Di-μ-chlorido-bis-{[2-(8-quinol-yloxy)-acetato-κN,O,O]copper(II)}.

The title compound, [Cu(2)(C(11)H(8)NO(3))(2)Cl(2)], is a bicopper(II) complex. Each Cu(II) ion is five-coordinated by two O atoms and one N atom from the (8-quinol-yloxy)acetate ligand, and by two μ(2)-chloride ligands, thus exhibiting a distorted square-pyramidal CuCl(2)NO(2) coordination environment. Each (8-quinol-yloxy)acetate anion acts as a tridentate chelating ligand. In the crystal structure, adjacent quinolyl rings are involved in strong π-π stacking inter-actions, with inter-planar distances of 3.549 (5) and 3.763 (5) Å, thereby forming a two-dimensional planar network perpendicular to the ab plane. Furthermore, a weak inter-action [2.750 (4) Å] is observed within these planes between one Cu(II) ion and a carboxyl-ate O atom from a ligand in an adjacent mol-ecule, which also contributes to the stability of the structure.

Related literature

For general background, see: Hong et al. (2006 ▶); Sudik et al. (2005 ▶); Dong et al. (2007 ▶); Tong et al., 1999 ▶. For related structures, see: Wang & Lu (2004 ▶); Wang et al. (2005 ▶). Koelsch (1931 ▶) reports the synthesis of the (8-quinol­yloxy)acetate ligand.

Experimental

Crystal data

[Cu2(C11H8NO3)2Cl2]

M = 602.35

Monoclinic,

a = 8.3796 (17) Å

b = 19.195 (4) Å

c = 13.392 (3) Å

β = 98.85 (3)°

V = 2128.4 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.29 mm−1

T = 298 (2) K

0.36 × 0.30 × 0.24 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.462, T max = 0.582

11625 measured reflections

4179 independent reflections

2737 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.087

S = 1.01

4179 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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 ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031656/zl2140sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031656/zl2140Isup2.hkl

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

[Cu2(C11H8NO3)2Cl2]	F(000) = 1208
Mr = 602.35	Dx = 1.880 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2969 reflections
a = 8.3796 (17) Å	θ = 1.9–27.8°
b = 19.195 (4) Å	µ = 2.30 mm−1
c = 13.392 (3) Å	T = 298 K
β = 98.85 (3)°	Block, green
V = 2128.4 (8) Å3	0.36 × 0.30 × 0.24 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4179 independent reflections
Radiation source: fine-focus sealed tube	2737 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.462, Tmax = 0.582	k = −19→23
11625 measured reflections	l = −16→13

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0256P)2 + 1.1172P] where P = (Fo2 + 2Fc2)/3
4179 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.47 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
C1	0.8714 (5)	−0.0068 (2)	0.8758 (3)	0.0368 (10)
H1	0.8366	0.0265	0.9181	0.044*
C2	0.8505 (5)	−0.0778 (2)	0.8966 (3)	0.0432 (12)
H2	0.8054	−0.0908	0.9531	0.052*
C3	0.8959 (5)	−0.1275 (2)	0.8345 (3)	0.0428 (12)
H3	0.8799	−0.1744	0.8473	0.051*
C4	0.9673 (5)	−0.10730 (19)	0.7508 (3)	0.0325 (10)
C5	1.0242 (5)	−0.1536 (2)	0.6825 (4)	0.0409 (12)
H5	1.0099	−0.2012	0.6900	0.049*
C6	1.0990 (5)	−0.1304 (2)	0.6066 (4)	0.0434 (12)
H6	1.1356	−0.1624	0.5631	0.052*
C7	1.1226 (5)	−0.05832 (19)	0.5921 (3)	0.0345 (10)
H7	1.1760	−0.0427	0.5403	0.041*
C8	1.0658 (5)	−0.01268 (18)	0.6549 (3)	0.0282 (9)
C9	0.9887 (4)	−0.03519 (19)	0.7356 (3)	0.0270 (9)
C10	1.1952 (5)	0.09524 (18)	0.6061 (3)	0.0322 (10)
H10A	1.1737	0.0926	0.5329	0.039*
H10B	1.3003	0.0748	0.6291	0.039*
C11	1.1912 (5)	0.17117 (19)	0.6411 (3)	0.0321 (10)
C12	0.6792 (5)	0.2987 (2)	0.6160 (3)	0.0381 (11)
H12	0.7235	0.2651	0.5784	0.046*
C13	0.6801 (5)	0.3683 (2)	0.5850 (3)	0.0437 (12)
H13	0.7255	0.3802	0.5282	0.052*
C14	0.6146 (5)	0.4184 (2)	0.6376 (3)	0.0404 (11)
H14	0.6133	0.4646	0.6163	0.049*
C15	0.5487 (5)	0.40025 (19)	0.7247 (3)	0.0302 (10)
C16	0.4806 (5)	0.4478 (2)	0.7871 (3)	0.0371 (11)
H16	0.4763	0.4950	0.7709	0.044*
C17	0.4217 (5)	0.4254 (2)	0.8700 (3)	0.0380 (11)
H17	0.3793	0.4578	0.9105	0.046*
C18	0.4230 (5)	0.35414 (19)	0.8967 (3)	0.0340 (10)
H18	0.3814	0.3392	0.9536	0.041*
C19	0.4869 (5)	0.30816 (18)	0.8366 (3)	0.0288 (9)
C20	0.5517 (4)	0.32890 (18)	0.7511 (3)	0.0273 (9)
C21	0.3712 (5)	0.20080 (18)	0.8940 (3)	0.0307 (10)
H21A	0.2681	0.2219	0.8677	0.037*
H21B	0.3863	0.2032	0.9672	0.037*
C22	0.3754 (5)	0.1251 (2)	0.8592 (3)	0.0323 (10)
Cl1	0.88233 (13)	0.17203 (5)	0.87627 (8)	0.0355 (3)
Cl2	0.68751 (13)	0.12051 (5)	0.62854 (8)	0.0378 (3)
Cu1	0.98473 (6)	0.11091 (2)	0.75955 (4)	0.03462 (16)
Cu2	0.59143 (6)	0.18353 (2)	0.74655 (4)	0.03365 (16)
N1	0.9383 (4)	0.01413 (15)	0.7986 (2)	0.0284 (8)
N2	0.6180 (4)	0.27902 (15)	0.6966 (2)	0.0284 (8)
O1	1.0725 (3)	0.05920 (12)	0.6493 (2)	0.0345 (7)
O2	1.0939 (3)	0.18630 (12)	0.7016 (2)	0.0350 (7)
O3	1.2868 (4)	0.21096 (14)	0.6113 (2)	0.0504 (9)
O4	0.5008 (3)	0.23677 (12)	0.85579 (19)	0.0296 (6)
O5	0.4801 (3)	0.10898 (12)	0.8035 (2)	0.0369 (7)
O6	0.2728 (4)	0.08555 (14)	0.8829 (2)	0.0501 (8)

	U11	U22	U33	U12	U13	U23
C1	0.037 (3)	0.038 (2)	0.040 (3)	−0.0059 (19)	0.018 (2)	−0.001 (2)
C2	0.047 (3)	0.042 (3)	0.043 (3)	−0.010 (2)	0.017 (2)	0.015 (2)
C3	0.045 (3)	0.028 (2)	0.055 (3)	−0.005 (2)	0.006 (2)	0.007 (2)
C4	0.031 (3)	0.025 (2)	0.040 (3)	−0.0021 (17)	0.001 (2)	0.0057 (19)
C5	0.042 (3)	0.017 (2)	0.062 (3)	0.0001 (18)	0.002 (2)	−0.002 (2)
C6	0.048 (3)	0.031 (2)	0.049 (3)	0.009 (2)	0.001 (2)	−0.015 (2)
C7	0.039 (3)	0.032 (2)	0.032 (3)	0.0041 (18)	0.006 (2)	−0.0038 (19)
C8	0.029 (2)	0.021 (2)	0.034 (2)	0.0002 (16)	0.0036 (19)	−0.0039 (17)
C9	0.025 (2)	0.026 (2)	0.030 (2)	0.0031 (16)	0.0046 (18)	0.0019 (18)
C10	0.035 (3)	0.033 (2)	0.032 (2)	−0.0030 (18)	0.0151 (19)	0.0014 (19)
C11	0.034 (3)	0.029 (2)	0.034 (3)	−0.0018 (18)	0.008 (2)	0.0014 (19)
C12	0.042 (3)	0.039 (2)	0.036 (3)	−0.007 (2)	0.015 (2)	−0.004 (2)
C13	0.054 (3)	0.043 (3)	0.037 (3)	−0.009 (2)	0.016 (2)	0.006 (2)
C14	0.048 (3)	0.031 (2)	0.043 (3)	−0.006 (2)	0.009 (2)	0.008 (2)
C15	0.028 (2)	0.028 (2)	0.033 (3)	−0.0051 (17)	0.0011 (19)	0.0008 (18)
C16	0.040 (3)	0.022 (2)	0.047 (3)	0.0005 (18)	0.000 (2)	−0.004 (2)
C17	0.042 (3)	0.027 (2)	0.048 (3)	0.0005 (19)	0.014 (2)	−0.009 (2)
C18	0.038 (3)	0.030 (2)	0.037 (3)	−0.0006 (18)	0.017 (2)	−0.0072 (19)
C19	0.031 (2)	0.023 (2)	0.032 (2)	−0.0030 (17)	0.0058 (19)	0.0014 (18)
C20	0.028 (2)	0.022 (2)	0.032 (2)	−0.0033 (16)	0.0042 (18)	−0.0042 (17)
C21	0.032 (2)	0.028 (2)	0.036 (3)	−0.0038 (17)	0.0158 (19)	−0.0004 (18)
C22	0.038 (3)	0.029 (2)	0.030 (3)	−0.0011 (18)	0.005 (2)	0.0003 (18)
Cl1	0.0459 (7)	0.0303 (5)	0.0342 (6)	0.0017 (4)	0.0184 (5)	−0.0031 (4)
Cl2	0.0448 (7)	0.0367 (6)	0.0346 (6)	0.0054 (5)	0.0142 (5)	−0.0073 (5)
Cu1	0.0460 (3)	0.0222 (3)	0.0414 (3)	−0.0020 (2)	0.0248 (2)	−0.0008 (2)
Cu2	0.0420 (3)	0.0234 (3)	0.0405 (3)	−0.0009 (2)	0.0220 (2)	−0.0033 (2)
N1	0.0268 (19)	0.0278 (17)	0.033 (2)	−0.0023 (14)	0.0128 (15)	0.0011 (15)
N2	0.030 (2)	0.0251 (17)	0.032 (2)	−0.0029 (14)	0.0101 (16)	−0.0027 (15)
O1	0.0459 (19)	0.0225 (14)	0.0404 (18)	−0.0029 (12)	0.0241 (14)	0.0024 (12)
O2	0.0457 (19)	0.0259 (14)	0.0383 (18)	−0.0044 (13)	0.0220 (14)	−0.0003 (13)
O3	0.055 (2)	0.0372 (17)	0.067 (2)	−0.0154 (15)	0.0353 (18)	−0.0038 (16)
O4	0.0359 (17)	0.0216 (13)	0.0355 (17)	−0.0016 (11)	0.0192 (13)	−0.0022 (12)
O5	0.0466 (19)	0.0231 (14)	0.0464 (19)	−0.0008 (13)	0.0240 (15)	−0.0021 (13)
O6	0.055 (2)	0.0334 (16)	0.070 (2)	−0.0102 (15)	0.0363 (18)	−0.0018 (16)

C1—N1	1.312 (5)	C14—C15	1.409 (6)
C1—C2	1.409 (5)	C14—H14	0.9300
C1—H1	0.9300	C15—C20	1.414 (5)
C2—C3	1.357 (6)	C15—C16	1.416 (5)
C2—H2	0.9300	C16—C17	1.353 (6)
C3—C4	1.405 (6)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.414 (5)
C4—C5	1.408 (6)	C17—H17	0.9300
C4—C9	1.414 (5)	C18—C19	1.359 (5)
C5—C6	1.349 (6)	C18—H18	0.9300
C5—H5	0.9300	C19—O4	1.396 (4)
C6—C7	1.416 (5)	C19—C20	1.398 (5)
C6—H6	0.9300	C20—N2	1.372 (5)
C7—C8	1.351 (5)	C21—O4	1.445 (4)
C7—H7	0.9300	C21—C22	1.528 (5)
C8—O1	1.383 (4)	C21—H21A	0.9700
C8—C9	1.409 (5)	C21—H21B	0.9700
C9—N1	1.377 (5)	C22—O6	1.224 (5)
C10—O1	1.433 (4)	C22—O5	1.274 (5)
C10—C11	1.533 (5)	Cl1—Cu1	2.2290 (12)
C10—H10A	0.9700	Cl2—Cu2	2.2362 (12)
C10—H10B	0.9700	Cu1—O2	1.937 (3)
C11—O3	1.218 (5)	Cu1—N1	1.985 (3)
C11—O2	1.269 (5)	Cu1—O1	2.011 (3)
C12—N2	1.320 (5)	Cu2—O5	1.929 (3)
C12—C13	1.400 (5)	Cu2—N2	1.976 (3)
C12—H12	0.9300	Cu2—O4	2.026 (3)
C13—C14	1.357 (6)	Cu1—Cl2	2.8232 (14)
C13—H13	0.9300	Cu2—Cl1	2.7761 (12)
N1—C1—C2	122.2 (4)	C17—C16—H16	119.6
N1—C1—H1	118.9	C15—C16—H16	119.6
C2—C1—H1	118.9	C16—C17—C18	121.7 (4)
C3—C2—C1	120.2 (4)	C16—C17—H17	119.1
C3—C2—H2	119.9	C18—C17—H17	119.1
C1—C2—H2	119.9	C19—C18—C17	117.8 (4)
C2—C3—C4	119.4 (4)	C19—C18—H18	121.1
C2—C3—H3	120.3	C17—C18—H18	121.1
C4—C3—H3	120.3	C18—C19—O4	123.9 (4)
C3—C4—C5	124.9 (4)	C18—C19—C20	122.6 (4)
C3—C4—C9	117.6 (4)	O4—C19—C20	113.5 (3)
C5—C4—C9	117.4 (4)	N2—C20—C19	118.5 (3)
C6—C5—C4	121.6 (4)	N2—C20—C15	122.4 (4)
C6—C5—H5	119.2	C19—C20—C15	119.1 (4)
C4—C5—H5	119.2	O4—C21—C22	107.0 (3)
C5—C6—C7	121.1 (4)	O4—C21—H21A	110.3
C5—C6—H6	119.5	C22—C21—H21A	110.3
C7—C6—H6	119.5	O4—C21—H21B	110.3
C8—C7—C6	118.6 (4)	C22—C21—H21B	110.3
C8—C7—H7	120.7	H21A—C21—H21B	108.6
C6—C7—H7	120.7	O6—C22—O5	125.1 (4)
C7—C8—O1	126.2 (4)	O6—C22—C21	117.4 (4)
C7—C8—C9	121.7 (3)	O5—C22—C21	117.3 (3)
O1—C8—C9	112.0 (3)	O2—Cu1—N1	158.25 (12)
N1—C9—C8	118.6 (3)	O2—Cu1—O1	79.98 (11)
N1—C9—C4	121.8 (4)	N1—Cu1—O1	80.80 (12)
C8—C9—C4	119.6 (4)	O2—Cu1—Cl1	98.29 (9)
O1—C10—C11	106.5 (3)	N1—Cu1—Cl1	101.28 (10)
O1—C10—H10A	110.4	O1—Cu1—Cl1	177.22 (8)
C11—C10—H10A	110.4	O5—Cu2—N2	155.37 (13)
O1—C10—H10B	110.4	O5—Cu2—O4	80.24 (11)
C11—C10—H10B	110.4	N2—Cu2—O4	81.42 (12)
H10A—C10—H10B	108.6	O5—Cu2—Cl2	97.29 (9)
O3—C11—O2	125.9 (4)	N2—Cu2—Cl2	101.01 (10)
O3—C11—C10	116.7 (4)	O4—Cu2—Cl2	177.52 (8)
O2—C11—C10	117.3 (3)	C1—N1—C9	118.8 (3)
N2—C12—C13	122.4 (4)	C1—N1—Cu1	128.2 (3)
N2—C12—H12	118.8	C9—N1—Cu1	113.0 (2)
C13—C12—H12	118.8	C12—N2—C20	118.4 (3)
C14—C13—C12	120.1 (4)	C12—N2—Cu2	128.4 (3)
C14—C13—H13	119.9	C20—N2—Cu2	113.0 (3)
C12—C13—H13	119.9	C8—O1—C10	122.8 (3)
C13—C14—C15	119.7 (4)	C8—O1—Cu1	115.4 (2)
C13—C14—H14	120.2	C10—O1—Cu1	115.1 (2)
C15—C14—H14	120.2	C11—O2—Cu1	118.3 (2)
C14—C15—C20	117.0 (4)	C19—O4—C21	119.2 (3)
C14—C15—C16	125.0 (4)	C19—O4—Cu2	113.1 (2)
C20—C15—C16	118.0 (4)	C21—O4—Cu2	113.6 (2)
C17—C16—C15	120.7 (4)	C22—O5—Cu2	118.1 (2)
N1—C1—C2—C3	−1.9 (7)	O1—Cu1—N1—C1	179.2 (4)
C1—C2—C3—C4	1.5 (7)	Cl1—Cu1—N1—C1	−2.7 (4)
C2—C3—C4—C5	177.9 (4)	O2—Cu1—N1—C9	−27.2 (5)
C2—C3—C4—C9	0.1 (6)	O1—Cu1—N1—C9	0.9 (3)
C3—C4—C5—C6	−176.6 (4)	Cl1—Cu1—N1—C9	179.0 (2)
C9—C4—C5—C6	1.2 (6)	C13—C12—N2—C20	0.6 (6)
C4—C5—C6—C7	−0.4 (7)	C13—C12—N2—Cu2	175.1 (3)
C5—C6—C7—C8	−1.2 (6)	C19—C20—N2—C12	−179.9 (4)
C6—C7—C8—O1	−177.3 (4)	C15—C20—N2—C12	−0.8 (6)
C6—C7—C8—C9	1.9 (6)	C19—C20—N2—Cu2	4.7 (4)
C7—C8—C9—N1	178.0 (3)	C15—C20—N2—Cu2	−176.2 (3)
O1—C8—C9—N1	−2.7 (5)	O5—Cu2—N2—C12	−138.4 (4)
C7—C8—C9—C4	−1.0 (6)	O4—Cu2—N2—C12	179.4 (4)
O1—C8—C9—C4	178.2 (3)	Cl2—Cu2—N2—C12	−1.1 (4)
C3—C4—C9—N1	−1.6 (6)	O5—Cu2—N2—C20	36.4 (5)
C5—C4—C9—N1	−179.5 (3)	O4—Cu2—N2—C20	−5.8 (2)
C3—C4—C9—C8	177.4 (4)	Cl2—Cu2—N2—C20	173.7 (2)
C5—C4—C9—C8	−0.5 (6)	C7—C8—O1—C10	−27.5 (6)
O1—C10—C11—O3	−179.3 (4)	C9—C8—O1—C10	153.3 (3)
O1—C10—C11—O2	3.5 (5)	C7—C8—O1—Cu1	−177.4 (3)
N2—C12—C13—C14	−0.8 (7)	C9—C8—O1—Cu1	3.4 (4)
C12—C13—C14—C15	1.2 (7)	C11—C10—O1—C8	−163.9 (3)
C13—C14—C15—C20	−1.4 (6)	C11—C10—O1—Cu1	−13.9 (4)
C13—C14—C15—C16	178.5 (4)	O2—Cu1—O1—C8	167.3 (3)
C14—C15—C16—C17	−179.3 (4)	N1—Cu1—O1—C8	−2.5 (2)
C20—C15—C16—C17	0.6 (6)	O2—Cu1—O1—C10	15.1 (2)
C15—C16—C17—C18	−1.1 (6)	N1—Cu1—O1—C10	−154.7 (3)
C16—C17—C18—C19	0.5 (6)	O3—C11—O2—Cu1	−167.7 (3)
C17—C18—C19—O4	177.8 (3)	C10—C11—O2—Cu1	9.2 (5)
C17—C18—C19—C20	0.6 (6)	N1—Cu1—O2—C11	14.9 (5)
C18—C19—C20—N2	178.1 (4)	O1—Cu1—O2—C11	−13.4 (3)
O4—C19—C20—N2	0.6 (5)	Cl1—Cu1—O2—C11	168.8 (3)
C18—C19—C20—C15	−1.0 (6)	C18—C19—O4—C21	39.6 (5)
O4—C19—C20—C15	−178.5 (3)	C20—C19—O4—C21	−143.0 (3)
C14—C15—C20—N2	1.3 (6)	C18—C19—O4—Cu2	177.1 (3)
C16—C15—C20—N2	−178.7 (3)	C20—C19—O4—Cu2	−5.4 (4)
C14—C15—C20—C19	−179.6 (4)	C22—C21—O4—C19	152.5 (3)
C16—C15—C20—C19	0.4 (5)	C22—C21—O4—Cu2	15.1 (4)
O4—C21—C22—O6	−179.0 (3)	O5—Cu2—O4—C19	−157.3 (2)
O4—C21—C22—O5	−2.6 (5)	N2—Cu2—O4—C19	6.2 (2)
C2—C1—N1—C9	0.5 (6)	O5—Cu2—O4—C21	−17.3 (2)
C2—C1—N1—Cu1	−177.8 (3)	N2—Cu2—O4—C21	146.2 (3)
C8—C9—N1—C1	−177.7 (3)	O6—C22—O5—Cu2	163.8 (3)
C4—C9—N1—C1	1.3 (6)	C21—C22—O5—Cu2	−12.3 (5)
C8—C9—N1—Cu1	0.7 (4)	N2—Cu2—O5—C22	−25.9 (5)
C4—C9—N1—Cu1	179.7 (3)	O4—Cu2—O5—C22	16.5 (3)
O2—Cu1—N1—C1	151.1 (3)	Cl2—Cu2—O5—C22	−163.8 (3)