Dimethano-lbis[4,4,5,5-tetra-methyl-2-(5-methyl-imidazol-4-yl)-2-imidazoline-1-oxyl-3-oxide-κO,N]cobalt(II) diperchlorate.

In the mononuclear title complex, [Co(C(11)H(17)N(4)O(2))(2)(CH(3)OH)(2)](ClO(4))(2), the cobalt(II) atom lies on a symmetry centre and is coordinated by two O,N-bidentate ligands and two trans-arranged O atoms of the methanol mol-ecules in a slightly distorted octa-hedral geometry. In the crystal structure, cations and anions are linked by N-H⋯O and O-H⋯O hydrogen bonds into layers parallel to the bc plane.

Related literature

For the use of organic radicals as building blocks for the construction of new materials, see: Marvilliers et al. (1999 ▶); Yamamoto et al. (2001 ▶). For related structures, see: Chang et al. (2009 ▶); Zhang et al. (2007 ▶); Omata et al. (2001 ▶); Fokin et al. (2004 ▶); Wang et al. (2005 ▶). For the synthesis of the title compound, see: Ullman et al. (1970 ▶, 1972 ▶).

Experimental

Crystal data

[Co(C11H17N4O2)2(CH4O)2](ClO4)2

M = 796.49

Triclinic,

a = 8.761 (3) Å

b = 9.030 (3) Å

c = 11.819 (4) Å

α = 88.470 (8)°

β = 85.260 (11)°

γ = 66.638 (7)°

V = 855.4 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.73 mm−1

T = 295 K

0.21 × 0.10 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.862, T max = 0.959

7639 measured reflections

3880 independent reflections

2629 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.169

S = 1.02

3880 reflections

229 parameters

H-atom parameters constrained

Δρmax = 1.11 e Å−3

Δρmin = −0.70 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051782/rz2401sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051782/rz2401Isup2.hkl

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

[Co(C11H17N4O2)2(CH4O)2](ClO4)2	Z = 1
Mr = 796.49	F(000) = 415
Triclinic, P1	Dx = 1.546 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.761 (3) Å	Cell parameters from 1879 reflections
b = 9.030 (3) Å	θ = 2.5–23.8°
c = 11.819 (4) Å	µ = 0.73 mm−1
α = 88.470 (8)°	T = 295 K
β = 85.260 (11)°	Block, purple
γ = 66.638 (7)°	0.21 × 0.10 × 0.06 mm
V = 855.4 (5) Å3

Bruker SMART APEXII CCD area-detector diffractometer	3880 independent reflections
Radiation source: fine-focus sealed tube	2629 reflections with I > 2σ(I)
graphite	Rint = 0.035
phi and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.862, Tmax = 0.959	k = −11→11
7639 measured reflections	l = −14→15

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.099P)2] where P = (Fo2 + 2Fc2)/3
3880 reflections	(Δ/σ)max < 0.001
229 parameters	Δρmax = 1.11 e Å−3
0 restraints	Δρmin = −0.70 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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
Co1	0.5000	0.5000	0.5000	0.0314 (2)
O1	0.7069 (3)	0.5395 (3)	0.44273 (19)	0.0368 (6)
O2	0.6974 (3)	0.6104 (4)	0.0527 (2)	0.0508 (7)
O3	0.1971 (5)	0.1192 (5)	0.3303 (3)	0.0772 (10)
O4	0.3181 (5)	0.0497 (4)	0.1465 (3)	0.0735 (10)
O5	0.0366 (5)	0.1057 (6)	0.1857 (4)	0.1136 (16)
O6	0.2364 (6)	−0.1310 (4)	0.2532 (3)	0.0897 (13)
O8	0.3412 (3)	0.7434 (3)	0.4682 (2)	0.0479 (7)
H8D	0.3254	0.7810	0.4015	0.072*
N1	0.4844 (3)	0.4351 (3)	0.3332 (2)	0.0343 (6)
N2	0.4676 (4)	0.2834 (4)	0.1975 (3)	0.0405 (7)
H2	0.4357	0.2195	0.1628	0.049*
N3	0.7304 (3)	0.5838 (3)	0.3387 (2)	0.0303 (6)
N4	0.7347 (3)	0.6110 (4)	0.1542 (2)	0.0373 (7)
C1	0.5901 (4)	0.4399 (4)	0.2393 (3)	0.0314 (7)
C2	0.5821 (4)	0.3431 (4)	0.1536 (3)	0.0347 (7)
C3	0.4138 (4)	0.3410 (4)	0.3035 (3)	0.0396 (8)
H3	0.3359	0.3168	0.3498	0.048*
C4	0.6842 (4)	0.5387 (4)	0.2443 (3)	0.0313 (7)
C5	0.7972 (4)	0.7126 (4)	0.3165 (3)	0.0357 (8)
C6	0.8510 (5)	0.6844 (5)	0.1892 (3)	0.0425 (9)
C7	0.6485 (6)	0.8712 (5)	0.3436 (5)	0.0623 (12)
H7A	0.5604	0.8808	0.2970	0.094*
H7B	0.6817	0.9597	0.3287	0.094*
H7C	0.6098	0.8731	0.4222	0.094*
C8	0.9369 (5)	0.6878 (5)	0.3931 (3)	0.0502 (10)
H8A	0.8904	0.7159	0.4698	0.075*
H8B	0.9945	0.7551	0.3680	0.075*
H8C	1.0136	0.5768	0.3898	0.075*
C9	0.8249 (7)	0.8374 (6)	0.1205 (4)	0.0746 (15)
H9A	0.8636	0.8089	0.0426	0.112*
H9B	0.8863	0.8929	0.1506	0.112*
H9C	0.7084	0.9065	0.1253	0.112*
C10	1.0289 (5)	0.5579 (7)	0.1667 (4)	0.0648 (13)
H10A	1.0382	0.4590	0.2035	0.097*
H10B	1.1059	0.5960	0.1960	0.097*
H10C	1.0544	0.5393	0.0864	0.097*
C11	0.6750 (5)	0.2887 (5)	0.0407 (3)	0.0468 (9)
H11A	0.6625	0.1935	0.0170	0.070*
H11B	0.7911	0.2650	0.0462	0.070*
H11C	0.6313	0.3726	−0.0139	0.070*
C12	0.2019 (5)	0.8318 (5)	0.5434 (4)	0.0537 (10)
H12A	0.1220	0.7833	0.5454	0.081*
H12B	0.1516	0.9410	0.5176	0.081*
H12C	0.2375	0.8310	0.6181	0.081*
Cl1	0.19354 (13)	0.03724 (13)	0.22937 (9)	0.0534 (3)

	U11	U22	U33	U12	U13	U23
Co1	0.0307 (3)	0.0365 (4)	0.0318 (4)	−0.0185 (3)	−0.0037 (2)	0.0074 (3)
O1	0.0374 (12)	0.0511 (15)	0.0307 (12)	−0.0268 (11)	−0.0057 (10)	0.0070 (11)
O2	0.0599 (17)	0.0717 (19)	0.0359 (14)	−0.0412 (15)	−0.0107 (12)	0.0100 (13)
O3	0.099 (3)	0.089 (3)	0.061 (2)	−0.056 (2)	0.0030 (19)	−0.0138 (19)
O4	0.088 (2)	0.094 (3)	0.063 (2)	−0.064 (2)	0.0018 (18)	0.0024 (18)
O5	0.071 (2)	0.141 (4)	0.137 (4)	−0.044 (3)	−0.049 (3)	0.023 (3)
O6	0.156 (4)	0.072 (2)	0.071 (2)	−0.073 (3)	−0.032 (2)	0.0274 (18)
O8	0.0429 (14)	0.0436 (14)	0.0524 (16)	−0.0128 (12)	−0.0051 (12)	0.0156 (12)
N1	0.0322 (14)	0.0399 (16)	0.0360 (16)	−0.0196 (13)	−0.0053 (12)	0.0038 (12)
N2	0.0428 (16)	0.0409 (16)	0.0486 (18)	−0.0268 (14)	−0.0100 (14)	0.0006 (14)
N3	0.0323 (13)	0.0363 (14)	0.0296 (14)	−0.0213 (12)	−0.0038 (11)	0.0062 (11)
N4	0.0393 (16)	0.0487 (17)	0.0331 (15)	−0.0267 (14)	−0.0072 (12)	0.0069 (13)
C1	0.0313 (16)	0.0322 (17)	0.0339 (17)	−0.0157 (14)	−0.0055 (13)	0.0052 (13)
C2	0.0319 (16)	0.0374 (18)	0.0395 (19)	−0.0177 (15)	−0.0094 (14)	0.0042 (15)
C3	0.0339 (17)	0.044 (2)	0.048 (2)	−0.0229 (16)	−0.0082 (15)	0.0094 (17)
C4	0.0309 (16)	0.0363 (17)	0.0315 (17)	−0.0185 (14)	−0.0022 (13)	0.0035 (14)
C5	0.0372 (18)	0.0408 (19)	0.0399 (19)	−0.0267 (16)	−0.0063 (14)	0.0053 (15)
C6	0.048 (2)	0.057 (2)	0.039 (2)	−0.0388 (19)	−0.0089 (16)	0.0105 (17)
C7	0.061 (3)	0.044 (2)	0.088 (3)	−0.027 (2)	−0.003 (2)	−0.005 (2)
C8	0.053 (2)	0.067 (3)	0.050 (2)	−0.043 (2)	−0.0154 (18)	0.008 (2)
C9	0.108 (4)	0.085 (3)	0.069 (3)	−0.076 (3)	−0.032 (3)	0.040 (3)
C10	0.049 (2)	0.095 (4)	0.058 (3)	−0.039 (3)	0.010 (2)	−0.017 (3)
C11	0.049 (2)	0.052 (2)	0.042 (2)	−0.0218 (19)	−0.0002 (17)	−0.0075 (17)
C12	0.050 (2)	0.043 (2)	0.062 (3)	−0.0106 (19)	−0.012 (2)	−0.0047 (19)
Cl1	0.0628 (6)	0.0628 (6)	0.0512 (6)	−0.0409 (5)	−0.0164 (5)	0.0139 (5)

Co1—O1i	2.042 (2)	C2—C11	1.491 (5)
Co1—O1	2.042 (2)	C3—H3	0.9300
Co1—N1i	2.102 (3)	C5—C8	1.524 (5)
Co1—N1	2.102 (3)	C5—C7	1.526 (6)
Co1—O8i	2.127 (3)	C5—C6	1.537 (5)
Co1—O8	2.127 (3)	C6—C9	1.530 (5)
O1—N3	1.308 (3)	C6—C10	1.531 (6)
O2—N4	1.271 (4)	C7—H7A	0.9600
O3—Cl1	1.430 (3)	C7—H7B	0.9600
O4—Cl1	1.441 (3)	C7—H7C	0.9600
O5—Cl1	1.402 (4)	C8—H8A	0.9600
O6—Cl1	1.439 (3)	C8—H8B	0.9600
O8—C12	1.415 (5)	C8—H8C	0.9600
O8—H8D	0.8501	C9—H9A	0.9600
N1—C3	1.302 (4)	C9—H9B	0.9600
N1—C1	1.396 (4)	C9—H9C	0.9600
N2—C3	1.343 (5)	C10—H10A	0.9600
N2—C2	1.376 (4)	C10—H10B	0.9600
N2—H2	0.8600	C10—H10C	0.9600
N3—C4	1.343 (4)	C11—H11A	0.9600
N3—C5	1.504 (4)	C11—H11B	0.9600
N4—C4	1.368 (4)	C11—H11C	0.9600
N4—C6	1.506 (4)	C12—H12A	0.9600
C1—C2	1.380 (5)	C12—H12B	0.9600
C1—C4	1.440 (4)	C12—H12C	0.9600
O1i—Co1—O1	180.000 (1)	N4—C6—C9	109.6 (3)
O1i—Co1—N1i	88.12 (10)	N4—C6—C10	107.2 (3)
O1—Co1—N1i	91.88 (10)	C9—C6—C10	111.2 (4)
O1i—Co1—N1	91.88 (10)	N4—C6—C5	100.7 (3)
O1—Co1—N1	88.12 (10)	C9—C6—C5	114.9 (4)
N1i—Co1—N1	180.0	C10—C6—C5	112.4 (3)
O1i—Co1—O8i	91.60 (10)	C5—C7—H7A	109.5
O1—Co1—O8i	88.40 (10)	C5—C7—H7B	109.5
N1i—Co1—O8i	90.41 (11)	H7A—C7—H7B	109.5
N1—Co1—O8i	89.59 (11)	C5—C7—H7C	109.5
O1i—Co1—O8	88.40 (10)	H7A—C7—H7C	109.5
O1—Co1—O8	91.60 (10)	H7B—C7—H7C	109.5
N1i—Co1—O8	89.59 (11)	C5—C8—H8A	109.5
N1—Co1—O8	90.41 (11)	C5—C8—H8B	109.5
O8i—Co1—O8	180.00 (14)	H8A—C8—H8B	109.5
N3—O1—Co1	122.87 (18)	C5—C8—H8C	109.5
C12—O8—Co1	122.0 (2)	H8A—C8—H8C	109.5
C12—O8—H8D	109.8	H8B—C8—H8C	109.5
Co1—O8—H8D	122.5	C6—C9—H9A	109.5
C3—N1—C1	105.6 (3)	C6—C9—H9B	109.5
C3—N1—Co1	126.3 (2)	H9A—C9—H9B	109.5
C1—N1—Co1	125.3 (2)	C6—C9—H9C	109.5
C3—N2—C2	109.0 (3)	H9A—C9—H9C	109.5
C3—N2—H2	125.5	H9B—C9—H9C	109.5
C2—N2—H2	125.5	C6—C10—H10A	109.5
O1—N3—C4	126.8 (3)	C6—C10—H10B	109.5
O1—N3—C5	120.2 (2)	H10A—C10—H10B	109.5
C4—N3—C5	112.6 (3)	C6—C10—H10C	109.5
O2—N4—C4	125.5 (3)	H10A—C10—H10C	109.5
O2—N4—C6	123.4 (3)	H10B—C10—H10C	109.5
C4—N4—C6	111.0 (3)	C2—C11—H11A	109.5
C2—C1—N1	109.8 (3)	C2—C11—H11B	109.5
C2—C1—C4	131.0 (3)	H11A—C11—H11B	109.5
N1—C1—C4	119.2 (3)	C2—C11—H11C	109.5
N2—C2—C1	104.0 (3)	H11A—C11—H11C	109.5
N2—C2—C11	121.3 (3)	H11B—C11—H11C	109.5
C1—C2—C11	134.4 (3)	O8—C12—H12A	109.5
N1—C3—N2	111.6 (3)	O8—C12—H12B	109.5
N1—C3—H3	124.2	H12A—C12—H12B	109.5
N2—C3—H3	124.2	O8—C12—H12C	109.5
N3—C4—N4	107.6 (3)	H12A—C12—H12C	109.5
N3—C4—C1	126.3 (3)	H12B—C12—H12C	109.5
N4—C4—C1	126.1 (3)	O5—Cl1—O3	111.2 (3)
N3—C5—C8	109.8 (3)	O5—Cl1—O6	110.4 (3)
N3—C5—C7	105.0 (3)	O3—Cl1—O6	109.6 (2)
C8—C5—C7	111.4 (3)	O5—Cl1—O4	109.4 (3)
N3—C5—C6	100.1 (3)	O3—Cl1—O4	108.1 (2)
C8—C5—C6	115.5 (3)	O6—Cl1—O4	108.0 (2)
C7—C5—C6	113.8 (3)
N1i—Co1—O1—N3	−151.2 (2)	C5—N3—C4—N4	8.1 (4)
N1—Co1—O1—N3	28.8 (2)	O1—N3—C4—C1	4.0 (5)
O8i—Co1—O1—N3	118.5 (2)	C5—N3—C4—C1	−168.7 (3)
O8—Co1—O1—N3	−61.5 (2)	O2—N4—C4—N3	−172.0 (3)
O1i—Co1—O8—C12	39.5 (3)	C6—N4—C4—N3	11.4 (4)
O1—Co1—O8—C12	−140.5 (3)	O2—N4—C4—C1	4.7 (6)
N1i—Co1—O8—C12	−48.7 (3)	C6—N4—C4—C1	−171.8 (3)
N1—Co1—O8—C12	131.3 (3)	C2—C1—C4—N3	−155.3 (3)
O1i—Co1—N1—C3	−25.0 (3)	N1—C1—C4—N3	25.4 (5)
O1—Co1—N1—C3	155.0 (3)	C2—C1—C4—N4	28.5 (6)
O8i—Co1—N1—C3	66.6 (3)	N1—C1—C4—N4	−150.8 (3)
O8—Co1—N1—C3	−113.4 (3)	O1—N3—C5—C8	41.8 (4)
O1i—Co1—N1—C1	177.2 (3)	C4—N3—C5—C8	−145.0 (3)
O1—Co1—N1—C1	−2.8 (3)	O1—N3—C5—C7	−78.0 (4)
O8i—Co1—N1—C1	−91.2 (3)	C4—N3—C5—C7	95.2 (4)
O8—Co1—N1—C1	88.8 (3)	O1—N3—C5—C6	163.8 (3)
Co1—O1—N3—C4	−34.9 (4)	C4—N3—C5—C6	−23.0 (3)
Co1—O1—N3—C5	137.3 (2)	O2—N4—C6—C9	36.9 (5)
C3—N1—C1—C2	−1.0 (4)	C4—N4—C6—C9	−146.5 (4)
Co1—N1—C1—C2	160.5 (2)	O2—N4—C6—C10	−83.8 (4)
C3—N1—C1—C4	178.4 (3)	C4—N4—C6—C10	92.7 (4)
Co1—N1—C1—C4	−20.1 (4)	O2—N4—C6—C5	158.4 (3)
C3—N2—C2—C1	−0.7 (4)	C4—N4—C6—C5	−25.0 (4)
C3—N2—C2—C11	174.6 (3)	N3—C5—C6—N4	26.4 (3)
N1—C1—C2—N2	1.0 (4)	C8—C5—C6—N4	144.2 (3)
C4—C1—C2—N2	−178.3 (3)	C7—C5—C6—N4	−85.1 (3)
N1—C1—C2—C11	−173.3 (4)	N3—C5—C6—C9	144.0 (3)
C4—C1—C2—C11	7.4 (6)	C8—C5—C6—C9	−98.1 (4)
C1—N1—C3—N2	0.6 (4)	C7—C5—C6—C9	32.5 (4)
Co1—N1—C3—N2	−160.7 (2)	N3—C5—C6—C10	−87.4 (3)
C2—N2—C3—N1	0.0 (4)	C8—C5—C6—C10	30.4 (4)
O1—N3—C4—N4	−179.2 (3)	C7—C5—C6—C10	161.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4	0.86	2.18	2.988 (4)	156
O8—H8D···O6ii	0.85	1.99	2.828 (4)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4	0.86	2.18	2.988 (4)	156
O8—H8D⋯O6i	0.85	1.99	2.828 (4)	167

Symmetry code: (i) .