Di-μ2-acetato-diacetato-bis­{μ2-3,3′,5,5′-tetra­meth­oxy-2,2-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato}tricobalt(II,III) dichloro­methane disolvate

Assey, G.E.; Butcher, R.J.; Gultneh, Y.

doi:10.1107/S1600536811003783

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages m303-m304

doi:10.1107/S1600536811003783

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Di-μ₂-acetato-diacetato-bis{μ₂-3,3′,5,5′-tetramethoxy-2,2-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}tricobalt(II,III) dichloromethane disolvate

Gervas E. Assey,^a Ray J. Butcher ^a ^* and Yilma Gultneh ^a

^aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: rbutcher99@yahoo.com

(Received 11 January 2011; accepted 29 January 2011; online 5 February 2011)

The trinuclear title compound, [Co₃(CH₃COO)₄(C₂₀H₂₂N₂O₆)₂]·2CH₂Cl₂, contains mixed-valence cobalt ions in the following order Co^III–Co^II–Co^III where all the three cobalt ions are hexacoordinated. The central cobalt ion is situated on an inversion centre and is in an all-oxygen environment, coordinated by four phenolate O atoms and two O atoms from bridging acetate groups, while the terminal cobalt ion is hexacoordinated by two phenolate O atoms, two acetate O atoms and two imine N atoms. This complex contains a high-spin central Co^II and two terminal low-spin Co^III i.e. Co^III(S = 0)–Co^II(S = 3/2)-Co^III(S = 0). There are weak intermolecular C—H⋯O interactions involving the methoxy groups, as well as intermolecular C—H⋯O interactions involving the acetate anions. In addition, the dichoromethane solvate molecules are held in place by weak C—H⋯Cl interactions.

Related literature

For background to to the use of transition metal complexes with Schiff bases as potential enzyme inhibitors, see: You et al. (2008 ); Shi et al. (2007 ). For the use of transition metal complexes for the development of catalysis, magnetism and molecular architectures, see: Yu et al. (2007 ); You & Zhu (2004 ); You & Zhou (2007 ). For the use of transition metal complexes for optoelectronic and also for photo- and electroluminescence applications, see: Yu et al. (2008 ). For the potential use of transition metal complexes in the modeling of multisite metalloproteins and in nano-science, see: Chattopadhyay et al. (2006 ). For the importance of tri-nuclear cobalt Schiff base complexes as catalysts for organic molecules and as antiviral agents due to their ability to interact with proteins and nucleic acids, see: Chattopadhyay et al. (2006, 2008 ); Babushkin & Talsi (1998). For background to metallosalen complexes, see: Dong et al. (2008 ). For the magnetic properties of quadridentate metal complexes of Schiff bases, see: He et al. (2006 ); Gerli et al. (1991 ). For the antimicrobial activity of Schiff base ligands and their complexes, see: You et al. (2004 ).

Experimental

Crystal data

[Co₃(C₂H₃O₂)₄(C₂₀H₂₂N₂O₆)₂]·2CH₂Cl₂
M_r = 1355.61
Monoclinic, P 2₁ /n
a = 13.9235 (9) Å
b = 13.4407 (8) Å
c = 16.0019 (11) Å
β = 112.724 (8)°
V = 2762.2 (3) Å³
Z = 2
Cu Kα radiation
μ = 9.45 mm⁻¹
T = 110 K
0.42 × 0.25 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby detector
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.320, T_max = 1.000
10708 measured reflections
5306 independent reflections
3777 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.083
wR(F²) = 0.251
S = 1.03
5306 reflections
373 parameters
H-atom parameters constrained
Δρ_max = 1.11 e Å⁻³
Δρ_min = −1.66 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C—H0A⋯O22A	0.99	2.33	3.269 (13)	158
C4—H4A⋯O6ⁱ	0.98	2.35	3.326 (8)	175
C7—H7A⋯O6ⁱⁱ	0.98	2.51	3.421 (9)	156
C11—H11A⋯O3ⁱⁱ	0.99	2.62	3.602 (8)	174
C11—H11B⋯Cl1ⁱⁱⁱ	0.99	2.73	3.664 (8)	158
C15—H15A⋯O4^iv	0.98	2.64	3.568 (10)	158
C12A—H12B⋯Cl1ⁱⁱ	0.98	2.91	3.354 (8)	108
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO); 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/S1600536811003783/jj2072sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003783/jj2072Isup2.hkl

checkCIF report

Comment top

A number of transition metal complexes with Schiff base ligands have been studied as potential inhibitors for the xanthine oxidase (XO) enzyme (You et al., 2008) and also for the jack bean urease enzyme (jbU) (Shi et al., 2007). The enzyme XO catalyzes the hydroxylation of hypoxanthine and xanthine to yield uric acid and superoxide anions. Other areas where complexes of transition metals have played roles are in the development of catalysis, magnetism and molecular architecture (Yu et al., 2007, You & Zhu, 2004, You & Zhou, 2007). Complexes of transition metals with Schiff base ligands have also been shown to be useful materials for optoelectronics and also for photo and electro-luminance applications (Yu et al., 2008). Studies for antimicrobial activities of Schiff base ligands as well as those of their corresponding complexes have been investigated (You et al., 2004) where it was shown that Schiff base ligands as well as their complexes exhibited good antibacterial properties. Metallosalen complexes are of great importance due to their use in various catalytic chemical transformations that includes, epoxidation of olefins, symmetric ring opening, azirdination of olefins, olefine cyclopropanation and formation of linear and cyclic hydrocarbonation (Dong et al., 2008).

The importance of tri-nuclear cobalt Schiff base complexes ranges from, catalysts for oxidation of organic molecules, antiviral agents due to their ability to interact with proteins and nucleic acids and they have also used to mimic the biological co-factor such as cobalamin (Chattopadhyay et al., 2008, Babushkin & Talsi, 1998). The quadridentate metal complexes of Schiff bases have been studied extensively as B12 models, their magnetic interaction between bridged paramagnetic metal ions and their applications (Gerli et al., 1991). Magnetic susceptibilities data for the trinuclear mixed valence compound [Co^II(OAc)₂(hapt)₂Co₂(III)(py)₂](ClO₄)₂ [where (hapt) is bis-(2-hydroxyacetophenone) trimethylenediimine] were measured in the temperature range of 300–2 K and it was found that µ_eff values are almost constant ranging from 4.37 to 5.00 BM (He et al., 2006). The values obtained suggested that the oxidation states are Co^III(S = 0)-Co^II(S = 3/2)-Co^III(S = 0). Cyclic tri-nuclear cobalt complexes have also shown some catalytic activities in epoxidation of olefins, autoxidation of hydrocarbons, utility in modeling multinuclear active sites of metalloproteins and their potential use in nanoscience (Chattopadhyay et al., 2006).

The title compound C₅₀H₆₀Cl₄Co₃N₄O₂₀ is a trinuclear cobalt Schiff base complex containing a central high spin Co^II and two terminal low spin Co^III centers. The environment around Co(1) is hexacoordinated with two imine nitrogen atoms, N(1) and N(2), two phenolate oxygen atoms, O(1) and O(2), and two oxygen atoms, O(11 A) and O(21 A), from two acetate groups. The central Co(2) ion is coordinated by four phenolate oxygen atoms and two acetate oxygen atoms O(12 A), O(2)#2, O(2), O(1), O(1), O(1)#1 and O(12)#1. The bond distances of the coordination atoms around Co(1) are Co(1)—N(2) = 1.861 (5) Å, Co(1)—N(1) = 1.871 (5) Å, Co(1)—O(2) = 1.887 (4) Å, Co(1)—O(1) = 1.89 (4) Å, Co(1)—O(21 A) = 1.891 (4) Å, Co(1)—O(11 A) = 1.929 (4) Å and the bond lengths between Co(2) and its coordinating atoms are Co(2)—O(12 A)#1 = 2.043 (4) Å, Co(2)—O(12 A) = 2.043 (4) Å, Co(2)—O(2)#1 = 2.117 (4) Å, Co(A)—O(2) = 2.117 (4) Å, Co(2)—O(1) = 2.160 (4) Å, Co(2)—O(1)#1 = 2.160 (4) Å. The coordination around the central metal ion displays a slight distortion from octahedral geometry as shown by the cis angles are mostly close to 90°. The main deviations are caused by the small bite of the salen O donors [72.15 (15)°]. The basal planes of the complex are formed by the two bridging O atoms and two N atoms of the Schiff base ligand. The O atoms of the acetate group occupy apical positions.

There are weak intermolecular C—H···O interactions involving the methoxy groups and acetate anions. In addition the dichoromethane solvate molecules are held in place by weak C—H···Cl interactions.

Related literature top

For background to to the use of transition metal complexes with Schiff bases as potential enzyme inhibitors, see: You et al. (2008); Shi et al. (2007). For the use of transition metal complexes for the development of catalysis, magnetism and molecular architectures, see: Yu et al. (2007); You & Zhu (2004); You & Zhou (2007). For the use of transition metal complexes for optoelectronical and also for photo and electroluminance applications, see: Yu et al. (2008). For the potential use of transition metal complexes in the modeling of multisite metalloproteins and in nano-science, see: Chattopadhyay et al. (2006). For the importance of tri-nuclear cobalt Schiff base complexes as catalysts for organic molecules and as antiviral agents due to their ability to interact with proteins and nucleic acids, see: Chattopadhyay et al. (2006, 2008); Babushkin & Talsi (1998). For background to metallosalen complexes, see: Dong et al. (2008). For the magnetic properties of quadridentate metal complexes of Schiff bases, see: He et al. (2006); Gerli et al. (1991). For the antimicrobial activity of Schiff base ligands and their complexes, see: You et al. (2004). AUTHOR: please ensure all papers are cited in the Rel. lit

Experimental top

The synthesis of the ligand ethylene-bis(2,4-dimethoxy-salicylaldimine) was achieved by adding a solution of (2 g, 33.3 mmol) ethylenediamine in 25 ml s of methanol to the solution of (12.13 g, 66.6 mmol) 2,4-dimethoxysalicylaldehyde in 40 ml s of methanol. The mixture was refluxed overnight while stirring. The reaction mixture was then evaporated under reduced pressure to afford yellow solids.

The synthesis of the complex C₅₀H₆₀Cl₄Co₃N₄O₂₀ was accomplished by adding a solution of (0.38 g, 1 mmol) of ethylene-bis(2,4-dimethoxy-salicylaldimine) in 20 ml dichloromethane to a solution of Co(CH₃COO)₂.H₂O in 5 ml me thanol. The mixture was stirred for 3 h, filtered and layered with di-ethyl ether for crystallization. Crystals suitable for X-ray diffraction were obtained.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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. Diagram of trinuclear C₄₈H₅₆Co₃N₄O₂₀ unit showing atom labeling. Thermal ellipsoids are at the 30% probability level.
	Fig. 2. The molecular packing for C₄₈H₅₆Co₃N₄O₂₀^.2(CH₂Cl₂) viewed down the b axis. C—H···Cl and C—H···O interactions bonds are shown by dashed lines.

Di-µ₂-acetato-diacetato-bis{µ₂-3,3',5,5'-tetramethoxy-2,2-[ethane-1,2- diylbis(nitrilomethylidyne)]diphenolato}tricobalt(II,III) dichloromethane disolvate top

Crystal data top

[Co₃(C₂H₃O₂)₄(C₂₀H₂₂N₂O₆)₂]·2CH₂Cl₂	F(000) = 1394
M_r = 1355.61	D_x = 1.630 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 4463 reflections
a = 13.9235 (9) Å	θ = 4.4–73.9°
b = 13.4407 (8) Å	µ = 9.45 mm⁻¹
c = 16.0019 (11) Å	T = 110 K
β = 112.724 (8)°	Thick needle, red-brown
V = 2762.2 (3) Å³	0.42 × 0.25 × 0.18 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	5306 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3777 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 10.5081 pixels mm^-1	θ_max = 74.2°, θ_min = 4.5°
ω scans	h = −17→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −16→13
T_min = 0.320, T_max = 1.000	l = −19→18
10708 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)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.251	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.1718P)² + 2.5393P] where P = (F_o² + 2F_c²)/3
5306 reflections	(Δ/σ)_max < 0.001
373 parameters	Δρ_max = 1.11 e Å⁻³
0 restraints	Δρ_min = −1.66 e Å⁻³

Crystal data top

[Co₃(C₂H₃O₂)₄(C₂₀H₂₂N₂O₆)₂]·2CH₂Cl₂	V = 2762.2 (3) Å³
M_r = 1355.61	Z = 2
Monoclinic, P2₁/n	Cu Kα radiation
a = 13.9235 (9) Å	µ = 9.45 mm⁻¹
b = 13.4407 (8) Å	T = 110 K
c = 16.0019 (11) Å	0.42 × 0.25 × 0.18 mm
β = 112.724 (8)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	5306 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	3777 reflections with I > 2σ(I)
T_min = 0.320, T_max = 1.000	R_int = 0.043
10708 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.083	0 restraints
wR(F²) = 0.251	H-atom parameters constrained
S = 1.03	Δρ_max = 1.11 e Å⁻³
5306 reflections	Δρ_min = −1.66 e Å⁻³
373 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	0.31088 (7)	0.37441 (7)	0.38337 (6)	0.0133 (3)
Co2	0.5000	0.5000	0.5000	0.0138 (3)
Cl1	−0.1730 (2)	0.4911 (2)	0.0248 (2)	0.0736 (8)
Cl2	−0.2861 (3)	0.3805 (3)	0.1142 (2)	0.0826 (10)
O1	0.4170 (3)	0.4463 (3)	0.3637 (3)	0.0142 (8)
O2	0.3510 (3)	0.4519 (3)	0.4897 (3)	0.0176 (9)
O3	0.5670 (4)	0.6103 (3)	0.1809 (3)	0.0229 (10)
O4	0.3576 (4)	0.3258 (4)	0.0695 (3)	0.0239 (10)
O5	0.0593 (4)	0.3797 (4)	0.5633 (3)	0.0276 (11)
O6	0.2587 (4)	0.6707 (4)	0.6799 (3)	0.0279 (11)
O11A	0.4076 (3)	0.2697 (3)	0.4437 (3)	0.0178 (9)
O12A	0.5482 (3)	0.3568 (3)	0.5344 (3)	0.0182 (9)
O21A	0.2186 (3)	0.4771 (3)	0.3178 (3)	0.0213 (10)
O22A	0.0637 (4)	0.3991 (4)	0.2533 (3)	0.0296 (11)
N1	0.2737 (4)	0.2957 (4)	0.2792 (3)	0.0154 (10)
N2	0.2130 (4)	0.3016 (4)	0.4107 (3)	0.0179 (11)
C	−0.1698 (10)	0.3882 (8)	0.0942 (7)	0.062 (3)
H0A	−0.1096	0.3946	0.1527	0.075*
H0B	−0.1608	0.3263	0.0644	0.075*
C1	0.4274 (4)	0.4539 (5)	0.2860 (4)	0.0146 (12)
C2	0.4903 (4)	0.5312 (5)	0.2754 (4)	0.0129 (11)
H2A	0.5195	0.5790	0.3222	0.015*
C3	0.5093 (5)	0.5373 (5)	0.1979 (4)	0.0190 (13)
C4	0.6125 (5)	0.6836 (5)	0.2508 (4)	0.0265 (15)
H4A	0.6550	0.7298	0.2323	0.040*
H4B	0.6563	0.6503	0.3072	0.040*
H4C	0.5570	0.7205	0.2607	0.040*
C5	0.4666 (5)	0.4690 (5)	0.1259 (4)	0.0188 (13)
H5A	0.4817	0.4740	0.0731	0.023*
C6	0.4019 (5)	0.3940 (5)	0.1342 (4)	0.0170 (12)
C7	0.3851 (7)	0.3271 (6)	−0.0085 (5)	0.0353 (18)
H7A	0.3580	0.2671	−0.0448	0.053*
H7B	0.4611	0.3288	0.0114	0.053*
H7C	0.3550	0.3861	−0.0452	0.053*
C8	0.3786 (5)	0.3854 (5)	0.2132 (4)	0.0179 (12)
C9	0.3083 (4)	0.3071 (5)	0.2162 (4)	0.0150 (12)
H9A	0.2861	0.2607	0.1678	0.018*
C10	0.1969 (5)	0.2181 (5)	0.2716 (4)	0.0210 (13)
H10A	0.2179	0.1549	0.2518	0.025*
H10B	0.1280	0.2376	0.2261	0.025*
C11	0.1902 (6)	0.2044 (5)	0.3629 (5)	0.0267 (15)
H11A	0.1197	0.1814	0.3551	0.032*
H11B	0.2413	0.1538	0.3987	0.032*
C12	0.1734 (4)	0.3272 (5)	0.4676 (4)	0.0176 (12)
H12A	0.1235	0.2839	0.4752	0.021*
C13	0.1990 (5)	0.4164 (5)	0.5206 (4)	0.0181 (13)
C14	0.1394 (5)	0.4440 (5)	0.5709 (4)	0.0238 (14)
C15	−0.0028 (6)	0.4037 (6)	0.6139 (5)	0.0316 (17)
H15A	−0.0562	0.3525	0.6038	0.047*
H15B	−0.0363	0.4684	0.5941	0.047*
H15C	0.0417	0.4067	0.6786	0.047*
C16	0.1603 (5)	0.5288 (5)	0.6242 (5)	0.0231 (14)
H16A	0.1192	0.5456	0.6577	0.028*
C17	0.2433 (5)	0.5885 (5)	0.6274 (4)	0.0223 (14)
C18	0.3486 (6)	0.7310 (6)	0.6947 (6)	0.041 (2)
H18A	0.3498	0.7866	0.7347	0.061*
H18B	0.3458	0.7570	0.6366	0.061*
H18C	0.4116	0.6907	0.7229	0.061*
C19	0.3059 (5)	0.5648 (5)	0.5799 (4)	0.0185 (13)
H19A	0.3616	0.6072	0.5825	0.022*
C20	0.2851 (4)	0.4775 (5)	0.5283 (4)	0.0178 (13)
C11A	0.5005 (5)	0.2775 (5)	0.5022 (4)	0.0175 (12)
C12A	0.5555 (5)	0.1810 (5)	0.5336 (5)	0.0272 (15)
H12B	0.5189	0.1282	0.4910	0.041*
H12C	0.5569	0.1651	0.5938	0.041*
H12D	0.6270	0.1863	0.5367	0.041*
C21A	0.1218 (5)	0.4706 (5)	0.2639 (4)	0.0210 (13)
C22A	0.0821 (6)	0.5634 (6)	0.2093 (5)	0.0308 (16)
H22A	0.0067	0.5580	0.1758	0.046*
H22B	0.1163	0.5717	0.1665	0.046*
H22C	0.0974	0.6210	0.2500	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0088 (5)	0.0168 (5)	0.0142 (5)	−0.0035 (4)	0.0043 (3)	−0.0026 (4)
Co2	0.0088 (6)	0.0186 (7)	0.0142 (6)	−0.0039 (5)	0.0046 (5)	−0.0031 (5)
Cl1	0.0671 (18)	0.0709 (19)	0.0748 (18)	−0.0053 (15)	0.0184 (15)	0.0120 (15)
Cl2	0.087 (2)	0.093 (2)	0.075 (2)	−0.0023 (19)	0.0400 (18)	0.0040 (18)
O1	0.0090 (19)	0.020 (2)	0.0145 (19)	−0.0039 (17)	0.0058 (15)	−0.0011 (17)
O2	0.0118 (19)	0.024 (2)	0.019 (2)	−0.0044 (18)	0.0085 (16)	−0.0089 (18)
O3	0.023 (2)	0.022 (2)	0.027 (2)	−0.0050 (19)	0.0145 (19)	0.001 (2)
O4	0.025 (2)	0.033 (3)	0.014 (2)	−0.005 (2)	0.0088 (18)	−0.004 (2)
O5	0.017 (2)	0.035 (3)	0.037 (3)	−0.004 (2)	0.017 (2)	−0.005 (2)
O6	0.023 (2)	0.031 (3)	0.034 (3)	0.004 (2)	0.016 (2)	−0.010 (2)
O11A	0.013 (2)	0.019 (2)	0.018 (2)	−0.0029 (17)	0.0019 (16)	−0.0023 (17)
O12A	0.010 (2)	0.022 (2)	0.019 (2)	−0.0030 (17)	0.0019 (16)	−0.0040 (18)
O21A	0.014 (2)	0.023 (2)	0.024 (2)	0.0015 (18)	0.0034 (17)	−0.0020 (19)
O22A	0.023 (2)	0.024 (3)	0.034 (3)	−0.006 (2)	0.002 (2)	0.001 (2)
N1	0.011 (2)	0.017 (2)	0.016 (2)	−0.001 (2)	0.0028 (18)	−0.004 (2)
N2	0.012 (2)	0.020 (3)	0.021 (2)	−0.007 (2)	0.005 (2)	−0.001 (2)
C	0.084 (8)	0.044 (5)	0.052 (6)	−0.003 (6)	0.019 (6)	0.009 (5)
C1	0.007 (2)	0.017 (3)	0.016 (3)	0.003 (2)	0.001 (2)	0.000 (2)
C2	0.006 (2)	0.018 (3)	0.014 (3)	0.002 (2)	0.003 (2)	0.001 (2)
C3	0.011 (3)	0.019 (3)	0.024 (3)	0.007 (2)	0.003 (2)	0.005 (3)
C4	0.025 (3)	0.033 (4)	0.023 (3)	−0.015 (3)	0.012 (3)	−0.002 (3)
C5	0.024 (3)	0.024 (3)	0.014 (3)	0.005 (3)	0.013 (2)	0.002 (3)
C6	0.015 (3)	0.022 (3)	0.011 (3)	0.005 (2)	0.002 (2)	0.001 (2)
C7	0.046 (5)	0.042 (5)	0.024 (3)	−0.009 (4)	0.020 (3)	−0.012 (3)
C8	0.012 (3)	0.017 (3)	0.025 (3)	0.003 (2)	0.008 (2)	0.001 (3)
C9	0.013 (3)	0.016 (3)	0.011 (2)	0.006 (2)	0.000 (2)	−0.001 (2)
C10	0.019 (3)	0.020 (3)	0.027 (3)	−0.008 (3)	0.011 (3)	−0.008 (3)
C11	0.027 (4)	0.025 (4)	0.026 (3)	−0.016 (3)	0.007 (3)	−0.011 (3)
C12	0.011 (3)	0.023 (3)	0.019 (3)	−0.007 (2)	0.006 (2)	−0.001 (3)
C13	0.011 (3)	0.027 (3)	0.015 (3)	0.003 (2)	0.004 (2)	0.004 (3)
C14	0.015 (3)	0.033 (4)	0.022 (3)	0.006 (3)	0.006 (3)	0.004 (3)
C15	0.027 (4)	0.043 (4)	0.038 (4)	0.003 (3)	0.027 (3)	0.007 (3)
C16	0.014 (3)	0.029 (4)	0.031 (3)	0.008 (3)	0.014 (3)	0.000 (3)
C17	0.019 (3)	0.027 (3)	0.020 (3)	0.004 (3)	0.006 (2)	0.001 (3)
C18	0.029 (4)	0.038 (4)	0.052 (5)	0.000 (4)	0.011 (4)	−0.030 (4)
C19	0.012 (3)	0.019 (3)	0.024 (3)	0.005 (2)	0.006 (2)	−0.001 (3)
C20	0.009 (3)	0.026 (3)	0.015 (3)	0.002 (2)	0.001 (2)	0.001 (3)
C11A	0.012 (3)	0.026 (3)	0.017 (3)	−0.001 (2)	0.008 (2)	0.004 (3)
C12A	0.022 (3)	0.027 (4)	0.024 (3)	−0.002 (3)	−0.001 (3)	−0.004 (3)
C21A	0.017 (3)	0.028 (3)	0.019 (3)	0.006 (3)	0.008 (2)	−0.003 (3)
C22A	0.024 (3)	0.035 (4)	0.034 (4)	−0.004 (3)	0.011 (3)	0.007 (3)

Geometric parameters (Å, º) top

Co1—N2	1.861 (5)	C4—H4B	0.9800
Co1—N1	1.871 (5)	C4—H4C	0.9800
Co1—O2	1.887 (4)	C5—C6	1.391 (9)
Co1—O1	1.891 (4)	C5—H5A	0.9500
Co1—O21A	1.902 (5)	C6—C8	1.425 (9)
Co1—O11A	1.929 (4)	C7—H7A	0.9800
Co2—O12Aⁱ	2.043 (4)	C7—H7B	0.9800
Co2—O12A	2.043 (4)	C7—H7C	0.9800
Co2—O2ⁱ	2.117 (4)	C8—C9	1.451 (8)
Co2—O2	2.117 (4)	C9—H9A	0.9500
Co2—O1	2.160 (4)	C10—C11	1.511 (9)
Co2—O1ⁱ	2.160 (4)	C10—H10A	0.9900
Cl1—C	1.763 (10)	C10—H10B	0.9900
Cl2—C	1.771 (13)	C11—H11A	0.9900
O1—C1	1.310 (7)	C11—H11B	0.9900
O2—C20	1.334 (7)	C12—C13	1.432 (9)
O3—C3	1.361 (8)	C12—H12A	0.9500
O3—C4	1.441 (8)	C13—C14	1.411 (9)
O4—C6	1.342 (7)	C13—C20	1.418 (9)
O4—C7	1.440 (8)	C14—C16	1.385 (10)
O5—C14	1.380 (8)	C15—H15A	0.9800
O5—C15	1.431 (8)	C15—H15B	0.9800
O6—C17	1.353 (8)	C15—H15C	0.9800
O6—C18	1.432 (9)	C16—C17	1.393 (9)
O11A—C11A	1.275 (7)	C16—H16A	0.9500
O12A—C11A	1.256 (8)	C17—C19	1.397 (9)
O21A—C21A	1.293 (8)	C18—H18A	0.9800
O22A—C21A	1.226 (8)	C18—H18B	0.9800
N1—C9	1.282 (8)	C18—H18C	0.9800
N1—C10	1.465 (8)	C19—C20	1.400 (9)
N2—C12	1.281 (8)	C19—H19A	0.9500
N2—C11	1.485 (8)	C11A—C12A	1.491 (9)
C—H0A	0.9900	C12A—H12B	0.9800
C—H0B	0.9900	C12A—H12C	0.9800
C1—C2	1.411 (8)	C12A—H12D	0.9800
C1—C8	1.433 (8)	C21A—C22A	1.500 (10)
C2—C3	1.366 (9)	C22A—H22A	0.9800
C2—H2A	0.9500	C22A—H22B	0.9800
C3—C5	1.412 (9)	C22A—H22C	0.9800
C4—H4A	0.9800

N2—Co1—N1	86.4 (2)	O4—C7—H7A	109.5
N2—Co1—O2	93.9 (2)	O4—C7—H7B	109.5
N1—Co1—O2	178.7 (2)	H7A—C7—H7B	109.5
N2—Co1—O1	176.1 (2)	O4—C7—H7C	109.5
N1—Co1—O1	96.1 (2)	H7A—C7—H7C	109.5
O2—Co1—O1	83.65 (18)	H7B—C7—H7C	109.5
N2—Co1—O21A	96.4 (2)	C6—C8—C1	118.0 (6)
N1—Co1—O21A	91.4 (2)	C6—C8—C9	118.4 (6)
O2—Co1—O21A	89.90 (19)	C1—C8—C9	123.5 (6)
O1—Co1—O21A	86.66 (19)	N1—C9—C8	125.2 (6)
N2—Co1—O11A	86.1 (2)	N1—C9—H9A	117.4
N1—Co1—O11A	86.2 (2)	C8—C9—H9A	117.4
O2—Co1—O11A	92.57 (18)	N1—C10—C11	108.8 (5)
O1—Co1—O11A	90.98 (18)	N1—C10—H10A	109.9
O21A—Co1—O11A	176.38 (19)	C11—C10—H10A	109.9
O12Aⁱ—Co2—O12A	180.000 (1)	N1—C10—H10B	109.9
O12Aⁱ—Co2—O2ⁱ	86.78 (17)	C11—C10—H10B	109.9
O12A—Co2—O2ⁱ	93.22 (17)	H10A—C10—H10B	108.3
O12Aⁱ—Co2—O2	93.22 (17)	N2—C11—C10	108.0 (5)
O12A—Co2—O2	86.78 (17)	N2—C11—H11A	110.1
O2ⁱ—Co2—O2	180.0	C10—C11—H11A	110.1
O12Aⁱ—Co2—O1	92.92 (16)	N2—C11—H11B	110.1
O12A—Co2—O1	87.08 (16)	C10—C11—H11B	110.1
O2ⁱ—Co2—O1	107.85 (15)	H11A—C11—H11B	108.4
O2—Co2—O1	72.15 (15)	N2—C12—C13	124.7 (6)
O12Aⁱ—Co2—O1ⁱ	87.08 (16)	N2—C12—H12A	117.7
O12A—Co2—O1ⁱ	92.92 (16)	C13—C12—H12A	117.7
O2ⁱ—Co2—O1ⁱ	72.15 (15)	C14—C13—C20	117.5 (6)
O2—Co2—O1ⁱ	107.85 (15)	C14—C13—C12	119.5 (6)
O1—Co2—O1ⁱ	180.000 (1)	C20—C13—C12	123.0 (5)
C1—O1—Co1	125.3 (4)	O5—C14—C16	122.7 (6)
C1—O1—Co2	136.1 (4)	O5—C14—C13	114.7 (6)
Co1—O1—Co2	98.66 (17)	C16—C14—C13	122.6 (6)
C20—O2—Co1	122.9 (4)	O5—C15—H15A	109.5
C20—O2—Co2	135.6 (4)	O5—C15—H15B	109.5
Co1—O2—Co2	100.29 (18)	H15A—C15—H15B	109.5
C3—O3—C4	117.0 (5)	O5—C15—H15C	109.5
C6—O4—C7	117.7 (5)	H15A—C15—H15C	109.5
C14—O5—C15	116.9 (6)	H15B—C15—H15C	109.5
C17—O6—C18	118.9 (5)	C14—C16—C17	118.1 (6)
C11A—O11A—Co1	128.5 (4)	C14—C16—H16A	121.0
C11A—O12A—Co2	128.5 (4)	C17—C16—H16A	121.0
C21A—O21A—Co1	128.8 (4)	O6—C17—C16	115.1 (6)
C9—N1—C10	120.3 (5)	O6—C17—C19	122.8 (6)
C9—N1—Co1	125.0 (4)	C16—C17—C19	122.2 (6)
C10—N1—Co1	114.7 (4)	O6—C18—H18A	109.5
C12—N2—C11	122.4 (5)	O6—C18—H18B	109.5
C12—N2—Co1	125.5 (4)	H18A—C18—H18B	109.5
C11—N2—Co1	111.9 (4)	O6—C18—H18C	109.5
Cl1—C—Cl2	110.9 (7)	H18A—C18—H18C	109.5
Cl1—C—H0A	109.5	H18B—C18—H18C	109.5
Cl2—C—H0A	109.5	C17—C19—C20	118.8 (6)
Cl1—C—H0B	109.5	C17—C19—H19A	120.6
Cl2—C—H0B	109.5	C20—C19—H19A	120.6
H0A—C—H0B	108.0	O2—C20—C19	117.8 (5)
O1—C1—C2	118.2 (5)	O2—C20—C13	121.3 (6)
O1—C1—C8	122.0 (5)	C19—C20—C13	120.9 (6)
C2—C1—C8	119.8 (5)	O12A—C11A—O11A	126.6 (6)
C3—C2—C1	119.9 (6)	O12A—C11A—C12A	118.5 (5)
C3—C2—H2A	120.0	O11A—C11A—C12A	114.9 (6)
C1—C2—H2A	120.0	C11A—C12A—H12B	109.5
O3—C3—C2	124.1 (6)	C11A—C12A—H12C	109.5
O3—C3—C5	113.6 (6)	H12B—C12A—H12C	109.5
C2—C3—C5	122.3 (6)	C11A—C12A—H12D	109.5
O3—C4—H4A	109.5	H12B—C12A—H12D	109.5
O3—C4—H4B	109.5	H12C—C12A—H12D	109.5
H4A—C4—H4B	109.5	O22A—C21A—O21A	127.5 (6)
O3—C4—H4C	109.5	O22A—C21A—C22A	119.8 (6)
H4A—C4—H4C	109.5	O21A—C21A—C22A	112.8 (6)
H4B—C4—H4C	109.5	C21A—C22A—H22A	109.5
C6—C5—C3	118.5 (5)	C21A—C22A—H22B	109.5
C6—C5—H5A	120.8	H22A—C22A—H22B	109.5
C3—C5—H5A	120.8	C21A—C22A—H22C	109.5
O4—C6—C5	122.9 (5)	H22A—C22A—H22C	109.5
O4—C6—C8	115.8 (5)	H22B—C22A—H22C	109.5
C5—C6—C8	121.4 (6)

N1—Co1—O1—C1	18.7 (5)	Co2—O1—C1—C8	160.4 (4)
O2—Co1—O1—C1	−162.6 (5)	O1—C1—C2—C3	175.2 (5)
O21A—Co1—O1—C1	−72.3 (5)	C8—C1—C2—C3	−3.6 (8)
O11A—Co1—O1—C1	104.9 (5)	C4—O3—C3—C2	1.8 (9)
N1—Co1—O1—Co2	−160.9 (2)	C4—O3—C3—C5	179.5 (5)
O2—Co1—O1—Co2	17.86 (18)	C1—C2—C3—O3	178.4 (5)
O21A—Co1—O1—Co2	108.13 (19)	C1—C2—C3—C5	0.9 (9)
O11A—Co1—O1—Co2	−74.62 (18)	O3—C3—C5—C6	−176.8 (5)
O12Aⁱ—Co2—O1—C1	71.5 (5)	C2—C3—C5—C6	1.0 (9)
O12A—Co2—O1—C1	−108.5 (5)	C7—O4—C6—C5	4.5 (9)
O2ⁱ—Co2—O1—C1	−16.1 (6)	C7—O4—C6—C8	−175.5 (6)
O2—Co2—O1—C1	163.9 (6)	C3—C5—C6—O4	180.0 (5)
O12Aⁱ—Co2—O1—Co1	−109.03 (19)	C3—C5—C6—C8	−0.1 (9)
O12A—Co2—O1—Co1	70.97 (19)	O4—C6—C8—C1	177.4 (5)
O2ⁱ—Co2—O1—Co1	163.42 (17)	C5—C6—C8—C1	−2.5 (9)
O2—Co2—O1—Co1	−16.58 (17)	O4—C6—C8—C9	−1.7 (8)
N2—Co1—O2—C20	−32.5 (5)	C5—C6—C8—C9	178.4 (6)
O1—Co1—O2—C20	150.6 (5)	O1—C1—C8—C6	−174.4 (5)
O21A—Co1—O2—C20	63.9 (5)	C2—C1—C8—C6	4.4 (8)
O11A—Co1—O2—C20	−118.7 (5)	O1—C1—C8—C9	4.6 (9)
N2—Co1—O2—Co2	158.6 (2)	C2—C1—C8—C9	−176.6 (5)
O1—Co1—O2—Co2	−18.32 (19)	C10—N1—C9—C8	175.5 (6)
O21A—Co1—O2—Co2	−105.0 (2)	Co1—N1—C9—C8	−2.7 (8)
O11A—Co1—O2—Co2	72.4 (2)	C6—C8—C9—N1	−173.9 (6)
O12Aⁱ—Co2—O2—C20	−57.9 (6)	C1—C8—C9—N1	7.1 (9)
O12A—Co2—O2—C20	122.1 (6)	C9—N1—C10—C11	166.1 (6)
O1—Co2—O2—C20	−149.9 (6)	Co1—N1—C10—C11	−15.5 (7)
O1ⁱ—Co2—O2—C20	30.1 (6)	C12—N2—C11—C10	149.8 (6)
O12Aⁱ—Co2—O2—Co1	108.7 (2)	Co1—N2—C11—C10	−34.2 (6)
O12A—Co2—O2—Co1	−71.3 (2)	N1—C10—C11—N2	30.8 (7)
O1—Co2—O2—Co1	16.70 (17)	C11—N2—C12—C13	174.9 (6)
O1ⁱ—Co2—O2—Co1	−163.30 (17)	Co1—N2—C12—C13	−0.6 (9)
N2—Co1—O11A—C11A	−133.8 (5)	N2—C12—C13—C14	170.6 (6)
N1—Co1—O11A—C11A	139.6 (5)	N2—C12—C13—C20	−12.1 (10)
O2—Co1—O11A—C11A	−40.1 (5)	C15—O5—C14—C16	−0.3 (9)
O1—Co1—O11A—C11A	43.6 (5)	C15—O5—C14—C13	179.3 (6)
O2ⁱ—Co2—O12A—C11A	−140.5 (5)	C20—C13—C14—O5	−177.6 (5)
O2—Co2—O12A—C11A	39.5 (5)	C12—C13—C14—O5	−0.2 (9)
O1—Co2—O12A—C11A	−32.8 (5)	C20—C13—C14—C16	2.0 (10)
O1ⁱ—Co2—O12A—C11A	147.2 (5)	C12—C13—C14—C16	179.4 (6)
N2—Co1—O21A—C21A	−37.0 (6)	O5—C14—C16—C17	179.8 (6)
N1—Co1—O21A—C21A	49.5 (5)	C13—C14—C16—C17	0.2 (10)
O2—Co1—O21A—C21A	−130.8 (5)	C18—O6—C17—C16	173.6 (6)
O1—Co1—O21A—C21A	145.5 (5)	C18—O6—C17—C19	−6.2 (10)
N2—Co1—N1—C9	175.4 (5)	C14—C16—C17—O6	179.2 (6)
O1—Co1—N1—C9	−7.7 (5)	C14—C16—C17—C19	−0.9 (10)
O21A—Co1—N1—C9	79.1 (5)	O6—C17—C19—C20	179.1 (6)
O11A—Co1—N1—C9	−98.3 (5)	C16—C17—C19—C20	−0.8 (10)
N2—Co1—N1—C10	−2.9 (4)	Co1—O2—C20—C19	−153.3 (4)
O1—Co1—N1—C10	174.0 (4)	Co2—O2—C20—C19	11.0 (9)
O21A—Co1—N1—C10	−99.2 (4)	Co1—O2—C20—C13	29.1 (8)
O11A—Co1—N1—C10	83.4 (4)	Co2—O2—C20—C13	−166.6 (4)
N1—Co1—N2—C12	−162.8 (6)	C17—C19—C20—O2	−174.5 (6)
O2—Co1—N2—C12	18.5 (5)	C17—C19—C20—C13	3.1 (9)
O1—Co1—N2—C12	69 (3)	C14—C13—C20—O2	173.8 (6)
O21A—Co1—N2—C12	−71.9 (5)	C12—C13—C20—O2	−3.5 (9)
O11A—Co1—N2—C12	110.8 (5)	C14—C13—C20—C19	−3.6 (9)
N1—Co1—N2—C11	21.3 (4)	C12—C13—C20—C19	179.0 (6)
O2—Co1—N2—C11	−157.4 (4)	Co2—O12A—C11A—O11A	−4.4 (9)
O21A—Co1—N2—C11	112.3 (4)	Co2—O12A—C11A—C12A	175.4 (4)
O11A—Co1—N2—C11	−65.1 (4)	Co1—O11A—C11A—O12A	1.6 (9)
Co1—O1—C1—C2	162.2 (4)	Co1—O11A—C11A—C12A	−178.2 (4)
Co2—O1—C1—C2	−18.5 (8)	Co1—O21A—C21A—O22A	11.6 (10)
Co1—O1—C1—C8	−19.0 (8)	Co1—O21A—C21A—C22A	−167.3 (4)

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
C—H0A···O22A	0.99	2.33	3.269 (13)	158
C4—H4A···O6ⁱⁱ	0.98	2.35	3.326 (8)	175
C7—H7A···O6ⁱⁱⁱ	0.98	2.51	3.421 (9)	156
C11—H11A···O3ⁱⁱⁱ	0.99	2.62	3.602 (8)	174
C11—H11B···Cl1^iv	0.99	2.73	3.664 (8)	158
C15—H15A···O4^v	0.98	2.64	3.568 (10)	158
C12A—H12B···Cl1ⁱⁱⁱ	0.98	2.91	3.354 (8)	108

Symmetry codes: (ii) x+1/2, −y+3/2, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x+1/2, −y+1/2, z+1/2; (v) x−1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Co₃(C₂H₃O₂)₄(C₂₀H₂₂N₂O₆)₂]·2CH₂Cl₂
M_r	1355.61
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	110
a, b, c (Å)	13.9235 (9), 13.4407 (8), 16.0019 (11)
β (°)	112.724 (8)
V (Å³)	2762.2 (3)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	9.45
Crystal size (mm)	0.42 × 0.25 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.320, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10708, 5306, 3777
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.251, 1.03
No. of reflections	5306
No. of parameters	373
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.11, −1.66

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), 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
C—H0A···O22A	0.99	2.33	3.269 (13)	158
C4—H4A···O6ⁱ	0.98	2.35	3.326 (8)	175
C7—H7A···O6ⁱⁱ	0.98	2.51	3.421 (9)	156
C11—H11A···O3ⁱⁱ	0.99	2.62	3.602 (8)	174
C11—H11B···Cl1ⁱⁱⁱ	0.99	2.73	3.664 (8)	158
C15—H15A···O4^iv	0.98	2.64	3.568 (10)	158
C12A—H12B···Cl1ⁱⁱ	0.98	2.91	3.354 (8)	108

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) x−1/2, −y+1/2, z+1/2.

Acknowledgements

RJB wishes to acknowledge the NSF-MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

References

Babushkin, D. E. & Talsi, E. P. (1998). J. Mol. Catal. A, 130, 131–137. CrossRef CAS Google Scholar
Chattopadhyay, S., Bocelli, G., Musatti, A. & Ghosh, A. (2006). Inorg. Chem. Commun. 9, 1053–1057. Web of Science CSD CrossRef CAS Google Scholar
Chattopadhyay, S., Drew, G. B. M. & Ghosh, A. (2008). Eur. J. Inorg. Chem. pp. 1693–1701. Web of Science CSD CrossRef Google Scholar
Dong, W., Shi, J., Xu, L., Zhong, J., Duan, J. & Zhang, Y. (2008). Appl. Organomet. Chem. 22, 89–96. Web of Science CrossRef CAS Google Scholar
Gerli, A., Hagen, K. S. & Marzilli, L. G. (1991). Inorg. Chem. 30, 4673–4676. CSD CrossRef CAS Web of Science Google Scholar
He, X., Lu, C.-Z. & Wu, C.-D. (2006). J. Coord. Chem 59, 977–984. Web of Science CSD CrossRef CAS Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, D.-H., You, Z.-L., Xu, C., Zhang, Q. & Zhu, H.-L. (2007). Inorg. Chem. Commun. 10, 404–406. Web of Science CSD CrossRef Google Scholar
You, Z.-L., Shi, D.-H., Xu, C., Zhang, Q. & Zhu, H.-L. (2008). Eur. J. Med. Chem. 43, 862–871. Web of Science CrossRef PubMed CAS Google Scholar
You, Z.-L. & Zhou, P. (2007). Inorg. Chem. Commun. 10, 1273–1275. Web of Science CSD CrossRef CAS Google Scholar
You, Z.-L. & Zhu, H.-L. (2004). Z. Anorg. Allg. Chem. 630, 2754–2760. Web of Science CSD CrossRef CAS Google Scholar
You, Z.-L., Zhu, H.-L. & Liu, W.-S. (2004). Acta Cryst. E60, m1900–m1902. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yu, T., Zhang, K., Zhao, Y., Yang, C., Zhang, H., Fan, D. & Dong, W. (2007). Inorg. Chem. Commun. 10, 401–403. Web of Science CSD CrossRef CAS Google Scholar
Yu, T., Zhang, K., Zhao, Y., Yang, C., Zhang, H., Qian, L., Fan, D., Dong, W., Chen, L. & Qiu, Y. (2008). Inorg. Chim. Acta, 361, 233–240. Web of Science CSD CrossRef CAS Google Scholar

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