{4,4',6,6'-Tetra-bromo-2,2'-[2,2-dimethyl-propane-1,3-diylbis(nitrilo-methanylyl-idene)]diphenolato}nickel(II).

The asymmetric unit of the title compound, [Ni(C(19)H(16)Br(4)N(2)O(2))], comprises half of a Schiff base complex. The geometry around the Ni(II) atom, located on a twofold rotation axis, is distorted square-planar, which is supported by the N(2)O(2) donor atoms of the coordinated ligand. The dihedral angle between the substituted benzene rings is 23.19 (17)°. In the crystal, a short inter-molecular Br⋯Br [3.6475 (7) Å] inter-action is present.

Related literature

For applications of Schiff bases in coordination chemistry, see: Granovski et al. (1993 ▶); Blower (1998 ▶). For related structures, see: Ghaemi et al. (2011 ▶); Kargar et al. (2012 ▶). For van der Waals radii, see: Bondi (1964 ▶). For standard values of bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Ni(C19H16Br4N2O2)]

M = 682.69

Orthorhombic,

a = 16.1125 (11) Å

b = 15.4789 (12) Å

c = 8.4734 (5) Å

V = 2113.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 8.50 mm−1

T = 296 K

0.25 × 0.18 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.694, T max = 0.871

16236 measured reflections

2086 independent reflections

1574 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.075

S = 1.05

2086 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.78 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812020375/su2421sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020375/su2421Isup2.hkl

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

[Ni(C19H16Br4N2O2)]	F(000) = 1312
Mr = 682.69	Dx = 2.146 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2540 reflections
a = 16.1125 (11) Å	θ = 2.5–27.4°
b = 15.4789 (12) Å	µ = 8.50 mm−1
c = 8.4734 (5) Å	T = 296 K
V = 2113.3 (3) Å3	Block, dark-red
Z = 4	0.25 × 0.18 × 0.09 mm

Bruker SMART APEXII CCD area-detector diffractometer	2086 independent reflections
Radiation source: fine-focus sealed tube	1574 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ and ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→19
Tmin = 0.694, Tmax = 0.871	k = −14→19
16236 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0387P)2 + 0.4809P] where P = (Fo2 + 2Fc2)/3
2086 reflections	(Δ/σ)max = 0.001
129 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.78 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	0.34274 (3)	−0.24016 (2)	0.18392 (5)	0.04218 (15)
Br2	0.10156 (3)	−0.05088 (3)	−0.14763 (7)	0.06551 (19)
Ni1	0.5000	0.02131 (4)	0.2500	0.02663 (17)
O1	0.43065 (15)	−0.06700 (15)	0.1850 (3)	0.0344 (6)
N1	0.44411 (18)	0.10588 (18)	0.1331 (3)	0.0281 (7)
C1	0.3595 (2)	−0.0600 (2)	0.1155 (4)	0.0284 (8)
C2	0.3081 (2)	−0.1331 (2)	0.0964 (4)	0.0293 (8)
C3	0.2334 (2)	−0.1309 (3)	0.0186 (4)	0.0337 (9)
H3	0.2019	−0.1809	0.0073	0.040*
C4	0.2054 (2)	−0.0533 (3)	−0.0427 (4)	0.0372 (9)
C5	0.2510 (2)	0.0203 (3)	−0.0270 (5)	0.0391 (10)
H5	0.2312	0.0721	−0.0681	0.047*
C6	0.3279 (2)	0.0180 (2)	0.0515 (4)	0.0304 (8)
C7	0.3763 (2)	0.0952 (2)	0.0563 (4)	0.0317 (8)
H7	0.3569	0.1420	−0.0017	0.038*
C8	0.4910 (2)	0.1859 (2)	0.1043 (4)	0.0334 (9)
H8A	0.4631	0.2189	0.0227	0.040*
H8B	0.5458	0.1711	0.0655	0.040*
C9	0.5000	0.2419 (3)	0.2500	0.0320 (12)
C10	0.4239 (3)	0.2995 (3)	0.2735 (5)	0.0499 (11)
H10A	0.3746	0.2647	0.2718	0.075*
H10B	0.4213	0.3415	0.1901	0.075*
H10C	0.4280	0.3286	0.3732	0.075*

	U11	U22	U33	U12	U13	U23
Br1	0.0576 (3)	0.0265 (2)	0.0424 (3)	−0.00786 (19)	−0.00041 (19)	0.00544 (17)
Br2	0.0449 (3)	0.0558 (3)	0.0958 (4)	−0.0040 (2)	−0.0292 (3)	−0.0020 (3)
Ni1	0.0301 (3)	0.0205 (4)	0.0292 (3)	0.000	−0.0007 (3)	0.000
O1	0.0369 (15)	0.0238 (14)	0.0425 (14)	−0.0025 (12)	−0.0059 (12)	0.0023 (12)
N1	0.0348 (17)	0.0206 (16)	0.0290 (16)	−0.0047 (14)	−0.0020 (13)	0.0011 (13)
C1	0.033 (2)	0.027 (2)	0.0257 (18)	−0.0035 (17)	0.0038 (16)	−0.0003 (16)
C2	0.036 (2)	0.0226 (19)	0.0293 (19)	−0.0016 (16)	0.0045 (16)	0.0015 (16)
C3	0.033 (2)	0.035 (2)	0.033 (2)	−0.0105 (18)	0.0043 (16)	−0.0045 (18)
C4	0.030 (2)	0.038 (2)	0.044 (2)	−0.0040 (19)	−0.0042 (17)	−0.0042 (19)
C5	0.043 (2)	0.031 (2)	0.043 (2)	0.0032 (19)	−0.0058 (18)	−0.0022 (19)
C6	0.034 (2)	0.026 (2)	0.0315 (19)	−0.0034 (16)	−0.0011 (16)	0.0023 (16)
C7	0.040 (2)	0.023 (2)	0.0326 (19)	0.0003 (17)	0.0001 (17)	0.0042 (17)
C8	0.045 (2)	0.024 (2)	0.0313 (19)	−0.0084 (18)	−0.0001 (17)	0.0036 (16)
C9	0.038 (3)	0.020 (3)	0.038 (3)	0.000	−0.001 (2)	0.000
C10	0.057 (3)	0.040 (3)	0.053 (3)	0.019 (2)	−0.006 (2)	0.003 (2)

Br1—C2	1.899 (3)	C4—C5	1.362 (5)
Br2—C4	1.895 (4)	C5—C6	1.407 (5)
Ni1—O1	1.849 (2)	C5—H5	0.9300
Ni1—O1i	1.849 (2)	C6—C7	1.428 (5)
Ni1—N1i	1.872 (3)	C7—H7	0.9300
Ni1—N1	1.872 (3)	C8—C9	1.515 (4)
O1—C1	1.293 (4)	C8—H8A	0.9700
N1—C7	1.282 (4)	C8—H8B	0.9700
N1—C8	1.471 (4)	C9—C8i	1.515 (4)
C1—C2	1.412 (5)	C9—C10i	1.529 (5)
C1—C6	1.418 (5)	C9—C10	1.529 (5)
C2—C3	1.373 (5)	C10—H10A	0.9600
C3—C4	1.384 (5)	C10—H10B	0.9600
C3—H3	0.9300	C10—H10C	0.9600
O1—Ni1—O1i	84.69 (15)	C5—C6—C1	121.3 (3)
O1—Ni1—N1i	164.78 (11)	C5—C6—C7	118.3 (3)
O1i—Ni1—N1i	93.94 (11)	C1—C6—C7	120.3 (3)
O1—Ni1—N1	93.94 (11)	N1—C7—C6	126.0 (3)
O1i—Ni1—N1	164.78 (11)	N1—C7—H7	117.0
N1i—Ni1—N1	91.27 (17)	C6—C7—H7	117.0
C1—O1—Ni1	127.5 (2)	N1—C8—C9	113.3 (3)
C7—N1—C8	117.5 (3)	N1—C8—H8A	108.9
C7—N1—Ni1	126.0 (3)	C9—C8—H8A	108.9
C8—N1—Ni1	115.5 (2)	N1—C8—H8B	108.9
O1—C1—C2	120.4 (3)	C9—C8—H8B	108.9
O1—C1—C6	124.4 (3)	H8A—C8—H8B	107.7
C2—C1—C6	115.3 (3)	C8—C9—C8i	110.2 (4)
C3—C2—C1	123.3 (3)	C8—C9—C10i	107.7 (2)
C3—C2—Br1	117.8 (3)	C8i—C9—C10i	111.3 (2)
C1—C2—Br1	118.8 (3)	C8—C9—C10	111.3 (2)
C2—C3—C4	119.2 (3)	C8i—C9—C10	107.7 (2)
C2—C3—H3	120.4	C10i—C9—C10	108.7 (5)
C4—C3—H3	120.4	C9—C10—H10A	109.5
C5—C4—C3	120.9 (3)	C9—C10—H10B	109.5
C5—C4—Br2	120.4 (3)	H10A—C10—H10B	109.5
C3—C4—Br2	118.7 (3)	C9—C10—H10C	109.5
C4—C5—C6	120.0 (4)	H10A—C10—H10C	109.5
C4—C5—H5	120.0	H10B—C10—H10C	109.5
C6—C5—H5	120.0
O1i—Ni1—O1—C1	−178.8 (3)	C2—C3—C4—Br2	−179.3 (3)
N1i—Ni1—O1—C1	95.7 (5)	C3—C4—C5—C6	0.5 (6)
N1—Ni1—O1—C1	−14.0 (3)	Br2—C4—C5—C6	179.8 (3)
O1—Ni1—N1—C7	6.6 (3)	C4—C5—C6—C1	−0.1 (5)
O1i—Ni1—N1—C7	90.8 (5)	C4—C5—C6—C7	175.9 (3)
N1i—Ni1—N1—C7	−159.1 (4)	O1—C1—C6—C5	178.0 (3)
O1—Ni1—N1—C8	−161.3 (2)	C2—C1—C6—C5	−0.9 (5)
O1i—Ni1—N1—C8	−77.1 (5)	O1—C1—C6—C7	2.2 (5)
N1i—Ni1—N1—C8	32.97 (18)	C2—C1—C6—C7	−176.7 (3)
Ni1—O1—C1—C2	−169.7 (2)	C8—N1—C7—C6	171.2 (3)
Ni1—O1—C1—C6	11.5 (5)	Ni1—N1—C7—C6	3.5 (5)
O1—C1—C2—C3	−177.4 (3)	C5—C6—C7—N1	174.0 (3)
C6—C1—C2—C3	1.5 (5)	C1—C6—C7—N1	−10.0 (6)
O1—C1—C2—Br1	3.1 (4)	C7—N1—C8—C9	118.4 (3)
C6—C1—C2—Br1	−177.9 (2)	Ni1—N1—C8—C9	−72.7 (3)
C1—C2—C3—C4	−1.1 (5)	N1—C8—C9—C8i	35.2 (2)
Br1—C2—C3—C4	178.3 (3)	N1—C8—C9—C10i	156.7 (3)
C2—C3—C4—C5	0.1 (6)	N1—C8—C9—C10	−84.3 (4)