Bis[2-(benzyl-imino-meth-yl)-4-chloro-phenolato-κN,O]nickel(II).

In the mononuclear centrosymmetric title compound, [Ni(C(14)H(11)ClNO)(2)], the Ni(II) atom, lying on a center of symmetry, is four-coordinated by two O atoms and two N atoms from two Schiff base ligands, forming a slightly distorted square-planar environment. The dihedral angle between the two aromatic rings of the ligand is 72.0 (2)°. No significant hydrogen bonding or π-π stacking inter-actions are observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related literature, see: Christensen et al. (1997 ▶); Costes et al. (2005 ▶); Hu et al. (2005 ▶); Liu et al. (2006 ▶); Wallis & Cummings (1974 ▶); Yu (2006 ▶).

Experimental

Crystal data

[Ni(C14H11ClNO)2]

M = 548.09

Monoclinic,

a = 13.6785 (17) Å

b = 10.5986 (14) Å

c = 8.6560 (13) Å

β = 107.529 (2)°

V = 1196.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.06 mm−1

T = 298 (2) K

0.56 × 0.44 × 0.32 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.587, T max = 0.727

5718 measured reflections

2110 independent reflections

1506 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.124

S = 1.08

2110 reflections

160 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2001 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807054943/ci2496sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807054943/ci2496Isup2.hkl

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

[Ni(C14H11ClNO)2]	F000 = 564
Mr = 548.09	Dx = 1.521 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1825 reflections
a = 13.6785 (17) Å	θ = 2.5–25.2º
b = 10.5986 (14) Å	µ = 1.06 mm−1
c = 8.6560 (13) Å	T = 298 (2) K
β = 107.529 (2)º	Rhombus, green
V = 1196.6 (3) Å3	0.56 × 0.44 × 0.32 mm
Z = 2

Bruker SMART CCD diffractometer	2110 independent reflections
Radiation source: fine-focus sealed tube	1506 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −16→12
Tmin = 0.587, Tmax = 0.727	k = −12→8
5718 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.057P)2 + 0.6708P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2110 reflections	Δρmax = 0.53 e Å−3
160 parameters	Δρmin = −0.28 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.0000	0.5000	0.0000	0.0329 (2)
Cl1	0.48272 (9)	0.77502 (16)	0.44350 (18)	0.0919 (6)
N1	0.0104 (2)	0.6504 (3)	0.1288 (3)	0.0316 (7)
O1	0.13607 (19)	0.4664 (3)	0.0829 (3)	0.0472 (7)
C1	0.0949 (3)	0.7006 (4)	0.2141 (4)	0.0354 (8)
H1	0.0899	0.7737	0.2705	0.043*
C2	0.1963 (3)	0.6549 (4)	0.2309 (4)	0.0359 (9)
C3	0.2107 (3)	0.5393 (4)	0.1629 (4)	0.0365 (9)
C4	0.3123 (3)	0.4982 (4)	0.1878 (5)	0.0467 (10)
H4	0.3240	0.4208	0.1461	0.056*
C5	0.3939 (3)	0.5699 (5)	0.2720 (5)	0.0528 (11)
H5	0.4603	0.5418	0.2855	0.063*
C6	0.3779 (3)	0.6840 (5)	0.3372 (5)	0.0520 (11)
C7	0.2809 (3)	0.7283 (4)	0.3197 (5)	0.0451 (10)
H7	0.2710	0.8048	0.3653	0.054*
C8	−0.0831 (3)	0.7179 (4)	0.1351 (4)	0.0369 (9)
H8A	−0.1254	0.7353	0.0253	0.044*
H8B	−0.0633	0.7982	0.1893	0.044*
C9	−0.1461 (2)	0.6457 (3)	0.2219 (4)	0.0316 (8)
C10	−0.1084 (3)	0.5490 (4)	0.3262 (4)	0.0393 (9)
H10	−0.0411	0.5225	0.3438	0.047*
C11	−0.1688 (3)	0.4897 (4)	0.4064 (5)	0.0469 (10)
H11	−0.1422	0.4233	0.4767	0.056*
C12	−0.2678 (3)	0.5281 (4)	0.3827 (5)	0.0533 (12)
H12	−0.3087	0.4878	0.4361	0.064*
C13	−0.3059 (3)	0.6264 (5)	0.2799 (5)	0.0553 (12)
H13	−0.3725	0.6544	0.2651	0.066*
C14	−0.2457 (3)	0.6839 (4)	0.1983 (5)	0.0458 (10)
H14	−0.2727	0.7493	0.1265	0.055*

	U11	U22	U33	U12	U13	U23
Ni1	0.0295 (4)	0.0348 (4)	0.0367 (4)	−0.0008 (3)	0.0133 (3)	−0.0002 (3)
Cl1	0.0415 (7)	0.1240 (14)	0.1083 (11)	−0.0314 (7)	0.0197 (7)	−0.0503 (10)
N1	0.0291 (15)	0.0328 (17)	0.0363 (16)	0.0014 (13)	0.0152 (13)	0.0075 (13)
O1	0.0307 (14)	0.0475 (19)	0.0590 (17)	0.0032 (11)	0.0070 (13)	−0.0124 (13)
C1	0.040 (2)	0.031 (2)	0.040 (2)	−0.0020 (16)	0.0191 (17)	0.0023 (16)
C2	0.0311 (19)	0.043 (2)	0.035 (2)	−0.0034 (17)	0.0123 (15)	0.0036 (18)
C3	0.033 (2)	0.045 (2)	0.035 (2)	−0.0018 (16)	0.0137 (17)	0.0024 (17)
C4	0.035 (2)	0.053 (3)	0.054 (2)	0.0008 (19)	0.0156 (18)	−0.010 (2)
C5	0.031 (2)	0.069 (3)	0.059 (3)	−0.001 (2)	0.0156 (19)	−0.005 (2)
C6	0.034 (2)	0.073 (3)	0.050 (2)	−0.014 (2)	0.0137 (18)	−0.008 (2)
C7	0.037 (2)	0.049 (3)	0.051 (2)	−0.0103 (18)	0.0162 (18)	−0.008 (2)
C8	0.038 (2)	0.032 (2)	0.043 (2)	0.0018 (16)	0.0163 (17)	0.0026 (17)
C9	0.0308 (18)	0.033 (2)	0.0309 (19)	−0.0009 (15)	0.0095 (15)	−0.0046 (16)
C10	0.039 (2)	0.037 (2)	0.043 (2)	0.0046 (17)	0.0142 (17)	0.0024 (18)
C11	0.055 (3)	0.043 (2)	0.047 (2)	0.003 (2)	0.0222 (19)	0.009 (2)
C12	0.049 (2)	0.067 (3)	0.053 (2)	−0.012 (2)	0.029 (2)	−0.001 (2)
C13	0.035 (2)	0.079 (4)	0.055 (3)	0.005 (2)	0.019 (2)	0.002 (2)
C14	0.040 (2)	0.055 (3)	0.043 (2)	0.0121 (19)	0.0139 (18)	0.010 (2)

Ni1—O1	1.817 (2)	C6—C7	1.372 (5)
Ni1—O1i	1.817 (2)	C7—H7	0.93
Ni1—N1i	1.926 (3)	C8—C9	1.510 (5)
Ni1—N1	1.926 (3)	C8—H8A	0.97
Cl1—C6	1.743 (4)	C8—H8B	0.97
N1—C1	1.284 (4)	C9—C10	1.361 (5)
N1—C8	1.480 (4)	C9—C14	1.377 (5)
O1—C3	1.301 (4)	C10—C11	1.380 (5)
C1—C2	1.434 (5)	C10—H10	0.93
C1—H1	0.93	C11—C12	1.369 (6)
C2—C3	1.399 (5)	C11—H11	0.93
C2—C7	1.414 (5)	C12—C13	1.367 (6)
C3—C4	1.409 (5)	C12—H12	0.93
C4—C5	1.365 (6)	C13—C14	1.378 (6)
C4—H4	0.93	C13—H13	0.93
C5—C6	1.379 (6)	C14—H14	0.93
C5—H5	0.93
O1—Ni1—O1i	180	C6—C7—C2	118.6 (4)
O1—Ni1—N1i	87.39 (11)	C6—C7—H7	120.7
O1i—Ni1—N1i	92.61 (11)	C2—C7—H7	120.7
O1—Ni1—N1	92.61 (11)	N1—C8—C9	113.7 (3)
O1i—Ni1—N1	87.39 (11)	N1—C8—H8A	108.8
N1i—Ni1—N1	180.00 (14)	C9—C8—H8A	108.8
C1—N1—C8	114.6 (3)	N1—C8—H8B	108.8
C1—N1—Ni1	124.9 (2)	C9—C8—H8B	108.8
C8—N1—Ni1	120.5 (2)	H8A—C8—H8B	107.7
C3—O1—Ni1	129.8 (3)	C10—C9—C14	118.7 (3)
N1—C1—C2	126.4 (4)	C10—C9—C8	123.5 (3)
N1—C1—H1	116.8	C14—C9—C8	117.7 (3)
C2—C1—H1	116.8	C9—C10—C11	120.8 (3)
C3—C2—C7	120.9 (3)	C9—C10—H10	119.6
C3—C2—C1	120.5 (3)	C11—C10—H10	119.6
C7—C2—C1	118.5 (4)	C12—C11—C10	120.3 (4)
O1—C3—C2	123.8 (3)	C12—C11—H11	119.9
O1—C3—C4	118.5 (4)	C10—C11—H11	119.9
C2—C3—C4	117.6 (3)	C13—C12—C11	119.4 (4)
C5—C4—C3	121.3 (4)	C13—C12—H12	120.3
C5—C4—H4	119.3	C11—C12—H12	120.3
C3—C4—H4	119.3	C12—C13—C14	120.1 (4)
C4—C5—C6	120.1 (4)	C12—C13—H13	120.0
C4—C5—H5	120.0	C14—C13—H13	120.0
C6—C5—H5	120.0	C9—C14—C13	120.7 (4)
C7—C6—C5	121.4 (4)	C9—C14—H14	119.6
C7—C6—Cl1	118.9 (4)	C13—C14—H14	119.6
C5—C6—Cl1	119.6 (3)
O1—Ni1—N1—C1	9.0 (3)	C4—C5—C6—C7	0.0 (7)
O1i—Ni1—N1—C1	−171.0 (3)	C4—C5—C6—Cl1	−179.7 (3)
O1—Ni1—N1—C8	−171.1 (2)	C5—C6—C7—C2	−0.8 (6)
O1i—Ni1—N1—C8	8.9 (2)	Cl1—C6—C7—C2	178.9 (3)
N1i—Ni1—O1—C3	164.0 (3)	C3—C2—C7—C6	0.4 (5)
N1—Ni1—O1—C3	−16.0 (3)	C1—C2—C7—C6	179.3 (3)
C8—N1—C1—C2	179.6 (3)	C1—N1—C8—C9	−111.5 (3)
Ni1—N1—C1—C2	−0.4 (5)	Ni1—N1—C8—C9	68.5 (3)
N1—C1—C2—C3	−6.1 (6)	N1—C8—C9—C10	19.2 (5)
N1—C1—C2—C7	174.9 (3)	N1—C8—C9—C14	−163.5 (3)
Ni1—O1—C3—C2	14.1 (5)	C14—C9—C10—C11	0.4 (6)
Ni1—O1—C3—C4	−168.2 (3)	C8—C9—C10—C11	177.6 (4)
C7—C2—C3—O1	178.5 (3)	C9—C10—C11—C12	−0.5 (6)
C1—C2—C3—O1	−0.5 (5)	C10—C11—C12—C13	−0.5 (6)
C7—C2—C3—C4	0.7 (5)	C11—C12—C13—C14	1.5 (7)
C1—C2—C3—C4	−178.2 (3)	C10—C9—C14—C13	0.7 (6)
O1—C3—C4—C5	−179.4 (4)	C8—C9—C14—C13	−176.8 (4)
C2—C3—C4—C5	−1.5 (6)	C12—C13—C14—C9	−1.6 (7)
C3—C4—C5—C6	1.1 (6)

Ni1—O1	1.817 (2)
Ni1—N1	1.926 (3)

O1—Ni1—O1i	180
O1—Ni1—N1i	87.39 (11)
O1—Ni1—N1	92.61 (11)

Symmetry code: (i) .