Bis(4-chloro-2-formyl­phenolato)nickel(II)

Li, Z.; Zhang, X.; Pu, X.

doi:10.1107/S1600536807056309

metal-organic compounds

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RETRACTED ARTICLE

This article has been retracted. To view the retraction notice, click here.

Retracted: Bis(4-chloro-2-formylphenolato)nickel(II)

Zongxiao Li,^a ^* Xinli Zhang ^a and Xiaohua Pu ^a

^aDepartment of Chemistry, Baoji University of Arts and Science, Baoji, Shaanxi 721007, People's Republic of China
^*Correspondence e-mail: mingtian8001@163.com

(Received 5 November 2007; accepted 6 November 2007; online 18 December 2007)

The asymmetric unit of the title compound, [Ni(C₇H₄ClO₂)₂], contains one half-molecule. The Ni^II ion, lying on an inversion centre, is four-coordinated by O atoms of 5-chlorosalicylaldehydate ligands in a square-planar geometry.

Related literature

For general background, see: Gavrilova & Bosnich (2004 ); Boudalis et al. (2004 ); Veauthier et al. (2004 ). For related structures, see: Erxleben et al. (2001 ). For bond-length data, see: Allen et al. 1987 .

Experimental

Crystal data

[Ni(C₇H₄ClO₂)₂]
M_r = 369.81
Monoclinic, P 2₁ /c
a = 15.765 (3) Å
b = 5.6921 (14) Å
c = 7.8869 (14) Å
β = 93.896 (2)°
V = 706.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.76 mm⁻¹
T = 298 (2) K
0.20 × 0.17 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.720, T_max = 0.816
3455 measured reflections
1250 independent reflections
1056 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.093
S = 1.10
1250 reflections
97 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—O2	1.840 (2)
Ni1—O1	1.851 (3)

O2ⁱ—Ni1—O2	180
O2ⁱ—Ni1—O1	85.60 (10)
O2—Ni1—O1	94.40 (10)
O1—Ni1—O1ⁱ	180
Symmetry code: (i) -x+1, -y, -z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1995 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807056309/hk2368sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807056309/hk2368Isup2.hkl

checkCIF report

Comment top

The design of multidentate ligands and their metallosupramolecular chemistry are of great interest in the last few years (Gavrilova & Bosnich, 2004; Boudalis et al., 2004; Veauthier et al., 2004). As an extension of our ongoing studies on the structural characterization of Schiff base compounds, we report herein the crystal structure of the title compound, (I).

The asymmetric unit of (I) contains one-half molecule (Fig. 1), in which the bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987). It is a mononuclear Ni^II complex being structurally similar to the Co(II) and Zn(II) complexes derived from other Schiff base ligands (Erxleben et al., 2001). The Ni^II ion is four-coordinated by symmetry-related O atoms of 5-chlorosalicylaldehydato ligands.

Related literature top

For general background, see: Gavrilova & Bosnich (2004); Boudalis et al. (2004); Veauthier et al. (2004). For related structures, see: Erxleben et al. (2001). For bond-length data, see: Allen et al. 1987.

Experimental top

For the preparation of the title compound, (I), 5-chlorosalicylaldehyde (15.7 mg, 0.1 mmol) and Ni(NO₃)₂.6(H₂O) (29.0 mg, 0.1 mmol) were dissolved in methanol (10 ml). The mixture was stirred for 30 min at room temperature to give a clear brown solution. After allowing the resulting solution to stand in air for 11 d, brown block-shaped crystals of (I) were formed by slow evaporation of the solvent. The crystals were collected, washed with methanol and dried in a vacuum desiccator using anhydrous CaCl₂ (yield; 54%). Elemental analysis; found C 45.42%, H2.16%; calc. for C₁₄H₈Cl₂Ni O₄: C 45.44, H 2.61%.

Structure description top

For general background, see: Gavrilova & Bosnich (2004); Boudalis et al. (2004); Veauthier et al. (2004). For related structures, see: Erxleben et al. (2001). For bond-length data, see: Allen et al. 1987.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELXTL (Sheldrick, 1995).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Bis(4-chloro-2-formylphenolato)nickel(II) top

Crystal data top

[Ni(C₇H₄ClO₂)₂]	F(000) = 372
M_r = 369.81	D_x = 1.739 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1788 reflections
a = 15.765 (3) Å	θ = 2.6–27.2°
b = 5.6921 (14) Å	µ = 1.76 mm⁻¹
c = 7.8869 (14) Å	T = 298 K
β = 93.896 (2)°	Block, brown
V = 706.1 (3) Å³	0.20 × 0.17 × 0.12 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	1250 independent reflections
Radiation source: fine-focus sealed tube	1056 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
φ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→15
T_min = 0.720, T_max = 0.816	k = −6→6
3455 measured reflections	l = −7→9

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0455P)² + 0.5565P] where P = (F_o² + 2F_c²)/3
1250 reflections	(Δ/σ)_max < 0.001
97 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Ni(C₇H₄ClO₂)₂]	V = 706.1 (3) Å³
M_r = 369.81	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.765 (3) Å	µ = 1.76 mm⁻¹
b = 5.6921 (14) Å	T = 298 K
c = 7.8869 (14) Å	0.20 × 0.17 × 0.12 mm
β = 93.896 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1250 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1056 reflections with I > 2σ(I)
T_min = 0.720, T_max = 0.816	R_int = 0.019
3455 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.10	Δρ_max = 0.55 e Å⁻³
1250 reflections	Δρ_min = −0.43 e Å⁻³
97 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	0.5000	0.0000	0.0000	0.0368 (2)
Cl1	0.06478 (6)	0.1508 (2)	0.19360 (16)	0.0813 (4)
O1	0.45925 (17)	0.2599 (5)	0.1098 (3)	0.0634 (7)
O2	0.39686 (13)	−0.1524 (3)	−0.0165 (3)	0.0434 (5)
C1	0.3822 (2)	0.3016 (5)	0.1485 (4)	0.0425 (7)
H1	0.3714	0.4431	0.2018	0.051*
C2	0.3126 (2)	0.1431 (5)	0.1141 (4)	0.0398 (7)
C3	0.32369 (19)	−0.0744 (6)	0.0312 (4)	0.0389 (7)
C4	0.2507 (2)	−0.2141 (6)	−0.0042 (4)	0.0465 (8)
H4	0.2557	−0.3559	−0.0613	0.056*
C5	0.1722 (2)	−0.1449 (6)	0.0438 (5)	0.0528 (9)
H5	0.1250	−0.2402	0.0197	0.063*
C6	0.1633 (2)	0.0666 (7)	0.1281 (4)	0.0497 (8)
C7	0.2316 (2)	0.2091 (6)	0.1627 (4)	0.0460 (8)
H7	0.2248	0.3508	0.2189	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0449 (3)	0.0309 (3)	0.0342 (3)	−0.0012 (2)	0.0001 (2)	−0.0031 (2)
Cl1	0.0502 (6)	0.0935 (9)	0.1021 (9)	0.0018 (5)	0.0186 (5)	−0.0168 (7)
O1	0.0725 (18)	0.0565 (15)	0.0609 (16)	−0.0023 (13)	0.0037 (13)	−0.0085 (13)
O2	0.0464 (12)	0.0340 (11)	0.0499 (13)	−0.0011 (9)	0.0035 (10)	−0.0066 (10)
C1	0.0490 (19)	0.0354 (16)	0.0433 (18)	0.0045 (14)	0.0057 (14)	−0.0065 (14)
C2	0.0469 (17)	0.0353 (17)	0.0369 (16)	0.0006 (13)	0.0008 (13)	0.0006 (13)
C3	0.0461 (18)	0.0350 (15)	0.0351 (16)	−0.0009 (13)	−0.0004 (13)	0.0037 (13)
C4	0.054 (2)	0.0388 (17)	0.0462 (19)	−0.0042 (14)	0.0003 (15)	−0.0023 (14)
C5	0.0481 (19)	0.053 (2)	0.056 (2)	−0.0091 (16)	0.0002 (16)	0.0002 (17)
C6	0.0443 (18)	0.055 (2)	0.050 (2)	0.0024 (15)	0.0048 (15)	0.0025 (16)
C7	0.0518 (19)	0.0422 (18)	0.0441 (19)	0.0056 (15)	0.0046 (15)	−0.0015 (14)

Geometric parameters (Å, º) top

Ni1—O2ⁱ	1.840 (2)	C2—C7	1.408 (4)
Ni1—O2	1.840 (2)	C2—C3	1.417 (4)
Ni1—O1	1.851 (3)	C3—C4	1.411 (4)
Ni1—O1ⁱ	1.851 (3)	C4—C5	1.376 (5)
Cl1—C6	1.738 (3)	C4—H4	0.9300
O1—C1	1.294 (4)	C5—C6	1.387 (5)
O2—C3	1.315 (4)	C5—H5	0.9300
C1—C2	1.433 (4)	C6—C7	1.361 (5)
C1—H1	0.9300	C7—H7	0.9300

O2ⁱ—Ni1—O2	180	O2—C3—C2	124.5 (3)
O2ⁱ—Ni1—O1	85.60 (10)	C4—C3—C2	117.3 (3)
O2—Ni1—O1	94.40 (10)	C5—C4—C3	121.4 (3)
O2ⁱ—Ni1—O1ⁱ	94.40 (10)	C5—C4—H4	119.3
O2—Ni1—O1ⁱ	85.60 (10)	C3—C4—H4	119.3
O1—Ni1—O1ⁱ	180	C4—C5—C6	120.2 (3)
C1—O1—Ni1	128.2 (2)	C4—C5—H5	119.9
C3—O2—Ni1	127.52 (19)	C6—C5—H5	119.9
O1—C1—C2	124.0 (3)	C7—C6—C5	120.6 (3)
O1—C1—H1	118.0	C7—C6—Cl1	119.1 (3)
C2—C1—H1	118.0	C5—C6—Cl1	120.2 (3)
C7—C2—C3	120.1 (3)	C6—C7—C2	120.4 (3)
C7—C2—C1	118.5 (3)	C6—C7—H7	119.8
C3—C2—C1	121.3 (3)	C2—C7—H7	119.8
O2—C3—C4	118.2 (3)

O2ⁱ—Ni1—O1—C1	177.8 (3)	C7—C2—C3—C4	2.0 (4)
O2—Ni1—O1—C1	−2.2 (3)	C1—C2—C3—C4	−177.2 (3)
O1—Ni1—O2—C3	3.1 (3)	O2—C3—C4—C5	179.2 (3)
O1ⁱ—Ni1—O2—C3	−176.9 (3)	C2—C3—C4—C5	−1.7 (5)
Ni1—O1—C1—C2	1.5 (5)	C3—C4—C5—C6	0.4 (5)
O1—C1—C2—C7	179.9 (3)	C4—C5—C6—C7	0.6 (5)
O1—C1—C2—C3	−0.8 (5)	C4—C5—C6—Cl1	−178.4 (3)
Ni1—O2—C3—C4	175.5 (2)	C5—C6—C7—C2	−0.3 (5)
Ni1—O2—C3—C2	−3.5 (4)	Cl1—C6—C7—C2	178.7 (2)
C7—C2—C3—O2	−178.9 (3)	C3—C2—C7—C6	−1.1 (5)
C1—C2—C3—O2	1.9 (5)	C1—C2—C7—C6	178.1 (3)

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Ni(C₇H₄ClO₂)₂]
M_r	369.81
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	15.765 (3), 5.6921 (14), 7.8869 (14)
β (°)	93.896 (2)
V (Å³)	706.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.76
Crystal size (mm)	0.20 × 0.17 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.720, 0.816
No. of measured, independent and observed [I > 2σ(I)] reflections	3455, 1250, 1056
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.093, 1.10
No. of reflections	1250
No. of parameters	97
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.43

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1995).

Selected geometric parameters (Å, º) top

Ni1—O2	1.840 (2)	Ni1—O1	1.851 (3)

O2ⁱ—Ni1—O2	180	O2—Ni1—O1	94.40 (10)
O2ⁱ—Ni1—O1	85.60 (10)	O1—Ni1—O1ⁱ	180

Symmetry code: (i) −x+1, −y, −z.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Boudalis, A. K., Clemente-Juan, J.-M., Dahan, F. & Tuchagues, J.-P. (2004). Inorg. Chem. 43, 1574–1586. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Erxleben, A. & Schumacher, D. (2001). Eur. J. Inorg. Chem. pp. 3039–3046. CrossRef Google Scholar
Gavrilova, A. L. & Bosnich, B. (2004). Chem. Rev. 104, 349–383. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1995). SHELXTL. Version 5.0. Siemens Analytical Instruments Inc, Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Veauthier, J. M., Cho, W.-S., Lynch, V. M. & Sessler, J. L. (2004). Inorg. Chem. 43, 1220–1228. Web of Science CSD CrossRef PubMed CAS Google Scholar

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m215

https://doi.org/10.1107/S1600536807056309

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