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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): m1196–m1197.
Published online 2009 September 12. doi:  10.1107/S1600536809035934
PMCID: PMC2970309

Bis[bis­(1-ethyl­benzimidazol-2-ylmeth­yl) ether]cobalt(II) dipicrate dimethyl­formamide disolvate

Abstract

In the title complex, [Co(C20H22N4O)2](C6H2N3O7)2·2C3H7NO, the CoII ion is coordinated by two sets of two N atoms and an O atom from two independent tridendate ligands in a distorted octa­hedral coordination environment. There are significant differences between chemically equivalent coordination bond lengths. The crystal structure is stabilized by weak inter­molecular C—H(...)O hydrogen bonds and weak π–π stacking inter­actions [centroid–centroid distance 3.495 (1) Å]. In one of the anions one nitro group is rotationally disordered about the C—N bond with refined occupancies of 0.524 (8) and 0.476 (8).

Related literature

For related structures, see: Wu, Yun, Huang et al. (2009 [triangle]); Wu, Yun, Li et al. (2009 [triangle]); Yun et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1196-scheme1.jpg

Experimental

Crystal data

  • [Co(C20H22N4O)2](C6H2N3O7)2·2C3H7NO
  • M r = 1330.17
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1196-efi1.jpg
  • a = 13.8799 (4) Å
  • b = 14.6525 (4) Å
  • c = 16.5701 (3) Å
  • α = 110.664 (1)°
  • β = 96.470 (1)°
  • γ = 99.612 (1)°
  • V = 3054.62 (13) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.37 mm−1
  • T = 153 K
  • 0.38 × 0.22 × 0.14 mm

Data collection

  • Rigaku R-AXIS Spider diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.873, T max = 0.950
  • 24337 measured reflections
  • 11225 independent reflections
  • 8833 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.136
  • S = 1.14
  • 11225 reflections
  • 858 parameters
  • 4 restraints
  • H-atom parameters constrained
  • Δρmax = 0.98 e Å−3
  • Δρmin = −0.90 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL.

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035934/lh2889sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035934/lh2889Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support and a grant from the ‘Qing Lan’ Talent Engineering Funds and the Students’ Science and Technology Innovation Funds (grant No. DXS2008–041) of Lanzhou Jiaotong University. A grant from the ‘Long Yuan Qing Nian’ of Gansu Province also is acknowledged.

supplementary crystallographic information

Comment

Interest in bis(2-benzimidazolyl)alkanes and their derivatives are widespread and we have previously reported the crystal structure of some related complexes (Wu, Yun, Huang et al., 2009; Wu, Yun, Li et al., 2009; Yun et al., 2008). The asymmetric unit of the title compound consists of a di[1,3-bis(1-ethylbenzimidazol-2-yl)-2-oxopropane] cobalt(II) cation (Fig. 1), two picrate anions and two molecules of DMF. The CoII ion is six-coordinated with a N4O2 ligand set. The Etobb (1,3-bis(1-ethylbenzimidazol-2-yl)-2-oxopropane) ligand acts as a tridentate donor. The four N atoms are not in an ideal equatorial plane and the coordination geometry of the CoII may be best described as distorted octahedral. There are significant differnces between chemically equivalent coordination bond lengths. The crystal structure is stabilized by weak intermolecular C—H···O hydrogen bond interactions and weak π···π stacking interactions (Fig. 2) with centroid to centroid distances of 3.495 (1)Å between inversion related benzimidazole rings systems.

Experimental

To a stirred solution of 1,3-bis(1-ethylbenzimidazol-2-yl)-2-oxopropane (0.167 g, 0.5 mmol) in hot MeOH (15 ml) was added Co(C6H2N3O7)2 (0.129 g, 0.25 mmol) in MeOH (5 ml). A brown crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH and absolute Et2O, and dried in vacuo. The dried precipitate was dissolved in DMF resulting in a brown solution. Brown crystals suitable for X-ray diffraction studies were obtained after three days at room temperature from ether diffusion into a DMF solution of the title compound. Yield, 0.210 g (71%). (found: C, 52.41; H, 4.68; N, 16.81. Calcd. for C116H124Co2N32O36: C, 52.37; H, 4.70; N, 16.85)

Refinement

All H atoms were found in difference electron maps and were subsequently refined in a riding-model approximation with C—H distances ranging from 0.95 to 0.99 Å and Uiso(H) = 1.2 Ueq or Uiso(H) = 1.5Ueq of the carrier atom, respectively. In one of the anions one nitro group is rotationally disordered about the C-N bond with refined occupancies of 0.524 (8) [O8,O9] and 0.476 (8) [O8',O9'].

Figures

Fig. 1.
Molecular structure and atom numbering for the cation of the title compound. Hydrogen atoms have been omitted for clarity and the displacement ellipsoids are shown at the 30% probability level.
Fig. 2.
Part of the crystal structure showing weak C—H···O hydrogen bonds (dashed lines) and weak π···π stacking interactions. Only H atoms involved in hydrogen bonds are shown. The disorder ...

Crystal data

[Co(C20H22N4O)2](C6H2N3O7)2·2C3H7NOZ = 2
Mr = 1330.17F(000) = 1386
Triclinic, P1Dx = 1.446 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.8799 (4) ÅCell parameters from 7749 reflections
b = 14.6525 (4) Åθ = 3.0–25.5°
c = 16.5701 (3) ŵ = 0.37 mm1
α = 110.664 (1)°T = 153 K
β = 96.470 (1)°Block, brown
γ = 99.612 (1)°0.38 × 0.22 × 0.14 mm
V = 3054.62 (13) Å3

Data collection

Rigaku R-AXIS Spider diffractometer11225 independent reflections
Radiation source: fine-focus sealed tube8833 reflections with I > 2σ(I)
graphiteRint = 0.022
[var phi] and ω scansθmax = 25.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −16→16
Tmin = 0.873, Tmax = 0.950k = −17→17
24337 measured reflectionsl = −18→20

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.136w = 1/[σ2(Fo2) + (0.0663P)2 + 2.0559P] where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.10
11225 reflectionsΔρmax = 0.98 e Å3
858 parametersΔρmin = −0.89 e Å3
4 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0022 (5)

Special details

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)

xyzUiso*/UeqOcc. (<1)
Co0.28649 (2)0.19838 (2)0.46816 (2)0.01823 (11)
O10.29902 (13)0.30499 (13)0.61018 (11)0.0234 (4)
O20.29752 (13)0.08087 (14)0.34517 (11)0.0278 (4)
O30.80117 (19)0.5715 (2)0.13764 (15)0.0629 (7)
O40.5964 (3)0.3781 (2)0.17574 (16)0.0752 (10)
O50.7548 (3)0.4037 (3)0.1790 (2)0.0980 (12)
O60.41385 (18)0.2944 (2)−0.11930 (18)0.0619 (7)
O70.45343 (19)0.3970 (2)−0.18404 (14)0.0559 (7)
O80.7909 (5)0.6140 (5)−0.0805 (3)0.082 (3)0.524 (8)
O90.8201 (4)0.6944 (5)0.0537 (4)0.064 (2)0.524 (8)
O8'0.7091 (5)0.6837 (5)−0.0389 (4)0.089 (3)0.476 (8)
O9'0.8490 (4)0.6593 (10)0.0175 (9)0.116 (4)0.476 (8)
O100.67849 (16)0.05378 (17)−0.11405 (13)0.0406 (5)
O110.54090 (17)0.13588 (18)−0.18370 (13)0.0434 (5)
O120.40246 (16)0.06268 (18)−0.16289 (14)0.0443 (5)
O130.39642 (17)0.17501 (17)0.15142 (14)0.0442 (5)
O140.52461 (17)0.17492 (16)0.23989 (12)0.0407 (5)
O150.80210 (18)0.0547 (2)0.11187 (18)0.0587 (7)
O160.84422 (16)0.1175 (2)0.01821 (15)0.0518 (6)
O170.10881 (18)0.8163 (2)0.20909 (15)0.0575 (7)
O180.07622 (17)0.40600 (18)0.63580 (14)0.0473 (6)
N10.20049 (14)0.12155 (16)0.52909 (12)0.0197 (4)
N20.14353 (15)0.10419 (16)0.64503 (13)0.0223 (5)
N30.33896 (15)0.34492 (15)0.47641 (13)0.0200 (4)
N40.36761 (15)0.51053 (15)0.54120 (13)0.0209 (4)
N50.16690 (15)0.19040 (16)0.36748 (13)0.0206 (4)
N60.09391 (16)0.13339 (17)0.22634 (13)0.0248 (5)
N70.42207 (15)0.15693 (15)0.49147 (12)0.0196 (4)
N80.54212 (16)0.07996 (16)0.44281 (13)0.0235 (5)
N90.6710 (3)0.4043 (2)0.14874 (18)0.0558 (9)
N100.4692 (2)0.3651 (2)−0.12503 (18)0.0426 (7)
N110.7593 (3)0.6329 (3)−0.01009 (19)0.0867 (15)
N120.49148 (18)0.10217 (18)−0.13969 (14)0.0321 (5)
N130.48254 (19)0.16547 (18)0.16615 (15)0.0327 (6)
N140.78255 (18)0.0908 (2)0.05747 (16)0.0370 (6)
N150.1137 (2)0.7045 (3)0.07460 (19)0.0623 (9)
N16−0.0601 (2)0.4302 (2)0.69697 (17)0.0453 (7)
C10.14755 (17)0.02311 (19)0.50421 (16)0.0202 (5)
C20.12581 (18)−0.0567 (2)0.42273 (16)0.0237 (5)
H2A0.1477−0.04910.37270.028*
C30.07159 (19)−0.1465 (2)0.41792 (18)0.0278 (6)
H3A0.0565−0.20200.36350.033*
C40.0378 (2)−0.1586 (2)0.49117 (18)0.0289 (6)
H4A0.0010−0.22220.48530.035*
C50.05712 (19)−0.0795 (2)0.57183 (18)0.0282 (6)
H5A0.0339−0.08690.62140.034*
C60.11200 (18)0.01088 (19)0.57638 (16)0.0220 (5)
C70.19536 (17)0.16562 (19)0.61295 (15)0.0194 (5)
C80.24117 (19)0.27325 (19)0.66549 (15)0.0224 (5)
H8A0.18930.31220.67990.027*
H8B0.28380.28150.72080.027*
C90.3238 (2)0.40958 (18)0.63268 (15)0.0229 (5)
H9A0.38300.44120.68020.028*
H9B0.26770.44000.65230.028*
C100.34504 (17)0.42222 (19)0.55015 (15)0.0206 (5)
C110.37509 (18)0.48952 (19)0.45373 (16)0.0223 (5)
C120.3948 (2)0.5512 (2)0.40767 (18)0.0291 (6)
H12A0.40700.62200.43510.035*
C130.3958 (2)0.5032 (2)0.31901 (18)0.0346 (7)
H13A0.40870.54250.28480.041*
C140.3782 (2)0.3990 (2)0.27845 (18)0.0315 (6)
H14A0.37960.36930.21770.038*
C150.3590 (2)0.3387 (2)0.32506 (17)0.0271 (6)
H15A0.34750.26790.29770.033*
C160.35722 (18)0.38544 (19)0.41382 (16)0.0221 (5)
C170.1169 (2)0.1340 (2)0.73351 (17)0.0282 (6)
H17A0.04460.10880.72740.034*
H17B0.13120.20790.76120.034*
C180.1725 (3)0.0947 (3)0.7923 (2)0.0495 (9)
H18A0.15220.11630.84970.074*
H18B0.24410.12070.79980.074*
H18C0.15760.02150.76590.074*
C190.3731 (2)0.60909 (19)0.60915 (16)0.0263 (6)
H19A0.42010.66040.59840.032*
H19B0.39910.60910.66730.032*
C200.2727 (2)0.6357 (2)0.6101 (2)0.0423 (8)
H20A0.27910.70160.65630.063*
H20B0.22620.58550.62150.063*
H20C0.24750.63740.55310.063*
C210.09872 (18)0.24717 (19)0.35843 (15)0.0217 (5)
C220.0729 (2)0.3280 (2)0.42065 (17)0.0274 (6)
H22A0.10390.35350.48070.033*
C230.0009 (2)0.3692 (2)0.39152 (19)0.0341 (7)
H23A−0.01830.42370.43260.041*
C24−0.0450 (2)0.3330 (2)0.30304 (19)0.0363 (7)
H24A−0.09440.36360.28570.044*
C25−0.0199 (2)0.2536 (2)0.24042 (19)0.0332 (6)
H25A−0.05030.22890.18020.040*
C260.05232 (19)0.2121 (2)0.27061 (16)0.0251 (6)
C270.16210 (18)0.12508 (19)0.28700 (15)0.0221 (5)
C280.22980 (19)0.0551 (2)0.26444 (16)0.0259 (6)
H28A0.1923−0.01530.24320.031*
H28B0.26580.06420.21860.031*
C290.38727 (18)0.0477 (2)0.33422 (16)0.0233 (5)
H29A0.41910.06950.29160.028*
H29B0.3748−0.02610.31340.028*
C300.45091 (18)0.09541 (18)0.42356 (15)0.0195 (5)
C310.57725 (19)0.13738 (19)0.53148 (16)0.0233 (5)
C320.6663 (2)0.1502 (2)0.58537 (18)0.0298 (6)
H32A0.71740.11830.56330.036*
C330.6775 (2)0.2111 (2)0.67244 (18)0.0306 (6)
H33A0.73760.22190.71150.037*
C340.6014 (2)0.2577 (2)0.70433 (17)0.0286 (6)
H34A0.61130.29920.76470.034*
C350.51260 (19)0.2449 (2)0.65041 (16)0.0251 (6)
H35A0.46120.27600.67270.030*
C360.50137 (18)0.18448 (19)0.56205 (15)0.0204 (5)
C370.0750 (2)0.0776 (2)0.13075 (16)0.0333 (7)
H37A0.00280.06250.10760.040*
H37B0.09570.01330.11820.040*
C380.1305 (3)0.1359 (3)0.0843 (2)0.0502 (9)
H38A0.11630.09630.02110.075*
H38B0.20210.15010.10650.075*
H38C0.10900.19890.09540.075*
C390.6008 (2)0.0221 (2)0.38379 (17)0.0279 (6)
H39A0.5560−0.02550.32890.033*
H39B0.6329−0.01730.41210.033*
C400.6796 (2)0.0891 (2)0.36196 (19)0.0363 (7)
H40A0.71710.04820.32260.055*
H40B0.72490.13530.41610.055*
H40C0.64790.12730.33300.055*
C410.7297 (2)0.5228 (2)0.07784 (18)0.0378 (7)
C420.6578 (2)0.4375 (2)0.07595 (17)0.0350 (7)
C430.5747 (2)0.3879 (2)0.01257 (18)0.0330 (6)
H43A0.52910.33480.01730.040*
C440.5576 (2)0.4155 (2)−0.05849 (17)0.0310 (6)
C450.6213 (2)0.4953 (2)−0.06346 (17)0.0367 (7)
H45A0.60870.5148−0.11180.044*
C460.7027 (2)0.5462 (2)0.00134 (19)0.0388 (7)
C470.6395 (2)0.0877 (2)−0.04959 (17)0.0278 (6)
C480.5411 (2)0.1095 (2)−0.05470 (16)0.0265 (6)
C490.4898 (2)0.1320 (2)0.01257 (16)0.0264 (6)
H49A0.42400.14130.00340.032*
C500.5358 (2)0.1411 (2)0.09506 (16)0.0261 (6)
C510.6320 (2)0.1276 (2)0.10885 (17)0.0293 (6)
H51A0.66290.13420.16540.035*
C520.6820 (2)0.1045 (2)0.04027 (17)0.0286 (6)
C530.0698 (3)0.7568 (4)0.1365 (3)0.0910 (19)
H53−0.00040.74630.12220.109*
C540.2175 (3)0.7168 (3)0.0886 (2)0.0534 (9)
H54A0.24600.76190.14930.080*
H54B0.24470.74540.04840.080*
H54C0.23440.65170.07770.080*
C550.0620 (4)0.6385 (6)−0.0135 (4)0.162 (4)
H55A−0.00960.6347−0.01750.242*
H55B0.07490.5715−0.02620.242*
H55C0.08600.6648−0.05610.242*
C560.0356 (2)0.4296 (2)0.6990 (2)0.0416 (8)
H56A0.07620.44950.75510.050*
C57−0.1274 (3)0.4030 (3)0.6141 (2)0.0497 (8)
H57A−0.09140.38200.56560.075*
H57B−0.15380.46080.61360.075*
H57C−0.18250.34780.60740.075*
C58−0.1011 (4)0.4648 (4)0.7763 (3)0.099 (2)
H58A−0.04930.48050.82750.149*
H58B−0.15620.41230.77460.149*
H58C−0.12550.52500.78030.149*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co0.01811 (18)0.0209 (2)0.01589 (17)0.00583 (13)0.00398 (12)0.00627 (13)
O10.0314 (10)0.0197 (9)0.0205 (9)0.0050 (8)0.0116 (7)0.0075 (7)
O20.0226 (10)0.0405 (12)0.0179 (9)0.0166 (8)0.0030 (7)0.0040 (8)
O30.0526 (16)0.0693 (18)0.0400 (13)−0.0042 (13)−0.0136 (11)0.0035 (12)
O40.139 (3)0.0478 (16)0.0359 (14)0.0037 (17)0.0277 (16)0.0170 (12)
O50.126 (3)0.106 (3)0.068 (2)0.041 (2)−0.024 (2)0.0462 (19)
O60.0374 (14)0.0474 (16)0.0740 (18)0.0025 (12)−0.0019 (12)−0.0022 (13)
O70.0561 (16)0.0713 (18)0.0288 (12)0.0351 (14)−0.0065 (10)0.0000 (11)
O80.089 (5)0.081 (5)0.070 (4)−0.009 (4)0.038 (3)0.028 (3)
O90.033 (3)0.051 (4)0.093 (5)−0.008 (3)0.000 (3)0.020 (3)
O8'0.115 (6)0.078 (5)0.076 (5)−0.031 (4)−0.014 (4)0.065 (4)
O9'0.072 (6)0.120 (10)0.160 (11)−0.004 (6)0.033 (6)0.066 (8)
O100.0462 (13)0.0484 (14)0.0297 (11)0.0229 (11)0.0162 (9)0.0094 (9)
O110.0488 (13)0.0599 (15)0.0291 (11)0.0127 (11)0.0105 (9)0.0248 (10)
O120.0330 (13)0.0553 (15)0.0398 (12)0.0022 (11)−0.0048 (9)0.0194 (10)
O130.0399 (13)0.0526 (15)0.0425 (12)0.0184 (11)0.0209 (10)0.0132 (10)
O140.0554 (14)0.0444 (13)0.0219 (10)0.0091 (11)0.0129 (9)0.0113 (9)
O150.0397 (14)0.085 (2)0.0775 (18)0.0222 (13)0.0072 (12)0.0592 (16)
O160.0307 (12)0.0788 (19)0.0536 (14)0.0140 (12)0.0156 (10)0.0312 (13)
O170.0457 (14)0.0662 (17)0.0402 (13)0.0142 (13)0.0072 (11)−0.0046 (12)
O180.0415 (13)0.0523 (15)0.0379 (12)0.0189 (11)0.0043 (10)0.0022 (10)
N10.0158 (10)0.0250 (12)0.0176 (10)0.0064 (9)0.0028 (8)0.0065 (8)
N20.0191 (11)0.0300 (12)0.0197 (10)0.0054 (9)0.0062 (8)0.0110 (9)
N30.0202 (11)0.0198 (11)0.0194 (10)0.0015 (9)0.0039 (8)0.0079 (8)
N40.0234 (11)0.0159 (11)0.0222 (11)0.0032 (9)0.0038 (8)0.0063 (8)
N50.0191 (11)0.0229 (11)0.0190 (10)0.0051 (9)0.0044 (8)0.0065 (8)
N60.0232 (11)0.0322 (13)0.0166 (10)0.0101 (10)0.0012 (8)0.0056 (9)
N70.0190 (11)0.0223 (11)0.0180 (10)0.0060 (9)0.0046 (8)0.0072 (8)
N80.0220 (11)0.0263 (12)0.0229 (11)0.0103 (9)0.0046 (8)0.0078 (9)
N90.099 (3)0.0392 (17)0.0260 (14)0.0201 (17)0.0034 (16)0.0089 (12)
N100.0321 (15)0.0375 (16)0.0414 (16)0.0165 (13)0.0017 (11)−0.0074 (12)
N110.117 (4)0.079 (3)0.0377 (19)−0.042 (3)0.007 (2)0.0219 (18)
N120.0365 (14)0.0349 (14)0.0244 (12)0.0123 (11)0.0051 (10)0.0090 (10)
N130.0414 (15)0.0270 (13)0.0284 (13)0.0057 (11)0.0148 (11)0.0073 (10)
N140.0309 (14)0.0438 (16)0.0405 (14)0.0118 (12)0.0058 (11)0.0196 (12)
N150.0422 (17)0.064 (2)0.0459 (17)0.0149 (15)−0.0057 (13)−0.0179 (15)
N160.0410 (16)0.0472 (17)0.0354 (14)0.0045 (13)0.0070 (11)0.0037 (12)
C10.0131 (12)0.0231 (13)0.0263 (13)0.0063 (10)0.0029 (9)0.0110 (10)
C20.0159 (12)0.0313 (15)0.0234 (13)0.0079 (11)0.0034 (9)0.0087 (11)
C30.0222 (14)0.0249 (14)0.0318 (14)0.0080 (11)−0.0003 (10)0.0058 (11)
C40.0234 (14)0.0220 (14)0.0408 (16)0.0025 (11)0.0024 (11)0.0138 (12)
C50.0218 (14)0.0323 (16)0.0366 (15)0.0064 (12)0.0060 (11)0.0201 (12)
C60.0149 (12)0.0261 (14)0.0252 (13)0.0055 (10)0.0025 (9)0.0101 (10)
C70.0170 (12)0.0238 (13)0.0188 (12)0.0070 (10)0.0038 (9)0.0087 (10)
C80.0245 (13)0.0247 (14)0.0165 (12)0.0032 (11)0.0068 (9)0.0062 (10)
C90.0290 (14)0.0168 (13)0.0199 (12)0.0037 (11)0.0040 (10)0.0039 (10)
C100.0159 (12)0.0248 (14)0.0191 (12)0.0043 (10)0.0015 (9)0.0064 (10)
C110.0185 (13)0.0221 (13)0.0259 (13)0.0027 (10)0.0049 (10)0.0091 (10)
C120.0330 (15)0.0230 (14)0.0337 (15)0.0056 (12)0.0082 (11)0.0133 (11)
C130.0389 (17)0.0405 (18)0.0329 (15)0.0069 (14)0.0124 (12)0.0232 (13)
C140.0387 (16)0.0347 (16)0.0241 (13)0.0079 (13)0.0123 (11)0.0129 (12)
C150.0302 (15)0.0257 (14)0.0254 (13)0.0073 (12)0.0091 (11)0.0078 (11)
C160.0176 (12)0.0256 (14)0.0242 (13)0.0049 (10)0.0051 (9)0.0105 (10)
C170.0264 (14)0.0394 (17)0.0244 (13)0.0104 (12)0.0111 (11)0.0155 (12)
C180.059 (2)0.073 (3)0.0339 (17)0.0341 (19)0.0170 (15)0.0302 (17)
C190.0324 (15)0.0192 (14)0.0239 (13)0.0041 (11)0.0059 (11)0.0048 (10)
C200.0413 (18)0.0342 (18)0.0475 (18)0.0171 (15)0.0096 (14)0.0067 (14)
C210.0180 (12)0.0268 (14)0.0215 (12)0.0044 (11)0.0053 (9)0.0104 (10)
C220.0272 (14)0.0306 (15)0.0255 (13)0.0092 (12)0.0083 (10)0.0096 (11)
C230.0337 (16)0.0365 (17)0.0357 (16)0.0163 (13)0.0127 (12)0.0124 (13)
C240.0321 (16)0.0439 (19)0.0404 (16)0.0198 (14)0.0075 (12)0.0196 (14)
C250.0275 (15)0.0430 (18)0.0307 (15)0.0145 (13)0.0017 (11)0.0140 (13)
C260.0232 (14)0.0293 (15)0.0224 (13)0.0070 (11)0.0046 (10)0.0085 (11)
C270.0183 (12)0.0264 (14)0.0183 (12)0.0038 (10)0.0024 (9)0.0055 (10)
C280.0236 (14)0.0328 (15)0.0163 (12)0.0096 (11)−0.0005 (10)0.0033 (10)
C290.0220 (13)0.0281 (14)0.0211 (12)0.0108 (11)0.0077 (10)0.0076 (10)
C300.0198 (13)0.0173 (13)0.0239 (12)0.0048 (10)0.0066 (10)0.0099 (10)
C310.0223 (13)0.0234 (14)0.0242 (13)0.0047 (11)0.0032 (10)0.0095 (10)
C320.0245 (14)0.0348 (16)0.0336 (15)0.0129 (12)0.0049 (11)0.0145 (12)
C330.0266 (15)0.0321 (16)0.0307 (14)0.0058 (12)−0.0032 (11)0.0117 (12)
C340.0317 (15)0.0285 (15)0.0234 (13)0.0062 (12)0.0012 (11)0.0085 (11)
C350.0249 (14)0.0286 (15)0.0239 (13)0.0071 (11)0.0067 (10)0.0113 (11)
C360.0202 (13)0.0205 (13)0.0215 (12)0.0032 (10)0.0031 (9)0.0100 (10)
C370.0302 (15)0.0452 (18)0.0164 (13)0.0120 (13)−0.0031 (10)0.0028 (12)
C380.053 (2)0.070 (3)0.0279 (16)0.0150 (18)0.0104 (14)0.0173 (16)
C390.0272 (14)0.0299 (15)0.0280 (14)0.0170 (12)0.0071 (11)0.0072 (11)
C400.0296 (16)0.0451 (19)0.0368 (16)0.0135 (14)0.0137 (12)0.0138 (13)
C410.0352 (17)0.0419 (18)0.0256 (14)0.0057 (14)0.0027 (12)0.0023 (12)
C420.0490 (19)0.0379 (17)0.0203 (13)0.0196 (14)0.0074 (12)0.0088 (12)
C430.0399 (17)0.0237 (15)0.0342 (15)0.0115 (13)0.0138 (12)0.0055 (12)
C440.0299 (15)0.0321 (16)0.0232 (13)0.0129 (13)0.0006 (11)−0.0004 (11)
C450.0517 (19)0.0356 (17)0.0189 (13)0.0081 (14)0.0042 (12)0.0072 (12)
C460.0436 (18)0.0348 (17)0.0306 (15)−0.0025 (14)0.0094 (13)0.0080 (13)
C470.0317 (15)0.0265 (15)0.0263 (14)0.0110 (12)0.0095 (11)0.0081 (11)
C480.0317 (15)0.0258 (14)0.0204 (13)0.0075 (12)0.0028 (10)0.0071 (10)
C490.0273 (14)0.0262 (14)0.0262 (13)0.0082 (11)0.0066 (11)0.0092 (11)
C500.0329 (15)0.0262 (14)0.0214 (13)0.0085 (12)0.0095 (11)0.0094 (10)
C510.0329 (15)0.0313 (16)0.0229 (13)0.0052 (12)0.0039 (11)0.0105 (11)
C520.0257 (14)0.0303 (15)0.0301 (14)0.0084 (12)0.0052 (11)0.0108 (11)
C530.040 (2)0.113 (4)0.067 (3)0.030 (2)−0.0079 (19)−0.030 (3)
C540.053 (2)0.057 (2)0.0446 (19)0.0150 (18)0.0175 (16)0.0084 (16)
C550.083 (4)0.187 (7)0.093 (4)0.039 (4)−0.027 (3)−0.082 (4)
C560.046 (2)0.0370 (18)0.0321 (16)0.0078 (15)−0.0047 (14)0.0058 (13)
C570.0376 (19)0.052 (2)0.059 (2)0.0071 (16)−0.0016 (15)0.0237 (17)
C580.071 (3)0.108 (4)0.066 (3)−0.019 (3)0.036 (2)−0.018 (3)

Geometric parameters (Å, °)

Co—N12.083 (2)C13—H13A0.9500
Co—N32.099 (2)C14—C151.378 (4)
Co—N72.108 (2)C14—H14A0.9500
Co—N52.174 (2)C15—C161.391 (4)
Co—O22.1961 (17)C15—H15A0.9500
Co—O12.2872 (16)C17—C181.501 (4)
O1—C91.413 (3)C17—H17A0.9900
O1—C81.429 (3)C17—H17B0.9900
O2—C291.419 (3)C18—H18A0.9800
O2—C281.434 (3)C18—H18B0.9800
O3—C411.232 (4)C18—H18C0.9800
O4—N91.230 (4)C19—C201.510 (4)
O5—N91.217 (5)C19—H19A0.9900
O6—N101.222 (4)C19—H19B0.9900
O7—N101.237 (4)C20—H20A0.9800
O8—N111.249 (3)C20—H20B0.9800
O9—N111.230 (3)C20—H20C0.9800
O8'—N111.271 (3)C21—C261.395 (3)
O9'—N111.223 (3)C21—C221.399 (4)
O10—C471.236 (3)C22—C231.376 (4)
O11—N121.225 (3)C22—H22A0.9500
O12—N121.227 (3)C23—C241.402 (4)
O13—O130.000 (5)C23—H23A0.9500
O13—N131.234 (3)C24—C251.384 (4)
O14—O140.000 (5)C24—H24A0.9500
O14—N131.243 (3)C25—C261.389 (4)
O15—N141.223 (3)C25—H25A0.9500
O16—N141.226 (3)C27—C281.485 (4)
O17—C531.206 (4)C28—H28A0.9900
O18—C561.216 (4)C28—H28B0.9900
N1—C71.326 (3)C29—C301.493 (3)
N1—C11.396 (3)C29—H29A0.9900
N2—C71.348 (3)C29—H29B0.9900
N2—C61.395 (3)C31—C321.384 (4)
N2—C171.484 (3)C31—C361.399 (4)
N3—C101.323 (3)C32—C331.378 (4)
N3—C161.391 (3)C32—H32A0.9500
N4—C101.343 (3)C33—C341.404 (4)
N4—C111.391 (3)C33—H33A0.9500
N4—C191.468 (3)C34—C351.382 (4)
N5—C271.325 (3)C34—H34A0.9500
N5—C211.389 (3)C35—C361.392 (3)
N6—C271.353 (3)C35—H35A0.9500
N6—C261.387 (3)C37—C381.513 (4)
N6—C371.472 (3)C37—H37A0.9900
N7—C301.321 (3)C37—H37B0.9900
N7—C361.404 (3)C38—H38A0.9800
N8—C301.346 (3)C38—H38B0.9800
N8—C311.391 (3)C38—H38C0.9800
N8—C391.472 (3)C39—C401.507 (4)
N9—C421.455 (4)C39—H39A0.9900
N10—C441.444 (4)C39—H39B0.9900
N11—C461.463 (4)C40—H40A0.9800
N12—C481.456 (3)C40—H40B0.9800
N13—O131.234 (3)C40—H40C0.9800
N13—O141.243 (3)C41—C461.452 (4)
N13—C501.432 (3)C41—C421.452 (4)
N14—C521.454 (4)C42—C431.367 (4)
N15—C531.324 (5)C43—C441.383 (4)
N15—C541.405 (5)C43—H43A0.9500
N15—C551.455 (5)C44—C451.375 (4)
N16—C561.327 (4)C45—C461.366 (4)
N16—C581.450 (5)C45—H45A0.9500
N16—C571.455 (4)C47—C481.453 (4)
C1—C21.400 (4)C47—C521.456 (4)
C1—C61.400 (3)C48—C491.362 (4)
C2—C31.372 (4)C49—C501.393 (4)
C2—H2A0.9500C49—H49A0.9500
C3—C41.407 (4)C50—C511.388 (4)
C3—H3A0.9500C51—C521.368 (4)
C4—C51.387 (4)C51—H51A0.9500
C4—H4A0.9500C53—H530.9500
C5—C61.386 (4)C54—H54A0.9800
C5—H5A0.9500C54—H54B0.9800
C7—C81.490 (3)C54—H54C0.9800
C8—H8A0.9900C55—H55A0.9800
C8—H8B0.9900C55—H55B0.9800
C9—C101.498 (3)C55—H55C0.9800
C9—H9A0.9900C56—H56A0.9500
C9—H9B0.9900C57—H57A0.9800
C11—C121.388 (4)C57—H57B0.9800
C11—C161.396 (4)C57—H57C0.9800
C12—C131.390 (4)C58—H58A0.9800
C12—H12A0.9500C58—H58B0.9800
C13—C141.399 (4)C58—H58C0.9800
N1—Co—N3140.20 (8)N4—C19—H19B109.3
N1—Co—N799.60 (8)C20—C19—H19B109.3
N3—Co—N7100.49 (8)H19A—C19—H19B107.9
N1—Co—N597.14 (8)C19—C20—H20A109.5
N3—Co—N585.56 (8)C19—C20—H20B109.5
N7—Co—N5144.80 (7)H20A—C20—H20B109.5
N1—Co—O2103.97 (8)C19—C20—H20C109.5
N3—Co—O2114.58 (7)H20A—C20—H20C109.5
N7—Co—O273.35 (7)H20B—C20—H20C109.5
N5—Co—O272.66 (7)N5—C21—C26109.4 (2)
N1—Co—O172.54 (7)N5—C21—C22130.8 (2)
N3—Co—O171.85 (7)C26—C21—C22119.8 (2)
N7—Co—O194.77 (7)C23—C22—C21117.5 (3)
N5—Co—O1119.81 (7)C23—C22—H22A121.3
O2—Co—O1167.10 (7)C21—C22—H22A121.3
C9—O1—C8114.91 (18)C22—C23—C24122.0 (3)
C9—O1—Co120.08 (13)C22—C23—H23A119.0
C8—O1—Co119.10 (14)C24—C23—H23A119.0
C29—O2—C28113.99 (18)C25—C24—C23121.4 (3)
C29—O2—Co120.85 (14)C25—C24—H24A119.3
C28—O2—Co122.57 (15)C23—C24—H24A119.3
O13—O13—N130(10)C24—C25—C26116.1 (3)
O14—O14—N130(10)C24—C25—H25A121.9
C7—N1—C1104.94 (19)C26—C25—H25A121.9
C7—N1—Co120.31 (17)N6—C26—C25130.9 (2)
C1—N1—Co134.50 (15)N6—C26—C21105.9 (2)
C7—N2—C6106.7 (2)C25—C26—C21123.2 (2)
C7—N2—C17125.9 (2)N5—C27—N6113.1 (2)
C6—N2—C17127.1 (2)N5—C27—C28123.5 (2)
C10—N3—C16105.6 (2)N6—C27—C28123.2 (2)
C10—N3—Co120.51 (16)O2—C28—C27104.38 (19)
C16—N3—Co133.02 (16)O2—C28—H28A110.9
C10—N4—C11106.8 (2)C27—C28—H28A110.9
C10—N4—C19125.9 (2)O2—C28—H28B110.9
C11—N4—C19127.0 (2)C27—C28—H28B110.9
C27—N5—C21105.0 (2)H28A—C28—H28B108.9
C27—N5—Co116.83 (17)O2—C29—C30104.42 (19)
C21—N5—Co137.15 (16)O2—C29—H29A110.9
C27—N6—C26106.5 (2)C30—C29—H29A110.9
C27—N6—C37126.9 (2)O2—C29—H29B110.9
C26—N6—C37126.2 (2)C30—C29—H29B110.9
C30—N7—C36105.0 (2)H29A—C29—H29B108.9
C30—N7—Co117.67 (16)N7—C30—N8113.7 (2)
C36—N7—Co136.96 (16)N7—C30—C29122.6 (2)
C30—N8—C31106.5 (2)N8—C30—C29123.7 (2)
C30—N8—C39129.1 (2)C32—C31—N8131.2 (2)
C31—N8—C39124.2 (2)C32—C31—C36122.7 (2)
O5—N9—O4123.9 (3)N8—C31—C36106.2 (2)
O5—N9—C42118.2 (4)C33—C32—C31116.9 (3)
O4—N9—C42117.9 (3)C33—C32—H32A121.5
O6—N10—O7123.9 (3)C31—C32—H32A121.5
O6—N10—C44118.3 (3)C32—C33—C34121.0 (3)
O7—N10—C44117.9 (3)C32—C33—H33A119.5
O9'—N11—O939.6 (6)C34—C33—H33A119.5
O9'—N11—O879.5 (8)C35—C34—C33121.9 (2)
O9—N11—O8113.3 (6)C35—C34—H34A119.0
O9'—N11—O8'123.6 (8)C33—C34—H34A119.0
O9—N11—O8'105.6 (6)C34—C35—C36117.4 (2)
O8—N11—O8'84.5 (5)C34—C35—H35A121.3
O9'—N11—C46119.3 (7)C36—C35—H35A121.3
O9—N11—C46117.2 (5)C35—C36—C31120.1 (2)
O8—N11—C46115.1 (4)C35—C36—N7131.4 (2)
O8'—N11—C46116.5 (4)C31—C36—N7108.6 (2)
O11—N12—O12123.9 (2)N6—C37—C38111.9 (2)
O11—N12—C48118.1 (2)N6—C37—H37A109.2
O12—N12—C48118.0 (2)C38—C37—H37A109.2
O13—N13—O130.0 (2)N6—C37—H37B109.2
O13—N13—O14122.8 (2)C38—C37—H37B109.2
O13—N13—O14122.8 (2)H37A—C37—H37B107.9
O13—N13—O14122.8 (2)C37—C38—H38A109.5
O13—N13—O14122.8 (2)C37—C38—H38B109.5
O14—N13—O140.00 (19)H38A—C38—H38B109.5
O13—N13—C50118.6 (2)C37—C38—H38C109.5
O13—N13—C50118.6 (2)H38A—C38—H38C109.5
O14—N13—C50118.6 (2)H38B—C38—H38C109.5
O14—N13—C50118.6 (2)N8—C39—C40111.6 (2)
O15—N14—O16123.0 (3)N8—C39—H39A109.3
O15—N14—C52118.2 (2)C40—C39—H39A109.3
O16—N14—C52118.7 (2)N8—C39—H39B109.3
C53—N15—C54120.6 (3)C40—C39—H39B109.3
C53—N15—C55124.2 (4)H39A—C39—H39B108.0
C54—N15—C55115.0 (3)C39—C40—H40A109.5
C56—N16—C58122.2 (3)C39—C40—H40B109.5
C56—N16—C57120.8 (3)H40A—C40—H40B109.5
C58—N16—C57116.8 (3)C39—C40—H40C109.5
N1—C1—C2130.4 (2)H40A—C40—H40C109.5
N1—C1—C6109.3 (2)H40B—C40—H40C109.5
C2—C1—C6120.3 (2)O3—C41—C46124.5 (3)
C3—C2—C1117.4 (2)O3—C41—C42125.1 (3)
C3—C2—H2A121.3C46—C41—C42110.4 (2)
C1—C2—H2A121.3C43—C42—C41124.9 (3)
C2—C3—C4122.0 (2)C43—C42—N9116.5 (3)
C2—C3—H3A119.0C41—C42—N9118.5 (3)
C4—C3—H3A119.0C42—C43—C44119.5 (3)
C5—C4—C3121.2 (3)C42—C43—H43A120.2
C5—C4—H4A119.4C44—C43—H43A120.2
C3—C4—H4A119.4C45—C44—C43120.3 (3)
C6—C5—C4116.6 (2)C45—C44—N10119.5 (3)
C6—C5—H5A121.7C43—C44—N10120.1 (3)
C4—C5—H5A121.7C46—C45—C44119.8 (3)
C5—C6—N2131.9 (2)C46—C45—H45A120.1
C5—C6—C1122.6 (2)C44—C45—H45A120.1
N2—C6—C1105.6 (2)C45—C46—C41125.0 (3)
N1—C7—N2113.5 (2)C45—C46—N11113.4 (3)
N1—C7—C8122.8 (2)C41—C46—N11121.6 (3)
N2—C7—C8123.7 (2)O10—C47—C48124.0 (2)
O1—C8—C7104.67 (18)O10—C47—C52125.0 (3)
O1—C8—H8A110.8C48—C47—C52110.9 (2)
C7—C8—H8A110.8C49—C48—C47125.3 (2)
O1—C8—H8B110.8C49—C48—N12117.3 (2)
C7—C8—H8B110.8C47—C48—N12117.3 (2)
H8A—C8—H8B108.9C48—C49—C50118.7 (3)
O1—C9—C10104.92 (19)C48—C49—H49A120.6
O1—C9—H9A110.8C50—C49—H49A120.6
C10—C9—H9A110.8C51—C50—C49120.9 (2)
O1—C9—H9B110.8C51—C50—N13120.1 (2)
C10—C9—H9B110.8C49—C50—N13119.0 (2)
H9A—C9—H9B108.8C52—C51—C50119.4 (2)
N3—C10—N4112.9 (2)C52—C51—H51A120.3
N3—C10—C9122.2 (2)C50—C51—H51A120.3
N4—C10—C9124.8 (2)C51—C52—N14117.7 (2)
C12—C11—N4131.8 (2)C51—C52—C47124.4 (3)
C12—C11—C16122.3 (2)N14—C52—C47117.8 (2)
N4—C11—C16105.9 (2)O17—C53—N15127.5 (4)
C11—C12—C13116.0 (3)O17—C53—H53116.3
C11—C12—H12A122.0N15—C53—H53116.3
C13—C12—H12A122.0N15—C54—H54A109.5
C12—C13—C14122.2 (2)N15—C54—H54B109.5
C12—C13—H13A118.9H54A—C54—H54B109.5
C14—C13—H13A118.9N15—C54—H54C109.5
C15—C14—C13121.2 (2)H54A—C54—H54C109.5
C15—C14—H14A119.4H54B—C54—H54C109.5
C13—C14—H14A119.4N15—C55—H55A109.5
C14—C15—C16117.4 (3)N15—C55—H55B109.5
C14—C15—H15A121.3H55A—C55—H55B109.5
C16—C15—H15A121.3N15—C55—H55C109.5
C15—C16—N3130.4 (2)H55A—C55—H55C109.5
C15—C16—C11120.9 (2)H55B—C55—H55C109.5
N3—C16—C11108.7 (2)O18—C56—N16126.1 (3)
N2—C17—C18112.7 (2)O18—C56—H56A117.0
N2—C17—H17A109.0N16—C56—H56A117.0
C18—C17—H17A109.0N16—C57—H57A109.5
N2—C17—H17B109.0N16—C57—H57B109.5
C18—C17—H17B109.0H57A—C57—H57B109.5
H17A—C17—H17B107.8N16—C57—H57C109.5
C17—C18—H18A109.5H57A—C57—H57C109.5
C17—C18—H18B109.5H57B—C57—H57C109.5
H18A—C18—H18B109.5N16—C58—H58A109.5
C17—C18—H18C109.5N16—C58—H58B109.5
H18A—C18—H18C109.5H58A—C58—H58B109.5
H18B—C18—H18C109.5N16—C58—H58C109.5
N4—C19—C20111.7 (2)H58A—C58—H58C109.5
N4—C19—H19A109.3H58B—C58—H58C109.5
C20—C19—H19A109.3
N1—Co—O1—C9−155.93 (19)Co—N5—C21—C26168.72 (18)
N3—Co—O1—C96.00 (17)C27—N5—C21—C22−178.8 (3)
N7—Co—O1—C9105.49 (18)Co—N5—C21—C22−11.2 (4)
N5—Co—O1—C9−67.64 (19)N5—C21—C22—C23−179.5 (3)
O2—Co—O1—C9128.0 (3)C26—C21—C22—C230.6 (4)
N1—Co—O1—C8−4.36 (17)C21—C22—C23—C24−0.6 (4)
N3—Co—O1—C8157.56 (18)C22—C23—C24—C250.0 (5)
N7—Co—O1—C8−102.94 (17)C23—C24—C25—C260.4 (4)
N5—Co—O1—C883.92 (18)C27—N6—C26—C25179.1 (3)
O2—Co—O1—C8−80.5 (4)C37—N6—C26—C255.1 (5)
N1—Co—O2—C29−106.16 (18)C27—N6—C26—C21−0.6 (3)
N3—Co—O2—C2984.01 (19)C37—N6—C26—C21−174.5 (2)
N7—Co—O2—C29−10.14 (17)C24—C25—C26—N6179.9 (3)
N5—Co—O2—C29160.60 (19)C24—C25—C26—C21−0.4 (4)
O1—Co—O2—C29−33.6 (4)N5—C21—C26—N6−0.3 (3)
N1—Co—O2—C2893.21 (19)C22—C21—C26—N6179.6 (2)
N3—Co—O2—C28−76.6 (2)N5—C21—C26—C25180.0 (2)
N7—Co—O2—C28−170.8 (2)C22—C21—C26—C25−0.1 (4)
N5—Co—O2—C28−0.04 (18)C21—N5—C27—N6−1.6 (3)
O1—Co—O2—C28165.8 (3)Co—N5—C27—N6−172.15 (16)
N3—Co—N1—C7−28.3 (2)C21—N5—C27—C28174.0 (2)
N7—Co—N1—C791.11 (19)Co—N5—C27—C283.5 (3)
N5—Co—N1—C7−119.97 (18)C26—N6—C27—N51.4 (3)
O2—Co—N1—C7166.19 (18)C37—N6—C27—N5175.3 (2)
O1—Co—N1—C7−0.91 (17)C26—N6—C27—C28−174.2 (2)
N3—Co—N1—C1158.5 (2)C37—N6—C27—C28−0.3 (4)
N7—Co—N1—C1−82.1 (2)C29—O2—C28—C27−160.4 (2)
N5—Co—N1—C166.8 (2)Co—O2—C28—C271.5 (3)
O2—Co—N1—C1−7.0 (2)N5—C27—C28—O2−3.2 (3)
O1—Co—N1—C1−174.1 (2)N6—C27—C28—O2172.0 (2)
N1—Co—N3—C1021.8 (3)C28—O2—C29—C30171.8 (2)
N7—Co—N3—C10−97.34 (19)Co—O2—C29—C309.6 (3)
N5—Co—N3—C10117.65 (19)C36—N7—C30—N8−0.1 (3)
O2—Co—N3—C10−173.70 (17)Co—N7—C30—N8174.38 (16)
O1—Co—N3—C10−5.72 (18)C36—N7—C30—C29179.7 (2)
N1—Co—N3—C16−146.1 (2)Co—N7—C30—C29−5.9 (3)
N7—Co—N3—C1694.8 (2)C31—N8—C30—N7−0.6 (3)
N5—Co—N3—C16−50.2 (2)C39—N8—C30—N7−175.7 (2)
O2—Co—N3—C1618.4 (2)C31—N8—C30—C29179.6 (2)
O1—Co—N3—C16−173.6 (2)C39—N8—C30—C294.5 (4)
N1—Co—N5—C27−104.17 (18)O2—C29—C30—N7−2.4 (3)
N3—Co—N5—C27115.76 (18)O2—C29—C30—N8177.3 (2)
N7—Co—N5—C2713.8 (3)C30—N8—C31—C32−179.7 (3)
O2—Co—N5—C27−1.72 (17)C39—N8—C31—C32−4.2 (4)
O1—Co—N5—C27−178.11 (16)C30—N8—C31—C361.1 (3)
N1—Co—N5—C2189.3 (2)C39—N8—C31—C36176.5 (2)
N3—Co—N5—C21−50.8 (2)N8—C31—C32—C33−178.2 (3)
N7—Co—N5—C21−152.7 (2)C36—C31—C32—C330.9 (4)
O2—Co—N5—C21−168.3 (2)C31—C32—C33—C340.1 (4)
O1—Co—N5—C2115.3 (3)C32—C33—C34—C35−0.1 (4)
N1—Co—N7—C30109.79 (18)C33—C34—C35—C36−0.8 (4)
N3—Co—N7—C30−104.75 (18)C34—C35—C36—C311.7 (4)
N5—Co—N7—C30−7.5 (3)C34—C35—C36—N7−179.9 (3)
O2—Co—N7—C307.96 (17)C32—C31—C36—C35−1.9 (4)
O1—Co—N7—C30−177.14 (17)N8—C31—C36—C35177.5 (2)
N1—Co—N7—C36−78.0 (2)C32—C31—C36—N7179.5 (2)
N3—Co—N7—C3667.5 (2)N8—C31—C36—N7−1.2 (3)
N5—Co—N7—C36164.7 (2)C30—N7—C36—C35−177.6 (3)
O2—Co—N7—C36−179.8 (2)Co—N7—C36—C359.5 (4)
O1—Co—N7—C36−4.9 (2)C30—N7—C36—C310.8 (3)
O13—O13—N13—O140.00 (19)Co—N7—C36—C31−172.02 (18)
O13—O13—N13—O140.00 (19)C27—N6—C37—C38−95.6 (3)
O13—O13—N13—C500.00 (14)C26—N6—C37—C3877.1 (3)
O14—O14—N13—O130.00 (10)C30—N8—C39—C40101.1 (3)
O14—O14—N13—O130.00 (10)C31—N8—C39—C40−73.2 (3)
O14—O14—N13—C500.00 (15)O3—C41—C42—C43175.2 (3)
C7—N1—C1—C2178.0 (3)C46—C41—C42—C43−1.8 (4)
Co—N1—C1—C2−8.1 (4)O3—C41—C42—N9−1.4 (5)
C7—N1—C1—C6−0.5 (3)C46—C41—C42—N9−178.4 (3)
Co—N1—C1—C6173.48 (17)O5—N9—C42—C43142.6 (3)
N1—C1—C2—C3179.9 (2)O4—N9—C42—C43−37.0 (4)
C6—C1—C2—C3−1.9 (4)O5—N9—C42—C41−40.5 (4)
C1—C2—C3—C40.7 (4)O4—N9—C42—C41139.9 (3)
C2—C3—C4—C50.6 (4)C41—C42—C43—C443.3 (4)
C3—C4—C5—C6−0.7 (4)N9—C42—C43—C44180.0 (3)
C4—C5—C6—N2179.2 (3)C42—C43—C44—C45−2.9 (4)
C4—C5—C6—C1−0.5 (4)C42—C43—C44—N10−178.8 (2)
C7—N2—C6—C5179.6 (3)O6—N10—C44—C45179.9 (3)
C17—N2—C6—C5−6.3 (4)O7—N10—C44—C45−0.9 (4)
C7—N2—C6—C1−0.6 (3)O6—N10—C44—C43−4.2 (4)
C17—N2—C6—C1173.5 (2)O7—N10—C44—C43175.0 (2)
N1—C1—C6—C5−179.5 (2)C43—C44—C45—C461.1 (4)
C2—C1—C6—C51.9 (4)N10—C44—C45—C46177.0 (3)
N1—C1—C6—N20.7 (3)C44—C45—C46—C410.4 (5)
C2—C1—C6—N2−177.9 (2)C44—C45—C46—N11−176.1 (3)
C1—N1—C7—N20.0 (3)O3—C41—C46—C45−177.1 (3)
Co—N1—C7—N2−174.95 (16)C42—C41—C46—C45−0.1 (4)
C1—N1—C7—C8−178.9 (2)O3—C41—C46—N11−0.9 (5)
Co—N1—C7—C86.1 (3)C42—C41—C46—N11176.1 (3)
C6—N2—C7—N10.4 (3)O9'—N11—C46—C45−150.0 (9)
C17—N2—C7—N1−173.8 (2)O9—N11—C46—C45164.8 (6)
C6—N2—C7—C8179.3 (2)O8—N11—C46—C45−58.3 (6)
C17—N2—C7—C85.1 (4)O8'—N11—C46—C4538.4 (5)
C9—O1—C8—C7160.6 (2)O9'—N11—C46—C4133.4 (10)
Co—O1—C8—C77.6 (2)O9—N11—C46—C41−11.7 (7)
N1—C7—C8—O1−8.8 (3)O8—N11—C46—C41125.2 (5)
N2—C7—C8—O1172.4 (2)O8'—N11—C46—C41−138.2 (5)
C8—O1—C9—C10−157.7 (2)O10—C47—C48—C49169.2 (3)
Co—O1—C9—C10−5.0 (2)C52—C47—C48—C49−6.8 (4)
C16—N3—C10—N4−1.1 (3)O10—C47—C48—N12−7.7 (4)
Co—N3—C10—N4−171.93 (16)C52—C47—C48—N12176.3 (2)
C16—N3—C10—C9176.2 (2)O11—N12—C48—C49140.6 (3)
Co—N3—C10—C95.4 (3)O12—N12—C48—C49−39.2 (4)
C11—N4—C10—N31.3 (3)O11—N12—C48—C47−42.2 (4)
C19—N4—C10—N3175.7 (2)O12—N12—C48—C47138.0 (3)
C11—N4—C10—C9−176.0 (2)C47—C48—C49—C504.0 (4)
C19—N4—C10—C9−1.5 (4)N12—C48—C49—C50−179.1 (2)
O1—C9—C10—N30.0 (3)C48—C49—C50—C510.0 (4)
O1—C9—C10—N4177.0 (2)C48—C49—C50—N13179.5 (2)
C10—N4—C11—C12178.7 (3)O13—N13—C50—C51−178.5 (3)
C19—N4—C11—C124.3 (4)O13—N13—C50—C51−178.5 (3)
C10—N4—C11—C16−0.9 (3)O14—N13—C50—C510.6 (4)
C19—N4—C11—C16−175.3 (2)O14—N13—C50—C510.6 (4)
N4—C11—C12—C13−179.5 (3)O13—N13—C50—C491.9 (4)
C16—C11—C12—C130.1 (4)O13—N13—C50—C491.9 (4)
C11—C12—C13—C14−0.2 (4)O14—N13—C50—C49−178.9 (2)
C12—C13—C14—C150.1 (5)O14—N13—C50—C49−178.9 (2)
C13—C14—C15—C160.3 (4)C49—C50—C51—C52−0.3 (4)
C14—C15—C16—N3179.1 (3)N13—C50—C51—C52−179.8 (3)
C14—C15—C16—C11−0.5 (4)C50—C51—C52—N14−179.9 (3)
C10—N3—C16—C15−179.2 (3)C50—C51—C52—C47−3.3 (4)
Co—N3—C16—C15−10.0 (4)O15—N14—C52—C5133.4 (4)
C10—N3—C16—C110.5 (3)O16—N14—C52—C51−145.2 (3)
Co—N3—C16—C11169.68 (17)O15—N14—C52—C47−143.4 (3)
C12—C11—C16—C150.3 (4)O16—N14—C52—C4738.0 (4)
N4—C11—C16—C15180.0 (2)O10—C47—C52—C51−169.6 (3)
C12—C11—C16—N3−179.4 (2)C48—C47—C52—C516.4 (4)
N4—C11—C16—N30.2 (3)O10—C47—C52—N147.0 (4)
C7—N2—C17—C18−110.1 (3)C48—C47—C52—N14−177.0 (2)
C6—N2—C17—C1876.9 (3)C54—N15—C53—O17−1.8 (9)
C10—N4—C19—C20−86.1 (3)C55—N15—C53—O17−176.0 (7)
C11—N4—C19—C2087.2 (3)C58—N16—C56—O18−176.6 (4)
C27—N5—C21—C261.1 (3)C57—N16—C56—O18−1.4 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C18—H18B···O12i0.982.573.342 (4)135
C15—H15A···O130.952.563.191 (3)124
C18—H18B···O12i0.982.573.342 (4)135
C28—H28A···O17ii0.992.383.365 (4)173
C28—H28B···O10iii0.992.292.994 (3)128
C29—H29A···O140.992.393.331 (3)158
C35—H35A···O7i0.952.443.158 (3)133
C53—H53···O9'iv0.952.393.242 (7)148
C56—H56A···O3v0.952.463.335 (4)154

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2889).

References

  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2004). RAPID-AUTO Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst D65, 148–155. [PMC free article] [PubMed]
  • Wu, H., Yun, R., Huang, X., Sun, Q. & Qi, B. (2009). Acta Cryst. E65, m851. [PMC free article] [PubMed]
  • Wu, H., Yun, R., Li, K., Tao, S. & Wang, K. (2009). Acta Cryst. E65, m786. [PMC free article] [PubMed]
  • Yun, R., Ying, W., Qi, B., Fan, X. & Wu, H. (2008). Acta Cryst. E64, m1529. [PMC free article] [PubMed]

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