Bis{μ₃-cis-N-(2-carboxyl­ato-5-chloro­phen­yl)-N′-[3-(dimethyl­amino)­prop­yl]oxamidato(3−)}bis­(perchlorato-κO)bis­(N,N,N′,N′-tetra­methyl­ethylene­diamine)­tetra­copper(II)

Abstract

The title complex, [Cu₄(C₁₄H₁₅ClN₃O₄)₂(ClO₄)₂(C₆H₁₆N₂)₂], is a tetra­nuclear copper(II) complex lying about an inversion center wherein a cis-oxamide group is coordinated to both Cu atoms with bite angles of 84.45 (6) and 84.08 (10)°. Both Cu atoms adopt distorted square-pyramidal coordination geometries. The apical position of one Cu atom is occupied by an O atom from a perchlorate group, with a Cu—O bond length of 2.519 (7) Å, while the apical site of the other Cu atom is occupied by a carboxyl­ate O atom with a Cu—O distance of 2.281 (3) Å. The Cu atoms bridged by oxamide and carboxyl­ate-group bridges are separated by 5.204 (6) and 5.603 (2) Å, respectively. The crystal structure is consolidated by weak inter­molecular C—H⋯O inter­actions. Two perchlorate O atoms are disordered with unequal site-occupancy factors.

Related literature

For the preparation of the Na[Cu(oxbm)] ligand, see: Tao et al. (2003 ▶). For a related crystal structure, see: Zang et al. (2003 ▶).

Experimental

Crystal data

• [Cu₄(C₁₄H₁₅ClN₃O₄)₂(ClO₄)₂(C₆H₁₆N₂)₂]

• M _r = 1334.96

• Monoclinic,

• a = 12.5750 (13) Å

• b = 16.4137 (19) Å

• c = 14.1080 (15) Å

• β = 113.988 (2)°

• V = 2660.4 (5) ų

• Z = 2

• Mo Kα radiation

• μ = 1.85 mm⁻¹

• T = 298 K

• 0.49 × 0.48 × 0.20 mm

Data collection

• Bruker SMART CCD area-detector diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.464, T _max = 0.708

• 12993 measured reflections

• 4682 independent reflections

• 3287 reflections with I > 2σ(I)

• R _int = 0.052

Refinement

• R[F ² > 2σ(F ²)] = 0.044

• wR(F ²) = 0.133

• S = 1.00

• 4682 reflections

• 359 parameters

• H-atom parameters constrained

• Δρ_max = 0.65 e Å⁻³

• Δρ_min = −0.76 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O7i	0.93	2.58	3.26 (3)	129
C16—H16A⋯O8ii	0.97	2.46	3.41 (3)	168
C20—H20C⋯O2iii	0.96	2.54	3.139 (6)	121

Symmetry codes: (i) ; (ii) ; (iii) .

supplementary crystallographic information

Comment

The title compound, (Fig. 1), is a tetranuclear copper(II) complex lying about inversion centers wherein cis-oxamido group is coordinated to Cu1 and Cu2 in an usual mode with the bite angles of 84.45 (6) and 84.08 (10)°, respectively. Both Cu1 and Cu2 atoms adopt distorted square-pyramidal coordination geometries. The basal plane around Cu1 is defined by N1, N2, N3 and O1, with maximum displacement of 0.1050 (11) Å for N1 and the Cu1 lies 0.1298 (12) Å out of this plane. The apical position of Cu1 is occupied by O5 with Cu1—O5 bond length 2.519 (7) Å. Cu2 atom is coordinated by exo-cis oxygen atoms of the oxamido ligand (O3 and O4) and the nitrogen atoms (N4 and N5) of tetramethylethylenediamine ligand thus completing the basal plane, from which the maximum deviation of an atom (O4) being 0.1233 (8) Å; Cu2 is displaced from this basal plane by 0.1835 (6) Å. The apical site of Cu2 is occupied by a carboxyl oxygen atom (O2ⁱ where ⁱ = -x+1, -y+1, -z+1) with Cu2—O2ⁱ distance 2.281 (3) Å. The Cu—N bond lenghts in the title complex lie in the range 1.953 (3)-2.066 (3)Å and are close to the corresponding bond lenghts reported in a copper complex (Zang et al., 2003). The crystal structure is consolidated by weak intermolecular interactions of type C—H···O (Table 1).

Experimental

The Na[Cu(oxbm)] ligand, Na[Cu(oxamido-N-[3-N,N'-dimethylaminopropyl]-N'-(4-Chloro) -benzoato)], was prepared according to Tao et al., (2003). A methanol (10 ml) solution of Cu(ClO₄)₂^.6H₂O (0.742 g, 2 mmol) was added dropwise into a water solution (10 ml) of Na[Cu(oxbm)] (0.854 g, 2 mmol) with continuous stirring. The mixture was stirred for an hour and then tetramethylethylenediamine (0.0224 g, 2 mmol) in methanol (10 ml) was added dropwise. The solution obtained was stirred at 333 K for 10 h. The resulting solution was then filtered and the filtrate was allowed to stand at room temperature for three weeks to give well shaped green crystals of the title complex suitable for X-ray analysis.

Refinement

H atoms were positioned geometrically [0.93 (CH), 0.97 (CH₂) and 0.96 (CH₃)Å] and constrained to ride on their parent atoms with U_iso(H) =1.2(1.5 for methyl)U_eq(C). Two O-atoms of the perchlorate were disordered and their site occupancy factors were determined at earlier stages of refinement and were fixed at these occupancy factors during the final stages of refinements.

Figures

Fig. 1.

The molecular structure of (I) with 30% displacement ellipsoids (H atoms omitted for clarity). The symmetry code "A" in the atomic labels: -x+1, -y+1, -z+1.

Crystal data

[Cu4(C14H15ClN3O4)2(ClO4)2(C6H16N2)2]	F(000) = 1368
Mr = 1334.96	Dx = 1.666 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4604 reflections
a = 12.5750 (13) Å	θ = 2.2–27.7°
b = 16.4137 (19) Å	µ = 1.85 mm−1
c = 14.1080 (15) Å	T = 298 K
β = 113.988 (2)°	Block, green
V = 2660.4 (5) Å3	0.49 × 0.48 × 0.20 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	4682 independent reflections
Radiation source: fine-focus sealed tube	3287 reflections with I > 2σ(I)
graphite	Rint = 0.052
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→14
Tmin = 0.464, Tmax = 0.708	k = −19→19
12993 measured reflections	l = −16→14

Refinement

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.072P)2 + 1.0008P] where P = (Fo2 + 2Fc2)/3
4682 reflections	(Δ/σ)max = 0.001
359 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.76 e Å−3

Special details

Experimental. Yield, 58%; analysis, calculated for C40H62Cl4N10O16Cu4: C 35.99, H, 4.68; N 10.49%; found: C 35.96, H 4.69, N, 10.51%.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.28269 (4)	0.45069 (3)	0.33563 (4)	0.03039 (18)
Cu2	0.62990 (4)	0.24708 (3)	0.46234 (4)	0.03051 (18)
Cl1	0.79310 (12)	0.57100 (8)	0.29681 (13)	0.0599 (4)
Cl2	0.21665 (12)	0.38831 (7)	0.07826 (11)	0.0475 (3)
N1	0.4498 (3)	0.45347 (19)	0.3604 (3)	0.0243 (8)
N2	0.3096 (3)	0.3342 (2)	0.3638 (3)	0.0317 (9)
N3	0.1119 (3)	0.4486 (2)	0.3195 (3)	0.0315 (9)
N4	0.7940 (3)	0.2373 (2)	0.4680 (3)	0.0369 (10)
N5	0.6464 (3)	0.1307 (2)	0.5127 (3)	0.0324 (9)
O1	0.2790 (3)	0.56694 (18)	0.3491 (3)	0.0464 (9)
O2	0.3375 (3)	0.69384 (17)	0.3819 (3)	0.0403 (8)
O3	0.6008 (2)	0.35845 (17)	0.4019 (3)	0.0357 (8)
O4	0.4616 (3)	0.24340 (16)	0.4152 (3)	0.0345 (8)
O5	0.2228 (3)	0.4578 (2)	0.1424 (3)	0.0554 (10)
O6	0.1517 (4)	0.3248 (2)	0.0975 (4)	0.0762 (13)
O7	0.338 (3)	0.357 (2)	0.123 (4)	0.068 (5)	0.57
O8	0.190 (7)	0.4086 (18)	−0.022 (3)	0.082 (12)	0.57
O7'	0.322 (5)	0.363 (3)	0.081 (9)	0.076 (13)	0.43
O8'	0.143 (7)	0.415 (3)	−0.028 (4)	0.101 (13)	0.43
C1	0.3547 (4)	0.6219 (3)	0.3635 (3)	0.0316 (10)
C2	0.4679 (4)	0.6027 (2)	0.3540 (3)	0.0281 (10)
C3	0.5099 (3)	0.5233 (2)	0.3491 (3)	0.0253 (9)
C4	0.6111 (4)	0.5162 (3)	0.3307 (4)	0.0329 (11)
H4	0.6391	0.4649	0.3245	0.039*
C5	0.6689 (4)	0.5847 (3)	0.3218 (4)	0.0373 (11)
C6	0.6330 (4)	0.6620 (3)	0.3304 (4)	0.0405 (12)
H6	0.6746	0.7074	0.3256	0.049*
C7	0.5320 (4)	0.6699 (3)	0.3468 (4)	0.0348 (11)
H7	0.5061	0.7218	0.3531	0.042*
C8	0.4971 (4)	0.3808 (2)	0.3830 (3)	0.0274 (10)
C9	0.4166 (4)	0.3140 (2)	0.3888 (3)	0.0283 (10)
C10	0.2293 (4)	0.2683 (3)	0.3600 (5)	0.0467 (14)
H10A	0.2696	0.2291	0.4144	0.056*
H10B	0.2047	0.2404	0.2939	0.056*
C11	0.1226 (4)	0.2997 (3)	0.3737 (5)	0.0480 (13)
H11A	0.0699	0.2546	0.3659	0.058*
H11B	0.1466	0.3208	0.4435	0.058*
C12	0.0582 (4)	0.3660 (3)	0.2967 (4)	0.0430 (12)
H12A	0.0517	0.3496	0.2286	0.052*
H12B	−0.0201	0.3698	0.2937	0.052*
C13	0.0402 (4)	0.5036 (3)	0.2348 (4)	0.0489 (14)
H13A	0.0374	0.4834	0.1700	0.073*
H13B	0.0738	0.5572	0.2472	0.073*
H13C	−0.0373	0.5061	0.2322	0.073*
C14	0.1120 (5)	0.4791 (4)	0.4192 (5)	0.0569 (15)
H14A	0.1497	0.5313	0.4353	0.085*
H14B	0.1530	0.4413	0.4738	0.085*
H14C	0.0332	0.4844	0.4126	0.085*
C15	0.8213 (5)	0.1484 (3)	0.4798 (5)	0.0523 (14)
H15A	0.9049	0.1404	0.5088	0.063*
H15B	0.7881	0.1220	0.4125	0.063*
C16	0.7717 (4)	0.1115 (3)	0.5501 (5)	0.0500 (14)
H16A	0.7823	0.0528	0.5524	0.060*
H16B	0.8127	0.1326	0.6199	0.060*
C17	0.7999 (6)	0.2666 (4)	0.3708 (6)	0.077 (2)
H17A	0.7737	0.3221	0.3585	0.115*
H17B	0.7510	0.2332	0.3139	0.115*
H17C	0.8787	0.2634	0.3772	0.115*
C18	0.8777 (4)	0.2825 (4)	0.5567 (5)	0.0631 (17)
H18A	0.9546	0.2755	0.5593	0.095*
H18B	0.8753	0.2622	0.6197	0.095*
H18C	0.8577	0.3393	0.5493	0.095*
C19	0.5771 (4)	0.0761 (3)	0.4248 (4)	0.0449 (13)
H19A	0.6019	0.0830	0.3694	0.067*
H19B	0.4961	0.0897	0.4007	0.067*
H19C	0.5887	0.0205	0.4478	0.067*
C20	0.6059 (5)	0.1191 (3)	0.5964 (4)	0.0523 (14)
H20A	0.6208	0.0640	0.6212	0.078*
H20B	0.5239	0.1298	0.5700	0.078*
H20C	0.6467	0.1559	0.6523	0.078*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Cu1	0.0262 (3)	0.0263 (3)	0.0462 (4)	0.0015 (2)	0.0225 (3)	−0.0014 (2)
Cu2	0.0285 (3)	0.0249 (3)	0.0457 (4)	0.0043 (2)	0.0227 (3)	0.0056 (2)
Cl1	0.0542 (9)	0.0542 (8)	0.1007 (12)	0.0039 (7)	0.0617 (8)	0.0139 (8)
Cl2	0.0699 (9)	0.0377 (7)	0.0526 (8)	−0.0002 (6)	0.0430 (7)	0.0007 (6)
N1	0.0249 (19)	0.0217 (18)	0.031 (2)	0.0019 (15)	0.0163 (16)	0.0022 (15)
N2	0.027 (2)	0.0250 (18)	0.050 (2)	−0.0018 (16)	0.0230 (18)	0.0045 (17)
N3	0.0229 (19)	0.038 (2)	0.041 (2)	0.0017 (16)	0.0203 (17)	−0.0030 (17)
N4	0.032 (2)	0.034 (2)	0.054 (3)	0.0090 (17)	0.026 (2)	0.0059 (19)
N5	0.039 (2)	0.0243 (18)	0.036 (2)	0.0013 (17)	0.0172 (18)	0.0004 (16)
O1	0.0350 (19)	0.0281 (17)	0.087 (3)	0.0014 (15)	0.0353 (18)	−0.0093 (17)
O2	0.056 (2)	0.0250 (16)	0.057 (2)	0.0041 (15)	0.0403 (18)	−0.0023 (15)
O3	0.0270 (17)	0.0291 (16)	0.059 (2)	0.0048 (13)	0.0256 (15)	0.0134 (15)
O4	0.0277 (17)	0.0231 (16)	0.055 (2)	0.0021 (13)	0.0191 (15)	0.0086 (14)
O5	0.081 (3)	0.046 (2)	0.051 (2)	0.0051 (19)	0.039 (2)	−0.0035 (17)
O6	0.088 (3)	0.060 (3)	0.100 (4)	−0.019 (2)	0.058 (3)	−0.002 (2)
O7	0.081 (9)	0.068 (7)	0.082 (15)	0.019 (7)	0.061 (11)	0.005 (10)
O8	0.16 (3)	0.049 (8)	0.048 (14)	−0.002 (12)	0.056 (16)	0.000 (7)
O7'	0.074 (16)	0.071 (12)	0.11 (4)	−0.003 (10)	0.07 (2)	−0.012 (19)
O8'	0.13 (3)	0.082 (14)	0.055 (13)	0.019 (15)	−0.002 (14)	0.016 (9)
C1	0.042 (3)	0.030 (2)	0.032 (3)	0.001 (2)	0.025 (2)	0.000 (2)
C2	0.036 (3)	0.030 (2)	0.026 (2)	0.000 (2)	0.020 (2)	−0.0025 (18)
C3	0.029 (2)	0.026 (2)	0.027 (2)	−0.0018 (18)	0.0173 (19)	0.0029 (18)
C4	0.036 (3)	0.030 (2)	0.042 (3)	0.005 (2)	0.025 (2)	0.009 (2)
C5	0.036 (3)	0.043 (3)	0.046 (3)	0.002 (2)	0.030 (2)	0.009 (2)
C6	0.048 (3)	0.035 (3)	0.050 (3)	−0.005 (2)	0.033 (3)	0.006 (2)
C7	0.044 (3)	0.025 (2)	0.046 (3)	−0.001 (2)	0.028 (2)	0.000 (2)
C8	0.029 (2)	0.028 (2)	0.031 (2)	0.0000 (19)	0.019 (2)	0.0015 (18)
C9	0.030 (2)	0.028 (2)	0.036 (3)	0.0021 (19)	0.022 (2)	0.0031 (19)
C10	0.035 (3)	0.037 (3)	0.077 (4)	−0.007 (2)	0.031 (3)	0.006 (3)
C11	0.036 (3)	0.047 (3)	0.072 (4)	−0.006 (2)	0.032 (3)	0.007 (3)
C12	0.024 (2)	0.050 (3)	0.057 (3)	−0.004 (2)	0.019 (2)	−0.003 (3)
C13	0.033 (3)	0.056 (3)	0.065 (4)	0.012 (2)	0.027 (3)	0.015 (3)
C14	0.056 (4)	0.070 (4)	0.058 (4)	0.004 (3)	0.038 (3)	−0.012 (3)
C15	0.043 (3)	0.042 (3)	0.081 (4)	0.009 (2)	0.035 (3)	−0.006 (3)
C16	0.039 (3)	0.035 (3)	0.069 (4)	0.009 (2)	0.015 (3)	0.010 (3)
C17	0.066 (4)	0.095 (5)	0.094 (5)	0.017 (4)	0.059 (4)	0.027 (4)
C18	0.036 (3)	0.055 (3)	0.102 (5)	−0.003 (3)	0.032 (3)	−0.015 (3)
C19	0.049 (3)	0.033 (3)	0.052 (3)	−0.008 (2)	0.020 (3)	−0.004 (2)
C20	0.080 (4)	0.034 (3)	0.058 (4)	0.001 (3)	0.043 (3)	0.007 (2)

Geometric parameters (Å, °)

Cu1—O1	1.920 (3)	C4—C5	1.373 (6)
Cu1—N2	1.953 (3)	C4—H4	0.9300
Cu1—N1	1.986 (3)	C5—C6	1.368 (6)
Cu1—N3	2.066 (3)	C6—C7	1.385 (7)
Cu1—O5	2.518 (4)	C6—H6	0.9300
Cu2—O4	1.944 (3)	C7—H7	0.9300
Cu2—O3	1.987 (3)	C8—C9	1.516 (6)
Cu2—N5	2.020 (3)	C10—C11	1.521 (7)
Cu2—N4	2.039 (4)	C10—H10A	0.9700
Cu2—O2i	2.281 (3)	C10—H10B	0.9700
Cl1—C5	1.750 (5)	C11—C12	1.519 (7)
Cl2—O8	1.36 (4)	C11—H11A	0.9700
Cl2—O7'	1.37 (4)	C11—H11B	0.9700
Cl2—O6	1.417 (4)	C12—H12A	0.9700
Cl2—O5	1.439 (4)	C12—H12B	0.9700
Cl2—O8'	1.47 (4)	C13—H13A	0.9600
Cl2—O7	1.48 (3)	C13—H13B	0.9600
N1—C8	1.313 (5)	C13—H13C	0.9600
N1—C3	1.416 (5)	C14—H14A	0.9600
N2—C9	1.288 (5)	C14—H14B	0.9600
N2—C10	1.467 (5)	C14—H14C	0.9600
N3—C13	1.476 (6)	C15—C16	1.497 (8)
N3—C12	1.490 (6)	C15—H15A	0.9700
N3—C14	1.492 (6)	C15—H15B	0.9700
N4—C18	1.468 (7)	C16—H16A	0.9700
N4—C17	1.482 (7)	C16—H16B	0.9700
N4—C15	1.493 (6)	C17—H17A	0.9600
N5—C20	1.475 (6)	C17—H17B	0.9600
N5—C16	1.478 (6)	C17—H17C	0.9600
N5—C19	1.490 (6)	C18—H18A	0.9600
O1—C1	1.266 (5)	C18—H18B	0.9600
O2—C1	1.247 (5)	C18—H18C	0.9600
O2—Cu2i	2.281 (3)	C19—H19A	0.9600
O3—C8	1.275 (5)	C19—H19B	0.9600
O4—C9	1.278 (5)	C19—H19C	0.9600
C1—C2	1.517 (6)	C20—H20A	0.9600
C2—C7	1.394 (6)	C20—H20B	0.9600
C2—C3	1.418 (6)	C20—H20C	0.9600
C3—C4	1.404 (6)
O1—Cu1—N2	164.01 (16)	C5—C6—H6	121.3
O1—Cu1—N1	91.51 (13)	C7—C6—H6	121.3
N2—Cu1—N1	84.45 (13)	C6—C7—C2	122.3 (4)
O1—Cu1—N3	87.77 (13)	C6—C7—H7	118.8
N2—Cu1—N3	95.33 (14)	C2—C7—H7	118.8
N1—Cu1—N3	176.48 (14)	O3—C8—N1	129.5 (4)
O1—Cu1—O5	93.01 (14)	O3—C8—C9	115.4 (4)
N2—Cu1—O5	102.50 (14)	N1—C8—C9	115.1 (4)
N1—Cu1—O5	91.09 (14)	O4—C9—N2	127.1 (4)
N3—Cu1—O5	92.39 (14)	O4—C9—C8	116.4 (4)
O4—Cu2—O3	84.08 (11)	N2—C9—C8	116.4 (4)
O4—Cu2—N5	91.89 (13)	N2—C10—C11	112.0 (4)
O3—Cu2—N5	174.85 (13)	N2—C10—H10A	109.2
O4—Cu2—N4	162.63 (15)	C11—C10—H10A	109.2
O3—Cu2—N4	95.52 (13)	N2—C10—H10B	109.2
N5—Cu2—N4	87.36 (15)	C11—C10—H10B	109.2
O4—Cu2—O2i	95.00 (13)	H10A—C10—H10B	107.9
O3—Cu2—O2i	87.23 (12)	C12—C11—C10	113.2 (4)
N5—Cu2—O2i	96.35 (13)	C12—C11—H11A	108.9
N4—Cu2—O2i	102.33 (14)	C10—C11—H11A	108.9
O8—Cl2—O7'	86 (2)	C12—C11—H11B	108.9
O8—Cl2—O6	118 (2)	C10—C11—H11B	108.9
O7'—Cl2—O6	113 (3)	H11A—C11—H11B	107.7
O8—Cl2—O5	112.9 (13)	N3—C12—C11	115.8 (4)
O7'—Cl2—O5	114 (3)	N3—C12—H12A	108.3
O6—Cl2—O5	110.6 (3)	C11—C12—H12A	108.3
O7'—Cl2—O8'	109.0 (19)	N3—C12—H12B	108.3
O6—Cl2—O8'	104 (3)	C11—C12—H12B	108.3
O5—Cl2—O8'	105 (3)	H12A—C12—H12B	107.4
O8—Cl2—O7	107.8 (17)	N3—C13—H13A	109.5
O6—Cl2—O7	103.5 (14)	N3—C13—H13B	109.5
O5—Cl2—O7	102.8 (17)	H13A—C13—H13B	109.5
O8'—Cl2—O7	131 (3)	N3—C13—H13C	109.5
C8—N1—C3	123.6 (4)	H13A—C13—H13C	109.5
C8—N1—Cu1	111.3 (3)	H13B—C13—H13C	109.5
C3—N1—Cu1	125.0 (3)	N3—C14—H14A	109.5
C9—N2—C10	116.6 (4)	N3—C14—H14B	109.5
C9—N2—Cu1	112.5 (3)	H14A—C14—H14B	109.5
C10—N2—Cu1	130.9 (3)	N3—C14—H14C	109.5
C13—N3—C12	107.9 (4)	H14A—C14—H14C	109.5
C13—N3—C14	108.9 (4)	H14B—C14—H14C	109.5
C12—N3—C14	109.6 (4)	N4—C15—C16	109.4 (4)
C13—N3—Cu1	110.2 (3)	N4—C15—H15A	109.8
C12—N3—Cu1	113.5 (3)	C16—C15—H15A	109.8
C14—N3—Cu1	106.8 (3)	N4—C15—H15B	109.8
C18—N4—C17	109.7 (5)	C16—C15—H15B	109.8
C18—N4—C15	110.3 (4)	H15A—C15—H15B	108.3
C17—N4—C15	109.0 (4)	N5—C16—C15	110.3 (4)
C18—N4—Cu2	110.8 (3)	N5—C16—H16A	109.6
C17—N4—Cu2	111.6 (3)	C15—C16—H16A	109.6
C15—N4—Cu2	105.3 (3)	N5—C16—H16B	109.6
C20—N5—C16	110.6 (4)	C15—C16—H16B	109.6
C20—N5—C19	108.2 (4)	H16A—C16—H16B	108.1
C16—N5—C19	110.3 (4)	N4—C17—H17A	109.5
C20—N5—Cu2	112.6 (3)	N4—C17—H17B	109.5
C16—N5—Cu2	105.6 (3)	H17A—C17—H17B	109.5
C19—N5—Cu2	109.5 (3)	N4—C17—H17C	109.5
C1—O1—Cu1	132.6 (3)	H17A—C17—H17C	109.5
C1—O2—Cu2i	128.7 (3)	H17B—C17—H17C	109.5
C8—O3—Cu2	110.4 (3)	N4—C18—H18A	109.5
C9—O4—Cu2	111.3 (3)	N4—C18—H18B	109.5
Cl2—O5—Cu1	124.0 (2)	H18A—C18—H18B	109.5
O2—C1—O1	121.7 (4)	N4—C18—H18C	109.5
O2—C1—C2	117.6 (4)	H18A—C18—H18C	109.5
O1—C1—C2	120.6 (4)	H18B—C18—H18C	109.5
C7—C2—C3	119.1 (4)	N5—C19—H19A	109.5
C7—C2—C1	115.7 (4)	N5—C19—H19B	109.5
C3—C2—C1	125.2 (4)	H19A—C19—H19B	109.5
C4—C3—N1	121.3 (4)	N5—C19—H19C	109.5
C4—C3—C2	117.9 (4)	H19A—C19—H19C	109.5
N1—C3—C2	120.8 (4)	H19B—C19—H19C	109.5
C5—C4—C3	120.2 (4)	N5—C20—H20A	109.5
C5—C4—H4	119.9	N5—C20—H20B	109.5
C3—C4—H4	119.9	H20A—C20—H20B	109.5
C6—C5—C4	123.0 (4)	N5—C20—H20C	109.5
C6—C5—Cl1	119.5 (4)	H20A—C20—H20C	109.5
C4—C5—Cl1	117.5 (4)	H20B—C20—H20C	109.5
C5—C6—C7	117.4 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O7ii	0.93	2.58	3.26 (3)	129
C16—H16A···O8iii	0.97	2.46	3.41 (3)	168
C20—H20C···O2i	0.96	2.54	3.139 (6)	121
C4—H4···O3	0.93	2.21	2.799 (5)	120
C7—H7···O2	0.93	2.36	2.714 (6)	102
C13—H13A···O5	0.96	2.55	3.158 (7)	121
C13—H13B···O1	0.96	2.39	2.960 (6)	118
C14—H14A···O1	0.96	2.46	3.026 (7)	117
C17—H17A···O3	0.96	2.56	3.103 (7)	116
C19—H19B···O4	0.96	2.58	3.084 (6)	113

Symmetry codes: (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2; (i) −x+1, −y+1, −z+1.