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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): m816.
Published online 2010 June 18. doi:  10.1107/S1600536810022750
PMCID: PMC3006859

Tris(1,10-phenanthroline)cobalt(II) bis­(perrhenate) monohydrate

Abstract

In the title compound, [Co(C12H8N2)3][ReO4]2·H2O, the CoII atom is coordinated by three 1,10-phenanthroline ligands in a distorted octa­hedral arrangement. In the crystal, the components are linked by O—H(...)O, C—H(...)O and aromatic π–π stacking [shortest centroid–centroid separation = 3.659 (5) Å] inter­actions.

Related literature

For a related structure and biological background information, see: Li et al. (2010 [triangle]). For geometrical features in related structures, see: Ikotun et al. (2008 [triangle]); Addison et al. (1984 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m816-scheme1.jpg

Experimental

Crystal data

  • [Co(C12H8N2)3][ReO4]2·H2O
  • M r = 1117.96
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m816-efi1.jpg
  • a = 10.350 (5) Å
  • b = 13.133 (3) Å
  • c = 14.392 (2) Å
  • α = 73.58 (2)°
  • β = 71.18 (2)°
  • γ = 78.50 (3)°
  • V = 1763.6 (10) Å3
  • Z = 2
  • Ag Kα radiation
  • λ = 0.56087 Å
  • μ = 3.97 mm−1
  • T = 293 K
  • 0.17 × 0.15 × 0.13 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • 24086 measured reflections
  • 17274 independent reflections
  • 8056 reflections with I > 2σ(I)
  • R int = 0.027
  • 2 standard reflections every 120 min intensity decay: 3%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.083
  • wR(F 2) = 0.244
  • S = 0.98
  • 17274 reflections
  • 493 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 5.34 e Å−3
  • Δρmin = −5.31 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 [triangle]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and DIAMOND (Brandenburg & Putz, 2005 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022750/hb5497sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022750/hb5497Isup2.hkl

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

supplementary crystallographic information

Comment

As part of our exploration of metal complexes with possible biological applications (Li et al., 2010), we now report the structure of the title compound, (I)> It contains one cationic mononuclear species [Co(phen)3]2+, two perrhenate anions, and one lattice water molecule (Fig. 1). The unique crystallographically independent CoII exhibits a distorted octahedral environment with a τ value of 0.05 (2) calaculated using the approach of Reedijk and co-workers (Addison et al., 1984). Six nitrogen donors from three bidendate phen ligands are coordinated to CoII. The CoII is slightly displaced from the octahedron centroid by 0.053 (1) Å. The structural data are in good agreement with those of the cobalt(II) complexes which exhibit a similar geometry (Li et al., 2010). The phen molecules are nearly planar (mean deviation is 0.048 (3) Å). The mean dihedral angle between the two pyridyl planes being 3.0 (2)°. The intra-ring C—N and C—C bond distances have respectively the usual mean values 1,344 (8) Å) and 1.397 (11)Å (Ikotun et al., 2008). The angles subtended by the bidentate phen ligand at the cobalt atom are comparable with a mean value 77,9(2)°. The charges are counterbalanced by uncoordinated perrhenate anions which are connected through hydrogen bonds (C—H ···O) to the coordinated phen molecules (Table 1 and Fig. 2). The mononuclear units are also interconnected through intermolecular hydrogen bonds involving the uncoordinated water molecule and perrhenate oxygen atoms (Table 1) to form trinuclear unit which is further stabilized by the inter-phen ring p-p stacking (Fig. 2). The mean interplanar distance is 3.719 Å and the angle made by ring normal and the vector between the ring centroids is 7.95° (mean value).

Experimental

An aqueous solution (15 ml) of NH4ReO4 (0.54 g; 2 mmol) was slowly added under stirring to a mixture of ethanol (5 ml) and water (15 ml) containing phen (0,42 g; 3 mmol) and CoCl2 (0.2 g; 1 mmol). The purple solution was left in air for a week and pink prisms of (I) were recovered.

Refinement

The water H atoms were located in a difference map and freely refined. All H atoms attached to C atoms were fixed geometrically and treated as riding, with C—H = 0.93 Å and with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The structure of (I) with displacement ellipsoids drawn at the 30% probability level.
Fig. 2.
Hydrogen-bonding interactions in (I); the H-atoms not involved in H-bonding are omitted.

Crystal data

[Co(C12H8N2)3][ReO4]2·H2OZ = 2
Mr = 1117.96F(000) = 1066
Triclinic, P1Dx = 2.105 Mg m3
Hall symbol: -P 1Ag Kα radiation, λ = 0.56087 Å
a = 10.350 (5) ÅCell parameters from 25 reflections
b = 13.133 (3) Åθ = 9–11°
c = 14.392 (2) ŵ = 3.97 mm1
α = 73.58 (2)°T = 293 K
β = 71.18 (2)°Prism, pink
γ = 78.50 (3)°0.17 × 0.15 × 0.13 mm
V = 1763.6 (10) Å3

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.027
Radiation source: fine-focus sealed tubeθmax = 28.0°, θmin = 2.2°
graphiteh = −17→17
non–profiled ω scansk = −21→21
24086 measured reflectionsl = −6→24
17274 independent reflections2 standard reflections every 120 min
8056 reflections with I > 2σ(I) intensity decay: 3%

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)] = 0.083Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.244H atoms treated by a mixture of independent and constrained refinement
S = 0.98w = 1/[σ2(Fo2) + (0.1366P)2] where P = (Fo2 + 2Fc2)/3
17274 reflections(Δ/σ)max = 0.035
493 parametersΔρmax = 5.34 e Å3
3 restraintsΔρmin = −5.31 e Å3

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*/Ueq
Re20.81148 (4)0.32794 (3)0.47046 (3)0.05237 (11)
Re10.42492 (4)0.26252 (3)0.05290 (2)0.05389 (11)
Co10.77573 (8)0.78259 (7)0.30120 (6)0.03267 (17)
N10.9503 (5)0.6807 (4)0.2371 (4)0.0360 (11)
N20.6819 (5)0.6648 (4)0.2795 (4)0.0373 (11)
N30.7832 (6)0.8921 (5)0.1575 (4)0.0386 (11)
N40.8990 (5)0.8977 (4)0.2982 (4)0.0357 (10)
N50.5837 (5)0.8693 (5)0.3666 (5)0.0383 (11)
N60.7463 (5)0.7149 (4)0.4579 (4)0.0353 (10)
O10.5215 (9)0.2398 (7)−0.0613 (6)0.087 (2)
O20.4816 (12)0.3588 (9)0.0815 (7)0.119 (4)
O30.4311 (14)0.1461 (8)0.1403 (7)0.125 (4)
O40.2576 (10)0.2997 (10)0.0475 (10)0.123 (4)
O50.8842 (9)0.4410 (6)0.4074 (8)0.089 (3)
O60.6492 (9)0.3431 (8)0.4588 (8)0.102 (3)
O70.9060 (11)0.2337 (12)0.4291 (8)0.132 (4)
O80.7999 (11)0.3087 (9)0.5966 (6)0.113 (4)
O90.6895 (13)0.1463 (10)0.7811 (8)0.118 (3)
H1090.69 (2)0.180 (17)0.721 (4)0.230*
H2090.622 (12)0.166 (14)0.828 (8)0.153*
C11.0837 (7)0.6876 (6)0.2185 (6)0.0453 (15)
H11.10920.73740.24210.054*
C21.1877 (7)0.6209 (6)0.1635 (6)0.0485 (17)
H21.27980.62910.14950.058*
C31.1533 (8)0.5461 (7)0.1318 (7)0.0541 (19)
H31.22160.50250.09590.065*
C41.0142 (8)0.5333 (6)0.1528 (6)0.0463 (15)
C50.9697 (9)0.4542 (7)0.1245 (8)0.062 (2)
H51.03380.40690.09040.074*
C60.8313 (10)0.4475 (8)0.1478 (9)0.070 (3)
H60.80380.39480.12910.084*
C70.7289 (9)0.5179 (6)0.1990 (6)0.0483 (16)
C80.5883 (10)0.5129 (7)0.2260 (8)0.061 (2)
H80.55570.46450.20530.073*
C90.5006 (9)0.5762 (7)0.2806 (8)0.060 (2)
H90.40710.56940.30220.073*
C100.5501 (7)0.6541 (6)0.3057 (6)0.0476 (16)
H100.48730.69990.34230.057*
C110.7723 (7)0.5954 (5)0.2277 (5)0.0362 (12)
C120.9166 (6)0.6051 (5)0.2043 (5)0.0345 (12)
C130.7240 (8)0.8886 (7)0.0902 (6)0.0498 (17)
H130.68490.82750.09870.060*
C140.7176 (9)0.9729 (8)0.0066 (6)0.060 (2)
H140.67150.9689−0.03780.072*
C150.7792 (9)1.0608 (7)−0.0092 (6)0.060 (2)
H150.77801.1167−0.06560.072*
C160.8444 (8)1.0663 (5)0.0601 (6)0.0474 (17)
C170.9158 (10)1.1552 (7)0.0493 (8)0.062 (2)
H170.91841.2130−0.00620.075*
C180.9789 (9)1.1563 (6)0.1182 (8)0.063 (2)
H181.02311.21480.10980.076*
C190.9781 (7)1.0697 (6)0.2024 (7)0.0468 (17)
C201.0409 (9)1.0668 (7)0.2771 (8)0.059 (2)
H201.08721.12300.27170.071*
C211.0327 (8)0.9808 (8)0.3570 (7)0.056 (2)
H211.07570.97740.40560.067*
C220.9605 (7)0.8977 (6)0.3669 (6)0.0443 (15)
H220.95490.84050.42300.053*
C230.9084 (6)0.9817 (5)0.2161 (5)0.0373 (13)
C240.8440 (6)0.9794 (5)0.1435 (5)0.0374 (13)
C250.5018 (7)0.9451 (6)0.3215 (6)0.0445 (15)
H250.52890.96760.25150.053*
C260.3778 (8)0.9917 (7)0.3749 (7)0.0548 (19)
H260.32421.04470.34060.066*
C270.3352 (7)0.9605 (6)0.4761 (7)0.0524 (19)
H270.25090.99020.51170.063*
C280.4194 (7)0.8820 (6)0.5285 (6)0.0434 (15)
C290.3850 (8)0.8462 (7)0.6356 (6)0.0514 (18)
H290.30230.87390.67480.062*
C300.4710 (8)0.7722 (7)0.6816 (6)0.0528 (18)
H300.44720.75170.75170.063*
C310.5963 (7)0.7258 (6)0.6245 (5)0.0436 (15)
C320.6871 (8)0.6473 (7)0.6673 (6)0.0530 (18)
H320.66950.62520.73710.064*
C330.8045 (9)0.6025 (7)0.6043 (6)0.0548 (19)
H330.86420.54820.63130.066*
C340.8303 (7)0.6406 (6)0.5006 (5)0.0451 (15)
H340.91050.61250.45900.054*
C350.6306 (6)0.7583 (5)0.5182 (5)0.0363 (12)
C360.5425 (6)0.8397 (5)0.4702 (5)0.0359 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Re20.0577 (2)0.05247 (19)0.04822 (18)−0.01579 (14)−0.01504 (15)−0.00749 (14)
Re10.0644 (2)0.0581 (2)0.03748 (16)−0.00922 (15)−0.00999 (14)−0.01234 (13)
Co10.0324 (4)0.0366 (4)0.0285 (4)−0.0069 (3)−0.0071 (3)−0.0067 (3)
N10.035 (2)0.042 (3)0.032 (2)−0.007 (2)−0.011 (2)−0.008 (2)
N20.035 (2)0.039 (3)0.036 (3)−0.012 (2)−0.006 (2)−0.005 (2)
N30.036 (2)0.044 (3)0.033 (3)−0.007 (2)−0.009 (2)−0.005 (2)
N40.035 (2)0.042 (3)0.035 (3)−0.007 (2)−0.012 (2)−0.012 (2)
N50.031 (2)0.042 (3)0.042 (3)−0.003 (2)−0.012 (2)−0.010 (2)
N60.033 (2)0.039 (3)0.031 (2)−0.007 (2)−0.006 (2)−0.006 (2)
O10.087 (5)0.113 (6)0.060 (4)0.007 (5)−0.019 (4)−0.033 (4)
O20.165 (10)0.136 (8)0.082 (6)−0.086 (7)−0.030 (7)−0.025 (6)
O30.219 (13)0.079 (6)0.077 (6)−0.036 (7)−0.055 (8)0.007 (5)
O40.071 (5)0.132 (9)0.166 (11)0.012 (6)−0.023 (6)−0.064 (8)
O50.087 (5)0.063 (4)0.113 (7)−0.024 (4)−0.033 (5)0.001 (4)
O60.088 (6)0.115 (7)0.126 (8)−0.038 (5)−0.046 (6)−0.027 (6)
O70.114 (8)0.201 (12)0.082 (7)−0.069 (8)−0.021 (6)−0.011 (8)
O80.122 (7)0.151 (9)0.046 (4)0.025 (7)−0.025 (5)−0.017 (5)
O90.141 (10)0.137 (9)0.087 (7)−0.011 (8)−0.042 (7)−0.035 (7)
C10.036 (3)0.055 (4)0.044 (4)−0.008 (3)−0.014 (3)−0.005 (3)
C20.037 (3)0.054 (4)0.046 (4)−0.002 (3)−0.006 (3)−0.007 (3)
C30.042 (4)0.051 (4)0.055 (5)0.006 (3)−0.004 (3)−0.010 (4)
C40.044 (3)0.046 (4)0.048 (4)−0.005 (3)−0.010 (3)−0.014 (3)
C50.060 (5)0.049 (4)0.074 (6)0.004 (4)−0.009 (4)−0.031 (4)
C60.070 (6)0.066 (6)0.091 (8)−0.003 (5)−0.017 (5)−0.052 (6)
C70.054 (4)0.046 (4)0.048 (4)−0.019 (3)−0.011 (3)−0.010 (3)
C80.063 (5)0.059 (5)0.071 (6)−0.023 (4)−0.026 (5)−0.014 (4)
C90.047 (4)0.059 (5)0.079 (6)−0.021 (4)−0.009 (4)−0.022 (5)
C100.039 (3)0.055 (4)0.049 (4)−0.010 (3)−0.008 (3)−0.012 (3)
C110.036 (3)0.034 (3)0.038 (3)−0.008 (2)−0.010 (2)−0.004 (2)
C120.036 (3)0.032 (3)0.031 (3)−0.002 (2)−0.008 (2)−0.003 (2)
C130.055 (4)0.060 (4)0.036 (3)−0.003 (3)−0.016 (3)−0.013 (3)
C140.061 (5)0.079 (6)0.039 (4)0.003 (4)−0.026 (4)−0.008 (4)
C150.067 (5)0.060 (5)0.034 (4)0.002 (4)−0.012 (4)0.009 (3)
C160.049 (4)0.034 (3)0.045 (4)0.000 (3)−0.006 (3)0.001 (3)
C170.067 (5)0.038 (4)0.069 (6)−0.010 (3)−0.013 (5)0.002 (4)
C180.054 (4)0.040 (4)0.088 (7)−0.014 (3)−0.007 (5)−0.013 (4)
C190.036 (3)0.041 (3)0.061 (5)−0.009 (3)−0.003 (3)−0.018 (3)
C200.049 (4)0.057 (5)0.077 (6)−0.013 (4)−0.012 (4)−0.027 (5)
C210.041 (4)0.074 (5)0.067 (5)−0.008 (3)−0.019 (4)−0.036 (5)
C220.040 (3)0.054 (4)0.045 (4)−0.011 (3)−0.013 (3)−0.017 (3)
C230.027 (2)0.036 (3)0.044 (3)−0.005 (2)−0.003 (2)−0.010 (3)
C240.034 (3)0.040 (3)0.033 (3)−0.003 (2)−0.006 (2)−0.005 (2)
C250.044 (3)0.043 (3)0.047 (4)−0.005 (3)−0.019 (3)−0.007 (3)
C260.039 (3)0.056 (4)0.068 (5)−0.002 (3)−0.018 (4)−0.012 (4)
C270.034 (3)0.054 (4)0.069 (5)0.004 (3)−0.008 (3)−0.028 (4)
C280.037 (3)0.049 (4)0.045 (4)−0.010 (3)−0.002 (3)−0.019 (3)
C290.045 (4)0.066 (5)0.045 (4)−0.016 (3)0.002 (3)−0.026 (4)
C300.051 (4)0.070 (5)0.035 (3)−0.015 (4)0.000 (3)−0.019 (3)
C310.043 (3)0.061 (4)0.028 (3)−0.018 (3)−0.003 (3)−0.012 (3)
C320.052 (4)0.070 (5)0.030 (3)−0.022 (4)−0.006 (3)0.001 (3)
C330.053 (4)0.056 (4)0.047 (4)−0.011 (3)−0.020 (4)0.011 (3)
C340.044 (3)0.052 (4)0.034 (3)−0.005 (3)−0.010 (3)−0.003 (3)
C350.031 (3)0.044 (3)0.032 (3)−0.012 (2)−0.005 (2)−0.004 (2)
C360.031 (3)0.042 (3)0.038 (3)−0.008 (2)−0.009 (2)−0.012 (3)

Geometric parameters (Å, °)

Re2—O71.549 (15)C9—C101.407 (11)
Re2—O51.685 (8)C9—H90.9300
Re2—O61.708 (8)C10—H100.9300
Re2—O81.728 (8)C11—C121.445 (9)
Re1—O31.688 (9)C13—C141.395 (11)
Re1—O21.691 (9)C13—H130.9300
Re1—O11.700 (7)C14—C151.357 (14)
Re1—O41.724 (10)C14—H140.9300
Co1—N62.122 (5)C15—C161.397 (13)
Co1—N22.122 (5)C15—H150.9300
Co1—N12.136 (5)C16—C241.403 (9)
Co1—N42.147 (5)C16—C171.450 (12)
Co1—N32.148 (6)C17—C181.357 (15)
Co1—N52.151 (6)C17—H170.9300
N1—C11.336 (8)C18—C191.407 (12)
N1—C121.356 (8)C18—H180.9300
N2—C101.318 (8)C19—C201.414 (13)
N2—C111.362 (8)C19—C231.417 (9)
N3—C131.317 (9)C20—C211.359 (14)
N3—C241.352 (9)C20—H200.9300
N4—C221.337 (9)C21—C221.392 (11)
N4—C231.362 (9)C21—H210.9300
N5—C251.336 (9)C22—H220.9300
N5—C361.373 (9)C23—C241.418 (10)
N6—C341.324 (9)C25—C261.389 (11)
N6—C351.360 (8)C25—H250.9300
O9—H1090.85 (10)C26—C271.342 (13)
O9—H2090.86 (14)C26—H260.9300
C1—C21.422 (11)C27—C281.420 (11)
C1—H10.9300C27—H270.9300
C2—C31.341 (12)C28—C361.388 (9)
C2—H20.9300C28—C291.424 (11)
C3—C41.407 (11)C29—C301.358 (13)
C3—H30.9300C29—H290.9300
C4—C121.411 (9)C30—C311.418 (10)
C4—C51.417 (12)C30—H300.9300
C5—C61.378 (13)C31—C321.398 (11)
C5—H50.9300C31—C351.410 (9)
C6—C71.418 (12)C32—C331.397 (12)
C6—H60.9300C32—H320.9300
C7—C81.390 (12)C33—C341.386 (10)
C7—C111.396 (9)C33—H330.9300
C8—C91.319 (13)C34—H340.9300
C8—H80.9300C35—C361.432 (9)
O7—Re2—O5108.3 (5)N2—C11—C12116.7 (6)
O7—Re2—O6113.2 (5)C7—C11—C12121.2 (6)
O5—Re2—O6109.3 (5)N1—C12—C4123.8 (6)
O7—Re2—O8109.7 (5)N1—C12—C11117.5 (5)
O5—Re2—O8107.7 (6)C4—C12—C11118.7 (6)
O6—Re2—O8108.5 (5)N3—C13—C14122.7 (8)
O3—Re1—O2111.0 (5)N3—C13—H13118.7
O3—Re1—O1107.9 (5)C14—C13—H13118.7
O2—Re1—O1111.5 (5)C15—C14—C13119.4 (8)
O3—Re1—O4108.4 (6)C15—C14—H14120.3
O2—Re1—O4110.6 (6)C13—C14—H14120.3
O1—Re1—O4107.4 (5)C14—C15—C16119.3 (7)
N6—Co1—N294.4 (2)C14—C15—H15120.3
N6—Co1—N1101.4 (2)C16—C15—H15120.3
N2—Co1—N178.1 (2)C15—C16—C24118.1 (7)
N6—Co1—N493.0 (2)C15—C16—C17123.8 (8)
N2—Co1—N4169.5 (2)C24—C16—C17118.1 (8)
N1—Co1—N493.2 (2)C18—C17—C16121.6 (8)
N6—Co1—N3163.7 (2)C18—C17—H17119.2
N2—Co1—N396.8 (2)C16—C17—H17119.2
N1—Co1—N392.5 (2)C17—C18—C19120.6 (8)
N4—Co1—N377.5 (2)C17—C18—H18119.7
N6—Co1—N578.0 (2)C19—C18—H18119.7
N2—Co1—N594.3 (2)C18—C19—C20123.1 (7)
N1—Co1—N5172.3 (2)C18—C19—C23119.6 (8)
N4—Co1—N594.5 (2)C20—C19—C23117.3 (8)
N3—Co1—N589.4 (2)C21—C20—C19119.1 (7)
C1—N1—C12117.7 (6)C21—C20—H20120.5
C1—N1—Co1129.0 (5)C19—C20—H20120.5
C12—N1—Co1113.1 (4)C20—C21—C22120.7 (8)
C10—N2—C11117.6 (6)C20—C21—H21119.7
C10—N2—Co1128.5 (5)C22—C21—H21119.7
C11—N2—Co1113.8 (4)N4—C22—C21122.1 (8)
C13—N3—C24118.8 (6)N4—C22—H22119.0
C13—N3—Co1127.8 (5)C21—C22—H22119.0
C24—N3—Co1113.0 (4)N4—C23—C19122.3 (7)
C22—N4—C23118.5 (6)N4—C23—C24117.6 (6)
C22—N4—Co1128.4 (5)C19—C23—C24120.1 (7)
C23—N4—Co1113.1 (4)N3—C24—C16121.7 (7)
C25—N5—C36117.2 (6)N3—C24—C23118.2 (6)
C25—N5—Co1129.7 (5)C16—C24—C23120.1 (7)
C36—N5—Co1113.1 (4)N5—C25—C26122.8 (8)
C34—N6—C35118.8 (6)N5—C25—H25118.6
C34—N6—Co1127.0 (5)C26—C25—H25118.6
C35—N6—Co1114.2 (4)C27—C26—C25120.1 (8)
H109—O9—H209116 (16)C27—C26—H26119.9
N1—C1—C2121.7 (7)C25—C26—H26119.9
N1—C1—H1119.1C26—C27—C28119.7 (7)
C2—C1—H1119.1C26—C27—H27120.1
C3—C2—C1120.1 (7)C28—C27—H27120.1
C3—C2—H2120.0C36—C28—C27117.0 (7)
C1—C2—H2120.0C36—C28—C29119.2 (7)
C2—C3—C4120.2 (7)C27—C28—C29123.9 (7)
C2—C3—H3119.9C30—C29—C28121.2 (7)
C4—C3—H3119.9C30—C29—H29119.4
C3—C4—C12116.5 (7)C28—C29—H29119.4
C3—C4—C5123.6 (7)C29—C30—C31121.1 (7)
C12—C4—C5120.0 (7)C29—C30—H30119.4
C6—C5—C4119.8 (7)C31—C30—H30119.4
C6—C5—H5120.1C32—C31—C35117.7 (7)
C4—C5—H5120.1C32—C31—C30123.8 (7)
C5—C6—C7122.6 (8)C35—C31—C30118.5 (7)
C5—C6—H6118.7C33—C32—C31119.4 (7)
C7—C6—H6118.7C33—C32—H32120.3
C8—C7—C11117.4 (8)C31—C32—H32120.3
C8—C7—C6124.7 (8)C34—C33—C32118.7 (7)
C11—C7—C6117.8 (7)C34—C33—H33120.6
C9—C8—C7120.7 (8)C32—C33—H33120.6
C9—C8—H8119.6N6—C34—C33123.2 (7)
C7—C8—H8119.6N6—C34—H34118.4
C8—C9—C10119.2 (8)C33—C34—H34118.4
C8—C9—H9120.4N6—C35—C31122.2 (6)
C10—C9—H9120.4N6—C35—C36117.7 (6)
N2—C10—C9122.7 (8)C31—C35—C36120.1 (6)
N2—C10—H10118.7N5—C36—C28123.2 (6)
C9—C10—H10118.7N5—C36—C35117.0 (6)
N2—C11—C7122.1 (6)C28—C36—C35119.8 (6)
N6—Co1—N1—C1−86.0 (6)Co1—N1—C12—C4175.3 (6)
N2—Co1—N1—C1−178.2 (6)C1—N1—C12—C11177.9 (6)
N4—Co1—N1—C17.8 (6)Co1—N1—C12—C11−7.4 (7)
N3—Co1—N1—C185.4 (6)C3—C4—C12—N1−2.7 (11)
N5—Co1—N1—C1−170.6 (15)C5—C4—C12—N1177.6 (7)
N6—Co1—N1—C12100.1 (4)C3—C4—C12—C11−179.9 (7)
N2—Co1—N1—C127.9 (4)C5—C4—C12—C110.4 (11)
N4—Co1—N1—C12−166.2 (4)N2—C11—C12—N11.2 (9)
N3—Co1—N1—C12−88.6 (4)C7—C11—C12—N1−178.3 (6)
N5—Co1—N1—C1215.5 (19)N2—C11—C12—C4178.6 (6)
N6—Co1—N2—C1075.1 (7)C7—C11—C12—C4−0.9 (10)
N1—Co1—N2—C10175.8 (7)C24—N3—C13—C14−2.1 (11)
N4—Co1—N2—C10−149.6 (11)Co1—N3—C13—C14169.5 (6)
N3—Co1—N2—C10−93.0 (7)N3—C13—C14—C152.8 (13)
N5—Co1—N2—C10−3.2 (7)C13—C14—C15—C16−1.8 (13)
N6—Co1—N2—C11−108.0 (5)C14—C15—C16—C240.4 (12)
N1—Co1—N2—C11−7.3 (5)C14—C15—C16—C17178.6 (8)
N4—Co1—N2—C1127.3 (14)C15—C16—C17—C18−179.3 (9)
N3—Co1—N2—C1183.8 (5)C24—C16—C17—C18−1.1 (13)
N5—Co1—N2—C11173.7 (5)C16—C17—C18—C190.7 (14)
N6—Co1—N3—C13−123.2 (8)C17—C18—C19—C20−179.4 (9)
N2—Co1—N3—C1310.0 (6)C17—C18—C19—C23−1.2 (12)
N1—Co1—N3—C1388.3 (6)C18—C19—C20—C21178.7 (8)
N4—Co1—N3—C13−179.0 (6)C23—C19—C20—C210.5 (11)
N5—Co1—N3—C13−84.2 (6)C19—C20—C21—C22−1.6 (12)
N6—Co1—N3—C2448.9 (9)C23—N4—C22—C210.3 (10)
N2—Co1—N3—C24−177.9 (4)Co1—N4—C22—C21−177.0 (5)
N1—Co1—N3—C24−99.6 (5)C20—C21—C22—N41.3 (12)
N4—Co1—N3—C24−6.9 (4)C22—N4—C23—C19−1.5 (9)
N5—Co1—N3—C2487.8 (5)Co1—N4—C23—C19176.2 (5)
N6—Co1—N4—C2216.2 (6)C22—N4—C23—C24179.2 (6)
N2—Co1—N4—C22−119.2 (12)Co1—N4—C23—C24−3.1 (7)
N1—Co1—N4—C22−85.4 (6)C18—C19—C23—N4−177.2 (7)
N3—Co1—N4—C22−177.2 (6)C20—C19—C23—N41.1 (10)
N5—Co1—N4—C2294.4 (6)C18—C19—C23—C242.2 (10)
N6—Co1—N4—C23−161.2 (4)C20—C19—C23—C24−179.6 (6)
N2—Co1—N4—C2363.4 (13)C13—N3—C24—C160.6 (10)
N1—Co1—N4—C2397.2 (4)Co1—N3—C24—C16−172.2 (5)
N3—Co1—N4—C235.3 (4)C13—N3—C24—C23−179.5 (6)
N5—Co1—N4—C23−83.0 (4)Co1—N3—C24—C237.7 (7)
N6—Co1—N5—C25−179.1 (6)C15—C16—C24—N30.2 (11)
N2—Co1—N5—C25−85.5 (6)C17—C16—C24—N3−178.1 (7)
N1—Co1—N5—C25−93.0 (18)C15—C16—C24—C23−179.7 (7)
N4—Co1—N5—C2588.7 (6)C17—C16—C24—C232.0 (10)
N3—Co1—N5—C2511.3 (6)N4—C23—C24—N3−3.1 (9)
N6—Co1—N5—C360.7 (4)C19—C23—C24—N3177.5 (6)
N2—Co1—N5—C3694.3 (5)N4—C23—C24—C16176.8 (6)
N1—Co1—N5—C3686.8 (17)C19—C23—C24—C16−2.6 (9)
N4—Co1—N5—C36−91.5 (5)C36—N5—C25—C26−1.6 (11)
N3—Co1—N5—C36−168.9 (5)Co1—N5—C25—C26178.1 (6)
N2—Co1—N6—C3488.4 (6)N5—C25—C26—C27−0.4 (13)
N1—Co1—N6—C349.6 (6)C25—C26—C27—C281.9 (13)
N4—Co1—N6—C34−84.2 (6)C26—C27—C28—C36−1.2 (11)
N3—Co1—N6—C34−138.2 (8)C26—C27—C28—C29178.0 (8)
N5—Co1—N6—C34−178.2 (6)C36—C28—C29—C300.5 (11)
N2—Co1—N6—C35−94.8 (5)C27—C28—C29—C30−178.7 (8)
N1—Co1—N6—C35−173.6 (4)C28—C29—C30—C31−1.8 (12)
N4—Co1—N6—C3592.6 (5)C29—C30—C31—C32−178.2 (8)
N3—Co1—N6—C3538.6 (10)C29—C30—C31—C350.2 (12)
N5—Co1—N6—C35−1.4 (4)C35—C31—C32—C33−1.8 (11)
C12—N1—C1—C21.9 (10)C30—C31—C32—C33176.6 (8)
Co1—N1—C1—C2−171.8 (5)C31—C32—C33—C342.6 (12)
N1—C1—C2—C3−2.3 (12)C35—N6—C34—C331.7 (11)
C1—C2—C3—C40.0 (13)Co1—N6—C34—C33178.4 (6)
C2—C3—C4—C122.3 (12)C32—C33—C34—N6−2.6 (13)
C2—C3—C4—C5−178.0 (9)C34—N6—C35—C31−0.8 (10)
C3—C4—C5—C6−179.8 (10)Co1—N6—C35—C31−177.9 (5)
C12—C4—C5—C6−0.2 (14)C34—N6—C35—C36179.0 (6)
C4—C5—C6—C70.4 (17)Co1—N6—C35—C361.9 (7)
C5—C6—C7—C8−178.6 (10)C32—C31—C35—N60.9 (10)
C5—C6—C7—C11−1.0 (16)C30—C31—C35—N6−177.6 (7)
C11—C7—C8—C9−3.0 (14)C32—C31—C35—C36−178.9 (7)
C6—C7—C8—C9174.6 (10)C30—C31—C35—C362.6 (10)
C7—C8—C9—C104.2 (16)C25—N5—C36—C282.3 (10)
C11—N2—C10—C9−1.3 (12)Co1—N5—C36—C28−177.5 (5)
Co1—N2—C10—C9175.5 (7)C25—N5—C36—C35179.9 (6)
C8—C9—C10—N2−2.1 (15)Co1—N5—C36—C350.1 (7)
C10—N2—C11—C72.5 (10)C27—C28—C36—N5−0.9 (10)
Co1—N2—C11—C7−174.7 (5)C29—C28—C36—N5179.8 (7)
C10—N2—C11—C12−177.0 (6)C27—C28—C36—C35−178.5 (6)
Co1—N2—C11—C125.8 (7)C29—C28—C36—C352.2 (10)
C8—C7—C11—N2−0.5 (11)N6—C35—C36—N5−1.4 (9)
C6—C7—C11—N2−178.3 (8)C31—C35—C36—N5178.5 (6)
C8—C7—C11—C12179.0 (7)N6—C35—C36—C28176.3 (6)
C6—C7—C11—C121.2 (12)C31—C35—C36—C28−3.8 (10)
C1—N1—C12—C40.6 (10)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O9—H209···O1i0.85 (10)1.99 (8)2.802 (13)157 (19)
O9—H109···O80.86 (14)2.26 (17)2.953 (17)139 (23)
C15—H15···O9ii0.932.563.271 (14)134
C33—H33···O5iii0.932.513.116 (12)123
C5—H5···O4iv0.932.453.309 (13)154
C33—H33···O5iii0.932.513.116 (12)123

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5497).

References

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