Bis[2,4-dichloro-6-(ethyl-imino-meth-yl)phenolato-κN,O]nickel(II).

In the title compound, [Ni(C(9)H(8)Cl(2)NO)(2)], the Ni(II) ion lies on an inversion centre and is coordinated in a slightly distorted square-planar geometry by an N and an O atom from two symmetry-related bidentate 2,4-dichloro-6-(ethyl-imino-meth-yl)phenolate ligands. In the crystal structure, there are short Cl⋯Cl distances of 3.506 (1) and 3.350 (1) Å.

Related literature

For halogen–halogen inter­actions in supra­molecular chemistry and crystal engineering, see: Cohen et al. (1964 ▶); Desiraju (1989 ▶); Xiao & Zhang (2008 ▶); Aakeröy et al. (2011 ▶).

Experimental

Crystal data

[Ni(C9H8Cl2NO)2]

M = 492.84

Monoclinic,

a = 7.5004 (6) Å

b = 9.3155 (7) Å

c = 14.1498 (12) Å

β = 103.841 (1)°

V = 959.94 (13) Å3

Z = 2

Mo Kα radiation

μ = 1.58 mm−1

T = 293 K

0.32 × 0.28 × 0.26 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.612, T max = 0.667

4890 measured reflections

1685 independent reflections

1267 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.055

S = 0.97

1685 reflections

124 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104325X/lh5353sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104325X/lh5353Isup2.hkl

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

[Ni(C9H8Cl2NO)2]	F(000) = 500
Mr = 492.84	Dx = 1.705 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1685 reflections
a = 7.5004 (6) Å	θ = 2.6–25.0°
b = 9.3155 (7) Å	µ = 1.58 mm−1
c = 14.1498 (12) Å	T = 293 K
β = 103.841 (1)°	Block, green
V = 959.94 (13) Å3	0.32 × 0.28 × 0.26 mm
Z = 2

Bruker SMART CCD diffractometer	1685 independent reflections
Radiation source: fine-focus sealed tube	1267 reflections with I > 2σ(I)
graphite	Rint = 0.060
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→7
Tmin = 0.612, Tmax = 0.667	k = −11→8
4890 measured reflections	l = −16→16

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.055	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0012P)2] where P = (Fo2 + 2Fc2)/3
1685 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.35 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
C1	0.6897 (3)	0.3911 (3)	0.06190 (18)	0.0321 (6)
C2	0.5743 (3)	0.3976 (3)	0.12798 (17)	0.0344 (7)
C3	0.4233 (3)	0.3110 (3)	0.11860 (18)	0.0383 (7)
H3A	0.3502	0.3176	0.1631	0.046*
C4	0.3801 (3)	0.2139 (3)	0.0429 (2)	0.0384 (7)
C5	0.4853 (3)	0.2045 (3)	−0.02361 (18)	0.0393 (7)
H5A	0.4546	0.1393	−0.0747	0.047*
C6	0.6402 (3)	0.2937 (3)	−0.01460 (18)	0.0324 (6)
Cl1	0.62781 (9)	0.51726 (8)	0.22421 (4)	0.0454 (2)
Cl2	0.18645 (10)	0.10465 (8)	0.03097 (5)	0.0538 (2)
Ni1	1.0000	0.5000	0.0000	0.03205 (15)
O1	0.8324 (2)	0.47509 (19)	0.07451 (12)	0.0393 (5)
C7	0.7422 (3)	0.2847 (3)	−0.08801 (18)	0.0374 (7)
H7A	0.7023	0.2171	−0.1369	0.045*
C8	0.9509 (4)	0.3268 (3)	−0.18214 (19)	0.0465 (8)
H8A	0.9135	0.2303	−0.2040	0.056*
H8B	1.0840	0.3302	−0.1659	0.056*
C9	0.8770 (4)	0.4311 (4)	−0.26300 (19)	0.0654 (10)
H9A	0.9229	0.4067	−0.3187	0.098*
H9B	0.9155	0.5265	−0.2419	0.098*
H9C	0.7453	0.4266	−0.2800	0.098*
N1	0.8836 (3)	0.3602 (2)	−0.09375 (14)	0.0337 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0305 (15)	0.0322 (17)	0.0333 (15)	0.0026 (13)	0.0070 (13)	0.0053 (13)
C2	0.0343 (16)	0.0373 (17)	0.0315 (15)	0.0041 (13)	0.0078 (13)	0.0053 (13)
C3	0.0341 (16)	0.0456 (19)	0.0376 (16)	0.0033 (14)	0.0132 (14)	0.0094 (15)
C4	0.0303 (16)	0.0388 (17)	0.0449 (17)	−0.0045 (14)	0.0068 (14)	0.0099 (15)
C5	0.0387 (16)	0.0399 (18)	0.0376 (17)	−0.0064 (14)	0.0055 (15)	−0.0018 (13)
C6	0.0329 (15)	0.0315 (16)	0.0332 (15)	−0.0005 (13)	0.0084 (13)	0.0012 (13)
Cl1	0.0483 (4)	0.0536 (5)	0.0372 (4)	−0.0018 (4)	0.0162 (4)	−0.0060 (4)
Cl2	0.0394 (4)	0.0634 (6)	0.0583 (5)	−0.0150 (4)	0.0110 (4)	0.0083 (4)
Ni1	0.0334 (3)	0.0326 (3)	0.0319 (3)	−0.0019 (2)	0.0112 (2)	−0.0032 (2)
O1	0.0403 (11)	0.0445 (13)	0.0372 (10)	−0.0116 (10)	0.0173 (9)	−0.0094 (9)
C7	0.0427 (17)	0.0348 (17)	0.0341 (16)	−0.0010 (14)	0.0077 (14)	−0.0038 (13)
C8	0.0481 (18)	0.051 (2)	0.0465 (18)	−0.0117 (15)	0.0238 (15)	−0.0196 (16)
C9	0.055 (2)	0.105 (3)	0.0394 (18)	−0.013 (2)	0.0178 (17)	0.002 (2)
N1	0.0374 (13)	0.0342 (13)	0.0326 (12)	−0.0020 (11)	0.0143 (11)	−0.0027 (11)

C1—O1	1.303 (3)	Ni1—O1i	1.8382 (16)
C1—C6	1.393 (3)	Ni1—N1i	1.914 (2)
C1—C2	1.419 (3)	Ni1—N1	1.914 (2)
C2—C3	1.372 (3)	C7—N1	1.291 (3)
C2—Cl1	1.731 (3)	C7—H7A	0.9300
C3—C4	1.380 (3)	C8—N1	1.489 (3)
C3—H3A	0.9300	C8—C9	1.502 (4)
C4—C5	1.368 (3)	C8—H8A	0.9700
C4—Cl2	1.749 (3)	C8—H8B	0.9700
C5—C6	1.410 (3)	C9—H9A	0.9600
C5—H5A	0.9300	C9—H9B	0.9600
C6—C7	1.432 (3)	C9—H9C	0.9600
Ni1—O1	1.8382 (16)
O1—C1—C6	123.7 (2)	O1i—Ni1—N1	87.10 (8)
O1—C1—C2	119.6 (2)	N1i—Ni1—N1	180.0
C6—C1—C2	116.7 (2)	C1—O1—Ni1	130.49 (17)
C3—C2—C1	122.1 (3)	N1—C7—C6	127.1 (3)
C3—C2—Cl1	119.1 (2)	N1—C7—H7A	116.5
C1—C2—Cl1	118.9 (2)	C6—C7—H7A	116.5
C2—C3—C4	119.7 (3)	N1—C8—C9	111.6 (2)
C2—C3—H3A	120.1	N1—C8—H8A	109.3
C4—C3—H3A	120.1	C9—C8—H8A	109.3
C5—C4—C3	120.6 (2)	N1—C8—H8B	109.3
C5—C4—Cl2	119.9 (2)	C9—C8—H8B	109.3
C3—C4—Cl2	119.4 (2)	H8A—C8—H8B	108.0
C4—C5—C6	119.9 (3)	C8—C9—H9A	109.5
C4—C5—H5A	120.1	C8—C9—H9B	109.5
C6—C5—H5A	120.1	H9A—C9—H9B	109.5
C1—C6—C5	121.0 (2)	C8—C9—H9C	109.5
C1—C6—C7	120.8 (2)	H9A—C9—H9C	109.5
C5—C6—C7	118.2 (2)	H9B—C9—H9C	109.5
O1—Ni1—O1i	180.00 (13)	C7—N1—C8	112.8 (2)
O1—Ni1—N1i	87.10 (8)	C7—N1—Ni1	124.90 (19)
O1i—Ni1—N1i	92.90 (8)	C8—N1—Ni1	122.30 (17)
O1—Ni1—N1	92.90 (8)