Bis(4-chloro-2-formyl-phenolato)nickel(II).

The asymmetric unit of the title compound, [Ni(C(7)H(4)ClO(2))(2)], contains one half-mol-ecule. The Ni(II) ion, lying on an inversion centre, is four-coordinated by O atoms of 5-chloro-salicylaldehydate 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 = 369.81

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.10

1250 reflections

97 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.43 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807056309/hk2368Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C7H4ClO2)2]	F(000) = 372
Mr = 369.81	Dx = 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

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

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(Fo2) + (0.0455P)2 + 0.5565P] where P = (Fo2 + 2Fc2)/3
1250 reflections	(Δ/σ)max < 0.001
97 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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) .