Tris[2-(1H-imidazol-2-yl)imidazol-1-ido]cobalt(III)

Ma, Q.; Zhu, M.; Feng, S.; Lu, L.

doi:10.1107/S1600536810011785

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page m500

https://doi.org/10.1107/S1600536810011785

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Tris[2-(1H-imidazol-2-yl)imidazol-1-ido]cobalt(III)

Qi Ma,^a,^b Miaoli Zhu,^a Sisi Feng ^a and Liping Lu ^a ^*

^aInstitute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of the Education Ministry, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Shanxi Datong University, Datong, Shanxi 037009, People's Republic of China
^*Correspondence e-mail: luliping@sxu.edu.cn

(Received 25 March 2010; accepted 29 March 2010; online 10 April 2010)

In the title compound, [Co(C₆H₅N₄)₃], the Co^III atom adopts a distorted octahedral CoN₆ coordination geometry, arising from three N,N′-bidentate deprotonated 2,2′-biimidazole ligands. The dihedral angles between the five-membered rings of the ligands are 4.1 (2), 9.4 (2) and 10.5 (2)°. In the crystal, molecules are linked by N—H⋯N hydrogen bonds, generating a layered network lying in (11 $[\overline{1}]$ ).

Related literature

For related structures, see: Tadokoro & Nakasuji (2000 ); Ye et al. (2005 ); Zhang et al. (2008 ).

Experimental

Crystal data

[Co(C₆H₅N₄)₃]
M_r = 458.35
Monoclinic, P 2₁ /n
a = 12.299 (3) Å
b = 12.524 (3) Å
c = 12.932 (3) Å
β = 97.773 (4)°
V = 1973.6 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 293 K
0.5 × 0.4 × 0.3 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.654, T_max = 0.762
10212 measured reflections
3728 independent reflections
2358 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.138
S = 0.98
3728 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Co1—N4	1.917 (3)
Co1—N3	1.922 (3)
Co1—N6	1.926 (3)
Co1—N1	1.929 (3)
Co1—N5	1.941 (3)
Co1—N2	1.944 (3)

N4—Co1—N3	82.54 (12)
N6—Co1—N5	81.67 (13)
N1—Co1—N2	82.18 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H6⋯N12ⁱ	0.86	1.95	2.808 (4)	172
N7—H11⋯N8ⁱⁱ	0.86	1.99	2.814 (4)	159
N9—H19⋯N10ⁱⁱⁱ	0.86	1.95	2.796 (4)	169
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x, -y+1, -z+2; (iii) -x+1, -y+2, -z+2.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810011785/hb5377sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810011785/hb5377Isup2.hkl

checkCIF report

Comment top

The neutral molecule 2,2'-biimidazole (H₂biim) and its monoanionic derivative(Hbiim^-) is a particular organic target for construction of hybrid materials. Its molecular moieties possess a double property. Namely they can be coordinated to metal centres and can act as a donor in hydrogen bonding interactions (Tadokoro & Nakasuji, 2000). The crystal structure of (I) is reported here.

The X-ray crystallographic analysis shows that the molecule of the compound (I) consists of three Hbiim^- and one Co³⁺ (Fig. 1). The Co³⁺ ion adopted octahedron coordination geometry, and coordinated with three Hbiim^- anion. Average bond distance Co—N is 1.93 (3) Å, shorter than Co—N bond distance found in related structures, i.e. 2.116 (2)-2.118Å in [Co(H₂biim)₂(1,2-bdc)] (Ye et al., 2005), 2.1563 (18)Å , in diaquabis(2,2'-biimidazole)cobalt(II) dichloride (Zhang et al., 2008). In the crystalline state, the neighboring molecules are linked furtherly by N—H···N hydrogen bonding forming supermolecular structure(Fig. 2).

Related literature top

For related structures, see: Tadokoro & Nakasuji (2000); Ye et al. (2005); Zhang et al. (2008).

Experimental top

CoCl₂.6H₂O (0.1904 g, 0.8 mmol), biimidazole (0.107 g, 1 mmol), and water (10 ml) were added to an aqueous solution (5 ml) containing NaN₃ (0.028 g,0.4 mmol). The resulting mixture was further stirred for 15 min in air, and then transferred and sealed in a 20 ml Teflon-lined reactor, which was heated at 423 K for 4 days and then cooled to room temperature at a rate of 5 K h^-1. Red blocks of (I) were obtained and washed with water.

Structure description top

For related structures, see: Tadokoro & Nakasuji (2000); Ye et al. (2005); Zhang et al. (2008).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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. A view of the structure of (I) with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. hydrogen bond interaction in neighboring molecules.

Tris[2-(1H-imidazol-2-yl)imidazol-1-ido]cobalt(III) top

Crystal data top

[Co(C₆H₅N₄)₃]	F(000) = 936
M_r = 458.35	D_x = 1.543 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10212 reflections
a = 12.299 (3) Å	θ = 2.3–20.5°
b = 12.524 (3) Å	µ = 0.90 mm⁻¹
c = 12.932 (3) Å	T = 293 K
β = 97.773 (4)°	Block, red
V = 1973.6 (8) Å³	0.5 × 0.4 × 0.3 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3728 independent reflections
Radiation source: fine-focus sealed tube	2358 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ω scans	θ_max = 25.7°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→15
T_min = 0.654, T_max = 0.762	k = −15→13
10212 measured reflections	l = −15→13

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0798P)²] where P = (F_o² + 2F_c²)/3
3728 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Co(C₆H₅N₄)₃]	V = 1973.6 (8) Å³
M_r = 458.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.299 (3) Å	µ = 0.90 mm⁻¹
b = 12.524 (3) Å	T = 293 K
c = 12.932 (3) Å	0.5 × 0.4 × 0.3 mm
β = 97.773 (4)°

Data collection top

Bruker SMART CCD diffractometer	3728 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2358 reflections with I > 2σ(I)
T_min = 0.654, T_max = 0.762	R_int = 0.046
10212 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 0.98	Δρ_max = 0.48 e Å⁻³
3728 reflections	Δρ_min = −0.49 e Å⁻³
280 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.14643 (4)	0.83171 (4)	0.84581 (4)	0.03246 (19)
N1	0.1905 (2)	0.8669 (2)	0.7123 (2)	0.0325 (7)
N2	0.0080 (2)	0.8920 (2)	0.7814 (2)	0.0348 (7)
N3	0.2012 (2)	0.9650 (2)	0.9055 (2)	0.0324 (7)
N4	0.2936 (2)	0.7858 (2)	0.8922 (2)	0.0344 (7)
N5	0.1019 (2)	0.7861 (2)	0.9773 (2)	0.0348 (8)
N6	0.0917 (2)	0.6922 (2)	0.8032 (3)	0.0365 (8)
C5	0.2563 (3)	0.9108 (3)	0.5682 (3)	0.0400 (10)
H2	0.3051	0.9191	0.5197	0.048*
C6	0.2817 (3)	0.8656 (3)	0.6656 (3)	0.0396 (10)
H1	0.3498	0.8388	0.6939	0.048*
N12	0.1482 (2)	0.9419 (2)	0.5534 (2)	0.0360 (8)
C4	0.1135 (3)	0.9131 (3)	0.6429 (3)	0.0308 (8)
C3	0.0105 (3)	0.9241 (3)	0.6834 (3)	0.0343 (9)
N11	−0.0888 (2)	0.9582 (2)	0.6405 (3)	0.0433 (9)
H6	−0.1059	0.9829	0.5783	0.052*
C2	−0.1578 (3)	0.9462 (4)	0.7141 (4)	0.0516 (12)
H7	−0.2322	0.9627	0.7060	0.062*
C1	−0.0984 (3)	0.9061 (3)	0.8007 (3)	0.0435 (10)
H8	−0.1249	0.8905	0.8630	0.052*
C18	0.0637 (4)	0.6367 (3)	0.7131 (3)	0.0477 (11)
H9	0.0782	0.6578	0.6473	0.057*
C17	0.0115 (4)	0.5462 (3)	0.7345 (3)	0.0493 (11)
H10	−0.0153	0.4939	0.6866	0.059*
N7	0.0051 (3)	0.5451 (2)	0.8392 (3)	0.0397 (8)
H11	−0.0243	0.4963	0.8731	0.048*
C16	0.0534 (3)	0.6349 (3)	0.8788 (3)	0.0322 (9)
C15	0.0665 (3)	0.6837 (3)	0.9789 (3)	0.0306 (8)
N8	0.0546 (3)	0.6485 (2)	1.0734 (2)	0.0412 (8)
C14	0.0858 (3)	0.7350 (3)	1.1374 (3)	0.0477 (11)
H15	0.0868	0.7361	1.2094	0.057*
C13	0.1150 (3)	0.8185 (3)	1.0787 (3)	0.0392 (10)
H16	0.1393	0.8852	1.1036	0.047*
C12	0.3600 (3)	0.7001 (3)	0.8784 (3)	0.0429 (10)
H17	0.3368	0.6345	0.8496	0.051*
C11	0.4643 (3)	0.7274 (3)	0.9139 (3)	0.0469 (11)
H18	0.5256	0.6836	0.9151	0.056*
N9	0.4642 (3)	0.8312 (2)	0.9480 (3)	0.0413 (8)
H19	0.5204	0.8683	0.9734	0.050*
C10	0.3598 (3)	0.8634 (3)	0.9339 (3)	0.0331 (9)
C9	0.3067 (3)	0.9641 (3)	0.9483 (3)	0.0333 (9)
N10	0.3413 (2)	1.0555 (2)	0.9935 (3)	0.0368 (8)
C8	0.2507 (3)	1.1201 (3)	0.9770 (3)	0.0419 (10)
H23	0.2482	1.1907	0.9988	0.050*
C7	0.1643 (3)	1.0652 (3)	0.9236 (3)	0.0394 (9)
H24	0.0939	1.0913	0.9034	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0365 (3)	0.0314 (3)	0.0284 (3)	−0.0033 (2)	0.0010 (2)	0.0038 (2)
N1	0.0327 (16)	0.0320 (16)	0.0321 (19)	−0.0013 (13)	0.0023 (14)	0.0052 (14)
N2	0.0354 (17)	0.0352 (18)	0.033 (2)	−0.0026 (14)	0.0028 (14)	0.0041 (15)
N3	0.0359 (17)	0.0304 (17)	0.030 (2)	−0.0012 (13)	0.0013 (14)	0.0040 (13)
N4	0.0396 (17)	0.0262 (16)	0.036 (2)	−0.0012 (14)	−0.0009 (15)	0.0041 (14)
N5	0.0377 (17)	0.0316 (17)	0.035 (2)	−0.0041 (14)	0.0021 (15)	0.0008 (14)
N6	0.0437 (18)	0.0348 (17)	0.030 (2)	−0.0040 (14)	0.0017 (15)	0.0001 (14)
C5	0.040 (2)	0.046 (2)	0.035 (3)	−0.0064 (18)	0.0082 (19)	0.0010 (19)
C6	0.034 (2)	0.042 (2)	0.041 (3)	−0.0004 (17)	0.0028 (19)	0.0017 (19)
N12	0.0379 (18)	0.0370 (18)	0.032 (2)	−0.0054 (14)	0.0008 (15)	0.0026 (14)
C4	0.0361 (19)	0.0306 (19)	0.025 (2)	−0.0051 (16)	0.0013 (16)	0.0005 (16)
C3	0.038 (2)	0.033 (2)	0.031 (2)	−0.0034 (17)	0.0056 (18)	0.0003 (17)
N11	0.0374 (18)	0.055 (2)	0.036 (2)	0.0019 (15)	0.0008 (16)	0.0097 (16)
C2	0.034 (2)	0.071 (3)	0.051 (3)	0.004 (2)	0.009 (2)	0.010 (2)
C1	0.039 (2)	0.057 (3)	0.037 (3)	−0.0025 (19)	0.0129 (19)	0.006 (2)
C18	0.074 (3)	0.046 (2)	0.024 (2)	−0.006 (2)	0.010 (2)	−0.0032 (19)
C17	0.072 (3)	0.046 (3)	0.029 (3)	−0.013 (2)	0.003 (2)	−0.0085 (19)
N7	0.051 (2)	0.0336 (18)	0.034 (2)	−0.0088 (15)	0.0043 (16)	−0.0024 (15)
C16	0.040 (2)	0.033 (2)	0.024 (2)	−0.0040 (16)	0.0040 (17)	0.0020 (16)
C15	0.0329 (19)	0.030 (2)	0.028 (2)	−0.0031 (15)	0.0023 (16)	0.0038 (16)
N8	0.056 (2)	0.0400 (19)	0.027 (2)	−0.0081 (15)	0.0056 (17)	0.0011 (15)
C14	0.069 (3)	0.051 (3)	0.024 (2)	−0.007 (2)	0.010 (2)	−0.004 (2)
C13	0.051 (2)	0.037 (2)	0.029 (2)	−0.0044 (18)	0.0035 (19)	−0.0078 (18)
C12	0.056 (3)	0.030 (2)	0.041 (3)	0.0033 (18)	0.000 (2)	0.0027 (18)
C11	0.050 (2)	0.042 (3)	0.046 (3)	0.014 (2)	−0.003 (2)	0.006 (2)
N9	0.0407 (18)	0.0404 (19)	0.039 (2)	0.0016 (15)	−0.0083 (16)	−0.0009 (15)
C10	0.033 (2)	0.034 (2)	0.030 (2)	−0.0009 (16)	−0.0031 (17)	0.0073 (17)
C9	0.038 (2)	0.031 (2)	0.030 (2)	−0.0019 (16)	0.0032 (18)	0.0034 (16)
N10	0.0440 (18)	0.0334 (18)	0.034 (2)	−0.0023 (14)	0.0071 (15)	−0.0058 (14)
C8	0.053 (2)	0.033 (2)	0.043 (3)	−0.0008 (19)	0.016 (2)	−0.0025 (19)
C7	0.043 (2)	0.036 (2)	0.041 (3)	0.0060 (18)	0.0120 (19)	0.0044 (18)

Geometric parameters (Å, º) top

Co1—N4	1.917 (3)	C2—C1	1.348 (5)
Co1—N3	1.922 (3)	C2—H7	0.9300
Co1—N6	1.926 (3)	C1—H8	0.9300
Co1—N1	1.929 (3)	C18—C17	1.350 (5)
Co1—N5	1.941 (3)	C18—H9	0.9300
Co1—N2	1.944 (3)	C17—N7	1.367 (5)
N1—C6	1.344 (4)	C17—H10	0.9300
N1—C4	1.345 (4)	N7—C16	1.341 (4)
N2—C3	1.333 (5)	N7—H11	0.8600
N2—C1	1.376 (4)	C16—C15	1.420 (5)
N3—C9	1.340 (4)	C15—N8	1.326 (5)
N3—C7	1.365 (4)	N8—C14	1.386 (5)
N4—C10	1.335 (5)	C14—C13	1.369 (5)
N4—C12	1.374 (4)	C14—H15	0.9300
N5—C15	1.356 (4)	C13—H16	0.9300
N5—C13	1.361 (5)	C12—C11	1.347 (5)
N6—C16	1.349 (5)	C12—H17	0.9300
N6—C18	1.361 (5)	C11—N9	1.373 (5)
C5—N12	1.373 (4)	C11—H18	0.9300
C5—C6	1.378 (5)	N9—C10	1.334 (5)
C5—H2	0.9300	N9—H19	0.8600
C6—H1	0.9300	C10—C9	1.443 (5)
N12—C4	1.336 (5)	C9—N10	1.329 (4)
C4—C3	1.442 (5)	N10—C8	1.370 (5)
C3—N11	1.341 (5)	C8—C7	1.372 (5)
N11—C2	1.367 (5)	C8—H23	0.9300
N11—H6	0.8600	C7—H24	0.9300

N4—Co1—N3	82.54 (12)	C1—C2—H7	126.2
N4—Co1—N6	95.52 (13)	N11—C2—H7	126.2
N3—Co1—N6	173.01 (13)	C2—C1—N2	108.6 (4)
N4—Co1—N1	88.88 (12)	C2—C1—H8	125.7
N3—Co1—N1	92.05 (13)	N2—C1—H8	125.7
N6—Co1—N1	94.62 (13)	C17—C18—N6	109.0 (4)
N4—Co1—N5	90.23 (13)	C17—C18—H9	125.5
N3—Co1—N5	91.61 (13)	N6—C18—H9	125.5
N6—Co1—N5	81.67 (13)	C18—C17—N7	107.7 (4)
N1—Co1—N5	176.08 (12)	C18—C17—H10	126.2
N4—Co1—N2	170.39 (13)	N7—C17—H10	126.2
N3—Co1—N2	94.22 (12)	C16—N7—C17	106.8 (3)
N6—Co1—N2	88.73 (13)	C16—N7—H11	126.6
N1—Co1—N2	82.18 (12)	C17—N7—H11	126.6
N5—Co1—N2	98.93 (12)	N7—C16—N6	110.4 (3)
C6—N1—C4	105.1 (3)	N7—C16—C15	134.4 (3)
C6—N1—Co1	138.8 (3)	N6—C16—C15	115.1 (3)
C4—N1—Co1	116.0 (2)	N8—C15—N5	113.9 (3)
C3—N2—C1	106.1 (3)	N8—C15—C16	133.1 (3)
C3—N2—Co1	113.1 (2)	N5—C15—C16	113.0 (3)
C1—N2—Co1	140.5 (3)	C15—N8—C14	103.5 (3)
C9—N3—C7	105.2 (3)	C13—C14—N8	109.8 (4)
C9—N3—Co1	115.2 (2)	C13—C14—H15	125.1
C7—N3—Co1	139.5 (3)	N8—C14—H15	125.1
C10—N4—C12	106.3 (3)	N5—C13—C14	107.5 (3)
C10—N4—Co1	114.0 (2)	N5—C13—H16	126.2
C12—N4—Co1	138.2 (3)	C14—C13—H16	126.2
C15—N5—C13	105.3 (3)	C11—C12—N4	108.2 (3)
C15—N5—Co1	114.9 (3)	C11—C12—H17	125.9
C13—N5—Co1	138.2 (3)	N4—C12—H17	125.9
C16—N6—C18	106.1 (3)	C12—C11—N9	107.9 (3)
C16—N6—Co1	114.7 (3)	C12—C11—H18	126.1
C18—N6—Co1	138.3 (3)	N9—C11—H18	126.1
N12—C5—C6	109.9 (3)	C10—N9—C11	106.6 (3)
N12—C5—H2	125.1	C10—N9—H19	126.7
C6—C5—H2	125.1	C11—N9—H19	126.7
N1—C6—C5	107.8 (3)	N9—C10—N4	111.0 (3)
N1—C6—H1	126.1	N9—C10—C9	133.7 (3)
C5—C6—H1	126.1	N4—C10—C9	115.2 (3)
C4—N12—C5	102.7 (3)	N10—C9—N3	114.1 (3)
N12—C4—N1	114.6 (3)	N10—C9—C10	133.3 (3)
N12—C4—C3	133.6 (3)	N3—C9—C10	112.6 (3)
N1—C4—C3	111.8 (3)	C9—N10—C8	103.6 (3)
N2—C3—N11	110.7 (3)	N10—C8—C7	109.9 (3)
N2—C3—C4	116.8 (3)	N10—C8—H23	125.0
N11—C3—C4	132.5 (4)	C7—C8—H23	125.0
C3—N11—C2	107.0 (3)	N3—C7—C8	107.1 (3)
C3—N11—H6	126.5	N3—C7—H24	126.4
C2—N11—H6	126.5	C8—C7—H24	126.4
C1—C2—N11	107.6 (3)

N4—Co1—N1—C6	−1.6 (4)	C1—N2—C3—C4	−177.6 (3)
N3—Co1—N1—C6	80.9 (4)	Co1—N2—C3—C4	−2.2 (4)
N6—Co1—N1—C6	−97.0 (4)	N12—C4—C3—N2	−175.1 (4)
N2—Co1—N1—C6	174.9 (4)	N1—C4—C3—N2	2.5 (5)
N4—Co1—N1—C4	−176.0 (3)	N12—C4—C3—N11	7.4 (7)
N3—Co1—N1—C4	−93.5 (3)	N1—C4—C3—N11	−174.9 (4)
N6—Co1—N1—C4	88.5 (3)	N2—C3—N11—C2	−0.7 (4)
N2—Co1—N1—C4	0.4 (2)	C4—C3—N11—C2	176.9 (4)
N3—Co1—N2—C3	92.5 (3)	C3—N11—C2—C1	0.7 (5)
N6—Co1—N2—C3	−93.8 (3)	N11—C2—C1—N2	−0.4 (5)
N1—Co1—N2—C3	1.0 (2)	C3—N2—C1—C2	0.0 (5)
N5—Co1—N2—C3	−175.2 (2)	Co1—N2—C1—C2	−173.3 (3)
N3—Co1—N2—C1	−94.5 (4)	C16—N6—C18—C17	−1.3 (5)
N6—Co1—N2—C1	79.2 (4)	Co1—N6—C18—C17	−169.1 (3)
N1—Co1—N2—C1	174.0 (4)	N6—C18—C17—N7	0.8 (5)
N5—Co1—N2—C1	−2.2 (4)	C18—C17—N7—C16	0.1 (5)
N4—Co1—N3—C9	−0.3 (3)	C17—N7—C16—N6	−0.9 (4)
N1—Co1—N3—C9	−88.9 (3)	C17—N7—C16—C15	174.7 (4)
N5—Co1—N3—C9	89.8 (3)	C18—N6—C16—N7	1.3 (4)
N2—Co1—N3—C9	−171.2 (3)	Co1—N6—C16—N7	172.5 (2)
N4—Co1—N3—C7	−176.5 (4)	C18—N6—C16—C15	−175.2 (3)
N1—Co1—N3—C7	94.9 (4)	Co1—N6—C16—C15	−4.0 (4)
N5—Co1—N3—C7	−86.5 (4)	C13—N5—C15—N8	0.8 (4)
N2—Co1—N3—C7	12.6 (4)	Co1—N5—C15—N8	169.0 (2)
N3—Co1—N4—C10	−3.9 (3)	C13—N5—C15—C16	−177.1 (3)
N6—Co1—N4—C10	−177.1 (3)	Co1—N5—C15—C16	−8.9 (4)
N1—Co1—N4—C10	88.3 (3)	N7—C16—C15—N8	15.6 (7)
N5—Co1—N4—C10	−95.5 (3)	N6—C16—C15—N8	−169.0 (4)
N3—Co1—N4—C12	−167.7 (4)	N7—C16—C15—N5	−167.0 (4)
N6—Co1—N4—C12	19.0 (4)	N6—C16—C15—N5	8.5 (5)
N1—Co1—N4—C12	−75.5 (4)	N5—C15—N8—C14	−0.6 (4)
N5—Co1—N4—C12	100.7 (4)	C16—C15—N8—C14	176.8 (4)
N4—Co1—N5—C15	−90.1 (3)	C15—N8—C14—C13	0.1 (5)
N3—Co1—N5—C15	−172.6 (3)	C15—N5—C13—C14	−0.7 (4)
N6—Co1—N5—C15	5.5 (2)	Co1—N5—C13—C14	−164.5 (3)
N2—Co1—N5—C15	92.8 (3)	N8—C14—C13—N5	0.4 (5)
N4—Co1—N5—C13	72.7 (4)	C10—N4—C12—C11	1.1 (4)
N3—Co1—N5—C13	−9.9 (4)	Co1—N4—C12—C11	165.8 (3)
N6—Co1—N5—C13	168.2 (4)	N4—C12—C11—N9	−1.3 (5)
N2—Co1—N5—C13	−104.4 (4)	C12—C11—N9—C10	1.0 (4)
N4—Co1—N6—C16	88.8 (3)	C11—N9—C10—N4	−0.3 (4)
N1—Co1—N6—C16	178.1 (3)	C11—N9—C10—C9	−175.9 (4)
N5—Co1—N6—C16	−0.7 (3)	C12—N4—C10—N9	−0.5 (4)
N2—Co1—N6—C16	−99.9 (3)	Co1—N4—C10—N9	−169.3 (3)
N4—Co1—N6—C18	−104.1 (4)	C12—N4—C10—C9	176.0 (3)
N1—Co1—N6—C18	−14.8 (4)	Co1—N4—C10—C9	7.1 (4)
N5—Co1—N6—C18	166.5 (4)	C7—N3—C9—N10	0.6 (4)
N2—Co1—N6—C18	67.3 (4)	Co1—N3—C9—N10	−176.9 (2)
C4—N1—C6—C5	−0.4 (4)	C7—N3—C9—C10	−178.5 (3)
Co1—N1—C6—C5	−175.3 (3)	Co1—N3—C9—C10	4.0 (4)
N12—C5—C6—N1	0.5 (4)	N9—C10—C9—N10	−10.7 (8)
C6—C5—N12—C4	−0.3 (4)	N4—C10—C9—N10	173.8 (4)
C5—N12—C4—N1	0.1 (4)	N9—C10—C9—N3	168.2 (4)
C5—N12—C4—C3	177.6 (4)	N4—C10—C9—N3	−7.3 (5)
C6—N1—C4—N12	0.2 (4)	N3—C9—N10—C8	−0.8 (4)
Co1—N1—C4—N12	176.4 (2)	C10—C9—N10—C8	178.1 (4)
C6—N1—C4—C3	−177.9 (3)	C9—N10—C8—C7	0.7 (4)
Co1—N1—C4—C3	−1.7 (4)	C9—N3—C7—C8	−0.1 (4)
C1—N2—C3—N11	0.4 (4)	Co1—N3—C7—C8	176.4 (3)
Co1—N2—C3—N11	175.8 (2)	N10—C8—C7—N3	−0.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H6···N12ⁱ	0.86	1.95	2.808 (4)	172
N7—H11···N8ⁱⁱ	0.86	1.99	2.814 (4)	159
N9—H19···N10ⁱⁱⁱ	0.86	1.95	2.796 (4)	169

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+1, −z+2; (iii) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	[Co(C₆H₅N₄)₃]
M_r	458.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	12.299 (3), 12.524 (3), 12.932 (3)
β (°)	97.773 (4)
V (Å³)	1973.6 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.5 × 0.4 × 0.3

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.654, 0.762
No. of measured, independent and observed [I > 2σ(I)] reflections	10212, 3728, 2358
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.138, 0.98
No. of reflections	3728
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.49

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Co1—N4	1.917 (3)	Co1—N1	1.929 (3)
Co1—N3	1.922 (3)	Co1—N5	1.941 (3)
Co1—N6	1.926 (3)	Co1—N2	1.944 (3)

N4—Co1—N3	82.54 (12)	N1—Co1—N2	82.18 (12)
N6—Co1—N5	81.67 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H6···N12ⁱ	0.86	1.95	2.808 (4)	172
N7—H11···N8ⁱⁱ	0.86	1.99	2.814 (4)	159
N9—H19···N10ⁱⁱⁱ	0.86	1.95	2.796 (4)	169

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+1, −z+2; (iii) −x+1, −y+2, −z+2.

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 20471033), the Province Natural Science Foundation of Shanxi Province of China (grant No. 20051013) and the Overseas Returned Scholar Foundation of Shanxi Province of China in 2008, as well as Doctor Startup Foundation of Shanxi University of China.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tadokoro, M. & Nakasuji, K. (2000). Coord. Chem. Rev. 198, 205–218. Web of Science CrossRef CAS Google Scholar
Ye, B. H., Ding, B. B., Weng, Y. Q. & Chen, X. M. (2005). Cryst. Growth Des. 5, 801–806. Web of Science CSD CrossRef CAS Google Scholar
Zhang, L.-C., Zhu, Z.-M., You, W.-S., Chang, S. & Wang, E.-B. (2008). Acta Cryst. E64, m308. Web of Science CSD CrossRef IUCr Journals Google Scholar