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

The asymmetric unit of the title compound, [Ni(C(19)H(16)I(4)N(2)O(2))], comprises half of a Schiff base complex. The Ni(II) atom is located on a twofold rotation axis which also bis-ects the central C atom of the 2,2-dimethyl-propane group of the ligand. The geometry around the Ni(II) atom is distorted square-planar, with a dihedral angle of 21.7 (3)° between the symmetry-related N/Ni/O coordination planes. The dihedral angle between the symmetry-related benzene rings is 27.9 (3)°. In the crystal, short inter-molecular I⋯I [3.8178 (9) and 3.9013 (10) Å] inter-actions are present.

Related literature

For applications of Schiff bases in coordination chemistry, see: Granovski et al. (1993 ▶); Blower et al. (1998 ▶). For the related structures studied by our group, see: Kargar et al. (2012a ▶,b ▶,c ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

[Ni(C19H16I4N2O2)]

M = 870.65

Orthorhombic,

a = 16.682 (2) Å

b = 15.9978 (19) Å

c = 8.7920 (9) Å

V = 2346.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 6.11 mm−1

T = 291 K

0.21 × 0.15 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.360, T max = 0.553

10345 measured reflections

2582 independent reflections

1615 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.096

S = 0.96

2582 reflections

129 parameters

H-atom parameters constrained

Δρmax = 1.07 e Å−3

Δρmin = −0.73 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/S1600536812024944/su2444sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024944/su2444Isup2.hkl

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

[Ni(C19H16I4N2O2)]	F(000) = 1600
Mr = 870.65	Dx = 2.465 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2540 reflections
a = 16.682 (2) Å	θ = 2.5–27.4°
b = 15.9978 (19) Å	µ = 6.11 mm−1
c = 8.7920 (9) Å	T = 291 K
V = 2346.4 (5) Å3	Block, dark-red
Z = 4	0.21 × 0.15 × 0.11 mm

Bruker SMART APEXII CCD area-detector diffractometer	2582 independent reflections
Radiation source: fine-focus sealed tube	1615 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
φ and ω scans	θmax = 27.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −21→21
Tmin = 0.360, Tmax = 0.553	k = −20→18
10345 measured reflections	l = −11→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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0314P)2] where P = (Fo2 + 2Fc2)/3
2582 reflections	(Δ/σ)max = 0.001
129 parameters	Δρmax = 1.07 e Å−3
0 restraints	Δρmin = −0.73 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
C1	0.6358 (4)	−0.0602 (4)	0.1174 (7)	0.0299 (16)
C2	0.6886 (4)	−0.1295 (4)	0.1037 (7)	0.0362 (17)
C3	0.7615 (4)	−0.1247 (5)	0.0316 (7)	0.0397 (18)
H3	0.7938	−0.1719	0.0252	0.048*
C4	0.7876 (5)	−0.0496 (4)	−0.0323 (8)	0.0416 (18)
C5	0.7398 (5)	0.0202 (5)	−0.0212 (8)	0.0445 (19)
H5	0.7569	0.0706	−0.0629	0.053*
C6	0.6647 (4)	0.0157 (4)	0.0534 (7)	0.0319 (16)
C7	0.6152 (4)	0.0890 (4)	0.0576 (7)	0.0356 (17)
H7	0.6320	0.1342	−0.0009	0.043*
C8	0.5034 (5)	0.1751 (4)	0.1100 (7)	0.0389 (17)
H8A	0.4493	0.1598	0.0813	0.047*
H8B	0.5265	0.2066	0.0265	0.047*
C9	0.5000	0.2309 (5)	0.2500	0.038 (2)
C10	0.4250 (5)	0.2865 (5)	0.2380 (10)	0.062 (2)
H10A	0.3778	0.2522	0.2412	0.093*
H10B	0.4263	0.3168	0.1438	0.093*
H10C	0.4240	0.3252	0.3214	0.093*
I1	0.65256 (3)	−0.24569 (3)	0.19386 (5)	0.04569 (18)
I2	0.89983 (4)	−0.04176 (4)	−0.13554 (7)	0.0658 (2)
Ni1	0.5000	0.01657 (7)	0.2500	0.0310 (3)
N1	0.5506 (3)	0.0986 (3)	0.1332 (6)	0.0339 (13)
O1	0.5668 (3)	−0.0689 (3)	0.1835 (5)	0.0363 (11)

	U11	U22	U33	U12	U13	U23
C1	0.031 (4)	0.027 (4)	0.032 (4)	0.006 (3)	0.002 (3)	0.000 (3)
C2	0.041 (4)	0.028 (4)	0.039 (4)	0.007 (4)	0.002 (3)	0.002 (3)
C3	0.042 (5)	0.035 (4)	0.042 (4)	0.009 (4)	−0.008 (4)	−0.006 (3)
C4	0.044 (5)	0.032 (4)	0.049 (4)	0.003 (4)	0.006 (4)	−0.005 (3)
C5	0.053 (5)	0.042 (5)	0.039 (4)	−0.006 (4)	0.005 (4)	0.001 (3)
C6	0.035 (4)	0.023 (4)	0.038 (4)	−0.002 (3)	−0.001 (3)	0.007 (3)
C7	0.043 (5)	0.023 (4)	0.041 (4)	−0.002 (4)	0.004 (4)	0.007 (3)
C8	0.046 (5)	0.026 (4)	0.045 (4)	0.005 (4)	0.000 (4)	0.006 (3)
C9	0.054 (7)	0.012 (5)	0.049 (6)	0.000	0.006 (5)	0.000
C10	0.068 (6)	0.053 (5)	0.066 (5)	0.019 (5)	0.009 (5)	−0.004 (4)
I1	0.0588 (4)	0.0285 (3)	0.0498 (3)	0.0072 (3)	0.0027 (3)	0.0056 (2)
I2	0.0448 (4)	0.0558 (4)	0.0967 (5)	−0.0031 (3)	0.0273 (3)	−0.0059 (3)
Ni1	0.0323 (7)	0.0229 (7)	0.0378 (7)	0.000	0.0032 (6)	0.000
N1	0.038 (4)	0.021 (3)	0.043 (3)	0.008 (3)	0.005 (3)	−0.001 (2)
O1	0.035 (3)	0.025 (2)	0.049 (3)	0.005 (2)	0.013 (2)	0.002 (2)

C1—O1	1.297 (8)	C8—N1	1.469 (8)
C1—C2	1.422 (9)	C8—C9	1.521 (8)
C1—C6	1.423 (8)	C8—H8A	0.9700
C2—C3	1.374 (9)	C8—H8B	0.9700
C2—I1	2.108 (7)	C9—C8i	1.521 (8)
C3—C4	1.396 (9)	C9—C10i	1.540 (9)
C3—H3	0.9300	C9—C10	1.540 (9)
C4—C5	1.376 (10)	C10—H10A	0.9600
C4—I2	2.085 (8)	C10—H10B	0.9600
C5—C6	1.417 (10)	C10—H10C	0.9600
C5—H5	0.9300	Ni1—O1i	1.858 (4)
C6—C7	1.434 (9)	Ni1—O1	1.858 (4)
C7—N1	1.275 (8)	Ni1—N1	1.868 (5)
C7—H7	0.9300	Ni1—N1i	1.868 (5)
O1—C1—C2	120.3 (6)	C9—C8—H8B	108.9
O1—C1—C6	124.7 (6)	H8A—C8—H8B	107.7
C2—C1—C6	115.0 (6)	C8i—C9—C8	108.2 (7)
C3—C2—C1	123.0 (6)	C8i—C9—C10i	108.3 (4)
C3—C2—I1	118.4 (5)	C8—C9—C10i	111.3 (4)
C1—C2—I1	118.6 (5)	C8i—C9—C10	111.3 (4)
C2—C3—C4	120.7 (7)	C8—C9—C10	108.3 (4)
C2—C3—H3	119.7	C10i—C9—C10	109.4 (9)
C4—C3—H3	119.7	C9—C10—H10A	109.5
C5—C4—C3	119.4 (7)	C9—C10—H10B	109.5
C5—C4—I2	120.2 (5)	H10A—C10—H10B	109.5
C3—C4—I2	120.4 (5)	C9—C10—H10C	109.5
C4—C5—C6	120.3 (7)	H10A—C10—H10C	109.5
C4—C5—H5	119.9	H10B—C10—H10C	109.5
C6—C5—H5	119.9	O1i—Ni1—O1	85.2 (3)
C5—C6—C1	121.8 (6)	O1i—Ni1—N1	163.9 (2)
C5—C6—C7	118.6 (6)	O1—Ni1—N1	94.2 (2)
C1—C6—C7	119.5 (6)	O1i—Ni1—N1i	94.2 (2)
N1—C7—C6	126.7 (6)	O1—Ni1—N1i	163.9 (2)
N1—C7—H7	116.6	N1—Ni1—N1i	90.7 (3)
C6—C7—H7	116.6	C7—N1—C8	118.7 (6)
N1—C8—C9	113.3 (5)	C7—N1—Ni1	125.7 (5)
N1—C8—H8A	108.9	C8—N1—Ni1	114.8 (4)
C9—C8—H8A	108.9	C1—O1—Ni1	126.5 (4)
N1—C8—H8B	108.9
O1—C1—C2—C3	178.3 (6)	N1—C8—C9—C8i	−36.1 (4)
C6—C1—C2—C3	−1.2 (10)	N1—C8—C9—C10i	82.8 (7)
O1—C1—C2—I1	−0.4 (8)	N1—C8—C9—C10	−157.0 (6)
C6—C1—C2—I1	−179.9 (5)	C6—C7—N1—C8	−173.4 (6)
C1—C2—C3—C4	0.3 (11)	C6—C7—N1—Ni1	−4.0 (10)
I1—C2—C3—C4	178.9 (5)	C9—C8—N1—C7	−114.5 (7)
C2—C3—C4—C5	0.6 (11)	C9—C8—N1—Ni1	75.0 (6)
C2—C3—C4—I2	178.1 (5)	O1i—Ni1—N1—C7	−95.4 (9)
C3—C4—C5—C6	−0.4 (11)	O1—Ni1—N1—C7	−8.0 (6)
I2—C4—C5—C6	−177.9 (5)	N1i—Ni1—N1—C7	156.7 (7)
C4—C5—C6—C1	−0.7 (11)	O1i—Ni1—N1—C8	74.4 (9)
C4—C5—C6—C7	−177.7 (6)	O1—Ni1—N1—C8	161.7 (4)
O1—C1—C6—C5	−178.1 (6)	N1i—Ni1—N1—C8	−33.6 (3)
C2—C1—C6—C5	1.4 (9)	C2—C1—O1—Ni1	165.6 (5)
O1—C1—C6—C7	−1.1 (10)	C6—C1—O1—Ni1	−14.9 (9)
C2—C1—C6—C7	178.4 (6)	O1i—Ni1—O1—C1	−178.8 (6)
C5—C6—C7—N1	−171.8 (7)	N1—Ni1—O1—C1	17.2 (6)
C1—C6—C7—N1	11.1 (11)	N1i—Ni1—O1—C1	−90.2 (9)