Dimethano­lbis[4,4,5,5-tetra­methyl-2-(5-methyl­imidazol-4-yl)-2-imidazoline-1-oxyl-3-oxide-κ2O,N]cobalt(II) diperchlorate

Gao, Z.Y.; Guo, H.J.; Zhang, W.B.

doi:10.1107/S1600536809051782

Dimethanolbis[4,4,5,5-tetramethyl-2-(5-methylimidazol-4-yl)-2-imidazoline-1-oxyl-3-oxide-κ²O,N]cobalt(II) diperchlorate

In the mononuclear title complex, [Co(C₁₁H₁₇N₄O₂)₂(CH₃OH)₂](ClO₄)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 molecules in a slightly distorted octahedral 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809051782/rz2401sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809051782/rz2401Isup2.hkl Contains datablock I

CCDC reference: 766648

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.006 Å
R factor = 0.058
wR factor = 0.169
Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         18
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors of         Cl1
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         45

Alert level G
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Engineering of molecular magnets constitutes a major research goal and has spawned interest in organic radicals as building blocks for construction of new materials (Marvilliers et al., 1999; Yamamoto et al., 2001). In this field, nitronyl nitroxides acting as useful paramagnetic building blocks have been extensively used to assemble molecular magnetic materials, because many of them are good stable spin carriers even when coordinated to metal ions. Various substitutions on radical ligands can lead to large change in not only coordination modes but also electronic behaviours, so a large number of investigations on various properties of metal-radicals complexes have been carried out and aroused intense interest and far-ranging studies (Chang et al., 2009; Zhang et al., 2007; Omata et al., 2001; Fokin et al., 2004; Wang et al., 2005). In this article, we report the synthesis and crystal structure of a novel cobalt(II) complex with the nitronyl nitroxide radical.

The crystal structure of the title compound is shown in Figure. 1. The cobalt(II) ion lies on a symmetry centre and is six-coordinate in a slightly distorted octahedral CoN₄O₂ environment provided by two O,N-bidentate ligands and two trans-arranged oxygen atoms of methanol molecules. The Co1/O1/N3/C4/C1/N1 six-membered chelatating ring assumes a half-boat conformation, with atoms O1 and C1 displaced by 0.402 (3) and 0.195 (3) Å, respectively, from the mean plane of the other atoms. In the crystal structure, cations and anions are linked by N—H···O and O—H···O hydrogen bonds (Table 1) into layers parallel to the bc plane.

Related literature top

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 top

The nitronyl nitroxide radical (4,4,5,5-tetramethyl-2-(5-methylimidazol-4-yl)-2-imidazoline-1-oxyl-3-oxide) was synthesized according to the literature procedures (Ullman et al., 1970; Ullman et al., 1972). The complex was synthesized by mixing 5 ml of a methanol solution of nitronyl nitroxide radical (0.4 mmol) and 5 ml of a methanol solution of Co(ClO₄)₂.6H₂O (0.2 mmol). After stirring for two hours at room temperature, the mixture solution was filtered. The clear deep purple filtrate was diffused with diethyl ether vapour at room temperature for two days, to afford deep purple crystals suitable for X-ray analysis.

Computing details top

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

Figures top

Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. Unlabelled atoms are generated by the symmetry operation (-x+1,-y+1,-z+1).

Dimethanolbis[4,4,5,5-tetramethyl-2-(5-methylimidazol-4-yl)-2- imidazoline-1-oxyl-3-oxide-κ²O,N]cobalt(II) diperchlorate top

Crystal data top

[Co(C₁₁H₁₇N₄O₂)₂(CH₄O)₂](ClO₄)₂	Z = 1
M_r = 796.49	F(000) = 415
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.169	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.099P)²] where P = (F_o² + 2F_c²)/3
3880 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 1.11 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

[Co(C₁₁H₁₇N₄O₂)₂(CH₄O)₂](ClO₄)₂	γ = 66.638 (7)°
M_r = 796.49	V = 855.4 (5) Å³
Triclinic, P1	Z = 1
a = 8.761 (3) Å	Mo Kα radiation
b = 9.030 (3) Å	µ = 0.73 mm⁻¹
c = 11.819 (4) Å	T = 295 K
α = 88.470 (8)°	0.21 × 0.10 × 0.06 mm
β = 85.260 (11)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3880 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2629 reflections with I > 2σ(I)
T_min = 0.862, T_max = 0.959	R_int = 0.035
7639 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.169	H-atom parameters constrained
S = 1.02	Δρ_max = 1.11 e Å⁻³
3880 reflections	Δρ_min = −0.70 e Å⁻³
229 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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Co(C₁₁H₁₇N₄O₂)₂(CH₄O)₂](ClO₄)₂
M_r	796.49
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.761 (3), 9.030 (3), 11.819 (4)
α, β, γ (°)	88.470 (8), 85.260 (11), 66.638 (7)
V (Å³)	855.4 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.21 × 0.10 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.862, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	7639, 3880, 2629
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.169, 1.02
No. of reflections	3880
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.11, −0.70

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2009).