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

In the title complex, [Ni(C(9)H(9)BrNO)(2)], the Ni(II) ion lies on an inversion centre and is coordinated in a slightly distorted square-planar geometry by two N atoms and two O atoms from two symmetry-related bidentate 4-bromo-2-(ethyl-imino-meth-yl)phenolate ligands. The complex forms a one-dimensional chain in the crystal structure through short C-H⋯Br contacts (H⋯Br = 3.009 Å).

Related literature

For background to Schiff base compounds, see: Gupta & Sutar (2008 ▶); Zhang et al. (2008 ▶, 2009 ▶); Zhang & Feng (2010 ▶); Ge et al. (2011 ▶). For Schiff base coordination models, see: Nakagima et al. (1989 ▶); Zhang et al. (2007 ▶).

Experimental

Crystal data

[Ni(C9H9BrNO)2]

M = 512.83

Monoclinic,

a = 13.456 (6) Å

b = 4.803 (2) Å

c = 14.743 (6) Å

β = 102.157 (8)°

V = 931.4 (7) Å3

Z = 2

Mo Kα radiation

μ = 5.35 mm−1

T = 293 K

0.15 × 0.12 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.465, T max = 0.558

4567 measured reflections

1651 independent reflections

995 reflections with I > 2σ(I)

R int = 0.164

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.142

S = 1.03

1651 reflections

116 parameters

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.52 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020885/bh2357sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020885/bh2357Isup2.hkl

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

[Ni(C9H9BrNO)2]	F(000) = 508
Mr = 512.83	Dx = 1.829 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1651 reflections
a = 13.456 (6) Å	θ = 2.3–25.1°
b = 4.803 (2) Å	µ = 5.35 mm−1
c = 14.743 (6) Å	T = 293 K
β = 102.157 (8)°	Block, green
V = 931.4 (7) Å3	0.15 × 0.12 × 0.11 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	1651 independent reflections
Radiation source: fine-focus sealed tube	995 reflections with I > 2σ(I)
graphite	Rint = 0.164
φ and ω scans	θmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −15→16
Tmin = 0.465, Tmax = 0.558	k = −5→5
4567 measured reflections	l = −17→14

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0386P)2] where P = (Fo2 + 2Fc2)/3
1651 reflections	(Δ/σ)max < 0.001
116 parameters	Δρmax = 0.79 e Å−3
0 restraints	Δρmin = −0.52 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Br1	0.14681 (6)	0.5969 (2)	0.56509 (5)	0.0835 (4)
C1	0.0224 (5)	0.9743 (16)	0.8127 (5)	0.0595 (18)
C2	−0.0114 (6)	1.0740 (16)	0.7195 (5)	0.069 (2)
H2	−0.0590	1.2170	0.7075	0.083*
C3	0.0255 (5)	0.9609 (18)	0.6489 (4)	0.067 (2)
H3	0.0025	1.0257	0.5887	0.080*
C4	0.0964 (5)	0.7519 (18)	0.6657 (4)	0.065 (2)
C5	0.1313 (5)	0.6526 (17)	0.7529 (4)	0.064 (2)
H5	0.1806	0.5139	0.7635	0.077*
C6	0.0921 (5)	0.7616 (15)	0.8278 (4)	0.0556 (17)
C7	0.1305 (5)	0.6525 (16)	0.9196 (5)	0.0638 (19)
H7	0.1794	0.5130	0.9257	0.077*
C8	0.1627 (6)	0.5937 (18)	1.0814 (5)	0.080 (3)
H8A	0.1164	0.5395	1.1206	0.096*
H8B	0.1951	0.4265	1.0646	0.096*
C9	0.2412 (6)	0.783 (2)	1.1336 (6)	0.100 (3)
H9A	0.2914	0.8198	1.0976	0.150*
H9B	0.2730	0.6973	1.1913	0.150*
H9C	0.2100	0.9548	1.1459	0.150*
N1	0.1026 (4)	0.7322 (12)	0.9936 (3)	0.0560 (15)
Ni1	0.0000	1.0000	1.0000	0.0544 (4)
O1	−0.0152 (4)	1.0925 (11)	0.8785 (3)	0.0712 (15)

	U11	U22	U33	U12	U13	U23
Br1	0.0908 (6)	0.1153 (9)	0.0524 (5)	−0.0021 (5)	0.0331 (4)	−0.0090 (4)
C1	0.069 (4)	0.064 (5)	0.049 (4)	−0.013 (4)	0.021 (3)	0.003 (3)
C2	0.086 (5)	0.078 (6)	0.046 (4)	0.012 (4)	0.017 (4)	0.013 (4)
C3	0.075 (5)	0.090 (6)	0.038 (4)	−0.002 (5)	0.017 (3)	0.011 (4)
C4	0.070 (4)	0.089 (6)	0.043 (4)	−0.017 (4)	0.026 (3)	−0.005 (4)
C5	0.067 (5)	0.081 (6)	0.050 (4)	0.011 (4)	0.022 (3)	−0.001 (4)
C6	0.060 (4)	0.061 (5)	0.049 (4)	0.001 (4)	0.019 (3)	0.001 (3)
C7	0.075 (5)	0.060 (5)	0.062 (5)	0.012 (4)	0.026 (4)	0.008 (4)
C8	0.110 (6)	0.078 (6)	0.059 (5)	0.040 (5)	0.033 (5)	0.024 (4)
C9	0.087 (6)	0.141 (9)	0.066 (5)	0.012 (6)	0.001 (5)	0.029 (6)
N1	0.071 (4)	0.061 (4)	0.038 (3)	0.000 (3)	0.018 (3)	0.004 (3)
Ni1	0.0691 (8)	0.0562 (8)	0.0417 (7)	0.0038 (6)	0.0205 (5)	0.0068 (6)
O1	0.093 (4)	0.083 (4)	0.044 (3)	0.027 (3)	0.030 (2)	0.013 (2)

Br1—C4	1.907 (7)	C7—H7	0.9300
C1—O1	1.314 (9)	C8—C9	1.481 (12)
C1—C6	1.373 (10)	C8—N1	1.527 (8)
C1—C2	1.435 (10)	C8—H8A	0.9700
C2—C3	1.358 (10)	C8—H8B	0.9700
C2—H2	0.9300	C9—H9A	0.9600
C3—C4	1.371 (10)	C9—H9B	0.9600
C3—H3	0.9300	C9—H9C	0.9600
C4—C5	1.359 (9)	N1—Ni1	1.904 (6)
C5—C6	1.420 (9)	Ni1—O1i	1.815 (4)
C5—H5	0.9300	Ni1—O1	1.815 (4)
C6—C7	1.442 (9)	Ni1—N1i	1.904 (6)
C7—N1	1.284 (8)
O1—C1—C6	124.0 (6)	C9—C8—H8A	109.3
O1—C1—C2	117.9 (7)	N1—C8—H8A	109.3
C6—C1—C2	118.1 (7)	C9—C8—H8B	109.3
C3—C2—C1	120.5 (7)	N1—C8—H8B	109.3
C3—C2—H2	119.8	H8A—C8—H8B	108.0
C1—C2—H2	119.8	C8—C9—H9A	109.5
C2—C3—C4	120.5 (6)	C8—C9—H9B	109.5
C2—C3—H3	119.8	H9A—C9—H9B	109.5
C4—C3—H3	119.8	C8—C9—H9C	109.5
C5—C4—C3	121.1 (7)	H9A—C9—H9C	109.5
C5—C4—Br1	119.4 (6)	H9B—C9—H9C	109.5
C3—C4—Br1	119.6 (5)	C7—N1—C8	113.2 (6)
C4—C5—C6	119.7 (7)	C7—N1—Ni1	126.0 (5)
C4—C5—H5	120.2	C8—N1—Ni1	120.8 (4)
C6—C5—H5	120.2	O1i—Ni1—O1	180.000 (2)
C1—C6—C5	120.1 (6)	O1i—Ni1—N1i	92.8 (2)
C1—C6—C7	121.3 (6)	O1—Ni1—N1i	87.2 (2)
C5—C6—C7	118.5 (6)	O1i—Ni1—N1	87.2 (2)
N1—C7—C6	125.3 (7)	O1—Ni1—N1	92.8 (2)
N1—C7—H7	117.3	N1i—Ni1—N1	180.0 (3)
C6—C7—H7	117.3	C1—O1—Ni1	129.9 (5)
C9—C8—N1	111.4 (7)