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

In the title centrosymmetric mononuclear copper(II) complex, [Cu(C(8)H(7)BrNO(2))(2)], the Cu(II) atom, lying on an inversion centre, is four-coordinated in a trans-CuN(2)O(2) square-planar geometry by two phenolate O atoms and two oxime N atoms from two symmetry-related N,O-bidentate oxime-type ligands. Inter-molecular C-H⋯O hydrogen bonds link neighbouring mol-ecules into a one-dimensional supra-molecular structure with an R(2) (2)(14) ring motif. This structure is further stabilized by π-π stacking inter-actions between adjacent benzene rings [centroid-centroid distance = 3.862 (1) Å].

Related literature

For general background to oxime compounds, see: Chaudhuri (2003 ▶); Dong et al. (2007a ▶, 2008 ▶). For related structures, see: Dong et al. (2007b ▶, 2009 ▶). For the ligand synthesis, see: Wang et al. (2008 ▶); Zhao et al. (2009 ▶).

Experimental

Crystal data

[Cu(C8H7BrNO2)2]

M = 521.65

Monoclinic,

a = 24.691 (3) Å

b = 3.8623 (5) Å

c = 20.260 (2) Å

β = 117.453 (2)°

V = 1714.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 5.96 mm−1

T = 298 K

0.40 × 0.12 × 0.11 mm

Data collection

Siemens SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.199, T max = 0.560

3981 measured reflections

1521 independent reflections

1128 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.053

S = 1.04

1521 reflections

116 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.40 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 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047989/hy2253sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047989/hy2253Isup2.hkl

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

[Cu(C8H7BrNO2)2]	F(000) = 1020
Mr = 521.65	Dx = 2.021 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1233 reflections
a = 24.691 (3) Å	θ = 2.2–23.4°
b = 3.8623 (5) Å	µ = 5.96 mm−1
c = 20.260 (2) Å	T = 298 K
β = 117.453 (2)°	Needle-like, dark-brown
V = 1714.4 (3) Å3	0.40 × 0.12 × 0.11 mm
Z = 4

Siemens SMART 1000 CCD diffractometer	1521 independent reflections
Radiation source: fine-focus sealed tube	1128 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→28
Tmin = 0.199, Tmax = 0.560	k = −4→4
3981 measured reflections	l = −24→23

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.053	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0126P)2] where P = (Fo2 + 2Fc2)/3
1521 reflections	(Δ/σ)max < 0.001
116 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.5000	0.5000	0.5000	0.0478 (2)
Br1	0.169435 (18)	0.60817 (11)	0.35138 (2)	0.04703 (16)
N1	0.46014 (14)	0.4521 (8)	0.56593 (15)	0.0359 (8)
O1	0.48859 (12)	0.2994 (7)	0.63799 (13)	0.0454 (7)
O2	0.43631 (11)	0.8108 (7)	0.43906 (13)	0.0459 (8)
C1	0.54119 (19)	0.4966 (11)	0.6868 (2)	0.0563 (13)
H1A	0.5672	0.5306	0.6638	0.084*
H1B	0.5632	0.3737	0.7328	0.084*
H1C	0.5284	0.7173	0.6964	0.084*
C2	0.40218 (17)	0.4722 (9)	0.54291 (19)	0.0353 (10)
H2	0.3870	0.3956	0.5747	0.042*
C3	0.35910 (16)	0.6052 (9)	0.47123 (18)	0.0303 (9)
C4	0.37870 (17)	0.7699 (10)	0.42340 (19)	0.0337 (10)
C5	0.33223 (17)	0.9004 (10)	0.35507 (19)	0.0357 (10)
H5	0.3434	1.0184	0.3232	0.043*
C6	0.27127 (17)	0.8574 (9)	0.33473 (19)	0.0358 (10)
H6	0.2418	0.9423	0.2894	0.043*
C7	0.25404 (16)	0.6861 (9)	0.3825 (2)	0.0308 (9)
C8	0.29692 (16)	0.5679 (9)	0.45035 (19)	0.0323 (9)
H8	0.2847	0.4628	0.4826	0.039*

	U11	U22	U33	U12	U13	U23
Cu1	0.0365 (4)	0.0708 (6)	0.0413 (4)	0.0207 (4)	0.0224 (4)	0.0218 (4)
Br1	0.0330 (3)	0.0476 (3)	0.0530 (3)	−0.0031 (2)	0.0134 (2)	−0.0005 (2)
N1	0.035 (2)	0.044 (2)	0.0273 (18)	0.0067 (17)	0.0131 (15)	0.0089 (15)
O1	0.0378 (17)	0.057 (2)	0.0334 (15)	0.0074 (14)	0.0095 (13)	0.0140 (14)
O2	0.0311 (17)	0.064 (2)	0.0454 (16)	0.0148 (15)	0.0198 (13)	0.0245 (14)
C1	0.057 (3)	0.060 (3)	0.037 (2)	0.003 (2)	0.009 (2)	−0.001 (2)
C2	0.038 (3)	0.036 (3)	0.036 (2)	0.001 (2)	0.020 (2)	0.0039 (18)
C3	0.034 (2)	0.032 (2)	0.026 (2)	0.0051 (19)	0.0140 (18)	0.0016 (19)
C4	0.034 (2)	0.037 (2)	0.030 (2)	0.007 (2)	0.015 (2)	0.0004 (19)
C5	0.043 (3)	0.036 (2)	0.033 (2)	0.008 (2)	0.0216 (19)	0.004 (2)
C6	0.036 (3)	0.038 (3)	0.027 (2)	0.009 (2)	0.0097 (19)	0.003 (2)
C7	0.031 (2)	0.024 (2)	0.036 (2)	0.0008 (18)	0.0148 (19)	−0.0039 (18)
C8	0.039 (2)	0.032 (2)	0.034 (2)	0.000 (2)	0.0224 (19)	0.0001 (19)

Cu1—O2	1.910 (2)	C2—H2	0.9300
Cu1—N1	2.000 (3)	C3—C8	1.399 (5)
Br1—C7	1.907 (4)	C3—C4	1.418 (5)
N1—C2	1.287 (4)	C4—C5	1.422 (5)
N1—O1	1.424 (3)	C5—C6	1.375 (5)
O1—C1	1.435 (4)	C5—H5	0.9300
O2—C4	1.316 (4)	C6—C7	1.391 (5)
C1—H1A	0.9600	C6—H6	0.9300
C1—H1B	0.9600	C7—C8	1.370 (5)
C1—H1C	0.9600	C8—H8	0.9300
C2—C3	1.442 (5)
O2i—Cu1—O2	180.000 (2)	C3—C2—H2	117.7
O2i—Cu1—N1	91.27 (11)	C8—C3—C4	120.8 (3)
O2—Cu1—N1	88.73 (11)	C8—C3—C2	117.7 (3)
O2i—Cu1—N1i	88.73 (11)	C4—C3—C2	121.5 (3)
O2—Cu1—N1i	91.27 (11)	O2—C4—C3	124.1 (3)
N1—Cu1—N1i	180.000 (1)	O2—C4—C5	119.3 (3)
C2—N1—O1	109.7 (3)	C3—C4—C5	116.6 (3)
C2—N1—Cu1	124.0 (2)	C6—C5—C4	122.0 (4)
O1—N1—Cu1	124.1 (2)	C6—C5—H5	119.0
N1—O1—C1	110.4 (3)	C4—C5—H5	119.0
C4—O2—Cu1	123.8 (2)	C5—C6—C7	119.5 (3)
O1—C1—H1A	109.5	C5—C6—H6	120.2
O1—C1—H1B	109.5	C7—C6—H6	120.2
H1A—C1—H1B	109.5	C8—C7—C6	120.9 (4)
O1—C1—H1C	109.5	C8—C7—Br1	120.0 (3)
H1A—C1—H1C	109.5	C6—C7—Br1	119.0 (3)
H1B—C1—H1C	109.5	C7—C8—C3	120.1 (3)
N1—C2—C3	124.5 (3)	C7—C8—H8	120.0
N1—C2—H2	117.7	C3—C8—H8	120.0
O2i—Cu1—N1—C2	−148.5 (3)	C8—C3—C4—O2	−179.3 (3)
O2—Cu1—N1—C2	31.5 (3)	C2—C3—C4—O2	1.1 (6)
O2i—Cu1—N1—O1	13.2 (3)	C8—C3—C4—C5	1.5 (5)
O2—Cu1—N1—O1	−166.8 (3)	C2—C3—C4—C5	−178.1 (3)
C2—N1—O1—C1	−133.0 (3)	O2—C4—C5—C6	178.2 (3)
Cu1—N1—O1—C1	63.0 (3)	C3—C4—C5—C6	−2.6 (5)
N1—Cu1—O2—C4	−38.8 (3)	C4—C5—C6—C7	1.0 (6)
N1i—Cu1—O2—C4	141.2 (3)	C5—C6—C7—C8	1.8 (5)
O1—N1—C2—C3	−178.3 (3)	C5—C6—C7—Br1	−176.9 (3)
Cu1—N1—C2—C3	−14.3 (5)	C6—C7—C8—C3	−2.8 (5)
N1—C2—C3—C8	171.7 (3)	Br1—C7—C8—C3	175.9 (3)
N1—C2—C3—C4	−8.6 (6)	C4—C3—C8—C7	1.1 (5)
Cu1—O2—C4—C3	29.8 (5)	C2—C3—C8—C7	−179.2 (3)
Cu1—O2—C4—C5	−151.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···O1ii	0.96	2.52	3.328 (5)	142

Table 1

Selected bond lengths (Å)

Cu1—O2	1.910 (2)
Cu1—N1	2.000 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1C⋯O1i	0.96	2.52	3.328 (5)	142

Symmetry code: (i) .