Tris­(propane-1,3-di­amine)­nickel(II) bis­(tetra­fluoro­borate)

The cationic components, [Ni(C₉H₃₀N₆)]²⁺, of the title compound [Ni(C₉H₃₀N₆)](BF₄)₂ or Ni(pn)₃(BF₄)₂ (pn is 1,3-di­amino­propane), are stacked in the crystal via hydrogen bonding (N—H...F). The geometry around the Ni^II atom is distorted octahedral, with an average Ni—N bond distance of 2.14 (2) Å.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.011 Å
• Disorder in solvent or counterion
• R factor = 0.059
• wR factor = 0.139
• Data-to-parameter ratio = 11.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_302  Alert C Anion/Solvent Disorder .......................      44.00 Perc.

PLAT_420  Alert C D-H Without Acceptor       N(1)   -   H(1A)             ?

PLAT_420  Alert C D-H Without Acceptor       N(6)   -   H(6A)             ?

PLAT_420  Alert C D-H Without Acceptor       N(10)  -   H(10A)            ?

PLAT_420  Alert C D-H Without Acceptor       N(11)  -   H(11B)            ?

PLAT_420  Alert C D-H Without Acceptor       N(15)  -   H(15A)            ?

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      1.093
          Tmax scaled      0.810 Tmin scaled      0.715


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 6 Alert Level C = Please check

---

S1. Comment

The title compound, (I), was obtained in attempt to prepare the analogous compounds [Ni(en)₂ClO₄](ClO₄) and [Ni(en)₂ClO₄](PF₆) (en is ethylenediamine) (Landee et al., 1997). These compounds contain chains of nitrito-bridged nickel(II). These chains of S = 1 ions exhibit antiferromagnetic exchange coupling (Meyer et al., 1982). Accordingly, they are ideal candidates for investigating the conjecture by Haldane that integer spin antiferromagnetic chains exhibit an energy gap between the nonmagnetic singlet ground state and the lowest lying excited state (Haldane, 1983).

In the title compound, the average Ni—N bond distance is 2.140 (24) Å, with N—Ni—N chelate bite angles ranging from 86.57 (18) to 88.6 (2)°. Furthermore, the trans angles are different from the typical octahedral angle 174.2 (2)–179.0 (2)°. The structure is different from the corresponding nitrate structure (Vezzosi et al., 1985). The three six-membered rings are similar to each other, with chair conformations, as shown in Fig. 1. The Ni—N—C and N—C—C angles are close in value, with ranges of 120.5 (4)–123.6 (4) and 112.7 (6)–116.2 (6)°, respectively. The analogous nitrate structure shows a pronounced flattening in one of the six-membered rings, as indicated by wider ranges of the above angles of 114 (1)–128 (1) and 113 (1)–127 (2)°, respectively. N—H···F hydrogen bonds stabilize the packing of the formula units in the crystal. The two tetrafluoroborate anions are disordered, as reflected by the large displacement ellipsoids of the F atoms.

S2. Experimental

1,3-Diaminopropane (32.2 mmol) was added slowly to a solution of Ni(BF₄)₂ (10.6 mmol) in water. To this solution, Ni(BF₄)₂ (10.6 mmol) and NaSCN (10.6 mmol) were added. Slow evaporation leads to the formation of purple crystals.

S3. Refinement

The two tetrafluoroborate anions were found disordered and were refined in sets (set 1: F1, F2, F3 and F4; set 2: F1', F2', F3' and F4'; set 3: F11, F12, F13 and F14; set 4: F11', F12', F13' and F14'). They were refined to partial occupancies of 0.571 (18), 0.429 (18), 0.533 (16) and 0.467 (16), respectively. The B—F bond lengths of each tetrafluoroborate anoion were restrained to the same value, and the F···F distances were restarained to be 1.633 times the corresponding B—F bond lengths.

Computing details

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1996); program(s) used to solve structure: XS in SHELXTL; program(s) used to refine structure: XL in SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: XCIF in SHELXTL.

Figures

Fig. 1. Drawing of the cationic part of (I), with 50% displacement ellipsoids.

Tris(propane-1,3-diamine)nickel(II) tetrafluoroborate.

Crystal data

[Ni(C9H30N6)](BF4)2	Dx = 1.516 Mg m^−3
Mr = 454.72	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 36 reflections
a = 15.2751 (14) Å	θ = 2.4–16.0°
b = 15.498 (2) Å	µ = 1.05 mm^−1
c = 16.835 (2) Å	T = 298 K
V = 3985.6 (8) Å^3	Chunk, purple
Z = 8	0.4 × 0.3 × 0.2 mm
F(000) = 1888

Data collection

Siemens P21 upgraded to P4 diffractometer	1657 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.048
Graphite monochromator	θmax = 25.3°, θmin = 2.2°
ω scans	h = 0→18
Absorption correction: ψ scan (XPREP in SHELXTL; Bruker, 1996)	k = 0→18
Tmin = 0.654, Tmax = 0.742	l = 0→20
4877 measured reflections	3 standard reflections every 100 reflections
3503 independent reflections	intensity decay: no decay was observed

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0507P)^2 + 0.8993P] where P = (Fo^2 + 2Fc^2)/3
3503 reflections	(Δ/σ)max < 0.001
311 parameters	Δρmax = 0.31 e Å^−3
142 restraints	Δρmin = −0.22 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	Occ. (<1)
F11	0.2036 (6)	0.4730 (11)	0.2484 (12)	0.169 (9)	0.533 (16)
F12	0.0839 (10)	0.5213 (11)	0.3073 (8)	0.193 (8)	0.533 (16)
F13	0.0978 (10)	0.5372 (9)	0.1828 (8)	0.161 (7)	0.533 (16)
F14	0.0818 (9)	0.4081 (7)	0.2290 (11)	0.149 (6)	0.533 (16)
F11'	0.1335 (11)	0.5735 (6)	0.2424 (11)	0.153 (7)	0.467 (16)
F12'	0.1925 (10)	0.4531 (11)	0.1993 (11)	0.153 (7)	0.467 (16)
F13'	0.1432 (12)	0.4609 (8)	0.3177 (7)	0.140 (7)	0.467 (16)
F14'	0.0526 (9)	0.4591 (16)	0.2164 (13)	0.212 (12)	0.467 (16)
F1	0.0880 (10)	0.7549 (6)	0.3658 (9)	0.136 (7)	0.571 (18)
F2	0.1863 (8)	0.8101 (9)	0.4403 (11)	0.162 (9)	0.571 (18)
F3	0.0613 (7)	0.8672 (11)	0.4430 (10)	0.145 (6)	0.571 (18)
F4	0.1386 (16)	0.8824 (12)	0.3410 (7)	0.214 (10)	0.571 (18)
F1'	0.0771 (10)	0.9009 (7)	0.3815 (17)	0.143 (9)	0.429 (18)
F2'	0.139 (2)	0.8212 (13)	0.4708 (9)	0.187 (12)	0.429 (18)
F3'	0.1779 (14)	0.8135 (15)	0.3497 (16)	0.214 (10)	0.429 (18)
F4'	0.0532 (15)	0.7649 (12)	0.3870 (15)	0.204 (14)	0.429 (18)
B1	0.1149 (5)	0.8266 (6)	0.3959 (5)	0.082 (2)
B2	0.1243 (7)	0.4857 (6)	0.2428 (6)	0.106 (3)
Ni	0.37602 (4)	0.67037 (4)	0.33755 (4)	0.0517 (2)
N1	0.4308 (3)	0.5881 (3)	0.4260 (3)	0.0691 (14)
H1A	0.4356	0.5351	0.4045	0.083*
H1B	0.4856	0.6068	0.4355	0.083*
N5	0.2521 (3)	0.6288 (3)	0.3788 (3)	0.0700 (14)
H5A	0.2139	0.6708	0.3661	0.084*
H5B	0.2375	0.5826	0.3492	0.084*
N6	0.3814 (3)	0.5629 (3)	0.2542 (3)	0.0770 (14)
H6A	0.4289	0.5315	0.2667	0.092*
H6B	0.3344	0.5294	0.2639	0.092*
N10	0.3092 (4)	0.7449 (4)	0.2480 (3)	0.0937 (18)
H10A	0.2515	0.7380	0.2566	0.112*
H10B	0.3214	0.8006	0.2579	0.112*
N11	0.4990 (3)	0.7140 (3)	0.2968 (3)	0.0792 (15)
H11A	0.5265	0.6683	0.2752	0.095*
H11B	0.4889	0.7516	0.2571	0.095*
N15	0.3738 (3)	0.7833 (3)	0.4120 (3)	0.0791 (14)
H15A	0.3523	0.8268	0.3823	0.095*
H15B	0.3344	0.7733	0.4507	0.095*
C2	0.3878 (5)	0.5779 (5)	0.5031 (4)	0.102 (2)
H2A	0.3862	0.6334	0.5298	0.122*
H2B	0.4219	0.5387	0.5357	0.122*
C3	0.2967 (5)	0.5440 (5)	0.4960 (5)	0.115 (3)
H3A	0.2977	0.4922	0.4636	0.138*
H3B	0.2760	0.5278	0.5484	0.138*
C4	0.2344 (4)	0.6056 (5)	0.4610 (4)	0.101 (2)
H4A	0.1760	0.5811	0.4640	0.121*
H4B	0.2346	0.6578	0.4928	0.121*
C7	0.3841 (5)	0.5779 (5)	0.1676 (4)	0.105 (2)
H7A	0.4416	0.5996	0.1535	0.126*
H7B	0.3761	0.5231	0.1406	0.126*
C8	0.3176 (6)	0.6390 (6)	0.1389 (4)	0.118 (3)
H8A	0.2608	0.6176	0.1558	0.141*
H8B	0.3182	0.6371	0.0813	0.141*
C9	0.3234 (5)	0.7315 (6)	0.1632 (5)	0.108 (3)
H9A	0.3808	0.7535	0.1491	0.129*
H9B	0.2802	0.7644	0.1338	0.129*
C12	0.5592 (4)	0.7540 (6)	0.3501 (4)	0.105 (3)
H12A	0.6098	0.7727	0.3199	0.126*
H12B	0.5792	0.7108	0.3877	0.126*
C13	0.5249 (4)	0.8301 (5)	0.3963 (5)	0.095 (2)
H13A	0.5729	0.8535	0.4274	0.114*
H13B	0.5077	0.8742	0.3585	0.114*
C14	0.4514 (5)	0.8150 (5)	0.4497 (4)	0.109 (3)
H14A	0.4694	0.7739	0.4899	0.131*
H14B	0.4375	0.8687	0.4765	0.131*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F11	0.058 (7)	0.176 (13)	0.27 (3)	0.003 (7)	−0.056 (10)	−0.028 (15)
F12	0.171 (13)	0.230 (19)	0.177 (13)	−0.018 (12)	0.038 (11)	−0.055 (14)
F13	0.188 (14)	0.143 (12)	0.150 (12)	0.057 (10)	−0.030 (9)	0.050 (10)
F14	0.143 (13)	0.111 (8)	0.193 (11)	−0.050 (8)	−0.015 (10)	0.000 (8)
F11'	0.176 (13)	0.110 (9)	0.172 (16)	0.001 (9)	−0.048 (11)	0.017 (9)
F12'	0.136 (15)	0.150 (13)	0.172 (15)	0.012 (11)	0.001 (11)	−0.006 (11)
F13'	0.194 (18)	0.120 (10)	0.106 (9)	−0.027 (10)	−0.036 (10)	0.026 (8)
F14'	0.092 (10)	0.30 (3)	0.25 (2)	−0.029 (16)	−0.041 (11)	−0.05 (3)
F1	0.148 (12)	0.105 (9)	0.155 (12)	0.027 (8)	−0.078 (11)	−0.053 (8)
F2	0.082 (7)	0.136 (9)	0.27 (2)	0.049 (6)	−0.046 (9)	−0.078 (12)
F3	0.114 (8)	0.170 (12)	0.153 (12)	0.030 (8)	0.067 (8)	−0.002 (9)
F4	0.30 (2)	0.200 (18)	0.144 (10)	−0.042 (17)	0.068 (12)	0.084 (11)
F1'	0.109 (11)	0.081 (9)	0.24 (3)	0.054 (9)	−0.005 (13)	−0.006 (13)
F2'	0.32 (3)	0.148 (16)	0.090 (9)	−0.04 (2)	−0.060 (17)	0.038 (10)
F3'	0.179 (15)	0.22 (2)	0.25 (2)	0.099 (15)	0.147 (15)	0.080 (17)
F4'	0.19 (2)	0.19 (2)	0.23 (2)	−0.114 (18)	0.039 (16)	0.028 (18)
B1	0.057 (5)	0.082 (6)	0.106 (7)	0.008 (6)	0.013 (6)	0.004 (7)
B2	0.087 (8)	0.127 (10)	0.103 (9)	−0.049 (10)	0.024 (8)	−0.015 (9)
Ni	0.0461 (4)	0.0546 (4)	0.0544 (4)	0.0046 (4)	0.0040 (4)	0.0020 (4)
N1	0.053 (3)	0.082 (3)	0.072 (3)	0.009 (3)	−0.005 (3)	0.009 (3)
N5	0.052 (3)	0.076 (3)	0.082 (3)	0.003 (3)	0.000 (3)	−0.006 (3)
N6	0.074 (3)	0.079 (3)	0.079 (4)	0.005 (3)	0.010 (3)	−0.013 (3)
N10	0.094 (4)	0.104 (4)	0.082 (4)	0.018 (4)	−0.001 (3)	0.023 (3)
N11	0.062 (3)	0.090 (4)	0.086 (4)	−0.006 (3)	0.018 (3)	−0.001 (3)
N15	0.067 (3)	0.075 (3)	0.095 (4)	0.003 (3)	0.006 (3)	−0.017 (3)
C2	0.103 (6)	0.130 (6)	0.073 (5)	0.022 (5)	−0.002 (5)	0.031 (5)
C3	0.098 (6)	0.116 (6)	0.131 (7)	0.011 (5)	0.049 (6)	0.053 (6)
C4	0.075 (5)	0.121 (6)	0.106 (6)	0.000 (5)	0.036 (4)	0.011 (5)
C7	0.115 (6)	0.139 (6)	0.060 (4)	0.004 (6)	0.020 (5)	−0.023 (5)
C8	0.140 (8)	0.145 (8)	0.069 (5)	−0.016 (7)	−0.011 (5)	0.011 (5)
C9	0.114 (6)	0.133 (7)	0.075 (5)	0.010 (6)	0.000 (5)	0.033 (6)
C12	0.052 (4)	0.163 (8)	0.102 (6)	−0.012 (5)	0.009 (4)	−0.005 (6)
C13	0.065 (4)	0.098 (5)	0.121 (6)	−0.021 (4)	−0.018 (5)	0.000 (6)
C14	0.098 (6)	0.136 (7)	0.093 (5)	−0.014 (5)	−0.010 (5)	−0.042 (5)

Geometric parameters (Å, º)

F11—B2	1.231 (12)	N10—H10A	0.9000
F12—B2	1.366 (12)	N10—H10B	0.9000
F13—B2	1.351 (12)	N11—C12	1.427 (8)
F14—B2	1.386 (12)	N11—H11A	0.9000
F11'—B2	1.369 (12)	N11—H11B	0.9000
F12'—B2	1.370 (14)	N15—C14	1.432 (8)
F13'—B2	1.349 (12)	N15—H15A	0.9000
F14'—B2	1.252 (13)	N15—H15B	0.9000
F1—B1	1.290 (11)	C2—C3	1.492 (9)
F2—B1	1.347 (11)	C2—H2A	0.9700
F3—B1	1.301 (11)	C2—H2B	0.9700
F4—B1	1.316 (11)	C3—C4	1.472 (9)
F1'—B1	1.310 (12)	C3—H3A	0.9700
F2'—B1	1.315 (12)	C3—H3B	0.9700
F3'—B1	1.255 (12)	C4—H4A	0.9700
F4'—B1	1.352 (14)	C4—H4B	0.9700
Ni—N11	2.111 (5)	C7—C8	1.471 (10)
Ni—N5	2.116 (5)	C7—H7A	0.9700
Ni—N1	2.132 (4)	C7—H7B	0.9700
Ni—N15	2.153 (4)	C8—C9	1.494 (10)
Ni—N10	2.156 (5)	C8—H8A	0.9700
Ni—N6	2.179 (4)	C8—H8B	0.9700
N1—C2	1.464 (7)	C9—H9A	0.9700
N1—H1A	0.9000	C9—H9B	0.9700
N1—H1B	0.9000	C12—C13	1.507 (9)
N5—C4	1.455 (7)	C12—H12A	0.9700
N5—H5A	0.9000	C12—H12B	0.9700
N5—H5B	0.9000	C13—C14	1.458 (9)
N6—C7	1.477 (7)	C13—H13A	0.9700
N6—H6A	0.9000	C13—H13B	0.9700
N6—H6B	0.9000	C14—H14A	0.9700
N10—C9	1.459 (8)	C14—H14B	0.9700
F3'—B1—F1	82.0 (15)	Ni—N5—H5B	106.4
F3'—B1—F3	159.8 (14)	H5A—N5—H5B	106.5
F1—B1—F3	117.2 (10)	C7—N6—Ni	121.1 (4)
F3'—B1—F1'	111.4 (12)	C7—N6—H6A	107.0
F1—B1—F1'	123.0 (11)	Ni—N6—H6A	107.0
F3—B1—F1'	53.9 (9)	C7—N6—H6B	107.0
F3'—B1—F2'	111.9 (13)	Ni—N6—H6B	107.0
F1—B1—F2'	114.2 (12)	H6A—N6—H6B	106.8
F3—B1—F2'	67.7 (12)	C9—N10—Ni	122.6 (5)
F1'—B1—F2'	110.8 (12)	C9—N10—H10A	106.7
F3'—B1—F4	57.3 (9)	Ni—N10—H10A	106.7
F1—B1—F4	112.2 (10)	C9—N10—H10B	106.7
F3—B1—F4	106.5 (10)	Ni—N10—H10B	106.7
F1'—B1—F4	54.2 (9)	H10A—N10—H10B	106.6
F2'—B1—F4	129.8 (13)	C12—N11—Ni	120.5 (4)
F3'—B1—F2	72.0 (11)	C12—N11—H11A	107.2
F1—B1—F2	108.1 (10)	Ni—N11—H11A	107.2
F3—B1—F2	105.3 (9)	C12—N11—H11B	107.2
F1'—B1—F2	128.8 (11)	Ni—N11—H11B	107.2
F2'—B1—F2	39.9 (12)	H11A—N11—H11B	106.8
F4—B1—F2	107.0 (10)	C14—N15—Ni	121.6 (4)
F3'—B1—F4'	110.5 (13)	C14—N15—H15A	106.9
F1—B1—F4'	28.7 (13)	Ni—N15—H15A	106.9
F3—B1—F4'	88.4 (13)	C14—N15—H15B	106.9
F1'—B1—F4'	107.1 (12)	Ni—N15—H15B	106.9
F2'—B1—F4'	104.7 (12)	H15A—N15—H15B	106.7
F4—B1—F4'	125.3 (14)	N1—C2—C3	112.7 (6)
F2—B1—F4'	119.4 (14)	N1—C2—H2A	109.1
F11—B2—F14'	146.7 (14)	C3—C2—H2A	109.1
F11—B2—F13'	70.9 (11)	N1—C2—H2B	109.1
F14'—B2—F13'	115.2 (14)	C3—C2—H2B	109.1
F11—B2—F13	116.5 (13)	H2A—C2—H2B	107.8
F14'—B2—F13	70.5 (12)	C4—C3—C2	114.0 (6)
F13'—B2—F13	158.8 (11)	C4—C3—H3A	108.8
F11—B2—F12	116.7 (12)	C2—C3—H3A	108.8
F14'—B2—F12	91.2 (13)	C4—C3—H3B	108.8
F13'—B2—F12	57.9 (8)	C2—C3—H3B	108.8
F13—B2—F12	102.7 (11)	H3A—C3—H3B	107.7
F11—B2—F11'	93.4 (12)	N5—C4—C3	114.9 (6)
F14'—B2—F11'	114.5 (13)	N5—C4—H4A	108.5
F13'—B2—F11'	105.4 (10)	C3—C4—H4A	108.5
F13—B2—F11'	55.9 (8)	N5—C4—H4B	108.5
F12—B2—F11'	69.4 (9)	C3—C4—H4B	108.5
F11—B2—F12'	39.9 (8)	H4A—C4—H4B	107.5
F14'—B2—F12'	110.8 (12)	C8—C7—N6	113.9 (6)
F13'—B2—F12'	103.4 (11)	C8—C7—H7A	108.8
F13—B2—F12'	92.6 (11)	N6—C7—H7A	108.8
F12—B2—F12'	156.6 (12)	C8—C7—H7B	108.8
F11'—B2—F12'	106.6 (11)	N6—C7—H7B	108.8
F11—B2—F14	109.6 (11)	H7A—C7—H7B	107.7
F14'—B2—F14	41.0 (10)	C7—C8—C9	119.1 (7)
F13'—B2—F14	90.6 (11)	C7—C8—H8A	107.5
F13—B2—F14	104.3 (11)	C9—C8—H8A	107.5
F12—B2—F14	105.8 (11)	C7—C8—H8B	107.5
F11'—B2—F14	155.5 (12)	C9—C8—H8B	107.5
F12'—B2—F14	87.0 (12)	H8A—C8—H8B	107.0
N11—Ni—N5	179.0 (2)	N10—C9—C8	113.2 (7)
N11—Ni—N1	93.95 (19)	N10—C9—H9A	108.9
N5—Ni—N1	86.57 (18)	C8—C9—H9A	108.9
N11—Ni—N15	86.74 (19)	N10—C9—H9B	108.9
N5—Ni—N15	92.43 (19)	C8—C9—H9B	108.9
N1—Ni—N15	94.94 (19)	H9A—C9—H9B	107.7
N11—Ni—N10	91.3 (2)	N11—C12—C13	116.2 (6)
N5—Ni—N10	88.2 (2)	N11—C12—H12A	108.2
N1—Ni—N10	174.2 (2)	C13—C12—H12A	108.2
N15—Ni—N10	87.9 (2)	N11—C12—H12B	108.2
N11—Ni—N6	90.11 (19)	C13—C12—H12B	108.2
N5—Ni—N6	90.70 (19)	H12A—C12—H12B	107.4
N1—Ni—N6	88.75 (18)	C14—C13—C12	117.4 (6)
N15—Ni—N6	175.30 (19)	C14—C13—H13A	108.0
N10—Ni—N6	88.6 (2)	C12—C13—H13A	108.0
C2—N1—Ni	120.5 (4)	C14—C13—H13B	108.0
C2—N1—H1A	107.2	C12—C13—H13B	108.0
Ni—N1—H1A	107.2	H13A—C13—H13B	107.2
C2—N1—H1B	107.2	N15—C14—C13	114.8 (6)
Ni—N1—H1B	107.2	N15—C14—H14A	108.6
H1A—N1—H1B	106.8	C13—C14—H14A	108.6
C4—N5—Ni	123.6 (4)	N15—C14—H14B	108.6
C4—N5—H5A	106.4	C13—C14—H14B	108.6
Ni—N5—H5A	106.4	H14A—C14—H14B	107.5
C4—N5—H5B	106.4
N11—Ni—N1—C2	143.1 (5)	N10—Ni—N11—C12	125.6 (6)
N5—Ni—N1—C2	−36.1 (5)	N6—Ni—N11—C12	−145.8 (5)
N15—Ni—N1—C2	56.1 (5)	N11—Ni—N15—C14	−37.7 (5)
N6—Ni—N1—C2	−126.9 (5)	N5—Ni—N15—C14	142.8 (5)
N1—Ni—N5—C4	31.9 (5)	N1—Ni—N15—C14	56.0 (5)
N15—Ni—N5—C4	−62.9 (5)	N10—Ni—N15—C14	−129.1 (5)
N10—Ni—N5—C4	−150.8 (6)	Ni—N1—C2—C3	59.2 (8)
N6—Ni—N5—C4	120.6 (5)	N1—C2—C3—C4	−69.8 (9)
N11—Ni—N6—C7	−62.3 (5)	Ni—N5—C4—C3	−50.3 (9)
N5—Ni—N6—C7	117.1 (5)	C2—C3—C4—N5	64.6 (9)
N1—Ni—N6—C7	−156.3 (5)	Ni—N6—C7—C8	−48.7 (8)
N10—Ni—N6—C7	28.9 (5)	N6—C7—C8—C9	66.8 (10)
N11—Ni—N10—C9	60.3 (6)	Ni—N10—C9—C8	49.1 (9)
N5—Ni—N10—C9	−120.5 (6)	C7—C8—C9—N10	−66.6 (10)
N15—Ni—N10—C9	147.0 (6)	Ni—N11—C12—C13	−54.4 (8)
N6—Ni—N10—C9	−29.7 (6)	N11—C12—C13—C14	61.4 (9)
N1—Ni—N11—C12	−57.0 (6)	Ni—N15—C14—C13	53.5 (9)
N15—Ni—N11—C12	37.7 (5)	C12—C13—C14—N15	−60.0 (9)