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

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).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.052
• wR factor = 0.150
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT213_ALERT_2_B Atom C10             has ADP max/min Ratio .....       4.50 prola
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N1     --  C9      ..      10.68 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N2     --  C10     ..      23.35 su
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C10

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.87 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.91 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     --  C11     ..       6.45 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         Co
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.10
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..          7
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ          ?
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       2.00 Ratio

Alert level G
PLAT301_ALERT_3_G Note: Main Residue  Disorder ...................      15.00 Perc.
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         30
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.19 Ratio
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      33.20 Deg.
              C12  -N2   -C12'    1.555   1.555   1.555
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          !

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

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

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

Carbon-bound H-atoms were placed in calculated positions with C—H = 0.93 - 0.98 Å, and were included in the refinement in the riding model approximation, with U(H) set to 1.2U_eq(C).

Disorder was noted in bridging 1,4-bix ligand. Two positions were discerned for the -H₂C(C₆H₄₎CH₂- residue. From refinement, the major component had a site occupancy of 0.512 (9). Multiple positions were not resolved for the imidazole ring, even though several of the atoms exhibited elongated displacement ellipsoids. The atoms of this ring were restrained to be approximately isotropic with application of the ISOR command in SHELXL-97 (Sheldrick, 2008).

The maximum and minimum residual electron density peaks of 1.34 and -1.40 eÅ^-3, respectively, were located 0.08 Å and 0.05 Å from the N1 and N2 atoms, respectively.

Computing details

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

	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)]

Crystal data

[Co2(C8H10O4)2(C14H14N4)]	Z = 1
Mr = 696.48	F(000) = 360
Triclinic, P1	Dx = 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) Å^3

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0864P)^2 + 1.1188P] where P = (Fo^2 + 2Fc^2)/3
2663 reflections	(Δ/σ)max = 0.001
206 parameters	Δρmax = 1.34 e Å^−3
30 restraints	Δρmin = −1.40 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Co—O2^i	2.008 (3)	C6—H6B	0.9700
Co—O3^ii	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—O4^iii	2.117 (3)	C9—H9	0.9300
Co—Co^i	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—Co^i	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—Co^iii	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
O2^i—Co—O3^ii	91.45 (14)	C2—C7—C6	111.7 (3)
O2^i—Co—O1	164.36 (13)	C2—C7—H7A	109.3
O3^ii—Co—O1	90.51 (14)	C6—C7—H7A	109.3
O2^i—Co—N1	98.07 (16)	C2—C7—H7B	109.3
O3^ii—Co—N1	104.53 (16)	C6—C7—H7B	109.3
O1—Co—N1	96.44 (16)	H7A—C7—H7B	107.9
O2^i—Co—O4^iii	88.63 (14)	O4—C8—O3	123.1 (4)
O3^ii—Co—O4^iii	164.38 (14)	O4—C8—C5	118.6 (4)
O1—Co—O4^iii	85.35 (13)	O3—C8—C5	118.3 (4)
N1—Co—O4^iii	90.91 (16)	N1—C9—C10	105.5 (7)
O2^i—Co—Co^i	81.73 (9)	N1—C9—H9	127.3
O3^ii—Co—Co^i	97.00 (10)	C10—C9—H9	127.3
O1—Co—Co^i	82.63 (9)	N2—C10—C9	109.2 (5)
N1—Co—Co^i	158.46 (13)	N2—C10—H10	125.4
O4^iii—Co—Co^i	67.55 (10)	C9—C10—H10	125.4
C1—O1—Co	124.3 (3)	N2—C11—N1	112.8 (6)
C1—O2—Co^i	127.3 (3)	N2—C11—H11	123.6
C8—O3—Co^iv	109.5 (3)	N1—C11—H11	123.6
C8—O4—Co^iii	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
O2^i—Co—O1—C1	3.5 (7)	Co^iv—O3—C8—O4	−5.3 (5)
O3^ii—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)
O4^iii—Co—O1—C1	−64.2 (3)	C6—C5—C8—O4	−26.8 (5)
Co^i—Co—O1—C1	3.7 (3)	C4—C5—C8—O3	28.5 (5)
O2^i—Co—N1—C11	−139.8 (4)	C6—C5—C8—O3	155.4 (4)
O3^ii—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)
O4^iii—Co—N1—C11	−51.1 (4)	N1—C9—C10—N2	−0.2 (7)
Co^i—Co—N1—C11	−51.9 (6)	C9—N1—C11—N2	1.2 (6)
O2^i—Co—N1—C9	40.6 (5)	Co—N1—C11—N2	−178.5 (3)
O3^ii—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)
O4^iii—Co—N1—C9	129.3 (5)	C9—C10—N2—C12'	177.2 (8)
Co^i—Co—N1—C9	128.5 (5)	N1—C11—N2—C10	−1.3 (6)
Co^i—O2—C1—O1	8.4 (6)	N1—C11—N2—C12	177.0 (12)
Co^i—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)
Co^iii—O4—C8—O3	12.1 (8)	C14'—C13'—C15'—C14'^v	−12 (3)
Co^iii—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.