[N,N′-Bis(pyrrol-2-ylmethyl­ene)cyclo­hexane-1,2-diaminato-κ4N]nickel(II)

Chen, J.-M.; Ruan, W.-J.; Gao, F.; Zhang, Y.-H.; Zhu, Z.-A.

doi:10.1107/S1600536807020673

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[N,N′-Bis(pyrrol-2-ylmethylene)cyclohexane-1,2-diaminato-κ⁴N]nickel(II)

J.-M. Chen, W.-J. Ruan, F. Gao, Y.-H. Zhang and Z.-A. Zhu

The tetradentate Schiff base ligand derived from the condensation of pyrrole-2-carbaldehyde and cyclohexane-1,2-diamine forms a square-planar four-coordinate Ni complex, [Ni(C₁₆H₁₈N₄)]. The compound crystallizes with two crystallographically independent molecules in the asymmetric unit.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020673/bt2334sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020673/bt2334Isup2.hkl Contains datablock I

CCDC reference: 646686

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.010 Å
Disorder in main residue
R factor = 0.061
wR factor = 0.136
Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         C8
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C24

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.74 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.89 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C9
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      27.40 Deg.
              C6   -N2   -C6'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.70 Deg.
              C11  -N3   -C11'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.70 Deg.
              C22  -N6   -C22'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.20 Deg.
              C27  -N7   -C27'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.50 Deg.
              C6'  -C7   -C6      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      27.70 Deg.
              H7A  -C7   -H7C     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      27.30 Deg.
              H7B  -C7   -H7D     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      27.70 Deg.
              C11  -C10  -C11'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.40 Deg.
              H10A -C10  -H10C    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.80 Deg.
              H10B -C10  -H10D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.70 Deg.
              C22' -C23  -C22     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      30.00 Deg.
              H23A -C23  -H23C    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      29.20 Deg.
              H23B -C23  -H23D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.30 Deg.
              C27  -C26  -C27'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.60 Deg.
              H26A -C26  -H26C    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.70 Deg.
              H26B -C26  -H26D    1.555   1.555   1.555

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         12

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  22 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  21 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

salen ligands (salen = N,N'-bis(salicyldene)ethylenediamine) and their complexes have received continuous and intensive attention because of their capabilities to serve as catalysts of organic reactions (Baleizao & Garcia, 2006), models of catalytic centers of metalloenzymes (Maruyama et al., 1990; Carey et al., 2004) and nonlinear optical materials (Rigamonti et al., 2006; Tedim et al., 2006). On the contrary, little is known about the ligand behaviour of the analogous compounds derived from pyrrole 2-carboxaldehyde and about the properties of their complexes (Weber, 1967; Downing & Urbach, 1971; Bacchi et al., 2003, Bella et al., 2004). In the present work, we have prepared the title compound (I) and determined its crystal structure.

The complex crystallizes with two crystallographically independent, but quite similar molecules in the asymmetric unit. In both molecules, the ligand is bideprotonated and the Ni(II) ion is tetracoordinated in a square planar environment, with the pyrrole and imine nitrogen atoms as donors. The coordination induces the formation of three five-membered chelate rings, and the N—Ni—N angles are less than 90°. The Ni—N (pyrrole) distances are significantly longer than the Ni—N (imine) distances.

Related literature top

For related literature, see: Bacchi et al. (2003); Baleizao & Garcia (2006); Bella et al. (2004); Carey et al. (2004); Downing & Urbach (1971); Maruyama et al. (1990); Rigamonti et al. (2006); Tedim et al. (2006); Weber (1967).

Experimental top

The title complex was synthesized by dissolving N,N'-bis(pyrrol-2- ylmethylene)cyclohexylenediamine (1 mmol, 268 mg) in ethanol (15 ml), with the addition of nickel(II) acetate (1 mmol, 212 mg) dissolved in distilled water (5 ml). The mixture was stirred at room temperature for 2 h and the resulting red–brown precipitate was filtered, dried and chromatographed on silica gel eluted with CHCl₃. Crystals suitable for X-ray diffraction analysis were obtained by recrystallization from a CHCl₃ solution. Elemental composition, calculated: C 59.12, H 5.58, N 17.24%; found: C 59.14, H 5.45, N 17.35%. M⁺ = 324 g mol^{-1. 1}H NMR (300 MHz, CDCl₃, 298 K, TMS): 7.23 (s, 2H, H imine), 6.80 (s, 2H, H pyrrole α), 6.59 (t, J = 3.6 Hz, 2H, H pyrrole γ), 6.13 (t, J = 3.0 Hz, 2H, H

pyrrole β), 3.34 (t, J = 3.5 Hz, 2H, CH), 2.24–1.31 (m, 8H, CH₂).

Structure description top

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. A view of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by circles of arbitrary size, and only one set of disordered C atoms are represented.

[N,N'-Bis(pyrrol-2-ylmethylene)cyclohexane-1,2-diaminato-κ⁴N]nickel(II) top

Crystal data top

[Ni(C₁₆H₁₈N₄)]	F(000) = 1360
M_r = 325.05	D_x = 1.442 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.379 (3) Å	Cell parameters from 4354 reflections
b = 8.6247 (10) Å	θ = 2.5–25.5°
c = 17.475 (2) Å	µ = 1.29 mm⁻¹
β = 111.697 (2)°	T = 294 K
V = 2993.9 (6) Å³	Block, red
Z = 8	0.26 × 0.22 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	6100 independent reflections
Radiation source: fine-focus sealed tube	4081 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 26.4°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→25
T_min = 0.730, T_max = 0.800	k = −10→7
16412 measured reflections	l = −20→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.061	H-atom parameters constrained
wR(F²) = 0.136	w = 1/[σ²(F_o²) + 10.3102P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max = 0.001
6100 reflections	Δρ_max = 0.39 e Å⁻³
418 parameters	Δρ_min = −0.41 e Å⁻³
12 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00459 (17)

Crystal data top

[Ni(C₁₆H₁₈N₄)]	V = 2993.9 (6) Å³
M_r = 325.05	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.379 (3) Å	µ = 1.29 mm⁻¹
b = 8.6247 (10) Å	T = 294 K
c = 17.475 (2) Å	0.26 × 0.22 × 0.18 mm
β = 111.697 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6100 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4081 reflections with I > 2σ(I)
T_min = 0.730, T_max = 0.800	R_int = 0.040
16412 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	12 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + 10.3102P] where P = (F_o² + 2F_c²)/3
6100 reflections	Δρ_max = 0.39 e Å⁻³
418 parameters	Δρ_min = −0.41 e Å⁻³

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	Occ. (<1)
Ni1	1.03966 (3)	0.31724 (8)	0.46424 (4)	0.0414 (2)
Ni2	0.46464 (3)	0.30951 (8)	0.42360 (4)	0.0433 (2)
N1	1.0592 (2)	0.4251 (5)	0.3818 (3)	0.0465 (11)
N2	0.9512 (2)	0.3281 (5)	0.3915 (3)	0.0474 (11)
N3	1.0027 (2)	0.2221 (5)	0.5330 (3)	0.0469 (11)
N4	1.1217 (2)	0.3006 (5)	0.5555 (3)	0.0459 (11)
N5	0.4469 (3)	0.4146 (5)	0.3230 (3)	0.0508 (12)
N6	0.5536 (2)	0.3479 (5)	0.4403 (3)	0.0515 (12)
N7	0.4986 (2)	0.2207 (5)	0.5273 (3)	0.0449 (11)
N8	0.3804 (2)	0.2682 (5)	0.4305 (3)	0.0437 (11)
C1	1.1105 (3)	0.4849 (7)	0.3641 (4)	0.0562 (15)
H1	1.1558	0.4715	0.3962	0.067*
C2	1.0866 (4)	0.5684 (8)	0.2921 (4)	0.0667 (18)
H2	1.1124	0.6202	0.2675	0.080*
C3	1.0173 (4)	0.5614 (7)	0.2631 (4)	0.0613 (17)
H3	0.9876	0.6084	0.2157	0.074*
C4	1.0007 (3)	0.4706 (6)	0.3183 (3)	0.0482 (14)
C5	0.9415 (3)	0.4129 (7)	0.3273 (3)	0.0542 (15)
H5	0.8986	0.4350	0.2895	0.065*
C6	0.9065 (4)	0.2229 (14)	0.4133 (6)	0.047 (4)	0.495 (15)
H6A	0.9163	0.1172	0.4006	0.056*	0.495 (15)
C11	0.9294 (4)	0.2363 (14)	0.5065 (7)	0.047 (4)	0.495 (15)
H11A	0.9185	0.3402	0.5205	0.057*	0.495 (15)
C6'	0.9007 (4)	0.2944 (15)	0.4278 (6)	0.050 (4)	0.505 (15)
H6B	0.8968	0.3850	0.4596	0.060*	0.505 (15)
C11'	0.9339 (4)	0.1640 (15)	0.4875 (6)	0.050 (4)	0.505 (15)
H11B	0.9373	0.0735	0.4553	0.060*	0.505 (15)
C22	0.6002 (8)	0.249 (3)	0.5056 (13)	0.057 (5)	0.50 (3)
H22A	0.5986	0.1425	0.4848	0.068*	0.50 (3)
C27	0.5722 (7)	0.251 (3)	0.5742 (11)	0.046 (4)	0.50 (3)
H27A	0.5767	0.3567	0.5959	0.056*	0.50 (3)
C22'	0.6023 (7)	0.322 (3)	0.5298 (11)	0.050 (5)	0.50 (3)
H22B	0.5981	0.4097	0.5631	0.060*	0.50 (3)
C27'	0.5723 (7)	0.183 (3)	0.5538 (12)	0.046 (4)	0.50 (3)
H27B	0.5773	0.0947	0.5214	0.055*	0.50 (3)
C7	0.8311 (3)	0.2486 (8)	0.3704 (4)	0.0646 (18)
H7A	0.8220	0.3590	0.3691	0.078*	0.495 (15)
H7B	0.8174	0.2133	0.3138	0.078*	0.495 (15)
H7C	0.8074	0.3414	0.3436	0.078*	0.505 (15)
H7D	0.8353	0.1818	0.3278	0.078*	0.505 (15)
C8	0.7908 (4)	0.1694 (14)	0.4093 (5)	0.129 (4)
H8A	0.7676	0.0857	0.3728	0.155*
H8B	0.7565	0.2421	0.4104	0.155*
C9	0.8204 (4)	0.1035 (12)	0.4915 (6)	0.113 (3)
H9A	0.8095	−0.0061	0.4868	0.136*
H9B	0.7973	0.1494	0.5244	0.136*
C10	0.8935 (3)	0.1169 (7)	0.5396 (4)	0.0586 (16)
H10A	0.9143	0.0165	0.5406	0.070*	0.495 (15)
H10B	0.9001	0.1440	0.5959	0.070*	0.495 (15)
H10C	0.9102	0.0181	0.5656	0.070*	0.505 (15)
H10D	0.9007	0.1930	0.5829	0.070*	0.505 (15)
C12	1.0435 (3)	0.2008 (6)	0.6084 (3)	0.0508 (14)
H12	1.0295	0.1614	0.6490	0.061*
C13	1.1108 (3)	0.2424 (6)	0.6237 (3)	0.0479 (14)
C14	1.1706 (3)	0.2436 (7)	0.6910 (4)	0.0601 (16)
H14	1.1770	0.2104	0.7439	0.072*
C15	1.2192 (3)	0.3041 (8)	0.6645 (4)	0.0642 (17)
H15	1.2644	0.3198	0.6963	0.077*
C16	1.1871 (3)	0.3367 (6)	0.5807 (4)	0.0514 (14)
H16	1.2082	0.3776	0.5472	0.062*
C17	0.3959 (4)	0.4642 (7)	0.2550 (4)	0.0617 (17)
H17	0.3508	0.4398	0.2417	0.074*
C18	0.4210 (4)	0.5572 (8)	0.2080 (4)	0.072 (2)
H18	0.3959	0.6039	0.1580	0.086*
C19	0.4893 (4)	0.5680 (7)	0.2480 (4)	0.071 (2)
H19	0.5191	0.6250	0.2317	0.085*
C20	0.5050 (4)	0.4761 (7)	0.3185 (4)	0.0573 (16)
C21	0.5638 (3)	0.4361 (7)	0.3859 (4)	0.0609 (17)
H21	0.6064	0.4702	0.3909	0.073*
C23	0.6741 (3)	0.3039 (9)	0.5423 (4)	0.0725 (19)
H23A	0.6960	0.2780	0.5042	0.087*	0.50 (3)
H23B	0.6747	0.4158	0.5477	0.087*	0.50 (3)
H23C	0.6779	0.2379	0.4992	0.087*	0.50 (3)
H23D	0.6929	0.4044	0.5380	0.087*	0.50 (3)
C24	0.7123 (4)	0.2366 (13)	0.6217 (6)	0.127 (4)
H24A	0.7394	0.3196	0.6553	0.153*
H24B	0.7434	0.1636	0.6128	0.153*
C25	0.6814 (4)	0.1572 (11)	0.6722 (5)	0.103 (3)
H25A	0.6971	0.2081	0.7255	0.124*
H25B	0.6993	0.0525	0.6812	0.124*
C26	0.6071 (3)	0.1450 (7)	0.6440 (4)	0.0592 (16)
H26A	0.5932	0.1695	0.6896	0.071*	0.50 (3)
H26B	0.5937	0.0391	0.6273	0.071*	0.50 (3)
H26C	0.5911	0.2148	0.6764	0.071*	0.50 (3)
H26D	0.5951	0.0402	0.6535	0.071*	0.50 (3)
C28	0.4559 (3)	0.1853 (6)	0.5596 (3)	0.0461 (13)
H28	0.4685	0.1472	0.6129	0.055*
C29	0.3878 (3)	0.2089 (6)	0.5076 (3)	0.0439 (13)
C30	0.3251 (3)	0.1884 (7)	0.5121 (4)	0.0581 (15)
H30	0.3162	0.1509	0.5570	0.070*
C31	0.2781 (3)	0.2348 (7)	0.4368 (4)	0.0603 (16)
H31	0.2315	0.2333	0.4212	0.072*
C32	0.3138 (3)	0.2840 (7)	0.3890 (4)	0.0544 (15)
H32	0.2943	0.3225	0.3357	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0458 (4)	0.0390 (4)	0.0391 (4)	0.0018 (3)	0.0154 (3)	−0.0003 (3)
Ni2	0.0506 (4)	0.0389 (4)	0.0453 (4)	−0.0012 (3)	0.0233 (3)	−0.0032 (3)
N1	0.053 (3)	0.047 (3)	0.040 (2)	0.003 (2)	0.018 (2)	0.002 (2)
N2	0.047 (3)	0.051 (3)	0.040 (2)	0.000 (2)	0.011 (2)	−0.003 (2)
N3	0.045 (3)	0.051 (3)	0.046 (3)	0.006 (2)	0.019 (2)	0.006 (2)
N4	0.046 (3)	0.043 (3)	0.047 (3)	0.004 (2)	0.016 (2)	0.001 (2)
N5	0.071 (3)	0.041 (3)	0.049 (3)	0.000 (2)	0.033 (3)	−0.006 (2)
N6	0.060 (3)	0.052 (3)	0.054 (3)	−0.001 (2)	0.035 (3)	−0.004 (2)
N7	0.041 (2)	0.043 (3)	0.050 (3)	−0.002 (2)	0.016 (2)	−0.001 (2)
N8	0.046 (3)	0.040 (3)	0.047 (3)	−0.002 (2)	0.019 (2)	−0.002 (2)
C1	0.062 (4)	0.054 (4)	0.057 (4)	0.003 (3)	0.028 (3)	0.002 (3)
C2	0.095 (5)	0.060 (4)	0.059 (4)	−0.008 (4)	0.045 (4)	0.004 (3)
C3	0.086 (5)	0.055 (4)	0.043 (3)	0.004 (4)	0.024 (3)	0.005 (3)
C4	0.063 (4)	0.039 (3)	0.043 (3)	0.004 (3)	0.020 (3)	−0.002 (3)
C5	0.059 (4)	0.048 (3)	0.045 (3)	0.010 (3)	0.006 (3)	−0.003 (3)
C6	0.049 (8)	0.037 (8)	0.052 (8)	0.000 (6)	0.016 (6)	−0.007 (6)
C11	0.044 (7)	0.046 (8)	0.061 (9)	0.010 (6)	0.031 (6)	0.000 (7)
C6'	0.056 (8)	0.054 (9)	0.047 (8)	−0.004 (7)	0.027 (6)	−0.006 (7)
C11'	0.051 (8)	0.050 (9)	0.060 (9)	0.006 (6)	0.033 (7)	0.007 (7)
C22	0.061 (9)	0.055 (10)	0.064 (10)	−0.019 (8)	0.035 (8)	−0.023 (8)
C27	0.044 (7)	0.047 (10)	0.053 (9)	−0.002 (7)	0.023 (6)	−0.021 (7)
C22'	0.040 (7)	0.062 (12)	0.045 (8)	−0.010 (7)	0.013 (6)	−0.017 (8)
C27'	0.049 (7)	0.036 (10)	0.053 (9)	0.006 (7)	0.019 (6)	−0.011 (7)
C7	0.044 (3)	0.071 (4)	0.074 (4)	0.002 (3)	0.017 (3)	−0.005 (3)
C8	0.057 (5)	0.217 (12)	0.108 (7)	−0.036 (7)	0.025 (5)	0.017 (8)
C9	0.072 (6)	0.139 (9)	0.142 (8)	−0.019 (5)	0.055 (6)	0.032 (7)
C10	0.062 (4)	0.054 (4)	0.068 (4)	−0.006 (3)	0.034 (3)	−0.008 (3)
C12	0.063 (4)	0.043 (3)	0.050 (3)	0.010 (3)	0.026 (3)	0.002 (3)
C13	0.059 (4)	0.043 (3)	0.042 (3)	0.009 (3)	0.019 (3)	0.003 (2)
C14	0.063 (4)	0.064 (4)	0.044 (3)	0.003 (3)	0.008 (3)	0.006 (3)
C15	0.054 (4)	0.060 (4)	0.062 (4)	0.005 (3)	0.003 (3)	0.002 (3)
C16	0.048 (3)	0.046 (3)	0.059 (4)	0.003 (3)	0.018 (3)	−0.002 (3)
C17	0.090 (5)	0.048 (4)	0.051 (4)	0.006 (3)	0.030 (4)	−0.003 (3)
C18	0.114 (6)	0.056 (4)	0.051 (4)	0.004 (4)	0.036 (4)	0.002 (3)
C19	0.117 (6)	0.044 (4)	0.078 (5)	0.001 (4)	0.067 (5)	0.001 (3)
C20	0.088 (5)	0.043 (3)	0.056 (4)	0.003 (3)	0.044 (4)	−0.004 (3)
C21	0.071 (4)	0.051 (4)	0.082 (5)	−0.013 (3)	0.053 (4)	−0.014 (3)
C23	0.049 (4)	0.081 (5)	0.091 (5)	−0.009 (4)	0.030 (4)	−0.020 (4)
C24	0.053 (5)	0.170 (10)	0.138 (9)	−0.011 (6)	0.011 (5)	0.045 (8)
C25	0.061 (5)	0.136 (8)	0.092 (6)	0.015 (5)	0.004 (4)	0.012 (6)
C26	0.060 (4)	0.052 (4)	0.058 (4)	0.005 (3)	0.012 (3)	−0.010 (3)
C28	0.049 (3)	0.040 (3)	0.049 (3)	−0.002 (3)	0.017 (3)	0.009 (3)
C29	0.047 (3)	0.041 (3)	0.046 (3)	0.000 (2)	0.020 (3)	−0.002 (2)
C30	0.056 (4)	0.059 (4)	0.068 (4)	−0.005 (3)	0.033 (3)	−0.006 (3)
C31	0.044 (3)	0.062 (4)	0.075 (4)	−0.001 (3)	0.022 (3)	−0.003 (3)
C32	0.046 (3)	0.051 (4)	0.057 (4)	0.000 (3)	0.010 (3)	−0.006 (3)

Geometric parameters (Å, º) top

Ni1—N2	1.850 (4)	C27'—H27B	0.9800
Ni1—N3	1.855 (4)	C7—C8	1.452 (10)
Ni1—N1	1.887 (4)	C7—H7A	0.9700
Ni1—N4	1.889 (4)	C7—H7B	0.9700
Ni2—N6	1.844 (5)	C7—H7C	0.9700
Ni2—N7	1.851 (4)	C7—H7D	0.9700
Ni2—N8	1.883 (4)	C8—C9	1.454 (8)
Ni2—N5	1.888 (5)	C8—H8A	0.9700
N1—C1	1.347 (7)	C8—H8B	0.9700
N1—C4	1.387 (7)	C9—C10	1.481 (9)
N2—C5	1.290 (7)	C9—H9A	0.9700
N2—C6	1.466 (8)	C9—H9B	0.9700
N2—C6'	1.470 (8)	C10—H10A	0.9700
N3—C12	1.297 (7)	C10—H10B	0.9700
N3—C11	1.466 (8)	C10—H10C	0.9700
N3—C11'	1.477 (9)	C10—H10D	0.9700
N4—C16	1.340 (7)	C12—C13	1.410 (8)
N4—C13	1.390 (7)	C12—H12	0.9300
N5—C17	1.351 (7)	C13—C14	1.379 (8)
N5—C20	1.378 (7)	C14—C15	1.388 (9)
N6—C21	1.297 (7)	C14—H14	0.9300
N6—C22	1.480 (18)	C15—C16	1.396 (8)
N6—C22'	1.543 (16)	C15—H15	0.9300
N7—C28	1.274 (6)	C16—H16	0.9300
N7—C27	1.503 (15)	C17—C18	1.391 (9)
N7—C27'	1.504 (15)	C17—H17	0.9300
N8—C32	1.345 (7)	C18—C19	1.368 (10)
N8—C29	1.394 (6)	C18—H18	0.9300
C1—C2	1.374 (8)	C19—C20	1.397 (9)
C1—H1	0.9300	C19—H19	0.9300
C2—C3	1.378 (9)	C20—C21	1.412 (9)
C2—H2	0.9300	C21—H21	0.9300
C3—C4	1.387 (8)	C23—C24	1.446 (10)
C3—H3	0.9300	C23—H23A	0.9700
C4—C5	1.423 (8)	C23—H23B	0.9700
C5—H5	0.9300	C23—H23C	0.9700
C6—C7	1.521 (9)	C23—H23D	0.9700
C6—C11	1.523 (9)	C24—C25	1.454 (8)
C6—H6A	0.9800	C24—H24A	0.9700
C11—C10	1.520 (9)	C24—H24B	0.9700
C11—H11A	0.9800	C25—C26	1.484 (9)
C6'—C7	1.507 (9)	C25—H25A	0.9700
C6'—C11'	1.520 (9)	C25—H25B	0.9700
C6'—H6B	0.9800	C26—H26A	0.9700
C11'—C10	1.523 (8)	C26—H26B	0.9700
C11'—H11B	0.9800	C26—H26C	0.9700
C22—C27	1.53 (3)	C26—H26D	0.9700
C22—C23	1.545 (17)	C28—C29	1.417 (7)
C22—H22A	0.9800	C28—H28	0.9300
C27—C26	1.485 (18)	C29—C30	1.383 (7)
C27—H27A	0.9800	C30—C31	1.388 (8)
C22'—C23	1.477 (15)	C30—H30	0.9300
C22'—C27'	1.49 (3)	C31—C32	1.389 (8)
C22'—H22B	0.9800	C31—H31	0.9300
C27'—C26	1.511 (18)	C32—H32	0.9300

N2—Ni1—N3	84.00 (19)	C7—C8—C9	122.0 (7)
N2—Ni1—N1	84.78 (19)	C7—C8—H8A	106.8
N3—Ni1—N1	168.47 (19)	C9—C8—H8A	106.8
N2—Ni1—N4	167.79 (19)	C7—C8—H8B	106.8
N3—Ni1—N4	84.49 (19)	C9—C8—H8B	106.8
N1—Ni1—N4	106.5 (2)	H8A—C8—H8B	106.7
N6—Ni2—N7	84.9 (2)	C8—C9—C10	120.8 (6)
N6—Ni2—N8	168.2 (2)	C8—C9—H9A	107.1
N7—Ni2—N8	84.12 (19)	C10—C9—H9A	107.1
N6—Ni2—N5	84.3 (2)	C8—C9—H9B	107.1
N7—Ni2—N5	169.0 (2)	C10—C9—H9B	107.1
N8—Ni2—N5	106.4 (2)	H9A—C9—H9B	106.8
C1—N1—C4	106.2 (5)	C9—C10—C11	114.4 (6)
C1—N1—Ni1	142.4 (4)	C9—C10—C11'	113.2 (6)
C4—N1—Ni1	111.2 (4)	C11—C10—C11'	27.7 (5)
C5—N2—C6	131.7 (6)	C9—C10—H10A	108.7
C5—N2—C6'	125.4 (6)	C11—C10—H10A	108.7
C6—N2—C6'	27.4 (5)	C11'—C10—H10A	83.8
C5—N2—Ni1	114.9 (4)	C9—C10—H10B	108.7
C6—N2—Ni1	112.9 (4)	C11—C10—H10B	108.7
C6'—N2—Ni1	114.9 (4)	C11'—C10—H10B	129.9
C12—N3—C11	124.8 (6)	H10A—C10—H10B	107.6
C12—N3—C11'	131.3 (6)	C9—C10—H10C	108.9
C11—N3—C11'	28.7 (5)	C11—C10—H10C	128.6
C12—N3—Ni1	115.7 (4)	C11'—C10—H10C	108.9
C11—N3—Ni1	114.8 (4)	H10A—C10—H10C	28.4
C11'—N3—Ni1	112.3 (4)	H10B—C10—H10C	81.1
C16—N4—C13	106.7 (5)	C9—C10—H10D	108.9
C16—N4—Ni1	142.2 (4)	C11—C10—H10D	83.3
C13—N4—Ni1	110.8 (4)	C11'—C10—H10D	109.0
C17—N5—C20	106.2 (5)	H10A—C10—H10D	130.6
C17—N5—Ni2	142.1 (5)	H10B—C10—H10D	28.8
C20—N5—Ni2	111.3 (4)	H10C—C10—H10D	107.7
C21—N6—C22	131.0 (8)	N3—C12—C13	114.4 (5)
C21—N6—C22'	126.6 (8)	N3—C12—H12	122.8
C22—N6—C22'	28.7 (6)	C13—C12—H12	122.8
C21—N6—Ni2	115.7 (4)	C14—C13—N4	109.4 (5)
C22—N6—Ni2	112.3 (6)	C14—C13—C12	136.3 (6)
C22'—N6—Ni2	113.8 (6)	N4—C13—C12	114.3 (5)
C28—N7—C27	125.3 (8)	C13—C14—C15	106.9 (5)
C28—N7—C27'	130.8 (8)	C13—C14—H14	126.5
C27—N7—C27'	26.2 (5)	C15—C14—H14	126.5
C28—N7—Ni2	116.5 (4)	C14—C15—C16	106.7 (5)
C27—N7—Ni2	114.5 (7)	C14—C15—H15	126.7
C27'—N7—Ni2	112.1 (7)	C16—C15—H15	126.7
C32—N8—C29	106.1 (5)	N4—C16—C15	110.3 (6)
C32—N8—Ni2	142.5 (4)	N4—C16—H16	124.9
C29—N8—Ni2	111.2 (3)	C15—C16—H16	124.9
N1—C1—C2	110.6 (6)	N5—C17—C18	109.9 (6)
N1—C1—H1	124.7	N5—C17—H17	125.1
C2—C1—H1	124.7	C18—C17—H17	125.1
C1—C2—C3	107.4 (6)	C19—C18—C17	107.9 (6)
C1—C2—H2	126.3	C19—C18—H18	126.0
C3—C2—H2	126.3	C17—C18—H18	126.0
C2—C3—C4	106.6 (6)	C18—C19—C20	106.0 (6)
C2—C3—H3	126.7	C18—C19—H19	127.0
C4—C3—H3	126.7	C20—C19—H19	127.0
N1—C4—C3	109.2 (5)	N5—C20—C19	109.9 (6)
N1—C4—C5	112.9 (5)	N5—C20—C21	113.7 (5)
C3—C4—C5	137.9 (6)	C19—C20—C21	136.4 (7)
N2—C5—C4	115.5 (5)	N6—C21—C20	114.5 (6)
N2—C5—H5	122.2	N6—C21—H21	122.7
C4—C5—H5	122.2	C20—C21—H21	122.7
N2—C6—C7	117.1 (7)	C24—C23—C22'	111.7 (8)
N2—C6—C11	104.3 (7)	C24—C23—C22	113.7 (9)
C7—C6—C11	112.4 (8)	C22'—C23—C22	28.7 (6)
N2—C6—H6A	107.5	C24—C23—H23A	108.8
C7—C6—H6A	107.5	C22'—C23—H23A	131.4
C11—C6—H6A	107.5	C22—C23—H23A	108.8
N3—C11—C10	117.0 (7)	C24—C23—H23B	108.8
N3—C11—C6	102.5 (7)	C22'—C23—H23B	83.5
C10—C11—C6	110.3 (8)	C22—C23—H23B	108.8
N3—C11—H11A	108.9	H23A—C23—H23B	107.7
C10—C11—H11A	108.9	C24—C23—H23C	109.3
C6—C11—H11A	108.9	C22'—C23—H23C	109.1
N2—C6'—C7	117.8 (7)	C22—C23—H23C	82.1
N2—C6'—C11'	102.2 (7)	H23A—C23—H23C	30.0
C7—C6'—C11'	111.0 (8)	H23B—C23—H23C	131.1
N2—C6'—H6B	108.5	C24—C23—H23D	109.3
C7—C6'—H6B	108.5	C22'—C23—H23D	109.4
C11'—C6'—H6B	108.5	C22—C23—H23D	129.2
N3—C11'—C6'	103.8 (7)	H23A—C23—H23D	80.4
N3—C11'—C10	116.1 (7)	H23B—C23—H23D	29.2
C6'—C11'—C10	112.5 (8)	H23C—C23—H23D	107.9
N3—C11'—H11B	108.0	C23—C24—C25	123.4 (7)
C6'—C11'—H11B	108.0	C23—C24—H24A	106.5
C10—C11'—H11B	108.0	C25—C24—H24A	106.5
N6—C22—C27	104.5 (15)	C23—C24—H24B	106.5
N6—C22—C23	115.8 (12)	C25—C24—H24B	106.5
C27—C22—C23	108.0 (17)	H24A—C24—H24B	106.5
N6—C22—H22A	109.4	C24—C25—C26	120.2 (7)
C27—C22—H22A	109.4	C24—C25—H25A	107.3
C23—C22—H22A	109.4	C26—C25—H25A	107.3
C26—C27—N7	116.6 (13)	C24—C25—H25B	107.3
C26—C27—C22	114.5 (17)	C26—C25—H25B	107.3
N7—C27—C22	101.9 (14)	H25A—C25—H25B	106.9
C26—C27—H27A	107.8	C25—C26—C27	112.3 (8)
N7—C27—H27A	107.8	C25—C26—C27'	112.6 (8)
C22—C27—H27A	107.8	C27—C26—C27'	26.3 (5)
C23—C22'—C27'	114.1 (17)	C25—C26—H26A	109.1
C23—C22'—N6	116.1 (12)	C27—C26—H26A	109.1
C27'—C22'—N6	101.8 (15)	C27'—C26—H26A	128.9
C23—C22'—H22B	108.2	C25—C26—H26B	109.1
C27'—C22'—H22B	108.2	C27—C26—H26B	109.1
N6—C22'—H22B	108.2	C27'—C26—H26B	85.1
C22'—C27'—N7	104.7 (14)	H26A—C26—H26B	107.9
C22'—C27'—C26	111.9 (17)	C25—C26—H26C	109.1
N7—C27'—C26	115.0 (12)	C27—C26—H26C	85.4
C22'—C27'—H27B	108.3	C27'—C26—H26C	109.3
N7—C27'—H27B	108.3	H26A—C26—H26C	26.6
C26—C27'—H27B	108.3	H26B—C26—H26C	129.2
C8—C7—C6'	114.9 (6)	C25—C26—H26D	109.1
C8—C7—C6	113.9 (7)	C27—C26—H26D	128.9
C6'—C7—C6	26.5 (5)	C27'—C26—H26D	108.9
C8—C7—H7A	108.8	H26A—C26—H26D	83.3
C6'—C7—H7A	84.2	H26B—C26—H26D	26.7
C6—C7—H7A	108.8	H26C—C26—H26D	107.8
C8—C7—H7B	108.8	N7—C28—C29	114.6 (5)
C6'—C7—H7B	127.8	N7—C28—H28	122.7
C6—C7—H7B	108.8	C29—C28—H28	122.7
H7A—C7—H7B	107.7	C30—C29—N8	109.6 (5)
C8—C7—H7C	108.5	C30—C29—C28	137.1 (5)
C6'—C7—H7C	108.5	N8—C29—C28	113.3 (5)
C6—C7—H7C	128.9	C29—C30—C31	106.6 (5)
H7A—C7—H7C	27.7	C29—C30—H30	126.7
H7B—C7—H7C	82.1	C31—C30—H30	126.7
C8—C7—H7D	108.5	C30—C31—C32	107.0 (5)
C6'—C7—H7D	108.6	C30—C31—H31	126.5
C6—C7—H7D	84.9	C32—C31—H31	126.5
H7A—C7—H7D	129.8	N8—C32—C31	110.6 (5)
H7B—C7—H7D	27.3	N8—C32—H32	124.7
H7C—C7—H7D	107.5	C31—C32—H32	124.7

N2—Ni1—N1—C1	−179.6 (7)	C28—N7—C27—C26	42 (2)
N3—Ni1—N1—C1	167.3 (8)	C27'—N7—C27—C26	−70 (3)
N4—Ni1—N1—C1	5.2 (7)	Ni2—N7—C27—C26	−161.0 (11)
N2—Ni1—N1—C4	7.0 (4)	C28—N7—C27—C22	167.2 (13)
N3—Ni1—N1—C4	−6.1 (12)	C27'—N7—C27—C22	55 (2)
N4—Ni1—N1—C4	−168.2 (3)	Ni2—N7—C27—C22	−36 (2)
N3—Ni1—N2—C5	169.7 (4)	N6—C22—C27—C26	174.1 (9)
N1—Ni1—N2—C5	−7.7 (4)	C23—C22—C27—C26	−62 (3)
N4—Ni1—N2—C5	150.1 (8)	N6—C22—C27—N7	47 (2)
N3—Ni1—N2—C6	−17.1 (6)	C23—C22—C27—N7	171.2 (10)
N1—Ni1—N2—C6	165.5 (6)	C21—N6—C22'—C23	−41 (2)
N4—Ni1—N2—C6	−36.7 (12)	C22—N6—C22'—C23	69 (2)
N3—Ni1—N2—C6'	12.8 (7)	Ni2—N6—C22'—C23	162.1 (12)
N1—Ni1—N2—C6'	−164.6 (7)	C21—N6—C22'—C27'	−165.9 (12)
N4—Ni1—N2—C6'	−6.8 (13)	C22—N6—C22'—C27'	−56 (2)
N2—Ni1—N3—C12	−170.2 (4)	Ni2—N6—C22'—C27'	38 (2)
N1—Ni1—N3—C12	−157.0 (9)	C23—C22'—C27'—N7	−173.9 (9)
N4—Ni1—N3—C12	5.7 (4)	N6—C22'—C27'—N7	−48 (2)
N2—Ni1—N3—C11	−13.1 (6)	C23—C22'—C27'—C26	61 (3)
N1—Ni1—N3—C11	0.1 (13)	N6—C22'—C27'—C26	−173.3 (9)
N4—Ni1—N3—C11	162.8 (6)	C28—N7—C27'—C22'	−145.7 (13)
N2—Ni1—N3—C11'	18.2 (6)	C27—N7—C27'—C22'	−57 (3)
N1—Ni1—N3—C11'	31.3 (13)	Ni2—N7—C27'—C22'	44 (2)
N4—Ni1—N3—C11'	−165.9 (6)	C28—N7—C27'—C26	−22 (2)
N2—Ni1—N4—C16	−157.8 (8)	C27—N7—C27'—C26	66 (3)
N3—Ni1—N4—C16	−177.4 (6)	Ni2—N7—C27'—C26	166.7 (11)
N1—Ni1—N4—C16	−1.0 (7)	N2—C6'—C7—C8	160.8 (9)
N2—Ni1—N4—C13	14.6 (11)	C11'—C6'—C7—C8	43.5 (12)
N3—Ni1—N4—C13	−5.0 (4)	N2—C6'—C7—C6	66.9 (12)
N1—Ni1—N4—C13	171.5 (4)	C11'—C6'—C7—C6	−50.4 (12)
N6—Ni2—N5—C17	−177.9 (7)	N2—C6—C7—C8	−164.8 (9)
N7—Ni2—N5—C17	−166.6 (9)	C11—C6—C7—C8	−44.0 (12)
N8—Ni2—N5—C17	−3.0 (7)	N2—C6—C7—C6'	−66.4 (12)
N6—Ni2—N5—C20	−6.2 (4)	C11—C6—C7—C6'	54.3 (12)
N7—Ni2—N5—C20	5.1 (12)	C6'—C7—C8—C9	−15.5 (15)
N8—Ni2—N5—C20	168.7 (4)	C6—C7—C8—C9	13.7 (15)
N7—Ni2—N6—C21	−171.0 (4)	C7—C8—C9—C10	0.9 (17)
N8—Ni2—N6—C21	−148.9 (9)	C8—C9—C10—C11	15.0 (14)
N5—Ni2—N6—C21	6.8 (4)	C8—C9—C10—C11'	−15.3 (14)
N7—Ni2—N6—C22	19.3 (11)	N3—C11—C10—C9	−160.8 (8)
N8—Ni2—N6—C22	41.4 (16)	C6—C11—C10—C9	−44.3 (11)
N5—Ni2—N6—C22	−162.9 (11)	N3—C11—C10—C11'	−66.9 (11)
N7—Ni2—N6—C22'	−11.9 (11)	C6—C11—C10—C11'	49.7 (11)
N8—Ni2—N6—C22'	10.2 (16)	N3—C11'—C10—C9	163.4 (8)
N5—Ni2—N6—C22'	165.9 (11)	C6'—C11'—C10—C9	44.0 (12)
N6—Ni2—N7—C28	170.0 (4)	N3—C11'—C10—C11	64.8 (12)
N8—Ni2—N7—C28	−5.5 (4)	C6'—C11'—C10—C11	−54.5 (12)
N5—Ni2—N7—C28	158.7 (9)	C11—N3—C12—C13	−159.5 (7)
N6—Ni2—N7—C27	10.8 (11)	C11'—N3—C12—C13	164.7 (8)
N8—Ni2—N7—C27	−164.8 (11)	Ni1—N3—C12—C13	−5.0 (6)
N5—Ni2—N7—C27	−0.5 (16)	C16—N4—C13—C14	0.1 (6)
N6—Ni2—N7—C27'	−17.7 (10)	Ni1—N4—C13—C14	−175.1 (4)
N8—Ni2—N7—C27'	166.7 (10)	C16—N4—C13—C12	178.9 (5)
N5—Ni2—N7—C27'	−29.0 (15)	Ni1—N4—C13—C12	3.7 (6)
N6—Ni2—N8—C32	156.7 (9)	N3—C12—C13—C14	179.0 (6)
N7—Ni2—N8—C32	178.9 (6)	N3—C12—C13—N4	0.7 (7)
N5—Ni2—N8—C32	2.0 (7)	N4—C13—C14—C15	0.3 (7)
N6—Ni2—N8—C29	−17.4 (12)	C12—C13—C14—C15	−178.1 (6)
N7—Ni2—N8—C29	4.8 (4)	C13—C14—C15—C16	−0.5 (7)
N5—Ni2—N8—C29	−172.1 (3)	C13—N4—C16—C15	−0.4 (6)
C4—N1—C1—C2	0.7 (7)	Ni1—N4—C16—C15	172.2 (5)
Ni1—N1—C1—C2	−172.9 (5)	C14—C15—C16—N4	0.6 (7)
N1—C1—C2—C3	0.1 (7)	C20—N5—C17—C18	−0.4 (6)
C1—C2—C3—C4	−0.9 (7)	Ni2—N5—C17—C18	171.5 (5)
C1—N1—C4—C3	−1.3 (6)	N5—C17—C18—C19	−0.9 (7)
Ni1—N1—C4—C3	174.5 (4)	C17—C18—C19—C20	1.9 (7)
C1—N1—C4—C5	178.8 (5)	C17—N5—C20—C19	1.6 (6)
Ni1—N1—C4—C5	−5.4 (6)	Ni2—N5—C20—C19	−173.1 (4)
C2—C3—C4—N1	1.4 (7)	C17—N5—C20—C21	179.6 (5)
C2—C3—C4—C5	−178.7 (7)	Ni2—N5—C20—C21	4.9 (6)
C6—N2—C5—C4	−165.1 (8)	C18—C19—C20—N5	−2.2 (7)
C6'—N2—C5—C4	160.6 (7)	C18—C19—C20—C21	−179.5 (7)
Ni1—N2—C5—C4	6.5 (6)	C22—N6—C21—C20	161.6 (14)
N1—C4—C5—N2	−0.5 (7)	C22'—N6—C21—C20	−161.8 (13)
C3—C4—C5—N2	179.6 (7)	Ni2—N6—C21—C20	−5.7 (7)
C5—N2—C6—C7	−22.2 (14)	N5—C20—C21—N6	0.4 (7)
C6'—N2—C6—C7	65.9 (12)	C19—C20—C21—N6	177.6 (7)
Ni1—N2—C6—C7	166.1 (6)	C27'—C22'—C23—C24	−46 (3)
C5—N2—C6—C11	−147.1 (8)	N6—C22'—C23—C24	−163.4 (13)
C6'—N2—C6—C11	−59.0 (12)	C27'—C22'—C23—C22	55 (3)
Ni1—N2—C6—C11	41.2 (9)	N6—C22'—C23—C22	−63 (2)
C12—N3—C11—C10	−47.1 (12)	N6—C22—C23—C24	160.6 (13)
C11'—N3—C11—C10	66.8 (12)	C27—C22—C23—C24	44 (2)
Ni1—N3—C11—C10	158.2 (6)	N6—C22—C23—C22'	68 (2)
C12—N3—C11—C6	−167.9 (7)	C27—C22—C23—C22'	−48 (2)
C11'—N3—C11—C6	−54.0 (11)	C22'—C23—C24—C25	16.1 (18)
Ni1—N3—C11—C6	37.4 (9)	C22—C23—C24—C25	−15.0 (17)
N2—C6—C11—N3	−47.1 (10)	C23—C24—C25—C26	−1.5 (16)
C7—C6—C11—N3	−175.0 (7)	C24—C25—C26—C27	−13.7 (15)
N2—C6—C11—C10	−172.5 (7)	C24—C25—C26—C27'	14.8 (15)
C7—C6—C11—C10	59.7 (12)	N7—C27—C26—C25	165.2 (11)
C5—N2—C6'—C7	45.8 (13)	C22—C27—C26—C25	46 (2)
C6—N2—C6'—C7	−67.9 (13)	N7—C27—C26—C27'	69 (2)
Ni1—N2—C6'—C7	−160.1 (7)	C22—C27—C26—C27'	−50 (2)
C5—N2—C6'—C11'	167.7 (7)	C22'—C27'—C26—C25	−43 (2)
C6—N2—C6'—C11'	54.0 (12)	N7—C27'—C26—C25	−162.2 (11)
Ni1—N2—C6'—C11'	−38.1 (10)	C22'—C27'—C26—C27	52 (3)
C12—N3—C11'—C6'	147.2 (8)	N7—C27'—C26—C27	−67 (2)
C11—N3—C11'—C6'	58.5 (12)	C27—N7—C28—C29	161.5 (12)
Ni1—N3—C11'—C6'	−42.8 (10)	C27'—N7—C28—C29	−165.7 (13)
C12—N3—C11'—C10	23.2 (14)	Ni2—N7—C28—C29	4.8 (6)
C11—N3—C11'—C10	−65.5 (12)	C32—N8—C29—C30	0.3 (6)
Ni1—N3—C11'—C10	−166.8 (7)	Ni2—N8—C29—C30	176.5 (4)
N2—C6'—C11'—N3	48.5 (10)	C32—N8—C29—C28	−179.9 (5)
C7—C6'—C11'—N3	174.9 (7)	Ni2—N8—C29—C28	−3.6 (6)
N2—C6'—C11'—C10	174.8 (7)	N7—C28—C29—C30	179.2 (6)
C7—C6'—C11'—C10	−58.8 (12)	N7—C28—C29—N8	−0.6 (7)
C21—N6—C22—C27	148.9 (11)	N8—C29—C30—C31	0.3 (7)
C22'—N6—C22—C27	56 (2)	C28—C29—C30—C31	−179.5 (6)
Ni2—N6—C22—C27	−43 (2)	C29—C30—C31—C32	−0.7 (7)
C21—N6—C22—C23	30 (2)	C29—N8—C32—C31	−0.7 (6)
C22'—N6—C22—C23	−63 (2)	Ni2—N8—C32—C31	−175.0 (5)
Ni2—N6—C22—C23	−162.1 (11)	C30—C31—C32—N8	0.9 (7)

Experimental details

Crystal data
Chemical formula	[Ni(C₁₆H₁₈N₄)]
M_r	325.05
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	21.379 (3), 8.6247 (10), 17.475 (2)
β (°)	111.697 (2)
V (Å³)	2993.9 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.29
Crystal size (mm)	0.26 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.730, 0.800
No. of measured, independent and observed [I > 2σ(I)] reflections	16412, 6100, 4081
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.136, 1.15
No. of reflections	6100
No. of parameters	418
No. of restraints	12
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + 10.3102P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.41

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXL97.

Selected geometric parameters (Å, º) top

Ni1—N2	1.850 (4)	Ni2—N6	1.844 (5)
Ni1—N3	1.855 (4)	Ni2—N7	1.851 (4)
Ni1—N1	1.887 (4)	Ni2—N8	1.883 (4)
Ni1—N4	1.889 (4)	Ni2—N5	1.888 (5)

N2—Ni1—N3	84.00 (19)	N6—Ni2—N7	84.9 (2)
N2—Ni1—N1	84.78 (19)	N7—Ni2—N8	84.12 (19)
N3—Ni1—N4	84.49 (19)	N6—Ni2—N5	84.3 (2)

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