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

In the title compound, [Cu(C(19)H(16)I(4)N(2)O(2))], the Cu(II) atom and the substituted C atom of the diamine segment lie on a crystallographic twofold rotation axis. The geometry around the Cu(II) atom is distorted square-planar, which is supported by the N(2)O(2) donor atoms of the coordinated Schiff base. The dihedral angle between the symmetry-related substituted benzene rings is 29.40 (19)°. In the crystal, a short I⋯I [3.8766 (6) Å] contact is present and links neighbouring mol-ecules into chains propagating along the a axis.

Related literature

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

Experimental

Crystal data

[Cu(C19H16I4N2O2)]

M = 875.48

Orthorhombic,

a = 16.9336 (10) Å

b = 15.9602 (12) Å

c = 8.7041 (5) Å

V = 2352.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 6.20 mm−1

T = 296 K

0.21 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.269, T max = 0.551

9807 measured reflections

2321 independent reflections

1791 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.059

S = 1.04

2321 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.94 e Å−3

Δρmin = −0.67 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/S1600536812020387/su2420sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020387/su2420Isup2.hkl

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

[Cu(C19H16I4N2O2)]	F(000) = 1604
Mr = 875.48	Dx = 2.472 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 1126 reflections
a = 16.9336 (10) Å	θ = 2.5–27.5°
b = 15.9602 (12) Å	µ = 6.20 mm−1
c = 8.7041 (5) Å	T = 296 K
V = 2352.4 (3) Å3	Block, red
Z = 4	0.21 × 0.12 × 0.08 mm

Bruker SMART APEXII CCD area-detector diffractometer	2321 independent reflections
Radiation source: fine-focus sealed tube	1791 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −20→20
Tmin = 0.269, Tmax = 0.551	k = −13→19
9807 measured reflections	l = −9→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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.021P)2 + 2.4697P] where P = (Fo2 + 2Fc2)/3
2321 reflections	(Δ/σ)max = 0.001
129 parameters	Δρmax = 0.94 e Å−3
0 restraints	Δρmin = −0.67 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
I1	0.16096 (2)	0.747572 (19)	0.30639 (4)	0.04900 (11)
I2	0.39828 (2)	0.53650 (3)	0.63814 (5)	0.06704 (14)
Cu1	0.0000	0.48949 (5)	0.2500	0.03357 (18)
O1	0.07523 (17)	0.57300 (18)	0.3038 (3)	0.0384 (7)
N1	0.0505 (2)	0.4038 (2)	0.3745 (4)	0.0348 (8)
C1	0.1415 (2)	0.5623 (3)	0.3769 (4)	0.0332 (10)
C2	0.1945 (3)	0.6301 (3)	0.3943 (4)	0.0350 (10)
C3	0.2653 (2)	0.6228 (3)	0.4678 (4)	0.0384 (11)
H3	0.2985	0.6691	0.4758	0.046*
C4	0.2882 (2)	0.5464 (3)	0.5306 (5)	0.0394 (10)
C5	0.2393 (3)	0.4793 (3)	0.5191 (5)	0.0417 (11)
H5	0.2547	0.4283	0.5613	0.050*
C6	0.1657 (2)	0.4854 (3)	0.4444 (5)	0.0348 (10)
C7	0.1168 (2)	0.4116 (3)	0.4443 (5)	0.0364 (10)
H7	0.1349	0.3656	0.4997	0.044*
C8	0.0045 (3)	0.3268 (3)	0.3955 (4)	0.0401 (10)
H8A	−0.0486	0.3416	0.4270	0.048*
H8B	0.0281	0.2941	0.4776	0.048*
C9	0.0000	0.2724 (4)	0.2500	0.0369 (14)
C10	−0.0730 (3)	0.2171 (3)	0.2632 (6)	0.0599 (14)
H10A	−0.0709	0.1862	0.3578	0.090*
H10B	−0.0745	0.1787	0.1783	0.090*
H10C	−0.1195	0.2515	0.2618	0.090*

	U11	U22	U33	U12	U13	U23
I1	0.0663 (2)	0.03097 (18)	0.04979 (18)	−0.00876 (16)	−0.00490 (15)	0.00638 (14)
I2	0.04541 (19)	0.0625 (3)	0.0932 (3)	0.00148 (19)	−0.02547 (19)	−0.0029 (2)
Cu1	0.0359 (4)	0.0272 (4)	0.0376 (4)	0.000	−0.0041 (3)	0.000
O1	0.0396 (16)	0.0278 (16)	0.0478 (17)	−0.0031 (14)	−0.0093 (14)	0.0029 (14)
N1	0.041 (2)	0.027 (2)	0.0359 (18)	−0.0058 (17)	−0.0016 (16)	0.0042 (16)
C1	0.037 (2)	0.032 (2)	0.031 (2)	−0.003 (2)	−0.0005 (18)	−0.0022 (19)
C2	0.042 (2)	0.028 (2)	0.035 (2)	−0.004 (2)	0.0031 (19)	0.0039 (19)
C3	0.038 (2)	0.037 (3)	0.041 (2)	−0.012 (2)	0.0025 (19)	−0.007 (2)
C4	0.033 (2)	0.041 (3)	0.045 (2)	−0.003 (2)	−0.002 (2)	−0.003 (2)
C5	0.045 (3)	0.037 (3)	0.043 (3)	0.003 (2)	−0.005 (2)	−0.001 (2)
C6	0.038 (2)	0.029 (2)	0.037 (2)	−0.0042 (19)	−0.0026 (19)	0.0021 (19)
C7	0.046 (3)	0.028 (2)	0.036 (2)	0.000 (2)	−0.002 (2)	0.0057 (19)
C8	0.048 (3)	0.035 (3)	0.036 (2)	−0.008 (2)	−0.0007 (19)	0.004 (2)
C9	0.041 (3)	0.024 (3)	0.045 (3)	0.000	−0.007 (3)	0.000
C10	0.063 (3)	0.050 (3)	0.066 (3)	−0.022 (3)	−0.006 (3)	−0.002 (3)

I1—C2	2.103 (4)	C4—C5	1.358 (6)
I2—C4	2.092 (4)	C5—C6	1.409 (6)
Cu1—O1	1.902 (3)	C5—H5	0.9300
Cu1—O1i	1.902 (3)	C6—C7	1.439 (6)
Cu1—N1i	1.944 (3)	C7—H7	0.9300
Cu1—N1	1.944 (3)	C8—C9	1.538 (5)
O1—C1	1.301 (5)	C8—H8A	0.9700
N1—C7	1.283 (5)	C8—H8B	0.9700
N1—C8	1.466 (5)	C9—C10	1.522 (6)
C1—C2	1.414 (6)	C9—C10i	1.522 (6)
C1—C6	1.422 (6)	C9—C8i	1.538 (5)
C2—C3	1.364 (6)	C10—H10A	0.9600
C3—C4	1.391 (6)	C10—H10B	0.9600
C3—H3	0.9300	C10—H10C	0.9600
O1—Cu1—O1i	91.04 (17)	C5—C6—C1	120.4 (4)
O1—Cu1—N1i	157.69 (13)	C5—C6—C7	116.9 (4)
O1i—Cu1—N1i	93.51 (13)	C1—C6—C7	122.7 (4)
O1—Cu1—N1	93.51 (13)	N1—C7—C6	125.7 (4)
O1i—Cu1—N1	157.69 (13)	N1—C7—H7	117.2
N1i—Cu1—N1	90.5 (2)	C6—C7—H7	117.2
C1—O1—Cu1	127.3 (3)	N1—C8—C9	113.4 (3)
C7—N1—C8	119.2 (4)	N1—C8—H8A	108.9
C7—N1—Cu1	125.5 (3)	C9—C8—H8A	108.9
C8—N1—Cu1	115.2 (3)	N1—C8—H8B	108.9
O1—C1—C2	120.0 (4)	C9—C8—H8B	108.9
O1—C1—C6	124.3 (4)	H8A—C8—H8B	107.7
C2—C1—C6	115.7 (4)	C10—C9—C10i	109.2 (6)
C3—C2—C1	122.9 (4)	C10—C9—C8	107.8 (3)
C3—C2—I1	119.0 (3)	C10i—C9—C8	110.4 (3)
C1—C2—I1	118.1 (3)	C10—C9—C8i	110.4 (3)
C2—C3—C4	120.2 (4)	C10i—C9—C8i	107.8 (3)
C2—C3—H3	119.9	C8—C9—C8i	111.2 (5)
C4—C3—H3	119.9	C9—C10—H10A	109.5
C5—C4—C3	119.6 (4)	C9—C10—H10B	109.5
C5—C4—I2	121.1 (3)	H10A—C10—H10B	109.5
C3—C4—I2	119.3 (3)	C9—C10—H10C	109.5
C4—C5—C6	121.3 (4)	H10A—C10—H10C	109.5
C4—C5—H5	119.4	H10B—C10—H10C	109.5
C6—C5—H5	119.4
O1i—Cu1—O1—C1	168.3 (4)	C2—C3—C4—I2	178.6 (3)
N1i—Cu1—O1—C1	−89.9 (5)	C3—C4—C5—C6	0.1 (7)
N1—Cu1—O1—C1	10.1 (3)	I2—C4—C5—C6	−178.9 (3)
O1—Cu1—N1—C7	−7.0 (4)	C4—C5—C6—C1	1.0 (6)
O1i—Cu1—N1—C7	−108.3 (4)	C4—C5—C6—C7	−177.3 (4)
N1i—Cu1—N1—C7	151.1 (4)	O1—C1—C6—C5	178.8 (4)
O1—Cu1—N1—C8	168.9 (3)	C2—C1—C6—C5	−1.6 (6)
O1i—Cu1—N1—C8	67.5 (5)	O1—C1—C6—C7	−3.0 (6)
N1i—Cu1—N1—C8	−33.1 (2)	C2—C1—C6—C7	176.6 (4)
Cu1—O1—C1—C2	173.7 (3)	C8—N1—C7—C6	−175.1 (4)
Cu1—O1—C1—C6	−6.8 (6)	Cu1—N1—C7—C6	0.5 (6)
O1—C1—C2—C3	−179.1 (4)	C5—C6—C7—N1	−175.5 (4)
C6—C1—C2—C3	1.3 (6)	C1—C6—C7—N1	6.2 (7)
O1—C1—C2—I1	2.2 (5)	C7—N1—C8—C9	−111.6 (4)
C6—C1—C2—I1	−177.3 (3)	Cu1—N1—C8—C9	72.3 (4)
C1—C2—C3—C4	−0.4 (6)	N1—C8—C9—C10	−157.0 (4)
I1—C2—C3—C4	178.3 (3)	N1—C8—C9—C10i	83.8 (5)
C2—C3—C4—C5	−0.4 (6)	N1—C8—C9—C8i	−35.9 (2)