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A novel Ni2+ complex with the N4-donor tripodal ligand bis[(1-methyl-1H-imidazol-2-yl)methyl][2-(pyridin-2-yl)ethyl]amine (L), namely, aqua{bis[(1-methyl-1H-imidazol-2-yl-κN3)methyl][2-(pyridin-2-yl-κN)ethyl]amine-κN}chloridonickel(II) perchlorate, [NiCl(C17H22N6)(H2O)]ClO4 or [NiCl(H2O)(L)Cl]ClO4 (1), was synthesized and characterized by spectroscopic and spectrometric methods. The crystal structure of 1 reveals an interesting and unusual cocrystallization of isomeric complexes, which are crystallographically disordered with partial occupancy of the labile cis aqua and chloride ligands. The Ni2+ centre exhibits a distorted octahedral environment, with similar bond lengths for the two Ni—N(imidazole) bonds. The bond length increases for Ni—N(pyridine) and Ni—N(amine), which is in agreement with literature examples. The bond lengths of the disordered labile sites are also in the expected range and the Ni—Cl and Ni—O bond lengths are comparable with similar compounds. The electronic, redox and solution stability behaviour of 1 were also evaluated, and the data obtained suggest the maintenance of structural integrity, with no sign of demetalation or decomposition under the studied conditions.
Supporting information
CCDC reference: 1966871
Data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009) and OLEX2 (Dolomanov et al.,
2009); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015) and publCIF (Westrip, 2010).
Aqua{bis[(1-methyl-1
H-imidazol-2-yl-
κN3)methyl][2-(pyridin-2-yl-
κN)ethyl]amine-
κN}chloridonickel(II) perchlorate,
top
Crystal data top
[NiCl(C17H22N6)(H2O)]ClO4 | Dx = 1.565 Mg m−3 |
Mr = 522.03 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcn | Cell parameters from 9412 reflections |
a = 26.8563 (8) Å | θ = 2.7–25.9° |
b = 13.4519 (5) Å | µ = 1.16 mm−1 |
c = 12.2659 (3) Å | T = 288 K |
V = 4431.3 (2) Å3 | Prismatic, blue |
Z = 8 | 0.40 × 0.12 × 0.06 mm |
F(000) = 2160 | |
Data collection top
Bruker APEXII DUO diffractometer | 4377 independent reflections |
Radiation source: fine-focus sealed tube | 3056 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 26.1°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −31→33 |
Tmin = 0.667, Tmax = 0.745 | k = −16→16 |
10766 measured reflections | l = −14→15 |
Refinement top
Refinement on F2 | 160 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.112 | w = 1/[σ2(Fo2) + (0.0367P)2 + 3.4181P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.002 |
4377 reflections | Δρmax = 0.36 e Å−3 |
337 parameters | Δρmin = −0.44 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Ni1 | 0.43792 (2) | 0.67880 (3) | 0.48830 (3) | 0.03910 (14) | |
Cl1 | 0.5026 (3) | 0.6241 (7) | 0.3737 (7) | 0.0448 (9) | 0.5 |
O1W | 0.4657 (6) | 0.5958 (16) | 0.6290 (14) | 0.045 (3) | 0.5 |
Cl2 | 0.4753 (3) | 0.6073 (7) | 0.6513 (6) | 0.0529 (11) | 0.5 |
O2W | 0.4920 (7) | 0.6121 (17) | 0.3795 (18) | 0.046 (5) | 0.5 |
N1 | 0.37057 (9) | 0.7219 (2) | 0.5743 (2) | 0.0447 (7) | |
C1 | 0.38090 (14) | 0.8008 (3) | 0.6553 (3) | 0.0620 (11) | |
H1A | 0.402294 | 0.774119 | 0.711881 | 0.074* | |
H1B | 0.349850 | 0.820895 | 0.689163 | 0.074* | |
C2 | 0.40584 (15) | 0.8920 (3) | 0.6050 (4) | 0.0701 (12) | |
H2A | 0.390708 | 0.904731 | 0.534600 | 0.084* | |
H2B | 0.399080 | 0.949004 | 0.651128 | 0.084* | |
C10 | 0.35277 (13) | 0.6303 (3) | 0.6280 (3) | 0.0549 (9) | |
H10A | 0.317592 | 0.635995 | 0.644803 | 0.066* | |
H10B | 0.370793 | 0.619509 | 0.695498 | 0.066* | |
C11 | 0.36135 (12) | 0.5458 (3) | 0.5518 (3) | 0.0488 (8) | |
N12 | 0.39426 (9) | 0.5540 (2) | 0.4724 (2) | 0.0458 (7) | |
C13 | 0.39418 (13) | 0.4629 (3) | 0.4206 (3) | 0.0572 (10) | |
H13 | 0.413749 | 0.446111 | 0.360811 | 0.069* | |
C14 | 0.36152 (15) | 0.4025 (3) | 0.4698 (4) | 0.0713 (12) | |
H14 | 0.354247 | 0.337205 | 0.450467 | 0.086* | |
N15 | 0.34085 (11) | 0.4552 (2) | 0.5542 (3) | 0.0623 (9) | |
C16 | 0.30386 (17) | 0.4190 (4) | 0.6332 (5) | 0.0974 (17) | |
H16A | 0.316580 | 0.427214 | 0.705787 | 0.146* | |
H16B | 0.297253 | 0.349959 | 0.619963 | 0.146* | |
H16C | 0.273609 | 0.456394 | 0.625420 | 0.146* | |
C20 | 0.33286 (12) | 0.7549 (3) | 0.4930 (3) | 0.0520 (9) | |
H20A | 0.308176 | 0.703020 | 0.483093 | 0.062* | |
H20B | 0.315977 | 0.813787 | 0.519732 | 0.062* | |
C21 | 0.35679 (11) | 0.7772 (2) | 0.3874 (3) | 0.0452 (8) | |
N22 | 0.40383 (9) | 0.7568 (2) | 0.3660 (2) | 0.0464 (7) | |
C23 | 0.41182 (13) | 0.7862 (3) | 0.2604 (3) | 0.0541 (9) | |
H23 | 0.441926 | 0.781371 | 0.223295 | 0.065* | |
C24 | 0.36944 (14) | 0.8230 (3) | 0.2190 (3) | 0.0595 (10) | |
H24 | 0.364778 | 0.847898 | 0.148964 | 0.071* | |
N25 | 0.33436 (10) | 0.8170 (2) | 0.2997 (3) | 0.0521 (7) | |
C26 | 0.28140 (13) | 0.8433 (3) | 0.2907 (4) | 0.0718 (12) | |
H26A | 0.277654 | 0.897850 | 0.240958 | 0.108* | |
H26B | 0.268948 | 0.862117 | 0.361106 | 0.108* | |
H26C | 0.263020 | 0.787044 | 0.264216 | 0.108* | |
C31 | 0.46127 (14) | 0.8835 (3) | 0.5898 (3) | 0.0618 (10) | |
N32 | 0.47990 (11) | 0.8010 (2) | 0.5425 (3) | 0.0575 (8) | |
C33 | 0.52990 (13) | 0.7927 (3) | 0.5341 (4) | 0.0682 (12) | |
H33 | 0.543029 | 0.735038 | 0.503717 | 0.082* | |
C34 | 0.56224 (16) | 0.8654 (4) | 0.5683 (4) | 0.0809 (13) | |
H34 | 0.596467 | 0.857145 | 0.561192 | 0.097* | |
C35 | 0.54289 (19) | 0.9504 (4) | 0.6131 (4) | 0.0812 (14) | |
H35 | 0.563860 | 1.001314 | 0.635820 | 0.097* | |
C36 | 0.49232 (17) | 0.9594 (3) | 0.6239 (4) | 0.0738 (12) | |
H36 | 0.478835 | 1.016758 | 0.654292 | 0.089* | |
Cl3 | 0.70931 (3) | 0.90627 (8) | 0.56734 (9) | 0.0623 (3) | |
O1P | 0.6945 (5) | 0.8122 (7) | 0.5521 (15) | 0.156 (8) | 0.471 (12) |
O2P | 0.7494 (5) | 0.9106 (11) | 0.6362 (14) | 0.162 (8) | 0.471 (12) |
O3P | 0.6700 (3) | 0.9562 (8) | 0.6232 (12) | 0.109 (5) | 0.471 (12) |
O4P | 0.7177 (8) | 0.9579 (14) | 0.4772 (9) | 0.236 (9) | 0.471 (12) |
O1P' | 0.7105 (5) | 0.8231 (8) | 0.4987 (12) | 0.156 (7) | 0.529 (12) |
O2P' | 0.7576 (2) | 0.9360 (8) | 0.5827 (9) | 0.097 (4) | 0.529 (12) |
O3P' | 0.6887 (6) | 0.8824 (17) | 0.6608 (9) | 0.253 (9) | 0.529 (12) |
O4P' | 0.6833 (4) | 0.9777 (5) | 0.5132 (12) | 0.130 (5) | 0.529 (12) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0327 (2) | 0.0479 (3) | 0.0367 (2) | 0.00684 (18) | −0.00061 (17) | 0.00159 (18) |
Cl1 | 0.040 (2) | 0.049 (2) | 0.0453 (16) | 0.0000 (19) | 0.0045 (15) | −0.0010 (13) |
O1W | 0.056 (7) | 0.048 (5) | 0.032 (6) | 0.007 (5) | −0.018 (4) | 0.000 (4) |
Cl2 | 0.055 (2) | 0.059 (3) | 0.044 (3) | 0.0133 (18) | −0.0071 (19) | 0.010 (2) |
O2W | 0.036 (8) | 0.046 (7) | 0.055 (6) | −0.003 (5) | 0.005 (5) | −0.001 (4) |
N1 | 0.0387 (13) | 0.0500 (17) | 0.0453 (16) | 0.0087 (13) | 0.0041 (12) | −0.0011 (13) |
C1 | 0.055 (2) | 0.075 (3) | 0.056 (2) | 0.012 (2) | 0.0043 (18) | −0.021 (2) |
C2 | 0.067 (2) | 0.057 (3) | 0.086 (3) | 0.009 (2) | −0.003 (2) | −0.024 (2) |
C10 | 0.0478 (18) | 0.070 (2) | 0.047 (2) | 0.0071 (19) | 0.0101 (16) | 0.0075 (19) |
C11 | 0.0384 (16) | 0.056 (2) | 0.052 (2) | 0.0037 (17) | −0.0005 (16) | 0.0089 (17) |
N12 | 0.0385 (13) | 0.0517 (17) | 0.0472 (16) | 0.0027 (13) | 0.0006 (12) | 0.0006 (13) |
C13 | 0.0433 (18) | 0.062 (2) | 0.066 (2) | 0.0035 (19) | −0.0034 (18) | −0.012 (2) |
C14 | 0.057 (2) | 0.052 (2) | 0.105 (4) | −0.001 (2) | −0.004 (2) | −0.012 (2) |
N15 | 0.0443 (15) | 0.056 (2) | 0.087 (2) | −0.0020 (15) | 0.0057 (16) | 0.0194 (18) |
C16 | 0.075 (3) | 0.085 (3) | 0.132 (5) | −0.006 (3) | 0.034 (3) | 0.035 (3) |
C20 | 0.0372 (15) | 0.059 (2) | 0.060 (2) | 0.0121 (16) | 0.0007 (16) | −0.0009 (18) |
C21 | 0.0394 (16) | 0.0430 (19) | 0.053 (2) | 0.0071 (15) | −0.0082 (16) | 0.0001 (16) |
N22 | 0.0390 (13) | 0.0510 (17) | 0.0490 (16) | 0.0072 (13) | 0.0003 (13) | 0.0070 (14) |
C23 | 0.053 (2) | 0.056 (2) | 0.054 (2) | 0.0071 (18) | 0.0003 (18) | 0.0102 (18) |
C24 | 0.069 (2) | 0.058 (2) | 0.051 (2) | 0.006 (2) | −0.0113 (19) | 0.0107 (19) |
N25 | 0.0454 (15) | 0.0483 (17) | 0.0626 (19) | 0.0076 (14) | −0.0145 (15) | 0.0021 (15) |
C26 | 0.049 (2) | 0.075 (3) | 0.091 (3) | 0.016 (2) | −0.025 (2) | −0.001 (2) |
C31 | 0.059 (2) | 0.057 (2) | 0.069 (3) | 0.003 (2) | −0.010 (2) | −0.007 (2) |
N32 | 0.0436 (15) | 0.055 (2) | 0.074 (2) | 0.0024 (14) | −0.0038 (15) | −0.0037 (16) |
C33 | 0.0392 (18) | 0.077 (3) | 0.088 (3) | 0.000 (2) | −0.008 (2) | 0.003 (2) |
C34 | 0.053 (2) | 0.099 (4) | 0.091 (3) | −0.019 (3) | −0.010 (2) | 0.007 (3) |
C35 | 0.084 (3) | 0.082 (3) | 0.078 (3) | −0.029 (3) | −0.022 (3) | 0.005 (3) |
C36 | 0.087 (3) | 0.061 (3) | 0.074 (3) | −0.004 (2) | −0.016 (2) | −0.005 (2) |
Cl3 | 0.0433 (5) | 0.0651 (6) | 0.0785 (7) | −0.0080 (5) | −0.0050 (5) | −0.0035 (5) |
O1P | 0.126 (9) | 0.035 (5) | 0.31 (2) | −0.027 (5) | −0.042 (12) | −0.020 (8) |
O2P | 0.163 (13) | 0.127 (11) | 0.197 (15) | 0.067 (9) | −0.148 (11) | −0.090 (10) |
O3P | 0.062 (4) | 0.102 (7) | 0.163 (11) | −0.012 (4) | 0.021 (6) | −0.048 (7) |
O4P | 0.31 (2) | 0.29 (2) | 0.105 (8) | −0.091 (17) | 0.053 (13) | 0.063 (11) |
O1P' | 0.172 (12) | 0.115 (10) | 0.180 (11) | 0.047 (8) | −0.124 (10) | −0.077 (8) |
O2P' | 0.033 (3) | 0.091 (6) | 0.167 (11) | −0.013 (4) | 0.005 (5) | −0.025 (6) |
O3P' | 0.191 (14) | 0.42 (2) | 0.144 (10) | −0.069 (16) | 0.071 (10) | 0.113 (14) |
O4P' | 0.108 (7) | 0.063 (5) | 0.220 (14) | 0.034 (4) | −0.085 (8) | 0.013 (6) |
Geometric parameters (Å, º) top
Ni1—N22 | 2.047 (3) | C20—H20A | 0.9700 |
Ni1—N12 | 2.057 (3) | C20—H20B | 0.9700 |
Ni1—N32 | 2.101 (3) | C21—N22 | 1.319 (4) |
Ni1—O2W | 2.17 (2) | C21—N25 | 1.344 (4) |
Ni1—N1 | 2.173 (3) | N22—C23 | 1.371 (4) |
Ni1—O1W | 2.186 (19) | C23—C24 | 1.341 (5) |
Ni1—Cl1 | 2.352 (8) | C23—H23 | 0.9300 |
Ni1—Cl2 | 2.435 (7) | C24—N25 | 1.369 (5) |
N1—C10 | 1.477 (4) | C24—H24 | 0.9300 |
N1—C1 | 1.480 (4) | N25—C26 | 1.470 (4) |
N1—C20 | 1.489 (4) | C26—H26A | 0.9600 |
C1—C2 | 1.528 (5) | C26—H26B | 0.9600 |
C1—H1A | 0.9700 | C26—H26C | 0.9600 |
C1—H1B | 0.9700 | C31—N32 | 1.349 (5) |
C2—C31 | 1.505 (5) | C31—C36 | 1.383 (5) |
C2—H2A | 0.9700 | N32—C33 | 1.351 (4) |
C2—H2B | 0.9700 | C33—C34 | 1.373 (6) |
C10—C11 | 1.490 (5) | C33—H33 | 0.9300 |
C10—H10A | 0.9700 | C34—C35 | 1.370 (7) |
C10—H10B | 0.9700 | C34—H34 | 0.9300 |
C11—N12 | 1.320 (4) | C35—C36 | 1.370 (6) |
C11—N15 | 1.338 (4) | C35—H35 | 0.9300 |
N12—C13 | 1.380 (4) | C36—H36 | 0.9300 |
C13—C14 | 1.340 (5) | Cl3—O3P' | 1.313 (8) |
C13—H13 | 0.9300 | Cl3—O4P | 1.325 (9) |
C14—N15 | 1.372 (5) | Cl3—O1P | 1.339 (8) |
C14—H14 | 0.9300 | Cl3—O4P' | 1.361 (6) |
N15—C16 | 1.470 (5) | Cl3—O2P' | 1.370 (6) |
C16—H16A | 0.9600 | Cl3—O2P | 1.370 (9) |
C16—H16B | 0.9600 | Cl3—O1P' | 1.400 (9) |
C16—H16C | 0.9600 | Cl3—O3P | 1.426 (7) |
C20—C21 | 1.476 (5) | | |
| | | |
N22—Ni1—N12 | 95.39 (11) | N15—C16—H16A | 109.5 |
N22—Ni1—N32 | 94.05 (12) | N15—C16—H16B | 109.5 |
N12—Ni1—N32 | 167.01 (12) | H16A—C16—H16B | 109.5 |
N22—Ni1—O2W | 93.5 (6) | N15—C16—H16C | 109.5 |
N12—Ni1—O2W | 89.2 (5) | H16A—C16—H16C | 109.5 |
N32—Ni1—O2W | 99.2 (5) | H16B—C16—H16C | 109.5 |
N22—Ni1—N1 | 81.17 (10) | C21—C20—N1 | 110.6 (3) |
N12—Ni1—N1 | 77.85 (11) | C21—C20—H20A | 109.5 |
N32—Ni1—N1 | 94.83 (11) | N1—C20—H20A | 109.5 |
O2W—Ni1—N1 | 165.3 (5) | C21—C20—H20B | 109.5 |
N22—Ni1—O1W | 173.1 (5) | N1—C20—H20B | 109.5 |
N12—Ni1—O1W | 81.6 (5) | H20A—C20—H20B | 108.1 |
N32—Ni1—O1W | 88.1 (5) | N22—C21—N25 | 110.6 (3) |
N1—Ni1—O1W | 92.2 (5) | N22—C21—C20 | 123.3 (3) |
N22—Ni1—Cl1 | 93.0 (2) | N25—C21—C20 | 126.0 (3) |
N12—Ni1—Cl1 | 96.3 (2) | C21—N22—C23 | 106.2 (3) |
N32—Ni1—Cl1 | 92.1 (2) | C21—N22—Ni1 | 112.9 (2) |
N1—Ni1—Cl1 | 171.2 (2) | C23—N22—Ni1 | 140.4 (2) |
O1W—Ni1—Cl1 | 93.4 (6) | C24—C23—N22 | 109.4 (3) |
N22—Ni1—Cl2 | 171.3 (2) | C24—C23—H23 | 125.3 |
N12—Ni1—Cl2 | 89.4 (2) | N22—C23—H23 | 125.3 |
N32—Ni1—Cl2 | 80.1 (2) | C23—C24—N25 | 106.7 (3) |
O2W—Ni1—Cl2 | 93.8 (6) | C23—C24—H24 | 126.6 |
N1—Ni1—Cl2 | 92.8 (2) | N25—C24—H24 | 126.6 |
C10—N1—C1 | 111.1 (3) | C21—N25—C24 | 107.1 (3) |
C10—N1—C20 | 109.1 (3) | C21—N25—C26 | 126.1 (3) |
C1—N1—C20 | 111.3 (3) | C24—N25—C26 | 126.7 (3) |
C10—N1—Ni1 | 105.25 (19) | N25—C26—H26A | 109.5 |
C1—N1—Ni1 | 111.2 (2) | N25—C26—H26B | 109.5 |
C20—N1—Ni1 | 108.69 (19) | H26A—C26—H26B | 109.5 |
N1—C1—C2 | 112.8 (3) | N25—C26—H26C | 109.5 |
N1—C1—H1A | 109.0 | H26A—C26—H26C | 109.5 |
C2—C1—H1A | 109.0 | H26B—C26—H26C | 109.5 |
N1—C1—H1B | 109.0 | N32—C31—C36 | 120.9 (4) |
C2—C1—H1B | 109.0 | N32—C31—C2 | 118.9 (3) |
H1A—C1—H1B | 107.8 | C36—C31—C2 | 120.2 (4) |
C31—C2—C1 | 115.0 (3) | C31—N32—C33 | 118.0 (4) |
C31—C2—H2A | 108.5 | C31—N32—Ni1 | 125.5 (2) |
C1—C2—H2A | 108.5 | C33—N32—Ni1 | 116.4 (3) |
C31—C2—H2B | 108.5 | N32—C33—C34 | 123.1 (4) |
C1—C2—H2B | 108.5 | N32—C33—H33 | 118.4 |
H2A—C2—H2B | 107.5 | C34—C33—H33 | 118.4 |
N1—C10—C11 | 107.9 (3) | C35—C34—C33 | 118.5 (4) |
N1—C10—H10A | 110.1 | C35—C34—H34 | 120.8 |
C11—C10—H10A | 110.1 | C33—C34—H34 | 120.8 |
N1—C10—H10B | 110.1 | C36—C35—C34 | 119.3 (4) |
C11—C10—H10B | 110.1 | C36—C35—H35 | 120.4 |
H10A—C10—H10B | 108.4 | C34—C35—H35 | 120.4 |
N12—C11—N15 | 111.6 (3) | C35—C36—C31 | 120.2 (4) |
N12—C11—C10 | 120.2 (3) | C35—C36—H36 | 119.9 |
N15—C11—C10 | 128.2 (3) | C31—C36—H36 | 119.9 |
C11—N12—C13 | 105.3 (3) | O4P—Cl3—O1P | 115.4 (8) |
C11—N12—Ni1 | 112.3 (2) | O3P'—Cl3—O4P' | 112.5 (8) |
C13—N12—Ni1 | 140.3 (2) | O3P'—Cl3—O2P' | 110.5 (7) |
C14—C13—N12 | 109.4 (4) | O4P'—Cl3—O2P' | 110.3 (6) |
C14—C13—H13 | 125.3 | O4P—Cl3—O2P | 111.0 (8) |
N12—C13—H13 | 125.3 | O1P—Cl3—O2P | 111.1 (8) |
C13—C14—N15 | 106.9 (3) | O3P'—Cl3—O1P' | 109.8 (8) |
C13—C14—H14 | 126.5 | O4P'—Cl3—O1P' | 106.4 (6) |
N15—C14—H14 | 126.5 | O2P'—Cl3—O1P' | 107.1 (7) |
C11—N15—C14 | 106.7 (3) | O4P—Cl3—O3P | 106.2 (8) |
C11—N15—C16 | 126.4 (4) | O1P—Cl3—O3P | 107.0 (7) |
C14—N15—C16 | 126.9 (4) | O2P—Cl3—O3P | 105.4 (7) |
| | | |
C10—N1—C1—C2 | 172.4 (3) | N25—C21—N22—C23 | 0.8 (4) |
C20—N1—C1—C2 | −65.8 (4) | C20—C21—N22—C23 | 178.8 (3) |
Ni1—N1—C1—C2 | 55.5 (3) | N25—C21—N22—Ni1 | −172.1 (2) |
N1—C1—C2—C31 | −82.0 (4) | C20—C21—N22—Ni1 | 5.8 (4) |
C1—N1—C10—C11 | −159.0 (3) | C21—N22—C23—C24 | −0.6 (4) |
C20—N1—C10—C11 | 77.9 (3) | Ni1—N22—C23—C24 | 169.2 (3) |
Ni1—N1—C10—C11 | −38.6 (3) | N22—C23—C24—N25 | 0.2 (4) |
N1—C10—C11—N12 | 20.6 (4) | N22—C21—N25—C24 | −0.8 (4) |
N1—C10—C11—N15 | −162.5 (3) | C20—C21—N25—C24 | −178.6 (3) |
N15—C11—N12—C13 | 0.6 (4) | N22—C21—N25—C26 | 176.0 (3) |
C10—C11—N12—C13 | 178.0 (3) | C20—C21—N25—C26 | −1.9 (6) |
N15—C11—N12—Ni1 | −166.5 (2) | C23—C24—N25—C21 | 0.3 (4) |
C10—C11—N12—Ni1 | 10.9 (4) | C23—C24—N25—C26 | −176.3 (3) |
C11—N12—C13—C14 | −0.1 (4) | C1—C2—C31—N32 | 48.2 (5) |
Ni1—N12—C13—C14 | 161.0 (3) | C1—C2—C31—C36 | −131.8 (4) |
N12—C13—C14—N15 | −0.4 (4) | C36—C31—N32—C33 | 3.1 (6) |
N12—C11—N15—C14 | −0.9 (4) | C2—C31—N32—C33 | −177.0 (4) |
C10—C11—N15—C14 | −178.0 (3) | C36—C31—N32—Ni1 | 179.2 (3) |
N12—C11—N15—C16 | 178.3 (4) | C2—C31—N32—Ni1 | −0.9 (6) |
C10—C11—N15—C16 | 1.2 (6) | C31—N32—C33—C34 | −2.1 (7) |
C13—C14—N15—C11 | 0.8 (4) | Ni1—N32—C33—C34 | −178.5 (4) |
C13—C14—N15—C16 | −178.4 (4) | N32—C33—C34—C35 | 0.0 (7) |
C10—N1—C20—C21 | −131.5 (3) | C33—C34—C35—C36 | 1.1 (7) |
C1—N1—C20—C21 | 105.5 (3) | C34—C35—C36—C31 | −0.1 (7) |
Ni1—N1—C20—C21 | −17.3 (4) | N32—C31—C36—C35 | −2.0 (7) |
N1—C20—C21—N22 | 8.7 (5) | C2—C31—C36—C35 | 178.0 (4) |
N1—C20—C21—N25 | −173.7 (3) | | |
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