Bis(thio­cyanato-κN)tetra­kis(1-vinyl-1H-imidazole-κN³)nickel(II)

The title compound, [Ni(NCS)₂(C₅H₆N₂)₄], crystallizes with two independent half-mol­ecules in the asymmetric unit; each Ni atom lies on a centre of symmetry. In both independent mol­ecules, each Ni^II ion displays a compressed octa­hedral coordination geometry, with six N atoms from two thio­cyanate anions and four 1-vinyl­imidazole ligands building the NiN₆ chromophore. In the crystal structure, π–π stacking inter­actions [centroid-to-centroid distance = 4.685 (3) Å] link the two independent mol­ecules into a one-dimensional chain running along the a axis. Inter­molecular C—H...S hydrogen bonds further stabilize the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.052
• wR factor = 0.198
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N8     -   C14     ..       5.63 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         14

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1         (2)       2.05
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni2         (2)       2.07
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

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

---

S1. Comment

The title compound, (I), crystallizes with two independent molecules in the asymmetric unit (Fig. 1). In the two independent molecules, each Ni^II ion, which are located on crystallographic centres of symmetry, displays a compressed octahedral coordination geometry, with six N atoms from two thiocyanate anions and four 1-vinylimidazole ligands building the NiN₆ chromophore. The equatorial planes in the two independent molecules are formed by four Ni—N(1-vinylimadazole) bonds with lengths ranging from 2.106 (5) to 2.118 (6) Å, and the axial positions are occupied by two N-bonded NCS groups [Ni—N(NCS) = 2.067 (6) and 2.065 (5) Å]. These values agree well with those observed in [Ni(NCS)₂(1-methylimidazole)₄] (Liu et al., 2005) and [Ni(NCS)₂(1-ethylimidazole)₄] (Liu et al., 2006). In the crystal, the distance of 4.685 (3)Å of Cg1···Cg1 [Cg1 is centroids of N9–N10/C18–C20; symmetry code: 1-X,-Y,1-Z] shows a presence of π···π stacking interactions which link the two independent molecules into 1-D chain running along the a axis. Intermolecular C—H···S hydrogen bonds further stabilize the crystal structure.

Related literature

For related literature, see: Liu et al. (2005, 2006).

S2. Experimental

The title compound was prepared by the reaction of 1-vinylimidazole (1.88 g, 20 mmol) with NiCl₂.6H₂O(1.19 g, 5 mmol) and potassium thiocyanate (0.98 g, 10 mmol) by means of hydrothermal synthesis in a stainless-steel reactor with Teflon liner at 383 K for 24 h. Single crystals suitable for X-ray measurements were obtained by recrystallization from methanol at room temperature.

S3. Refinement

H atoms were positioned geometrically and allowed to ride on their attached atoms, with C—H distances = 0.93–0.96 Å, and with U_iso(H) = 1.2–1.5U_eq(C).

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The packing of (I), viewed down the b axis.

Bis(thiocyanato-κN)tetrakis(1-vinyl-1H-imidazole-κN³)nickel(II)

Crystal data

[Ni(NCS)2(C5H6N2)4]	Z = 2
Mr = 551.34	F(000) = 572
Triclinic, P1	Dx = 1.362 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6400 (19) Å	Cell parameters from 3253 reflections
b = 10.242 (2) Å	θ = 4–14°
c = 14.705 (3) Å	µ = 0.91 mm^−1
α = 109.46 (3)°	T = 293 K
β = 90.16 (3)°	Block, blue
γ = 100.16 (3)°	0.30 × 0.30 × 0.20 mm
V = 1344.5 (6) Å^3

Data collection

Bruker SMART 1K CCD area-detector diffractometer	5257 independent reflections
Radiation source: fine-focus sealed tube	3080 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
thin–slice ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = 0→11
Tmin = 0.773, Tmax = 0.839	k = −12→12
5593 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.198	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.1152P)^2 + 2.8055P] where P = (Fo^2 + 2Fc^2)/3
5257 reflections	(Δ/σ)max = 0.032
307 parameters	Δρmax = 0.66 e Å^−3
1 restraint	Δρmin = −1.65 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.5000	0.0000	0.0000	0.0496 (4)
S1	0.0867 (3)	0.2078 (3)	0.07754 (18)	0.0870 (8)
N1	0.3250 (7)	0.0951 (7)	0.0234 (4)	0.0646 (17)
N3	0.3709 (9)	−0.3102 (8)	0.1314 (6)	0.080 (2)
N2	0.4058 (6)	−0.1414 (7)	0.0687 (4)	0.0597 (16)
N5	0.7598 (6)	0.2755 (6)	0.2474 (4)	0.0493 (13)
N4	0.5948 (6)	0.1415 (6)	0.1351 (4)	0.0530 (14)
C6	0.3214 (10)	−0.4777 (10)	0.2129 (7)	0.085
H6A	0.2422	−0.4401	0.2361	0.102*
H6B	0.3430	−0.5524	0.2293	0.102*
C5	0.4024 (15)	−0.4254 (13)	0.1574 (9)	0.122 (4)
H5A	0.4815	−0.4634	0.1345	0.147*
C3	0.2604 (12)	−0.2492 (12)	0.1510 (8)	0.099 (3)
H3A	0.1837	−0.2739	0.1841	0.118*
C4	0.2797 (9)	−0.1443 (11)	0.1141 (7)	0.086 (3)
H4A	0.2178	−0.0827	0.1182	0.104*
C2	0.4563 (10)	−0.2409 (9)	0.0822 (7)	0.076 (2)
H2A	0.5425	−0.2637	0.0607	0.091*
C11	0.9296 (9)	0.4409 (8)	0.3719 (6)	0.068 (2)
H11A	0.8578	0.4784	0.4077	0.082*
H11B	1.0235	0.4767	0.3948	0.082*
C10	0.8991 (8)	0.3395 (8)	0.2904 (5)	0.0562 (18)
H10A	0.9740	0.3051	0.2569	0.067*
C8	0.6330 (8)	0.3001 (8)	0.2836 (5)	0.0569 (18)
H8A	0.6186	0.3615	0.3441	0.068*
C9	0.5329 (8)	0.2177 (8)	0.2143 (5)	0.0584 (19)
H9A	0.4361	0.2131	0.2194	0.070*
C7	0.7300 (8)	0.1789 (8)	0.1588 (5)	0.0566 (18)
H7A	0.7984	0.1424	0.1185	0.068*
C1	0.2269 (7)	0.1420 (8)	0.0464 (5)	0.0520 (17)
Ni2	0.0000	0.0000	0.5000	0.0402 (3)
S2	0.3353 (2)	0.3734 (2)	0.4538 (2)	0.0853 (8)
N6	0.1136 (6)	0.1787 (6)	0.4808 (5)	0.0547 (15)
N8	−0.1142 (8)	−0.2379 (10)	0.2048 (5)	0.086 (3)
N7	−0.0582 (6)	−0.0859 (6)	0.3503 (4)	0.0514 (14)
N10	0.3853 (6)	−0.1437 (6)	0.4179 (4)	0.0526 (14)
N9	0.1789 (5)	−0.0955 (5)	0.4706 (4)	0.0459 (13)
C17	−0.1907 (10)	−0.4674 (10)	0.1355 (8)	0.087
H17A	−0.1961	−0.4693	0.1982	0.104*
H17B	−0.2163	−0.5504	0.0831	0.104*
C16	−0.1493 (15)	−0.3543 (14)	0.1217 (11)	0.145 (5)
H16A	−0.1424	−0.3481	0.0601	0.174*
C14	−0.0759 (10)	−0.1120 (11)	0.1937 (7)	0.079 (3)
H14A	−0.0746	−0.0929	0.1361	0.095*
C15	−0.0403 (8)	−0.0209 (9)	0.2817 (5)	0.065 (2)
H15A	−0.0074	0.0751	0.2956	0.077*
C13	−0.1039 (9)	−0.2177 (9)	0.3013 (7)	0.074 (2)
H13A	−0.1265	−0.2886	0.3281	0.089*
C22	0.5619 (9)	−0.0592 (11)	0.3267 (7)	0.087 (3)
H22A	0.5062	−0.0005	0.3147	0.104*
H22B	0.6506	−0.0615	0.3022	0.104*
C21	0.5170 (8)	−0.1359 (9)	0.3762 (6)	0.067 (2)
H21A	0.5765	−0.1928	0.3862	0.080*
C19	0.3321 (9)	−0.2359 (8)	0.4646 (6)	0.065 (2)
H19A	0.3747	−0.3059	0.4733	0.079*
C20	0.2070 (8)	−0.2054 (8)	0.4953 (6)	0.0607 (19)
H20A	0.1478	−0.2527	0.5287	0.073*
C18	0.2891 (7)	−0.0618 (7)	0.4241 (5)	0.0493 (16)
H18A	0.2988	0.0108	0.3985	0.059*
C12	0.2049 (7)	0.2587 (6)	0.4678 (5)	0.0449 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0353 (7)	0.0620 (8)	0.0486 (8)	0.0122 (6)	0.0028 (5)	0.0136 (6)
S1	0.0682 (14)	0.123 (2)	0.0795 (16)	0.0500 (14)	0.0290 (12)	0.0312 (15)
N1	0.054 (4)	0.076 (5)	0.057 (4)	0.023 (3)	0.006 (3)	0.009 (3)
N3	0.090 (6)	0.069 (5)	0.082 (5)	−0.001 (4)	−0.009 (4)	0.034 (4)
N2	0.052 (4)	0.067 (4)	0.055 (4)	0.002 (3)	−0.005 (3)	0.019 (3)
N5	0.048 (3)	0.056 (3)	0.043 (3)	0.011 (3)	0.006 (3)	0.015 (3)
N4	0.045 (3)	0.062 (4)	0.047 (3)	0.010 (3)	0.003 (3)	0.011 (3)
C6	0.085	0.085	0.085	0.016	0.006	0.029
C5	0.046 (4)	0.065 (5)	0.039 (4)	0.011 (4)	0.001 (3)	0.010 (3)
C3	0.083 (7)	0.120 (9)	0.100 (8)	−0.003 (7)	0.003 (6)	0.058 (7)
C4	0.064 (6)	0.112 (8)	0.097 (7)	0.010 (5)	0.018 (5)	0.057 (6)
C2	0.069 (6)	0.072 (6)	0.086 (6)	0.010 (5)	−0.002 (5)	0.026 (5)
C11	0.072 (5)	0.063 (5)	0.061 (5)	0.006 (4)	−0.004 (4)	0.014 (4)
C10	0.055 (4)	0.058 (4)	0.048 (4)	0.005 (3)	0.003 (3)	0.011 (4)
C8	0.062 (5)	0.060 (4)	0.043 (4)	0.013 (4)	0.006 (3)	0.011 (3)
C9	0.052 (4)	0.075 (5)	0.050 (4)	0.020 (4)	0.006 (3)	0.020 (4)
C7	0.049 (4)	0.068 (5)	0.046 (4)	0.009 (3)	0.004 (3)	0.011 (4)
C1	0.046 (4)	0.065 (5)	0.039 (4)	0.011 (4)	0.001 (3)	0.010 (3)
Ni2	0.0363 (6)	0.0390 (6)	0.0454 (7)	−0.0030 (5)	−0.0010 (5)	0.0197 (5)
S2	0.0629 (13)	0.0617 (13)	0.134 (2)	−0.0008 (10)	0.0420 (14)	0.0422 (14)
N6	0.052 (3)	0.047 (3)	0.068 (4)	−0.002 (3)	0.004 (3)	0.029 (3)
N8	0.073 (4)	0.103 (5)	0.054 (3)	0.022 (3)	−0.020 (3)	−0.012 (3)
N7	0.049 (3)	0.053 (4)	0.052 (3)	0.005 (3)	−0.004 (3)	0.019 (3)
N10	0.043 (3)	0.054 (3)	0.059 (4)	0.012 (3)	0.002 (3)	0.017 (3)
N9	0.042 (3)	0.046 (3)	0.053 (3)	0.004 (2)	−0.001 (3)	0.022 (3)
C17	0.087	0.087	0.087	0.016	0.006	0.029
C16	0.148 (3)	0.067 (4)	0.037 (3)	0.009 (3)	0.000 (2)	0.010 (3)
C14	0.072 (6)	0.101 (8)	0.068 (6)	0.021 (5)	0.000 (5)	0.032 (6)
C15	0.067 (5)	0.080 (5)	0.050 (5)	0.014 (4)	−0.001 (4)	0.025 (4)
C13	0.069 (5)	0.067 (5)	0.075 (6)	0.003 (4)	−0.017 (4)	0.016 (5)
C22	0.053 (5)	0.124 (8)	0.080 (6)	0.009 (5)	0.002 (4)	0.033 (6)
C21	0.052 (5)	0.076 (5)	0.071 (5)	0.013 (4)	0.010 (4)	0.020 (5)
C19	0.072 (5)	0.055 (4)	0.084 (6)	0.028 (4)	0.015 (4)	0.035 (4)
C20	0.067 (5)	0.052 (4)	0.073 (5)	0.011 (4)	0.013 (4)	0.034 (4)
C18	0.049 (4)	0.054 (4)	0.045 (4)	0.002 (3)	0.001 (3)	0.022 (3)
C12	0.049 (4)	0.039 (3)	0.050 (4)	0.011 (3)	0.011 (3)	0.017 (3)

Geometric parameters (Å, º)

Ni1—N1^i	2.067 (6)	Ni2—N6^ii	2.065 (5)
Ni1—N1	2.067 (6)	Ni2—N6	2.065 (5)
Ni1—N2	2.111 (6)	Ni2—N9	2.106 (5)
Ni1—N2^i	2.111 (6)	Ni2—N9^ii	2.106 (5)
Ni1—N4^i	2.118 (6)	Ni2—N7	2.113 (6)
Ni1—N4	2.118 (6)	Ni2—N7^ii	2.113 (6)
S1—C1	1.615 (7)	S2—C12	1.626 (7)
N1—C1	1.138 (9)	N6—C12	1.155 (8)
N3—C3	1.313 (13)	N8—C14	1.341 (12)
N3—C2	1.358 (11)	N8—C13	1.366 (11)
N3—C5	1.434 (14)	N8—C16	1.383 (15)
N2—C2	1.276 (10)	N7—C13	1.294 (10)
N2—C4	1.388 (10)	N7—C15	1.378 (9)
N5—C7	1.341 (9)	N10—C18	1.340 (9)
N5—C8	1.366 (9)	N10—C19	1.375 (9)
N5—C10	1.429 (9)	N10—C21	1.413 (9)
N4—C7	1.303 (8)	N9—C18	1.321 (8)
N4—C9	1.373 (9)	N9—C20	1.361 (8)
C6—C5	1.308 (14)	C17—C16	1.240 (19)
C6—H6A	0.9300	C17—H17A	0.9300
C6—H6B	0.9300	C17—H17B	0.9300
C5—H5A	0.9300	C16—H16A	0.9300
C3—C4	1.343 (13)	C14—C15	1.320 (11)
C3—H3A	0.9300	C14—H14A	0.9300
C4—H4A	0.9300	C15—H15A	0.9300
C2—H2A	0.9300	C13—H13A	0.9300
C11—C10	1.288 (10)	C22—C21	1.264 (12)
C11—H11A	0.9300	C22—H22A	0.9300
C11—H11B	0.9300	C22—H22B	0.9300
C10—H10A	0.9300	C21—H21A	0.9300
C8—C9	1.348 (10)	C19—C20	1.340 (10)
C8—H8A	0.9300	C19—H19A	0.9300
C9—H9A	0.9300	C20—H20A	0.9300
C7—H7A	0.9300	C18—H18A	0.9300
N1^i—Ni1—N1	180.0 (3)	N6^ii—Ni2—N6	180.00 (18)
N1^i—Ni1—N2	90.5 (3)	N6^ii—Ni2—N9	90.4 (2)
N1—Ni1—N2	89.5 (3)	N6—Ni2—N9	89.6 (2)
N1^i—Ni1—N2^i	89.5 (3)	N6^ii—Ni2—N9^ii	89.6 (2)
N1—Ni1—N2^i	90.5 (3)	N6—Ni2—N9^ii	90.4 (2)
N2—Ni1—N2^i	180.0 (3)	N9—Ni2—N9^ii	180.0 (3)
N1^i—Ni1—N4^i	89.7 (2)	N6^ii—Ni2—N7	90.2 (2)
N1—Ni1—N4^i	90.3 (2)	N6—Ni2—N7	89.8 (2)
N2—Ni1—N4^i	90.2 (2)	N9—Ni2—N7	87.7 (2)
N2^i—Ni1—N4^i	89.8 (2)	N9^ii—Ni2—N7	92.3 (2)
N1^i—Ni1—N4	90.3 (2)	N6^ii—Ni2—N7^ii	89.8 (2)
N1—Ni1—N4	89.7 (2)	N6—Ni2—N7^ii	90.2 (2)
N2—Ni1—N4	89.8 (2)	N9—Ni2—N7^ii	92.3 (2)
N2^i—Ni1—N4	90.2 (2)	N9^ii—Ni2—N7^ii	87.7 (2)
N4^i—Ni1—N4	180.0 (2)	N7—Ni2—N7^ii	180.000 (1)
C1—N1—Ni1	171.2 (7)	C12—N6—Ni2	162.1 (6)
C3—N3—C2	107.0 (8)	C14—N8—C13	107.9 (7)
C3—N3—C5	128.4 (10)	C14—N8—C16	117.1 (9)
C2—N3—C5	124.6 (10)	C13—N8—C16	134.9 (10)
C2—N2—C4	103.6 (8)	C13—N7—C15	104.7 (7)
C2—N2—Ni1	127.3 (6)	C13—N7—Ni2	126.1 (6)
C4—N2—Ni1	129.0 (6)	C15—N7—Ni2	128.7 (5)
C7—N5—C8	106.2 (6)	C18—N10—C19	105.5 (6)
C7—N5—C10	124.8 (6)	C18—N10—C21	128.4 (7)
C8—N5—C10	128.9 (6)	C19—N10—C21	126.1 (7)
C7—N4—C9	104.8 (6)	C18—N9—C20	104.6 (6)
C7—N4—Ni1	125.7 (5)	C18—N9—Ni2	127.7 (5)
C9—N4—Ni1	129.4 (5)	C20—N9—Ni2	127.8 (5)
C5—C6—H6A	120.0	C16—C17—H17A	120.0
C5—C6—H6B	120.0	C16—C17—H17B	120.0
H6A—C6—H6B	120.0	H17A—C17—H17B	120.0
C6—C5—N3	120.9 (13)	C17—C16—N8	114.9 (13)
C6—C5—H5A	119.6	C17—C16—H16A	122.5
N3—C5—H5A	119.6	N8—C16—H16A	122.6
N3—C3—C4	106.6 (9)	C15—C14—N8	105.5 (8)
N3—C3—H3A	126.7	C15—C14—H14A	127.2
C4—C3—H3A	126.7	N8—C14—H14A	127.2
C3—C4—N2	109.9 (9)	C14—C15—N7	111.5 (8)
C3—C4—H4A	125.0	C14—C15—H15A	124.3
N2—C4—H4A	125.0	N7—C15—H15A	124.3
N2—C2—N3	112.8 (9)	N7—C13—N8	110.4 (8)
N2—C2—H2A	123.6	N7—C13—H13A	124.8
N3—C2—H2A	123.6	N8—C13—H13A	124.8
C10—C11—H11A	120.0	C21—C22—H22A	120.0
C10—C11—H11B	120.0	C21—C22—H22B	120.0
H11A—C11—H11B	120.0	H22A—C22—H22B	120.0
C11—C10—N5	125.5 (7)	C22—C21—N10	126.4 (9)
C11—C10—H10A	117.3	C22—C21—H21A	116.8
N5—C10—H10A	117.3	N10—C21—H21A	116.8
C9—C8—N5	106.4 (6)	C20—C19—N10	106.9 (6)
C9—C8—H8A	126.8	C20—C19—H19A	126.6
N5—C8—H8A	126.8	N10—C19—H19A	126.6
C8—C9—N4	109.9 (7)	C19—C20—N9	110.4 (7)
C8—C9—H9A	125.0	C19—C20—H20A	124.8
N4—C9—H9A	125.0	N9—C20—H20A	124.8
N4—C7—N5	112.7 (6)	N9—C18—N10	112.6 (6)
N4—C7—H7A	123.7	N9—C18—H18A	123.7
N5—C7—H7A	123.7	N10—C18—H18A	123.7
N1—C1—S1	179.2 (7)	N6—C12—S2	177.9 (7)
N1^i—Ni1—N2—C2	−0.4 (7)	N7^ii—Ni2—N6—C12	87.5 (19)
N1—Ni1—N2—C2	179.6 (7)	N6^ii—Ni2—N7—C13	−19.3 (7)
N4^i—Ni1—N2—C2	89.2 (7)	N6—Ni2—N7—C13	160.7 (7)
N4—Ni1—N2—C2	−90.8 (7)	N9—Ni2—N7—C13	71.0 (7)
N1^i—Ni1—N2—C4	175.8 (7)	N9^ii—Ni2—N7—C13	−109.0 (7)
N1—Ni1—N2—C4	−4.2 (7)	N6^ii—Ni2—N7—C15	169.7 (6)
N4^i—Ni1—N2—C4	−94.6 (7)	N6—Ni2—N7—C15	−10.3 (6)
N4—Ni1—N2—C4	85.4 (7)	N9—Ni2—N7—C15	−100.0 (6)
N1^i—Ni1—N4—C7	25.0 (7)	N9^ii—Ni2—N7—C15	80.0 (6)
N1—Ni1—N4—C7	−155.0 (7)	N6^ii—Ni2—N9—C18	159.1 (6)
N2—Ni1—N4—C7	115.5 (6)	N6—Ni2—N9—C18	−20.9 (6)
N2^i—Ni1—N4—C7	−64.5 (6)	N7—Ni2—N9—C18	69.0 (6)
N1—Ni1—N4—C9	22.0 (7)	N7^ii—Ni2—N9—C18	−111.0 (6)
N2—Ni1—N4—C9	−67.5 (6)	N6^ii—Ni2—N9—C20	−21.0 (6)
N2^i—Ni1—N4—C9	112.5 (6)	N6—Ni2—N9—C20	159.0 (6)
C3—N3—C5—C6	−4.9 (18)	N7—Ni2—N9—C20	−111.1 (6)
C2—N3—C5—C6	173.2 (10)	N7^ii—Ni2—N9—C20	68.9 (6)
C2—N3—C3—C4	−0.1 (11)	C14—N8—C16—C17	−176.6 (11)
C5—N3—C3—C4	178.3 (10)	C13—N8—C16—C17	6 (2)
N3—C3—C4—N2	0.8 (12)	C13—N8—C14—C15	1.6 (10)
C2—N2—C4—C3	−1.3 (11)	C16—N8—C14—C15	−176.5 (9)
Ni1—N2—C4—C3	−178.2 (6)	N8—C14—C15—N7	−1.4 (10)
C4—N2—C2—N3	1.2 (10)	C13—N7—C15—C14	0.6 (9)
Ni1—N2—C2—N3	178.2 (5)	Ni2—N7—C15—C14	173.1 (6)
C3—N3—C2—N2	−0.8 (11)	C15—N7—C13—N8	0.5 (9)
C5—N3—C2—N2	−179.3 (9)	Ni2—N7—C13—N8	−172.3 (5)
C7—N5—C10—C11	173.7 (8)	C14—N8—C13—N7	−1.4 (10)
C8—N5—C10—C11	−4.3 (12)	C16—N8—C13—N7	176.3 (11)
C7—N5—C8—C9	−0.6 (8)	C18—N10—C21—C22	−8.8 (14)
C10—N5—C8—C9	177.6 (7)	C19—N10—C21—C22	174.1 (9)
N5—C8—C9—N4	0.1 (9)	C18—N10—C19—C20	0.6 (8)
C7—N4—C9—C8	0.4 (9)	C21—N10—C19—C20	178.3 (7)
Ni1—N4—C9—C8	−177.1 (5)	N10—C19—C20—N9	−0.7 (9)
C9—N4—C7—N5	−0.9 (9)	C18—N9—C20—C19	0.4 (8)
Ni1—N4—C7—N5	176.7 (5)	Ni2—N9—C20—C19	−179.5 (5)
C8—N5—C7—N4	1.0 (9)	C20—N9—C18—N10	0.0 (8)
C10—N5—C7—N4	−177.4 (6)	Ni2—N9—C18—N10	179.9 (4)
N9—Ni2—N6—C12	−4.8 (19)	C19—N10—C18—N9	−0.4 (8)
N9^ii—Ni2—N6—C12	175.2 (19)	C21—N10—C18—N9	−178.0 (6)
N7—Ni2—N6—C12	−92.5 (19)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···S1^iii	0.93	2.86	3.638 (8)	142
C10—H10A···S1^iii	0.93	2.79	3.601 (8)	146
C16—H16A···S1^iv	0.93	2.85	3.717 (18)	155

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