Di-μ(2)-acetato-diacetato-bis-{μ(2)-3,3',5,5'-tetra-meth-oxy-2,2-[ethane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolato}tricobalt(II,III) dichloro-methane disolvate.

The trinuclear title compound, [Co(3)(CH(3)COO)(4)(C(20)H(22)N(2)O(6))(2)]·2CH(2)Cl(2), contains mixed-valence cobalt ions in the following order Co(III)-Co(II)-Co(III) where all the three cobalt ions are hexa-coordinated. 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 hexa-coordinated 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 inter-molecular C-H⋯O inter-actions involving the meth-oxy groups, as well as inter-molecular C-H⋯O inter-actions involving the acetate anions. In addition, the dichoromethane solvate mol-ecules are held in place by weak C-H⋯Cl inter-actions.

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 = 1355.61

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.251

S = 1.03

5306 reflections

373 parameters

H-atom parameters constrained

Δρmax = 1.11 e Å−3

Δρmin = −1.66 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003783/jj2072sup1.cif

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

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

[Co3(C2H3O2)4(C20H22N2O6)2]·2CH2Cl2	F(000) = 1394
Mr = 1355.61	Dx = 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

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	Rint = 0.043
Detector resolution: 10.5081 pixels mm-1	θmax = 74.2°, θmin = 4.5°
ω scans	h = −17→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −16→13
Tmin = 0.320, Tmax = 1.000	l = −19→18
10708 measured reflections

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(Fo2) + (0.1718P)2 + 2.5393P] where P = (Fo2 + 2Fc2)/3
5306 reflections	(Δ/σ)max < 0.001
373 parameters	Δρmax = 1.11 e Å−3
0 restraints	Δρmin = −1.66 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 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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···Cl1iv	0.99	2.73	3.664 (8)	158
C15—H15A···O4v	0.98	2.64	3.568 (10)	158
C12A—H12B···Cl1iii	0.98	2.91	3.354 (8)	108

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⋯O4iv	0.98	2.64	3.568 (10)	158
C12A—H12B⋯Cl1ii	0.98	2.91	3.354 (8)	108

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .