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

Hao, L.; Liu, X.

doi:10.1107/S1600536808035162

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1499

doi:10.1107/S1600536808035162

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

Lujiang Hao ^a ^* and Xia Liu ^b

^aCollege of Food and Biological Engineering, Shandong Institute of Light Industry, Jinan 250353, People's Republic of China, and ^bMaize Research Institute, Shandong Academy of Agricultural Science, Jinan 250100, People's Republic of China
^*Correspondence e-mail: lujianghao001@yahoo.com.cn

(Received 29 September 2008; accepted 28 October 2008; online 8 November 2008)

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 Co^III 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 ). For related Co^III triazide complexes, see: Ma et al. (2000 ); Chun & Bernal (2000 ).

Experimental

Crystal data

[Co(N₃)₃(C₁₆H₁₄N₄)]
M_r = 447.33
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.086
S = 1.00
6655 reflections
557 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯N6′ⁱ	0.86 (4)	2.68 (4)	3.463 (3)	154 (3)
N4—H4A⋯N5′ⁱ	0.86 (4)	2.69 (4)	3.514 (3)	163 (3)
N4′—H4C⋯N10ⁱⁱ	0.92 (3)	2.44 (2)	3.065 (3)	124.7 (18)
N4′—H4D⋯N13′ⁱⁱⁱ	0.86 (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.

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

Supporting information

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

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

checkCIF report

Comment top

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 Co^III triazide complex with the tridentate tris(2-pyridyl)methylamine ligand.

Related literature top

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

Experimental top

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 %.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

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

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

Crystal data top

[Co(N₃)₃(C₁₆H₁₄N₄)]	Z = 4
M_r = 447.33	F(000) = 912
Triclinic, P1	D_x = 1.633 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2063 (3) Å	Cell parameters from 6655 reflections
b = 13.6760 (6) Å	θ = 1.5–25.5°
c = 14.4735 (2) Å	µ = 0.98 mm⁻¹
α = 68.150 (3)°	T = 295 K
β = 77.114 (2)°	Block, brown
γ = 80.249 (2)°	0.20 × 0.14 × 0.12 mm
V = 1819.53 (10) Å³

Data collection top

Bruker APEXII CCD diffractometer	6655 independent reflections
Radiation source: fine-focus sealed tube	5825 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
T_min = 0.828, T_max = 0.892	k = −16→16
18878 measured reflections	l = −17→17

Refinement top

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.056P)² + 0.548P] where P = (F_o² + 2F_c²)/3
6655 reflections	(Δ/σ)_max = 0.033
557 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

[Co(N₃)₃(C₁₆H₁₄N₄)]	γ = 80.249 (2)°
M_r = 447.33	V = 1819.53 (10) Å³
Triclinic, P1	Z = 4
a = 10.2063 (3) Å	Mo Kα radiation
b = 13.6760 (6) Å	µ = 0.98 mm⁻¹
c = 14.4735 (2) Å	T = 295 K
α = 68.150 (3)°	0.20 × 0.14 × 0.12 mm
β = 77.114 (2)°

Data collection top

Bruker APEXII CCD diffractometer	6655 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	5825 reflections with I > 2σ(I)
T_min = 0.828, T_max = 0.892	R_int = 0.018
18878 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.31 e Å⁻³
6655 reflections	Δρ_min = −0.22 e Å⁻³
557 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
Co1'	0.08066 (2)	0.308970 (19)	0.810308 (17)	0.02644 (8)
Co1	0.26516 (3)	0.20548 (2)	0.299922 (19)	0.03377 (9)
C1	0.2380 (3)	0.0073 (2)	0.46611 (17)	0.0542 (6)
H1	0.2814	0.0390	0.4962	0.065*
C2	0.1936 (3)	−0.0916 (2)	0.5212 (2)	0.0685 (8)
H2	0.2090	−0.1269	0.5871	0.082*
C3	0.1266 (3)	−0.1370 (2)	0.4774 (2)	0.0690 (8)
H3	0.0923	−0.2019	0.5146	0.083*
C4	0.1102 (3)	−0.08588 (18)	0.37784 (19)	0.0530 (6)
H4	0.0667	−0.1164	0.3467	0.064*
C5	0.1600 (2)	0.01205 (16)	0.32530 (16)	0.0390 (5)
C6	0.1434 (2)	0.07501 (15)	0.21526 (15)	0.0349 (4)
C7	0.04845 (18)	0.17351 (15)	0.21651 (14)	0.0313 (4)
C8	−0.0757 (2)	0.19521 (17)	0.18453 (15)	0.0404 (5)
H8	−0.1040	0.1488	0.1613	0.048*
C9	−0.1558 (2)	0.28565 (19)	0.18759 (17)	0.0471 (5)
H9	−0.2392	0.3011	0.1668	0.057*
C10	−0.1112 (2)	0.35281 (18)	0.22176 (17)	0.0471 (5)
H10	−0.1637	0.4147	0.2240	0.056*
C11	0.0128 (2)	0.32761 (16)	0.25290 (15)	0.0387 (5)
H11	0.0426	0.3734	0.2762	0.046*
C12	0.28077 (19)	0.11126 (15)	0.14989 (15)	0.0340 (4)
C13	0.3317 (2)	0.08941 (18)	0.06194 (17)	0.0454 (5)
H13	0.2849	0.0507	0.0413	0.054*
C14	0.4534 (3)	0.12597 (19)	0.00521 (18)	0.0529 (6)
H14	0.4884	0.1131	−0.0547	0.064*
C15	0.5216 (2)	0.18087 (19)	0.03765 (19)	0.0537 (6)
H15	0.6048	0.2039	0.0014	0.064*
C16	0.4654 (2)	0.20184 (18)	0.12520 (17)	0.0453 (5)
H16	0.5109	0.2407	0.1466	0.054*
C1'	0.2190 (2)	0.11662 (17)	0.78384 (17)	0.0435 (5)
H1'	0.1346	0.0918	0.8127	0.052*
C2'	0.3226 (2)	0.05019 (19)	0.7545 (2)	0.0562 (6)
H2'	0.3088	−0.0185	0.7635	0.067*
C3'	0.4475 (2)	0.0874 (2)	0.7115 (2)	0.0571 (6)
H3'	0.5192	0.0443	0.6904	0.069*
C4'	0.4649 (2)	0.18962 (18)	0.70021 (18)	0.0453 (5)
H4'	0.5487	0.2157	0.6717	0.054*
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'	0.4020	0.5330	0.5416	0.048*
C9'	0.2168 (2)	0.58487 (18)	0.50625 (16)	0.0466 (5)
H9'	0.2434	0.6394	0.4462	0.056*
C10'	0.0833 (2)	0.56725 (17)	0.53900 (15)	0.0410 (5)
H10'	0.0181	0.6102	0.5022	0.049*
C11'	0.0474 (2)	0.48495 (16)	0.62732 (14)	0.0341 (4)
H11'	−0.0430	0.4722	0.6490	0.041*
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'	0.4906	0.4344	0.8311	0.051*
C14'	0.3538 (2)	0.4352 (2)	0.95506 (18)	0.0505 (6)
H14'	0.4068	0.4620	0.9829	0.061*
C15'	0.2253 (2)	0.41100 (18)	1.00387 (16)	0.0455 (5)
H15'	0.1903	0.4211	1.0651	0.055*
C16'	0.1495 (2)	0.37165 (16)	0.96077 (14)	0.0370 (4)
H16'	0.0629	0.3545	0.9941	0.044*
H4A	0.077 (3)	0.046 (3)	0.116 (3)	0.088 (12)*
H4B	0.133 (3)	−0.039 (2)	0.180 (2)	0.053 (8)*
H4C	0.510 (2)	0.463 (2)	0.6662 (17)	0.041 (6)*
H4D	0.556 (3)	0.354 (2)	0.715 (2)	0.054 (8)*
N1	0.21948 (17)	0.05876 (14)	0.36963 (13)	0.0397 (4)
N2	0.09126 (15)	0.23921 (12)	0.25047 (11)	0.0311 (3)
N3	0.34651 (16)	0.16761 (13)	0.18047 (12)	0.0350 (4)
N4	0.0822 (2)	0.01220 (19)	0.17793 (18)	0.0477 (5)
N5	0.4350 (2)	0.16394 (19)	0.34980 (17)	0.0590 (5)
N6	0.4967 (2)	0.2294 (2)	0.35298 (19)	0.0679 (7)
N7	0.5618 (3)	0.2892 (3)	0.3565 (3)	0.1143 (12)
N8	0.31082 (19)	0.34925 (15)	0.22377 (14)	0.0442 (4)
N9	0.30464 (17)	0.41107 (15)	0.26644 (14)	0.0437 (4)
N10	0.2999 (2)	0.47478 (18)	0.30208 (18)	0.0608 (6)
N11	0.1681 (2)	0.24176 (17)	0.41551 (14)	0.0497 (5)
N12	0.2200 (2)	0.25807 (19)	0.47283 (15)	0.0576 (5)
N13	0.2617 (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) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1'	0.02280 (13)	0.02834 (15)	0.02953 (14)	−0.00705 (10)	−0.00219 (9)	−0.01100 (11)
Co1	0.03571 (15)	0.03377 (16)	0.03405 (15)	−0.00451 (11)	−0.00721 (11)	−0.01317 (12)
C1	0.0648 (15)	0.0494 (14)	0.0385 (12)	0.0027 (12)	−0.0097 (10)	−0.0072 (11)
C2	0.0843 (19)	0.0540 (16)	0.0415 (13)	0.0070 (15)	−0.0040 (13)	0.0027 (12)
C3	0.085 (2)	0.0351 (13)	0.0598 (16)	−0.0063 (13)	0.0103 (14)	0.0011 (12)
C4	0.0591 (14)	0.0327 (12)	0.0578 (14)	−0.0083 (10)	0.0051 (11)	−0.0124 (11)
C5	0.0373 (10)	0.0291 (10)	0.0439 (11)	−0.0003 (8)	0.0029 (8)	−0.0122 (9)
C6	0.0367 (10)	0.0284 (10)	0.0399 (10)	−0.0074 (8)	−0.0007 (8)	−0.0140 (8)
C7	0.0335 (9)	0.0297 (10)	0.0295 (9)	−0.0093 (8)	0.0014 (7)	−0.0102 (8)
C8	0.0386 (11)	0.0469 (13)	0.0390 (11)	−0.0096 (9)	−0.0050 (8)	−0.0175 (10)
C9	0.0364 (11)	0.0547 (14)	0.0476 (12)	0.0022 (10)	−0.0100 (9)	−0.0161 (11)
C10	0.0443 (12)	0.0408 (12)	0.0500 (12)	0.0088 (10)	−0.0074 (10)	−0.0150 (10)
C11	0.0452 (11)	0.0312 (10)	0.0398 (10)	−0.0024 (9)	−0.0027 (9)	−0.0157 (9)
C12	0.0346 (10)	0.0269 (10)	0.0379 (10)	−0.0005 (8)	−0.0024 (8)	−0.0117 (8)
C13	0.0518 (13)	0.0403 (12)	0.0457 (12)	−0.0014 (10)	−0.0021 (10)	−0.0219 (10)
C14	0.0590 (14)	0.0443 (13)	0.0473 (13)	−0.0017 (11)	0.0119 (11)	−0.0201 (11)
C15	0.0415 (12)	0.0458 (13)	0.0599 (14)	−0.0057 (10)	0.0147 (10)	−0.0155 (11)
C16	0.0351 (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)
N1	0.0420 (9)	0.0341 (9)	0.0351 (9)	0.0013 (7)	−0.0038 (7)	−0.0069 (7)
N2	0.0336 (8)	0.0272 (8)	0.0316 (8)	−0.0034 (6)	−0.0020 (6)	−0.0114 (7)
N3	0.0330 (8)	0.0321 (9)	0.0385 (9)	−0.0029 (7)	−0.0029 (7)	−0.0128 (7)
N4	0.0523 (12)	0.0377 (11)	0.0613 (14)	−0.0110 (10)	−0.0061 (10)	−0.0259 (11)
N5	0.0521 (12)	0.0670 (14)	0.0663 (13)	0.0004 (11)	−0.0281 (10)	−0.0250 (11)
N6	0.0386 (11)	0.100 (2)	0.0765 (16)	−0.0055 (12)	−0.0177 (10)	−0.0401 (15)
N7	0.0655 (17)	0.139 (3)	0.168 (3)	−0.0211 (19)	−0.043 (2)	−0.069 (3)
N8	0.0550 (11)	0.0400 (10)	0.0442 (10)	−0.0146 (8)	−0.0085 (8)	−0.0178 (9)
N9	0.0397 (10)	0.0428 (11)	0.0520 (11)	−0.0139 (8)	−0.0090 (8)	−0.0154 (9)
N10	0.0627 (13)	0.0567 (13)	0.0775 (15)	−0.0207 (11)	−0.0087 (11)	−0.0352 (12)
N11	0.0538 (11)	0.0620 (13)	0.0423 (10)	−0.0063 (9)	−0.0073 (8)	−0.0286 (9)
N12	0.0605 (12)	0.0751 (15)	0.0439 (11)	0.0040 (11)	−0.0146 (10)	−0.0297 (11)
N13	0.107 (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, º) top

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—N11	1.9335 (18)	C4'—H4'	0.930
Co1—N8	1.9406 (18)	C5'—N1'	1.346 (2)
Co1—N5	1.941 (2)	C5'—C6'	1.527 (3)
Co1—N3	1.9563 (17)	C6'—N4'	1.454 (2)
Co1—N1	1.9651 (18)	C6'—C7'	1.531 (3)
Co1—N2	1.9796 (16)	C6'—C12'	1.544 (3)
C1—N1	1.350 (3)	C7'—N2'	1.348 (2)
C1—C2	1.384 (4)	C7'—C8'	1.381 (3)
C1—H1	0.930	C8'—C9'	1.375 (3)
C2—C3	1.374 (4)	C8'—H8'	0.930
C2—H2	0.930	C9'—C10'	1.370 (3)
C3—C4	1.382 (4)	C9'—H9'	0.930
C3—H3	0.930	C10'—C11'	1.377 (3)
C4—C5	1.390 (3)	C10'—H10'	0.930
C4—H4	0.930	C11'—N2'	1.344 (2)
C5—N1	1.341 (3)	C11'—H11'	0.930
C5—C6	1.535 (3)	C12'—N3'	1.346 (2)
C6—N4	1.448 (3)	C12'—C13'	1.381 (3)
C6—C7	1.524 (3)	C13'—C14'	1.379 (3)
C6—C12	1.550 (3)	C13'—H13'	0.930
C7—N2	1.341 (3)	C14'—C15'	1.374 (3)
C7—C8	1.392 (3)	C14'—H14'	0.930
C8—C9	1.372 (3)	C15'—C16'	1.372 (3)
C8—H8	0.930	C15'—H15'	0.930
C9—C10	1.370 (3)	C16'—N3'	1.348 (2)
C9—H9	0.930	C16'—H16'	0.930
C10—C11	1.384 (3)	N4—H4A	0.86 (4)
C10—H10	0.930	N4—H4B	0.79 (3)
C11—N2	1.340 (2)	N5—N6	1.198 (3)
C11—H11	0.930	N6—N7	1.159 (4)
C12—N3	1.342 (3)	N8—N9	1.206 (3)
C12—C13	1.384 (3)	N9—N10	1.156 (3)
C13—C14	1.385 (3)	N11—N12	1.180 (3)
C13—H13	0.930	N12—N13	1.145 (3)
C14—C15	1.361 (4)	N4'—H4C	0.92 (3)
C14—H14	0.930	N4'—H4D	0.86 (3)
C15—C16	1.381 (3)	N5'—N6'	1.196 (2)
C15—H15	0.930	N6'—N7'	1.152 (2)
C16—N3	1.346 (3)	N8'—N9'	1.195 (2)
C16—H16	0.930	N9'—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—N8	92.79 (9)	N4'—C6'—C12'	113.23 (16)
N11—Co1—N5	94.33 (9)	C5'—C6'—C12'	109.64 (15)
N8—Co1—N5	92.47 (9)	C7'—C6'—C12'	106.98 (15)
N11—Co1—N3	174.49 (8)	N2'—C7'—C8'	121.22 (17)
N8—Co1—N3	88.90 (7)	N2'—C7'—C6'	115.82 (15)
N5—Co1—N3	90.83 (8)	C8'—C7'—C6'	122.96 (16)
N11—Co1—N1	90.12 (8)	C9'—C8'—C7'	119.35 (19)
N8—Co1—N1	176.71 (8)	C9'—C8'—H8'	120.3
N5—Co1—N1	88.82 (9)	C7'—C8'—H8'	120.3
N3—Co1—N1	88.06 (7)	C10'—C9'—C8'	119.51 (19)
N11—Co1—N2	86.79 (7)	C10'—C9'—H9'	120.2
N8—Co1—N2	90.55 (7)	C8'—C9'—H9'	120.2
N5—Co1—N2	176.72 (8)	C9'—C10'—C11'	118.90 (19)
N3—Co1—N2	87.95 (7)	C9'—C10'—H10'	120.5
N1—Co1—N2	88.10 (7)	C11'—C10'—H10'	120.5
N1—C1—C2	121.4 (3)	N2'—C11'—C10'	122.12 (18)
N1—C1—H1	119.3	N2'—C11'—H11'	118.9
C2—C1—H1	119.3	C10'—C11'—H11'	118.9
C3—C2—C1	119.1 (2)	N3'—C12'—C13'	121.07 (18)
C3—C2—H2	120.4	N3'—C12'—C6'	116.41 (16)
C1—C2—H2	120.4	C13'—C12'—C6'	122.49 (16)
C2—C3—C4	119.8 (2)	C14'—C13'—C12'	119.39 (19)
C2—C3—H3	120.1	C14'—C13'—H13'	120.3
C4—C3—H3	120.1	C12'—C13'—H13'	120.3
C3—C4—C5	118.5 (3)	C15'—C14'—C13'	119.4 (2)
C3—C4—H4	120.7	C15'—C14'—H14'	120.3
C5—C4—H4	120.7	C13'—C14'—H14'	120.3
N1—C5—C4	121.7 (2)	C16'—C15'—C14'	118.86 (19)
N1—C5—C6	116.48 (17)	C16'—C15'—H15'	120.6
C4—C5—C6	121.8 (2)	C14'—C15'—H15'	120.6
N4—C6—C7	109.19 (18)	N3'—C16'—C15'	122.15 (18)
N4—C6—C5	109.42 (18)	N3'—C16'—H16'	118.9
C7—C6—C5	106.55 (16)	C15'—C16'—H16'	118.9
N4—C6—C12	113.13 (17)	C5—N1—C1	119.4 (2)
C7—C6—C12	108.01 (15)	C5—N1—Co1	120.66 (14)
C5—C6—C12	110.32 (16)	C1—N1—Co1	119.71 (17)
N2—C7—C8	121.29 (18)	C11—N2—C7	118.97 (17)
N2—C7—C6	116.02 (17)	C11—N2—Co1	119.98 (14)
C8—C7—C6	122.69 (18)	C7—N2—Co1	121.03 (13)
C9—C8—C7	119.5 (2)	C16—N3—C12	119.15 (18)
C9—C8—H8	120.3	C16—N3—Co1	120.69 (15)
C7—C8—H8	120.3	C12—N3—Co1	120.07 (12)
C10—C9—C8	119.0 (2)	C6—N4—H4A	109 (2)
C10—C9—H9	120.5	C6—N4—H4B	107 (2)
C8—C9—H9	120.5	H4A—N4—H4B	107 (3)
C9—C10—C11	119.4 (2)	N6—N5—Co1	120.19 (19)
C9—C10—H10	120.3	N7—N6—N5	176.7 (3)
C11—C10—H10	120.3	N9—N8—Co1	120.37 (15)
N2—C11—C10	121.9 (2)	N10—N9—N8	176.1 (2)
N2—C11—H11	119.0	N12—N11—Co1	124.36 (17)
C10—C11—H11	119.0	N13—N12—N11	175.3 (3)
N3—C12—C13	121.27 (18)	C5'—N1'—C1'	119.33 (17)
N3—C12—C6	117.20 (16)	C5'—N1'—Co1'	120.43 (13)
C13—C12—C6	121.50 (19)	C1'—N1'—Co1'	120.21 (13)
C14—C13—C12	119.0 (2)	C11'—N2'—C7'	118.88 (16)
C14—C13—H13	120.5	C11'—N2'—Co1'	120.25 (12)
C12—C13—H13	120.5	C7'—N2'—Co1'	120.86 (12)
C15—C14—C13	119.6 (2)	C12'—N3'—C16'	119.08 (16)
C15—C14—H14	120.2	C12'—N3'—Co1'	120.54 (12)
C13—C14—H14	120.2	C16'—N3'—Co1'	120.30 (13)
C14—C15—C16	119.1 (2)	C6'—N4'—H4C	108.3 (14)
C14—C15—H15	120.5	C6'—N4'—H4D	106.8 (17)
C16—C15—H15	120.5	H4C—N4'—H4D	107 (2)
N3—C16—C15	121.9 (2)	N6'—N5'—Co1'	124.28 (14)
N3—C16—H16	119.1	N7'—N6'—N5'	174.3 (2)
C15—C16—H16	119.1	N9'—N8'—Co1'	123.02 (14)
N1'—C1'—C2'	122.4 (2)	N10'—N9'—N8'	175.1 (2)
N1'—C1'—H1'	118.8	N12'—N11'—Co1'	126.01 (14)
C2'—C1'—H1'	118.8	N13'—N12'—N11'	173.6 (2)

N1—C1—C2—C3	−1.5 (4)	N8—Co1—N2—C11	−46.96 (15)
C1—C2—C3—C4	3.1 (4)	N3—Co1—N2—C11	−135.84 (15)
C2—C3—C4—C5	−1.4 (4)	N1—Co1—N2—C11	136.03 (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—C7	134.66 (14)
N1—C5—C6—N4	178.02 (17)	N3—Co1—N2—C7	45.78 (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—C7	112.9 (2)	C6—C12—N3—C16	−179.17 (18)
N1—C5—C6—C12	52.9 (2)	C13—C12—N3—Co1	175.64 (15)
C4—C5—C6—C12	−130.1 (2)	C6—C12—N3—Co1	−2.4 (2)
N4—C6—C7—N2	179.37 (17)	C15—C16—N3—C12	0.2 (3)
C5—C6—C7—N2	61.3 (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—C12	134.50 (16)
C5—C6—C7—C8	−118.7 (2)	N1—Co1—N3—C12	45.72 (15)
C12—C6—C7—C8	122.74 (19)	N2—Co1—N3—C12	−42.45 (15)
N2—C7—C8—C9	0.1 (3)	N8—Co1—N3—C16	43.67 (17)
C6—C7—C8—C9	−179.86 (18)	N5—Co1—N3—C16	−48.78 (17)
C7—C8—C9—C10	0.3 (3)	N1—Co1—N3—C16	−137.57 (16)
C8—C9—C10—C11	−0.4 (3)	N2—Co1—N3—C16	134.27 (16)
C9—C10—C11—N2	0.1 (3)	N11—Co1—N5—N6	−70.1 (2)
N4—C6—C12—N3	−178.29 (19)	N8—Co1—N5—N6	22.9 (2)
C7—C6—C12—N3	60.7 (2)	N3—Co1—N5—N6	111.8 (2)
C5—C6—C12—N3	−55.3 (2)	N1—Co1—N5—N6	−160.2 (2)
N4—C6—C12—C13	3.7 (3)	N11—Co1—N8—N9	18.42 (18)
C7—C6—C12—C13	−117.3 (2)	N5—Co1—N8—N9	−76.04 (19)
C5—C6—C12—C13	126.6 (2)	N3—Co1—N8—N9	−166.82 (18)
N3—C12—C13—C14	0.5 (3)	N2—Co1—N8—N9	105.24 (18)
C6—C12—C13—C14	178.5 (2)	N8—Co1—N11—N12	−74.7 (2)
C12—C13—C14—C15	1.1 (3)	N5—Co1—N11—N12	18.0 (2)
C13—C14—C15—C16	−2.0 (4)	N1—Co1—N11—N12	106.8 (2)
C14—C15—C16—N3	1.4 (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—C1	3.5 (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—Co1	5.8 (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—Co1	172.90 (19)	N8'—Co1'—N3'—C16'	44.41 (15)
N11—Co1—N1—C5	126.64 (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—C5	39.85 (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—C1	46.39 (18)	N3'—Co1'—N5'—N6'	165.77 (18)
N3—Co1—N1—C1	137.25 (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—C7	0.3 (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—C11	179.59 (16)	N8'—Co1'—N11'—N12'	−35.41 (19)
C8—C7—N2—Co1	178.01 (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—C11	45.80 (15)	N1'—Co1'—N11'—N12'	148.24 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N6′ⁱ	0.86 (4)	2.68 (4)	3.463 (3)	154 (3)
N4—H4A···N5′ⁱ	0.86 (4)	2.69 (4)	3.514 (3)	163 (3)
N4′—H4C···N10ⁱⁱ	0.92 (3)	2.44 (2)	3.065 (3)	124.7 (18)
N4′—H4D···N13′ⁱⁱⁱ	0.86 (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.

Experimental details

Crystal data
Chemical formula	[Co(N₃)₃(C₁₆H₁₄N₄)]
M_r	447.33
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	10.2063 (3), 13.6760 (6), 14.4735 (2)
α, β, γ (°)	68.150 (3), 77.114 (2), 80.249 (2)
V (Å³)	1819.53 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.98
Crystal size (mm)	0.20 × 0.14 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.828, 0.892
No. of measured, independent and observed [I > 2σ(I)] reflections	18878, 6655, 5825
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.087, 1.00
No. of reflections	6655
No. of parameters	557
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.22

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N6'ⁱ	0.86 (4)	2.68 (4)	3.463 (3)	154 (3)
N4—H4A···N5'ⁱ	0.86 (4)	2.69 (4)	3.514 (3)	163 (3)
N4'—H4C···N10ⁱⁱ	0.92 (3)	2.44 (2)	3.065 (3)	124.7 (18)
N4'—H4D···N13'ⁱⁱⁱ	0.86 (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.

Acknowledgements

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

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. Web of Science CSD CrossRef Google Scholar
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