Bis[(E)-4-bromo-2-(ethoxy-imino-meth-yl)phenolato-κN,O]copper(II).

The title compound, [Cu(C(9)H(9)BrNO(2))(2)], is a centrosymmetric mononuclear copper(II) complex. The Cu atom is four-coordinated in a trans-CuN(2)O(2) square-planar geometry by two phenolate O and two oxime N atoms from two symmetry-related N,O-bidentate (E)-4-bromo-2-(ethoxy-imino-meth-yl)phenolate oxime-type ligands. An inter-esting feature of the crystal structure is the centrosymmetric inter-molecular Cu⋯O inter-action [3.382 (1) Å], which establishes an infinite chain structure along the b axis.

Related literature

For background to oximes, see: Cervera et al. (1997 ▶); Chaudhuri, (2003 ▶); Costes et al. (1998 ▶); Kukushkin et al. (1996 ▶). For related structures, see: Dong et al. (2009 ▶). For the synthesis, see: Wang et al. (2008 ▶); Zhao et al. (2009 ▶).

Experimental

Crystal data

[Cu(C9H9BrNO2)2]

M = 549.70

Monoclinic,

a = 10.0682 (13) Å

b = 5.4998 (8) Å

c = 17.990 (2) Å

β = 96.846 (1)°

V = 989.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 5.17 mm−1

T = 298 K

0.41 × 0.21 × 0.14 mm

Data collection

Bruker SMART 1000 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.226, T max = 0.531

4684 measured reflections

1741 independent reflections

1356 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.080

S = 1.01

1741 reflections

125 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.55 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904433X/om2289sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904433X/om2289Isup2.hkl

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

[Cu(C9H9BrNO2)2]	F(000) = 542
Mr = 549.70	Dx = 1.846 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1900 reflections
a = 10.0682 (13) Å	θ = 2.2–25.1°
b = 5.4998 (8) Å	µ = 5.17 mm−1
c = 17.990 (2) Å	T = 298 K
β = 96.846 (1)°	Needle-shaped, black
V = 989.1 (2) Å3	0.41 × 0.21 × 0.14 mm
Z = 2

Bruker SMART 1000 diffractometer	1741 independent reflections
Radiation source: fine-focus sealed tube	1356 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→7
Tmin = 0.226, Tmax = 0.531	k = −6→6
4684 measured reflections	l = −21→21

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0416P)2 + 0.0351P] where P = (Fo2 + 2Fc2)/3
1741 reflections	(Δ/σ)max < 0.001
125 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.55 e Å−3

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	0.5000	0.5000	0.04220 (19)
Br1	−0.06756 (4)	0.09316 (8)	0.22617 (2)	0.06250 (18)
N1	0.5039 (2)	0.2157 (5)	0.43148 (14)	0.0399 (6)
O1	0.3323 (2)	0.5904 (4)	0.45038 (14)	0.0573 (7)
O2	0.6088 (2)	0.0414 (4)	0.44170 (12)	0.0463 (6)
C1	0.4064 (3)	0.1341 (6)	0.38559 (17)	0.0408 (8)
H1	0.4186	−0.0143	0.3625	0.049*
C2	0.2803 (3)	0.2546 (6)	0.36725 (16)	0.0374 (7)
C3	0.2497 (3)	0.4733 (6)	0.40143 (19)	0.0441 (8)
C4	0.1206 (3)	0.5724 (7)	0.3809 (2)	0.0550 (10)
H4	0.0977	0.7171	0.4029	0.066*
C5	0.0289 (3)	0.4618 (7)	0.3298 (2)	0.0508 (9)
H5	−0.0552	0.5307	0.3176	0.061*
C6	0.0613 (3)	0.2477 (6)	0.29645 (18)	0.0420 (8)
C7	0.1851 (3)	0.1453 (6)	0.31422 (18)	0.0439 (8)
H7	0.2062	0.0018	0.2909	0.053*
C8	0.7242 (3)	0.1298 (7)	0.4114 (2)	0.0545 (10)
H8A	0.7488	0.2894	0.4315	0.065*
H8B	0.7070	0.1416	0.3573	0.065*
C9	0.8336 (4)	−0.0500 (8)	0.4337 (2)	0.0677 (12)
H9A	0.8477	−0.0626	0.4873	0.102*
H9B	0.9146	0.0034	0.4156	0.102*
H9C	0.8085	−0.2061	0.4126	0.102*

	U11	U22	U33	U12	U13	U23
Cu1	0.0333 (3)	0.0474 (4)	0.0453 (4)	0.0111 (3)	0.0021 (2)	−0.0040 (3)
Br1	0.0549 (3)	0.0701 (3)	0.0589 (3)	−0.00385 (19)	−0.00800 (18)	−0.00911 (19)
N1	0.0340 (14)	0.0437 (17)	0.0429 (16)	0.0140 (12)	0.0079 (12)	0.0043 (13)
O1	0.0416 (13)	0.0519 (16)	0.0738 (17)	0.0155 (11)	−0.0115 (12)	−0.0206 (13)
O2	0.0385 (12)	0.0467 (14)	0.0542 (14)	0.0163 (11)	0.0083 (10)	0.0033 (11)
C1	0.0415 (18)	0.040 (2)	0.0425 (19)	0.0084 (15)	0.0117 (15)	−0.0025 (15)
C2	0.0345 (16)	0.042 (2)	0.0368 (18)	0.0042 (14)	0.0067 (13)	0.0007 (14)
C3	0.0372 (18)	0.045 (2)	0.050 (2)	0.0038 (16)	0.0046 (15)	−0.0013 (17)
C4	0.0411 (19)	0.050 (2)	0.070 (3)	0.0150 (17)	−0.0076 (17)	−0.0134 (19)
C5	0.0367 (18)	0.050 (2)	0.064 (2)	0.0097 (16)	−0.0010 (16)	−0.0011 (19)
C6	0.0356 (17)	0.051 (2)	0.0390 (18)	−0.0034 (15)	0.0003 (14)	0.0010 (16)
C7	0.049 (2)	0.043 (2)	0.0414 (19)	0.0039 (16)	0.0126 (16)	−0.0029 (16)
C8	0.0437 (19)	0.069 (3)	0.053 (2)	0.0164 (18)	0.0150 (17)	0.0045 (19)
C9	0.045 (2)	0.081 (3)	0.079 (3)	0.025 (2)	0.016 (2)	0.013 (2)

Cu1—O1i	1.880 (2)	C3—C4	1.417 (4)
Cu1—O1	1.880 (2)	C4—C5	1.366 (5)
Cu1—N1i	1.994 (3)	C4—H4	0.9300
Cu1—N1	1.994 (3)	C5—C6	1.378 (5)
Br1—C6	1.901 (3)	C5—H5	0.9300
N1—C1	1.285 (4)	C6—C7	1.370 (4)
N1—O2	1.422 (3)	C7—H7	0.9300
O1—C3	1.307 (4)	C8—C9	1.499 (5)
O2—C8	1.427 (4)	C8—H8A	0.9700
C1—C2	1.435 (4)	C8—H8B	0.9700
C1—H1	0.9300	C9—H9A	0.9600
C2—C3	1.402 (4)	C9—H9B	0.9600
C2—C7	1.405 (4)	C9—H9C	0.9600
O1i—Cu1—O1	180.000 (1)	C3—C4—H4	119.0
O1i—Cu1—N1i	89.80 (10)	C4—C5—C6	119.8 (3)
O1—Cu1—N1i	90.20 (10)	C4—C5—H5	120.1
O1i—Cu1—N1	90.20 (10)	C6—C5—H5	120.1
O1—Cu1—N1	89.80 (10)	C7—C6—C5	120.4 (3)
N1i—Cu1—N1	180.0	C7—C6—Br1	120.0 (3)
C1—N1—O2	110.2 (2)	C5—C6—Br1	119.6 (2)
C1—N1—Cu1	127.0 (2)	C6—C7—C2	120.7 (3)
O2—N1—Cu1	121.18 (18)	C6—C7—H7	119.6
C3—O1—Cu1	130.8 (2)	C2—C7—H7	119.6
N1—O2—C8	110.3 (2)	O2—C8—C9	106.1 (3)
N1—C1—C2	125.0 (3)	O2—C8—H8A	110.5
N1—C1—H1	117.5	C9—C8—H8A	110.5
C2—C1—H1	117.5	O2—C8—H8B	110.5
C3—C2—C7	119.8 (3)	C9—C8—H8B	110.5
C3—C2—C1	122.0 (3)	H8A—C8—H8B	108.7
C7—C2—C1	118.2 (3)	C8—C9—H9A	109.5
O1—C3—C2	124.3 (3)	C8—C9—H9B	109.5
O1—C3—C4	118.4 (3)	H9A—C9—H9B	109.5
C2—C3—C4	117.3 (3)	C8—C9—H9C	109.5
C5—C4—C3	122.0 (3)	H9A—C9—H9C	109.5
C5—C4—H4	119.0	H9B—C9—H9C	109.5
O1i—Cu1—N1—C1	168.7 (3)	C7—C2—C3—O1	−178.8 (3)
O1—Cu1—N1—C1	−11.3 (3)	C1—C2—C3—O1	2.3 (5)
O1i—Cu1—N1—O2	4.8 (2)	C7—C2—C3—C4	0.9 (5)
O1—Cu1—N1—O2	−175.2 (2)	C1—C2—C3—C4	−178.0 (3)
N1i—Cu1—O1—C3	−168.8 (3)	O1—C3—C4—C5	179.6 (3)
N1—Cu1—O1—C3	11.2 (3)	C2—C3—C4—C5	−0.2 (6)
C1—N1—O2—C8	113.3 (3)	C3—C4—C5—C6	−0.2 (6)
Cu1—N1—O2—C8	−80.4 (3)	C4—C5—C6—C7	0.0 (5)
O2—N1—C1—C2	174.8 (3)	C4—C5—C6—Br1	179.3 (3)
Cu1—N1—C1—C2	9.4 (5)	C5—C6—C7—C2	0.7 (5)
N1—C1—C2—C3	−2.9 (5)	Br1—C6—C7—C2	−178.6 (2)
N1—C1—C2—C7	178.1 (3)	C3—C2—C7—C6	−1.2 (5)
Cu1—O1—C3—C2	−9.0 (5)	C1—C2—C7—C6	177.7 (3)
Cu1—O1—C3—C4	171.2 (3)	N1—O2—C8—C9	172.7 (3)