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Acta Cryst. (2008). E64, m836    [ doi:10.1107/S1600536808015183 ]

Di-[mu]-chlorido-bis{chlorido[2-(2-furylmethyliminomethyl)pyridine-[kappa]2N,N']nickel(II)}

D.-S. Xia, W. Chen, X.-L. Tang and Q.-F. Zeng

Abstract top

The title dinuclear nickel(II) complex, [Ni2Cl4(C11H10N2O)2], lies on a centre of symmetry located at the centroid of the four-membered ring formed by the two Ni atoms and the bridging chloride ions. The NiII atom is five-coordinated in a square-pyramidal geometry by the imine and pyridine N atoms of the Schiff base ligand, and by one terminal and two bridging Cl atoms. The Ni...Ni distance is 3.506 (2) Å. The O atom of the furan substituent in the ligand unit is not involved in coordination to the Ni atom.

Comment top

As part of our ongoing interest in the structure of nickel(II) complexes (Zhu et al., 2003), we report herein the crystal structure of the title compound, a new centrosymmetric dinuclear nickel(II) complex, (I), Fig. 1, derived from the Schiff base ligand furan-2-ylmethyl-(1-pyridin-2-ylmethylidene)amine.

The NiII atom in (I) is five-coordinate in a square pyramidal geometry, binding to the imine and pyridine N atoms of the Schiff base ligand, and to one terminal Cl and two bridging Cl atoms. The Ni···Ni distance is 3.506 (2) Å. The dihedral angle between the benzene ring and the furan ring is 73.3 (3) °. The O atom of the furan substituent in the ligand lies well away from the coordination sphere of the Ni atom. The coordinate bond values (Table 1) are comparable to values observed in other similar nickel(II) complexes (Shi et al., 2007; Li et al., 2007; Cheng et al., 2007; Qiu et al., 2006; Wang et al., 2005).

Related literature top

For related structures, see: Cheng et al. (2007); Li et al. (2007); Qiu et al. (2006); Shi et al. (2007); Wang et al. (2005); Zhu et al. (2003).

Experimental top

Pyridine-2-carbaldehyde (10.7 mg, 0.1 mmol), furan-2-ylmethylamine (9.7 mg, 0.1 mmol), and NiCl2.6H2O (23.8 mg, 0.1 mmol) were dissolved in methanol (30 ml). The mixture was stirred for 30 min at room temperature. The resulting solution was left in air for a few days, yielding green crystals.

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, and with Uiso(H) set at 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme. Numbered atoms are related to un-numbered atoms by the symmetry code 1-x, 2-y, 1-z.
Di-µ-chlorido-bis{chlorido[2-(2-furylmethyliminomethyl)pyridine- κ2N,N']nickel(II)} top
Crystal data top
[Ni2Cl4(C11H10N2O)2]Z = 1
Mr = 631.64F000 = 320
Triclinic, P1Dx = 1.704 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 8.0439 (8) ÅCell parameters from 1237 reflections
b = 8.5659 (8) Åθ = 2.4–25.3º
c = 10.0610 (9) ŵ = 1.99 mm−1
α = 77.522 (8)ºT = 298 (2) K
β = 72.040 (7)ºBlock, green
γ = 70.132 (8)º0.30 × 0.30 × 0.28 mm
V = 615.39 (10) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer		2408 independent reflections
Radiation source: fine-focus sealed tube1971 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.020
T = 298(2) Kθmax = 26.0º
ω scansθmin = 2.6º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = 0→9
Tmin = 0.554, Tmax = 0.572k = −9→10
2585 measured reflectionsl = −11→12
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)] = 0.040H-atom parameters constrained
wR(F2) = 0.099  w = 1/[σ2(Fo2) + (0.0486P)2 + 0.2142P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2408 reflectionsΔρmax = 0.51 e Å−3
154 parametersΔρmin = −0.58 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ni2Cl4(C11H10N2O)2]γ = 70.132 (8)º
Mr = 631.64V = 615.39 (10) Å3
Triclinic, P1Z = 1
a = 8.0439 (8) ÅMo Kα
b = 8.5659 (8) ŵ = 1.99 mm−1
c = 10.0610 (9) ÅT = 298 (2) K
α = 77.522 (8)º0.30 × 0.30 × 0.28 mm
β = 72.040 (7)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		2408 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1971 reflections with I > 2σ(I)
Tmin = 0.554, Tmax = 0.572Rint = 0.020
2585 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040154 parameters
wR(F2) = 0.099H-atom parameters constrained
S = 1.07Δρmax = 0.51 e Å−3
2408 reflectionsΔρmin = −0.58 e Å−3
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 > 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 (Å2) top
xyzUiso*/Ueq
Ni10.72650 (5)1.00555 (5)0.45738 (4)0.03767 (16)
Cl10.46003 (12)1.19011 (10)0.55654 (10)0.0481 (2)
Cl20.76194 (14)1.16826 (13)0.24879 (11)0.0608 (3)
O10.6666 (5)0.6517 (4)0.9351 (3)0.0729 (9)
N10.9716 (4)0.8340 (4)0.3931 (3)0.0444 (7)
C110.7243 (7)0.5754 (6)1.0541 (5)0.0848 (16)
H110.72560.46701.09550.102*
N30.7676 (4)0.8807 (3)0.6475 (3)0.0418 (7)
C11.0714 (5)0.8105 (5)0.2615 (4)0.0576 (10)
H11.03130.88370.18710.069*
C21.2312 (6)0.6821 (5)0.2320 (5)0.0617 (11)
H21.29620.66830.13920.074*
C31.2941 (5)0.5746 (5)0.3406 (5)0.0608 (11)
H31.40160.48700.32270.073*
C41.1937 (5)0.5998 (5)0.4771 (4)0.0533 (10)
H41.23430.53050.55280.064*
C51.0333 (5)0.7283 (4)0.4998 (4)0.0429 (8)
C60.9147 (4)0.7611 (4)0.6387 (4)0.0428 (8)
H60.94580.69600.71930.051*
C70.6364 (5)0.9170 (5)0.7850 (4)0.0477 (9)
H7A0.61911.03150.79660.057*
H7B0.51960.90990.78270.057*
C80.6882 (5)0.8072 (5)0.9094 (4)0.0479 (9)
C90.7552 (6)0.8277 (6)1.0092 (4)0.0658 (11)
H90.78150.92281.01600.079*
C100.7779 (7)0.6769 (7)1.1019 (5)0.0820 (16)
H100.82230.65371.18130.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0292 (2)0.0323 (2)0.0470 (3)−0.00427 (17)−0.01482 (18)0.00379 (17)
Cl10.0407 (5)0.0327 (4)0.0685 (6)−0.0016 (4)−0.0209 (4)−0.0061 (4)
Cl20.0525 (6)0.0567 (6)0.0665 (6)−0.0179 (5)−0.0227 (5)0.0201 (5)
O10.094 (2)0.0557 (18)0.0644 (19)−0.0237 (17)−0.0199 (17)0.0038 (14)
N10.0373 (16)0.0441 (16)0.0497 (17)−0.0115 (13)−0.0144 (13)0.0024 (13)
C110.093 (4)0.062 (3)0.058 (3)0.002 (3)−0.005 (3)0.015 (2)
N30.0380 (15)0.0382 (15)0.0498 (17)−0.0091 (13)−0.0171 (13)−0.0013 (13)
C10.052 (2)0.061 (2)0.052 (2)−0.010 (2)−0.0134 (19)0.0004 (19)
C20.050 (2)0.063 (3)0.062 (3)−0.011 (2)0.000 (2)−0.017 (2)
C30.044 (2)0.048 (2)0.078 (3)−0.0007 (18)−0.012 (2)−0.010 (2)
C40.041 (2)0.043 (2)0.067 (3)−0.0028 (16)−0.0165 (19)−0.0015 (18)
C50.0357 (18)0.0364 (18)0.055 (2)−0.0091 (14)−0.0146 (16)−0.0008 (15)
C60.0351 (18)0.0396 (18)0.052 (2)−0.0077 (15)−0.0197 (16)0.0043 (15)
C70.0371 (19)0.045 (2)0.054 (2)−0.0053 (16)−0.0105 (16)−0.0041 (16)
C80.042 (2)0.045 (2)0.048 (2)−0.0045 (16)−0.0093 (16)−0.0051 (16)
C90.066 (3)0.076 (3)0.054 (2)−0.019 (2)−0.016 (2)−0.009 (2)
C100.074 (3)0.099 (4)0.049 (3)0.000 (3)−0.019 (2)0.004 (3)
Geometric parameters (Å, °) top
Ni1—N12.030 (3)C2—C31.374 (6)
Ni1—N32.044 (3)C2—H20.9300
Ni1—Cl22.2506 (10)C3—C41.382 (5)
Ni1—Cl12.2690 (10)C3—H30.9300
Ni1—Cl1i2.6496 (10)C4—C51.375 (5)
Cl1—Ni1i2.6496 (10)C4—H40.9300
O1—C81.361 (5)C5—C61.452 (5)
O1—C111.369 (5)C6—H60.9300
N1—C11.337 (5)C7—C81.473 (5)
N1—C51.350 (4)C7—H7A0.9700
C11—C101.317 (7)C7—H7B0.9700
C11—H110.9300C8—C91.343 (5)
N3—C61.268 (4)C9—C101.412 (6)
N3—C71.479 (4)C9—H90.9300
C1—C21.377 (5)C10—H100.9300
C1—H10.9300
N1—Ni1—N379.68 (11)C2—C3—C4118.4 (4)
N1—Ni1—Cl292.50 (9)C2—C3—H3120.8
N3—Ni1—Cl2160.74 (8)C4—C3—H3120.8
N1—Ni1—Cl1172.70 (9)C5—C4—C3119.3 (4)
N3—Ni1—Cl193.38 (8)C5—C4—H4120.4
Cl2—Ni1—Cl193.42 (4)C3—C4—H4120.4
N1—Ni1—Cl1i93.04 (8)N1—C5—C4122.3 (3)
N3—Ni1—Cl1i91.84 (8)N1—C5—C6114.2 (3)
Cl2—Ni1—Cl1i106.23 (4)C4—C5—C6123.5 (3)
Cl1—Ni1—Cl1i89.40 (3)N3—C6—C5118.3 (3)
Ni1—Cl1—Ni1i90.60 (3)N3—C6—H6120.8
C8—O1—C11106.2 (4)C5—C6—H6120.8
C1—N1—C5118.0 (3)C8—C7—N3116.0 (3)
C1—N1—Ni1128.3 (3)C8—C7—H7A108.3
C5—N1—Ni1113.7 (2)N3—C7—H7A108.3
C10—C11—O1110.6 (4)C8—C7—H7B108.3
C10—C11—H11124.7N3—C7—H7B108.3
O1—C11—H11124.7H7A—C7—H7B107.4
C6—N3—C7121.3 (3)C9—C8—O1109.5 (4)
C6—N3—Ni1114.1 (2)C9—C8—C7133.0 (4)
C7—N3—Ni1124.5 (2)O1—C8—C7117.5 (3)
N1—C1—C2122.4 (4)C8—C9—C10106.9 (5)
N1—C1—H1118.8C8—C9—H9126.6
C2—C1—H1118.8C10—C9—H9126.6
C3—C2—C1119.6 (4)C11—C10—C9106.8 (4)
C3—C2—H2120.2C11—C10—H10126.6
C1—C2—H2120.2C9—C10—H10126.6
N1—Ni1—Cl1—Ni1i−109.6 (7)N1—C1—C2—C3−1.1 (7)
N3—Ni1—Cl1—Ni1i−91.81 (8)C1—C2—C3—C4−0.2 (6)
Cl2—Ni1—Cl1—Ni1i106.22 (4)C2—C3—C4—C51.4 (6)
Cl1i—Ni1—Cl1—Ni1i0.0C1—N1—C5—C40.2 (5)
N3—Ni1—N1—C1178.4 (3)Ni1—N1—C5—C4177.7 (3)
Cl2—Ni1—N1—C1−19.4 (3)C1—N1—C5—C6−178.9 (3)
Cl1—Ni1—N1—C1−163.6 (5)Ni1—N1—C5—C6−1.4 (4)
Cl1i—Ni1—N1—C187.0 (3)C3—C4—C5—N1−1.5 (6)
N3—Ni1—N1—C51.3 (2)C3—C4—C5—C6177.5 (4)
Cl2—Ni1—N1—C5163.5 (2)C7—N3—C6—C5177.4 (3)
Cl1—Ni1—N1—C519.3 (8)Ni1—N3—C6—C50.4 (4)
Cl1i—Ni1—N1—C5−90.1 (2)N1—C5—C6—N30.7 (5)
C8—O1—C11—C100.5 (5)C4—C5—C6—N3−178.4 (3)
N1—Ni1—N3—C6−0.9 (2)C6—N3—C7—C80.5 (5)
Cl2—Ni1—N3—C6−68.1 (4)Ni1—N3—C7—C8177.2 (2)
Cl1—Ni1—N3—C6−178.6 (2)C11—O1—C8—C9−0.6 (5)
Cl1i—Ni1—N3—C691.9 (2)C11—O1—C8—C7179.7 (3)
N1—Ni1—N3—C7−177.8 (3)N3—C7—C8—C9103.2 (5)
Cl2—Ni1—N3—C7114.9 (3)N3—C7—C8—O1−77.1 (4)
Cl1—Ni1—N3—C74.4 (3)O1—C8—C9—C100.4 (5)
Cl1i—Ni1—N3—C7−85.1 (3)C7—C8—C9—C10−179.9 (4)
C5—N1—C1—C21.0 (6)O1—C11—C10—C9−0.3 (6)
Ni1—N1—C1—C2−175.9 (3)C8—C9—C10—C11−0.1 (6)
Symmetry codes: (i) −x+1, −y+2, −z+1.
Acknowledgements top

The authors appreciate the generous financial support of this work by the Chinese Funds for the Zhicheng Project (2006BAC02A11) and the Wuhan Yindao project (20066009138-07).

references
References top

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Cheng, K., You, Z.-L. & Zhu, H.-L. (2007). Aust. J. Chem. 60, 375–379.

Li, Y.-G., Shi, D.-H., Zhu, H.-L., Yan, H. & Ng, S. W. (2007). Inorg. Chim. Acta, 360, 2881–2889.

Qiu, X.-Y., Ma, J.-L., Liu, W.-S. & Zhu, H.-L. (2006). Acta Cryst. E62, m1289–m1290.

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

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

Shi, D.-H., You, Z.-L., Xu, C., Zhang, Q. & Zhu, H.-L. (2007). Inorg. Chem. Commun. 10, 404–406.

Wang, S.-F., Xue, J.-Y., Shi, L., Zhu, H.-L. & Ng, S. W. (2005). Acta Cryst. E61, m1481–m1483.

Zhu, H.-L., Zeng, Q.-F., Xia, D.-S., Liu, X.-Y. & Wang, D.-Q. (2003). Acta Cryst. E59, m777–m779.