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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Jun 11;67(Pt 7):m866. doi: 10.1107/S1600536811020976

Bis[bis­(3,5-dimethyl-1H-pyrazol-1-yl)­borato]cobalt(II)

Moayad Hossaini Sadr a,*, Behzad Soltani a, James T Engle b, Christopher J Ziegler b, M Taheri a
PMCID: PMC3151970  PMID: 21836863

Abstract

The asymmetric unit of the title compound, [Co(C10H16BN4)2], comprises one unit of the complex. The geometry around the CoII ion is a distorted tetra­hedron. The dihedral angles between the pyrazole rings in the two ligands are 47.19 (15) and 47.20 (16)°, while that between the coordination planes is 79.77 (7)°.

Related literature

For standard values of bond lengths, see: Allen et al. (1987 ▶). For background on pyrazolates and their complexes, see, for example; Trofimenko (1967 ▶); Trofimenko (1999 ▶); Trofimenko (2004 ▶); Sadr et al. (2008 ▶); Ruman et al. (2003 ▶); Krzystek et al. (2010 ▶).graphic file with name e-67-0m866-scheme1.jpg

Experimental

Crystal data

  • [Co(C10H16BN4)2]

  • M r = 465.09

  • Monoclinic, Inline graphic

  • a = 8.351 (5) Å

  • b = 14.012 (9) Å

  • c = 19.833 (13) Å

  • β = 93.281 (7)°

  • V = 2317 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.77 mm−1

  • T = 100 K

  • 0.25 × 0.15 × 0.12 mm

Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2005 ▶) T min = 0.832, T max = 0.914

  • 18648 measured reflections

  • 5048 independent reflections

  • 3947 reflections with I > 2σ(I)

  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050

  • wR(F 2) = 0.122

  • S = 1.04

  • 5048 reflections

  • 288 parameters

  • H-atom parameters constrained

  • Δρmax = 0.60 e Å−3

  • Δρmin = −0.61 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020976/bg2405sup1.cif

e-67-0m866-sup1.cif (25KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020976/bg2405Isup2.hkl

e-67-0m866-Isup2.hkl (247.2KB, hkl)

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

Acknowledgments

This research has been supported by a research fund (No. 403/313) from Aza­rbaijan University of Tarbiat Moallem (MHS and BS). CJZ and JTE thank the University of Akron for providing the X-ray facility.

supplementary crystallographic information

Comment

During the last 40 years anionic polypyrazolylborate ligands (or Trofimeko's scorpionates) have proven to be popular and versatile ligands, binding to a wide variety of transition-metal ions (Trofimenko, 1967; Trofimenko, 1999; Trofimenko, 2004). In addition to variation of the coordinated metal ion or replacing H atoms bonded to a B centre by alkyl moieties, variation of type and number of substituents on the pyrazolyl rings allows for the synthesis of a large number of scorpionate complexes (Ruman et al., 2003; Krzystek et al., 2010). Cobalt complexes with bis pyrazolylborate ligands are of inherent interest in terms of understanding the electronic structure of CoII as a function of coordination environment, even though, CoII complexes themselves are of specific, biological interest as models for the active sites of many metalloproteins. In continuation of our work on the synthesis and structure of pyrazolate complexes (Sadr et al., 2008), we determined the crystal structure of the title compound, [Co(C10 H16 B N4)2] (1).

The asymmetric unit of (1) (Fig. 1), comprises one unit of the complex. The bond lengths and angles are within the normal ranges (Allen, et al., 1987). The geometry around CoII is a distorted tetrahedron defined by N1, N4, N5, and N8 in the coordinated pyrazolate ligands. (Co-N, N-Co-N' ranges: 1.990 (2)-1.996 (2)Å and 97.03 (9)-137.03 (10)°, respectively ). The dihedral angle between the coordination planes (N1–Co1–N4 and N5–Co1–N8) is 79.77 (7)°, and the ones between the pyrazolate rings in each ligand are 47.19 (15) and 47.20 (16)°.

The structure does not present any kind of H-bonding interactions.

Experimental

Tetrahydrofurane (25 ml) solution of potassium pyrazolborate (2 mmol, 0.48 g) was added into the stock water solution of Co(NO3)2,6H2O (50 ml, 0.1 M). The reaction mixture was stirred for 3 h and the resulting product was extracted with CH2Cl2 (50 ml). The organic phase was washed twice with water (100 ml) and CH2Cl2 was removed on a rotary evaporator. The solid residue was dissolved in THF and left for crystallization from THF/n-Hexane (3/1) mixture at ambient temperature by slow evaporation. After 3 days, block purple crystals were collected. Single crystals suitable for X-ray diffraction analysis were obtained after 4 days.

Refinement

All hydrogen atoms were positioned geometrically with C–H = 0.95–0.98 Åand included in a riding model approximation with Uiso (H) = 1.2 or 1.5 Ueq (C), except the B-bound H atoms which were located from the difference Fourier map and constrained to refine with the parent atom with Uiso (H) = 1.2 Ueq (B). A rotating model were applied to the methyl groups.

Figures

Fig. 1.

Fig. 1.

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The ORTEP plot of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering. The H atoms were omitted for clarity.

Crystal data

[Co(C10H16BN4)2] F(000) = 980
Mr = 465.09 Dx = 1.333 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 5094 reflections
a = 8.351 (5) Å θ = 2.5–28.1°
b = 14.012 (9) Å µ = 0.77 mm−1
c = 19.833 (13) Å T = 100 K
β = 93.281 (7)° Block, purple
V = 2317 (3) Å3 0.25 × 0.15 × 0.12 mm
Z = 4
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Data collection

Bruker APEXII CCD diffractometer 5048 independent reflections
Radiation source: fine-focus sealed tube 3947 reflections with I > 2σ(I)
graphite Rint = 0.046
φ and ω scans θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) h = −10→10
Tmin = 0.832, Tmax = 0.914 k = −17→17
18648 measured reflections l = −25→24
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122 H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0516P)2 + 2.3676P] where P = (Fo2 + 2Fc2)/3
5048 reflections (Δ/σ)max < 0.001
288 parameters Δρmax = 0.60 e Å−3
0 restraints Δρmin = −0.61 e Å−3
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Special details

Experimental. 'Ratio of minimum to maximum apparent transmission: 0.1661'
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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Co1 0.10933 (4) 0.19693 (2) 0.197855 (17) 0.01815 (12)
N1 0.1543 (3) 0.15049 (15) 0.34192 (11) 0.0192 (5)
N2 0.0445 (3) 0.15101 (15) 0.28722 (11) 0.0193 (5)
N3 0.3688 (2) 0.25721 (15) 0.29484 (10) 0.0172 (5)
N4 0.2967 (3) 0.27492 (16) 0.23208 (11) 0.0192 (5)
N5 −0.0682 (3) 0.28065 (15) 0.16145 (11) 0.0194 (5)
N6 −0.1491 (3) 0.25825 (16) 0.10128 (11) 0.0196 (5)
N7 0.0520 (3) 0.14005 (16) 0.05685 (11) 0.0211 (5)
N8 0.1649 (3) 0.13899 (16) 0.11056 (11) 0.0201 (5)
C1 0.1616 (4) 0.1256 (2) 0.46705 (14) 0.0293 (7)
H1A 0.2306 0.0690 0.4695 0.044*
H1B 0.0816 0.1208 0.5012 0.044*
H1C 0.2270 0.1829 0.4755 0.044*
C2 0.0784 (3) 0.13186 (19) 0.39839 (14) 0.0219 (6)
C3 −0.0833 (3) 0.1208 (2) 0.38042 (14) 0.0242 (6)
H3 −0.1662 0.1071 0.4098 0.029*
C4 −0.1002 (3) 0.13375 (19) 0.31117 (14) 0.0228 (6)
C5 −0.2482 (3) 0.1303 (2) 0.26574 (15) 0.0274 (6)
H5A −0.2726 0.1944 0.2483 0.041*
H5B −0.3379 0.1072 0.2910 0.041*
H5C −0.2315 0.0870 0.2280 0.041*
C6 0.5782 (3) 0.3276 (2) 0.37451 (14) 0.0246 (6)
H6A 0.5128 0.3126 0.4126 0.037*
H6B 0.6262 0.3910 0.3811 0.037*
H6C 0.6634 0.2798 0.3718 0.037*
C7 0.4748 (3) 0.32668 (18) 0.31042 (13) 0.0191 (5)
C8 0.4721 (3) 0.39084 (19) 0.25731 (13) 0.0206 (6)
H8 0.5346 0.4471 0.2543 0.025*
C9 0.3593 (3) 0.35616 (18) 0.20939 (13) 0.0195 (5)
C10 0.3077 (3) 0.3951 (2) 0.14138 (14) 0.0251 (6)
H10A 0.3101 0.3441 0.1077 0.038*
H10B 0.3808 0.4464 0.1295 0.038*
H10C 0.1985 0.4204 0.1424 0.038*
C11 −0.0646 (3) 0.4077 (2) 0.24764 (14) 0.0261 (6)
H11A −0.0821 0.3625 0.2842 0.039*
H11B −0.1234 0.4669 0.2554 0.039*
H11C 0.0502 0.4217 0.2465 0.039*
C12 −0.1234 (3) 0.36511 (18) 0.18175 (13) 0.0204 (6)
C13 −0.2387 (3) 0.39813 (19) 0.13439 (13) 0.0210 (6)
H13 −0.2965 0.4564 0.1357 0.025*
C14 −0.2524 (3) 0.32872 (19) 0.08469 (13) 0.0201 (5)
C15 −0.3648 (3) 0.3250 (2) 0.02312 (14) 0.0260 (6)
H15A −0.3068 0.3027 −0.0155 0.039*
H15B −0.4081 0.3889 0.0135 0.039*
H15C −0.4529 0.2810 0.0310 0.039*
C16 0.0339 (4) 0.1101 (2) −0.06737 (14) 0.0282 (6)
H16A −0.0476 0.0599 −0.0666 0.042*
H16B 0.1094 0.0952 −0.1019 0.042*
H16C −0.0181 0.1715 −0.0779 0.042*
C17 0.1225 (3) 0.11597 (19) 0.00018 (14) 0.0225 (6)
C18 0.2834 (3) 0.09960 (19) 0.01625 (14) 0.0248 (6)
H18 0.3625 0.0813 −0.0138 0.030*
C19 0.3061 (3) 0.11533 (19) 0.08547 (14) 0.0221 (6)
C20 0.4570 (3) 0.1113 (2) 0.12963 (15) 0.0282 (6)
H20A 0.5029 0.1755 0.1342 0.042*
H20B 0.5340 0.0688 0.1093 0.042*
H20C 0.4329 0.0871 0.1743 0.042*
B1 0.3357 (3) 0.1598 (2) 0.32884 (16) 0.0201 (6)
H1D 0.3987 0.1553 0.3713 0.024*
H1E 0.3674 0.1081 0.2999 0.024*
B2 −0.1278 (4) 0.1565 (2) 0.07122 (17) 0.0237 (7)
H2A −0.1621 0.1089 0.1028 0.028*
H2B −0.1937 0.1503 0.0296 0.028*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Co1 0.01670 (19) 0.01856 (19) 0.01875 (19) −0.00036 (14) −0.00268 (13) −0.00079 (15)
N1 0.0196 (12) 0.0180 (11) 0.0196 (11) 0.0006 (9) −0.0028 (9) −0.0001 (9)
N2 0.0178 (11) 0.0188 (11) 0.0208 (11) −0.0011 (9) −0.0026 (9) −0.0018 (9)
N3 0.0166 (11) 0.0174 (11) 0.0171 (11) −0.0004 (8) −0.0039 (9) 0.0019 (8)
N4 0.0178 (11) 0.0210 (11) 0.0183 (11) −0.0002 (9) −0.0035 (9) 0.0024 (9)
N5 0.0185 (11) 0.0190 (11) 0.0200 (11) −0.0002 (9) −0.0052 (9) −0.0024 (9)
N6 0.0178 (12) 0.0201 (11) 0.0201 (11) 0.0012 (9) −0.0040 (9) −0.0023 (9)
N7 0.0217 (12) 0.0207 (12) 0.0203 (12) 0.0013 (9) −0.0026 (9) −0.0016 (9)
N8 0.0189 (11) 0.0208 (12) 0.0203 (11) 0.0003 (9) −0.0026 (9) −0.0009 (9)
C1 0.0339 (17) 0.0305 (16) 0.0232 (15) −0.0030 (13) −0.0002 (12) 0.0009 (12)
C2 0.0250 (14) 0.0173 (13) 0.0236 (14) −0.0013 (11) 0.0034 (11) −0.0012 (11)
C3 0.0229 (14) 0.0239 (14) 0.0265 (15) −0.0034 (11) 0.0063 (11) −0.0025 (12)
C4 0.0205 (14) 0.0184 (13) 0.0296 (15) −0.0008 (11) 0.0030 (11) −0.0027 (11)
C5 0.0161 (14) 0.0346 (16) 0.0315 (16) −0.0024 (12) 0.0001 (11) −0.0056 (13)
C6 0.0260 (15) 0.0248 (15) 0.0223 (14) −0.0041 (11) −0.0053 (11) −0.0017 (11)
C7 0.0171 (13) 0.0185 (13) 0.0213 (13) 0.0010 (10) −0.0016 (10) −0.0013 (10)
C8 0.0209 (14) 0.0179 (13) 0.0229 (14) −0.0027 (10) 0.0007 (11) 0.0008 (11)
C9 0.0196 (13) 0.0185 (13) 0.0205 (13) 0.0022 (10) 0.0019 (10) 0.0018 (10)
C10 0.0267 (15) 0.0263 (15) 0.0222 (14) −0.0008 (11) −0.0004 (11) 0.0046 (11)
C11 0.0287 (16) 0.0251 (15) 0.0241 (15) −0.0003 (12) −0.0012 (12) −0.0043 (11)
C12 0.0208 (14) 0.0174 (13) 0.0230 (14) −0.0015 (10) 0.0024 (11) −0.0003 (10)
C13 0.0206 (14) 0.0195 (13) 0.0231 (14) 0.0029 (10) 0.0019 (11) 0.0022 (11)
C14 0.0186 (13) 0.0230 (14) 0.0187 (13) 0.0005 (10) 0.0020 (10) 0.0016 (10)
C15 0.0254 (15) 0.0299 (16) 0.0223 (14) 0.0035 (12) −0.0038 (11) −0.0006 (12)
C16 0.0355 (17) 0.0268 (15) 0.0218 (15) 0.0062 (13) −0.0035 (12) −0.0017 (12)
C17 0.0278 (15) 0.0172 (13) 0.0224 (14) 0.0013 (11) 0.0009 (11) −0.0008 (11)
C18 0.0269 (15) 0.0218 (14) 0.0261 (15) 0.0035 (11) 0.0056 (11) 0.0017 (11)
C19 0.0212 (14) 0.0187 (13) 0.0265 (15) 0.0025 (10) 0.0028 (11) 0.0028 (11)
C20 0.0207 (15) 0.0330 (16) 0.0308 (16) 0.0017 (12) −0.0001 (12) 0.0024 (13)
B1 0.0171 (15) 0.0193 (15) 0.0233 (15) −0.0001 (11) −0.0021 (11) 0.0039 (12)
B2 0.0194 (16) 0.0215 (15) 0.0296 (17) −0.0016 (12) −0.0029 (12) −0.0053 (13)
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Geometric parameters (Å, °)

Co1—N2 1.990 (2) C6—H6C 0.9800
Co1—N8 1.991 (2) C7—C8 1.384 (4)
Co1—N5 1.993 (2) C8—C9 1.387 (4)
Co1—N4 1.996 (2) C8—H8 0.9500
N1—C2 1.344 (3) C9—C10 1.495 (4)
N1—N2 1.380 (3) C10—H10A 0.9800
N1—B1 1.557 (4) C10—H10B 0.9800
N2—C4 1.345 (3) C10—H10C 0.9800
N3—C7 1.340 (3) C11—C12 1.494 (4)
N3—N4 1.374 (3) C11—H11A 0.9800
N3—B1 1.554 (4) C11—H11B 0.9800
N4—C9 1.341 (3) C11—H11C 0.9800
N5—C12 1.340 (3) C12—C13 1.385 (4)
N5—N6 1.374 (3) C13—C14 1.385 (4)
N6—C14 1.340 (3) C13—H13 0.9500
N6—B2 1.560 (4) C14—C15 1.498 (4)
N7—C17 1.341 (3) C15—H15A 0.9800
N7—N8 1.381 (3) C15—H15B 0.9800
N7—B2 1.561 (4) C15—H15C 0.9800
N8—C19 1.347 (3) C16—C17 1.495 (4)
C1—C2 1.496 (4) C16—H16A 0.9800
C1—H1A 0.9800 C16—H16B 0.9800
C1—H1B 0.9800 C16—H16C 0.9800
C1—H1C 0.9800 C17—C18 1.382 (4)
C2—C3 1.385 (4) C18—C19 1.393 (4)
C3—C4 1.385 (4) C18—H18 0.9500
C3—H3 0.9500 C19—C20 1.494 (4)
C4—C5 1.488 (4) C20—H20A 0.9800
C5—H5A 0.9800 C20—H20B 0.9800
C5—H5B 0.9800 C20—H20C 0.9800
C5—H5C 0.9800 B1—H1D 0.9691
C6—C7 1.495 (4) B1—H1E 0.9704
C6—H6A 0.9800 B2—H2A 0.9695
C6—H6B 0.9800 B2—H2B 0.9693
N2—Co1—N8 137.03 (10) N4—C9—C8 109.3 (2)
N2—Co1—N5 106.14 (10) N4—C9—C10 121.0 (2)
N8—Co1—N5 97.50 (10) C8—C9—C10 129.8 (2)
N2—Co1—N4 97.03 (9) C9—C10—H10A 109.5
N8—Co1—N4 107.57 (10) C9—C10—H10B 109.5
N5—Co1—N4 110.71 (10) H10A—C10—H10B 109.5
C2—N1—N2 109.4 (2) C9—C10—H10C 109.5
C2—N1—B1 131.7 (2) H10A—C10—H10C 109.5
N2—N1—B1 118.5 (2) H10B—C10—H10C 109.5
C4—N2—N1 106.9 (2) C12—C11—H11A 109.5
C4—N2—Co1 131.96 (19) C12—C11—H11B 109.5
N1—N2—Co1 119.96 (17) H11A—C11—H11B 109.5
C7—N3—N4 109.1 (2) C12—C11—H11C 109.5
C7—N3—B1 132.0 (2) H11A—C11—H11C 109.5
N4—N3—B1 118.2 (2) H11B—C11—H11C 109.5
C9—N4—N3 107.4 (2) N5—C12—C13 109.2 (2)
C9—N4—Co1 131.58 (18) N5—C12—C11 120.9 (2)
N3—N4—Co1 120.24 (16) C13—C12—C11 129.8 (2)
C12—N5—N6 107.6 (2) C14—C13—C12 105.9 (2)
C12—N5—Co1 132.25 (18) C14—C13—H13 127.0
N6—N5—Co1 119.92 (16) C12—C13—H13 127.0
C14—N6—N5 108.8 (2) N6—C14—C13 108.5 (2)
C14—N6—B2 131.8 (2) N6—C14—C15 122.6 (2)
N5—N6—B2 118.7 (2) C13—C14—C15 128.8 (2)
C17—N7—N8 109.3 (2) C14—C15—H15A 109.5
C17—N7—B2 131.5 (2) C14—C15—H15B 109.5
N8—N7—B2 118.8 (2) H15A—C15—H15B 109.5
C19—N8—N7 106.9 (2) C14—C15—H15C 109.5
C19—N8—Co1 132.37 (19) H15A—C15—H15C 109.5
N7—N8—Co1 118.93 (17) H15B—C15—H15C 109.5
C2—C1—H1A 109.5 C17—C16—H16A 109.5
C2—C1—H1B 109.5 C17—C16—H16B 109.5
H1A—C1—H1B 109.5 H16A—C16—H16B 109.5
C2—C1—H1C 109.5 C17—C16—H16C 109.5
H1A—C1—H1C 109.5 H16A—C16—H16C 109.5
H1B—C1—H1C 109.5 H16B—C16—H16C 109.5
N1—C2—C3 107.9 (2) N7—C17—C18 108.4 (2)
N1—C2—C1 123.6 (3) N7—C17—C16 123.1 (3)
C3—C2—C1 128.5 (3) C18—C17—C16 128.5 (3)
C4—C3—C2 106.5 (2) C17—C18—C19 106.0 (2)
C4—C3—H3 126.8 C17—C18—H18 127.0
C2—C3—H3 126.8 C19—C18—H18 127.0
N2—C4—C3 109.3 (2) N8—C19—C18 109.3 (2)
N2—C4—C5 121.6 (3) N8—C19—C20 121.3 (2)
C3—C4—C5 129.1 (3) C18—C19—C20 129.4 (3)
C4—C5—H5A 109.5 C19—C20—H20A 109.5
C4—C5—H5B 109.5 C19—C20—H20B 109.5
H5A—C5—H5B 109.5 H20A—C20—H20B 109.5
C4—C5—H5C 109.5 C19—C20—H20C 109.5
H5A—C5—H5C 109.5 H20A—C20—H20C 109.5
H5B—C5—H5C 109.5 H20B—C20—H20C 109.5
C7—C6—H6A 109.5 N3—B1—N1 110.2 (2)
C7—C6—H6B 109.5 N3—B1—H1D 109.4
H6A—C6—H6B 109.5 N1—B1—H1D 109.6
C7—C6—H6C 109.5 N3—B1—H1E 109.7
H6A—C6—H6C 109.5 N1—B1—H1E 109.7
H6B—C6—H6C 109.5 H1D—B1—H1E 108.2
N3—C7—C8 108.3 (2) N6—B2—N7 109.7 (2)
N3—C7—C6 123.0 (2) N6—B2—H2A 109.7
C8—C7—C6 128.7 (2) N7—B2—H2A 109.8
C7—C8—C9 106.0 (2) N6—B2—H2B 109.6
C7—C8—H8 127.0 N7—B2—H2B 109.7
C9—C8—H8 127.0 H2A—B2—H2B 108.3
C2—N1—N2—C4 0.8 (3) N1—N2—C4—C5 179.3 (2)
B1—N1—N2—C4 174.7 (2) Co1—N2—C4—C5 11.9 (4)
C2—N1—N2—Co1 170.05 (17) C2—C3—C4—N2 0.6 (3)
B1—N1—N2—Co1 −16.1 (3) C2—C3—C4—C5 −179.6 (3)
N8—Co1—N2—C4 −90.4 (3) N4—N3—C7—C8 0.1 (3)
N5—Co1—N2—C4 30.3 (3) B1—N3—C7—C8 170.1 (3)
N4—Co1—N2—C4 144.3 (2) N4—N3—C7—C6 −178.0 (2)
N8—Co1—N2—N1 103.6 (2) B1—N3—C7—C6 −8.0 (4)
N5—Co1—N2—N1 −135.75 (18) N3—C7—C8—C9 0.0 (3)
N4—Co1—N2—N1 −21.76 (19) C6—C7—C8—C9 178.0 (3)
C7—N3—N4—C9 −0.2 (3) N3—N4—C9—C8 0.2 (3)
B1—N3—N4—C9 −171.7 (2) Co1—N4—C9—C8 169.59 (19)
C7—N3—N4—Co1 −171.03 (17) N3—N4—C9—C10 179.1 (2)
B1—N3—N4—Co1 17.4 (3) Co1—N4—C9—C10 −11.5 (4)
N2—Co1—N4—C9 −147.1 (2) C7—C8—C9—N4 −0.1 (3)
N8—Co1—N4—C9 68.6 (3) C7—C8—C9—C10 −178.9 (3)
N5—Co1—N4—C9 −36.9 (3) N6—N5—C12—C13 −0.7 (3)
N2—Co1—N4—N3 21.2 (2) Co1—N5—C12—C13 173.49 (19)
N8—Co1—N4—N3 −123.16 (19) N6—N5—C12—C11 177.2 (2)
N5—Co1—N4—N3 131.42 (18) Co1—N5—C12—C11 −8.6 (4)
N2—Co1—N5—C12 66.4 (3) N5—C12—C13—C14 0.8 (3)
N8—Co1—N5—C12 −149.9 (2) C11—C12—C13—C14 −176.8 (3)
N4—Co1—N5—C12 −37.8 (3) N5—N6—C14—C13 0.2 (3)
N2—Co1—N5—N6 −119.98 (19) B2—N6—C14—C13 169.9 (3)
N8—Co1—N5—N6 23.8 (2) N5—N6—C14—C15 −177.4 (2)
N4—Co1—N5—N6 135.80 (18) B2—N6—C14—C15 −7.7 (4)
C12—N5—N6—C14 0.3 (3) C12—C13—C14—N6 −0.6 (3)
Co1—N5—N6—C14 −174.73 (17) C12—C13—C14—C15 176.8 (3)
C12—N5—N6—B2 −170.9 (2) N8—N7—C17—C18 −0.5 (3)
Co1—N5—N6—B2 14.0 (3) B2—N7—C17—C18 −173.1 (3)
C17—N7—N8—C19 1.0 (3) N8—N7—C17—C16 180.0 (2)
B2—N7—N8—C19 174.6 (2) B2—N7—C17—C16 7.4 (5)
C17—N7—N8—Co1 167.53 (18) N7—C17—C18—C19 −0.1 (3)
B2—N7—N8—Co1 −18.8 (3) C16—C17—C18—C19 179.4 (3)
N2—Co1—N8—C19 −95.1 (3) N7—N8—C19—C18 −1.1 (3)
N5—Co1—N8—C19 141.3 (2) Co1—N8—C19—C18 −165.08 (19)
N4—Co1—N8—C19 26.8 (3) N7—N8—C19—C20 177.5 (2)
N2—Co1—N8—N7 102.4 (2) Co1—N8—C19—C20 13.5 (4)
N5—Co1—N8—N7 −21.16 (19) C17—C18—C19—N8 0.8 (3)
N4—Co1—N8—N7 −135.73 (18) C17—C18—C19—C20 −177.6 (3)
N2—N1—C2—C3 −0.5 (3) C7—N3—B1—N1 127.9 (3)
B1—N1—C2—C3 −173.3 (3) N4—N3—B1—N1 −62.9 (3)
N2—N1—C2—C1 179.7 (2) C2—N1—B1—N3 −125.5 (3)
B1—N1—C2—C1 7.0 (4) N2—N1—B1—N3 62.3 (3)
N1—C2—C3—C4 −0.1 (3) C14—N6—B2—N7 130.1 (3)
C1—C2—C3—C4 179.7 (3) N5—N6—B2—N7 −61.1 (3)
N1—N2—C4—C3 −0.9 (3) C17—N7—B2—N6 −123.8 (3)
Co1—N2—C4—C3 −168.27 (19) N8—N7—B2—N6 64.2 (3)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2405).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020976/bg2405sup1.cif

e-67-0m866-sup1.cif (25KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020976/bg2405Isup2.hkl

e-67-0m866-Isup2.hkl (247.2KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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