)
Cl3—C13	1.760 (4)	C5—C4	1.375 (5)
N3—O2	1.271 (4)	C5—H5A	0.9300
N3—C6	1.349 (5)	C4—H4A	0.9300
N3—C10	1.517 (5)	C2—C1	1.381 (5)
O1—N2	1.272 (4)	C2—H2A	0.9300
N2—C6	1.349 (5)	C12—H12A	0.9600
N2—C7	1.508 (5)	C12—H12B	0.9600
N1—C5	1.324 (5)	C12—H12C	0.9600
N1—C1	1.331 (5)	C9—H9A	0.9600
C14—O3	1.202 (5)	C9—H9B	0.9600
C14—O4	1.249 (5)	C9—H9C	0.9600
C14—C13	1.568 (5)	C11—H11A	0.9600
C6—C3	1.467 (5)	C11—H11B	0.9600
O4—H4B	0.8200	C11—H11C	0.9600
C3—C4	1.385 (5)	C1—H1B	0.9300
C3—C2	1.387 (5)	C8—H8A	0.9600
C7—C8	1.516 (5)	C8—H8B	0.9600
C7—C9	1.525 (6)	C8—H8C	0.9600
C7—C10	1.535 (6)

O2—N3—C6	127.0 (3)	Cl2—C13—Cl1	108.7 (2)
O2—N3—C10	121.2 (3)	Cl3—C13—Cl1	109.1 (2)
C6—N3—C10	111.4 (3)	C5—C4—C3	119.1 (4)
O1—N2—C6	126.8 (3)	C5—C4—H4A	120.4
O1—N2—C7	121.3 (3)	C3—C4—H4A	120.4
C6—N2—C7	111.3 (3)	C1—C2—C3	119.6 (4)
C5—N1—C1	119.5 (3)	C1—C2—H2A	120.2
O3—C14—O4	129.9 (4)	C3—C2—H2A	120.2
O3—C14—C13	118.1 (4)	C10—C12—H12A	109.5
O4—C14—C13	111.9 (4)	C10—C12—H12B	109.5
N3—C6—N2	108.6 (3)	H12A—C12—H12B	109.5
N3—C6—C3	125.7 (3)	C10—C12—H12C	109.5
N2—C6—C3	125.7 (3)	H12A—C12—H12C	109.5
C14—O4—H4B	109.5	H12B—C12—H12C	109.5
C4—C3—C2	117.9 (4)	C7—C9—H9A	109.5
C4—C3—C6	121.3 (3)	C7—C9—H9B	109.5
C2—C3—C6	120.8 (3)	H9A—C9—H9B	109.5
N2—C7—C8	109.4 (3)	C7—C9—H9C	109.5
N2—C7—C9	105.3 (3)	H9A—C9—H9C	109.5
C8—C7—C9	110.4 (4)	H9B—C9—H9C	109.5
N2—C7—C10	101.0 (3)	C10—C11—H11A	109.5
C8—C7—C10	115.6 (3)	C10—C11—H11B	109.5
C9—C7—C10	114.0 (3)	H11A—C11—H11B	109.5
C12—C10—N3	109.8 (3)	C10—C11—H11C	109.5
C12—C10—C11	110.4 (4)	H11A—C11—H11C	109.5
N3—C10—C11	105.4 (3)	H11B—C11—H11C	109.5
C12—C10—C7	115.4 (3)	N1—C1—C2	121.4 (4)
N3—C10—C7	100.2 (3)	N1—C1—H1B	119.3
C11—C10—C7	114.5 (3)	C2—C1—H1B	119.3
N1—C5—C4	122.4 (4)	C7—C8—H8A	109.5
N1—C5—H5A	118.8	C7—C8—H8B	109.5
C4—C5—H5A	118.8	H8A—C8—H8B	109.5
C14—C13—Cl2	112.6 (3)	C7—C8—H8C	109.5
C14—C13—Cl3	111.1 (3)	H8A—C8—H8C	109.5
Cl2—C13—Cl3	108.5 (2)	H8B—C8—H8C	109.5
C14—C13—Cl1	106.8 (3)

O2—N3—C6—N2	177.0 (4)	N2—C7—C10—C12	−143.3 (3)
C10—N3—C6—N2	−9.8 (4)	C8—C7—C10—C12	98.8 (4)
O2—N3—C6—C3	−1.2 (7)	C9—C7—C10—C12	−30.8 (5)
C10—N3—C6—C3	172.0 (3)	N2—C7—C10—N3	−25.4 (3)
O1—N2—C6—N3	179.8 (3)	C8—C7—C10—N3	−143.4 (3)
C7—N2—C6—N3	−9.0 (4)	C9—C7—C10—N3	87.0 (4)
O1—N2—C6—C3	−2.0 (6)	N2—C7—C10—C11	86.8 (4)
C7—N2—C6—C3	169.3 (4)	C8—C7—C10—C11	−31.1 (5)
N3—C6—C3—C4	13.2 (6)	C9—C7—C10—C11	−160.7 (4)
N2—C6—C3—C4	−164.8 (4)	C1—N1—C5—C4	−0.3 (6)
N3—C6—C3—C2	−166.9 (4)	O3—C14—C13—Cl2	−18.8 (5)
N2—C6—C3—C2	15.1 (6)	O4—C14—C13—Cl2	163.2 (3)
O1—N2—C7—C8	−43.0 (5)	O3—C14—C13—Cl3	−140.6 (4)
C6—N2—C7—C8	145.2 (3)	O4—C14—C13—Cl3	41.3 (4)
O1—N2—C7—C9	75.8 (4)	O3—C14—C13—Cl1	100.5 (4)
C6—N2—C7—C9	−96.0 (4)	O4—C14—C13—Cl1	−77.5 (4)
O1—N2—C7—C10	−165.3 (3)	N1—C5—C4—C3	2.2 (6)
C6—N2—C7—C10	22.9 (4)	C2—C3—C4—C5	−2.6 (6)
O2—N3—C10—C12	−41.2 (5)	C6—C3—C4—C5	177.3 (4)
C6—N3—C10—C12	145.1 (4)	C4—C3—C2—C1	1.2 (6)
O2—N3—C10—C11	77.7 (4)	C6—C3—C2—C1	−178.7 (4)
C6—N3—C10—C11	−95.9 (4)	C5—N1—C1—C2	−1.1 (7)
O2—N3—C10—C7	−163.1 (4)	C3—C2—C1—N1	0.7 (7)
C6—N3—C10—C7	23.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···N1ⁱ	0.82	1.75	2.567 (7)	173

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₆N₃O₂·C₂HCl₃O₂
M_r	397.66
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.003 (2), 21.036 (4), 9.2796 (19)
β (°)	115.33 (3)
V (Å³)	1764.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.54
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.895, 0.898
No. of measured, independent and observed [I > 2σ(I)] reflections	14888, 3100, 2041
R_int	0.098
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.132, 1.06
No. of reflections	3100
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.26

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···N1ⁱ	0.82	1.75	2.567 (7)	173

Symmetry code: (i) −x+2, −y, −z.

References

Oshio, H., Yamamoto, M. & Ito, T. (2002). Inorg. Chem. 41, 5817–5820. Web of Science CSD CrossRef PubMed CAS Google Scholar
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ullman, E. F., Osiecki, J. H., Boocock, D. G. B. & Darcy, R. (1972). J. Am. Chem. Soc. , 94, 7049–7059. CrossRef CAS Web of Science Google Scholar
Vostrikova, K. E., Luneau, D., Wernsdorfer, W., Rey, P. & Verdaguer, M. (2000). J. Am. Chem. Soc. 122, 718–719. Web of Science CSD CrossRef CAS Google Scholar
Zhang, C.-X., Sun, D.-L. & Wang, X.-C. (2006). Acta Cryst. E62, o5666–o5667. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 7| July 2008| Page o1197

doi:10.1107/S1600536808016085

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

4,4,5,5-Tetra­methyl-2-(4-pyridyl)­imidazolidin-1-oxyl-3-oxide tri­chloro­acetic acid solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

4,4,5,5-Tetramethyl-2-(4-pyridyl)imidazolidin-1-oxyl-3-oxide trichloroacetic acid solvate