Di-μ-chlorido-bis­{chlorido[2-(2-furyl­methyl­imino­meth­yl)pyridine-κ2N,N′]nickel(II)}

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

doi:10.1107/S1600536808015183

metal-organic compounds

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Volume 64| Part 6| June 2008| Page m836

doi:10.1107/S1600536808015183

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Di-μ-chlorido-bis{chlorido[2-(2-furylmethyliminomethyl)pyridine-κ²N,N′]nickel(II)}

Dong-Sheng Xia,^a Wu Chen,^a Xin-Long Tang ^a and Qing-Fu Zeng ^a ^*

^aEngineering Research Center for Clean Production of Textile Printing, Ministry of Education, Wuhan University of Science & Engineering, Wuhan 430073, People's Republic of China
^*Correspondence e-mail: qingfu_zeng@163.com

(Received 19 May 2008; accepted 20 May 2008; online 24 May 2008)

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 Ni^II 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.

Related literature

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

Crystal data

[Ni₂Cl₄(C₁₁H₁₀N₂O)₂]
M_r = 631.64
Triclinic, $[P \overline 1]$
a = 8.0439 (8) Å
b = 8.5659 (8) Å
c = 10.0610 (9) Å
α = 77.522 (8)°
β = 72.040 (7)°
γ = 70.132 (8)°
V = 615.39 (10) Å³
Z = 1
Mo Kα radiation
μ = 1.99 mm⁻¹
T = 298 (2) K
0.30 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.554, T_max = 0.572
2585 measured reflections
2408 independent reflections
1971 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.099
S = 1.07
2408 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015183/sj2503sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015183/sj2503Isup2.hkl

checkCIF report

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 Ni^II 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.

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

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
M_r = 631.64	F(000) = 320
Triclinic, P1	D_x = 1.704 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0439 (8) Å	Cell parameters from 1237 reflections
b = 8.5659 (8) Å	θ = 2.4–25.3°
c = 10.0610 (9) Å	µ = 1.99 mm⁻¹
α = 77.522 (8)°	T = 298 K
β = 72.040 (7)°	Block, green
γ = 70.132 (8)°	0.30 × 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 tube	1971 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 26.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = 0→9
T_min = 0.554, T_max = 0.572	k = −9→10
2585 measured reflections	l = −11→12

Refinement top

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0486P)² + 0.2142P] where P = (F_o² + 2F_c²)/3
2408 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

[Ni₂Cl₄(C₁₁H₁₀N₂O)₂]	γ = 70.132 (8)°
M_r = 631.64	V = 615.39 (10) Å³
Triclinic, P1	Z = 1
a = 8.0439 (8) Å	Mo Kα radiation
b = 8.5659 (8) Å	µ = 1.99 mm⁻¹
c = 10.0610 (9) Å	T = 298 K
α = 77.522 (8)°	0.30 × 0.30 × 0.28 mm
β = 72.040 (7)°

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)
T_min = 0.554, T_max = 0.572	R_int = 0.020
2585 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.07	Δρ_max = 0.51 e Å⁻³
2408 reflections	Δρ_min = −0.58 e Å⁻³
154 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 > 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

	x	y	z	U_iso*/U_eq
Ni1	0.72650 (5)	1.00555 (5)	0.45738 (4)	0.03767 (16)
Cl1	0.46003 (12)	1.19011 (10)	0.55654 (10)	0.0481 (2)
Cl2	0.76194 (14)	1.16826 (13)	0.24879 (11)	0.0608 (3)
O1	0.6666 (5)	0.6517 (4)	0.9351 (3)	0.0729 (9)
N1	0.9716 (4)	0.8340 (4)	0.3931 (3)	0.0444 (7)
C11	0.7243 (7)	0.5754 (6)	1.0541 (5)	0.0848 (16)
H11	0.7256	0.4670	1.0955	0.102*
N3	0.7676 (4)	0.8807 (3)	0.6475 (3)	0.0418 (7)
C1	1.0714 (5)	0.8105 (5)	0.2615 (4)	0.0576 (10)
H1	1.0313	0.8837	0.1871	0.069*
C2	1.2312 (6)	0.6821 (5)	0.2320 (5)	0.0617 (11)
H2	1.2962	0.6683	0.1392	0.074*
C3	1.2941 (5)	0.5746 (5)	0.3406 (5)	0.0608 (11)
H3	1.4016	0.4870	0.3227	0.073*
C4	1.1937 (5)	0.5998 (5)	0.4771 (4)	0.0533 (10)
H4	1.2343	0.5305	0.5528	0.064*
C5	1.0333 (5)	0.7283 (4)	0.4998 (4)	0.0429 (8)
C6	0.9147 (4)	0.7611 (4)	0.6387 (4)	0.0428 (8)
H6	0.9458	0.6960	0.7193	0.051*
C7	0.6364 (5)	0.9170 (5)	0.7850 (4)	0.0477 (9)
H7A	0.6191	1.0315	0.7966	0.057*
H7B	0.5196	0.9099	0.7827	0.057*
C8	0.6882 (5)	0.8072 (5)	0.9094 (4)	0.0479 (9)
C9	0.7552 (6)	0.8277 (6)	1.0092 (4)	0.0658 (11)
H9	0.7815	0.9228	1.0160	0.079*
C10	0.7779 (7)	0.6769 (7)	1.1019 (5)	0.0820 (16)
H10	0.8223	0.6537	1.1813	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0292 (2)	0.0323 (2)	0.0470 (3)	−0.00427 (17)	−0.01482 (18)	0.00379 (17)
Cl1	0.0407 (5)	0.0327 (4)	0.0685 (6)	−0.0016 (4)	−0.0209 (4)	−0.0061 (4)
Cl2	0.0525 (6)	0.0567 (6)	0.0665 (6)	−0.0179 (5)	−0.0227 (5)	0.0201 (5)
O1	0.094 (2)	0.0557 (18)	0.0644 (19)	−0.0237 (17)	−0.0199 (17)	0.0038 (14)
N1	0.0373 (16)	0.0441 (16)	0.0497 (17)	−0.0115 (13)	−0.0144 (13)	0.0024 (13)
C11	0.093 (4)	0.062 (3)	0.058 (3)	0.002 (3)	−0.005 (3)	0.015 (2)
N3	0.0380 (15)	0.0382 (15)	0.0498 (17)	−0.0091 (13)	−0.0171 (13)	−0.0013 (13)
C1	0.052 (2)	0.061 (2)	0.052 (2)	−0.010 (2)	−0.0134 (19)	0.0004 (19)
C2	0.050 (2)	0.063 (3)	0.062 (3)	−0.011 (2)	0.000 (2)	−0.017 (2)
C3	0.044 (2)	0.048 (2)	0.078 (3)	−0.0007 (18)	−0.012 (2)	−0.010 (2)
C4	0.041 (2)	0.043 (2)	0.067 (3)	−0.0028 (16)	−0.0165 (19)	−0.0015 (18)
C5	0.0357 (18)	0.0364 (18)	0.055 (2)	−0.0091 (14)	−0.0146 (16)	−0.0008 (15)
C6	0.0351 (18)	0.0396 (18)	0.052 (2)	−0.0077 (15)	−0.0197 (16)	0.0043 (15)
C7	0.0371 (19)	0.045 (2)	0.054 (2)	−0.0053 (16)	−0.0105 (16)	−0.0041 (16)
C8	0.042 (2)	0.045 (2)	0.048 (2)	−0.0045 (16)	−0.0093 (16)	−0.0051 (16)
C9	0.066 (3)	0.076 (3)	0.054 (2)	−0.019 (2)	−0.016 (2)	−0.009 (2)
C10	0.074 (3)	0.099 (4)	0.049 (3)	0.000 (3)	−0.019 (2)	0.004 (3)

Geometric parameters (Å, º) top

Ni1—N1	2.030 (3)	C2—C3	1.374 (6)
Ni1—N3	2.044 (3)	C2—H2	0.9300
Ni1—Cl2	2.2506 (10)	C3—C4	1.382 (5)
Ni1—Cl1	2.2690 (10)	C3—H3	0.9300
Ni1—Cl1ⁱ	2.6496 (10)	C4—C5	1.375 (5)
Cl1—Ni1ⁱ	2.6496 (10)	C4—H4	0.9300
O1—C8	1.361 (5)	C5—C6	1.452 (5)
O1—C11	1.369 (5)	C6—H6	0.9300
N1—C1	1.337 (5)	C7—C8	1.473 (5)
N1—C5	1.350 (4)	C7—H7A	0.9700
C11—C10	1.317 (7)	C7—H7B	0.9700
C11—H11	0.9300	C8—C9	1.343 (5)
N3—C6	1.268 (4)	C9—C10	1.412 (6)
N3—C7	1.479 (4)	C9—H9	0.9300
C1—C2	1.377 (5)	C10—H10	0.9300
C1—H1	0.9300

N1—Ni1—N3	79.68 (11)	C2—C3—C4	118.4 (4)
N1—Ni1—Cl2	92.50 (9)	C2—C3—H3	120.8
N3—Ni1—Cl2	160.74 (8)	C4—C3—H3	120.8
N1—Ni1—Cl1	172.70 (9)	C5—C4—C3	119.3 (4)
N3—Ni1—Cl1	93.38 (8)	C5—C4—H4	120.4
Cl2—Ni1—Cl1	93.42 (4)	C3—C4—H4	120.4
N1—Ni1—Cl1ⁱ	93.04 (8)	N1—C5—C4	122.3 (3)
N3—Ni1—Cl1ⁱ	91.84 (8)	N1—C5—C6	114.2 (3)
Cl2—Ni1—Cl1ⁱ	106.23 (4)	C4—C5—C6	123.5 (3)
Cl1—Ni1—Cl1ⁱ	89.40 (3)	N3—C6—C5	118.3 (3)
Ni1—Cl1—Ni1ⁱ	90.60 (3)	N3—C6—H6	120.8
C8—O1—C11	106.2 (4)	C5—C6—H6	120.8
C1—N1—C5	118.0 (3)	C8—C7—N3	116.0 (3)
C1—N1—Ni1	128.3 (3)	C8—C7—H7A	108.3
C5—N1—Ni1	113.7 (2)	N3—C7—H7A	108.3
C10—C11—O1	110.6 (4)	C8—C7—H7B	108.3
C10—C11—H11	124.7	N3—C7—H7B	108.3
O1—C11—H11	124.7	H7A—C7—H7B	107.4
C6—N3—C7	121.3 (3)	C9—C8—O1	109.5 (4)
C6—N3—Ni1	114.1 (2)	C9—C8—C7	133.0 (4)
C7—N3—Ni1	124.5 (2)	O1—C8—C7	117.5 (3)
N1—C1—C2	122.4 (4)	C8—C9—C10	106.9 (5)
N1—C1—H1	118.8	C8—C9—H9	126.6
C2—C1—H1	118.8	C10—C9—H9	126.6
C3—C2—C1	119.6 (4)	C11—C10—C9	106.8 (4)
C3—C2—H2	120.2	C11—C10—H10	126.6
C1—C2—H2	120.2	C9—C10—H10	126.6

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—Ni1ⁱ	106.22 (4)	C2—C3—C4—C5	1.4 (6)
Cl1ⁱ—Ni1—Cl1—Ni1ⁱ	0.0	C1—N1—C5—C4	0.2 (5)
N3—Ni1—N1—C1	178.4 (3)	Ni1—N1—C5—C4	177.7 (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—C1	87.0 (3)	C3—C4—C5—N1	−1.5 (6)
N3—Ni1—N1—C5	1.3 (2)	C3—C4—C5—C6	177.5 (4)
Cl2—Ni1—N1—C5	163.5 (2)	C7—N3—C6—C5	177.4 (3)
Cl1—Ni1—N1—C5	19.3 (8)	Ni1—N3—C6—C5	0.4 (4)
Cl1ⁱ—Ni1—N1—C5	−90.1 (2)	N1—C5—C6—N3	0.7 (5)
C8—O1—C11—C10	0.5 (5)	C4—C5—C6—N3	−178.4 (3)
N1—Ni1—N3—C6	−0.9 (2)	C6—N3—C7—C8	0.5 (5)
Cl2—Ni1—N3—C6	−68.1 (4)	Ni1—N3—C7—C8	177.2 (2)
Cl1—Ni1—N3—C6	−178.6 (2)	C11—O1—C8—C9	−0.6 (5)
Cl1ⁱ—Ni1—N3—C6	91.9 (2)	C11—O1—C8—C7	179.7 (3)
N1—Ni1—N3—C7	−177.8 (3)	N3—C7—C8—C9	103.2 (5)
Cl2—Ni1—N3—C7	114.9 (3)	N3—C7—C8—O1	−77.1 (4)
Cl1—Ni1—N3—C7	4.4 (3)	O1—C8—C9—C10	0.4 (5)
Cl1ⁱ—Ni1—N3—C7	−85.1 (3)	C7—C8—C9—C10	−179.9 (4)
C5—N1—C1—C2	1.0 (6)	O1—C11—C10—C9	−0.3 (6)
Ni1—N1—C1—C2	−175.9 (3)	C8—C9—C10—C11	−0.1 (6)

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni₂Cl₄(C₁₁H₁₀N₂O)₂]
M_r	631.64
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.0439 (8), 8.5659 (8), 10.0610 (9)
α, β, γ (°)	77.522 (8), 72.040 (7), 70.132 (8)
V (Å³)	615.39 (10)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.99
Crystal size (mm)	0.30 × 0.30 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.554, 0.572
No. of measured, independent and observed [I > 2σ(I)] reflections	2585, 2408, 1971
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.099, 1.07
No. of reflections	2408
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.58

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

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).

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