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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): m1499.
Published online 2008 November 8. doi:  10.1107/S1600536808035162
PMCID: PMC2959905

Triazido­[tris­(2-pyridyl-κN)methyl­amine]cobalt(III)

Abstract

The title compound, [Co(N3)3(C16H14N4)], was synthesized by hydro­thermal reaction of [Co(NH3)6](NO3)3, NaN3 and tris­(2-pyrid­yl)methyl­amine. The structure contains two independent complexes in the asymmetric unit, with closely comparable geometry. The CoIII atoms are hexa­coordinated by three N atoms from the tridentate tris­(2-pyrid­yl)methyl­amine ligands and three azide ions in a fac arrangement. N—H(...)N hydrogen bonds are formed between the amino group and the uncoordinated terminal N atoms of the azide ligands.

Related literature

For other complexes containing the tris­(2-pyrid­yl)methyl­amine ligand, see: Arnold et al. (2001 [triangle]). For related CoIII triazide complexes, see: Ma et al. (2000 [triangle]); Chun & Bernal (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1499-scheme1.jpg

Experimental

Crystal data

  • [Co(N3)3(C16H14N4)]
  • M r = 447.33
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1499-efi1.jpg
  • a = 10.2063 (3) Å
  • b = 13.6760 (6) Å
  • c = 14.4735 (2) Å
  • α = 68.150 (3)°
  • β = 77.114 (2)°
  • γ = 80.249 (2)°
  • V = 1819.53 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.98 mm−1
  • T = 295 (2) K
  • 0.20 × 0.14 × 0.12 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.828, T max = 0.892
  • 18878 measured reflections
  • 6655 independent reflections
  • 5825 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.029
  • wR(F 2) = 0.086
  • S = 1.00
  • 6655 reflections
  • 557 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; 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: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035162/bi2307sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035162/bi2307Isup2.hkl

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

Acknowledgments

This work is supported by the Natural Science Foundation of Shandong Province (grant No. Y2007D39).

supplementary crystallographic information

Comment

Pyridine-based ligands have been widely in materials science as ligands that can coordinate to transition-metal or rare-earth cations. The title compound is a CoIII triazide complex with the tridentate tris(2-pyridyl)methylamine ligand.

Experimental

A mixture of hexaamminecobalt(III) nitrate (0.5 mmol), sodium azide (0.5 mmol), tris(2-pyridyl)methylamine (0.5 mmol), H2O (8 ml) and ethanol (8 ml) in a 25 ml Teflon-lined stainless steel autoclave was kept at 433 K for three days. Brown crystals were obtained after cooling to room temperature with a yield of 12 %. Elemental analysis calculated: C 42.92, H 3.13, N 40.69 %; found: C 42.88, H 3.06, N 40.55 %.

Refinement

H atoms bound to C atoms were placed in calculated positions with C—H = 0.93 Å and refined as riding with Uiso(H) = 1.2Ueq(C). The H atoms of the amine groups were located in difference Fourier maps and refined without restraint.

Figures

Fig. 1.
Two molecules in the asymmetric unit of the title compound with displacement ellipsoids shown at 30 % probability for non-H atoms.

Crystal data

[Co(N3)3(C16H14N4)]Z = 4
Mr = 447.33F000 = 912
Triclinic, P1Dx = 1.633 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 10.2063 (3) ÅCell parameters from 6655 reflections
b = 13.6760 (6) Åθ = 1.5–25.5º
c = 14.4735 (2) ŵ = 0.98 mm1
α = 68.150 (3)ºT = 295 (2) K
β = 77.114 (2)ºBlock, brown
γ = 80.249 (2)º0.20 × 0.14 × 0.12 mm
V = 1819.53 (10) Å3

Data collection

Bruker APEXII CCD diffractometer6655 independent reflections
Radiation source: fine-focus sealed tube5825 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.018
T = 295(2) Kθmax = 25.5º
[var phi] and ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −12→12
Tmin = 0.828, Tmax = 0.892k = −16→16
18878 measured reflectionsl = −17→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087  w = 1/[σ2(Fo2) + (0.056P)2 + 0.548P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.033
6655 reflectionsΔρmax = 0.31 e Å3
557 parametersΔρmin = −0.22 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
Co1'0.08066 (2)0.308970 (19)0.810308 (17)0.02644 (8)
Co10.26516 (3)0.20548 (2)0.299922 (19)0.03377 (9)
C10.2380 (3)0.0073 (2)0.46611 (17)0.0542 (6)
H10.28140.03900.49620.065*
C20.1936 (3)−0.0916 (2)0.5212 (2)0.0685 (8)
H20.2090−0.12690.58710.082*
C30.1266 (3)−0.1370 (2)0.4774 (2)0.0690 (8)
H30.0923−0.20190.51460.083*
C40.1102 (3)−0.08588 (18)0.37784 (19)0.0530 (6)
H40.0667−0.11640.34670.064*
C50.1600 (2)0.01205 (16)0.32530 (16)0.0390 (5)
C60.1434 (2)0.07501 (15)0.21526 (15)0.0349 (4)
C70.04845 (18)0.17351 (15)0.21651 (14)0.0313 (4)
C8−0.0757 (2)0.19521 (17)0.18453 (15)0.0404 (5)
H8−0.10400.14880.16130.048*
C9−0.1558 (2)0.28565 (19)0.18759 (17)0.0471 (5)
H9−0.23920.30110.16680.057*
C10−0.1112 (2)0.35281 (18)0.22176 (17)0.0471 (5)
H10−0.16370.41470.22400.056*
C110.0128 (2)0.32761 (16)0.25290 (15)0.0387 (5)
H110.04260.37340.27620.046*
C120.28077 (19)0.11126 (15)0.14989 (15)0.0340 (4)
C130.3317 (2)0.08941 (18)0.06194 (17)0.0454 (5)
H130.28490.05070.04130.054*
C140.4534 (3)0.12597 (19)0.00521 (18)0.0529 (6)
H140.48840.1131−0.05470.064*
C150.5216 (2)0.18087 (19)0.03765 (19)0.0537 (6)
H150.60480.20390.00140.064*
C160.4654 (2)0.20184 (18)0.12520 (17)0.0453 (5)
H160.51090.24070.14660.054*
C1'0.2190 (2)0.11662 (17)0.78384 (17)0.0435 (5)
H1'0.13460.09180.81270.052*
C2'0.3226 (2)0.05019 (19)0.7545 (2)0.0562 (6)
H2'0.3088−0.01850.76350.067*
C3'0.4475 (2)0.0874 (2)0.7115 (2)0.0571 (6)
H3'0.51920.04430.69040.069*
C4'0.4649 (2)0.18962 (18)0.70021 (18)0.0453 (5)
H4'0.54870.21570.67170.054*
C5'0.35712 (18)0.25276 (16)0.73144 (14)0.0317 (4)
C6'0.36740 (17)0.36699 (16)0.71976 (14)0.0312 (4)
C7'0.26982 (18)0.44037 (15)0.65124 (13)0.0292 (4)
C8'0.3112 (2)0.52144 (17)0.56277 (15)0.0404 (5)
H8'0.40200.53300.54160.048*
C9'0.2168 (2)0.58487 (18)0.50625 (16)0.0466 (5)
H9'0.24340.63940.44620.056*
C10'0.0833 (2)0.56725 (17)0.53900 (15)0.0410 (5)
H10'0.01810.61020.50220.049*
C11'0.0474 (2)0.48495 (16)0.62732 (14)0.0341 (4)
H11'−0.04300.47220.64900.041*
C12'0.32219 (18)0.38099 (15)0.82358 (14)0.0306 (4)
C13'0.4033 (2)0.41939 (18)0.86443 (16)0.0428 (5)
H13'0.49060.43440.83110.051*
C14'0.3538 (2)0.4352 (2)0.95506 (18)0.0505 (6)
H14'0.40680.46200.98290.061*
C15'0.2253 (2)0.41100 (18)1.00387 (16)0.0455 (5)
H15'0.19030.42111.06510.055*
C16'0.1495 (2)0.37165 (16)0.96077 (14)0.0370 (4)
H16'0.06290.35450.99410.044*
H4A0.077 (3)0.046 (3)0.116 (3)0.088 (12)*
H4B0.133 (3)−0.039 (2)0.180 (2)0.053 (8)*
H4C0.510 (2)0.463 (2)0.6662 (17)0.041 (6)*
H4D0.556 (3)0.354 (2)0.715 (2)0.054 (8)*
N10.21948 (17)0.05876 (14)0.36963 (13)0.0397 (4)
N20.09126 (15)0.23921 (12)0.25047 (11)0.0311 (3)
N30.34651 (16)0.16761 (13)0.18047 (12)0.0350 (4)
N40.0822 (2)0.01220 (19)0.17793 (18)0.0477 (5)
N50.4350 (2)0.16394 (19)0.34980 (17)0.0590 (5)
N60.4967 (2)0.2294 (2)0.35298 (19)0.0679 (7)
N70.5618 (3)0.2892 (3)0.3565 (3)0.1143 (12)
N80.31082 (19)0.34925 (15)0.22377 (14)0.0442 (4)
N90.30464 (17)0.41107 (15)0.26644 (14)0.0437 (4)
N100.2999 (2)0.47478 (18)0.30208 (18)0.0608 (6)
N110.1681 (2)0.24176 (17)0.41551 (14)0.0497 (5)
N120.2200 (2)0.25807 (19)0.47283 (15)0.0576 (5)
N130.2617 (3)0.2758 (3)0.5315 (2)0.1140 (13)
N1'0.23509 (15)0.21628 (12)0.77228 (12)0.0309 (3)
N2'0.13866 (14)0.42244 (12)0.68322 (11)0.0276 (3)
N3'0.19653 (15)0.35702 (12)0.87168 (11)0.0295 (3)
N4'0.50443 (17)0.39349 (18)0.67291 (15)0.0407 (4)
N5'0.03456 (17)0.19858 (14)0.94046 (13)0.0391 (4)
N6'−0.05808 (16)0.14639 (13)0.96236 (12)0.0347 (4)
N7'−0.1435 (2)0.09138 (17)0.99093 (16)0.0543 (5)
N8'−0.06488 (16)0.40910 (13)0.84197 (13)0.0365 (4)
N9'−0.16651 (16)0.38260 (14)0.90016 (13)0.0382 (4)
N10'−0.2668 (2)0.36471 (19)0.95508 (19)0.0677 (7)
N11'−0.02658 (16)0.26267 (15)0.74183 (13)0.0393 (4)
N12'−0.14505 (16)0.25427 (13)0.76507 (13)0.0356 (4)
N13'−0.25777 (19)0.23998 (19)0.78241 (18)0.0588 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co1'0.02280 (13)0.02834 (15)0.02953 (14)−0.00705 (10)−0.00219 (9)−0.01100 (11)
Co10.03571 (15)0.03377 (16)0.03405 (15)−0.00451 (11)−0.00721 (11)−0.01317 (12)
C10.0648 (15)0.0494 (14)0.0385 (12)0.0027 (12)−0.0097 (10)−0.0072 (11)
C20.0843 (19)0.0540 (16)0.0415 (13)0.0070 (15)−0.0040 (13)0.0027 (12)
C30.085 (2)0.0351 (13)0.0598 (16)−0.0063 (13)0.0103 (14)0.0011 (12)
C40.0591 (14)0.0327 (12)0.0578 (14)−0.0083 (10)0.0051 (11)−0.0124 (11)
C50.0373 (10)0.0291 (10)0.0439 (11)−0.0003 (8)0.0029 (8)−0.0122 (9)
C60.0367 (10)0.0284 (10)0.0399 (10)−0.0074 (8)−0.0007 (8)−0.0140 (8)
C70.0335 (9)0.0297 (10)0.0295 (9)−0.0093 (8)0.0014 (7)−0.0102 (8)
C80.0386 (11)0.0469 (13)0.0390 (11)−0.0096 (9)−0.0050 (8)−0.0175 (10)
C90.0364 (11)0.0547 (14)0.0476 (12)0.0022 (10)−0.0100 (9)−0.0161 (11)
C100.0443 (12)0.0408 (12)0.0500 (12)0.0088 (10)−0.0074 (10)−0.0150 (10)
C110.0452 (11)0.0312 (10)0.0398 (10)−0.0024 (9)−0.0027 (9)−0.0157 (9)
C120.0346 (10)0.0269 (10)0.0379 (10)−0.0005 (8)−0.0024 (8)−0.0117 (8)
C130.0518 (13)0.0403 (12)0.0457 (12)−0.0014 (10)−0.0021 (10)−0.0219 (10)
C140.0590 (14)0.0443 (13)0.0473 (13)−0.0017 (11)0.0119 (11)−0.0201 (11)
C150.0415 (12)0.0458 (13)0.0599 (14)−0.0057 (10)0.0147 (10)−0.0155 (11)
C160.0351 (10)0.0434 (12)0.0553 (13)−0.0087 (9)−0.0005 (9)−0.0169 (10)
C1'0.0404 (11)0.0338 (11)0.0566 (13)−0.0077 (9)−0.0040 (9)−0.0167 (10)
C2'0.0507 (13)0.0350 (12)0.0838 (18)−0.0008 (10)−0.0073 (12)−0.0257 (12)
C3'0.0418 (12)0.0473 (14)0.0804 (17)0.0102 (11)−0.0055 (12)−0.0294 (13)
C4'0.0284 (10)0.0500 (13)0.0571 (13)0.0000 (9)−0.0034 (9)−0.0221 (11)
C5'0.0274 (9)0.0366 (11)0.0323 (9)−0.0027 (8)−0.0065 (7)−0.0129 (8)
C6'0.0229 (8)0.0376 (11)0.0338 (9)−0.0092 (8)0.0004 (7)−0.0136 (8)
C7'0.0295 (9)0.0317 (10)0.0296 (9)−0.0069 (7)−0.0002 (7)−0.0155 (8)
C8'0.0375 (10)0.0395 (12)0.0387 (11)−0.0072 (9)0.0058 (8)−0.0131 (9)
C9'0.0581 (13)0.0367 (12)0.0339 (10)−0.0020 (10)0.0019 (9)−0.0064 (9)
C10'0.0502 (12)0.0374 (11)0.0347 (10)0.0052 (9)−0.0120 (9)−0.0132 (9)
C11'0.0351 (10)0.0372 (11)0.0352 (10)−0.0006 (8)−0.0083 (8)−0.0184 (9)
C12'0.0294 (9)0.0312 (10)0.0317 (9)−0.0070 (8)−0.0065 (7)−0.0092 (8)
C13'0.0360 (10)0.0532 (13)0.0463 (12)−0.0177 (10)−0.0067 (9)−0.0200 (10)
C14'0.0542 (13)0.0613 (15)0.0495 (13)−0.0175 (11)−0.0167 (10)−0.0251 (12)
C15'0.0604 (14)0.0508 (13)0.0315 (10)−0.0156 (11)−0.0070 (9)−0.0175 (10)
C16'0.0419 (11)0.0407 (11)0.0286 (9)−0.0135 (9)−0.0006 (8)−0.0115 (8)
N10.0420 (9)0.0341 (9)0.0351 (9)0.0013 (7)−0.0038 (7)−0.0069 (7)
N20.0336 (8)0.0272 (8)0.0316 (8)−0.0034 (6)−0.0020 (6)−0.0114 (7)
N30.0330 (8)0.0321 (9)0.0385 (9)−0.0029 (7)−0.0029 (7)−0.0128 (7)
N40.0523 (12)0.0377 (11)0.0613 (14)−0.0110 (10)−0.0061 (10)−0.0259 (11)
N50.0521 (12)0.0670 (14)0.0663 (13)0.0004 (11)−0.0281 (10)−0.0250 (11)
N60.0386 (11)0.100 (2)0.0765 (16)−0.0055 (12)−0.0177 (10)−0.0401 (15)
N70.0655 (17)0.139 (3)0.168 (3)−0.0211 (19)−0.043 (2)−0.069 (3)
N80.0550 (11)0.0400 (10)0.0442 (10)−0.0146 (8)−0.0085 (8)−0.0178 (9)
N90.0397 (10)0.0428 (11)0.0520 (11)−0.0139 (8)−0.0090 (8)−0.0154 (9)
N100.0627 (13)0.0567 (13)0.0775 (15)−0.0207 (11)−0.0087 (11)−0.0352 (12)
N110.0538 (11)0.0620 (13)0.0423 (10)−0.0063 (9)−0.0073 (8)−0.0286 (9)
N120.0605 (12)0.0751 (15)0.0439 (11)0.0040 (11)−0.0146 (10)−0.0297 (11)
N130.107 (2)0.188 (4)0.086 (2)0.003 (2)−0.0369 (18)−0.088 (2)
N1'0.0264 (7)0.0304 (8)0.0365 (8)−0.0039 (6)−0.0047 (6)−0.0123 (7)
N2'0.0273 (7)0.0304 (8)0.0282 (7)−0.0045 (6)−0.0034 (6)−0.0138 (6)
N3'0.0302 (8)0.0315 (8)0.0268 (7)−0.0087 (6)−0.0034 (6)−0.0086 (6)
N4'0.0257 (8)0.0520 (12)0.0453 (10)−0.0134 (8)0.0011 (7)−0.0177 (9)
N5'0.0377 (9)0.0398 (10)0.0368 (9)−0.0163 (8)−0.0025 (7)−0.0069 (8)
N6'0.0352 (9)0.0331 (9)0.0335 (8)−0.0065 (8)−0.0016 (7)−0.0102 (7)
N7'0.0510 (11)0.0525 (12)0.0569 (12)−0.0245 (10)−0.0030 (9)−0.0115 (10)
N8'0.0291 (8)0.0353 (9)0.0429 (9)−0.0045 (7)0.0024 (7)−0.0152 (8)
N9'0.0342 (9)0.0373 (10)0.0487 (10)−0.0061 (7)−0.0017 (8)−0.0234 (8)
N10'0.0462 (11)0.0675 (15)0.0875 (16)−0.0213 (11)0.0271 (11)−0.0402 (13)
N11'0.0323 (9)0.0476 (11)0.0482 (10)−0.0111 (8)−0.0065 (7)−0.0255 (8)
N12'0.0356 (9)0.0318 (9)0.0439 (9)−0.0032 (7)−0.0140 (7)−0.0145 (7)
N13'0.0329 (10)0.0718 (15)0.0788 (14)−0.0106 (9)−0.0164 (9)−0.0281 (12)

Geometric parameters (Å, °)

Co1'—N11'1.9408 (17)C1'—H1'0.930
Co1'—N8'1.9407 (16)C2'—C3'1.379 (4)
Co1'—N5'1.9436 (16)C2'—H2'0.930
Co1'—N3'1.9456 (16)C3'—C4'1.383 (3)
Co1'—N2'1.9603 (15)C3'—H3'0.930
Co1'—N1'1.9621 (15)C4'—C5'1.381 (3)
Co1—N111.9335 (18)C4'—H4'0.930
Co1—N81.9406 (18)C5'—N1'1.346 (2)
Co1—N51.941 (2)C5'—C6'1.527 (3)
Co1—N31.9563 (17)C6'—N4'1.454 (2)
Co1—N11.9651 (18)C6'—C7'1.531 (3)
Co1—N21.9796 (16)C6'—C12'1.544 (3)
C1—N11.350 (3)C7'—N2'1.348 (2)
C1—C21.384 (4)C7'—C8'1.381 (3)
C1—H10.930C8'—C9'1.375 (3)
C2—C31.374 (4)C8'—H8'0.930
C2—H20.930C9'—C10'1.370 (3)
C3—C41.382 (4)C9'—H9'0.930
C3—H30.930C10'—C11'1.377 (3)
C4—C51.390 (3)C10'—H10'0.930
C4—H40.930C11'—N2'1.344 (2)
C5—N11.341 (3)C11'—H11'0.930
C5—C61.535 (3)C12'—N3'1.346 (2)
C6—N41.448 (3)C12'—C13'1.381 (3)
C6—C71.524 (3)C13'—C14'1.379 (3)
C6—C121.550 (3)C13'—H13'0.930
C7—N21.341 (3)C14'—C15'1.374 (3)
C7—C81.392 (3)C14'—H14'0.930
C8—C91.372 (3)C15'—C16'1.372 (3)
C8—H80.930C15'—H15'0.930
C9—C101.370 (3)C16'—N3'1.348 (2)
C9—H90.930C16'—H16'0.930
C10—C111.384 (3)N4—H4A0.86 (4)
C10—H100.930N4—H4B0.79 (3)
C11—N21.340 (2)N5—N61.198 (3)
C11—H110.930N6—N71.159 (4)
C12—N31.342 (3)N8—N91.206 (3)
C12—C131.384 (3)N9—N101.156 (3)
C13—C141.385 (3)N11—N121.180 (3)
C13—H130.930N12—N131.145 (3)
C14—C151.361 (4)N4'—H4C0.92 (3)
C14—H140.930N4'—H4D0.86 (3)
C15—C161.381 (3)N5'—N6'1.196 (2)
C15—H150.930N6'—N7'1.152 (2)
C16—N31.346 (3)N8'—N9'1.195 (2)
C16—H160.930N9'—N10'1.147 (2)
C1'—N1'1.344 (3)N11'—N12'1.194 (2)
C1'—C2'1.373 (3)N12'—N13'1.156 (2)
N11'—Co1'—N8'92.84 (7)C3'—C2'—C1'118.7 (2)
N11'—Co1'—N5'94.69 (7)C3'—C2'—H2'120.7
N8'—Co1'—N5'93.10 (7)C1'—C2'—H2'120.7
N11'—Co1'—N3'176.55 (7)C2'—C3'—C4'119.2 (2)
N8'—Co1'—N3'89.23 (7)C2'—C3'—H3'120.4
N5'—Co1'—N3'87.95 (7)C4'—C3'—H3'120.4
N11'—Co1'—N2'89.69 (7)C5'—C4'—C3'119.6 (2)
N8'—Co1'—N2'87.79 (7)C5'—C4'—H4'120.2
N5'—Co1'—N2'175.48 (7)C3'—C4'—H4'120.2
N3'—Co1'—N2'87.63 (6)N1'—C5'—C4'120.82 (19)
N11'—Co1'—N1'88.91 (7)N1'—C5'—C6'116.36 (15)
N8'—Co1'—N1'175.94 (7)C4'—C5'—C6'122.80 (17)
N5'—Co1'—N1'90.40 (7)N4'—C6'—C5'108.89 (16)
N3'—Co1'—N1'88.84 (7)N4'—C6'—C7'109.04 (16)
N2'—Co1'—N1'88.57 (6)C5'—C6'—C7'108.97 (15)
N11—Co1—N892.79 (9)N4'—C6'—C12'113.23 (16)
N11—Co1—N594.33 (9)C5'—C6'—C12'109.64 (15)
N8—Co1—N592.47 (9)C7'—C6'—C12'106.98 (15)
N11—Co1—N3174.49 (8)N2'—C7'—C8'121.22 (17)
N8—Co1—N388.90 (7)N2'—C7'—C6'115.82 (15)
N5—Co1—N390.83 (8)C8'—C7'—C6'122.96 (16)
N11—Co1—N190.12 (8)C9'—C8'—C7'119.35 (19)
N8—Co1—N1176.71 (8)C9'—C8'—H8'120.3
N5—Co1—N188.82 (9)C7'—C8'—H8'120.3
N3—Co1—N188.06 (7)C10'—C9'—C8'119.51 (19)
N11—Co1—N286.79 (7)C10'—C9'—H9'120.2
N8—Co1—N290.55 (7)C8'—C9'—H9'120.2
N5—Co1—N2176.72 (8)C9'—C10'—C11'118.90 (19)
N3—Co1—N287.95 (7)C9'—C10'—H10'120.5
N1—Co1—N288.10 (7)C11'—C10'—H10'120.5
N1—C1—C2121.4 (3)N2'—C11'—C10'122.12 (18)
N1—C1—H1119.3N2'—C11'—H11'118.9
C2—C1—H1119.3C10'—C11'—H11'118.9
C3—C2—C1119.1 (2)N3'—C12'—C13'121.07 (18)
C3—C2—H2120.4N3'—C12'—C6'116.41 (16)
C1—C2—H2120.4C13'—C12'—C6'122.49 (16)
C2—C3—C4119.8 (2)C14'—C13'—C12'119.39 (19)
C2—C3—H3120.1C14'—C13'—H13'120.3
C4—C3—H3120.1C12'—C13'—H13'120.3
C3—C4—C5118.5 (3)C15'—C14'—C13'119.4 (2)
C3—C4—H4120.7C15'—C14'—H14'120.3
C5—C4—H4120.7C13'—C14'—H14'120.3
N1—C5—C4121.7 (2)C16'—C15'—C14'118.86 (19)
N1—C5—C6116.48 (17)C16'—C15'—H15'120.6
C4—C5—C6121.8 (2)C14'—C15'—H15'120.6
N4—C6—C7109.19 (18)N3'—C16'—C15'122.15 (18)
N4—C6—C5109.42 (18)N3'—C16'—H16'118.9
C7—C6—C5106.55 (16)C15'—C16'—H16'118.9
N4—C6—C12113.13 (17)C5—N1—C1119.4 (2)
C7—C6—C12108.01 (15)C5—N1—Co1120.66 (14)
C5—C6—C12110.32 (16)C1—N1—Co1119.71 (17)
N2—C7—C8121.29 (18)C11—N2—C7118.97 (17)
N2—C7—C6116.02 (17)C11—N2—Co1119.98 (14)
C8—C7—C6122.69 (18)C7—N2—Co1121.03 (13)
C9—C8—C7119.5 (2)C16—N3—C12119.15 (18)
C9—C8—H8120.3C16—N3—Co1120.69 (15)
C7—C8—H8120.3C12—N3—Co1120.07 (12)
C10—C9—C8119.0 (2)C6—N4—H4A109 (2)
C10—C9—H9120.5C6—N4—H4B107 (2)
C8—C9—H9120.5H4A—N4—H4B107 (3)
C9—C10—C11119.4 (2)N6—N5—Co1120.19 (19)
C9—C10—H10120.3N7—N6—N5176.7 (3)
C11—C10—H10120.3N9—N8—Co1120.37 (15)
N2—C11—C10121.9 (2)N10—N9—N8176.1 (2)
N2—C11—H11119.0N12—N11—Co1124.36 (17)
C10—C11—H11119.0N13—N12—N11175.3 (3)
N3—C12—C13121.27 (18)C5'—N1'—C1'119.33 (17)
N3—C12—C6117.20 (16)C5'—N1'—Co1'120.43 (13)
C13—C12—C6121.50 (19)C1'—N1'—Co1'120.21 (13)
C14—C13—C12119.0 (2)C11'—N2'—C7'118.88 (16)
C14—C13—H13120.5C11'—N2'—Co1'120.25 (12)
C12—C13—H13120.5C7'—N2'—Co1'120.86 (12)
C15—C14—C13119.6 (2)C12'—N3'—C16'119.08 (16)
C15—C14—H14120.2C12'—N3'—Co1'120.54 (12)
C13—C14—H14120.2C16'—N3'—Co1'120.30 (13)
C14—C15—C16119.1 (2)C6'—N4'—H4C108.3 (14)
C14—C15—H15120.5C6'—N4'—H4D106.8 (17)
C16—C15—H15120.5H4C—N4'—H4D107 (2)
N3—C16—C15121.9 (2)N6'—N5'—Co1'124.28 (14)
N3—C16—H16119.1N7'—N6'—N5'174.3 (2)
C15—C16—H16119.1N9'—N8'—Co1'123.02 (14)
N1'—C1'—C2'122.4 (2)N10'—N9'—N8'175.1 (2)
N1'—C1'—H1'118.8N12'—N11'—Co1'126.01 (14)
C2'—C1'—H1'118.8N13'—N12'—N11'173.6 (2)
N1—C1—C2—C3−1.5 (4)N8—Co1—N2—C11−46.96 (15)
C1—C2—C3—C43.1 (4)N3—Co1—N2—C11−135.84 (15)
C2—C3—C4—C5−1.4 (4)N1—Co1—N2—C11136.03 (15)
C3—C4—C5—N1−2.0 (3)N11—Co1—N2—C7−132.58 (15)
C3—C4—C5—C6−178.7 (2)N8—Co1—N2—C7134.66 (14)
N1—C5—C6—N4178.02 (17)N3—Co1—N2—C745.78 (14)
C4—C5—C6—N4−5.1 (3)N1—Co1—N2—C7−42.35 (14)
N1—C5—C6—C7−64.1 (2)C13—C12—N3—C16−1.1 (3)
C4—C5—C6—C7112.9 (2)C6—C12—N3—C16−179.17 (18)
N1—C5—C6—C1252.9 (2)C13—C12—N3—Co1175.64 (15)
C4—C5—C6—C12−130.1 (2)C6—C12—N3—Co1−2.4 (2)
N4—C6—C7—N2179.37 (17)C15—C16—N3—C120.2 (3)
C5—C6—C7—N261.3 (2)C15—C16—N3—Co1−176.57 (17)
C12—C6—C7—N2−57.2 (2)N8—Co1—N3—C12−133.04 (15)
N4—C6—C7—C8−0.6 (3)N5—Co1—N3—C12134.50 (16)
C5—C6—C7—C8−118.7 (2)N1—Co1—N3—C1245.72 (15)
C12—C6—C7—C8122.74 (19)N2—Co1—N3—C12−42.45 (15)
N2—C7—C8—C90.1 (3)N8—Co1—N3—C1643.67 (17)
C6—C7—C8—C9−179.86 (18)N5—Co1—N3—C16−48.78 (17)
C7—C8—C9—C100.3 (3)N1—Co1—N3—C16−137.57 (16)
C8—C9—C10—C11−0.4 (3)N2—Co1—N3—C16134.27 (16)
C9—C10—C11—N20.1 (3)N11—Co1—N5—N6−70.1 (2)
N4—C6—C12—N3−178.29 (19)N8—Co1—N5—N622.9 (2)
C7—C6—C12—N360.7 (2)N3—Co1—N5—N6111.8 (2)
C5—C6—C12—N3−55.3 (2)N1—Co1—N5—N6−160.2 (2)
N4—C6—C12—C133.7 (3)N11—Co1—N8—N918.42 (18)
C7—C6—C12—C13−117.3 (2)N5—Co1—N8—N9−76.04 (19)
C5—C6—C12—C13126.6 (2)N3—Co1—N8—N9−166.82 (18)
N3—C12—C13—C140.5 (3)N2—Co1—N8—N9105.24 (18)
C6—C12—C13—C14178.5 (2)N8—Co1—N11—N12−74.7 (2)
C12—C13—C14—C151.1 (3)N5—Co1—N11—N1218.0 (2)
C13—C14—C15—C16−2.0 (4)N1—Co1—N11—N12106.8 (2)
C14—C15—C16—N31.4 (4)N2—Co1—N11—N12−165.1 (2)
N1'—C1'—C2'—C3'−0.1 (4)C2'—C1'—N1'—C5'−0.6 (3)
C1'—C2'—C3'—C4'0.6 (4)C2'—C1'—N1'—Co1'177.29 (19)
C2'—C3'—C4'—C5'−0.4 (4)C4'—C5'—N1'—C1'0.9 (3)
C3'—C4'—C5'—N1'−0.4 (3)C6'—C5'—N1'—C1'179.44 (18)
C3'—C4'—C5'—C6'−178.8 (2)C4'—C5'—N1'—Co1'−177.02 (15)
N1'—C5'—C6'—N4'−178.84 (16)C6'—C5'—N1'—Co1'1.5 (2)
C4'—C5'—C6'—N4'−0.3 (3)N11'—Co1'—N1'—C1'−45.45 (16)
N1'—C5'—C6'—C7'−60.0 (2)N5'—Co1'—N1'—C1'49.24 (17)
C4'—C5'—C6'—C7'118.5 (2)N3'—Co1'—N1'—C1'137.18 (16)
N1'—C5'—C6'—C12'56.8 (2)N2'—Co1'—N1'—C1'−135.16 (16)
C4'—C5'—C6'—C12'−124.7 (2)N11'—Co1'—N1'—C5'132.45 (15)
N4'—C6'—C7'—N2'177.58 (16)N5'—Co1'—N1'—C5'−132.86 (15)
C5'—C6'—C7'—N2'58.9 (2)N3'—Co1'—N1'—C5'−44.92 (14)
C12'—C6'—C7'—N2'−59.6 (2)N2'—Co1'—N1'—C5'42.74 (14)
N4'—C6'—C7'—C8'−3.4 (3)C10'—C11'—N2'—C7'−0.6 (3)
C5'—C6'—C7'—C8'−122.16 (19)C10'—C11'—N2'—Co1'178.25 (15)
C12'—C6'—C7'—C8'119.37 (19)C8'—C7'—N2'—C11'0.1 (3)
N2'—C7'—C8'—C9'−0.1 (3)C6'—C7'—N2'—C11'179.11 (16)
C6'—C7'—C8'—C9'−179.01 (19)C8'—C7'—N2'—Co1'−178.76 (15)
C7'—C8'—C9'—C10'0.5 (3)C6'—C7'—N2'—Co1'0.2 (2)
C8'—C9'—C10'—C11'−1.0 (3)N8'—Co1'—N2'—C11'−44.40 (15)
C9'—C10'—C11'—N2'1.1 (3)N11'—Co1'—N2'—C11'48.46 (15)
N4'—C6'—C12'—N3'−179.50 (17)N3'—Co1'—N2'—C11'−133.72 (15)
C5'—C6'—C12'—N3'−57.7 (2)N1'—Co1'—N2'—C11'137.38 (14)
C7'—C6'—C12'—N3'60.4 (2)N8'—Co1'—N2'—C7'134.45 (14)
N4'—C6'—C12'—C13'2.7 (3)N11'—Co1'—N2'—C7'−132.69 (14)
C5'—C6'—C12'—C13'124.5 (2)N3'—Co1'—N2'—C7'45.13 (14)
C7'—C6'—C12'—C13'−117.5 (2)N1'—Co1'—N2'—C7'−43.77 (14)
N3'—C12'—C13'—C14'−1.2 (3)C13'—C12'—N3'—C16'0.5 (3)
C6'—C12'—C13'—C14'176.6 (2)C6'—C12'—N3'—C16'−177.43 (17)
C12'—C13'—C14'—C15'1.0 (4)C13'—C12'—N3'—Co1'177.26 (16)
C13'—C14'—C15'—C16'0.0 (4)C6'—C12'—N3'—Co1'−0.6 (2)
C14'—C15'—C16'—N3'−0.7 (3)C15'—C16'—N3'—C12'0.5 (3)
C4—C5—N1—C13.5 (3)C15'—C16'—N3'—Co1'−176.31 (16)
C6—C5—N1—C1−179.55 (18)N8'—Co1'—N3'—C12'−132.36 (15)
C4—C5—N1—Co1−171.08 (16)N5'—Co1'—N3'—C12'134.51 (15)
C6—C5—N1—Co15.8 (2)N2'—Co1'—N3'—C12'−44.53 (14)
C2—C1—N1—C5−1.8 (3)N1'—Co1'—N3'—C12'44.08 (15)
C2—C1—N1—Co1172.90 (19)N8'—Co1'—N3'—C16'44.41 (15)
N11—Co1—N1—C5126.64 (16)N5'—Co1'—N3'—C16'−48.72 (15)
N5—Co1—N1—C5−139.03 (16)N2'—Co1'—N3'—C16'132.23 (15)
N3—Co1—N1—C5−48.16 (15)N1'—Co1'—N3'—C16'−139.16 (15)
N2—Co1—N1—C539.85 (15)N8'—Co1'—N5'—N6'76.66 (18)
N11—Co1—N1—C1−47.94 (17)N11'—Co1'—N5'—N6'−16.46 (18)
N5—Co1—N1—C146.39 (18)N3'—Co1'—N5'—N6'165.77 (18)
N3—Co1—N1—C1137.25 (17)N1'—Co1'—N5'—N6'−105.40 (18)
N2—Co1—N1—C1−134.73 (17)N11'—Co1'—N8'—N9'67.91 (18)
C10—C11—N2—C70.3 (3)N5'—Co1'—N8'—N9'−26.95 (18)
C10—C11—N2—Co1−178.16 (16)N3'—Co1'—N8'—N9'−114.85 (18)
C8—C7—N2—C11−0.4 (3)N2'—Co1'—N8'—N9'157.49 (18)
C6—C7—N2—C11179.59 (16)N8'—Co1'—N11'—N12'−35.41 (19)
C8—C7—N2—Co1178.01 (14)N5'—Co1'—N11'—N12'57.94 (19)
C6—C7—N2—Co1−2.0 (2)N2'—Co1'—N11'—N12'−123.19 (18)
N11—Co1—N2—C1145.80 (15)N1'—Co1'—N11'—N12'148.24 (19)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4A···N6'i0.86 (4)2.68 (4)3.463 (3)154 (3)
N4—H4A···N5'i0.86 (4)2.69 (4)3.514 (3)163 (3)
N4'—H4C···N10ii0.92 (3)2.44 (2)3.065 (3)124.7 (18)
N4'—H4D···N13'iii0.86 (3)2.38 (3)3.213 (3)162 (2)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2307).

References

  • Arnold, P. J., Davies, S. C., Dilworth, J. R., Durrant, M. C., Griffiths, D. V., Hughes, D. L., Richards, R. L. & Sharpe, P. C. (2001). J. Chem. Soc. Dalton Trans pp. 736–746.
  • Bruker (2001). SADABS and SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2004). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chun, H. & Bernal, I. (2000). Acta Cryst. C56, 1326–1329. [PubMed]
  • Ma, D.-Q., Hikichi, S., Akita, M. & Morooka, Y. (2000). J. Chem. Soc. Dalton Trans pp. 1123–1134.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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