{4,4'-Dibromo-2,2'-[2,2-dimethyl-propane-1,3-diylbis(nitrilo-methanylyl-idene)]diphenolato-κO,N,N',O'}nickel(II).

In the title compound, [Ni(C(19)H(18)Br(2)N(2)O(2))], the Ni(II) ion, lying on a twofold rotation axis, is coordinated by two N atoms and two O atoms from the Schiff base ligand in a distorted square-planar geometry. Weak inter-molecular C-H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For the catalytic properties of Schiff base complexes, see: Cozzi (2004 ▶). For related structures see: Fun et al. (2008 ▶); Kargar et al. (2008 ▶). For the synthesis of the ligand, see: Fairhurst et al. (1995 ▶).

Experimental

Crystal data

[Ni(C19H18Br2N2O2)]

M = 524.84

Monoclinic,

a = 24.227 (6) Å

b = 11.030 (3) Å

c = 7.535 (2) Å

β = 107.939 (19)°

V = 1915.6 (9) Å3

Z = 4

Mo Kα radiation

μ = 5.20 mm−1

T = 298 K

0.30 × 0.20 × 0.15 mm

Data collection

Stoe IPDS-2 diffractometer

Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ▶) T min = 0.289, T max = 0.449

7514 measured reflections

2575 independent reflections

1892 reflections with I > 2σ(I)

R int = 0.142

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.211

S = 1.16

2575 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.99 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009056/hy2415sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009056/hy2415Isup2.hkl

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

[Ni(C19H18Br2N2O2)]	F(000) = 1040.0
Mr = 524.84	Dx = 1.820 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2575 reflections
a = 24.227 (6) Å	θ = 3.2–29.2°
b = 11.030 (3) Å	µ = 5.20 mm−1
c = 7.535 (2) Å	T = 298 K
β = 107.939 (19)°	Plate, brown
V = 1915.6 (9) Å3	0.30 × 0.20 × 0.15 mm
Z = 4

Stoe IPDS-2 diffractometer	2575 independent reflections
Radiation source: fine-focus sealed tube	1892 reflections with I > 2σ(I)
graphite	Rint = 0.142
ω scans	θmax = 29.2°, θmin = 3.2°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	h = −33→24
Tmin = 0.289, Tmax = 0.449	k = −15→13
7514 measured reflections	l = −10→10

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.0955P)2 + 1.9321P] where P = (Fo2 + 2Fc2)/3
2575 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.98 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.0516 (4)	0.4164 (6)	0.2433 (9)	0.0606 (17)
H1A	0.0407	0.4647	0.1319	0.073*
H1B	0.0836	0.3650	0.2432	0.073*
H1C	0.0629	0.4685	0.3505	0.073*
C2	0.0000	0.3381 (7)	0.2500	0.0386 (14)
C3	−0.0173 (2)	0.2567 (5)	0.0764 (6)	0.0376 (10)
H3A	−0.0428	0.3023	−0.0268	0.045*
H3B	0.0173	0.2364	0.0438	0.045*
C4	−0.0989 (2)	0.1277 (5)	−0.0094 (7)	0.0411 (11)
H4	−0.1172	0.1946	−0.0780	0.049*
C5	−0.1317 (2)	0.0172 (5)	−0.0337 (7)	0.0425 (11)
C6	−0.1902 (3)	0.0171 (7)	−0.1506 (8)	0.0546 (14)
H6	−0.2078	0.0894	−0.2018	0.065*
C7	−0.2206 (3)	−0.0880 (7)	−0.1878 (9)	0.0591 (17)
C8	−0.1955 (3)	−0.1976 (7)	−0.1126 (9)	0.0587 (16)
H8	−0.2172	−0.2687	−0.1381	0.070*
C9	−0.1388 (3)	−0.2006 (6)	−0.0009 (8)	0.0518 (14)
H9	−0.1223	−0.2746	0.0462	0.062*
C10	−0.1048 (2)	−0.0934 (5)	0.0447 (7)	0.0404 (11)
N1	−0.04685 (19)	0.1431 (4)	0.0982 (5)	0.0357 (9)
O1	−0.05103 (17)	−0.1011 (3)	0.1491 (5)	0.0427 (8)
Ni1	0.0000	0.02440 (9)	0.2500	0.0336 (3)
Br1	−0.29838 (4)	−0.08575 (11)	−0.35030 (14)	0.0979 (5)

	U11	U22	U33	U12	U13	U23
C1	0.074 (5)	0.048 (4)	0.053 (3)	−0.013 (3)	0.010 (3)	0.002 (3)
C2	0.037 (3)	0.038 (4)	0.036 (3)	0.000	0.004 (3)	0.000
C3	0.041 (3)	0.035 (3)	0.036 (2)	0.000 (2)	0.0104 (19)	0.0032 (18)
C4	0.046 (3)	0.040 (3)	0.036 (2)	0.004 (2)	0.0100 (19)	0.0043 (19)
C5	0.038 (2)	0.046 (3)	0.039 (2)	−0.005 (2)	0.0036 (19)	−0.001 (2)
C6	0.040 (3)	0.058 (4)	0.054 (3)	0.000 (3)	−0.003 (2)	0.008 (3)
C7	0.031 (3)	0.073 (5)	0.060 (3)	−0.014 (3)	−0.007 (2)	−0.003 (3)
C8	0.045 (3)	0.060 (4)	0.064 (3)	−0.018 (3)	0.007 (3)	−0.005 (3)
C9	0.057 (4)	0.039 (3)	0.055 (3)	−0.007 (3)	0.011 (3)	−0.003 (2)
C10	0.040 (3)	0.044 (3)	0.036 (2)	−0.005 (2)	0.0105 (19)	−0.0033 (19)
N1	0.040 (2)	0.036 (2)	0.0277 (15)	−0.0035 (18)	0.0057 (14)	−0.0005 (14)
O1	0.0371 (19)	0.0349 (19)	0.0495 (19)	0.0004 (15)	0.0035 (15)	−0.0030 (14)
Ni1	0.0339 (5)	0.0315 (5)	0.0325 (4)	0.000	0.0060 (3)	0.000
Br1	0.0519 (5)	0.1002 (8)	0.1070 (7)	−0.0251 (5)	−0.0265 (4)	0.0188 (5)

C1—C2	1.533 (8)	C5—C6	1.421 (8)
C1—H1A	0.9600	C5—C10	1.423 (8)
C1—H1B	0.9600	C6—C7	1.354 (10)
C1—H1C	0.9600	C6—H6	0.9300
C2—C1i	1.533 (8)	C7—C8	1.393 (11)
C2—C3	1.535 (7)	C7—Br1	1.906 (6)
C2—C3i	1.535 (7)	C8—C9	1.372 (9)
C3—N1	1.476 (7)	C8—H8	0.9300
C3—H3A	0.9700	C9—C10	1.423 (8)
C3—H3B	0.9700	C9—H9	0.9300
C4—N1	1.284 (7)	C10—O1	1.300 (7)
C4—C5	1.435 (8)	Ni1—N1	1.874 (4)
C4—H4	0.9300	Ni1—O1	1.856 (4)
C2—C1—H1A	109.5	C7—C6—H6	119.9
C2—C1—H1B	109.5	C5—C6—H6	119.9
H1A—C1—H1B	109.5	C6—C7—C8	121.2 (6)
C2—C1—H1C	109.5	C6—C7—Br1	119.2 (5)
H1A—C1—H1C	109.5	C8—C7—Br1	119.5 (5)
H1B—C1—H1C	109.5	C9—C8—C7	119.9 (6)
C1—C2—C1i	111.4 (8)	C9—C8—H8	120.0
C1—C2—C3	108.3 (3)	C7—C8—H8	120.0
C1i—C2—C3	110.2 (3)	C8—C9—C10	121.7 (6)
C1—C2—C3i	110.2 (3)	C8—C9—H9	119.2
C1i—C2—C3i	108.3 (3)	C10—C9—H9	119.2
C3—C2—C3i	108.4 (6)	O1—C10—C5	123.6 (5)
N1—C3—C2	114.6 (4)	O1—C10—C9	119.4 (5)
N1—C3—H3A	108.6	C5—C10—C9	117.0 (5)
C2—C3—H3A	108.6	C4—N1—C3	117.2 (4)
N1—C3—H3B	108.6	C4—N1—Ni1	125.9 (4)
C2—C3—H3B	108.6	C3—N1—Ni1	116.0 (3)
H3A—C3—H3B	107.6	C10—O1—Ni1	128.0 (4)
N1—C4—C5	126.2 (5)	O1—Ni1—O1i	83.5 (2)
N1—C4—H4	116.9	O1—Ni1—N1i	166.70 (17)
C5—C4—H4	116.9	O1i—Ni1—N1i	93.97 (18)
C6—C5—C10	119.9 (6)	O1—Ni1—N1	93.97 (18)
C6—C5—C4	119.1 (6)	O1i—Ni1—N1	166.70 (17)
C10—C5—C4	120.7 (5)	N1i—Ni1—N1	91.3 (3)
C7—C6—C5	120.2 (6)
C1—C2—C3—N1	154.4 (5)	C8—C9—C10—C5	−1.2 (9)
C1i—C2—C3—N1	−83.4 (6)	C5—C4—N1—C3	168.8 (5)
C3i—C2—C3—N1	34.9 (3)	C5—C4—N1—Ni1	0.5 (7)
N1—C4—C5—C6	176.4 (5)	C2—C3—N1—C4	118.2 (5)
N1—C4—C5—C10	−8.9 (8)	C2—C3—N1—Ni1	−72.3 (5)
C10—C5—C6—C7	0.0 (9)	C5—C10—O1—Ni1	9.6 (7)
C4—C5—C6—C7	174.6 (6)	C9—C10—O1—Ni1	−172.6 (4)
C5—C6—C7—C8	0.3 (11)	C10—O1—Ni1—O1i	179.3 (5)
C5—C6—C7—Br1	−178.4 (5)	C10—O1—Ni1—N1i	99.5 (8)
C6—C7—C8—C9	−1.0 (11)	C10—O1—Ni1—N1	−13.9 (4)
Br1—C7—C8—C9	177.7 (5)	C4—N1—Ni1—O1	8.7 (4)
C7—C8—C9—C10	1.5 (10)	C3—N1—Ni1—O1	−159.7 (3)
C6—C5—C10—O1	178.3 (5)	C4—N1—Ni1—O1i	87.3 (9)
C4—C5—C10—O1	3.7 (8)	C3—N1—Ni1—O1i	−81.1 (9)
C6—C5—C10—C9	0.4 (8)	C4—N1—Ni1—N1i	−159.1 (5)
C4—C5—C10—C9	−174.1 (5)	C3—N1—Ni1—N1i	32.5 (3)
C8—C9—C10—O1	−179.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O1ii	0.97	2.40	3.210 (6)	141

Table 1

Selected bond lengths (Å)

Ni1—N1	1.874 (4)
Ni1—O1	1.856 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯O1i	0.97	2.40	3.210 (6)	141

Symmetry code: (i) .