Bis{6-bromo-4-chloro-2-[(E)-(2-chloro-phenyl)-imino-meth-yl]-phenolato-κ(2)N,O}copper(II).

In the title compound, [Cu(C(13)H(7)BrCl(2)NO)(2)], or CuL(2) {where HL= 2-[(E)-(2-chloro-phenyl-imino)-meth-yl]-6-bromo-4-chloro-phenol}, the Cu(II) atom is located on an inversion center and has a square-planar coordination. In the crystal, complex mol-ecules are linked via Cu⋯Cl inter-actions [2.9933 (11) Å], forming a two-dimensional network parallel to the bc plane. They are also Cl⋯Cl inter-actions [3.3709 (14) Å] present, which consolidate the two-dimensional network structure.

Related literature

For applications and properties of bidentate Schiff base ligands and their metal complexes, see: Akine et al. (2002 ▶); Schuetz et al. (2004 ▶); Singh et al. (1997 ▶); Qi et al. (2007 ▶).

Experimental

Crystal data

[Cu(C13H7BrCl2NO)2]

M = 751.55

Monoclinic,

a = 11.064 (3) Å

b = 9.437 (2) Å

c = 13.277 (4) Å

β = 108.997 (3)°

V = 1310.8 (6) Å3

Z = 2

Mo Kα radiation

μ = 4.32 mm−1

T = 153 K

0.46 × 0.42 × 0.42 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.242, T max = 0.265

10994 measured reflections

3491 independent reflections

2777 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.065

S = 1.00

3491 reflections

169 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.49 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 datablock(s) I, global. DOI: 10.1107/S1600536812025044/su2417sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025044/su2417Isup2.hkl

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

[Cu(C13H7BrCl2NO)2]	F(000) = 734
Mr = 751.55	Dx = 1.904 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4339 reflections
a = 11.064 (3) Å	θ = 2.1–29.1°
b = 9.437 (2) Å	µ = 4.32 mm−1
c = 13.277 (4) Å	T = 153 K
β = 108.997 (3)°	Block, green
V = 1310.8 (6) Å3	0.46 × 0.42 × 0.42 mm
Z = 2

Rigaku AFC10/Saturn724+ diffractometer	3491 independent reflections
Radiation source: Rotating Anode	2777 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 28.5714 pixels mm-1	θmax = 29.1°, θmin = 2.7°
phi and ω scans	h = −13→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −9→12
Tmin = 0.242, Tmax = 0.265	l = −18→18
10994 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.031P)2 + 0.160P] where P = (Fo2 + 2Fc2)/3
3491 reflections	(Δ/σ)max = 0.001
169 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
Br1	0.84869 (2)	0.57837 (3)	0.82867 (2)	0.0231 (1)
Cu1	0.50000	0.50000	0.50000	0.0154 (1)
Cl1	0.56447 (5)	0.30682 (6)	1.04373 (4)	0.0204 (2)
Cl2	−0.17769 (6)	0.39010 (9)	0.25396 (6)	0.0444 (2)
O1	0.60785 (15)	0.52907 (17)	0.64325 (12)	0.0175 (5)
N1	0.35254 (17)	0.4484 (2)	0.54915 (14)	0.0159 (5)
C1	0.5950 (2)	0.4776 (2)	0.73017 (17)	0.0148 (6)
C2	0.6964 (2)	0.4879 (2)	0.82837 (18)	0.0170 (7)
C3	0.6887 (2)	0.4339 (2)	0.92251 (17)	0.0178 (6)
C4	0.5768 (2)	0.3680 (2)	0.92269 (17)	0.0178 (7)
C5	0.4741 (2)	0.3556 (2)	0.83107 (17)	0.0180 (7)
C6	0.4826 (2)	0.4100 (2)	0.73471 (17)	0.0165 (7)
C7	0.3676 (2)	0.4035 (2)	0.64418 (18)	0.0177 (7)
C8	0.2249 (2)	0.4343 (2)	0.47615 (17)	0.0175 (6)
C9	0.1727 (2)	0.3013 (3)	0.44708 (18)	0.0218 (7)
C10	0.0474 (2)	0.2874 (3)	0.38026 (19)	0.0254 (8)
C11	−0.0229 (2)	0.4077 (3)	0.34322 (19)	0.0247 (7)
C12	0.0273 (2)	0.5410 (3)	0.3717 (2)	0.0263 (8)
C13	0.1522 (2)	0.5547 (3)	0.43829 (19)	0.0219 (7)
H3	0.75910	0.44180	0.98640	0.0210*
H5	0.39790	0.31070	0.83260	0.0220*
H7	0.29510	0.36170	0.65570	0.0210*
H9	0.22280	0.21920	0.47300	0.0260*
H10	0.01090	0.19630	0.36050	0.0300*
H12	−0.02350	0.62270	0.34580	0.0320*
H13	0.18810	0.64610	0.45800	0.0260*

	U11	U22	U33	U12	U13	U23
Br1	0.0173 (1)	0.0301 (2)	0.0214 (1)	−0.0056 (1)	0.0054 (1)	−0.0027 (1)
Cu1	0.0132 (2)	0.0197 (2)	0.0126 (2)	−0.0016 (2)	0.0033 (1)	0.0003 (2)
Cl1	0.0253 (3)	0.0211 (3)	0.0134 (2)	−0.0044 (2)	0.0045 (2)	0.0031 (2)
Cl2	0.0161 (3)	0.0692 (5)	0.0384 (4)	−0.0005 (3)	−0.0041 (3)	−0.0151 (4)
O1	0.0160 (8)	0.0240 (9)	0.0119 (7)	−0.0035 (7)	0.0038 (6)	0.0001 (6)
N1	0.0124 (9)	0.0185 (10)	0.0163 (9)	−0.0004 (7)	0.0041 (7)	0.0005 (7)
C1	0.0163 (10)	0.0123 (11)	0.0157 (11)	0.0000 (8)	0.0051 (9)	−0.0008 (8)
C2	0.0168 (11)	0.0155 (12)	0.0187 (11)	−0.0007 (9)	0.0056 (9)	−0.0023 (9)
C3	0.0176 (11)	0.0172 (12)	0.0156 (10)	0.0007 (9)	0.0015 (9)	−0.0011 (9)
C4	0.0221 (12)	0.0156 (12)	0.0148 (10)	0.0007 (9)	0.0047 (9)	0.0013 (9)
C5	0.0187 (11)	0.0179 (12)	0.0168 (11)	−0.0023 (9)	0.0051 (9)	0.0004 (9)
C6	0.0161 (11)	0.0169 (12)	0.0149 (11)	0.0004 (9)	0.0029 (9)	0.0001 (8)
C7	0.0166 (11)	0.0181 (12)	0.0183 (11)	−0.0019 (9)	0.0056 (9)	−0.0006 (9)
C8	0.0139 (10)	0.0251 (13)	0.0140 (10)	−0.0019 (9)	0.0052 (9)	0.0000 (9)
C9	0.0199 (12)	0.0233 (13)	0.0204 (12)	−0.0033 (10)	0.0040 (10)	0.0019 (9)
C10	0.0246 (13)	0.0267 (14)	0.0237 (12)	−0.0097 (11)	0.0062 (10)	−0.0032 (10)
C11	0.0114 (11)	0.0438 (16)	0.0174 (11)	−0.0013 (10)	0.0027 (9)	−0.0051 (10)
C12	0.0179 (12)	0.0345 (15)	0.0250 (13)	0.0084 (11)	0.0050 (10)	−0.0012 (11)
C13	0.0203 (12)	0.0219 (13)	0.0232 (12)	0.0004 (10)	0.0066 (10)	0.0000 (10)

Br1—C2	1.888 (2)	C4—C5	1.373 (3)
Cu1—O1	1.9076 (16)	C5—C6	1.410 (3)
Cu1—N1	2.005 (2)	C6—C7	1.439 (3)
Cu1—Cl1i	2.9933 (11)	C8—C9	1.383 (3)
Cu1—O1ii	1.9076 (16)	C8—C13	1.388 (3)
Cu1—N1ii	2.005 (2)	C9—C10	1.388 (3)
Cu1—Cl1iii	2.9933 (11)	C10—C11	1.374 (4)
Cl1—C4	1.754 (2)	C11—C12	1.377 (4)
Cl2—C11	1.745 (3)	C12—C13	1.383 (3)
O1—C1	1.302 (3)	C3—H3	0.9500
N1—C7	1.289 (3)	C5—H5	0.9500
N1—C8	1.435 (3)	C7—H7	0.9500
C1—C2	1.420 (3)	C9—H9	0.9500
C1—C6	1.416 (3)	C10—H10	0.9500
C2—C3	1.378 (3)	C12—H12	0.9500
C3—C4	1.386 (3)	C13—H13	0.9500
O1—Cu1—N1	91.24 (7)	C4—C5—C6	119.5 (2)
Cl1i—Cu1—O1	94.96 (5)	C1—C6—C5	121.4 (2)
O1—Cu1—O1ii	180.00	C1—C6—C7	122.24 (19)
O1—Cu1—N1ii	88.76 (7)	C5—C6—C7	116.1 (2)
Cl1iii—Cu1—O1	85.04 (5)	N1—C7—C6	126.9 (2)
Cl1i—Cu1—N1	97.49 (6)	N1—C8—C9	120.15 (19)
O1ii—Cu1—N1	88.76 (7)	N1—C8—C13	119.69 (19)
N1—Cu1—N1ii	180.00	C9—C8—C13	120.1 (2)
Cl1iii—Cu1—N1	82.51 (6)	C8—C9—C10	120.3 (2)
Cl1i—Cu1—O1ii	85.04 (5)	C9—C10—C11	118.8 (3)
Cl1i—Cu1—N1ii	82.51 (6)	Cl2—C11—C10	118.7 (2)
Cl1i—Cu1—Cl1iii	180.00	Cl2—C11—C12	119.5 (2)
O1ii—Cu1—N1ii	91.24 (7)	C10—C11—C12	121.7 (2)
Cl1iii—Cu1—O1ii	94.96 (5)	C11—C12—C13	119.4 (2)
Cl1iii—Cu1—N1ii	97.49 (6)	C8—C13—C12	119.7 (2)
Cu1iv—Cl1—C4	103.02 (7)	C2—C3—H3	120.00
Cu1—O1—C1	128.08 (15)	C4—C3—H3	120.00
Cu1—N1—C7	122.60 (16)	C4—C5—H5	120.00
Cu1—N1—C8	121.93 (14)	C6—C5—H5	120.00
C7—N1—C8	114.56 (19)	N1—C7—H7	117.00
O1—C1—C2	120.5 (2)	C6—C7—H7	117.00
O1—C1—C6	123.8 (2)	C8—C9—H9	120.00
C2—C1—C6	115.73 (19)	C10—C9—H9	120.00
Br1—C2—C1	118.09 (16)	C9—C10—H10	121.00
Br1—C2—C3	118.95 (17)	C11—C10—H10	121.00
C1—C2—C3	123.0 (2)	C11—C12—H12	120.00
C2—C3—C4	119.1 (2)	C13—C12—H12	120.00
Cl1—C4—C3	119.02 (17)	C8—C13—H13	120.00
Cl1—C4—C5	119.67 (17)	C12—C13—H13	120.00
C3—C4—C5	121.3 (2)
N1—Cu1—O1—C1	22.33 (18)	C6—C1—C2—C3	1.2 (3)
Cl1i—Cu1—O1—C1	119.96 (17)	O1—C1—C6—C5	179.73 (19)
N1ii—Cu1—O1—C1	−157.67 (18)	O1—C1—C6—C7	−5.7 (3)
Cl1iii—Cu1—O1—C1	−60.04 (17)	C2—C1—C6—C5	−0.7 (3)
O1—Cu1—N1—C7	−22.22 (18)	C2—C1—C6—C7	173.92 (19)
O1—Cu1—N1—C8	169.30 (16)	Br1—C2—C3—C4	179.69 (15)
Cl1i—Cu1—N1—C7	−117.39 (17)	C1—C2—C3—C4	−0.9 (3)
Cl1i—Cu1—N1—C8	74.13 (15)	C2—C3—C4—Cl1	−177.01 (16)
O1ii—Cu1—N1—C7	157.78 (18)	C2—C3—C4—C5	0.1 (3)
O1ii—Cu1—N1—C8	−10.70 (16)	Cl1—C4—C5—C6	177.47 (15)
Cl1iii—Cu1—N1—C7	62.61 (17)	C3—C4—C5—C6	0.4 (3)
Cl1iii—Cu1—N1—C8	−105.88 (15)	C4—C5—C6—C1	−0.1 (3)
Cu1iv—Cl1—C4—C3	−124.36 (15)	C4—C5—C6—C7	−174.99 (18)
Cu1iv—Cl1—C4—C5	58.52 (17)	C1—C6—C7—N1	4.1 (3)
Cu1—O1—C1—C2	167.99 (14)	C5—C6—C7—N1	178.9 (2)
Cu1—O1—C1—C6	−12.4 (3)	N1—C8—C9—C10	177.1 (2)
Cu1—N1—C7—C6	13.8 (3)	C13—C8—C9—C10	−0.2 (3)
C8—N1—C7—C6	−176.95 (19)	N1—C8—C13—C12	−177.1 (2)
Cu1—N1—C8—C9	103.7 (2)	C9—C8—C13—C12	0.2 (4)
Cu1—N1—C8—C13	−78.9 (2)	C8—C9—C10—C11	0.5 (3)
C7—N1—C8—C9	−65.6 (3)	C9—C10—C11—Cl2	176.83 (18)
C7—N1—C8—C13	111.7 (2)	C9—C10—C11—C12	−0.8 (4)
O1—C1—C2—Br1	0.2 (3)	Cl2—C11—C12—C13	−176.80 (19)
O1—C1—C2—C3	−179.21 (19)	C10—C11—C12—C13	0.8 (4)
C6—C1—C2—Br1	−179.41 (14)	C11—C12—C13—C8	−0.5 (4)