Aceto­nitrile{N-[2-(4,7-di­methyl-1,4,7-tri­aza­cyclo­non-1-yl)­ethyl]-N-[(1-methyl­benzimidazol-2-yl)­methyl]­methyl­amine}nickel(II) bis­(perchlorate) aceto­nitrile solvate

In the title compound, [Ni(C₂H₃N)(C₂₀H₃₄N₆)](ClO₄)₂·CH₃CN, Ni^II has approximately octahedral coordination geometry. The ligand donor atoms are five N atoms from the pendant-arm macrocyclic ligand (three from the macrocycle and two from the pendant arm) and one N atom from a coordinated aceto­nitrile mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in solvent or counterion
• R factor = 0.053
• wR factor = 0.118
• Data-to-parameter ratio = 11.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_302  Alert C Anion/Solvent Disorder .......................      43.00 Perc.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

Complexes that model structural aspects of the active sites of metalloproteins and enzymes have been valuable tools for the interpretation of enzyme mechanism and function at the molecular level (Kaim & Schwederski, 1994). For binuclear metalloenzymes, a large number of ligands with symmetric coordination environments have been prepared and their metal complexes investigated (Du Bois et al., 2000). However, to date, there has been a paucity of ligands that model asymmetric coordination environments in metalloenzymes. The de novo design of a new family of ligands that offer potentially binuclear asymmetric coordination environments for metal ions has now been achieved and will be reported elsewhere (Daly & Martin, 2001). These ligands offer potentially binuclear asymmetric coordination donor atoms that can result in selectivity in coordination to metal ions. Some examples of metalloenzymes that contain asymmetry as described include Cu/Zn superoxide dismutase (Holm et al., 1996), ribonucleotide reductase (Stubbe & Riggs-Gelasco, 1998), purple acid phosphatases (Barford et al., 1998) and haemerythrin (Liang et al., 1999).

The title compound, (I), was prepared to structurally characterize the pentadentate ligand, N-[2-(4,7-dimethyl-1,4,7-triazacyclonon-1-yl)ethyl]-N-[(1-methylbenzimidazol- 2-yl)methyl]methylamine. The nickel ion in the complex has approximately octahedral geometry, with a coordinated acetonitrile (N7) molecule in a trans position with respect to N1; the Ni—N7 bond length is 2.040 (3) Å. The pendant aminomethylbenzimidazole is bound so that its donor atoms, N4 and N5, are in trans positions with respect to atoms N2 and N3 of the macrocycle, respectively. Distortions from regular octahedral geometry about the metal ion are evident from the bond angles N1—Ni—N7, N2—Ni—N4 and N3—Ni—N5 of 177.39 (12), 169.99 (11) and 172.90 (11)°, respectively. The Ni—N(macrocycle) bond lengths are in the range 2.051 (3)–2.176 (3) Å. The uncoordinated acetonitrile molecule appears to have only a space-filling role in the crystal.

S2. Experimental

To a refluxing solution of [Ni(H₂O)₆](ClO₄)₂ (0.15 g, 0.559 mmol) in methanol (1 ml) was added a solution of the ligand, N-[2-(4,7-dimethyl-1,4,7-triazacyclonon-1-yl)ethyl]-N-[(1-methyl- benzimidazol-2-yl)methyl]methylamine (L; 0.20 g, 0.559 mmol) in methanol (1 ml) and the heating continued for 1 h. The resultant gum was stirred with ether to give a pink solid that was collected by filtration. This compound was recrystallized by ether diffusion into an acetonitrile solution to give pink plates. Yield: 0.202 g (55%). Microanalysis for C₂₂H₃₇Cl₂N₇NiO₈, calculated: C 40.21, H 5.67, N 14.92%; found: C 39.85, H 5.60, N 14.92%. λ_max (CH₃CN): 550 nm, ε: 8.628 M^-1 cm^-1, 924 nm; ε: 14.050 M^-1 cm^-1;µ: 3.88 BM. Crystals, grown by vapour diffusion of diethyl ether into an acetonitrile solution of the pink plates, formed in two habits. The majority of the complex crystallized as very thin plates with microanalysis of this compound suggesting the formula [NiL(CH₃CN)](ClO₄)₂. However, a small amount of complex crystallized as larger prisms that were suitable for X-ray structure determination. The IR spectra for both compounds over the range 2200–2360 cm^-1 displayed the CN stretch of a coordinated acetonitrile molecule. The main product showed one weak absorbance at ~2245 cm^-1, whereas the prisms of (I) showed an additional two CN bands at 2315 and 2286 cm^-1, attributable to a free acetonitrile molecule in the lattice, as they are equivalent to those bands arising from pure acetonitrile. The crystal used for data collection was cut from a 0.2 mm thick prism of the minor component.

S3. Refinement

Many reflections had streaks that extended into the scan range of neighboring reflections causing background imbalance and large net negative intensity, particularly for low order weak reflections. The original diffractometer output file was edited to remove severely affected reflections. This reduced the measured data from 10116 to 9685 reflections. H atoms were placed at calculated positions and not refined although their coordinates were recalculated several times during the refinement. Both perchlorate groups are severely disordered. They have been modelled by using two rigid groups each, with refined population parameters [Cl1/Cl1' 0.624/0.376 (8); Cl2/Cl2' 0.51/0.49 (1)]. This has satisfactorily accounted for the electron density in the regions of these groups.

Computing details

Data collection: CAD-4-PC (Enraf-Nonius, 1992); cell refinement: CAD-4-PC; data reduction: Xtal3.4 DIFDAT ABSORB SORTRF ADDREF (Hall et al., 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: Xtal3.4 CRYLSQ; molecular graphics: Xtal3.4 PIG ORTEP; software used to prepare material for publication: Xtal3.4 BONDLA CIFIO.

Figures

Fig. 1. The cation of the title compound with displacement ellipsoids at the 40% probability level.

(I)

Crystal data

[Ni(C2H3N)(C20H34N6)](ClO4)2·C2H3N	F(000) = 1464
Mr = 698.23	Dx = 1.477 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.474 (1) Å	θ = 18.1–21.8°
b = 30.475 (2) Å	µ = 0.85 mm^−1
c = 10.572 (1) Å	T = 293 K
β = 111.54 (1)°	Prism, pink
V = 3138.9 (5) Å^3	0.50 × 0.44 × 0.20 mm
Z = 4

Data collection

Enraf-Nonius CAD4/PC diffractometer	Rint = 0.021
θ/2θ scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: gaussian (ABSORB; Hall et al., 1995)	h = −13→12
Tmin = 0.657, Tmax = 0.851	k = 0→39
9685 measured reflections	l = −13→13
7088 independent reflections	3 standard reflections every 120 min
5189 reflections with F^2 > 2σ(F^2)	intensity decay: 1%

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters not refined
wR(F^2) = 0.118	Weighting scheme based on measured s.u.'s
S = 1.65	(Δ/σ)max = 0.002
5177 reflections	Δρmax = 0.60 e Å^−3
444 parameters	Δρmin = −0.48 e Å^−3
0 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni	0.24536 (4)	0.613827 (13)	0.18773 (4)	0.03486 (18)
N1	0.0544 (3)	0.58995 (9)	0.1622 (3)	0.0411 (12)
N2	0.3106 (3)	0.58613 (9)	0.3833 (3)	0.0448 (13)
N3	0.1842 (3)	0.66778 (9)	0.2880 (3)	0.0512 (15)
N4	0.1492 (3)	0.63397 (9)	−0.0253 (3)	0.0437 (13)
N5	0.2835 (3)	0.55403 (9)	0.0802 (2)	0.0372 (12)
N6	0.2864 (3)	0.53301 (9)	−0.1206 (3)	0.0417 (13)
N7	0.4311 (3)	0.63979 (10)	0.2070 (3)	0.0532 (16)
C21	0.5312 (4)	0.65544 (12)	0.2199 (4)	0.0534 (19)
C22	0.6639 (4)	0.67568 (16)	0.2380 (6)	0.085 (3)
C1	0.0841 (4)	0.54982 (12)	0.2476 (4)	0.0500 (17)
C2	0.1930 (4)	0.55896 (12)	0.3889 (3)	0.0536 (18)
C3	0.3369 (4)	0.62410 (13)	0.4782 (4)	0.058 (2)
C4	0.2216 (5)	0.65591 (14)	0.4346 (4)	0.063 (2)
C5	0.0329 (4)	0.66887 (13)	0.2194 (4)	0.060 (2)
C6	−0.0263 (4)	0.62266 (13)	0.2066 (4)	0.0541 (19)
C7	0.4402 (4)	0.56060 (13)	0.4228 (4)	0.062 (2)
C8	0.2430 (5)	0.71145 (13)	0.2803 (5)	0.077 (2)
C9	−0.0117 (3)	0.57974 (13)	0.0152 (4)	0.0498 (17)
C10	0.0039 (4)	0.61843 (14)	−0.0685 (3)	0.0545 (18)
C11	0.2258 (4)	0.61114 (12)	−0.0984 (3)	0.0498 (17)
C12	0.2650 (3)	0.56581 (11)	−0.0455 (3)	0.0392 (14)
C13	0.3216 (3)	0.49613 (11)	−0.0397 (3)	0.0407 (15)
C14	0.3566 (3)	0.45436 (12)	−0.0656 (4)	0.0505 (17)
C15	0.3837 (4)	0.42408 (13)	0.0378 (4)	0.058 (2)
C16	0.3714 (4)	0.43516 (12)	0.1602 (4)	0.0542 (18)
C17	0.3372 (3)	0.47717 (12)	0.1864 (3)	0.0462 (16)
C18	0.3171 (3)	0.50916 (11)	0.0856 (3)	0.0386 (14)
C19	0.2743 (4)	0.53531 (15)	−0.2638 (4)	0.062 (2)
C20	0.1489 (5)	0.68062 (13)	−0.0636 (4)	0.068 (2)
N8	−0.0370 (6)	0.7722 (2)	0.0019 (6)	0.121 (4)
C23	−0.1066 (6)	0.77874 (17)	0.0589 (6)	0.083 (3)
C24	−0.1982 (6)	0.7869 (2)	0.1287 (6)	0.105 (4)
Cl1	0.1414 (4)	0.41985 (12)	0.4590 (4)	0.0601 (17)	.624 (7)
O11	0.0246 (5)	0.39330 (18)	0.4497 (8)	0.087 (4)	.624 (7)
O12	0.2418 (7)	0.39321 (19)	0.4315 (9)	0.125 (5)	.624 (7)
O13	0.2011 (8)	0.4380 (2)	0.5939 (5)	0.160 (8)	.624 (7)
O14	0.0982 (7)	0.4550 (2)	0.3612 (7)	0.141 (6)	.624 (7)
Cl1'	0.1410 (7)	0.42525 (19)	0.4813 (7)	0.054 (2)	.376 (7)
O11'	0.0427 (14)	0.3916 (4)	0.4216 (13)	0.156 (13)	.376 (7)
O12'	0.2060 (12)	0.4342 (4)	0.3853 (11)	0.125 (10)	.376 (7)
O13'	0.2435 (10)	0.4129 (5)	0.6100 (10)	0.131 (10)	.376 (7)
O14'	0.0704 (16)	0.4639 (3)	0.4989 (15)	0.135 (10)	.376 (7)
Cl2	0.5658 (6)	0.69624 (14)	−0.1533 (5)	0.078 (2)	.506 (11)
O21	0.7015 (13)	0.6831 (10)	−0.0655 (8)	0.106 (6)	.506 (11)
O22	0.562 (3)	0.74323 (15)	−0.1706 (18)	0.121 (7)	.506 (11)
O23	0.5314 (12)	0.6753 (5)	−0.2837 (9)	0.197 (12)	.506 (11)
O24	0.4681 (15)	0.6836 (8)	−0.0934 (13)	0.135 (9)	.506 (11)
Cl2'	0.5339 (7)	0.69945 (14)	−0.1806 (6)	0.077 (2)	.494 (11)
O21'	0.6716 (8)	0.6826 (3)	−0.1379 (13)	0.196 (14)	.494 (11)
O22'	0.4388 (10)	0.6636 (3)	−0.2025 (14)	0.130 (7)	.494 (11)
O23'	0.5221 (13)	0.7280 (4)	−0.0766 (12)	0.237 (16)	.494 (11)
O24'	0.5029 (12)	0.7238 (4)	−0.3050 (10)	0.171 (10)	.494 (11)
H1a	0.00257	0.53974	0.25688	0.08000*
H1b	0.11806	0.52768	0.20404	0.08000*
H2a	0.15088	0.57470	0.44142	0.08000*
H2b	0.22776	0.53197	0.43270	0.08000*
H3a	0.35282	0.61355	0.56860	0.08000*
H3b	0.41944	0.63871	0.48101	0.08000*
H4a	0.14310	0.64263	0.44761	0.08000*
H4b	0.24536	0.68161	0.49037	0.08000*
H5a	−0.00579	0.68679	0.26978	0.08000*
H5b	0.00982	0.68100	0.13038	0.08000*
H6a	−0.03040	0.61420	0.29207	0.08000*
H6b	−0.11982	0.62327	0.14099	0.08000*
H9a	0.03120	0.55414	−0.00410	0.08000*
H9b	−0.10634	0.57343	−0.00540	0.08000*
H10a	−0.02646	0.60902	−0.16183	0.08000*
H10b	−0.05230	0.64136	−0.06044	0.08000*
H11a	0.16765	0.60972	−0.19237	0.08000*
H11b	0.30510	0.62743	−0.08868	0.08000*
H14	0.36419	0.44669	−0.14978	0.08000*
H15	0.40812	0.39451	0.02436	0.08000*
H16	0.38666	0.41290	0.23172	0.08000*
H17	0.32670	0.48401	0.27082	0.08000*
H19a	0.36287	0.53298	−0.26882	0.09100*
H19b	0.23350	0.56229	−0.30229	0.09100*
H19c	0.21857	0.51164	−0.31306	0.09100*
H22a	0.67766	0.67515	0.15390	0.12500*
H22b	0.73555	0.66043	0.30491	0.12500*
H22c	0.66326	0.70556	0.26560	0.12500*
H24a	−0.23055	0.81663	0.11277	0.15300*
H24b	−0.15152	0.78290	0.22383	0.15300*
H24c	−0.27468	0.76772	0.09696	0.15300*
H7a	0.51138	0.57906	0.41734	0.10000*
H7b	0.42807	0.53654	0.36225	0.10000*
H7c	0.46401	0.55017	0.51277	0.10000*
H8a	0.21973	0.71932	0.18817	0.10000*
H8b	0.33936	0.71047	0.32511	0.10000*
H8c	0.20535	0.73240	0.32413	0.10000*
H20a	0.24154	0.69082	−0.03702	0.10000*
H20b	0.10212	0.69758	−0.01958	0.10000*
H20c	0.10521	0.68357	−0.15950	0.10000*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.0298 (2)	0.0396 (2)	0.0344 (2)	−0.00436 (18)	0.01088 (17)	0.00013 (18)
N1	0.0326 (13)	0.0508 (16)	0.0415 (14)	−0.0072 (12)	0.0154 (13)	−0.0035 (13)
N2	0.0440 (16)	0.0522 (16)	0.0332 (14)	−0.0045 (14)	0.0084 (14)	−0.0031 (13)
N3	0.0531 (18)	0.0437 (16)	0.0576 (18)	−0.0010 (14)	0.0211 (16)	−0.0076 (14)
N4	0.0453 (16)	0.0452 (15)	0.0409 (15)	0.0051 (13)	0.0163 (14)	0.0088 (12)
N5	0.0348 (13)	0.0450 (15)	0.0316 (12)	0.0012 (12)	0.0120 (12)	0.0015 (11)
N6	0.0348 (14)	0.0586 (18)	0.0324 (14)	−0.0015 (13)	0.0133 (12)	−0.0044 (13)
N7	0.0446 (17)	0.0562 (19)	0.063 (2)	−0.0124 (15)	0.0242 (16)	−0.0054 (15)
C21	0.046 (2)	0.052 (2)	0.066 (2)	−0.0092 (18)	0.026 (2)	−0.010 (2)
C22	0.052 (2)	0.088 (3)	0.124 (4)	−0.030 (2)	0.044 (3)	−0.029 (3)
C1	0.049 (2)	0.056 (2)	0.052 (2)	−0.0135 (18)	0.0270 (18)	−0.0018 (17)
C2	0.065 (2)	0.056 (2)	0.0426 (19)	−0.0126 (19)	0.022 (2)	0.0037 (17)
C3	0.063 (2)	0.065 (3)	0.0408 (18)	−0.005 (2)	0.012 (2)	−0.0149 (18)
C4	0.072 (3)	0.071 (3)	0.048 (2)	−0.007 (2)	0.024 (2)	−0.019 (2)
C5	0.052 (2)	0.063 (2)	0.067 (3)	0.0121 (19)	0.024 (2)	−0.008 (2)
C6	0.0372 (18)	0.068 (2)	0.063 (2)	0.0038 (17)	0.0246 (18)	−0.002 (2)
C7	0.058 (2)	0.064 (2)	0.048 (2)	0.009 (2)	0.000 (2)	−0.0015 (18)
C8	0.087 (3)	0.048 (2)	0.095 (3)	−0.012 (2)	0.030 (3)	−0.016 (2)
C9	0.0281 (16)	0.070 (2)	0.0447 (19)	−0.0074 (16)	0.0052 (16)	−0.0069 (18)
C10	0.0379 (18)	0.078 (3)	0.0400 (18)	0.0089 (19)	0.0053 (17)	0.0013 (18)
C11	0.053 (2)	0.059 (2)	0.0404 (17)	0.0010 (18)	0.0206 (17)	0.0088 (17)
C12	0.0304 (15)	0.053 (2)	0.0338 (16)	−0.0028 (15)	0.0117 (14)	0.0001 (15)
C13	0.0275 (15)	0.057 (2)	0.0384 (17)	−0.0053 (15)	0.0125 (15)	−0.0038 (16)
C14	0.0359 (18)	0.057 (2)	0.057 (2)	−0.0015 (17)	0.0154 (18)	−0.0172 (18)
C15	0.038 (2)	0.050 (2)	0.078 (3)	0.0037 (17)	0.010 (2)	−0.009 (2)
C16	0.041 (2)	0.054 (2)	0.055 (2)	0.0034 (17)	0.0037 (19)	0.0016 (18)
C17	0.0382 (17)	0.051 (2)	0.0411 (18)	−0.0025 (16)	0.0053 (16)	0.0011 (15)
C18	0.0283 (16)	0.0468 (18)	0.0381 (16)	−0.0026 (14)	0.0094 (14)	−0.0043 (15)
C19	0.057 (2)	0.095 (3)	0.0342 (17)	0.000 (2)	0.0187 (18)	−0.005 (2)
C20	0.083 (3)	0.055 (2)	0.067 (3)	0.016 (2)	0.030 (3)	0.022 (2)
N8	0.118 (4)	0.130 (4)	0.134 (5)	0.032 (4)	0.068 (4)	0.033 (4)
C23	0.089 (4)	0.073 (3)	0.082 (3)	0.003 (3)	0.025 (3)	0.008 (3)
C24	0.106 (4)	0.113 (5)	0.097 (4)	−0.021 (4)	0.041 (4)	−0.008 (3)
Cl1	0.063 (2)	0.0694 (18)	0.0490 (19)	−0.0063 (14)	0.0218 (14)	−0.0129 (12)
O11	0.071 (4)	0.108 (6)	0.095 (5)	−0.015 (4)	0.046 (4)	0.011 (4)
O12	0.081 (4)	0.134 (6)	0.166 (7)	−0.007 (4)	0.051 (5)	−0.061 (6)
O13	0.166 (10)	0.178 (10)	0.090 (6)	0.004 (8)	−0.009 (6)	−0.068 (6)
O14	0.193 (9)	0.093 (5)	0.159 (7)	0.004 (5)	0.089 (7)	0.038 (5)
Cl1'	0.059 (3)	0.066 (3)	0.038 (2)	−0.020 (2)	0.0200 (18)	−0.013 (2)
O11'	0.173 (15)	0.199 (18)	0.118 (11)	−0.140 (14)	0.080 (11)	−0.073 (10)
O12'	0.130 (11)	0.161 (14)	0.119 (9)	−0.011 (10)	0.085 (9)	0.021 (9)
O13'	0.112 (10)	0.166 (15)	0.086 (8)	0.002 (10)	0.004 (7)	0.045 (9)
O14'	0.107 (9)	0.113 (9)	0.197 (16)	−0.002 (7)	0.071 (10)	−0.041 (9)
Cl2	0.075 (2)	0.072 (2)	0.089 (2)	−0.0074 (18)	0.035 (2)	0.0129 (19)
O21	0.096 (6)	0.100 (6)	0.110 (7)	0.007 (5)	0.023 (5)	0.022 (5)
O22	0.125 (7)	0.049 (4)	0.209 (14)	0.006 (4)	0.086 (9)	0.001 (6)
O23	0.211 (14)	0.248 (18)	0.119 (9)	−0.048 (13)	0.045 (9)	−0.114 (11)
O24	0.109 (7)	0.112 (8)	0.223 (15)	−0.010 (6)	0.107 (9)	0.044 (9)
Cl2'	0.095 (3)	0.047 (2)	0.094 (3)	−0.0084 (17)	0.040 (3)	−0.0107 (18)
O21'	0.077 (7)	0.263 (17)	0.27 (2)	0.053 (10)	0.087 (11)	0.117 (15)
O22'	0.143 (9)	0.119 (8)	0.127 (9)	−0.045 (7)	0.048 (8)	−0.007 (7)
O23'	0.196 (16)	0.30 (2)	0.154 (13)	0.100 (17)	−0.011 (11)	−0.119 (15)
O24'	0.204 (13)	0.138 (11)	0.177 (12)	−0.031 (10)	0.079 (10)	0.048 (10)

Geometric parameters (Å, º)

Ni—N1	2.051 (3)	C8—H8b	0.945
Ni—N2	2.101 (3)	C8—H8c	0.955
Ni—N3	2.176 (3)	C9—C10	1.518 (6)
Ni—N4	2.190 (3)	C9—H9a	0.959
Ni—N5	2.260 (3)	C9—H9b	0.953
Ni—N7	2.040 (3)	C10—H10a	0.963
N1—C1	1.484 (5)	C10—H10b	0.937
N1—C6	1.490 (5)	C11—C12	1.490 (5)
N1—C9	1.484 (4)	C11—H11a	0.957
N2—C2	1.503 (5)	C11—H11b	0.941
N2—C3	1.490 (5)	C13—C14	1.380 (5)
N2—C7	1.485 (5)	C13—C18	1.400 (5)
N3—C4	1.497 (5)	C14—C15	1.378 (6)
N3—C5	1.481 (5)	C14—H14	0.951
N3—C8	1.481 (5)	C15—C16	1.389 (7)
N4—C10	1.496 (5)	C15—H15	0.961
N4—C11	1.476 (5)	C16—C17	1.384 (5)
N4—C20	1.478 (5)	C16—H16	0.984
N5—C12	1.321 (4)	C17—C18	1.402 (5)
N5—C18	1.408 (4)	C17—H17	0.961
N6—C12	1.345 (5)	C19—H19a	0.951
N6—C13	1.378 (4)	C19—H19b	0.947
N6—C19	1.473 (5)	C19—H19c	0.953
N7—C21	1.114 (5)	C20—H20a	0.957
C21—C22	1.468 (6)	C20—H20b	0.945
C22—H22a	0.952	C20—H20c	0.951
C22—H22b	0.943	N8—C23	1.120 (10)
C22—H22c	0.957	C23—C24	1.431 (10)
C1—C2	1.535 (4)	C24—H24a	0.960
C1—H1a	0.946	C24—H24b	0.951
C1—H1b	0.956	C24—H24c	0.948
C2—H2a	0.956	Cl1—O11	1.439
C2—H2b	0.949	Cl1—O12	1.440
C3—C4	1.483 (6)	Cl1—O13	1.441
C3—H3a	0.963	Cl1—O14	1.441
C3—H3b	0.964	Cl1'—O11'	1.427
C4—H4a	0.971	Cl1'—O12'	1.440
C4—H4b	0.957	Cl1'—O13'	1.440
C5—C6	1.525 (6)	Cl1'—O14'	1.439
C5—H5a	0.951	Cl2—O21	1.440
C5—H5b	0.956	Cl2—O22	1.442
C6—H6a	0.955	Cl2—O23	1.439
C6—H6b	0.970	Cl2—O24	1.440
C7—H7a	0.952	Cl2'—O21'	1.439
C7—H7b	0.951	Cl2'—O22'	1.438
C7—H7c	0.946	Cl2'—O23'	1.442
C8—H8a	0.944	Cl2'—O24'	1.440
N1—Ni—N2	86.34 (11)	H7a—C7—H7b	109.2
N1—Ni—N3	83.38 (12)	H7a—C7—H7c	109.6
N1—Ni—N4	84.61 (11)	H7b—C7—H7c	109.8
N1—Ni—N5	89.51 (11)	N3—C8—H8a	109.3
N1—Ni—N7	177.39 (12)	N3—C8—H8b	109.5
N2—Ni—N3	82.64 (12)	N3—C8—H8c	108.6
N2—Ni—N4	169.99 (11)	H8a—C8—H8b	110.4
N2—Ni—N5	96.72 (10)	H8a—C8—H8c	109.5
N2—Ni—N7	95.97 (12)	H8b—C8—H8c	109.5
N3—Ni—N4	100.52 (11)	N1—C9—C10	109.8 (3)
N3—Ni—N5	172.90 (11)	N1—C9—H9a	108.5
N3—Ni—N7	95.69 (13)	N1—C9—H9b	109.1
N4—Ni—N5	78.95 (10)	C10—C9—H9a	110.4
N4—Ni—N7	93.17 (12)	C10—C9—H9b	110.5
N5—Ni—N7	91.42 (12)	H9a—C9—H9b	108.5
Ni—N1—C1	103.7 (2)	N4—C10—C9	112.5 (3)
Ni—N1—C6	111.1 (2)	N4—C10—H10a	108.8
Ni—N1—C9	105.7 (2)	N4—C10—H10b	109.8
C1—N1—C6	112.1 (3)	C9—C10—H10a	107.4
C1—N1—C9	112.2 (3)	C9—C10—H10b	108.7
C6—N1—C9	111.7 (2)	H10a—C10—H10b	109.4
Ni—N2—C2	106.55 (17)	N4—C11—C12	111.6 (3)
Ni—N2—C3	105.3 (2)	N4—C11—H11a	107.7
Ni—N2—C7	114.9 (3)	N4—C11—H11b	108.8
C2—N2—C3	110.6 (3)	C12—C11—H11a	109.3
C2—N2—C7	112.2 (3)	C12—C11—H11b	109.7
C3—N2—C7	107.1 (3)	H11a—C11—H11b	109.7
Ni—N3—C4	108.0 (2)	N5—C12—N6	113.4 (3)
Ni—N3—C5	103.4 (2)	N5—C12—C11	123.2 (3)
Ni—N3—C8	116.7 (3)	N6—C12—C11	123.4 (3)
C4—N3—C5	109.8 (4)	N6—C13—C14	131.2 (3)
C4—N3—C8	108.5 (3)	N6—C13—C18	105.2 (3)
C5—N3—C8	110.2 (3)	C14—C13—C18	123.6 (3)
Ni—N4—C10	104.9 (2)	C13—C14—C15	116.9 (4)
Ni—N4—C11	105.86 (18)	C13—C14—H14	122.2
Ni—N4—C20	120.4 (2)	C15—C14—H14	120.9
C10—N4—C11	112.2 (3)	C14—C15—C16	120.9 (4)
C10—N4—C20	108.7 (3)	C14—C15—H15	120.0
C11—N4—C20	104.9 (3)	C16—C15—H15	119.1
Ni—N5—C12	107.4 (2)	C15—C16—C17	122.1 (4)
Ni—N5—C18	148.3 (2)	C15—C16—H16	120.3
C12—N5—C18	104.3 (3)	C17—C16—H16	117.7
C12—N6—C13	107.7 (3)	C16—C17—C18	117.9 (4)
C12—N6—C19	126.9 (3)	C16—C17—H17	120.8
C13—N6—C19	125.4 (3)	C18—C17—H17	121.2
Ni—N7—C21	177.1 (4)	N5—C18—C13	109.4 (3)
N7—C21—C22	179.4 (4)	N5—C18—C17	132.2 (3)
C21—C22—H22a	109.4	C13—C18—C17	118.3 (3)
C21—C22—H22b	110.2	N6—C19—H19a	109.7
C21—C22—H22c	109.1	N6—C19—H19b	109.8
H22a—C22—H22b	109.9	N6—C19—H19c	109.3
H22a—C22—H22c	108.8	H19a—C19—H19b	109.6
H22b—C22—H22c	109.5	H19a—C19—H19c	109.1
N1—C1—C2	110.9 (3)	H19b—C19—H19c	109.4
N1—C1—H1a	109.6	N4—C20—H20a	109.4
N1—C1—H1b	108.7	N4—C20—H20b	109.9
C2—C1—H1a	109.6	N4—C20—H20c	109.6
C2—C1—H1b	108.8	H20a—C20—H20b	109.3
H1a—C1—H1b	109.3	H20a—C20—H20c	108.8
N2—C2—C1	112.9 (3)	H20b—C20—H20c	109.9
N2—C2—H2a	107.8	N8—C23—C24	178.6 (6)
N2—C2—H2b	108.9	C23—C24—H24a	109.5
C1—C2—H2a	108.7	C23—C24—H24b	110.0
C1—C2—H2b	109.4	C23—C24—H24c	110.5
H2a—C2—H2b	109.1	H24a—C24—H24b	108.5
N2—C3—C4	111.7 (3)	H24a—C24—H24c	108.8
N2—C3—H3a	109.3	H24b—C24—H24c	109.6
N2—C3—H3b	108.7	O11—Cl1—O12	109.5
C4—C3—H3a	110.6	O11—Cl1—O13	109.5
C4—C3—H3b	109.0	O11—Cl1—O14	109.5
H3a—C3—H3b	107.3	O12—Cl1—O13	109.5
N3—C4—C3	110.7 (4)	O12—Cl1—O14	109.5
N3—C4—H4a	109.5	O13—Cl1—O14	109.4
N3—C4—H4b	110.5	O11'—Cl1'—O12'	106.0
C3—C4—H4a	108.6	O11'—Cl1'—O13'	113.3
C3—C4—H4b	110.2	O11'—Cl1'—O14'	109.0
H4a—C4—H4b	107.2	O12'—Cl1'—O13'	109.5
N3—C5—C6	110.5 (3)	O12'—Cl1'—O14'	109.5
N3—C5—H5a	109.8	O13'—Cl1'—O14'	109.5
N3—C5—H5b	109.2	O21—Cl2—O22	109.4
C6—C5—H5a	109.7	O21—Cl2—O23	109.5
C6—C5—H5b	108.8	O21—Cl2—O24	109.5
H5a—C5—H5b	108.9	O22—Cl2—O23	109.4
N1—C6—C5	112.7 (3)	O22—Cl2—O24	109.4
N1—C6—H6a	110.2	O23—Cl2—O24	109.5
N1—C6—H6b	109.1	O21'—Cl2'—O22'	109.6
C5—C6—H6a	108.9	O21'—Cl2'—O23'	109.4
C5—C6—H6b	108.5	O21'—Cl2'—O24'	109.5
H6a—C6—H6b	107.3	O22'—Cl2'—O23'	109.4
N2—C7—H7a	109.2	O22'—Cl2'—O24'	109.5
N2—C7—H7b	109.4	O23'—Cl2'—O24'	109.4
N2—C7—H7c	109.6