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Acta Cryst. (2007). E63, m2026    [ doi:10.1107/S160053680703108X ]

Bis[N-ethyl-N'-(pyridin-2-ylmethylene)ethane-1,2-diamine]nickel(II) bis(perchlorate)

Z. Hong

Abstract top

The asymmetric unit of the title compound, [Ni(C10H15N3)2](ClO4)2, consists of 1.5 mononuclear nickel(II) complex cations, two perchlorate anions and two half-perchlorate anions. One of the complex cations and two of the perchlorate anions possess crystallographic twofold rotation symmetry. The Ni atom is coordinated by six N atoms from two N-ethyl-N'-(pyridin-2-ylmethylene)ethane-1,2-diamine ligands in a slightly distorted octahedral geometry. All chemically equivalent bond lengths and angles in the two complex molecules are comparable with each other. Each ligand adopts an approximately planar geometry, except for the terminal ethyl groups. The crystal structure involves intermolecular N-H...O hydrogen bonds.

Comment top

The title complex is a mononuclear nickel(II) compound (Fig. 1). The structure consists of two mononuclear nickel(II) molecules, one with twofold symmetry, and four perchlorate anions, two with twofold symmetry. The Ni atom is six-coordinated by two Schiff base ligands. Each Schiff base ligand acts as a tridentate ligand, and ligates to the nickel atom through the imine N, amine N, and pyridine N atoms. The bond lengths related to the metal centres are comparable to the values in other similar nickel(II) complexes (Zhou et al., 2004; Li et al., 2005; Li et al., 2007).

Related literature top

For related literature, see: Li et al. (2005, 2007); Zhou et al. (2004).

Experimental top

All the reagents used were of commercial grade and used without further purification. N-Ethylethane-1,2-diamine (1.0 mmol, 88.2 mg) and pyridine-2-carbaldehyde (1.0 mmol, 107.1 mg) were mixed in a methanol solution (10 ml). The mixture was stirred for 1 h at room temperature. To the mixture was added with stirring a methanol solution (10 ml) of Ni(ClO4)2·7H2O (0.5 mmol, 192.0 mg). After keeping the filtrate in air for a week, green block-shaped crystals were formed.

Refinement top

H atoms were placed in idealized positions and constrained to ride on their parent atoms with C–H distances in the range 0.93–0.97 Å, N–H distances of 0.91 Å, and with Uiso(H) set at 1.2Ueq(C,N) and 1.5Ueq(methyl C). The structure contains solvent accessible voids of 65 Å3, which might accommodate a disordered methanol molecule.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The structure of compound (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
Bis[N-ethyl-N'-(pyridin-2-ylmethylene)ethane-1,2-diamine]nickel(II) bis(perchlorate) top
Crystal data top
[Ni(C10H15N3)2](ClO4)2F000 = 1908
Mr = 612.11Dx = 1.470 Mg m−3
Monoclinic, P2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 5221 reflections
a = 21.1172 (18) Åθ = 2.3–24.9º
b = 16.8787 (14) ŵ = 0.95 mm−1
c = 12.0819 (10) ÅT = 298 (2) K
β = 105.5310 (10)ºBlock, green
V = 4149.1 (6) Å30.37 × 0.35 × 0.32 mm
Z = 6
Data collection top
Bruker SMART CCD area-detector
diffractometer		9187 independent reflections
Radiation source: fine-focus sealed tube5711 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.033
T = 298(2) Kθmax = 27.5º
ω scansθmin = 2.4º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −27→23
Tmin = 0.721, Tmax = 0.751k = −20→21
23631 measured reflectionsl = −8→15
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.189  w = 1/[σ2(Fo2) + (0.1156P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
9187 reflectionsΔρmax = 1.86 e Å−3
505 parametersΔρmin = −0.47 e Å−3
18 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ni(C10H15N3)2](ClO4)2V = 4149.1 (6) Å3
Mr = 612.11Z = 6
Monoclinic, P2/cMo Kα
a = 21.1172 (18) ŵ = 0.95 mm−1
b = 16.8787 (14) ÅT = 298 (2) K
c = 12.0819 (10) Å0.37 × 0.35 × 0.32 mm
β = 105.5310 (10)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		9187 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5711 reflections with I > 2σ(I)
Tmin = 0.721, Tmax = 0.751Rint = 0.033
23631 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05918 restraints
wR(F2) = 0.189H-atom parameters constrained
S = 0.99Δρmax = 1.86 e Å−3
9187 reflectionsΔρmin = −0.47 e Å−3
505 parameters
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 > 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) top
xyzUiso*/Ueq
Ni10.31911 (2)0.27828 (3)0.42248 (4)0.04209 (16)
Ni20.00000.19438 (4)0.75000.04130 (19)
Cl10.20287 (5)0.59652 (6)0.53647 (9)0.0550 (3)
Cl20.30375 (6)0.93789 (9)0.53709 (11)0.0734 (3)
Cl30.50000.44214 (9)0.75000.0589 (4)
Cl41.00000.88866 (11)0.75000.0808 (5)
O10.1344 (2)0.5861 (3)0.4961 (4)0.0975 (13)
O20.2341 (3)0.5720 (3)0.4539 (4)0.1139 (15)
O30.2268 (2)0.5531 (3)0.6417 (3)0.0907 (12)
O40.2134 (2)0.6791 (2)0.5604 (4)0.1028 (14)
O50.2732 (3)0.8631 (3)0.5367 (4)0.1117 (15)
O60.3564 (3)0.9301 (4)0.4928 (6)0.139 (2)
O70.3176 (4)0.9736 (5)0.6419 (7)0.178 (3)
O80.2592 (3)0.9910 (4)0.4709 (7)0.165 (3)
O90.44959 (18)0.3930 (2)0.7721 (4)0.0946 (13)
O100.4710 (2)0.4896 (3)0.6554 (4)0.0968 (13)
O110.9805 (6)0.8420 (7)0.8234 (9)0.247 (4)
O120.9476 (4)0.9348 (5)0.6847 (8)0.202 (4)
N10.41192 (17)0.22489 (19)0.4957 (3)0.0490 (8)
N20.30283 (18)0.1667 (2)0.3666 (3)0.0523 (8)
N30.21667 (17)0.2880 (2)0.3311 (3)0.0538 (8)
H3A0.21570.30140.25770.065*
N40.30009 (16)0.26354 (19)0.5868 (3)0.0479 (7)
N50.33348 (16)0.38789 (17)0.4875 (3)0.0467 (7)
N60.35160 (17)0.3331 (2)0.2886 (3)0.0511 (8)
H6A0.31490.34990.23520.061*
N7−0.04676 (17)0.28965 (19)0.8184 (3)0.0489 (8)
N80.05468 (16)0.1998 (2)0.9136 (3)0.0485 (8)
N90.07312 (17)0.1091 (2)0.7407 (3)0.0560 (9)
H9C0.05710.06020.75010.067*
C10.4097 (2)0.1459 (3)0.4762 (4)0.0590 (11)
C20.4615 (3)0.0978 (3)0.5292 (6)0.0881 (17)
H20.45810.04320.51810.106*
C30.5184 (3)0.1296 (4)0.5984 (6)0.0884 (17)
H30.55440.09800.63280.106*
C40.5198 (3)0.2089 (3)0.6140 (5)0.0769 (14)
H40.55770.23270.65890.092*
C50.4661 (2)0.2545 (3)0.5646 (4)0.0585 (10)
H50.46790.30850.58020.070*
C60.3490 (3)0.1178 (3)0.3993 (4)0.0638 (12)
H60.34420.06530.37480.077*
C70.2369 (3)0.1508 (3)0.2934 (5)0.0712 (13)
H7A0.22430.09670.30420.085*
H7B0.23600.15770.21330.085*
C80.1907 (2)0.2069 (3)0.3253 (4)0.0679 (13)
H8A0.14830.20440.26880.081*
H8B0.18450.19210.39930.081*
C90.1764 (2)0.3482 (4)0.3703 (4)0.0725 (14)
H9A0.19970.39830.37980.087*
H9B0.17190.33250.44510.087*
C100.1076 (2)0.3609 (4)0.2898 (5)0.0830 (16)
H10A0.11110.37230.21380.125*
H10B0.08680.40450.31700.125*
H10C0.08190.31380.28810.125*
C110.30700 (18)0.3322 (2)0.6458 (3)0.0481 (9)
C120.2992 (2)0.3359 (3)0.7559 (4)0.0640 (12)
H120.30180.38430.79360.077*
C130.2877 (3)0.2682 (4)0.8086 (4)0.0748 (15)
H130.28280.26980.88280.090*
C140.2833 (2)0.1975 (3)0.7507 (4)0.0704 (13)
H140.27640.15040.78580.084*
C150.2892 (2)0.1974 (3)0.6397 (4)0.0559 (10)
H150.28550.14960.60030.067*
C160.3246 (2)0.3997 (2)0.5852 (4)0.0522 (10)
H160.32910.45010.61760.063*
C170.3510 (2)0.4467 (2)0.4132 (4)0.0590 (11)
H17A0.37850.48740.45880.071*
H17B0.31180.47160.36540.071*
C180.3879 (2)0.4048 (3)0.3391 (4)0.0601 (11)
H18A0.39280.43990.27840.072*
H18B0.43140.39020.38520.072*
C190.3889 (3)0.2821 (3)0.2270 (5)0.0704 (13)
H19A0.36340.23460.20130.084*
H19B0.42960.26590.28130.084*
C200.4055 (3)0.3198 (4)0.1240 (5)0.0900 (17)
H20A0.36790.34810.07910.135*
H20B0.41750.27930.07770.135*
H20C0.44160.35590.15010.135*
C21−0.0118 (2)0.3087 (3)0.9265 (3)0.0511 (9)
C22−0.0265 (3)0.3722 (3)0.9825 (5)0.0741 (14)
H22−0.00160.38391.05650.089*
C23−0.0789 (3)0.4198 (4)0.9291 (6)0.0844 (16)
H23−0.08980.46390.96640.101*
C24−0.1139 (3)0.4012 (3)0.8219 (5)0.0749 (14)
H24−0.14960.43210.78430.090*
C25−0.0962 (2)0.3357 (3)0.7682 (4)0.0604 (11)
H25−0.12030.32380.69370.073*
C260.0431 (2)0.2535 (3)0.9762 (3)0.0551 (10)
H260.06810.25871.05190.066*
C270.1063 (2)0.1424 (3)0.9449 (4)0.0666 (12)
H27A0.09020.09440.97230.080*
H27B0.14230.16301.00570.080*
C280.1292 (2)0.1247 (3)0.8407 (5)0.0752 (14)
H28A0.15410.16940.82430.090*
H28B0.15800.07890.85530.090*
C290.0924 (3)0.1083 (4)0.6315 (5)0.0818 (15)
H29A0.11100.15950.62140.098*
H29B0.05340.10090.56840.098*
C300.1424 (3)0.0436 (4)0.6256 (6)0.099 (2)
H30A0.18610.06430.65370.148*
H30B0.13550.02670.54740.148*
H30C0.1368−0.00060.67200.148*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0470 (3)0.0382 (3)0.0413 (3)−0.00535 (19)0.0122 (2)−0.00498 (18)
Ni20.0396 (4)0.0423 (4)0.0393 (4)0.0000.0057 (3)0.000
Cl10.0577 (6)0.0561 (6)0.0508 (6)−0.0040 (4)0.0138 (4)0.0025 (4)
Cl20.0608 (7)0.0933 (9)0.0646 (7)−0.0078 (6)0.0145 (5)0.0098 (6)
Cl30.0446 (7)0.0530 (8)0.0717 (10)0.0000.0025 (6)0.000
Cl40.0786 (12)0.0614 (10)0.1100 (15)0.0000.0386 (11)0.000
O10.069 (2)0.109 (3)0.103 (3)−0.017 (2)0.004 (2)0.024 (2)
O20.125 (4)0.137 (4)0.098 (3)0.015 (3)0.060 (3)−0.013 (3)
O30.092 (3)0.106 (3)0.067 (2)0.017 (2)0.0094 (19)0.024 (2)
O40.124 (4)0.065 (2)0.115 (3)−0.012 (2)0.025 (3)−0.008 (2)
O50.117 (4)0.105 (3)0.115 (4)−0.020 (3)0.036 (3)0.025 (3)
O60.109 (4)0.147 (5)0.185 (6)−0.011 (4)0.081 (4)−0.002 (4)
O70.194 (6)0.183 (6)0.161 (5)−0.028 (5)0.056 (5)−0.063 (5)
O80.091 (4)0.160 (6)0.225 (7)−0.011 (4)0.009 (4)0.086 (5)
O90.060 (2)0.092 (3)0.125 (3)−0.0135 (19)0.013 (2)0.030 (2)
O100.084 (3)0.101 (3)0.093 (3)0.012 (2)0.003 (2)0.031 (2)
O110.267 (8)0.254 (8)0.222 (7)−0.082 (7)0.068 (6)0.066 (6)
O120.204 (6)0.178 (6)0.202 (7)0.069 (5)0.016 (5)−0.012 (5)
N10.0518 (19)0.0443 (18)0.0517 (19)−0.0033 (14)0.0153 (15)−0.0045 (14)
N20.063 (2)0.0439 (18)0.0500 (19)−0.0118 (16)0.0160 (16)−0.0104 (15)
N30.0504 (19)0.066 (2)0.0447 (18)−0.0030 (16)0.0120 (15)−0.0045 (15)
N40.0466 (18)0.0494 (19)0.0480 (18)−0.0039 (14)0.0129 (14)−0.0027 (14)
N50.0462 (18)0.0368 (16)0.053 (2)−0.0003 (13)0.0055 (14)−0.0031 (14)
N60.0492 (18)0.0555 (19)0.0481 (18)−0.0056 (15)0.0120 (14)0.0019 (15)
N70.0494 (18)0.0518 (19)0.0448 (18)0.0034 (14)0.0116 (14)0.0036 (14)
N80.0454 (18)0.0546 (19)0.0403 (17)0.0012 (14)0.0025 (13)0.0028 (14)
N90.051 (2)0.0526 (19)0.064 (2)0.0048 (15)0.0147 (16)−0.0063 (16)
C10.067 (3)0.046 (2)0.070 (3)0.008 (2)0.029 (2)−0.004 (2)
C20.095 (4)0.062 (3)0.111 (5)0.022 (3)0.032 (4)−0.008 (3)
C30.074 (4)0.087 (4)0.100 (4)0.029 (3)0.016 (3)0.000 (3)
C40.061 (3)0.085 (4)0.082 (4)0.004 (3)0.015 (3)−0.005 (3)
C50.058 (3)0.061 (3)0.058 (3)0.004 (2)0.017 (2)−0.003 (2)
C60.084 (3)0.038 (2)0.073 (3)−0.005 (2)0.026 (2)−0.014 (2)
C70.077 (3)0.064 (3)0.070 (3)−0.027 (2)0.015 (2)−0.017 (2)
C80.063 (3)0.079 (3)0.060 (3)−0.024 (2)0.014 (2)−0.011 (2)
C90.055 (3)0.105 (4)0.055 (3)0.008 (3)0.009 (2)−0.012 (3)
C100.055 (3)0.115 (4)0.080 (4)0.011 (3)0.019 (2)−0.003 (3)
C110.0379 (19)0.059 (2)0.045 (2)−0.0020 (16)0.0080 (15)−0.0121 (18)
C120.058 (3)0.085 (3)0.051 (2)−0.012 (2)0.018 (2)−0.023 (2)
C130.069 (3)0.113 (4)0.046 (2)−0.023 (3)0.022 (2)−0.014 (3)
C140.065 (3)0.088 (3)0.060 (3)−0.017 (3)0.019 (2)0.015 (3)
C150.060 (3)0.056 (2)0.055 (2)−0.0085 (19)0.0208 (19)−0.0024 (19)
C160.055 (2)0.042 (2)0.054 (2)0.0034 (17)0.0044 (18)−0.0133 (17)
C170.074 (3)0.040 (2)0.059 (3)−0.0061 (19)0.009 (2)0.0025 (18)
C180.060 (3)0.055 (2)0.065 (3)−0.009 (2)0.016 (2)0.013 (2)
C190.080 (3)0.069 (3)0.070 (3)−0.010 (2)0.035 (3)−0.009 (2)
C200.094 (4)0.117 (5)0.071 (3)−0.004 (4)0.043 (3)−0.005 (3)
C210.055 (2)0.055 (2)0.045 (2)−0.0008 (18)0.0146 (17)−0.0033 (18)
C220.073 (3)0.087 (4)0.063 (3)0.003 (3)0.019 (2)−0.023 (3)
C230.080 (4)0.073 (3)0.109 (5)0.017 (3)0.040 (3)−0.014 (3)
C240.075 (3)0.066 (3)0.085 (4)0.026 (2)0.024 (3)0.009 (3)
C250.063 (3)0.061 (3)0.055 (2)0.018 (2)0.012 (2)0.008 (2)
C260.054 (2)0.069 (3)0.039 (2)0.000 (2)0.0057 (17)−0.0001 (19)
C270.068 (3)0.069 (3)0.053 (3)0.019 (2)−0.002 (2)0.007 (2)
C280.049 (3)0.079 (3)0.090 (4)0.017 (2)0.006 (2)0.002 (3)
C290.075 (4)0.082 (4)0.095 (4)0.003 (3)0.035 (3)−0.008 (3)
C300.089 (4)0.091 (4)0.125 (6)0.012 (3)0.044 (4)−0.032 (4)
Geometric parameters (Å, °) top
Ni1—N21.999 (3)C4—H40.9300
Ni1—N52.001 (3)C5—H50.9300
Ni1—N12.123 (3)C6—H60.9300
Ni1—N62.130 (3)C7—C81.483 (7)
Ni1—N42.143 (3)C7—H7A0.9700
Ni1—N32.156 (3)C7—H7B0.9700
Ni2—N8i2.007 (3)C8—H8A0.9700
Ni2—N82.007 (3)C8—H8B0.9700
Ni2—N9i2.136 (3)C9—C101.531 (7)
Ni2—N92.136 (3)C9—H9A0.9700
Ni2—N72.164 (3)C9—H9B0.9700
Ni2—N7i2.164 (3)C10—H10A0.9600
Cl1—O21.398 (4)C10—H10B0.9600
Cl1—O11.407 (4)C10—H10C0.9600
Cl1—O41.429 (4)C11—C121.385 (6)
Cl1—O31.437 (4)C11—C161.456 (6)
Cl2—O71.361 (7)C12—C131.361 (7)
Cl2—O61.363 (5)C12—H120.9300
Cl2—O81.388 (6)C13—C141.374 (8)
Cl2—O51.418 (5)C13—H130.9300
Cl3—O10ii1.396 (4)C14—C151.379 (7)
Cl3—O101.396 (4)C14—H140.9300
Cl3—O9ii1.430 (4)C15—H150.9300
Cl3—O91.430 (4)C16—H160.9300
Cl4—O11iii1.331 (9)C17—C181.510 (7)
Cl4—O111.331 (9)C17—H17A0.9700
Cl4—O12iii1.409 (7)C17—H17B0.9700
Cl4—O121.409 (7)C18—H18A0.9700
N1—C51.320 (6)C18—H18B0.9700
N1—C11.353 (5)C19—C201.520 (8)
N2—C61.257 (6)C19—H19A0.9700
N2—C71.461 (6)C19—H19B0.9700
N3—C81.469 (6)C20—H20A0.9600
N3—C91.482 (6)C20—H20B0.9600
N3—H3A0.9100C20—H20C0.9600
N4—C151.337 (6)C21—C221.348 (7)
N4—C111.348 (5)C21—C261.482 (6)
N5—C161.260 (5)C22—C231.380 (8)
N5—C171.452 (5)C22—H220.9300
N6—C181.473 (5)C23—C241.345 (8)
N6—C191.493 (6)C23—H230.9300
N6—H6A0.9100C24—C251.382 (7)
N7—C251.313 (5)C24—H240.9300
N7—C211.355 (5)C25—H250.9300
N8—C261.245 (6)C26—H260.9300
N8—C271.432 (5)C27—C281.495 (8)
N9—C281.472 (6)C27—H27A0.9700
N9—C291.482 (7)C27—H27B0.9700
N9—H9C0.9100C28—H28A0.9700
C1—C21.375 (7)C28—H28B0.9700
C1—C61.448 (7)C29—C301.533 (8)
C2—C31.376 (9)C29—H29A0.9700
C2—H20.9300C29—H29B0.9700
C3—C41.350 (8)C30—H30A0.9600
C3—H30.9300C30—H30B0.9600
C4—C51.368 (7)C30—H30C0.9600
N2—Ni1—N5176.21 (14)N2—C7—C8108.2 (4)
N2—Ni1—N178.29 (14)N2—C7—H7A110.1
N5—Ni1—N1101.70 (13)C8—C7—H7A110.1
N2—Ni1—N6102.37 (14)N2—C7—H7B110.1
N5—Ni1—N681.42 (14)C8—C7—H7B110.1
N1—Ni1—N692.98 (13)H7A—C7—H7B108.4
N2—Ni1—N498.36 (13)N3—C8—C7110.1 (4)
N5—Ni1—N477.86 (13)N3—C8—H8A109.6
N1—Ni1—N486.88 (13)C7—C8—H8A109.6
N6—Ni1—N4158.80 (13)N3—C8—H8B109.6
N2—Ni1—N380.81 (14)C7—C8—H8B109.6
N5—Ni1—N399.02 (13)H8A—C8—H8B108.1
N1—Ni1—N3158.99 (13)N3—C9—C10114.9 (4)
N6—Ni1—N393.51 (13)N3—C9—H9A108.5
N4—Ni1—N394.12 (13)C10—C9—H9A108.5
N8i—Ni2—N8174.7 (2)N3—C9—H9B108.5
N8i—Ni2—N9i81.35 (14)C10—C9—H9B108.5
N8—Ni2—N9i102.27 (14)H9A—C9—H9B107.5
N8i—Ni2—N9102.27 (14)C9—C10—H10A109.5
N8—Ni2—N981.35 (14)C9—C10—H10B109.5
N9i—Ni2—N995.2 (2)H10A—C10—H10B109.5
N8i—Ni2—N798.11 (13)C9—C10—H10C109.5
N8—Ni2—N777.91 (13)H10A—C10—H10C109.5
N9i—Ni2—N794.05 (14)H10B—C10—H10C109.5
N9—Ni2—N7158.65 (13)N4—C11—C12121.6 (4)
N8i—Ni2—N7i77.91 (13)N4—C11—C16114.4 (4)
N8—Ni2—N7i98.11 (13)C12—C11—C16124.0 (4)
N9i—Ni2—N7i158.65 (13)C13—C12—C11119.5 (4)
N9—Ni2—N7i94.05 (14)C13—C12—H12120.2
N7—Ni2—N7i83.98 (18)C11—C12—H12120.2
O2—Cl1—O1110.6 (3)C12—C13—C14119.2 (4)
O2—Cl1—O4110.8 (3)C12—C13—H13120.4
O1—Cl1—O4106.4 (3)C14—C13—H13120.4
O2—Cl1—O3111.1 (3)C13—C14—C15119.0 (5)
O1—Cl1—O3109.1 (3)C13—C14—H14120.5
O4—Cl1—O3108.6 (3)C15—C14—H14120.5
O7—Cl2—O6114.4 (5)N4—C15—C14122.4 (4)
O7—Cl2—O8101.2 (5)N4—C15—H15118.8
O6—Cl2—O8109.5 (5)C14—C15—H15118.8
O7—Cl2—O5112.4 (4)N5—C16—C11118.0 (3)
O6—Cl2—O5109.4 (4)N5—C16—H16121.0
O8—Cl2—O5109.6 (3)C11—C16—H16121.0
O10ii—Cl3—O10110.0 (4)N5—C17—C18107.7 (3)
O10ii—Cl3—O9ii107.5 (2)N5—C17—H17A110.2
O10—Cl3—O9ii111.4 (3)C18—C17—H17A110.2
O10ii—Cl3—O9111.4 (3)N5—C17—H17B110.2
O10—Cl3—O9107.5 (2)C18—C17—H17B110.2
O9ii—Cl3—O9109.1 (4)H17A—C17—H17B108.5
O11iii—Cl4—O11107.4 (12)N6—C18—C17109.7 (4)
O11iii—Cl4—O12iii111.3 (7)N6—C18—H18A109.7
O11—Cl4—O12iii106.9 (6)C17—C18—H18A109.7
O11iii—Cl4—O12106.9 (6)N6—C18—H18B109.7
O11—Cl4—O12111.3 (7)C17—C18—H18B109.7
O12iii—Cl4—O12112.9 (8)H18A—C18—H18B108.2
C5—N1—C1117.8 (4)N6—C19—C20115.8 (5)
C5—N1—Ni1130.5 (3)N6—C19—H19A108.3
C1—N1—Ni1111.2 (3)C20—C19—H19A108.3
C6—N2—C7127.0 (4)N6—C19—H19B108.3
C6—N2—Ni1117.7 (3)C20—C19—H19B108.3
C7—N2—Ni1115.3 (3)H19A—C19—H19B107.4
C8—N3—C9114.5 (4)C19—C20—H20A109.5
C8—N3—Ni1105.3 (3)C19—C20—H20B109.5
C9—N3—Ni1118.2 (3)H20A—C20—H20B109.5
C8—N3—H3A106.0C19—C20—H20C109.5
C9—N3—H3A106.0H20A—C20—H20C109.5
Ni1—N3—H3A106.0H20B—C20—H20C109.5
C15—N4—C11118.2 (4)C22—C21—N7122.1 (4)
C15—N4—Ni1129.7 (3)C22—C21—C26123.9 (4)
C11—N4—Ni1111.7 (3)N7—C21—C26114.0 (4)
C16—N5—C17126.8 (3)C21—C22—C23119.6 (5)
C16—N5—Ni1118.0 (3)C21—C22—H22120.2
C17—N5—Ni1115.2 (3)C23—C22—H22120.2
C18—N6—C19113.3 (4)C24—C23—C22118.6 (5)
C18—N6—Ni1106.2 (3)C24—C23—H23120.7
C19—N6—Ni1116.6 (3)C22—C23—H23120.7
C18—N6—H6A106.7C23—C24—C25119.4 (5)
C19—N6—H6A106.7C23—C24—H24120.3
Ni1—N6—H6A106.7C25—C24—H24120.3
C25—N7—C21117.8 (4)N7—C25—C24122.5 (5)
C25—N7—Ni2130.7 (3)N7—C25—H25118.7
C21—N7—Ni2110.9 (3)C24—C25—H25118.7
C26—N8—C27126.3 (4)N8—C26—C21118.1 (4)
C26—N8—Ni2118.5 (3)N8—C26—H26121.0
C27—N8—Ni2115.2 (3)C21—C26—H26121.0
C28—N9—C29112.3 (4)N8—C27—C28107.9 (4)
C28—N9—Ni2105.7 (3)N8—C27—H27A110.1
C29—N9—Ni2115.3 (3)C28—C27—H27A110.1
C28—N9—H9C107.8N8—C27—H27B110.1
C29—N9—H9C107.8C28—C27—H27B110.1
Ni2—N9—H9C107.8H27A—C27—H27B108.4
N1—C1—C2121.0 (5)N9—C28—C27110.8 (4)
N1—C1—C6114.7 (4)N9—C28—H28A109.5
C2—C1—C6124.3 (4)C27—C28—H28A109.5
C1—C2—C3120.6 (5)N9—C28—H28B109.5
C1—C2—H2119.7C27—C28—H28B109.5
C3—C2—H2119.7H28A—C28—H28B108.1
C4—C3—C2117.0 (5)N9—C29—C30113.9 (5)
C4—C3—H3121.5N9—C29—H29A108.8
C2—C3—H3121.5C30—C29—H29A108.8
C3—C4—C5120.9 (5)N9—C29—H29B108.8
C3—C4—H4119.6C30—C29—H29B108.8
C5—C4—H4119.6H29A—C29—H29B107.7
N1—C5—C4122.6 (5)C29—C30—H30A109.5
N1—C5—H5118.7C29—C30—H30B109.5
C4—C5—H5118.7H30A—C30—H30B109.5
N2—C6—C1117.7 (4)C29—C30—H30C109.5
N2—C6—H6121.1H30A—C30—H30C109.5
C1—C6—H6121.1H30B—C30—H30C109.5
Symmetry codes: (i) −x, y, −z+3/2; (ii) −x+1, y, −z+3/2; (iii) −x+2, y, −z+3/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O4iv0.912.393.300 (6)173
N6—H6A···O3iv0.912.513.359 (6)156
N6—H6A···O4iv0.912.623.443 (6)150
N9—H9C···O12v0.912.273.141 (9)160
Symmetry codes: (iv) x, −y+1, z−1/2; (v) −x+1, y−1, −z+3/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O4i0.912.393.300 (6)173
N6—H6A···O3i0.912.513.359 (6)156
N6—H6A···O4i0.912.623.443 (6)150
N9—H9C···O12ii0.912.273.141 (9)160
Symmetry codes: (i) x, −y+1, z−1/2; (ii) −x+1, y−1, −z+3/2.
Acknowledgements top

The author acknowledges the Eastern Liaoning University for funding this study.

references
References top

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