Abstract
In the title compound, [Ni(C15H12N4)2](ClO4)2, the NiII atom lies on an inversion center and is octahedrally coordinated by the N atoms of two tridentate tri-2-pyridylamine ligands. The two perchlorate anions are disordered over two sites with a refined occupancy ratio of 0.528 (19):0.472 (19).
Related literature
For background to luminescent coordination compounds, see: Liu et al. (1997 ▶). For related complexes, including the synthesis of 2,2′,2′′-tpa (tpa is tri-2-pyridylamine), see: Yang et al. (1999 ▶). For information on the use of 2,2′,2′′-tpa as a bidentate ligand, see: Wang et al. (2009 ▶). 
Experimental
Crystal data
[Ni(C15H12N4)2](ClO4)2
M r = 754.18
Monoclinic,
a = 8.360 (4) Å
b = 17.570 (8) Å
c = 11.165 (5) Å
β = 99.542 (5)°
V = 1617.3 (13) Å3
Z = 2
Mo Kα radiation
μ = 0.83 mm−1
T = 296 K
0.22 × 0.15 × 0.10 mm
Data collection
Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.861, T max = 0.920
14055 measured reflections
3895 independent reflections
2611 reflections with I > 2σ(I)
R int = 0.040
Refinement
R[F 2 > 2σ(F 2)] = 0.039
wR(F 2) = 0.096
S = 1.03
3895 reflections
269 parameters
H-atom parameters constrained
Δρmax = 0.25 e Å−3
Δρmin = −0.26 e Å−3
Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supplementary Material
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051627/nk2079sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051627/nk2079Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
This work was supported by NY208044, BK2010527 and in part by the National Basic Research Program of China (2009CB930601).
supplementary crystallographic information
Comment
Luminescent organic and coordination compounds have been an active research area for decades because of their various potential applications in materials sciences. It has been demonstrated that 2,2'-dipyridylamine can produce a bright blue luminescence when deprotonated and bound to either an aluminium ion or a boron center (Liu et al., 1997). However, many of the previously reported aluminium or boron compounds based on 2,2'-dipyridylamine are not stable enough for electroluminescent devices. The neutral tripodal ligand 2,2',2''-tripyridylamine and its derivatives with Zn(II), Cd(II) and Hg(II) have been investigated for their optical properties (Yang et al., 1999). However, its complexes with d8 metal(II) remain unkown. By using the 2,2',2''-tripyridylamine ligand, we report here the synthesis and crystal structure of the title compound, bis(2,2',2''-tripyridylamine)nickel(II) bis(perchlorate), (I).
The structure of (I) consists of monomeric [Ni(2,2',2''-tpa)2]2+ cations and associated ClO4- anions. The Ni atom lies on an inversion center. As shown in Fig. 1, the Ni center is six-coordinate with an octahedral geometry. In principle, 2,2',2''-tpa can function not only as a tridentate chelating ligand but also as a bidentate chelating ligand where only two pyridyl groups bind to the same central atom (Wang et al., 2009). In the title compound, each 2,2',2''-tpa ligand functions as a tridentate ligand, chelating to the nickel center. The two perchlorate anions are disordered over two sites with a refined occupancy ratio of 0.528 (19) : 0.472 (19).
Experimental
The ligand, 2,2',2''-tpa was synthesized according to the procedure described in the literature (Yang et al. (1999)).
A solution of 2,2',2''-tpa (62.11 mg, 0.2 mmol) in acetonitrile (5 ml) was added dropwise to a solution of Ni(ClO4)2.6H2O (36.58 mg, 0.1 mmol) in acetonitrile (2 ml). The mixture was stirred at room temperature for 5 min and then filtered. Light purple crystals of (I) suitable for X-ray analysis were obtained by slow diffusion of filtrate.
Refinement
The two perchlorate anions are disordered over two sites with a refined occupancy ratio of 0.528 (19) : 0.472 (19). Aromatic H atoms were placed in calculated positions with C—H = 0.93 Å, and refined in riding mode with Uiso(H) = 1.2Ueq(C).
Figures
Fig. 1.
The structure of (I), shown with 30% probability displacement ellipsoids. The disordered perchlorate anions and H atoms have been omitted for clarity. Unlabeled atoms are related to labeled atoms by inversion symmetry.
Crystal data
| [Ni(C15H12N4)2](ClO4)2 | F(000) = 772 |
| Mr = 754.18 | Dx = 1.549 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 7662 reflections |
| a = 8.360 (4) Å | θ = 2.2–27.9° |
| b = 17.570 (8) Å | µ = 0.83 mm−1 |
| c = 11.165 (5) Å | T = 296 K |
| β = 99.542 (5)° | Block, purple |
| V = 1617.3 (13) Å3 | 0.22 × 0.15 × 0.10 mm |
| Z = 2 |
Data collection
| Bruker SMART CCD area-detector diffractometer | 3895 independent reflections |
| Radiation source: fine-focus sealed tube | 2611 reflections with I > 2σ(I) |
| graphite | Rint = 0.040 |
| Detector resolution: 8.366 pixels mm-1 | θmax = 28.4°, θmin = 2.3° |
| phi and ω scans | h = −11→11 |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −23→23 |
| Tmin = 0.861, Tmax = 0.920 | l = −14→14 |
| 14055 measured reflections |
Refinement
| 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.096 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0415P)2 + 0.1545P] where P = (Fo2 + 2Fc2)/3 |
| 3895 reflections | (Δ/σ)max = 0.001 |
| 269 parameters | Δρmax = 0.25 e Å−3 |
| 0 restraints | Δρmin = −0.26 e Å−3 |
Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Ni1 | 0.0000 | 0.0000 | 0.0000 | 0.03843 (14) | |
| N1 | 0.1260 (2) | −0.05805 (10) | −0.21770 (15) | 0.0415 (4) | |
| N2 | 0.1529 (2) | −0.09211 (10) | −0.00942 (15) | 0.0425 (4) | |
| N3 | −0.1341 (2) | −0.04164 (10) | −0.16286 (16) | 0.0425 (5) | |
| N4 | 0.1399 (2) | 0.05822 (10) | −0.10841 (16) | 0.0428 (4) | |
| C1 | 0.1923 (3) | −0.10685 (12) | −0.11845 (19) | 0.0398 (5) | |
| C2 | 0.2910 (3) | −0.16666 (13) | −0.1379 (2) | 0.0491 (6) | |
| H2 | 0.3180 | −0.1751 | −0.2143 | 0.059* | |
| C3 | 0.3487 (3) | −0.21360 (14) | −0.0420 (2) | 0.0588 (7) | |
| H3 | 0.4148 | −0.2548 | −0.0528 | 0.071* | |
| C4 | 0.3080 (3) | −0.19915 (13) | 0.0696 (2) | 0.0546 (6) | |
| H4 | 0.3456 | −0.2305 | 0.1354 | 0.066* | |
| C5 | 0.2114 (3) | −0.13810 (13) | 0.0829 (2) | 0.0496 (6) | |
| H5 | 0.1852 | −0.1281 | 0.1591 | 0.060* | |
| C6 | −0.0476 (3) | −0.06409 (12) | −0.24704 (19) | 0.0414 (5) | |
| C7 | −0.1176 (3) | −0.09311 (14) | −0.3578 (2) | 0.0547 (6) | |
| H7 | −0.0542 | −0.1076 | −0.4150 | 0.066* | |
| C8 | −0.2834 (4) | −0.10013 (15) | −0.3818 (2) | 0.0647 (7) | |
| H8 | −0.3339 | −0.1197 | −0.4559 | 0.078* | |
| C9 | −0.3738 (3) | −0.07818 (14) | −0.2965 (2) | 0.0577 (7) | |
| H9 | −0.4861 | −0.0832 | −0.3110 | 0.069* | |
| C10 | −0.2954 (3) | −0.04864 (14) | −0.1890 (2) | 0.0533 (6) | |
| H10 | −0.3572 | −0.0327 | −0.1317 | 0.064* | |
| C11 | 0.1900 (3) | 0.13045 (13) | −0.0929 (2) | 0.0492 (6) | |
| H11 | 0.1612 | 0.1583 | −0.0290 | 0.059* | |
| C12 | 0.2822 (3) | 0.16462 (14) | −0.1682 (2) | 0.0575 (7) | |
| H12 | 0.3156 | 0.2149 | −0.1552 | 0.069* | |
| C13 | 0.3246 (3) | 0.12403 (16) | −0.2624 (2) | 0.0627 (7) | |
| H13 | 0.3886 | 0.1461 | −0.3136 | 0.075* | |
| C14 | 0.2716 (3) | 0.05020 (14) | −0.2809 (2) | 0.0527 (6) | |
| H14 | 0.2970 | 0.0219 | −0.3456 | 0.063* | |
| C15 | 0.1808 (3) | 0.01931 (12) | −0.20188 (19) | 0.0402 (5) | |
| Cl1 | 0.2377 (6) | 0.3455 (4) | 0.0694 (3) | 0.0463 (11) | 0.472 (19) |
| O1 | 0.1538 (19) | 0.3916 (9) | 0.1111 (12) | 0.128 (5) | 0.472 (19) |
| O2 | 0.224 (3) | 0.2727 (6) | 0.1240 (8) | 0.153 (7) | 0.472 (19) |
| O3 | 0.3932 (15) | 0.3751 (8) | 0.1296 (13) | 0.129 (4) | 0.472 (19) |
| O4 | 0.214 (2) | 0.3370 (9) | −0.0534 (9) | 0.140 (6) | 0.472 (19) |
| Cl1' | 0.2323 (10) | 0.3362 (6) | 0.0668 (6) | 0.095 (2) | 0.528 (19) |
| O1' | 0.1418 (16) | 0.4114 (7) | 0.0767 (15) | 0.133 (5) | 0.528 (19) |
| O2' | 0.1138 (18) | 0.2869 (8) | 0.0907 (17) | 0.169 (5) | 0.528 (19) |
| O3' | 0.3760 (15) | 0.3273 (15) | 0.1348 (13) | 0.205 (9) | 0.528 (19) |
| O4' | 0.2693 (18) | 0.3279 (7) | −0.0504 (11) | 0.109 (4) | 0.528 (19) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.0488 (3) | 0.0391 (2) | 0.0291 (2) | 0.00336 (19) | 0.01177 (17) | −0.00443 (17) |
| N1 | 0.0529 (12) | 0.0401 (10) | 0.0331 (10) | 0.0029 (9) | 0.0114 (9) | −0.0027 (8) |
| N2 | 0.0543 (12) | 0.0416 (10) | 0.0319 (10) | 0.0059 (9) | 0.0082 (8) | −0.0038 (8) |
| N3 | 0.0476 (12) | 0.0456 (11) | 0.0343 (10) | 0.0033 (9) | 0.0069 (9) | −0.0043 (8) |
| N4 | 0.0525 (12) | 0.0421 (10) | 0.0355 (10) | −0.0008 (9) | 0.0125 (9) | −0.0026 (8) |
| C1 | 0.0457 (13) | 0.0387 (12) | 0.0355 (11) | 0.0002 (10) | 0.0079 (10) | −0.0066 (9) |
| C2 | 0.0524 (15) | 0.0475 (13) | 0.0496 (14) | 0.0036 (11) | 0.0149 (12) | −0.0110 (11) |
| C3 | 0.0608 (17) | 0.0466 (14) | 0.0683 (17) | 0.0154 (12) | 0.0091 (14) | −0.0037 (13) |
| C4 | 0.0587 (16) | 0.0474 (14) | 0.0553 (15) | 0.0077 (12) | 0.0022 (13) | 0.0065 (12) |
| C5 | 0.0603 (16) | 0.0517 (14) | 0.0369 (13) | 0.0048 (12) | 0.0080 (11) | 0.0005 (11) |
| C6 | 0.0542 (15) | 0.0386 (12) | 0.0321 (11) | 0.0019 (10) | 0.0092 (10) | −0.0034 (9) |
| C7 | 0.0695 (18) | 0.0591 (15) | 0.0352 (13) | 0.0035 (13) | 0.0073 (12) | −0.0110 (11) |
| C8 | 0.075 (2) | 0.0696 (18) | 0.0440 (15) | −0.0041 (15) | −0.0063 (14) | −0.0125 (13) |
| C9 | 0.0534 (16) | 0.0610 (16) | 0.0549 (16) | −0.0016 (13) | −0.0021 (13) | −0.0030 (13) |
| C10 | 0.0530 (16) | 0.0580 (15) | 0.0489 (14) | 0.0027 (12) | 0.0082 (12) | −0.0058 (12) |
| C11 | 0.0578 (16) | 0.0439 (13) | 0.0462 (14) | −0.0016 (11) | 0.0095 (12) | −0.0046 (11) |
| C12 | 0.0610 (17) | 0.0502 (14) | 0.0608 (17) | −0.0084 (13) | 0.0091 (13) | 0.0075 (13) |
| C13 | 0.0621 (17) | 0.0682 (18) | 0.0627 (17) | −0.0046 (14) | 0.0242 (14) | 0.0156 (14) |
| C14 | 0.0595 (16) | 0.0600 (16) | 0.0426 (14) | 0.0065 (13) | 0.0199 (12) | 0.0062 (11) |
| C15 | 0.0434 (13) | 0.0465 (13) | 0.0317 (11) | 0.0049 (10) | 0.0095 (10) | 0.0010 (9) |
| Cl1 | 0.046 (2) | 0.072 (2) | 0.0231 (16) | 0.0105 (14) | 0.0106 (12) | −0.0077 (12) |
| O1 | 0.158 (8) | 0.140 (10) | 0.099 (5) | 0.080 (7) | 0.058 (6) | 0.001 (6) |
| O2 | 0.31 (2) | 0.084 (6) | 0.070 (5) | −0.006 (9) | 0.037 (8) | 0.018 (4) |
| O3 | 0.095 (6) | 0.186 (10) | 0.100 (6) | −0.052 (7) | 0.000 (4) | −0.031 (6) |
| O4 | 0.195 (12) | 0.199 (9) | 0.023 (4) | 0.091 (8) | 0.013 (5) | −0.005 (4) |
| Cl1' | 0.109 (4) | 0.101 (3) | 0.075 (3) | 0.037 (3) | 0.014 (3) | −0.020 (2) |
| O1' | 0.107 (5) | 0.070 (5) | 0.211 (13) | 0.027 (4) | −0.004 (6) | −0.036 (6) |
| O2' | 0.169 (9) | 0.122 (7) | 0.251 (13) | 0.007 (7) | 0.139 (9) | 0.013 (7) |
| O3' | 0.086 (8) | 0.36 (3) | 0.148 (8) | 0.120 (11) | −0.033 (7) | −0.089 (13) |
| O4' | 0.144 (8) | 0.120 (6) | 0.080 (6) | −0.018 (6) | 0.068 (6) | −0.032 (4) |
Geometric parameters (Å, °)
| Ni1—N2 | 2.0755 (19) | C7—C8 | 1.373 (4) |
| Ni1—N2i | 2.0755 (19) | C7—H7 | 0.9300 |
| Ni1—N4 | 2.0851 (18) | C8—C9 | 1.367 (4) |
| Ni1—N4i | 2.0851 (18) | C8—H8 | 0.9300 |
| Ni1—N3i | 2.1029 (19) | C9—C10 | 1.370 (3) |
| Ni1—N3 | 2.1029 (19) | C9—H9 | 0.9300 |
| N1—C15 | 1.436 (3) | C10—H10 | 0.9300 |
| N1—C1 | 1.437 (3) | C11—C12 | 1.370 (3) |
| N1—C6 | 1.438 (3) | C11—H11 | 0.9300 |
| N2—C5 | 1.337 (3) | C12—C13 | 1.366 (4) |
| N2—C1 | 1.338 (3) | C12—H12 | 0.9300 |
| N3—C6 | 1.337 (3) | C13—C14 | 1.375 (3) |
| N3—C10 | 1.337 (3) | C13—H13 | 0.9300 |
| N4—C15 | 1.339 (3) | C14—C15 | 1.368 (3) |
| N4—C11 | 1.339 (3) | C14—H14 | 0.9300 |
| C1—C2 | 1.375 (3) | Cl1—O1 | 1.212 (13) |
| C2—C3 | 1.374 (3) | Cl1—O4 | 1.361 (11) |
| C2—H2 | 0.9300 | Cl1—O2 | 1.430 (13) |
| C3—C4 | 1.369 (3) | Cl1—O3 | 1.457 (12) |
| C3—H3 | 0.9300 | Cl1'—O3' | 1.320 (11) |
| C4—C5 | 1.366 (3) | Cl1'—O2' | 1.375 (14) |
| C4—H4 | 0.9300 | Cl1'—O4' | 1.401 (11) |
| C5—H5 | 0.9300 | Cl1'—O1' | 1.537 (15) |
| C6—C7 | 1.375 (3) | ||
| N2—Ni1—N2i | 180.0 | N3—C6—C7 | 122.9 (2) |
| N2—Ni1—N4 | 86.78 (7) | N3—C6—N1 | 117.46 (18) |
| N2i—Ni1—N4 | 93.22 (7) | C7—C6—N1 | 119.7 (2) |
| N2—Ni1—N4i | 93.22 (7) | C8—C7—C6 | 118.3 (2) |
| N2i—Ni1—N4i | 86.78 (7) | C8—C7—H7 | 120.9 |
| N4—Ni1—N4i | 180.0 | C6—C7—H7 | 120.9 |
| N2—Ni1—N3i | 94.05 (7) | C9—C8—C7 | 119.7 (2) |
| N2i—Ni1—N3i | 85.95 (7) | C9—C8—H8 | 120.1 |
| N4—Ni1—N3i | 93.52 (8) | C7—C8—H8 | 120.1 |
| N4i—Ni1—N3i | 86.48 (8) | C8—C9—C10 | 118.5 (3) |
| N2—Ni1—N3 | 85.95 (7) | C8—C9—H9 | 120.7 |
| N2i—Ni1—N3 | 94.05 (7) | C10—C9—H9 | 120.7 |
| N4—Ni1—N3 | 86.48 (8) | N3—C10—C9 | 123.0 (2) |
| N4i—Ni1—N3 | 93.52 (8) | N3—C10—H10 | 118.5 |
| N3i—Ni1—N3 | 180.0 | C9—C10—H10 | 118.5 |
| C15—N1—C1 | 113.30 (17) | N4—C11—C12 | 122.2 (2) |
| C15—N1—C6 | 112.77 (17) | N4—C11—H11 | 118.9 |
| C1—N1—C6 | 112.15 (17) | C12—C11—H11 | 118.9 |
| C5—N2—C1 | 118.06 (19) | C13—C12—C11 | 119.2 (2) |
| C5—N2—Ni1 | 125.59 (15) | C13—C12—H12 | 120.4 |
| C1—N2—Ni1 | 116.34 (14) | C11—C12—H12 | 120.4 |
| C6—N3—C10 | 117.54 (19) | C12—C13—C14 | 119.3 (2) |
| C6—N3—Ni1 | 115.96 (15) | C12—C13—H13 | 120.3 |
| C10—N3—Ni1 | 126.49 (15) | C14—C13—H13 | 120.3 |
| C15—N4—C11 | 118.01 (19) | C15—C14—C13 | 118.5 (2) |
| C15—N4—Ni1 | 116.26 (15) | C15—C14—H14 | 120.8 |
| C11—N4—Ni1 | 125.72 (15) | C13—C14—H14 | 120.8 |
| N2—C1—C2 | 122.4 (2) | N4—C15—C14 | 122.8 (2) |
| N2—C1—N1 | 117.66 (18) | N4—C15—N1 | 117.50 (18) |
| C2—C1—N1 | 119.90 (19) | C14—C15—N1 | 119.74 (19) |
| C3—C2—C1 | 118.5 (2) | O1—Cl1—O4 | 117.6 (10) |
| C3—C2—H2 | 120.7 | O1—Cl1—O2 | 109.8 (9) |
| C1—C2—H2 | 120.7 | O4—Cl1—O2 | 108.8 (9) |
| C4—C3—C2 | 119.3 (2) | O1—Cl1—O3 | 96.5 (10) |
| C4—C3—H3 | 120.3 | O4—Cl1—O3 | 118.3 (10) |
| C2—C3—H3 | 120.3 | O2—Cl1—O3 | 104.7 (9) |
| C5—C4—C3 | 119.0 (2) | O3'—Cl1'—O2' | 115.5 (11) |
| C5—C4—H4 | 120.5 | O3'—Cl1'—O4' | 101.8 (10) |
| C3—C4—H4 | 120.5 | O2'—Cl1'—O4' | 113.2 (9) |
| N2—C5—C4 | 122.6 (2) | O3'—Cl1'—O1' | 118.1 (12) |
| N2—C5—H5 | 118.7 | O2'—Cl1'—O1' | 98.6 (8) |
| C4—C5—H5 | 118.7 | O4'—Cl1'—O1' | 110.1 (9) |
| N4—Ni1—N2—C5 | 138.49 (19) | C2—C3—C4—C5 | −0.3 (4) |
| N4i—Ni1—N2—C5 | −41.51 (19) | C1—N2—C5—C4 | −0.4 (3) |
| N3i—Ni1—N2—C5 | 45.18 (19) | Ni1—N2—C5—C4 | 178.09 (17) |
| N3—Ni1—N2—C5 | −134.82 (19) | C3—C4—C5—N2 | 0.9 (4) |
| N4—Ni1—N2—C1 | −42.98 (16) | C10—N3—C6—C7 | 0.4 (3) |
| N4i—Ni1—N2—C1 | 137.02 (16) | Ni1—N3—C6—C7 | 179.54 (18) |
| N3i—Ni1—N2—C1 | −136.29 (16) | C10—N3—C6—N1 | −178.68 (19) |
| N3—Ni1—N2—C1 | 43.71 (16) | Ni1—N3—C6—N1 | 0.4 (2) |
| N2—Ni1—N3—C6 | −44.10 (16) | C15—N1—C6—N3 | −65.0 (2) |
| N2i—Ni1—N3—C6 | 135.90 (16) | C1—N1—C6—N3 | 64.4 (2) |
| N4—Ni1—N3—C6 | 42.92 (16) | C15—N1—C6—C7 | 115.9 (2) |
| N4i—Ni1—N3—C6 | −137.08 (16) | C1—N1—C6—C7 | −114.8 (2) |
| N2—Ni1—N3—C10 | 134.9 (2) | N3—C6—C7—C8 | −0.9 (4) |
| N2i—Ni1—N3—C10 | −45.1 (2) | N1—C6—C7—C8 | 178.2 (2) |
| N4—Ni1—N3—C10 | −138.1 (2) | C6—C7—C8—C9 | 0.2 (4) |
| N4i—Ni1—N3—C10 | 41.9 (2) | C7—C8—C9—C10 | 0.8 (4) |
| N2—Ni1—N4—C15 | 43.27 (16) | C6—N3—C10—C9 | 0.7 (3) |
| N2i—Ni1—N4—C15 | −136.73 (16) | Ni1—N3—C10—C9 | −178.30 (18) |
| N3i—Ni1—N4—C15 | 137.13 (16) | C8—C9—C10—N3 | −1.3 (4) |
| N3—Ni1—N4—C15 | −42.87 (16) | C15—N4—C11—C12 | −0.8 (3) |
| N2—Ni1—N4—C11 | −137.4 (2) | Ni1—N4—C11—C12 | 179.82 (18) |
| N2i—Ni1—N4—C11 | 42.6 (2) | N4—C11—C12—C13 | 0.1 (4) |
| N3i—Ni1—N4—C11 | −43.5 (2) | C11—C12—C13—C14 | 1.0 (4) |
| N3—Ni1—N4—C11 | 136.5 (2) | C12—C13—C14—C15 | −1.5 (4) |
| C5—N2—C1—C2 | −0.6 (3) | C11—N4—C15—C14 | 0.3 (3) |
| Ni1—N2—C1—C2 | −179.22 (17) | Ni1—N4—C15—C14 | 179.77 (18) |
| C5—N2—C1—N1 | 178.7 (2) | C11—N4—C15—N1 | −179.87 (19) |
| Ni1—N2—C1—N1 | 0.1 (3) | Ni1—N4—C15—N1 | −0.4 (3) |
| C15—N1—C1—N2 | 64.0 (3) | C13—C14—C15—N4 | 0.8 (4) |
| C6—N1—C1—N2 | −65.1 (2) | C13—C14—C15—N1 | −179.0 (2) |
| C15—N1—C1—C2 | −116.7 (2) | C1—N1—C15—N4 | −63.5 (3) |
| C6—N1—C1—C2 | 114.2 (2) | C6—N1—C15—N4 | 65.3 (2) |
| N2—C1—C2—C3 | 1.1 (3) | C1—N1—C15—C14 | 116.3 (2) |
| N1—C1—C2—C3 | −178.2 (2) | C6—N1—C15—C14 | −115.0 (2) |
| C1—C2—C3—C4 | −0.6 (4) |
Symmetry codes: (i) −x, −y, −z.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2079).
References
- Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
- Liu, W., Hassan, A. & Wang, S. (1997). Organometallics, 16, 4257–4259.
- Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
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- Yang, W., Schmider, H., Wu, Q., Zhang, Y. & Wang, S. (1999). Inorg. Chem. 39, 2397–2404. [DOI] [PubMed]
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051627/nk2079sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051627/nk2079Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report