Bis[4-chloro-2-(iminomethyl)phenolato]nickel(II).

In the title centrosymmetric mononuclear nickel(II) complex, [Ni(C(7)H(5)ClNO)(2)], the Ni(II) ion, lying on an inversion center, is four-coordinated by two O and two imine N atoms from two 4-chloro-2-imino-methyl-phenolate ligands, forming a distorted square-planar geometry. In the crystal structure, mol-ecules are linked into a two-dimensional network parallel to the bc plane by C-H⋯O hydrogen bonds.

Related literature

For related structures, see: Hong (2007 ▶); Kamenar et al. (1990 ▶); Li et al. (2005 ▶, 2007 ▶); Zhou et al. (2004 ▶).

Experimental

Crystal data

[Ni(C7H5ClNO)2]

M = 367.85

Monoclinic,

a = 15.775 (6) Å

b = 5.685 (2) Å

c = 7.894 (3) Å

β = 93.864 (18)°

V = 706.3 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.76 mm−1

T = 298 (2) K

0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.743, T max = 0.755

4102 measured reflections

1532 independent reflections

1296 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.084

S = 1.04

1532 reflections

100 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809004279/ci2768sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004279/ci2768Isup2.hkl

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

[Ni(C7H5ClNO)2]	F(000) = 372
Mr = 367.85	Dx = 1.730 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1954 reflections
a = 15.775 (6) Å	θ = 2.8–27.6°
b = 5.685 (2) Å	µ = 1.76 mm−1
c = 7.894 (3) Å	T = 298 K
β = 93.864 (18)°	Block, brown
V = 706.3 (5) Å3	0.18 × 0.17 × 0.17 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	1532 independent reflections
Radiation source: fine-focus sealed tube	1296 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω scans	θmax = 27.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→18
Tmin = 0.743, Tmax = 0.755	k = −7→7
4102 measured reflections	l = −10→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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0495P)2 + 0.0905P] where P = (Fo2 + 2Fc2)/3
1532 reflections	(Δ/σ)max = 0.001
100 parameters	Δρmax = 0.45 e Å−3
1 restraint	Δρmin = −0.30 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	0.5000	0.0000	0.03469 (15)
Cl1	0.06466 (4)	0.34882 (15)	0.19374 (11)	0.0778 (3)
N1	0.45858 (11)	0.2416 (3)	0.1094 (2)	0.0421 (4)
O1	0.39683 (9)	0.6527 (2)	−0.01584 (18)	0.0411 (3)
C1	0.31247 (13)	0.3565 (3)	0.1140 (3)	0.0374 (4)
C2	0.32363 (13)	0.5745 (4)	0.0315 (3)	0.0369 (4)
C3	0.25045 (14)	0.7137 (4)	−0.0045 (3)	0.0445 (5)
H3	0.2554	0.8554	−0.0619	0.053*
C4	0.17234 (15)	0.6450 (4)	0.0433 (3)	0.0501 (6)
H4	0.1252	0.7403	0.0189	0.060*
C5	0.16322 (14)	0.4331 (5)	0.1283 (3)	0.0493 (6)
C6	0.23191 (14)	0.2906 (4)	0.1628 (3)	0.0439 (5)
H6	0.2252	0.1487	0.2190	0.053*
C7	0.38261 (14)	0.1990 (4)	0.1480 (3)	0.0412 (5)
H7	0.3722	0.0571	0.2015	0.049*
H1	0.4993 (14)	0.133 (4)	0.131 (4)	0.080*

	U11	U22	U33	U12	U13	U23
Ni1	0.0430 (2)	0.0274 (2)	0.0335 (2)	0.00107 (14)	0.00128 (15)	0.00308 (13)
Cl1	0.0488 (4)	0.0872 (6)	0.0994 (6)	−0.0016 (3)	0.0197 (3)	0.0169 (4)
N1	0.0470 (10)	0.0325 (9)	0.0465 (10)	0.0054 (7)	0.0023 (8)	0.0076 (7)
O1	0.0437 (8)	0.0314 (7)	0.0483 (9)	0.0025 (6)	0.0049 (6)	0.0063 (6)
C1	0.0467 (11)	0.0305 (10)	0.0348 (10)	−0.0012 (8)	0.0020 (8)	−0.0010 (8)
C2	0.0447 (11)	0.0312 (9)	0.0345 (10)	0.0018 (8)	0.0017 (8)	−0.0021 (8)
C3	0.0510 (12)	0.0351 (11)	0.0469 (13)	0.0042 (9)	0.0004 (10)	0.0025 (9)
C4	0.0470 (12)	0.0463 (14)	0.0565 (14)	0.0086 (10)	−0.0006 (10)	−0.0021 (10)
C5	0.0454 (13)	0.0497 (13)	0.0530 (14)	−0.0026 (10)	0.0052 (10)	−0.0009 (11)
C6	0.0517 (12)	0.0379 (11)	0.0424 (12)	−0.0045 (10)	0.0060 (9)	0.0008 (9)
C7	0.0513 (12)	0.0316 (10)	0.0406 (11)	−0.0007 (9)	0.0037 (9)	0.0066 (8)

Ni1—O1i	1.8414 (15)	C1—C7	1.434 (3)
Ni1—O1	1.8414 (15)	C2—C3	1.412 (3)
Ni1—N1i	1.8455 (18)	C3—C4	1.370 (3)
Ni1—N1	1.8455 (18)	C3—H3	0.93
Cl1—C5	1.738 (2)	C4—C5	1.391 (4)
N1—C7	1.280 (3)	C4—H4	0.93
N1—H1	0.897 (10)	C5—C6	1.365 (3)
O1—C2	1.315 (2)	C6—H6	0.93
C1—C6	1.403 (3)	C7—H7	0.93
C1—C2	1.417 (3)
O1i—Ni1—O1	180.00 (4)	C4—C3—C2	121.5 (2)
O1i—Ni1—N1i	93.89 (7)	C4—C3—H3	119.2
O1—Ni1—N1i	86.11 (7)	C2—C3—H3	119.2
O1i—Ni1—N1	86.11 (7)	C3—C4—C5	120.3 (2)
O1—Ni1—N1	93.89 (7)	C3—C4—H4	119.9
N1i—Ni1—N1	180.00 (10)	C5—C4—H4	119.9
C7—N1—Ni1	128.97 (15)	C6—C5—C4	120.2 (2)
C7—N1—H1	120 (2)	C6—C5—Cl1	119.4 (2)
Ni1—N1—H1	111 (2)	C4—C5—Cl1	120.37 (19)
C2—O1—Ni1	127.63 (13)	C5—C6—C1	120.6 (2)
C6—C1—C2	120.15 (18)	C5—C6—H6	119.7
C6—C1—C7	118.94 (19)	C1—C6—H6	119.7
C2—C1—C7	120.91 (19)	N1—C7—C1	124.10 (19)
O1—C2—C3	118.37 (19)	N1—C7—H7	118.0
O1—C2—C1	124.41 (18)	C1—C7—H7	118.0
C3—C2—C1	117.21 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ii	0.93	2.54	3.318 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.93	2.54	3.318 (3)	142

Symmetry code: (i) .