Poly[[μ2-1,4-bis­(imidazol-1-ylmeth­yl)benzene]bis­(μ4-cyclo­hexane-1,4-dicarboxyl­ato)dicobalt(II)]

Yu, Q.-D.; Sun, D.-J.; Tiekink, E.R.T.

doi:10.1107/S160053680903428X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page m1165

doi:10.1107/S160053680903428X

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Poly[[μ₂-1,4-bis(imidazol-1-ylmethyl)benzene]bis(μ₄-cyclohexane-1,4-dicarboxylato)dicobalt(II)]

Qun-Di Yu,^a Da-Jun Sun ^b ^* and Edward R. T. Tiekink ^c

^aFood Science and Pharmacy College, Zhejiang Ocean University, Zhoushan 316000, People's Republic of China, ^bDepartment of Vascular Surgery, the China–Japan Union Hospital of Jilin University, Changchun, 130033, People's Republic of China, and ^cDepartment of Chemistry, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil
^*Correspondence e-mail: li_yp2002@yahoo.com.cn

(Received 13 August 2009; accepted 27 August 2009; online 5 September 2009)

In the title compound, [Co₂(C₈H₁₀O₄)₂(C₁₄H₁₄N₄)]_n, the two Co^II atoms are both five-coordinated by four carboxylate O atoms, derived from two different cyclohexane-1,4-dicarboxylate (chdc) ligands, and an N atom, derived from one end of a 1,4-bis(imidazol-1-ylmethyl)benzene molecule (1,4-bix), in a distorted square-pyramidal environment. Each end of the chdc ligand links pairs of Co^II atoms into a paddle-wheel assembly, i.e. Co₂(O₂CR′)₄; these are connected into rows because of the bridging nature of the chdc ligands, and the rows are further connected into a two-dimensional layer through the 1,4-bix ligands. The 1,4-bix ligand, which is disposed about a centre of inversion, is disorderd. Two positions were discerned for the –CH₂(C₆H₄)CH₂– residue, with the major component having a site-occupancy factor of 0.512 (9).

Related literature

For background to coordination polymers, see: Yang et al. (2008 ). For the isotypic Ni(II) structure, see: Li et al. (2009 ).

Experimental

Crystal data

[Co₂(C₈H₁₀O₄)₂(C₁₄H₁₄N₄)]
M_r = 696.48
Triclinic, $[P \overline 1]$
a = 8.5415 (6) Å
b = 8.8051 (5) Å
c = 10.8007 (5) Å
α = 93.824 (4)°
β = 100.940 (4)°
γ = 105.413 (5)°
V = 762.95 (8) Å³
Z = 1
Mo Kα radiation
μ = 1.14 mm⁻¹
T = 293 K
0.24 × 0.22 × 0.21 mm

Data collection

Bruker APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.756, T_max = 0.788
6296 measured reflections
2663 independent reflections
2212 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.150
S = 1.06
2663 reflections
206 parameters
30 restraints
H-atom parameters constrained
Δρ_max = 1.34 e Å⁻³
Δρ_min = −1.40 e Å⁻³

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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 global, I. DOI: 10.1107/S160053680903428X/bt5034sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680903428X/bt5034Isup2.hkl

checkCIF report

Comment top

So far, the rigid N-containing bridging ligand, such as 4,4'-bipyridine, has been widely used in the construction of metal-organic polymers, however, the flexible N-donor ligand, such as 1,4-bis(imidazol-1-ylmethyl)benzene (1,4-bix), has not been well studied (Yang et al., 2008). In this work, 1,4-bix assembles with cobalt cyclohexane-1,4-dicarboxylate (chdc) to give a two-dimensional polymer [Co₂(chdc)₂(1,4-bix)] (I).

The compound (I) is isostructural with reported Ni(II) compound (Li et al., 2009). The asymmetric unit of (I) comprises a Co atom, a chdc dianion, and half a 1, 4-bix molecule which is disposed about a centre of inversion (Fig. 1). Each Co^II atom is five-coordinated by four carboxylate O atoms, derived from two different chdc ligands, and an N atom, derived from one end of a 1,4-bix molecule, in distorted square pyramidal sphere. Each end of the chdc ligand links pairs of Co^II atoms into a paddle-wheel assembly, i.e. Co₂(O₂CR')₄. These are connected into rows because of the bridging nature of the chdc ligands, and rows are further connected into a two-dimensional layer through the 1,4-bix ligands. If the second Co atom in the paddle-wheel assembly is considered as occupying a coordination site, the Co···Co distance is 2.721 (6) Å, the coordination geometry would be distorted octahedral.

Related literature top

For background to coordination polymers, see: Yang et al. (2008). For the isomorphous Ni(II) structure, see: Li et al. (2009).

Experimental top

H₂chdc (0.5 mmol), 1,4-bix (0.5 mmol) and cobalt chloride hexahydrate (0.5 mmol) were placed in water (15 ml), and triethylamine was added until the pH value of the solution was 5.6. The solution was heated in a 23 ml Teflon-lined stainless-steel autoclave at 445 K for 3 days. The autoclave was cooled to room temperature over several hours. Purple crystals were isolated in about 52% yield.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 asymmetric unit in the polymeric structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Only one component of the disordered -CH₂(C₆H₄)CH₂- residue is shown for reasons of clarity.
	Fig. 2. View of the two-dimensional layer in (I). H atoms have been omitted for clarity.

Poly[[µ₂-1,4-bis(imidazol-1-ylmethyl)benzene]bis(µ₄-cyclohexane-1,4- dicarboxylato)dicobalt(II)] top

Crystal data top

[Co₂(C₈H₁₀O₄)₂(C₁₄H₁₄N₄)]	Z = 1
M_r = 696.48	F(000) = 360
Triclinic, P1	D_x = 1.516 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5415 (6) Å	Cell parameters from 2663 reflections
b = 8.8051 (5) Å	θ = 3.0–25.0°
c = 10.8007 (5) Å	µ = 1.14 mm⁻¹
α = 93.824 (4)°	T = 293 K
β = 100.940 (4)°	Block, purple
γ = 105.413 (5)°	0.24 × 0.22 × 0.21 mm
V = 762.95 (8) Å³

Data collection top

Bruker APEX diffractometer	2663 independent reflections
Radiation source: fine-focus sealed tube	2212 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 25.0°, θ_min = 4.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
T_min = 0.756, T_max = 0.788	k = −10→10
6296 measured reflections	l = −12→12

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0864P)² + 1.1188P] where P = (F_o² + 2F_c²)/3
2663 reflections	(Δ/σ)_max = 0.001
206 parameters	Δρ_max = 1.34 e Å⁻³
30 restraints	Δρ_min = −1.40 e Å⁻³

Crystal data top

[Co₂(C₈H₁₀O₄)₂(C₁₄H₁₄N₄)]	γ = 105.413 (5)°
M_r = 696.48	V = 762.95 (8) Å³
Triclinic, P1	Z = 1
a = 8.5415 (6) Å	Mo Kα radiation
b = 8.8051 (5) Å	µ = 1.14 mm⁻¹
c = 10.8007 (5) Å	T = 293 K
α = 93.824 (4)°	0.24 × 0.22 × 0.21 mm
β = 100.940 (4)°

Data collection top

Bruker APEX diffractometer	2663 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2212 reflections with I > 2σ(I)
T_min = 0.756, T_max = 0.788	R_int = 0.030
6296 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	30 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.06	Δρ_max = 1.34 e Å⁻³
2663 reflections	Δρ_min = −1.40 e Å⁻³
206 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
Co	1.02761 (7)	0.46504 (6)	0.62430 (5)	0.0287 (2)
O1	0.9612 (4)	0.6678 (4)	0.6589 (3)	0.0424 (8)
O2	0.9184 (4)	0.7201 (4)	0.4586 (3)	0.0416 (8)
O3	0.2725 (4)	0.5894 (4)	0.6746 (3)	0.0469 (8)
O4	0.2232 (4)	0.6331 (4)	0.4730 (3)	0.0471 (8)
N1	0.9757 (6)	0.3705 (5)	0.7847 (4)	0.0516 (8)
C1	0.9135 (5)	0.7472 (5)	0.5736 (4)	0.0320 (9)
C2	0.8510 (5)	0.8860 (5)	0.6110 (4)	0.0336 (10)
H2	0.9467	0.9810	0.6299	0.040*
C3	0.7803 (6)	0.8675 (6)	0.7305 (4)	0.0432 (11)
H3A	0.8603	0.8430	0.7969	0.052*
H3B	0.7635	0.9674	0.7597	0.052*
C4	0.6161 (5)	0.7374 (6)	0.7083 (4)	0.0370 (10)
H4A	0.6336	0.6357	0.6852	0.044*
H4B	0.5746	0.7320	0.7859	0.044*
C5	0.4889 (5)	0.7709 (5)	0.6026 (4)	0.0268 (8)
H5	0.4777	0.8752	0.6296	0.032*
C6	0.5562 (5)	0.7871 (5)	0.4806 (4)	0.0337 (10)
H6A	0.5710	0.6866	0.4507	0.040*
H6B	0.4761	0.8131	0.4152	0.040*
C7	0.7222 (6)	0.9163 (5)	0.5037 (5)	0.0382 (10)
H7A	0.7643	0.9202	0.4263	0.046*
H7B	0.7049	1.0185	0.5252	0.046*
C8	0.3170 (5)	0.6554 (5)	0.5811 (4)	0.0337 (10)
C9	1.0536 (7)	0.2819 (7)	0.8583 (6)	0.0653 (17)
H9	1.1446	0.2484	0.8461	0.078*
C10	0.9687 (11)	0.2518 (9)	0.9557 (6)	0.104 (3)
H10	0.9935	0.1930	1.0213	0.125*
C11	0.8543 (7)	0.3871 (6)	0.8375 (5)	0.0512 (13)
H11	0.7795	0.4418	0.8048	0.061*
N2	0.8493 (6)	0.3188 (5)	0.9406 (4)	0.0516 (8)
C12	0.7737 (19)	0.2877 (17)	1.0436 (13)	0.055 (3)	0.488 (9)
H12A	0.7196	0.3690	1.0584	0.066*	0.488 (9)
H12B	0.8591	0.2945	1.1188	0.066*	0.488 (9)
C13	0.6462 (19)	0.1259 (17)	1.0251 (14)	0.047 (3)	0.488 (9)
C14	0.653 (3)	0.034 (3)	1.120 (2)	0.064 (5)	0.488 (9)
H14	0.7379	0.0393	1.1893	0.077*	0.488 (9)
C15	0.516 (3)	0.076 (3)	0.9209 (18)	0.062 (4)	0.488 (9)
H15	0.5434	0.1302	0.8536	0.074*	0.488 (9)
C12'	0.6974 (18)	0.3329 (16)	1.0078 (12)	0.055 (3)	0.512 (9)
H12C	0.7410	0.3783	1.0960	0.066*	0.512 (9)
H12D	0.6391	0.4017	0.9648	0.066*	0.512 (9)
C13'	0.5796 (18)	0.1695 (16)	1.0001 (13)	0.047 (3)	0.512 (9)
C14'	0.598 (3)	0.076 (3)	1.093 (2)	0.064 (5)	0.512 (9)
H14'	0.6596	0.1367	1.1695	0.077*	0.512 (9)
C15'	0.456 (2)	0.110 (3)	0.8901 (17)	0.062 (4)	0.512 (9)
H15'	0.4158	0.1637	0.8254	0.074*	0.512 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co	0.0260 (3)	0.0332 (3)	0.0288 (3)	0.0076 (2)	0.0100 (2)	0.0080 (2)
O1	0.0416 (19)	0.0388 (17)	0.0489 (18)	0.0177 (15)	0.0047 (15)	0.0077 (15)
O2	0.045 (2)	0.0374 (17)	0.0500 (19)	0.0156 (15)	0.0224 (15)	0.0082 (14)
O3	0.0319 (18)	0.052 (2)	0.054 (2)	−0.0014 (15)	0.0210 (15)	0.0051 (16)
O4	0.0237 (17)	0.051 (2)	0.056 (2)	0.0035 (15)	−0.0051 (15)	0.0008 (16)
N1	0.056 (2)	0.0509 (18)	0.0342 (15)	−0.0122 (15)	0.0144 (14)	0.0067 (13)
C1	0.017 (2)	0.027 (2)	0.049 (3)	0.0003 (16)	0.0098 (18)	0.0050 (19)
C2	0.019 (2)	0.027 (2)	0.052 (3)	0.0010 (16)	0.0096 (18)	0.0020 (19)
C3	0.026 (2)	0.058 (3)	0.040 (2)	0.011 (2)	−0.0007 (19)	−0.010 (2)
C4	0.027 (2)	0.054 (3)	0.034 (2)	0.014 (2)	0.0094 (18)	0.015 (2)
C5	0.018 (2)	0.029 (2)	0.035 (2)	0.0073 (16)	0.0076 (16)	0.0060 (17)
C6	0.026 (2)	0.043 (2)	0.034 (2)	0.0116 (19)	0.0066 (17)	0.0079 (18)
C7	0.032 (2)	0.037 (2)	0.055 (3)	0.016 (2)	0.021 (2)	0.019 (2)
C8	0.026 (2)	0.031 (2)	0.047 (3)	0.0101 (18)	0.013 (2)	0.0025 (19)
C9	0.051 (3)	0.057 (3)	0.074 (4)	0.004 (3)	−0.012 (3)	0.035 (3)
C10	0.128 (7)	0.085 (5)	0.041 (3)	−0.046 (5)	−0.023 (4)	0.047 (3)
C11	0.052 (3)	0.051 (3)	0.048 (3)	−0.005 (2)	0.031 (2)	0.005 (2)
N2	0.056 (2)	0.0509 (18)	0.0342 (15)	−0.0122 (15)	0.0144 (14)	0.0067 (13)
C12	0.064 (9)	0.051 (6)	0.041 (6)	−0.012 (5)	0.034 (6)	−0.005 (4)
C13	0.056 (9)	0.040 (6)	0.044 (5)	−0.007 (4)	0.038 (6)	−0.006 (4)
C14	0.060 (13)	0.074 (12)	0.043 (8)	−0.014 (7)	0.021 (8)	−0.005 (7)
C15	0.071 (12)	0.067 (9)	0.040 (8)	−0.002 (7)	0.022 (7)	0.011 (5)
C12'	0.064 (9)	0.051 (6)	0.041 (6)	−0.012 (5)	0.034 (6)	−0.005 (4)
C13'	0.056 (9)	0.040 (6)	0.044 (5)	−0.007 (4)	0.038 (6)	−0.006 (4)
C14'	0.060 (13)	0.074 (12)	0.043 (8)	−0.014 (7)	0.021 (8)	−0.005 (7)
C15'	0.071 (12)	0.067 (9)	0.040 (8)	−0.002 (7)	0.022 (7)	0.011 (5)

Geometric parameters (Å, º) top

Co—O2ⁱ	2.008 (3)	C6—H6B	0.9700
Co—O3ⁱⁱ	2.035 (3)	C7—H7A	0.9700
Co—O1	2.044 (3)	C7—H7B	0.9700
Co—N1	2.044 (4)	C9—C10	1.388 (10)
Co—O4ⁱⁱⁱ	2.117 (3)	C9—H9	0.9300
Co—Coⁱ	2.7758 (10)	C10—N2	1.298 (11)
O1—C1	1.265 (5)	C10—H10	0.9300
O2—C1	1.260 (5)	C11—N2	1.303 (7)
O2—Coⁱ	2.008 (3)	C11—H11	0.9300
O3—C8	1.268 (6)	N2—C12	1.395 (13)
O3—Co^iv	2.035 (3)	N2—C12'	1.630 (14)
O4—C8	1.255 (5)	C12—C13	1.52 (2)
O4—Coⁱⁱⁱ	2.117 (3)	C12—H12A	0.9700
N1—C11	1.310 (7)	C12—H12B	0.9700
N1—C9	1.356 (7)	C13—C14	1.34 (3)
C1—C2	1.518 (6)	C13—C15	1.38 (2)
C2—C3	1.526 (6)	C14—C15^v	1.47 (4)
C2—C7	1.528 (6)	C14—H14	0.9300
C2—H2	0.9800	C15—C14^v	1.47 (4)
C3—C4	1.522 (6)	C15—H15	0.9300
C3—H3A	0.9700	C12'—C13'	1.507 (19)
C3—H3B	0.9700	C12'—H12C	0.9700
C4—C5	1.521 (5)	C12'—H12D	0.9700
C4—H4A	0.9700	C13'—C14'	1.35 (3)
C4—H4B	0.9700	C13'—C15'	1.40 (2)
C5—C8	1.513 (6)	C14'—C15'^v	1.62 (3)
C5—C6	1.535 (6)	C14'—H14'	0.9300
C5—H5	0.9800	C15'—C14'^v	1.62 (3)
C6—C7	1.529 (6)	C15'—H15'	0.9300
C6—H6A	0.9700

O2ⁱ—Co—O3ⁱⁱ	91.45 (14)	C2—C7—C6	111.7 (3)
O2ⁱ—Co—O1	164.36 (13)	C2—C7—H7A	109.3
O3ⁱⁱ—Co—O1	90.51 (14)	C6—C7—H7A	109.3
O2ⁱ—Co—N1	98.07 (16)	C2—C7—H7B	109.3
O3ⁱⁱ—Co—N1	104.53 (16)	C6—C7—H7B	109.3
O1—Co—N1	96.44 (16)	H7A—C7—H7B	107.9
O2ⁱ—Co—O4ⁱⁱⁱ	88.63 (14)	O4—C8—O3	123.1 (4)
O3ⁱⁱ—Co—O4ⁱⁱⁱ	164.38 (14)	O4—C8—C5	118.6 (4)
O1—Co—O4ⁱⁱⁱ	85.35 (13)	O3—C8—C5	118.3 (4)
N1—Co—O4ⁱⁱⁱ	90.91 (16)	N1—C9—C10	105.5 (7)
O2ⁱ—Co—Coⁱ	81.73 (9)	N1—C9—H9	127.3
O3ⁱⁱ—Co—Coⁱ	97.00 (10)	C10—C9—H9	127.3
O1—Co—Coⁱ	82.63 (9)	N2—C10—C9	109.2 (5)
N1—Co—Coⁱ	158.46 (13)	N2—C10—H10	125.4
O4ⁱⁱⁱ—Co—Coⁱ	67.55 (10)	C9—C10—H10	125.4
C1—O1—Co	124.3 (3)	N2—C11—N1	112.8 (6)
C1—O2—Coⁱ	127.3 (3)	N2—C11—H11	123.6
C8—O3—Co^iv	109.5 (3)	N1—C11—H11	123.6
C8—O4—Coⁱⁱⁱ	142.2 (3)	C10—N2—C11	106.6 (5)
C11—N1—C9	105.9 (5)	C10—N2—C12	105.7 (9)
C11—N1—Co	124.5 (4)	C11—N2—C12	147.6 (9)
C9—N1—Co	129.6 (4)	C10—N2—C12'	138.7 (7)
O2—C1—O1	123.6 (4)	C11—N2—C12'	114.6 (7)
O2—C1—C2	117.6 (4)	C12—N2—C12'	33.2 (7)
O1—C1—C2	118.8 (4)	N2—C12—C13	113.8 (10)
C1—C2—C3	112.7 (4)	N2—C12—H12A	108.8
C1—C2—C7	112.7 (4)	C13—C12—H12A	108.8
C3—C2—C7	109.5 (4)	N2—C12—H12B	108.8
C1—C2—H2	107.2	C13—C12—H12B	108.8
C3—C2—H2	107.2	H12A—C12—H12B	107.7
C7—C2—H2	107.2	C14—C13—C15	118.9 (18)
C4—C3—C2	112.5 (4)	C14—C13—C12	118.3 (16)
C4—C3—H3A	109.1	C15—C13—C12	122.6 (15)
C2—C3—H3A	109.1	C13—C14—C15^v	98.2 (16)
C4—C3—H3B	109.1	C13—C14—H14	130.9
C2—C3—H3B	109.1	C15^v—C14—H14	130.9
H3A—C3—H3B	107.8	C13—C15—C14^v	141.3 (19)
C5—C4—C3	110.3 (4)	C13—C15—H15	109.3
C5—C4—H4A	109.6	C14^v—C15—H15	109.3
C3—C4—H4A	109.6	C13'—C12'—N2	108.8 (9)
C5—C4—H4B	109.6	C13'—C12'—H12C	109.9
C3—C4—H4B	109.6	N2—C12'—H12C	109.9
H4A—C4—H4B	108.1	C13'—C12'—H12D	109.9
C8—C5—C4	114.2 (3)	N2—C12'—H12D	109.9
C8—C5—C6	112.8 (3)	H12C—C12'—H12D	108.3
C4—C5—C6	110.2 (3)	C14'—C13'—C15'	119.8 (17)
C8—C5—H5	106.3	C14'—C13'—C12'	121.5 (15)
C4—C5—H5	106.3	C15'—C13'—C12'	118.6 (13)
C6—C5—H5	106.3	C13'—C14'—C15'^v	138.1 (19)
C7—C6—C5	111.1 (3)	C13'—C14'—H14'	111.0
C7—C6—H6A	109.4	C15'^v—C14'—H14'	111.0
C5—C6—H6A	109.4	C13'—C15'—C14'^v	100.5 (13)
C7—C6—H6B	109.4	C13'—C15'—H15'	129.7
C5—C6—H6B	109.4	C14'^v—C15'—H15'	129.7
H6A—C6—H6B	108.0

O2ⁱ—Co—O1—C1	3.5 (7)	Co^iv—O3—C8—O4	−5.3 (5)
O3ⁱⁱ—Co—O1—C1	100.7 (3)	Co^iv—O3—C8—C5	172.4 (3)
N1—Co—O1—C1	−154.6 (3)	C4—C5—C8—O4	−153.7 (4)
O4ⁱⁱⁱ—Co—O1—C1	−64.2 (3)	C6—C5—C8—O4	−26.8 (5)
Coⁱ—Co—O1—C1	3.7 (3)	C4—C5—C8—O3	28.5 (5)
O2ⁱ—Co—N1—C11	−139.8 (4)	C6—C5—C8—O3	155.4 (4)
O3ⁱⁱ—Co—N1—C11	126.6 (4)	C11—N1—C9—C10	−0.6 (6)
O1—Co—N1—C11	34.4 (4)	Co—N1—C9—C10	179.1 (4)
O4ⁱⁱⁱ—Co—N1—C11	−51.1 (4)	N1—C9—C10—N2	−0.2 (7)
Coⁱ—Co—N1—C11	−51.9 (6)	C9—N1—C11—N2	1.2 (6)
O2ⁱ—Co—N1—C9	40.6 (5)	Co—N1—C11—N2	−178.5 (3)
O3ⁱⁱ—Co—N1—C9	−53.1 (5)	C9—C10—N2—C11	0.9 (7)
O1—Co—N1—C9	−145.3 (5)	C9—C10—N2—C12	−178.2 (7)
O4ⁱⁱⁱ—Co—N1—C9	129.3 (5)	C9—C10—N2—C12'	177.2 (8)
Coⁱ—Co—N1—C9	128.5 (5)	N1—C11—N2—C10	−1.3 (6)
Coⁱ—O2—C1—O1	8.4 (6)	N1—C11—N2—C12	177.0 (12)
Coⁱ—O2—C1—C2	−173.4 (3)	N1—C11—N2—C12'	−178.7 (6)
Co—O1—C1—O2	−8.0 (6)	C10—N2—C12—C13	−83.2 (12)
Co—O1—C1—C2	173.8 (3)	C11—N2—C12—C13	98.5 (15)
O2—C1—C2—C3	155.3 (4)	C12'—N2—C12—C13	91.3 (19)
O1—C1—C2—C3	−26.4 (5)	N2—C12—C13—C14	132.3 (16)
O2—C1—C2—C7	30.8 (5)	N2—C12—C13—C15	−54 (2)
O1—C1—C2—C7	−150.9 (4)	C15—C13—C14—C15^v	−12 (3)
C1—C2—C3—C4	−70.3 (5)	C12—C13—C14—C15^v	162.6 (15)
C7—C2—C3—C4	56.0 (5)	C14—C13—C15—C14^v	18 (4)
C2—C3—C4—C5	−57.7 (5)	C12—C13—C15—C14^v	−155 (3)
C3—C4—C5—C8	−175.0 (3)	C10—N2—C12'—C13'	−62.0 (14)
C3—C4—C5—C6	56.8 (5)	C11—N2—C12'—C13'	114.1 (10)
C8—C5—C6—C7	174.5 (3)	C12—N2—C12'—C13'	−70.1 (16)
C4—C5—C6—C7	−56.6 (5)	N2—C12'—C13'—C14'	90.6 (17)
C1—C2—C7—C6	71.5 (5)	N2—C12'—C13'—C15'	−85.0 (15)
C3—C2—C7—C6	−54.8 (5)	C15'—C13'—C14'—C15'^v	18 (4)
C5—C6—C7—C2	56.1 (5)	C12'—C13'—C14'—C15'^v	−158 (2)
Coⁱⁱⁱ—O4—C8—O3	12.1 (8)	C14'—C13'—C15'—C14'^v	−12 (3)
Coⁱⁱⁱ—O4—C8—C5	−165.6 (3)	C12'—C13'—C15'—C14'^v	163.8 (13)

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

Experimental details

Crystal data
Chemical formula	[Co₂(C₈H₁₀O₄)₂(C₁₄H₁₄N₄)]
M_r	696.48
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.5415 (6), 8.8051 (5), 10.8007 (5)
α, β, γ (°)	93.824 (4), 100.940 (4), 105.413 (5)
V (Å³)	762.95 (8)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.14
Crystal size (mm)	0.24 × 0.22 × 0.21

Data collection
Diffractometer	Bruker APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.756, 0.788
No. of measured, independent and observed [I > 2σ(I)] reflections	6296, 2663, 2212
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.150, 1.06
No. of reflections	2663
No. of parameters	206
No. of restraints	30
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.34, −1.40

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We thank Zhejiang Ocean University and the China–Japan Union Hospital of Jilin University for support.

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, B.-B., Fang, G.-X., Ji, X.-N., Xiao, B. & Tiekink, E. R. T. (2009). Acta Cryst. E65, m1012. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, J., Ma, J.-F., Batten, S. R. & Su, Z.-M. (2008). Chem. Commun. pp. 2233–2235. Web of Science CSD CrossRef Google Scholar

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