Di-μ(2)-acetato-1:2κ(2)O:O';2:3κ(2)O:O'-bis-{μ(2)-4,4'-dichloro-2,2'-[2,2-dimethyl-propane-1,3-diylbis(nitrilo-methanylyl-idene)]diphenolato}-1:2κ(6)O,N,N',O':O,O';2:3κ(6)O,O':O,N,N',O'-tricopper(II).

The title compound, [Cu(3)(C(19)H(18)Cl(2)N(2)O(2))(2)(CH(3)CO(2))(2)], is a linear homo-trinuclear Cu(II) complex. The central Cu(II) atom is located on a centre of inversion and has a distorted octa-hedral coordination environment formed by six O atoms from two tetra-dentate Schiff base ligands and two bridging acetate ligands. The coordination geometry of the terminal Cu(II) atom is square-pyramidal with a tetra-dentate ligand in the basal plane. The apical site is occupied by one O atom from an acetate ligand. The acetate-bridged Cu⋯Cu distance is 3.0910 (5) Å. An intra-molecular C-H⋯O hydrogen bond forms an S(6) ring motif. The crystal of the trinuclear complex is stabilized by C-H⋯O hydrogen bonds.

Related literature

For the supra­molecular chemistry of related complexes, see: Chen et al. (2010 ▶); von Richthofen et al. (2009 ▶); Gianneschi et al. (2003 ▶). For related structures, see: Atakol et al. (1999 ▶); Feng et al. (2007 ▶); Ray et al. (2009 ▶); Yang et al. (2004 ▶). For background to this work, see: Fukuhara et al. (1990 ▶); Kargar et al. (2012 ▶); Kubono et al. (2009 ▶, 2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For analysis of ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

[Cu3(C19H18Cl2N2O2)2(C2H3O2)2]

M = 1063.25

Orthorhombic,

a = 19.0732 (18) Å

b = 11.6191 (11) Å

c = 19.693 (3) Å

V = 4364.2 (9) Å3

Z = 4

Mo Kα radiation

μ = 1.75 mm−1

T = 298 K

0.23 × 0.20 × 0.16 mm

Data collection

Rigaku AFC7R diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.675, T max = 0.756

7325 measured reflections

5006 independent reflections

2796 reflections with F 2 > 2.0σ(F 2)

R int = 0.024

3 standard reflections every 150 reflections intensity decay: 0.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.105

S = 1.00

5006 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.45 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2010 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: CrystalStructure.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044315/mw2092sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044315/mw2092Isup2.hkl

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

[Cu3(C19H18Cl2N2O2)2(C2H3O2)2]	F(000) = 2164.00
Mr = 1063.25	Dx = 1.618 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 19.0732 (18) Å	θ = 15.0–17.4°
b = 11.6191 (11) Å	µ = 1.75 mm−1
c = 19.693 (3) Å	T = 298 K
V = 4364.2 (9) Å3	Prismatic, green
Z = 4	0.23 × 0.20 × 0.16 mm

Rigaku AFC7R diffractometer	Rint = 0.024
ω–2θ scans	θmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = −13→24
Tmin = 0.675, Tmax = 0.756	k = −8→15
7325 measured reflections	l = −25→0
5006 independent reflections	3 standard reflections every 150 reflections
2796 reflections with F2 > 2.0σ(F2)	intensity decay: 0.5%

Refinement on F2	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0428P)2 + 0.7391P] where P = (Fo2 + 2Fc2)/3
5006 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.45 e Å−3
Primary atom site location: structure-invariant direct methods

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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
Cu1	0.64313 (2)	0.07637 (3)	0.44178 (2)	0.03103 (12)
Cu2	0.5000	0.0000	0.5000	0.02727 (14)
Cl1	0.47496 (6)	−0.12235 (10)	0.13509 (5)	0.0602 (3)
Cl2	0.77615 (6)	−0.36381 (9)	0.66639 (5)	0.0635 (3)
O1	0.54772 (11)	0.0350 (2)	0.40871 (11)	0.0336 (5)
O2	0.61636 (11)	−0.01062 (19)	0.52089 (11)	0.0359 (6)
O3	0.60366 (11)	0.23406 (18)	0.48839 (11)	0.0363 (6)
O4	0.49941 (11)	0.16268 (18)	0.52142 (11)	0.0341 (5)
N1	0.66389 (14)	0.1401 (2)	0.35159 (14)	0.0326 (6)
N2	0.74426 (14)	0.0639 (2)	0.46700 (14)	0.0349 (7)
C1	0.53159 (17)	0.0020 (3)	0.34682 (16)	0.0302 (7)
C2	0.47113 (18)	−0.0639 (3)	0.33434 (18)	0.0384 (8)
H2	0.4416	−0.0830	0.3702	0.046*
C3	0.45508 (19)	−0.1003 (3)	0.27000 (18)	0.0418 (9)
H3	0.4152	−0.1447	0.2628	0.050*
C4	0.49741 (19)	−0.0718 (3)	0.21590 (18)	0.0405 (9)
C5	0.55477 (18)	−0.0033 (3)	0.22513 (18)	0.0385 (8)
H5	0.5816	0.0188	0.1879	0.046*
C6	0.57347 (17)	0.0342 (3)	0.29035 (17)	0.0320 (8)
C7	0.63314 (18)	0.1099 (3)	0.29713 (19)	0.0374 (8)
H7	0.6511	0.1401	0.2570	0.045*
C8	0.72103 (18)	0.2234 (3)	0.34661 (19)	0.0433 (9)
H8A	0.7110	0.2877	0.3765	0.052*
H8B	0.7229	0.2527	0.3005	0.052*
C9	0.79266 (17)	0.1737 (3)	0.36505 (18)	0.0390 (9)
C10	0.79631 (19)	0.1469 (3)	0.44084 (18)	0.0465 (10)
H10A	0.8428	0.1175	0.4509	0.056*
H10B	0.7908	0.2185	0.4656	0.056*
C11	0.8086 (2)	0.0676 (4)	0.3228 (2)	0.0584 (11)
H11A	0.7764	0.0072	0.3345	0.088*
H11B	0.8557	0.0426	0.3316	0.088*
H11C	0.8038	0.0859	0.2755	0.088*
C12	0.8473 (2)	0.2683 (4)	0.3510 (2)	0.0592 (12)
H12A	0.8928	0.2418	0.3646	0.089*
H12B	0.8353	0.3362	0.3763	0.089*
H12C	0.8477	0.2859	0.3034	0.089*
C13	0.76749 (18)	−0.0137 (3)	0.50710 (17)	0.0407 (9)
H13	0.8160	−0.0181	0.5115	0.049*
C14	0.72733 (18)	−0.0952 (3)	0.54648 (16)	0.0345 (8)
C15	0.76437 (19)	−0.1790 (3)	0.58283 (18)	0.0426 (9)
H15	0.8130	−0.1824	0.5795	0.051*
C16	0.72974 (19)	−0.2558 (3)	0.62314 (18)	0.0416 (9)
C17	0.65761 (19)	−0.2510 (3)	0.63013 (18)	0.0434 (9)
H17	0.6346	−0.3027	0.6585	0.052*
C18	0.62008 (19)	−0.1695 (3)	0.59500 (17)	0.0408 (9)
H18	0.5715	−0.1677	0.5993	0.049*
C19	0.65340 (17)	−0.0887 (3)	0.55256 (16)	0.0312 (7)
C20	0.54487 (18)	0.2416 (3)	0.51585 (16)	0.0312 (7)
C21	0.5241 (2)	0.3555 (3)	0.5462 (2)	0.0532 (11)
H21A	0.5584	0.4126	0.5345	0.080*
H21B	0.5214	0.3484	0.5947	0.080*
H21C	0.4792	0.3781	0.5287	0.080*

	U11	U22	U33	U12	U13	U23
Cu1	0.0229 (2)	0.0343 (2)	0.0359 (2)	−0.00107 (18)	0.00405 (18)	0.00024 (19)
Cu2	0.0223 (3)	0.0305 (3)	0.0290 (3)	−0.0010 (2)	0.0029 (2)	−0.0011 (2)
Cl1	0.0663 (7)	0.0744 (7)	0.0398 (5)	−0.0041 (6)	−0.0070 (5)	−0.0176 (5)
Cl2	0.0759 (8)	0.0619 (7)	0.0526 (6)	0.0295 (6)	−0.0149 (6)	0.0059 (5)
O1	0.0232 (12)	0.0450 (13)	0.0324 (13)	−0.0047 (11)	0.0016 (10)	−0.0044 (11)
O2	0.0274 (12)	0.0403 (14)	0.0400 (13)	0.0061 (11)	0.0050 (10)	0.0114 (12)
O3	0.0290 (12)	0.0341 (13)	0.0459 (15)	−0.0015 (11)	0.0017 (11)	−0.0057 (11)
O4	0.0318 (13)	0.0287 (12)	0.0419 (14)	−0.0008 (11)	0.0038 (11)	−0.0014 (10)
N1	0.0263 (15)	0.0311 (15)	0.0404 (17)	−0.0023 (12)	0.0009 (13)	0.0044 (13)
N2	0.0267 (15)	0.0431 (18)	0.0348 (15)	−0.0058 (13)	0.0037 (13)	−0.0025 (14)
C1	0.0291 (18)	0.0295 (18)	0.0320 (18)	0.0061 (15)	−0.0024 (15)	0.0003 (15)
C2	0.0329 (19)	0.045 (2)	0.0372 (19)	−0.0049 (16)	0.0018 (16)	−0.0017 (17)
C3	0.036 (2)	0.046 (2)	0.044 (2)	−0.0065 (18)	−0.0038 (18)	−0.0029 (18)
C4	0.042 (2)	0.046 (2)	0.034 (2)	0.0053 (19)	−0.0068 (16)	−0.0066 (17)
C5	0.034 (2)	0.046 (2)	0.0355 (19)	0.0010 (18)	0.0019 (16)	0.0012 (17)
C6	0.0263 (18)	0.0307 (18)	0.0390 (19)	0.0015 (14)	0.0011 (15)	0.0007 (15)
C7	0.035 (2)	0.0363 (19)	0.041 (2)	0.0015 (16)	0.0056 (16)	0.0098 (17)
C8	0.041 (2)	0.036 (2)	0.053 (2)	−0.0105 (17)	−0.0012 (18)	0.0059 (18)
C9	0.029 (2)	0.042 (2)	0.046 (2)	−0.0053 (16)	0.0060 (17)	0.0026 (17)
C10	0.035 (2)	0.056 (2)	0.048 (2)	−0.0185 (18)	−0.0001 (18)	0.0040 (19)
C11	0.048 (3)	0.062 (3)	0.065 (3)	0.000 (2)	0.020 (2)	−0.009 (2)
C12	0.042 (2)	0.068 (3)	0.067 (3)	−0.024 (2)	0.002 (2)	0.018 (2)
C13	0.0235 (18)	0.059 (3)	0.039 (2)	−0.0007 (17)	0.0005 (15)	−0.0009 (19)
C14	0.0304 (19)	0.043 (2)	0.0300 (18)	0.0035 (16)	0.0013 (14)	−0.0050 (16)
C15	0.031 (2)	0.056 (2)	0.040 (2)	0.0092 (18)	−0.0029 (16)	−0.0001 (19)
C16	0.045 (2)	0.042 (2)	0.037 (2)	0.0148 (19)	−0.0076 (17)	−0.0029 (17)
C17	0.050 (2)	0.043 (2)	0.038 (2)	0.0009 (19)	−0.0065 (18)	0.0115 (17)
C18	0.032 (2)	0.047 (2)	0.043 (2)	0.0013 (17)	0.0041 (17)	0.0103 (18)
C19	0.0289 (18)	0.0321 (18)	0.0325 (18)	−0.0001 (15)	0.0003 (14)	−0.0026 (15)
C20	0.0343 (18)	0.0285 (18)	0.0309 (19)	0.0034 (15)	−0.0048 (15)	0.0007 (14)
C21	0.046 (2)	0.039 (2)	0.075 (3)	0.0012 (19)	0.014 (2)	−0.019 (2)

Cu1—O2	1.926 (2)	C7—H7	0.9300
Cu1—N1	1.965 (3)	C8—C9	1.527 (5)
Cu1—O1	1.992 (2)	C8—H8A	0.9700
Cu1—N2	1.997 (3)	C8—H8B	0.9700
Cu1—O3	2.183 (2)	C9—C11	1.518 (5)
Cu2—O4i	1.937 (2)	C9—C10	1.526 (5)
Cu2—O4	1.937 (2)	C9—C12	1.540 (5)
Cu2—O1	2.056 (2)	C10—H10A	0.9700
Cu2—O1i	2.056 (2)	C10—H10B	0.9700
Cu2—O2i	2.260 (2)	C11—H11A	0.9600
Cu2—O2	2.260 (2)	C11—H11B	0.9600
Cl1—C4	1.750 (4)	C11—H11C	0.9600
Cl2—C16	1.756 (4)	C12—H12A	0.9600
O1—C1	1.314 (4)	C12—H12B	0.9600
O2—C19	1.308 (4)	C12—H12C	0.9600
O3—C20	1.248 (4)	C13—C14	1.444 (5)
O4—C20	1.267 (4)	C13—H13	0.9300
N1—C7	1.272 (4)	C14—C15	1.400 (5)
N1—C8	1.461 (4)	C14—C19	1.417 (4)
N2—C13	1.277 (4)	C15—C16	1.364 (5)
N2—C10	1.477 (4)	C15—H15	0.9300
C1—C2	1.406 (5)	C16—C17	1.384 (5)
C1—C6	1.419 (4)	C17—C18	1.374 (4)
C2—C3	1.371 (5)	C17—H17	0.9300
C2—H2	0.9300	C18—C19	1.408 (4)
C3—C4	1.377 (5)	C18—H18	0.9300
C3—H3	0.9300	C20—C21	1.504 (5)
C4—C5	1.365 (5)	C21—H21A	0.9600
C5—C6	1.402 (4)	C21—H21B	0.9600
C5—H5	0.9300	C21—H21C	0.9600
C6—C7	1.445 (5)
O2—Cu1—N1	169.27 (11)	N1—C8—C9	113.6 (3)
O2—Cu1—O1	84.00 (9)	N1—C8—H8A	108.8
N1—Cu1—O1	88.83 (10)	C9—C8—H8A	108.8
O2—Cu1—N2	90.96 (11)	N1—C8—H8B	108.8
N1—Cu1—N2	93.31 (11)	C9—C8—H8B	108.8
O1—Cu1—N2	161.12 (11)	H8A—C8—H8B	107.7
O2—Cu1—O3	90.51 (9)	C11—C9—C10	111.2 (3)
N1—Cu1—O3	97.66 (10)	C11—C9—C8	110.8 (3)
O1—Cu1—O3	91.44 (9)	C10—C9—C8	110.5 (3)
N2—Cu1—O3	106.83 (10)	C11—C9—C12	110.2 (3)
O4i—Cu2—O4	180.00 (13)	C10—C9—C12	106.9 (3)
O4i—Cu2—O1	89.99 (9)	C8—C9—C12	107.0 (3)
O4—Cu2—O1	90.01 (9)	N2—C10—C9	116.3 (3)
O4i—Cu2—O1i	90.01 (9)	N2—C10—H10A	108.2
O4—Cu2—O1i	89.99 (9)	C9—C10—H10A	108.2
O1—Cu2—O1i	180.00 (10)	N2—C10—H10B	108.2
O4i—Cu2—O2i	91.11 (8)	C9—C10—H10B	108.2
O4—Cu2—O2i	88.89 (8)	H10A—C10—H10B	107.4
O1—Cu2—O2i	105.35 (8)	C9—C11—H11A	109.5
O1i—Cu2—O2i	74.65 (8)	C9—C11—H11B	109.5
O4i—Cu2—O2	88.89 (8)	H11A—C11—H11B	109.5
O4—Cu2—O2	91.11 (8)	C9—C11—H11C	109.5
O1—Cu2—O2	74.65 (8)	H11A—C11—H11C	109.5
O1i—Cu2—O2	105.35 (8)	H11B—C11—H11C	109.5
O2i—Cu2—O2	180.0	C9—C12—H12A	109.5
C1—O1—Cu1	126.0 (2)	C9—C12—H12B	109.5
C1—O1—Cu2	130.5 (2)	H12A—C12—H12B	109.5
Cu1—O1—Cu2	99.58 (9)	C9—C12—H12C	109.5
C19—O2—Cu1	127.3 (2)	H12A—C12—H12C	109.5
C19—O2—Cu2	130.9 (2)	H12B—C12—H12C	109.5
Cu1—O2—Cu2	94.85 (9)	N2—C13—C14	127.6 (3)
C20—O3—Cu1	123.5 (2)	N2—C13—H13	116.2
C20—O4—Cu2	133.1 (2)	C14—C13—H13	116.2
C7—N1—C8	118.1 (3)	C15—C14—C19	119.7 (3)
C7—N1—Cu1	124.4 (2)	C15—C14—C13	117.6 (3)
C8—N1—Cu1	117.4 (2)	C19—C14—C13	122.6 (3)
C13—N2—C10	116.3 (3)	C16—C15—C14	120.5 (3)
C13—N2—Cu1	122.7 (2)	C16—C15—H15	119.7
C10—N2—Cu1	121.0 (2)	C14—C15—H15	119.7
O1—C1—C2	120.9 (3)	C15—C16—C17	120.9 (3)
O1—C1—C6	121.2 (3)	C15—C16—Cl2	120.3 (3)
C2—C1—C6	117.9 (3)	C17—C16—Cl2	118.8 (3)
C3—C2—C1	120.9 (3)	C18—C17—C16	119.7 (3)
C3—C2—H2	119.6	C18—C17—H17	120.1
C1—C2—H2	119.6	C16—C17—H17	120.1
C2—C3—C4	120.7 (3)	C17—C18—C19	121.5 (3)
C2—C3—H3	119.7	C17—C18—H18	119.2
C4—C3—H3	119.7	C19—C18—H18	119.2
C5—C4—C3	120.5 (3)	O2—C19—C18	120.1 (3)
C5—C4—Cl1	120.9 (3)	O2—C19—C14	122.3 (3)
C3—C4—Cl1	118.7 (3)	C18—C19—C14	117.6 (3)
C4—C5—C6	120.4 (3)	O3—C20—O4	127.0 (3)
C4—C5—H5	119.8	O3—C20—C21	118.1 (3)
C6—C5—H5	119.8	O4—C20—C21	115.0 (3)
C5—C6—C1	119.5 (3)	C20—C21—H21A	109.5
C5—C6—C7	118.3 (3)	C20—C21—H21B	109.5
C1—C6—C7	122.1 (3)	H21A—C21—H21B	109.5
N1—C7—C6	127.5 (3)	C20—C21—H21C	109.5
N1—C7—H7	116.2	H21A—C21—H21C	109.5
C6—C7—H7	116.2	H21B—C21—H21C	109.5
O2—Cu1—O1—C1	−137.9 (3)	Cu1—O1—C1—C2	156.4 (2)
N1—Cu1—O1—C1	34.1 (3)	Cu2—O1—C1—C2	3.4 (5)
N2—Cu1—O1—C1	−62.7 (4)	Cu1—O1—C1—C6	−25.2 (4)
O3—Cu1—O1—C1	131.8 (2)	Cu2—O1—C1—C6	−178.2 (2)
O2—Cu1—O1—Cu2	21.70 (10)	O1—C1—C2—C3	−178.6 (3)
N1—Cu1—O1—Cu2	−166.30 (11)	C6—C1—C2—C3	3.0 (5)
N2—Cu1—O1—Cu2	96.9 (3)	C1—C2—C3—C4	−0.9 (6)
O3—Cu1—O1—Cu2	−68.66 (10)	C2—C3—C4—C5	−2.3 (6)
O4i—Cu2—O1—C1	50.4 (3)	C2—C3—C4—Cl1	179.1 (3)
O4—Cu2—O1—C1	−129.6 (3)	C3—C4—C5—C6	3.3 (5)
O2i—Cu2—O1—C1	−40.8 (3)	Cl1—C4—C5—C6	−178.2 (3)
O2—Cu2—O1—C1	139.2 (3)	C4—C5—C6—C1	−1.1 (5)
O4i—Cu2—O1—Cu1	−107.81 (10)	C4—C5—C6—C7	−177.8 (3)
O4—Cu2—O1—Cu1	72.19 (10)	O1—C1—C6—C5	179.6 (3)
O2i—Cu2—O1—Cu1	161.04 (9)	C2—C1—C6—C5	−2.0 (5)
O2—Cu2—O1—Cu1	−18.96 (9)	O1—C1—C6—C7	−3.8 (5)
N1—Cu1—O2—C19	85.3 (6)	C2—C1—C6—C7	174.6 (3)
O1—Cu1—O2—C19	133.6 (3)	C8—N1—C7—C6	−176.5 (3)
N2—Cu1—O2—C19	−28.2 (3)	Cu1—N1—C7—C6	6.9 (5)
O3—Cu1—O2—C19	−135.0 (3)	C5—C6—C7—N1	−169.5 (3)
N1—Cu1—O2—Cu2	−67.7 (5)	C1—C6—C7—N1	13.9 (5)
O1—Cu1—O2—Cu2	−19.43 (9)	C7—N1—C8—C9	−113.3 (4)
N2—Cu1—O2—Cu2	178.80 (10)	Cu1—N1—C8—C9	63.6 (4)
O3—Cu1—O2—Cu2	71.96 (9)	N1—C8—C9—C11	54.7 (4)
O4i—Cu2—O2—C19	−41.8 (3)	N1—C8—C9—C10	−69.0 (4)
O4—Cu2—O2—C19	138.2 (3)	N1—C8—C9—C12	174.9 (3)
O1—Cu2—O2—C19	−132.1 (3)	C13—N2—C10—C9	134.9 (3)
O1i—Cu2—O2—C19	47.9 (3)	Cu1—N2—C10—C9	−46.4 (4)
O4i—Cu2—O2—Cu1	109.72 (10)	C11—C9—C10—N2	−64.1 (4)
O4—Cu2—O2—Cu1	−70.28 (10)	C8—C9—C10—N2	59.5 (4)
O1—Cu2—O2—Cu1	19.42 (9)	C12—C9—C10—N2	175.6 (3)
O1i—Cu2—O2—Cu1	−160.58 (9)	C10—N2—C13—C14	171.2 (3)
O2—Cu1—O3—C20	−48.2 (2)	Cu1—N2—C13—C14	−7.4 (5)
N1—Cu1—O3—C20	124.9 (2)	N2—C13—C14—C15	174.8 (3)
O1—Cu1—O3—C20	35.9 (2)	N2—C13—C14—C19	−9.1 (6)
N2—Cu1—O3—C20	−139.3 (2)	C19—C14—C15—C16	1.2 (5)
O1—Cu2—O4—C20	−44.3 (3)	C13—C14—C15—C16	177.4 (3)
O1i—Cu2—O4—C20	135.7 (3)	C14—C15—C16—C17	−1.4 (6)
O2i—Cu2—O4—C20	−149.7 (3)	C14—C15—C16—Cl2	177.8 (3)
O2—Cu2—O4—C20	30.3 (3)	C15—C16—C17—C18	1.4 (6)
O2—Cu1—N1—C7	23.8 (7)	Cl2—C16—C17—C18	−177.9 (3)
O1—Cu1—N1—C7	−24.2 (3)	C16—C17—C18—C19	−1.1 (5)
N2—Cu1—N1—C7	137.0 (3)	Cu1—O2—C19—C18	−159.7 (2)
O3—Cu1—N1—C7	−115.5 (3)	Cu2—O2—C19—C18	−16.4 (4)
O2—Cu1—N1—C8	−152.9 (5)	Cu1—O2—C19—C14	20.9 (4)
O1—Cu1—N1—C8	159.1 (2)	Cu2—O2—C19—C14	164.2 (2)
N2—Cu1—N1—C8	−39.6 (2)	C17—C18—C19—O2	−178.6 (3)
O3—Cu1—N1—C8	67.8 (2)	C17—C18—C19—C14	0.9 (5)
O2—Cu1—N2—C13	20.7 (3)	C15—C14—C19—O2	178.5 (3)
N1—Cu1—N2—C13	−149.5 (3)	C13—C14—C19—O2	2.5 (5)
O1—Cu1—N2—C13	−53.4 (5)	C15—C14—C19—C18	−0.9 (5)
O3—Cu1—N2—C13	111.5 (3)	C13—C14—C19—C18	−176.9 (3)
O2—Cu1—N2—C10	−157.9 (2)	Cu1—O3—C20—O4	0.0 (5)
N1—Cu1—N2—C10	31.9 (3)	Cu1—O3—C20—C21	179.9 (2)
O1—Cu1—N2—C10	128.0 (3)	Cu2—O4—C20—O3	6.2 (5)
O3—Cu1—N2—C10	−67.1 (3)	Cu2—O4—C20—C21	−173.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4i	0.93	2.58	3.115 (4)	117
C15—H15···O3ii	0.93	2.59	3.289 (4)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O4i	0.93	2.58	3.115 (4)	117
C15—H15⋯O3ii	0.93	2.59	3.289 (4)	133

Symmetry codes: (i) ; (ii) .