Bis(2,4-dibromo-6-formyl-phenolato-κO,O')copper(II).

In the title compound, [Cu(C(7)H(3)Br(2)O(2))(2)], the Cu(II) atom, which lies on an inversion centre, is coordinated by four O atoms from two chelating bidentate 2,4-dibromo-6-formyl-phenolate ligands in a slightly distorted square-planar coordination geometry. In the crystal structure, short inter-molecular Br⋯Br [3.516 (4) and 3.653 (4) Å] and Cu⋯Br [3.255 (1) Å] contacts together with C-H⋯O hydrogen bonds generate a three-dimensional network.

Related literature

The presence of halo substituents on aromatic compounds frequently results in stacking arrangements with a short (ca 4 Å) crystallographic axis (Cohen et al., 1964 ▶; Zordan et al., 2005 ▶; Zaman et al., 2004 ▶; Zhang et al., 2007 ▶).

Experimental

Crystal data

[Cu(C7H3Br2O2)2]

M = 621.37

Orthorhombic,

a = 8.2625 (12) Å

b = 12.8216 (14) Å

c = 15.229 (2) Å

V = 1613.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 11.28 mm−1

T = 298 (2) K

0.58 × 0.18 × 0.14 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.059, T max = 0.301 (expected range = 0.040–0.206)

6267 measured reflections

1418 independent reflections

1049 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.069

S = 1.02

1418 reflections

106 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.40 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062769/sj2447sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062769/sj2447Isup2.hkl

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

[Cu(C7H3Br2O2)2]	F000 = 1164
Mr = 621.37	Dx = 2.558 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2295 reflections
a = 8.2625 (12) Å	θ = 2.7–26.8º
b = 12.8216 (14) Å	µ = 11.28 mm−1
c = 15.229 (2) Å	T = 298 (2) K
V = 1613.3 (4) Å3	Block, green
Z = 4	0.58 × 0.18 × 0.14 mm

Bruker SMART 1K CCD area-detector diffractometer	1418 independent reflections
Radiation source: fine-focus sealed tube	1049 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.058
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 2002)	h = −9→9
Tmin = 0.059, Tmax = 0.301	k = −15→14
6267 measured reflections	l = −10→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H-atom parameters constrained
wR(F2) = 0.069	w = 1/[σ2(Fo2) + (0.0306P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
1418 reflections	Δρmax = 0.64 e Å−3
106 parameters	Δρmin = −0.40 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Cu1	0.5000	1.0000	0.0000	0.0343 (2)
O1	0.3788 (4)	1.1291 (2)	−0.0202 (2)	0.0401 (9)
O2	0.3351 (3)	0.9426 (2)	0.0713 (2)	0.0353 (8)
Br1	0.15473 (6)	0.79703 (4)	0.19008 (4)	0.04386 (18)
Br2	−0.32171 (5)	1.11175 (5)	0.16575 (4)	0.04679 (19)
C1	0.2415 (6)	1.1486 (3)	0.0101 (3)	0.0387 (12)
H1	0.1983	1.2133	−0.0044	0.046*
C2	0.1438 (5)	1.0839 (3)	0.0638 (3)	0.0290 (11)
C3	0.1976 (5)	0.9837 (3)	0.0916 (3)	0.0259 (11)
C4	0.0877 (5)	0.9270 (3)	0.1451 (3)	0.0277 (11)
C5	−0.0614 (5)	0.9652 (4)	0.1676 (3)	0.0323 (12)
H5	−0.1302	0.9262	0.2031	0.039*
C6	−0.1097 (5)	1.0627 (4)	0.1372 (3)	0.0318 (11)
C7	−0.0094 (5)	1.1223 (3)	0.0878 (3)	0.0301 (11)
H7	−0.0418	1.1884	0.0698	0.036*

	U11	U22	U33	U12	U13	U23
Cu1	0.0233 (4)	0.0325 (5)	0.0469 (6)	−0.0004 (4)	0.0076 (4)	0.0068 (4)
O1	0.0293 (18)	0.0369 (19)	0.054 (2)	0.0031 (15)	0.0131 (16)	0.0149 (17)
O2	0.0215 (16)	0.0349 (18)	0.049 (2)	0.0036 (14)	0.0069 (16)	0.0080 (16)
Br1	0.0395 (3)	0.0338 (3)	0.0583 (4)	−0.0038 (2)	0.0016 (3)	0.0118 (3)
Br2	0.0286 (3)	0.0583 (4)	0.0534 (4)	0.0058 (3)	0.0100 (2)	−0.0060 (3)
C1	0.033 (3)	0.033 (3)	0.050 (3)	0.001 (2)	−0.001 (3)	0.010 (3)
C2	0.025 (2)	0.032 (3)	0.030 (3)	−0.004 (2)	0.003 (2)	0.000 (2)
C3	0.023 (2)	0.027 (3)	0.028 (3)	−0.0062 (19)	−0.003 (2)	0.000 (2)
C4	0.025 (2)	0.027 (2)	0.030 (3)	−0.006 (2)	−0.006 (2)	0.002 (2)
C5	0.029 (3)	0.037 (3)	0.031 (3)	−0.010 (2)	0.007 (2)	−0.001 (2)
C6	0.021 (2)	0.039 (3)	0.035 (3)	0.000 (2)	0.003 (2)	−0.005 (2)
C7	0.026 (2)	0.030 (3)	0.035 (3)	0.005 (2)	0.000 (2)	−0.001 (2)

Cu1—O2	1.892 (3)	C1—H1	0.9300
Cu1—O2i	1.892 (3)	C2—C7	1.407 (5)
Cu1—O1i	1.959 (3)	C2—C3	1.424 (6)
Cu1—O1	1.959 (3)	C3—C4	1.420 (6)
O1—C1	1.249 (5)	C4—C5	1.370 (6)
O2—C3	1.290 (5)	C5—C6	1.391 (6)
Br1—C4	1.885 (4)	C5—H5	0.9300
Br2—C6	1.912 (4)	C6—C7	1.355 (6)
C1—C2	1.418 (6)	C7—H7	0.9300
O2—Cu1—O2i	180.0	O2—C3—C2	124.9 (4)
O2—Cu1—O1i	87.09 (12)	C4—C3—C2	115.6 (4)
O2i—Cu1—O1i	92.91 (12)	C5—C4—C3	122.4 (4)
O2—Cu1—O1	92.91 (12)	C5—C4—Br1	119.3 (3)
O2i—Cu1—O1	87.09 (12)	C3—C4—Br1	118.2 (3)
O1i—Cu1—O1	180.000 (1)	C4—C5—C6	119.7 (4)
C1—O1—Cu1	125.1 (3)	C4—C5—H5	120.1
C3—O2—Cu1	127.8 (3)	C6—C5—H5	120.1
O1—C1—C2	127.8 (4)	C7—C6—C5	121.1 (4)
O1—C1—H1	116.1	C7—C6—Br2	120.1 (3)
C2—C1—H1	116.1	C5—C6—Br2	118.9 (3)
C7—C2—C1	117.3 (4)	C6—C7—C2	119.8 (4)
C7—C2—C3	121.3 (4)	C6—C7—H7	120.1
C1—C2—C3	121.4 (4)	C2—C7—H7	120.1
O2—C3—C4	119.5 (4)
O2—Cu1—O1—C1	−0.4 (4)	C1—C2—C3—C4	−179.9 (4)
O2i—Cu1—O1—C1	179.6 (4)	O2—C3—C4—C5	−178.7 (4)
O1i—Cu1—O1—C1	125 (100)	C2—C3—C4—C5	0.8 (6)
O2i—Cu1—O2—C3	−37.4 (17)	O2—C3—C4—Br1	4.0 (6)
O1i—Cu1—O2—C3	−179.0 (4)	C2—C3—C4—Br1	−176.5 (3)
O1—Cu1—O2—C3	1.0 (4)	C3—C4—C5—C6	0.4 (7)
Cu1—O1—C1—C2	−0.5 (7)	Br1—C4—C5—C6	177.8 (4)
O1—C1—C2—C7	−178.3 (4)	C4—C5—C6—C7	−2.1 (7)
O1—C1—C2—C3	1.1 (8)	C4—C5—C6—Br2	177.5 (3)
Cu1—O2—C3—C4	178.7 (3)	C5—C6—C7—C2	2.5 (7)
Cu1—O2—C3—C2	−0.7 (6)	Br2—C6—C7—C2	−177.2 (3)
C7—C2—C3—O2	179.0 (4)	C1—C2—C7—C6	178.3 (4)
C1—C2—C3—O2	−0.4 (7)	C3—C2—C7—C6	−1.1 (7)
C7—C2—C3—C4	−0.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···01ii	0.93	2.54	3.475 (5)	178

Cu1—O2	1.892 (3)
Cu1—O1	1.959 (3)

O2—Cu1—O2i	180
O2—Cu1—O1i	87.09 (12)
O2—Cu1—O1	92.91 (12)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯01ii	0.93	2.54	3.475 (5)	178

Symmetry code: (ii) .