supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

hy2244 scheme

Acta Cryst. (2009). E65, m1526-m1527    [ doi:10.1107/S1600536809046042 ]

Diaquabis(N,N'-dibenzylethane-1,2-diamine-[kappa]2N,N')nickel(II) dichloride N,N-dimethylformamide solvate

Y.-F. Liu, H.-T. Xia, D.-Q. Wang and X.-L. Gong

Abstract top

The asymmetric unit of the title complex, [Ni(C16H20N2)2(H2O)2]Cl2·C3H7NO, consists of two NiII atoms, each lying on an inversion center, two Cl anions, two N,N'-dibenzylethane-1,2-diamine ligands, two coordinated water molecules and one N,N-dimethylformamide solvent molecule. Each NiII atom is six-coordinated in a distorted octahedral coordination geometry, with the equatorial plane formed by four N atoms and the axial positions occupied by two water molecules. The complex molecules are linked into a chain along [001] by N-H...Cl, N-H...O and O-H...Cl hydrogen bonds. The C atoms and H atoms of the solvent molecule are disordered over two sites in a ratio of 0.52 (2):0.48 (2).

Comment top

We have reported the crystal structures of nickel complexes with diamine derivatives (Xia et al., 2007a, b). As a further study of the structures of such complexes, we reported here the crystal structure of the title complex.

The NiII atom has a slightly distorted octahedral configuration, coordinated by four N atoms from two N,N'-dibenzylethane-1,2-diamine ligands and two O atoms of two water molecules (Fig. 1 and Table 1). The four N atoms occupy the equatorial positions and O atoms occupy the axial positions. The complex molecules are linked into a chain along the [0 0 1] direction by N—H···Cl and O—H···Cl hydrogen bonds (Table 2). The disordered N,N-dimethylformamide (DMF) solvent molecule is attached to the complex molecule through an N—H···O hydrogen bond.

Related literature top

For related structures, see: Xia et al. (2007a,b).

Experimental top

A solution of N,N'-dibenzylethane-1,2-diamine (1 mmol) in ethanol (20 ml) and a solution of nickel(II) chloride (1 mmol) in ethanol (10 ml) was mixed and the reaction mixture was stirred for 4 h at 328 K. The solution was then cooled slowly to room temperature and filtered. Blue crystals suitable for X-ray diffraction were obtained by evaporation of the ethanol solution.

Refinement top

H atoms were located in difference Fourier maps and refined as riding atoms, with C—H = 0.93 (aryl, formyl), 0.97 (methylene) and 0.96 Å (methyl), N—H = 0.91 Å and O—H = 0.85 Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C,N,O). The C and H atoms in the DMF molecule were found to be disordered over two site. The occupancy factors of the two sites were refined to 0.52 (2) and 0.48 (2). The highest residual electron density was found 0.06 Å from C27 and the deepest hole 0.17 Å from C29.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) 1-x, 1-y, 2-z; (ii) 1-x, 1-y, 1-z.]
Diaquabis(N,N'-dibenzylethane-1,2-diamine- κ2N,N')nickel(II) dichloride N,N-dimethylformamide solvate top
Crystal data top
[Ni(C16H20N2)2(H2O)2]Cl2·C3H7NOZ = 2
Mr = 719.42F(000) = 764
Triclinic, P1Dx = 1.218 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.898 (1) ÅCell parameters from 3426 reflections
b = 12.588 (1) Åθ = 2.4–28.9°
c = 14.872 (2) ŵ = 0.67 mm−1
α = 104.769 (2)°T = 298 K
β = 95.368 (1)°Block, blue
γ = 111.399 (2)°0.42 × 0.40 × 0.35 mm
V = 1961.8 (3) Å3
Data collection top
Siemens SMART 1000 CCD
diffractometer		6781 independent reflections
Radiation source: fine-focus sealed tube4690 reflections with I > 2σ(I)
graphiteRint = 0.018
φ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→12
Tmin = 0.767, Tmax = 0.800k = −14→14
10138 measured reflectionsl = −15→17
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0878P)2 + 5.0932P]
where P = (Fo2 + 2Fc2)/3
6781 reflections(Δ/σ)max = 0.001
450 parametersΔρmax = 1.15 e Å−3
0 restraintsΔρmin = −0.74 e Å−3
Crystal data top
[Ni(C16H20N2)2(H2O)2]Cl2·C3H7NOγ = 111.399 (2)°
Mr = 719.42V = 1961.8 (3) Å3
Triclinic, P1Z = 2
a = 11.898 (1) ÅMo Kα radiation
b = 12.588 (1) ŵ = 0.67 mm−1
c = 14.872 (2) ÅT = 298 K
α = 104.769 (2)°0.42 × 0.40 × 0.35 mm
β = 95.368 (1)°
Data collection top
Siemens SMART 1000 CCD
diffractometer		6781 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4690 reflections with I > 2σ(I)
Tmin = 0.767, Tmax = 0.800Rint = 0.018
10138 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.201Δρmax = 1.15 e Å−3
S = 1.02Δρmin = −0.74 e Å−3
6781 reflectionsAbsolute structure: ?
450 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ni10.50000.50001.00000.0360 (2)
Ni20.50000.50000.50000.0373 (2)
Cl10.61243 (14)0.70108 (13)0.30429 (9)0.0584 (4)
Cl20.68699 (16)0.69555 (13)0.79097 (10)0.0709 (5)
N10.6479 (4)0.6692 (4)1.0730 (3)0.0487 (10)
H10.64810.68221.13610.058*
N20.4030 (4)0.6078 (4)0.9772 (3)0.0523 (11)
H20.33010.57890.99590.063*
N30.6784 (4)0.5756 (4)0.4682 (3)0.0459 (10)
H30.67630.63110.43980.055*
N40.4979 (4)0.3356 (4)0.4135 (3)0.0465 (10)
H40.45400.31800.35430.056*
N50.8816 (7)0.4000 (8)0.7989 (6)0.113 (2)
O10.5688 (3)0.4934 (3)0.8746 (2)0.0506 (9)
H1C0.59800.56260.86760.061*
H1D0.51270.44520.82630.061*
O20.5814 (3)0.4709 (3)0.6187 (2)0.0479 (8)
H2C0.52550.41510.63150.057*
H2D0.60570.53400.66630.057*
O30.8337 (6)0.4541 (7)0.9394 (5)0.118 (2)
C10.6111 (6)0.7603 (5)1.0454 (4)0.0594 (15)
H1A0.62660.76200.98280.071*
H1B0.65940.83951.09040.071*
C20.4762 (6)0.7274 (5)1.0450 (4)0.0616 (15)
H2A0.46140.72811.10810.074*
H2B0.45140.78601.02740.074*
C30.7735 (6)0.6875 (6)1.0621 (5)0.0678 (17)
H3A0.77540.67080.99500.081*
H3B0.79510.62971.08390.081*
C40.8705 (5)0.8117 (5)1.1149 (4)0.0595 (15)
C50.9575 (6)0.8730 (6)1.0714 (5)0.079 (2)
H50.95580.83751.00790.095*
C61.0475 (7)0.9859 (7)1.1193 (6)0.091 (2)
H61.10641.02471.08840.109*
C71.0504 (7)1.0406 (7)1.2117 (6)0.084 (2)
H71.10981.11761.24330.101*
C80.9665 (6)0.9831 (6)1.2580 (5)0.0779 (19)
H80.96811.01981.32120.093*
C90.8785 (6)0.8689 (6)1.2093 (5)0.0721 (18)
H90.82250.82891.24150.087*
C100.3726 (6)0.6090 (6)0.8795 (4)0.0608 (15)
H10A0.31910.52790.84020.073*
H10B0.44820.63230.85560.073*
C110.3108 (7)0.6912 (7)0.8681 (5)0.0738 (18)
C120.3740 (8)0.7947 (7)0.8463 (5)0.087 (2)
H120.45420.81040.83760.105*
C130.3246 (10)0.8759 (8)0.8368 (6)0.105 (3)
H130.36900.94440.82150.127*
C140.2083 (11)0.8505 (9)0.8508 (7)0.111 (3)
H140.17360.90480.84660.134*
C150.1388 (10)0.7483 (10)0.8709 (7)0.114 (3)
H150.05790.73260.87760.137*
C160.1923 (8)0.6681 (8)0.8810 (6)0.093 (2)
H160.14770.59980.89640.111*
C170.6887 (6)0.4775 (6)0.3940 (5)0.0690 (17)
H17A0.65320.47580.33200.083*
H17B0.77520.49350.39590.083*
C180.6255 (6)0.3591 (6)0.4070 (5)0.0700 (18)
H18A0.62770.29690.35380.084*
H18B0.66870.35650.46450.084*
C190.7840 (6)0.6380 (6)0.5480 (4)0.0681 (17)
H19A0.79540.57860.57420.082*
H19B0.76320.69100.59690.082*
C200.9051 (5)0.7107 (6)0.5289 (4)0.0619 (15)
C210.9161 (6)0.7821 (7)0.4713 (5)0.0765 (19)
H210.84500.78240.43970.092*
C221.0293 (7)0.8535 (7)0.4590 (6)0.088 (2)
H221.03330.90060.41930.105*
C231.1351 (7)0.8556 (8)0.5043 (6)0.094 (2)
H231.21130.90200.49450.113*
C241.1279 (7)0.7882 (8)0.5646 (6)0.095 (2)
H241.19940.79090.59810.115*
C251.0129 (6)0.7157 (7)0.5754 (5)0.082 (2)
H251.00900.66920.61560.098*
C260.4477 (7)0.2302 (5)0.4460 (5)0.0692 (17)
H26A0.36520.21950.45550.083*
H26B0.49790.24690.50730.083*
C270.4410 (9)0.1149 (6)0.3818 (6)0.088 (2)
C280.3607 (10)0.0594 (7)0.2950 (7)0.109 (3)
H280.31290.09560.27340.131*
C290.3520 (11)−0.0524 (8)0.2396 (7)0.119 (3)
H290.2956−0.09350.18200.142*
C300.4289 (10)−0.1003 (8)0.2721 (7)0.108 (3)
H300.4233−0.17430.23470.130*
C310.5115 (10)−0.0458 (8)0.3553 (7)0.108 (3)
H310.5633−0.07930.37520.130*
C320.5149 (9)0.0617 (7)0.4086 (6)0.102 (3)
H320.57070.10110.46660.122*
C330.8308 (18)0.4586 (19)0.8564 (15)0.111 (8)0.52 (2)
H330.79300.50320.83510.133*0.52 (2)
C340.945 (3)0.326 (3)0.814 (2)0.125 (8)0.52 (2)
H34A0.96470.33770.88130.187*0.52 (2)
H34B1.01980.34800.79070.187*0.52 (2)
H34C0.89300.24310.78190.187*0.52 (2)
C350.877 (2)0.425 (2)0.7071 (17)0.137 (9)0.52 (2)
H35A0.80740.36130.66120.206*0.52 (2)
H35B0.95130.43040.68530.206*0.52 (2)
H35C0.86800.49960.71530.206*0.52 (2)
C33'0.8850 (18)0.400 (2)0.8893 (16)0.109 (8)0.48 (2)
H33'0.92580.36050.91400.130*0.48 (2)
C34'0.803 (2)0.441 (2)0.7512 (16)0.119 (8)0.48 (2)
H34D0.72660.42070.77220.178*0.48 (2)
H34E0.78800.40380.68380.178*0.48 (2)
H34F0.84310.52680.76560.178*0.48 (2)
C35'0.946 (3)0.329 (3)0.751 (2)0.128 (9)0.48 (2)
H35D1.02490.35250.79030.193*0.48 (2)
H35E0.95590.34170.69120.193*0.48 (2)
H35F0.89740.24500.74110.193*0.48 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0397 (5)0.0367 (5)0.0311 (4)0.0144 (4)0.0077 (3)0.0110 (4)
Ni20.0429 (5)0.0381 (5)0.0319 (4)0.0171 (4)0.0097 (4)0.0107 (4)
Cl10.0708 (9)0.0528 (8)0.0422 (7)0.0125 (7)0.0107 (6)0.0183 (6)
Cl20.0868 (11)0.0541 (9)0.0448 (8)−0.0003 (8)0.0074 (7)0.0159 (6)
N10.050 (3)0.047 (3)0.047 (2)0.016 (2)0.013 (2)0.013 (2)
N20.059 (3)0.055 (3)0.051 (3)0.030 (2)0.012 (2)0.021 (2)
N30.046 (2)0.051 (3)0.048 (2)0.023 (2)0.015 (2)0.020 (2)
N40.054 (3)0.044 (2)0.044 (2)0.023 (2)0.015 (2)0.0112 (19)
N50.109 (6)0.158 (8)0.100 (6)0.083 (6)0.037 (5)0.038 (5)
O10.058 (2)0.052 (2)0.0403 (19)0.0182 (18)0.0159 (17)0.0158 (16)
O20.054 (2)0.051 (2)0.0382 (18)0.0191 (17)0.0113 (16)0.0163 (16)
O30.109 (5)0.151 (6)0.109 (5)0.064 (5)0.038 (4)0.039 (4)
C10.065 (4)0.050 (3)0.060 (3)0.020 (3)0.009 (3)0.018 (3)
C20.073 (4)0.062 (4)0.060 (4)0.040 (3)0.018 (3)0.018 (3)
C30.060 (4)0.068 (4)0.068 (4)0.019 (3)0.018 (3)0.017 (3)
C40.053 (3)0.056 (4)0.062 (4)0.012 (3)0.011 (3)0.023 (3)
C50.068 (4)0.075 (5)0.076 (4)0.008 (4)0.017 (4)0.020 (4)
C60.070 (5)0.078 (5)0.095 (6)−0.004 (4)0.018 (4)0.027 (4)
C70.067 (5)0.066 (5)0.092 (5)0.003 (4)−0.002 (4)0.022 (4)
C80.072 (4)0.063 (4)0.076 (5)0.010 (4)0.000 (4)0.016 (4)
C90.066 (4)0.063 (4)0.069 (4)0.006 (3)0.009 (3)0.021 (3)
C100.074 (4)0.069 (4)0.056 (3)0.041 (3)0.018 (3)0.028 (3)
C110.085 (5)0.084 (5)0.074 (4)0.052 (4)0.020 (4)0.034 (4)
C120.104 (6)0.082 (5)0.091 (5)0.048 (5)0.017 (4)0.037 (4)
C130.122 (8)0.096 (6)0.108 (7)0.049 (6)0.013 (6)0.044 (5)
C140.120 (8)0.104 (7)0.121 (7)0.063 (7)0.006 (6)0.035 (6)
C150.107 (7)0.118 (8)0.124 (8)0.061 (7)0.016 (6)0.027 (6)
C160.094 (6)0.096 (6)0.102 (6)0.053 (5)0.013 (5)0.035 (5)
C170.063 (4)0.068 (4)0.072 (4)0.025 (3)0.027 (3)0.013 (3)
C180.063 (4)0.063 (4)0.077 (4)0.029 (3)0.022 (3)0.003 (3)
C190.055 (4)0.082 (5)0.064 (4)0.019 (3)0.013 (3)0.032 (3)
C200.050 (3)0.075 (4)0.065 (4)0.026 (3)0.014 (3)0.028 (3)
C210.055 (4)0.090 (5)0.081 (5)0.019 (4)0.009 (3)0.038 (4)
C220.065 (5)0.098 (6)0.089 (5)0.014 (4)0.012 (4)0.043 (4)
C230.060 (5)0.109 (6)0.099 (6)0.013 (4)0.018 (4)0.037 (5)
C240.059 (5)0.111 (7)0.106 (6)0.024 (4)0.005 (4)0.037 (5)
C250.061 (4)0.093 (5)0.089 (5)0.023 (4)0.008 (4)0.040 (4)
C260.093 (5)0.048 (4)0.066 (4)0.029 (3)0.024 (4)0.014 (3)
C270.130 (7)0.059 (4)0.092 (5)0.058 (5)0.027 (5)0.018 (4)
C280.142 (8)0.073 (5)0.107 (7)0.051 (6)0.017 (6)0.012 (5)
C290.150 (9)0.080 (6)0.109 (7)0.043 (6)0.018 (6)0.010 (5)
C300.146 (9)0.069 (5)0.108 (7)0.053 (6)0.030 (6)0.010 (5)
C310.142 (8)0.072 (5)0.111 (7)0.054 (6)0.025 (6)0.015 (5)
C320.137 (8)0.067 (5)0.105 (6)0.053 (5)0.023 (6)0.018 (4)
C330.108 (14)0.147 (17)0.105 (16)0.078 (13)0.030 (12)0.041 (13)
C340.122 (17)0.16 (2)0.12 (2)0.083 (16)0.023 (17)0.045 (19)
C350.129 (19)0.17 (2)0.123 (18)0.079 (17)0.026 (14)0.037 (16)
C33'0.107 (15)0.148 (19)0.106 (16)0.085 (14)0.034 (12)0.041 (13)
C34'0.112 (17)0.148 (19)0.108 (17)0.066 (15)0.025 (13)0.039 (14)
C35'0.128 (19)0.16 (2)0.11 (2)0.081 (18)0.024 (18)0.037 (19)
Geometric parameters (Å, °) top
Ni1—O12.100 (3)C12—H120.9300
Ni1—N12.131 (4)C13—C141.350 (13)
Ni1—N22.143 (4)C13—H130.9300
Ni2—O22.111 (3)C14—C151.377 (13)
Ni2—N32.140 (4)C14—H140.9300
Ni2—N42.130 (4)C15—C161.405 (12)
N1—C31.458 (7)C15—H150.9300
N1—C11.499 (7)C16—H160.9300
N1—H10.9100C17—C181.476 (9)
N2—C21.465 (7)C17—H17A0.9700
N2—C101.469 (7)C17—H17B0.9700
N2—H20.9100C18—H18A0.9700
N3—C191.460 (7)C18—H18B0.9700
N3—C171.482 (7)C19—C201.497 (8)
N3—H30.9100C19—H19A0.9700
N4—C181.455 (7)C19—H19B0.9700
N4—C261.467 (7)C20—C251.371 (9)
N4—H40.9100C20—C211.373 (9)
N5—C331.32 (2)C21—C221.379 (9)
N5—C33'1.34 (2)C21—H210.9300
N5—C34'1.43 (2)C22—C231.359 (11)
N5—C341.44 (2)C22—H220.9300
N5—C35'1.47 (3)C23—C241.372 (11)
N5—C351.48 (2)C23—H230.9300
O1—H1C0.8500C24—C251.391 (10)
O1—H1D0.8500C24—H240.9300
O2—H2C0.8500C25—H250.9300
O2—H2D0.8500C26—C271.490 (9)
O3—C33'1.229 (19)C26—H26A0.9700
O3—C331.25 (2)C26—H26B0.9700
C1—C21.504 (8)C27—C321.372 (11)
C1—H1A0.9700C27—C281.374 (11)
C1—H1B0.9700C28—C291.398 (11)
C2—H2A0.9700C28—H280.9300
C2—H2B0.9700C29—C301.380 (13)
C3—C41.510 (8)C29—H290.9300
C3—H3A0.9700C30—C311.347 (12)
C3—H3B0.9700C30—H300.9300
C4—C51.372 (9)C31—C321.367 (10)
C4—C91.382 (9)C31—H310.9300
C5—C61.380 (10)C32—H320.9300
C5—H50.9300C33—H330.9300
C6—C71.363 (10)C34—H34A0.9600
C6—H60.9300C34—H34B0.9600
C7—C81.360 (10)C34—H34C0.9600
C7—H70.9300C35—H35A0.9600
C8—C91.384 (9)C35—H35B0.9600
C8—H80.9300C35—H35C0.9600
C9—H90.9300C33'—H33'0.9300
C10—C111.505 (8)C34'—H34D0.9600
C10—H10A0.9700C34'—H34E0.9600
C10—H10B0.9700C34'—H34F0.9600
C11—C161.375 (11)C35'—H35D0.9600
C11—C121.383 (10)C35'—H35E0.9600
C12—C131.381 (11)C35'—H35F0.9600
O1—Ni1—O1i180.000 (2)C8—C9—H9118.6
O1—Ni1—N1i88.91 (15)N2—C10—C11115.3 (5)
O1i—Ni1—N1i91.09 (15)N2—C10—H10A108.4
O1—Ni1—N191.09 (15)C11—C10—H10A108.4
O1i—Ni1—N188.91 (15)N2—C10—H10B108.4
N1i—Ni1—N1180.0 (2)C11—C10—H10B108.4
O1—Ni1—N2i84.86 (15)H10A—C10—H10B107.5
O1i—Ni1—N2i95.14 (15)C16—C11—C12118.1 (7)
N1i—Ni1—N2i83.75 (17)C16—C11—C10121.7 (7)
N1—Ni1—N2i96.25 (17)C12—C11—C10120.2 (7)
O1—Ni1—N295.14 (15)C13—C12—C11123.6 (8)
O1i—Ni1—N284.86 (15)C13—C12—H12118.2
N1i—Ni1—N296.25 (17)C11—C12—H12118.2
N1—Ni1—N283.75 (17)C14—C13—C12116.5 (9)
N2i—Ni1—N2180.0 (2)C14—C13—H13121.8
O2ii—Ni2—O2180.000 (1)C12—C13—H13121.8
O2ii—Ni2—N491.57 (15)C13—C14—C15123.2 (9)
O2—Ni2—N488.43 (15)C13—C14—H14118.4
O2ii—Ni2—N4ii88.43 (15)C15—C14—H14118.4
O2—Ni2—N4ii91.57 (15)C14—C15—C16118.8 (10)
N4—Ni2—N4ii180.000 (1)C14—C15—H15120.6
O2ii—Ni2—N390.50 (15)C16—C15—H15120.6
O2—Ni2—N389.50 (15)C11—C16—C15119.7 (9)
N4—Ni2—N383.51 (16)C11—C16—H16120.1
N4ii—Ni2—N396.49 (16)C15—C16—H16120.1
O2ii—Ni2—N3ii89.50 (15)C18—C17—N3112.2 (5)
O2—Ni2—N3ii90.50 (15)C18—C17—H17A109.2
N4—Ni2—N3ii96.49 (16)N3—C17—H17A109.2
N4ii—Ni2—N3ii83.51 (16)C18—C17—H17B109.2
N3—Ni2—N3ii180.000 (1)N3—C17—H17B109.2
C3—N1—C1111.2 (5)H17A—C17—H17B107.9
C3—N1—Ni1119.6 (4)N4—C18—C17111.3 (5)
C1—N1—Ni1105.4 (3)N4—C18—H18A109.4
C3—N1—H1106.6C17—C18—H18A109.4
C1—N1—H1106.6N4—C18—H18B109.4
Ni1—N1—H1106.6C17—C18—H18B109.4
C2—N2—C10113.5 (5)H18A—C18—H18B108.0
C2—N2—Ni1105.1 (3)N3—C19—C20117.5 (5)
C10—N2—Ni1117.4 (3)N3—C19—H19A107.9
C2—N2—H2106.8C20—C19—H19A107.9
C10—N2—H2106.8N3—C19—H19B107.9
Ni1—N2—H2106.8C20—C19—H19B107.9
C19—N3—C17114.1 (5)H19A—C19—H19B107.2
C19—N3—Ni2117.3 (3)C25—C20—C21116.5 (6)
C17—N3—Ni2105.8 (3)C25—C20—C19120.1 (6)
C19—N3—H3106.3C21—C20—C19123.1 (6)
C17—N3—H3106.3C20—C21—C22122.0 (7)
Ni2—N3—H3106.3C20—C21—H21119.0
C18—N4—C26108.8 (5)C22—C21—H21119.0
C18—N4—Ni2106.0 (3)C23—C22—C21120.6 (7)
C26—N4—Ni2117.2 (3)C23—C22—H22119.7
C18—N4—H4108.2C21—C22—H22119.7
C26—N4—H4108.2C22—C23—C24119.0 (7)
Ni2—N4—H4108.2C22—C23—H23120.5
C33—N5—C33'57.9 (12)C24—C23—H23120.5
C33—N5—C34'66.3 (13)C23—C24—C25119.7 (7)
C33'—N5—C34'123.1 (14)C23—C24—H24120.2
C33—N5—C34130.7 (16)C25—C24—H24120.2
C33'—N5—C3472.8 (14)C20—C25—C24122.1 (7)
C34'—N5—C34159.6 (16)C20—C25—H25118.9
C33—N5—C35'168.7 (17)C24—C25—H25118.9
C33'—N5—C35'110.8 (15)N4—C26—C27116.2 (5)
C34'—N5—C35'124.7 (16)N4—C26—H26A108.2
C33—N5—C35111.0 (15)C27—C26—H26A108.2
C33'—N5—C35167.6 (15)N4—C26—H26B108.2
C34'—N5—C3547.9 (11)C27—C26—H26B108.2
C34—N5—C35118.2 (14)H26A—C26—H26B107.4
C35'—N5—C3580.2 (14)C32—C27—C28118.7 (7)
Ni1—O1—H1C110.9C32—C27—C26120.4 (8)
Ni1—O1—H1D111.1C28—C27—C26121.0 (7)
H1C—O1—H1D109.1C27—C28—C29119.0 (9)
Ni2—O2—H2C107.3C27—C28—H28120.5
Ni2—O2—H2D109.3C29—C28—H28120.5
H2C—O2—H2D107.9C30—C29—C28118.6 (10)
C33'—O3—C3362.6 (13)C30—C29—H29120.7
N1—C1—C2109.0 (5)C28—C29—H29120.7
N1—C1—H1A109.9C31—C30—C29123.5 (8)
C2—C1—H1A109.9C31—C30—H30118.2
N1—C1—H1B109.9C29—C30—H30118.2
C2—C1—H1B109.9C30—C31—C32116.1 (9)
H1A—C1—H1B108.3C30—C31—H31121.9
N2—C2—C1110.0 (5)C32—C31—H31121.9
N2—C2—H2A109.7C31—C32—C27123.9 (9)
C1—C2—H2A109.7C31—C32—H32118.0
N2—C2—H2B109.7C27—C32—H32118.0
C1—C2—H2B109.7O3—C33—N5119.8 (17)
H2A—C2—H2B108.2O3—C33—H33120.1
N1—C3—C4115.1 (5)N5—C33—H33120.1
N1—C3—H3A108.5N5—C34—H34A109.5
C4—C3—H3A108.5N5—C34—H34B109.5
N1—C3—H3B108.5N5—C34—H34C109.5
C4—C3—H3B108.5N5—C35—H35A109.5
H3A—C3—H3B107.5N5—C35—H35B109.5
C5—C4—C9116.4 (6)N5—C35—H35C109.5
C5—C4—C3121.3 (6)O3—C33'—N5119.7 (17)
C9—C4—C3122.4 (5)O3—C33'—H33'120.2
C4—C5—C6121.7 (7)N5—C33'—H33'120.2
C4—C5—H5119.1N5—C34'—H34D109.5
C6—C5—H5119.1N5—C34'—H34E109.5
C7—C6—C5120.2 (7)H34D—C34'—H34E109.5
C7—C6—H6119.9N5—C34'—H34F109.5
C5—C6—H6119.9H34D—C34'—H34F109.5
C8—C7—C6120.2 (7)H34E—C34'—H34F109.5
C8—C7—H7119.9N5—C35'—H35D109.5
C6—C7—H7119.9N5—C35'—H35E109.5
C7—C8—C9118.7 (7)H35D—C35'—H35E109.5
C7—C8—H8120.6N5—C35'—H35F109.5
C9—C8—H8120.6H35D—C35'—H35F109.5
C4—C9—C8122.8 (6)H35E—C35'—H35F109.5
C4—C9—H9118.6
O1—Ni1—N1—C3−44.8 (4)N2—C10—C11—C16−69.1 (9)
O1i—Ni1—N1—C3135.2 (4)N2—C10—C11—C12109.3 (7)
N2i—Ni1—N1—C340.2 (4)C16—C11—C12—C13−0.1 (12)
N2—Ni1—N1—C3−139.8 (4)C10—C11—C12—C13−178.5 (7)
O1—Ni1—N1—C181.3 (3)C11—C12—C13—C140.6 (13)
O1i—Ni1—N1—C1−98.7 (3)C12—C13—C14—C15−1.8 (15)
N2i—Ni1—N1—C1166.2 (3)C13—C14—C15—C162.5 (16)
N2—Ni1—N1—C1−13.8 (3)C12—C11—C16—C150.7 (12)
O1—Ni1—N2—C2−106.3 (3)C10—C11—C16—C15179.2 (7)
O1i—Ni1—N2—C273.7 (3)C14—C15—C16—C11−1.9 (14)
N1i—Ni1—N2—C2164.2 (3)C19—N3—C17—C1895.7 (6)
N1—Ni1—N2—C2−15.8 (3)Ni2—N3—C17—C18−34.8 (6)
O1—Ni1—N2—C1020.8 (4)C26—N4—C18—C17−168.3 (5)
O1i—Ni1—N2—C10−159.2 (4)Ni2—N4—C18—C17−41.5 (6)
N1i—Ni1—N2—C10−68.6 (4)N3—C17—C18—N453.6 (7)
N1—Ni1—N2—C10111.4 (4)C17—N3—C19—C2066.8 (7)
O2ii—Ni2—N3—C19149.0 (4)Ni2—N3—C19—C20−168.6 (4)
O2—Ni2—N3—C19−31.0 (4)N3—C19—C20—C25−143.9 (7)
N4—Ni2—N3—C19−119.5 (4)N3—C19—C20—C2141.4 (10)
N4ii—Ni2—N3—C1960.5 (4)C25—C20—C21—C221.4 (11)
O2ii—Ni2—N3—C17−82.4 (4)C19—C20—C21—C22176.3 (7)
O2—Ni2—N3—C1797.6 (4)C20—C21—C22—C23−0.2 (13)
N4—Ni2—N3—C179.1 (4)C21—C22—C23—C24−1.8 (13)
N4ii—Ni2—N3—C17−170.9 (4)C22—C23—C24—C252.5 (13)
O2ii—Ni2—N4—C18107.4 (4)C21—C20—C25—C24−0.7 (11)
O2—Ni2—N4—C18−72.6 (4)C19—C20—C25—C24−175.7 (7)
N3—Ni2—N4—C1817.1 (4)C23—C24—C25—C20−1.2 (13)
N3ii—Ni2—N4—C18−162.9 (4)C18—N4—C26—C27−63.0 (8)
O2ii—Ni2—N4—C26−131.0 (4)Ni2—N4—C26—C27176.8 (5)
O2—Ni2—N4—C2649.0 (4)N4—C26—C27—C32112.1 (9)
N3—Ni2—N4—C26138.7 (4)N4—C26—C27—C28−68.1 (11)
N3ii—Ni2—N4—C26−41.3 (4)C32—C27—C28—C293.7 (14)
C3—N1—C1—C2172.3 (5)C26—C27—C28—C29−176.1 (8)
Ni1—N1—C1—C241.3 (5)C27—C28—C29—C30−3.1 (15)
C10—N2—C2—C1−85.9 (6)C28—C29—C30—C310.7 (16)
Ni1—N2—C2—C143.6 (5)C29—C30—C31—C321.1 (16)
N1—C1—C2—N2−59.5 (6)C30—C31—C32—C27−0.5 (15)
C1—N1—C3—C455.2 (7)C28—C27—C32—C31−1.9 (15)
Ni1—N1—C3—C4178.4 (4)C26—C27—C32—C31177.8 (8)
N1—C3—C4—C5−133.1 (7)C33'—O3—C33—N51.8 (17)
N1—C3—C4—C948.3 (9)C33'—N5—C33—O3−1.7 (16)
C9—C4—C5—C6−0.4 (11)C34'—N5—C33—O3166 (2)
C3—C4—C5—C6−179.1 (7)C34—N5—C33—O30(3)
C4—C5—C6—C7−1.3 (13)C35'—N5—C33—O3−3(10)
C5—C6—C7—C81.7 (13)C35—N5—C33—O3−175.5 (17)
C6—C7—C8—C9−0.3 (12)C33—O3—C33'—N5−1.8 (17)
C5—C4—C9—C81.9 (10)C33—N5—C33'—O31.7 (17)
C3—C4—C9—C8−179.4 (6)C34'—N5—C33'—O3−11 (3)
C7—C8—C9—C4−1.5 (11)C34—N5—C33'—O3−177 (2)
C2—N2—C10—C11−53.8 (7)C35'—N5—C33'—O3−179 (2)
Ni1—N2—C10—C11−176.8 (5)C35—N5—C33'—O330 (8)
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···Cl20.852.263.055 (4)155
O1—H1D···Cl1ii0.852.243.078 (4)169
O2—H2C···Cl1ii0.852.243.071 (4)168
O2—H2D···Cl20.852.193.041 (4)174
N1—H1···Cl1iii0.912.543.444 (4)171
N2—H2···O3i0.912.203.102 (8)169
N3—H3···Cl10.912.553.400 (4)155
N4—H4···Cl2ii0.912.543.428 (5)167
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x, y, z+1; (i) −x+1, −y+1, −z+2.
Table 1
Selected geometric parameters (Å) top
Ni1—O12.100 (3)Ni2—O22.111 (3)
Ni1—N12.131 (4)Ni2—N32.140 (4)
Ni1—N22.143 (4)Ni2—N42.130 (4)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···Cl20.852.263.055 (4)155
O1—H1D···Cl1i0.852.243.078 (4)169
O2—H2C···Cl1i0.852.243.071 (4)168
O2—H2D···Cl20.852.193.041 (4)174
N1—H1···Cl1ii0.912.543.444 (4)171
N2—H2···O3iii0.912.203.102 (8)169
N3—H3···Cl10.912.553.400 (4)155
N4—H4···Cl2i0.912.543.428 (5)167
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) −x+1, −y+1, −z+2.
Acknowledgements top

We acknowledge financial support by the Science Foundation of Huaihai Institute of Technology and the Department of Chemical Engineering.

references
References top

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Yang, S.-P. (2007a). Acta Cryst. E63, m1162–m1164.

Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Yang, S.-P. (2007b). Acta Cryst. E63, m2512–m2513.