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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1549.
Published online 2010 November 13. doi:  10.1107/S160053681004568X
PMCID: PMC3011569

Bis[μ-2,2′-dimethyl-1,1′-(3-oxapentane-1,5-di­yl)di-1H-benzimidazole-κ2 N 3:N 3′]bis­[bis­(4-meth­oxy­benzoato)-κO2 O,O′-cobalt(II)]

Abstract

The complete mol­ecule of the title complex, [Co2(C8H7O3)4(C20H22N4O)2], is a dimer of the paddle-wheel-type generated by crystallographic inversion symmetry. The CoII ion is penta­coordinated by three O atoms from two 4-meth­oxy­benzoate anions (one bidentate and one monodentate) and two N atoms from two 2,2′-bis­(2-methyl-1H-benzimidazole)­ether ligands. This results in a very distorted trigonal–bipyramidal geometry for the metal ion, with both N atoms in equatorial sites. The dihedral angle between the benzimidazole ring systems in the ligand is 60.04 (8)°. The configuration of the mol­ecule is supported by intra­molecular C—H(...)O hydrogen bonds.

Related literature

For background to benzimidazole ligands in coordination polymers, see: Hoskins et al. (1997 [triangle]). For a related structure, see: Dimitrou et al. (1999 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1549-scheme1.jpg

Experimental

Crystal data

  • [Co2(C8H7O3)4(C20H22N4O)2]
  • M r = 1391.24
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1549-efi1.jpg
  • a = 12.4127 (3) Å
  • b = 16.3933 (4) Å
  • c = 17.6106 (5) Å
  • β = 109.577 (3)°
  • V = 3376.34 (15) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.56 mm−1
  • T = 293 K
  • 0.32 × 0.28 × 0.24 mm

Data collection

  • Oxford Diffraction Gemini R Ultra CCD diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 [triangle]) T min = 0.829, T max = 0.889
  • 14632 measured reflections
  • 7801 independent reflections
  • 3677 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.081
  • S = 0.75
  • 7801 reflections
  • 433 parameters
  • H-atom parameters constrained
  • Δρmax = 0.48 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 [triangle]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004568X/hb5721sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004568X/hb5721Isup2.hkl

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

Acknowledgments

The author thanks BoHai University for support.

supplementary crystallographic information

Comment

Bis(imidazole) ligands with –CH2– spacers are a good candidate for N-donor bridging ligand (Hoskins et al., 1997). Up to now, 2,2'-bis(2-methyl-1H-benzimidazole)ether ligands, as a flexible ligand, is rarely investigated in constructing coordination polymers.

In the title compound (Fig. 1), the CoII ion is pentacoordinated by three O atoms from two 4-methoxybenzoate anions, and two N atoms from two 2,2'-bis(2-methyl-1H-benzimidazole)ether ligand. The Co—O distances are found in the range from 1.9694 (14) to 2.374 (2) Å, which is similar to previous report (Dimitrou et al., 1999). The Co—N distances are 2.0524 (18) and 2.0598 (18) Å, respectively. The crystal structure is stabilized by a weak intermolecular C—H···O hydrogen bond between the benzene H atom of 2-methyl-1H-benzimidazole ring and the O atom of diethyl ether group, with a C17—H015···O6; the methyl H atoms of 2-methyl-1H-benzimidazole ligands and the carboxylate O atoms with C8—H8c—O2 and C20—H03B—O2 (Table 1 & Fig. 2).

Experimental

An aqueous solution (10 ml) of 4-methoxybenzoic acid (0.072 g, 0.4 mmol), 2,2'-bis(2-methylbenzimidazole)ether (0.065 g, 0.2 mmol) and Co(Ac)2 (0.049 g, 0.2 mmol) was added in and sealed in 18 ml Teflon-lined stainless steel container. The container was heated to 130 °C and held at that temperature for 72 h, then cooled to room temperature at a rate of 10 °C.h-1. And then the title compound was isolated as purple blocks.

Refinement

C–bound H–atoms were geometrically positioned (C—H 0.93 Å) and refined using a riding model, with Uiso = 1.2Ueq (C).

Figures

Fig. 1.
The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [symmetry code: (i) - x + 1, - y, - z + 1.]
Fig. 2.
C—H···O interactions (dotted lines) in the title compound.: [symmetry code: (i) -x + 1, -y, -z + 1.]

Crystal data

[Co2(C8H7O3)4(C20H22N4O)2]F(000) = 1452
Mr = 1391.24Dx = 1.368 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7801 reflections
a = 12.4127 (3) Åθ = 3.0–29.2°
b = 16.3933 (4) ŵ = 0.56 mm1
c = 17.6106 (5) ÅT = 293 K
β = 109.577 (3)°Block, purple
V = 3376.34 (15) Å30.32 × 0.28 × 0.24 mm
Z = 2

Data collection

Oxford Diffraction Gemini R Ultra CCD diffractometer7801 independent reflections
Radiation source: fine-focus sealed tube3677 reflections with I > 2σ(I)
graphiteRint = 0.030
Detector resolution: 10.0 pixels mm-1θmax = 29.2°, θmin = 3.1°
ω scansh = −15→17
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)k = −21→22
Tmin = 0.829, Tmax = 0.889l = −23→23
14632 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H-atom parameters constrained
S = 0.75w = 1/[σ2(Fo2) + (0.0363P)2] where P = (Fo2 + 2Fc2)/3
7801 reflections(Δ/σ)max = 0.002
433 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = −0.24 e Å3

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 (Å2)

xyzUiso*/Ueq
Co10.78779 (2)0.131671 (18)0.654674 (17)0.03902 (10)
C10.85504 (17)−0.01846 (14)0.47885 (14)0.0403 (6)
C20.89543 (19)−0.09166 (17)0.45938 (17)0.0565 (7)
H0300.8957−0.10220.40760.068*
C30.9350 (2)−0.14773 (16)0.5202 (2)0.0657 (8)
H0260.9626−0.19760.50940.079*
C40.9347 (2)−0.13176 (17)0.59687 (19)0.0636 (8)
H0460.9621−0.17130.63650.076*
C50.89485 (18)−0.05868 (15)0.61701 (15)0.0495 (6)
H0190.8951−0.04830.66900.059*
C60.85452 (17)−0.00168 (13)0.55553 (13)0.0364 (5)
C70.78846 (17)0.10552 (13)0.48290 (13)0.0386 (6)
C80.7453 (2)0.18927 (14)0.45810 (14)0.0581 (7)
H8A0.73400.19660.40190.087*
H8B0.80000.22840.48910.087*
H8C0.67400.19690.46730.087*
C90.79201 (19)0.05843 (17)0.34709 (13)0.0538 (7)
H9A0.85640.03590.33460.065*
H9B0.78520.11560.33220.065*
C100.68383 (19)0.01401 (16)0.29879 (14)0.0551 (7)
H10A0.67570.01620.24210.066*
H10B0.6902−0.04290.31490.066*
C110.53616 (19)0.11094 (16)0.25483 (16)0.0604 (8)
H11A0.51610.09140.19980.073*
H11B0.58950.15580.26210.073*
C120.4298 (2)0.13882 (15)0.27170 (16)0.0590 (7)
H12A0.45110.15900.32660.071*
H12B0.39420.18320.23560.071*
C130.27905 (18)0.04282 (15)0.18685 (14)0.0425 (6)
C140.2593 (2)0.07031 (17)0.10893 (16)0.0606 (7)
H0470.29540.11640.09820.073*
C150.1834 (2)0.0255 (2)0.04845 (16)0.0692 (8)
H0310.16780.0419−0.00470.083*
C160.1298 (2)−0.04286 (19)0.06417 (15)0.0614 (8)
H0370.0792−0.07130.02130.074*
C170.14893 (18)−0.07034 (15)0.14168 (13)0.0476 (6)
H0150.1121−0.11630.15200.057*
C180.22604 (17)−0.02586 (14)0.20371 (12)0.0376 (5)
C190.33864 (17)0.02086 (14)0.31804 (14)0.0419 (6)
C200.4034 (2)0.03192 (16)0.40569 (13)0.0584 (7)
H03A0.45120.07930.41310.088*
H03B0.4500−0.01530.42580.088*
H03C0.35050.03880.43440.088*
C210.50942 (19)0.27294 (15)0.61817 (15)0.0480 (6)
C220.52284 (19)0.34163 (15)0.66575 (15)0.0516 (7)
H0240.59520.35540.70060.062*
C230.43083 (19)0.39010 (15)0.66240 (14)0.0504 (6)
H0290.44140.43640.69460.061*
C240.32260 (17)0.36994 (15)0.61112 (13)0.0423 (6)
C250.3085 (2)0.30181 (15)0.56284 (14)0.0490 (6)
H0340.23640.28800.52760.059*
C260.4016 (2)0.25449 (15)0.56708 (14)0.0541 (7)
H0230.39130.20860.53440.065*
C270.6097 (3)0.21856 (18)0.6219 (2)0.0646 (8)
C280.1242 (2)0.40712 (18)0.55740 (16)0.0730 (9)
H04A0.07250.44680.56580.109*
H04B0.09880.35340.56500.109*
H04C0.12600.41210.50350.109*
C291.13722 (17)0.17700 (13)0.74857 (13)0.0355 (5)
C301.21576 (17)0.21342 (13)0.71996 (13)0.0408 (6)
H0331.18970.24500.67350.049*
C311.33219 (17)0.20458 (14)0.75815 (14)0.0448 (6)
H0221.38370.22890.73700.054*
C321.37090 (19)0.15926 (14)0.82796 (14)0.0447 (6)
C331.29372 (19)0.12518 (15)0.85978 (14)0.0488 (6)
H0321.32000.09700.90830.059*
C341.17833 (18)0.13266 (14)0.82017 (13)0.0439 (6)
H0141.12710.10800.84120.053*
C351.01124 (18)0.18316 (15)0.70171 (14)0.0412 (6)
C361.5609 (2)0.14637 (19)0.82543 (18)0.0758 (9)
H04D1.63680.13500.86120.114*
H04E1.55930.19940.80190.114*
H04F1.53890.10600.78350.114*
N10.81165 (14)0.07684 (10)0.55674 (10)0.0370 (4)
N20.81263 (14)0.05087 (12)0.43346 (10)0.0406 (5)
N30.34858 (14)0.07201 (11)0.26072 (11)0.0447 (5)
N40.26514 (13)−0.03898 (11)0.28711 (10)0.0380 (4)
O10.58565 (13)0.04771 (9)0.30952 (9)0.0513 (4)
O20.59500 (18)0.15921 (14)0.57565 (13)0.0890 (7)
O30.70491 (15)0.23292 (11)0.67326 (14)0.0804 (6)
O40.23632 (13)0.42058 (10)0.61380 (10)0.0609 (5)
O50.97677 (12)0.22669 (10)0.64168 (10)0.0526 (4)
O60.94624 (12)0.14002 (11)0.72914 (9)0.0554 (5)
O71.48382 (13)0.14450 (12)0.86905 (10)0.0731 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co10.03659 (16)0.04231 (18)0.04015 (18)−0.00346 (15)0.01550 (13)−0.00498 (16)
C10.0299 (11)0.0410 (15)0.0488 (15)−0.0039 (11)0.0118 (11)−0.0119 (12)
C20.0386 (13)0.0638 (18)0.0658 (18)−0.0066 (13)0.0158 (13)−0.0274 (16)
C30.0438 (14)0.0472 (18)0.100 (2)0.0032 (13)0.0161 (16)−0.0228 (18)
C40.0500 (15)0.0445 (16)0.091 (2)0.0081 (14)0.0161 (15)0.0103 (16)
C50.0454 (13)0.0489 (16)0.0532 (15)0.0048 (12)0.0154 (12)0.0050 (13)
C60.0323 (11)0.0365 (14)0.0418 (14)−0.0036 (10)0.0143 (10)−0.0048 (11)
C70.0377 (12)0.0388 (14)0.0414 (14)−0.0060 (10)0.0159 (11)0.0002 (11)
C80.0724 (17)0.0465 (16)0.0559 (16)0.0027 (14)0.0223 (13)0.0081 (13)
C90.0452 (13)0.0805 (19)0.0418 (15)−0.0028 (13)0.0226 (12)−0.0048 (13)
C100.0534 (15)0.0639 (18)0.0432 (15)0.0025 (14)0.0099 (12)−0.0089 (13)
C110.0445 (14)0.0584 (18)0.0762 (18)−0.0063 (13)0.0174 (13)0.0259 (15)
C120.0530 (15)0.0412 (15)0.0800 (19)−0.0060 (13)0.0188 (13)0.0124 (14)
C130.0346 (12)0.0507 (15)0.0443 (15)0.0092 (11)0.0158 (11)0.0094 (12)
C140.0545 (15)0.0720 (19)0.0570 (17)0.0119 (15)0.0208 (14)0.0236 (15)
C150.0663 (18)0.102 (2)0.0412 (16)0.0232 (18)0.0205 (15)0.0208 (16)
C160.0471 (15)0.094 (2)0.0393 (16)0.0109 (16)0.0097 (13)−0.0081 (15)
C170.0373 (12)0.0633 (17)0.0426 (14)0.0018 (12)0.0139 (11)−0.0062 (13)
C180.0319 (11)0.0471 (14)0.0352 (13)0.0068 (11)0.0131 (10)0.0011 (11)
C190.0325 (12)0.0476 (15)0.0476 (14)−0.0042 (11)0.0161 (11)−0.0021 (12)
C200.0495 (14)0.0718 (19)0.0480 (15)−0.0159 (13)0.0086 (12)−0.0107 (13)
C210.0462 (14)0.0453 (16)0.0622 (17)0.0049 (12)0.0312 (13)0.0082 (13)
C220.0394 (13)0.0496 (16)0.0640 (17)−0.0047 (12)0.0147 (12)0.0030 (13)
C230.0496 (14)0.0457 (15)0.0547 (15)−0.0037 (12)0.0158 (12)−0.0076 (12)
C240.0420 (13)0.0437 (14)0.0440 (13)0.0039 (12)0.0180 (11)0.0003 (12)
C250.0478 (14)0.0511 (16)0.0468 (15)−0.0040 (13)0.0142 (12)−0.0057 (13)
C260.0627 (17)0.0464 (15)0.0573 (16)0.0002 (14)0.0256 (14)−0.0089 (13)
C270.068 (2)0.0535 (19)0.086 (2)0.0103 (16)0.0438 (18)0.0239 (17)
C280.0494 (15)0.085 (2)0.0741 (19)0.0162 (15)0.0070 (14)0.0024 (16)
C290.0339 (11)0.0330 (12)0.0432 (14)−0.0032 (10)0.0176 (10)−0.0074 (11)
C300.0419 (13)0.0370 (13)0.0434 (13)0.0013 (11)0.0142 (11)0.0033 (11)
C310.0358 (12)0.0461 (15)0.0564 (16)−0.0041 (11)0.0205 (11)0.0006 (12)
C320.0379 (13)0.0468 (15)0.0476 (15)0.0057 (11)0.0120 (12)−0.0079 (12)
C330.0539 (15)0.0495 (15)0.0432 (14)0.0120 (13)0.0165 (12)0.0063 (12)
C340.0474 (13)0.0411 (13)0.0497 (14)−0.0044 (12)0.0246 (11)−0.0009 (13)
C350.0394 (13)0.0437 (15)0.0446 (15)−0.0020 (12)0.0193 (12)−0.0161 (13)
C360.0433 (14)0.090 (2)0.094 (2)0.0140 (15)0.0239 (15)−0.0113 (18)
N10.0407 (10)0.0347 (11)0.0382 (11)0.0001 (9)0.0167 (8)−0.0010 (9)
N20.0409 (10)0.0501 (12)0.0348 (11)−0.0058 (9)0.0178 (9)−0.0049 (10)
N30.0380 (10)0.0427 (12)0.0528 (13)−0.0033 (9)0.0145 (10)0.0080 (10)
N40.0326 (9)0.0463 (12)0.0356 (11)−0.0060 (9)0.0122 (8)−0.0019 (9)
O10.0439 (9)0.0492 (10)0.0611 (11)0.0013 (8)0.0180 (8)0.0112 (9)
O20.1034 (16)0.0903 (17)0.0858 (15)0.0400 (13)0.0482 (12)−0.0019 (13)
O30.0442 (11)0.0576 (12)0.1416 (18)0.0037 (9)0.0341 (11)0.0070 (12)
O40.0474 (9)0.0658 (12)0.0642 (11)0.0129 (9)0.0115 (9)−0.0133 (9)
O50.0443 (9)0.0537 (11)0.0530 (11)0.0047 (8)0.0074 (8)−0.0008 (9)
O60.0406 (9)0.0787 (12)0.0501 (10)−0.0164 (9)0.0196 (8)−0.0075 (9)
O70.0366 (9)0.1133 (17)0.0645 (12)0.0192 (10)0.0106 (9)0.0039 (11)

Geometric parameters (Å, °)

Co1—O61.9694 (14)C17—C181.393 (3)
Co1—O32.0362 (18)C17—H0150.9300
Co1—N12.0524 (18)C18—N41.401 (3)
Co1—N4i2.0598 (18)C19—N41.326 (3)
Co1—O22.374 (2)C19—N31.349 (3)
C1—C61.380 (3)C19—C201.493 (3)
C1—C21.387 (3)C20—H03A0.9600
C1—N21.388 (3)C20—H03B0.9600
C2—C31.372 (4)C20—H03C0.9600
C2—H0300.9300C21—C261.373 (3)
C3—C41.377 (4)C21—C221.380 (3)
C3—H0260.9300C21—C271.515 (4)
C4—C51.387 (3)C22—C231.376 (3)
C4—H0460.9300C22—H0240.9300
C5—C61.390 (3)C23—C241.384 (3)
C5—H0190.9300C23—H0290.9300
C6—N11.396 (3)C24—O41.368 (3)
C7—N11.321 (3)C24—C251.379 (3)
C7—N21.351 (3)C25—C261.372 (3)
C7—C81.485 (3)C25—H0340.9300
C8—H8A0.9600C26—H0230.9300
C8—H8B0.9600C27—O21.243 (3)
C8—H8C0.9600C27—O31.246 (3)
C9—N21.461 (3)C28—O41.430 (3)
C9—C101.514 (3)C28—H04A0.9600
C9—H9A0.9700C28—H04B0.9600
C9—H9B0.9700C28—H04C0.9600
C10—O11.407 (3)C29—C301.375 (3)
C10—H10A0.9700C29—C341.395 (3)
C10—H10B0.9700C29—C351.507 (3)
C11—O11.408 (3)C30—C311.382 (3)
C11—C121.517 (3)C30—H0330.9300
C11—H11A0.9700C31—C321.378 (3)
C11—H11B0.9700C31—H0220.9300
C12—N31.457 (3)C32—O71.366 (2)
C12—H12A0.9700C32—C331.380 (3)
C12—H12B0.9700C33—C341.372 (3)
C13—N31.383 (3)C33—H0320.9300
C13—C181.386 (3)C34—H0140.9300
C13—C141.386 (3)C35—O51.228 (3)
C14—C151.374 (4)C35—O61.283 (3)
C14—H0470.9300C36—O71.414 (3)
C15—C161.379 (4)C36—H04D0.9600
C15—H0310.9300C36—H04E0.9600
C16—C171.380 (3)C36—H04F0.9600
C16—H0370.9300N4—Co1i2.0598 (18)
O6—Co1—O3106.38 (8)N4—C19—C20124.9 (2)
O6—Co1—N1101.35 (7)N3—C19—C20123.1 (2)
O3—Co1—N1135.65 (8)C19—C20—H03A109.5
O6—Co1—N4i97.69 (7)C19—C20—H03B109.5
O3—Co1—N4i104.99 (8)H03A—C20—H03B109.5
N1—Co1—N4i104.77 (7)C19—C20—H03C109.5
O6—Co1—O2164.33 (8)H03A—C20—H03C109.5
O3—Co1—O258.32 (7)H03B—C20—H03C109.5
N1—Co1—O289.52 (7)C26—C21—C22118.1 (2)
N4i—Co1—O290.29 (7)C26—C21—C27120.4 (2)
C6—C1—C2122.3 (2)C22—C21—C27121.6 (2)
C6—C1—N2105.97 (19)C23—C22—C21121.0 (2)
C2—C1—N2131.7 (2)C23—C22—H024119.5
C3—C2—C1116.8 (3)C21—C22—H024119.5
C3—C2—H030121.6C22—C23—C24120.0 (2)
C1—C2—H030121.6C22—C23—H029120.0
C2—C3—C4121.4 (3)C24—C23—H029120.0
C2—C3—H026119.3O4—C24—C25125.03 (19)
C4—C3—H026119.3O4—C24—C23115.6 (2)
C3—C4—C5122.3 (3)C25—C24—C23119.4 (2)
C3—C4—H046118.9C26—C25—C24119.6 (2)
C5—C4—H046118.9C26—C25—H034120.2
C4—C5—C6116.6 (2)C24—C25—H034120.2
C4—C5—H019121.7C25—C26—C21121.9 (2)
C6—C5—H019121.7C25—C26—H023119.0
C1—C6—C5120.6 (2)C21—C26—H023119.0
C1—C6—N1109.00 (19)O2—C27—O3121.3 (3)
C5—C6—N1130.4 (2)O2—C27—C21119.6 (3)
N1—C7—N2112.09 (19)O3—C27—C21119.1 (3)
N1—C7—C8123.8 (2)O4—C28—H04A109.5
N2—C7—C8124.0 (2)O4—C28—H04B109.5
C7—C8—H8A109.5H04A—C28—H04B109.5
C7—C8—H8B109.5O4—C28—H04C109.5
H8A—C8—H8B109.5H04A—C28—H04C109.5
C7—C8—H8C109.5H04B—C28—H04C109.5
H8A—C8—H8C109.5C30—C29—C34117.89 (19)
H8B—C8—H8C109.5C30—C29—C35120.2 (2)
N2—C9—C10110.9 (2)C34—C29—C35121.9 (2)
N2—C9—H9A109.5C29—C30—C31122.0 (2)
C10—C9—H9A109.5C29—C30—H033119.0
N2—C9—H9B109.5C31—C30—H033119.0
C10—C9—H9B109.5C32—C31—C30119.1 (2)
H9A—C9—H9B108.0C32—C31—H022120.5
O1—C10—C9112.4 (2)C30—C31—H022120.5
O1—C10—H10A109.1O7—C32—C31123.9 (2)
C9—C10—H10A109.1O7—C32—C33116.2 (2)
O1—C10—H10B109.1C31—C32—C33119.9 (2)
C9—C10—H10B109.1C34—C33—C32120.4 (2)
H10A—C10—H10B107.9C34—C33—H032119.8
O1—C11—C12107.3 (2)C32—C33—H032119.8
O1—C11—H11A110.3C33—C34—C29120.6 (2)
C12—C11—H11A110.3C33—C34—H014119.7
O1—C11—H11B110.3C29—C34—H014119.7
C12—C11—H11B110.3O5—C35—O6124.3 (2)
H11A—C11—H11B108.5O5—C35—C29120.6 (2)
N3—C12—C11110.9 (2)O6—C35—C29115.1 (2)
N3—C12—H12A109.5O7—C36—H04D109.5
C11—C12—H12A109.5O7—C36—H04E109.5
N3—C12—H12B109.5H04D—C36—H04E109.5
C11—C12—H12B109.5O7—C36—H04F109.5
H12A—C12—H12B108.1H04D—C36—H04F109.5
N3—C13—C18105.72 (19)H04E—C36—H04F109.5
N3—C13—C14131.8 (2)C7—N1—C6105.77 (18)
C18—C13—C14122.5 (2)C7—N1—Co1128.77 (15)
C15—C14—C13116.2 (3)C6—N1—Co1125.44 (14)
C15—C14—H047121.9C7—N2—C1107.17 (18)
C13—C14—H047121.9C7—N2—C9128.0 (2)
C14—C15—C16122.0 (2)C1—N2—C9124.7 (2)
C14—C15—H031119.0C19—N3—C13107.69 (18)
C16—C15—H031119.0C19—N3—C12126.91 (18)
C15—C16—C17122.0 (2)C13—N3—C12124.8 (2)
C15—C16—H037119.0C19—N4—C18105.43 (18)
C17—C16—H037119.0C19—N4—Co1i129.17 (15)
C16—C17—C18116.7 (2)C18—N4—Co1i125.38 (14)
C16—C17—H015121.6C10—O1—C11113.34 (19)
C18—C17—H015121.6C27—O2—Co182.33 (17)
C13—C18—C17120.5 (2)C27—O3—Co197.85 (18)
C13—C18—N4109.08 (18)C24—O4—C28118.24 (18)
C17—C18—N4130.4 (2)C35—O6—Co1113.66 (14)
N4—C19—N3112.04 (19)C32—O7—C36118.0 (2)
C6—C1—C2—C30.3 (3)O6—Co1—N1—C7−117.02 (18)
N2—C1—C2—C3178.1 (2)O3—Co1—N1—C711.1 (2)
C1—C2—C3—C4−0.1 (4)N4i—Co1—N1—C7141.80 (17)
C2—C3—C4—C5−0.1 (4)O2—Co1—N1—C751.62 (18)
C3—C4—C5—C60.2 (4)O6—Co1—N1—C664.75 (17)
C2—C1—C6—C5−0.2 (3)O3—Co1—N1—C6−167.17 (14)
N2—C1—C6—C5−178.51 (18)N4i—Co1—N1—C6−36.44 (17)
C2—C1—C6—N1178.64 (18)O2—Co1—N1—C6−126.61 (16)
N2—C1—C6—N10.3 (2)N1—C7—N2—C1−0.2 (2)
C4—C5—C6—C10.0 (3)C8—C7—N2—C1177.53 (19)
C4—C5—C6—N1−178.6 (2)N1—C7—N2—C9175.86 (18)
N2—C9—C10—O163.5 (3)C8—C7—N2—C9−6.4 (3)
O1—C11—C12—N3−60.1 (3)C6—C1—N2—C7−0.1 (2)
N3—C13—C14—C15179.9 (2)C2—C1—N2—C7−178.2 (2)
C18—C13—C14—C150.1 (4)C6—C1—N2—C9−176.30 (18)
C13—C14—C15—C160.0 (4)C2—C1—N2—C95.6 (3)
C14—C15—C16—C170.2 (4)C10—C9—N2—C7−98.9 (3)
C15—C16—C17—C18−0.4 (4)C10—C9—N2—C176.4 (3)
N3—C13—C18—C17179.77 (19)N4—C19—N3—C13−1.5 (3)
C14—C13—C18—C17−0.4 (3)C20—C19—N3—C13178.7 (2)
N3—C13—C18—N4−1.2 (2)N4—C19—N3—C12−172.9 (2)
C14—C13—C18—N4178.6 (2)C20—C19—N3—C127.3 (4)
C16—C17—C18—C130.6 (3)C18—C13—N3—C191.6 (2)
C16—C17—C18—N4−178.3 (2)C14—C13—N3—C19−178.2 (3)
C26—C21—C22—C230.3 (4)C18—C13—N3—C12173.2 (2)
C27—C21—C22—C23−179.3 (2)C14—C13—N3—C12−6.6 (4)
C21—C22—C23—C240.4 (4)C11—C12—N3—C1993.8 (3)
C22—C23—C24—O4178.2 (2)C11—C12—N3—C13−76.3 (3)
C22—C23—C24—C25−1.0 (4)N3—C19—N4—C180.8 (2)
O4—C24—C25—C26−178.3 (2)C20—C19—N4—C18−179.5 (2)
C23—C24—C25—C260.9 (4)N3—C19—N4—Co1i−177.77 (14)
C24—C25—C26—C21−0.2 (4)C20—C19—N4—Co1i2.0 (3)
C22—C21—C26—C25−0.4 (4)C13—C18—N4—C190.3 (2)
C27—C21—C26—C25179.2 (2)C17—C18—N4—C19179.2 (2)
C26—C21—C27—O23.5 (4)C13—C18—N4—Co1i178.91 (14)
C22—C21—C27—O2−176.9 (3)C17—C18—N4—Co1i−2.2 (3)
C26—C21—C27—O3−174.3 (2)C9—C10—O1—C1188.7 (2)
C22—C21—C27—O35.3 (4)C12—C11—O1—C10178.01 (19)
C34—C29—C30—C312.5 (3)O3—C27—O2—Co14.4 (3)
C35—C29—C30—C31−175.5 (2)C21—C27—O2—Co1−173.3 (2)
C29—C30—C31—C32−1.4 (3)O6—Co1—O2—C27−16.1 (4)
C30—C31—C32—O7177.8 (2)O3—Co1—O2—C27−2.70 (17)
C30—C31—C32—C33−1.6 (3)N1—Co1—O2—C27−150.41 (18)
O7—C32—C33—C34−176.2 (2)N4i—Co1—O2—C27104.81 (18)
C31—C32—C33—C343.3 (4)O2—C27—O3—Co1−5.1 (3)
C32—C33—C34—C29−2.1 (4)C21—C27—O3—Co1172.6 (2)
C30—C29—C34—C33−0.8 (3)O6—Co1—O3—C27178.96 (17)
C35—C29—C34—C33177.2 (2)N1—Co1—O3—C2752.5 (2)
C30—C29—C35—O5−6.7 (3)N4i—Co1—O3—C27−78.15 (18)
C34—C29—C35—O5175.4 (2)O2—Co1—O3—C272.69 (17)
C30—C29—C35—O6172.9 (2)C25—C24—O4—C28−6.1 (3)
C34—C29—C35—O6−5.0 (3)C23—C24—O4—C28174.7 (2)
N2—C7—N1—C60.4 (2)O5—C35—O6—Co111.7 (3)
C8—C7—N1—C6−177.3 (2)C29—C35—O6—Co1−167.95 (14)
N2—C7—N1—Co1−178.13 (13)O3—Co1—O6—C35−84.34 (17)
C8—C7—N1—Co14.2 (3)N1—Co1—O6—C3560.66 (17)
C1—C6—N1—C7−0.4 (2)N4i—Co1—O6—C35167.49 (16)
C5—C6—N1—C7178.3 (2)O2—Co1—O6—C35−72.5 (3)
C1—C6—N1—Co1178.14 (13)C31—C32—O7—C36−25.7 (3)
C5—C6—N1—Co1−3.2 (3)C33—C32—O7—C36153.7 (2)

Symmetry codes: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C17—H015···O6i0.932.463.111 (3)127
C8—H8C···O20.962.503.255 (3)136
C20—H03B···O2i0.962.423.150 (3)132

Symmetry codes: (i) −x+1, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5721).

References

  • Dimitrou, K., Brown, A.-D., Folting, K. & Christou, G. (1999). Inorg. Chem.46, 7253–7255.
  • Hoskins, B. F., Robson, R. & Slizys, D. A. (1997). J. Am. Chem. Soc.119, 2952–2953.
  • Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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