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Acta Cryst. (2008). E64, m1133    [ doi:10.1107/S1600536808024707 ]

Bis{[mu]-5-(diethylamino)-2-[(2-oxidoethoxy)iminomethyl]phenolato}dicopper(II) acetone solvate

W.-K. Dong, X. Chen, X.-N. He, X.-L. Tang and Z.-W. Lv

Abstract top

The title complex, [Cu2(C13H18N2O3)2]·C3H6O, has been synthesized by the reaction of copper(II) acetate monohydrate with 5,5'-bis(diethylamino)-2,2'-[ethylenedioxybis(nitrilomethylidyne)]diphenol, where one of the N-O bonds of the ligand was cleaved during the reaction. The complex molecule has a [mu]-dialkoxo-bridged binuclear structure with both CuII centers exhibiting a square-planar coordination geometry.

Comment top

Several works have been devoted to synthesize and characterize transition metal complexes bearing a salen-type bisoxime ligand or its derivatives (Dong et al., 2007a; Dong et al., 2007b).

The title compound has been synthesized by the reaction of copper(II) acetate monohydrate with a salen-type bisoxime ligand, 5,5'-di(N,N'-diethylamino)-2,2' -[ethylenedioxybis(nitrilomethylidyne)]diphenol (H2L1). The catalytic action of CuII ions resulted in unexpected cleavage of one of the N—O bonds in the ligand H2L1 (Bu et al., 1990) giving a novel dialkoxo-bridged dinuclear complex with a Cu—O—Cu—O four-membered ring core, instead of the expected salen-type bisoxime Cu—N2O2 complex (Sun et al., 2008).

The title molecule has µ-dialkoxo bridged binuclear structure with both CuII centers tetra-coordinated, where oxime nitrogen atom, phenoxo oxygen atom and two bridging alkoxo oxygen atoms act as donors. The Cu2O2 core is formed by two CuII ions and two bridging alkoxo oxygen atoms with Cu—Cu separation of 3.0051 (12) Å. The dihedral angle between the two planes, O2—Cu2—O5 and O2—Cu1—O5, is 8.80 (4)°.

Related literature top

For related literature, see: Bu et al. (1990); Dong et al. (2007a,b); Sun et al. (2008); Zhang et al. (2007).

Experimental top

5, 5'-Di(N,N'-diethylamino)-2,2'- [ethylenedioxybis(nitrilomethylidyne)]diphenol (H2L1) was synthesized according to previously reported procedure (Zhang et al., 2007). A solution of copper(II) acetate monohydrate (20.0 mg, 0.1 mmol) in ethanol (15 ml) was added dropwise to a solution of H2L1 (44.3 mg, 0.1 mmol) in acetone (15 ml) at room temperature. The color of the mixing solution turned to brown immediately. The solution was stirred for 4 h at room temperature and then filtered. The filtrate was allowed to evaporate at room temperature for about three weeks and dark-brown prismatic single crystals suitable for X-ray crystallographic analysis were obtained. Anal. Calcd. for C29H42Cu2N4O7 {[Cu2(L2)2]C3H6O} (%): C, 50.79; H, 6.17; N, 8.17; Cu, 18.53. Found: C, 50.61; H, 6.19; N, 8.01; Cu, 18.29. IR: νC=N, 1614 cm-1 and νAr-O, 1235 cm-1.

Refinement top

H atoms were placed at calculated positions [C—H = 0.96 (CH3), 0.97 Å (CH2), 0.93 Å (CH)] and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atom numbering scheme. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
Bis{µ-5-(diethylamino)-2-[(2-oxidoethoxy)iminomethyl]phenolato}dicopper(II) acetone solvate top
Crystal data top
[Cu2(C13H18N2O3)2]·C3H6OF000 = 1432
Mr = 685.75Dx = 1.491 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2917 reflections
a = 20.633 (3) Åθ = 2.4–22.9º
b = 11.6045 (14) ŵ = 1.44 mm−1
c = 13.0738 (17) ÅT = 298 (2) K
β = 102.635 (2)ºPrismatic, dark-brown
V = 3054.6 (7) Å30.53 × 0.49 × 0.47 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD
diffractometer		5363 independent reflections
Radiation source: fine-focus sealed tube2967 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.092
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 2.0º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −23→24
Tmin = 0.515, Tmax = 0.550k = −13→9
14726 measured reflectionsl = −15→15
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.075H-atom parameters constrained
wR(F2) = 0.229  w = 1/[σ2(Fo2) + (0.1245P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
5363 reflectionsΔρmax = 0.88 e Å−3
385 parametersΔρmin = −1.06 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Cu2(C13H18N2O3)2]·C3H6OV = 3054.6 (7) Å3
Mr = 685.75Z = 4
Monoclinic, P21/cMo Kα
a = 20.633 (3) ŵ = 1.44 mm−1
b = 11.6045 (14) ÅT = 298 (2) K
c = 13.0738 (17) Å0.53 × 0.49 × 0.47 mm
β = 102.635 (2)º
Data collection top
Bruker SMART 1000 CCD
diffractometer		5363 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2967 reflections with I > 2σ(I)
Tmin = 0.515, Tmax = 0.550Rint = 0.092
14726 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.075385 parameters
wR(F2) = 0.229H-atom parameters constrained
S = 1.00Δρmax = 0.88 e Å−3
5363 reflectionsΔρmin = −1.06 e Å−3
Special details top

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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.50062 (4)0.85967 (8)0.08317 (7)0.0325 (3)
Cu20.40492 (4)0.91965 (8)0.21830 (7)0.0350 (3)
N10.4892 (3)0.7990 (5)−0.0554 (5)0.0362 (15)
N20.8064 (3)0.8744 (7)0.0240 (6)0.061 (2)
N30.4087 (3)1.0305 (6)0.3279 (5)0.0419 (16)
N40.0932 (4)0.9250 (8)0.2481 (7)0.075 (3)
O10.4275 (2)0.7535 (4)−0.1126 (4)0.0392 (13)
O20.4116 (2)0.8328 (5)0.0968 (4)0.0412 (13)
O30.5922 (2)0.8847 (4)0.0975 (4)0.0398 (13)
O40.4662 (2)1.0969 (4)0.3692 (4)0.0447 (14)
O50.4970 (2)0.9318 (4)0.2158 (4)0.0395 (13)
O60.3153 (2)0.8842 (5)0.2103 (4)0.0456 (14)
O70.1481 (6)0.5560 (10)0.0993 (9)0.154 (4)
C10.3732 (3)0.8175 (7)−0.0905 (6)0.0398 (19)
H1A0.33370.7991−0.14330.048*
H1B0.38220.8990−0.09680.048*
C20.3591 (3)0.7965 (7)0.0148 (6)0.042 (2)
H2A0.31890.83730.01990.051*
H2B0.35130.71490.02260.051*
C30.5347 (3)0.7810 (6)−0.1079 (6)0.0386 (18)
H30.52220.7487−0.17440.046*
C40.6025 (3)0.8082 (7)−0.0690 (6)0.0389 (18)
C50.6286 (4)0.8589 (7)0.0283 (6)0.0413 (19)
C60.6954 (4)0.8808 (7)0.0556 (7)0.048 (2)
H60.71280.91470.12030.058*
C70.7386 (4)0.8539 (8)−0.0103 (7)0.051 (2)
C80.7128 (4)0.8060 (7)−0.1067 (7)0.050 (2)
H80.74050.7888−0.15200.060*
C90.6464 (3)0.7839 (7)−0.1356 (6)0.044 (2)
H90.62930.7518−0.20120.053*
C100.8505 (4)0.8597 (8)−0.0509 (8)0.064 (3)
H10A0.82550.8780−0.12090.077*
H10B0.88680.9143−0.03340.077*
C110.8781 (5)0.7429 (9)−0.0516 (8)0.080 (3)
H11A0.90470.72550.01650.120*
H11B0.90510.7389−0.10260.120*
H11C0.84250.6882−0.06900.120*
C120.8390 (5)0.9014 (9)0.1339 (8)0.072 (3)
H12A0.81520.86720.18270.087*
H12B0.88470.87500.15060.087*
C130.8354 (6)1.0267 (10)0.1358 (10)0.097 (4)
H13A0.85041.05760.07690.146*
H13B0.86311.05500.19960.146*
H13C0.79031.05000.13210.146*
C140.5245 (3)1.0263 (7)0.3815 (6)0.0422 (19)
H14A0.51660.95440.41470.051*
H14B0.56111.06520.42800.051*
C150.5443 (3)0.9998 (7)0.2812 (6)0.0397 (19)
H15A0.54981.07130.24560.048*
H15B0.58660.95990.29600.048*
C160.3585 (4)1.0680 (7)0.3631 (7)0.049 (2)
H160.36651.12650.41280.058*
C170.2923 (4)1.0267 (7)0.3318 (7)0.048 (2)
C180.2740 (4)0.9378 (8)0.2589 (7)0.051 (2)
C190.2075 (4)0.9048 (8)0.2342 (7)0.059 (3)
H190.19540.84290.18890.071*
C200.1578 (4)0.9599 (9)0.2739 (8)0.065 (3)
C210.1795 (5)1.0508 (8)0.3459 (8)0.066 (3)
H210.14871.08880.37610.079*
C220.2412 (4)1.0817 (8)0.3705 (7)0.057 (2)
H220.25271.14360.41610.069*
C230.0379 (5)1.0076 (11)0.2675 (10)0.087 (3)
H23A0.05331.08680.27280.104*
H23B−0.00131.00200.21120.104*
C240.0237 (6)0.9686 (12)0.3669 (10)0.110 (4)
H24A0.00750.89080.35950.165*
H24B−0.00931.01770.38560.165*
H24C0.06360.97180.42080.165*
C250.0727 (5)0.8171 (10)0.1932 (10)0.083 (3)
H25A0.10890.76200.20830.100*
H25B0.03520.78480.21700.100*
C260.0544 (6)0.8385 (12)0.0819 (10)0.109 (4)
H26A0.01380.88180.06590.164*
H26B0.04820.76640.04500.164*
H26C0.08900.88150.06070.164*
C270.2690 (8)0.5540 (14)0.1403 (14)0.151 (6)
H27A0.29450.61700.17610.226*
H27B0.29140.52250.08940.226*
H27C0.26450.49540.19010.226*
C280.2039 (10)0.5947 (16)0.0880 (15)0.139 (6)
C290.1968 (7)0.6857 (14)0.0057 (12)0.135 (5)
H29A0.15140.6892−0.03230.202*
H29B0.22490.6678−0.04170.202*
H29C0.20950.75890.03820.202*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0317 (5)0.0379 (6)0.0287 (5)−0.0031 (4)0.0086 (4)−0.0046 (4)
Cu20.0319 (5)0.0410 (6)0.0332 (6)−0.0024 (4)0.0093 (4)−0.0071 (4)
N10.030 (3)0.043 (4)0.036 (4)−0.004 (3)0.010 (3)−0.005 (3)
N20.047 (4)0.071 (5)0.067 (6)0.000 (4)0.018 (4)−0.004 (4)
N30.036 (3)0.045 (4)0.047 (4)−0.005 (3)0.014 (3)−0.010 (3)
N40.057 (5)0.081 (6)0.090 (7)−0.005 (5)0.025 (5)−0.023 (5)
O10.034 (3)0.046 (3)0.038 (3)−0.003 (2)0.009 (2)−0.014 (3)
O20.034 (3)0.052 (3)0.039 (3)−0.006 (2)0.012 (2)−0.011 (3)
O30.034 (3)0.047 (3)0.041 (3)−0.007 (2)0.013 (2)−0.010 (3)
O40.042 (3)0.042 (3)0.050 (4)−0.008 (3)0.011 (3)−0.011 (3)
O50.035 (3)0.048 (3)0.037 (3)−0.008 (2)0.013 (2)−0.011 (3)
O60.038 (3)0.051 (3)0.050 (4)−0.004 (3)0.015 (3)−0.017 (3)
O70.137 (9)0.164 (11)0.162 (11)−0.028 (8)0.036 (8)−0.006 (8)
C10.033 (4)0.046 (5)0.038 (5)−0.004 (4)0.005 (3)−0.007 (4)
C20.035 (4)0.051 (5)0.041 (5)−0.004 (4)0.009 (3)−0.011 (4)
C30.036 (4)0.042 (5)0.038 (5)−0.003 (4)0.010 (3)−0.003 (4)
C40.036 (4)0.043 (5)0.041 (5)−0.001 (4)0.014 (3)−0.004 (4)
C50.036 (4)0.045 (5)0.046 (5)−0.001 (4)0.015 (4)−0.005 (4)
C60.039 (5)0.055 (5)0.052 (5)−0.005 (4)0.015 (4)−0.004 (4)
C70.041 (5)0.057 (6)0.059 (6)−0.003 (4)0.017 (4)−0.004 (5)
C80.042 (5)0.058 (6)0.055 (6)0.000 (4)0.019 (4)−0.003 (5)
C90.041 (4)0.048 (5)0.045 (5)0.001 (4)0.014 (4)−0.003 (4)
C100.049 (5)0.074 (7)0.072 (7)−0.001 (5)0.020 (5)−0.002 (6)
C110.066 (6)0.085 (8)0.092 (8)0.011 (6)0.026 (6)0.006 (7)
C120.053 (6)0.087 (8)0.078 (8)−0.004 (6)0.017 (5)−0.007 (6)
C130.090 (8)0.088 (9)0.111 (11)−0.004 (7)0.017 (7)−0.006 (8)
C140.038 (4)0.044 (5)0.043 (5)−0.008 (4)0.006 (4)−0.008 (4)
C150.034 (4)0.044 (5)0.040 (5)−0.010 (4)0.008 (3)−0.009 (4)
C160.045 (5)0.050 (5)0.053 (6)−0.002 (4)0.017 (4)−0.014 (4)
C170.043 (5)0.052 (5)0.054 (6)−0.005 (4)0.022 (4)−0.016 (5)
C180.044 (5)0.058 (6)0.058 (6)−0.003 (4)0.023 (4)−0.014 (5)
C190.049 (5)0.064 (6)0.069 (7)−0.005 (5)0.024 (5)−0.017 (5)
C200.053 (6)0.071 (7)0.076 (7)−0.006 (5)0.023 (5)−0.018 (6)
C210.055 (6)0.071 (7)0.077 (7)−0.003 (5)0.027 (5)−0.020 (6)
C220.050 (5)0.060 (6)0.065 (6)−0.004 (5)0.023 (5)−0.019 (5)
C230.069 (7)0.096 (9)0.098 (10)−0.007 (6)0.025 (6)−0.018 (7)
C240.097 (9)0.115 (11)0.116 (12)−0.014 (8)0.019 (8)−0.015 (9)
C250.063 (7)0.092 (9)0.100 (10)−0.008 (6)0.027 (6)−0.021 (8)
C260.097 (9)0.118 (11)0.108 (12)−0.006 (8)0.013 (8)−0.005 (9)
C270.123 (13)0.170 (18)0.157 (17)−0.019 (12)0.025 (12)0.007 (13)
C280.128 (14)0.151 (16)0.145 (16)−0.031 (13)0.047 (13)0.010 (12)
C290.125 (12)0.144 (14)0.135 (14)−0.020 (11)0.028 (10)−0.008 (12)
Geometric parameters (Å, °) top
Cu1—O31.880 (5)C11—H11A0.9600
Cu1—O21.909 (5)C11—H11B0.9600
Cu1—N11.910 (6)C11—H11C0.9600
Cu1—O51.942 (5)C12—C131.456 (14)
Cu1—Cu23.0051 (12)C12—H12A0.9700
Cu2—O61.874 (5)C12—H12B0.9700
Cu2—O21.911 (5)C13—H13A0.9600
Cu2—O51.912 (5)C13—H13B0.9600
Cu2—N31.914 (6)C13—H13C0.9600
N1—C31.295 (8)C14—C151.488 (10)
N1—O11.428 (7)C14—H14A0.9700
N2—C71.394 (10)C14—H14B0.9700
N2—C121.480 (12)C15—H15A0.9700
N2—C101.485 (11)C15—H15B0.9700
N3—C161.297 (9)C16—C171.421 (11)
N3—O41.419 (7)C16—H160.9300
N4—C201.363 (11)C17—C181.400 (11)
N4—C251.459 (13)C17—C221.416 (10)
N4—C231.552 (12)C18—C191.392 (11)
O1—C11.425 (8)C19—C201.401 (11)
O2—C21.412 (8)C19—H190.9300
O3—C51.330 (8)C20—C211.419 (13)
O4—C141.435 (8)C21—C221.295 (11)
O5—C151.393 (8)C21—H210.9300
O6—C181.324 (8)C22—H220.9300
O7—C281.275 (16)C23—C241.465 (14)
C1—C21.488 (10)C23—H23A0.9700
C1—H1A0.9700C23—H23B0.9700
C1—H1B0.9700C24—H24A0.9600
C2—H2A0.9700C24—H24B0.9600
C2—H2B0.9700C24—H24C0.9600
C3—C41.417 (10)C25—C261.442 (15)
C3—H30.9300C25—H25A0.9700
C4—C51.398 (11)C25—H25B0.9700
C4—C91.415 (10)C26—H26A0.9600
C5—C61.371 (10)C26—H26B0.9600
C6—C71.403 (11)C26—H26C0.9600
C6—H60.9300C27—C281.45 (2)
C7—C81.374 (12)C27—H27A0.9600
C8—C91.365 (10)C27—H27B0.9600
C8—H80.9300C27—H27C0.9600
C9—H90.9300C28—C291.49 (2)
C10—C111.470 (13)C29—H29A0.9600
C10—H10A0.9700C29—H29B0.9600
C10—H10B0.9700C29—H29C0.9600
O3—Cu1—O2169.2 (2)H11B—C11—H11C109.5
O3—Cu1—N193.7 (2)C13—C12—N2102.3 (9)
O2—Cu1—N196.1 (2)C13—C12—H12A111.3
O3—Cu1—O594.5 (2)N2—C12—H12A111.3
O2—Cu1—O576.2 (2)C13—C12—H12B111.3
N1—Cu1—O5170.1 (2)N2—C12—H12B111.3
O3—Cu1—Cu2132.92 (15)H12A—C12—H12B109.2
O2—Cu1—Cu238.15 (15)C12—C13—H13A109.5
N1—Cu1—Cu2133.02 (17)C12—C13—H13B109.5
O5—Cu1—Cu238.40 (13)H13A—C13—H13B109.5
O6—Cu2—O295.0 (2)C12—C13—H13C109.5
O6—Cu2—O5170.6 (2)H13A—C13—H13C109.5
O2—Cu2—O576.8 (2)H13B—C13—H13C109.5
O6—Cu2—N393.9 (2)O4—C14—C15113.7 (6)
O2—Cu2—N3167.9 (2)O4—C14—H14A108.8
O5—Cu2—N394.9 (2)C15—C14—H14A108.8
O6—Cu2—Cu1133.10 (16)O4—C14—H14B108.8
O2—Cu2—Cu138.11 (14)C15—C14—H14B108.8
O5—Cu2—Cu139.11 (14)H14A—C14—H14B107.7
N3—Cu2—Cu1132.15 (18)O5—C15—C14111.6 (6)
C3—N1—O1109.2 (6)O5—C15—H15A109.3
C3—N1—Cu1127.5 (5)C14—C15—H15A109.3
O1—N1—Cu1123.0 (4)O5—C15—H15B109.3
C7—N2—C12124.0 (7)C14—C15—H15B109.3
C7—N2—C10119.0 (8)H15A—C15—H15B108.0
C12—N2—C10116.8 (7)N3—C16—C17125.3 (8)
C16—N3—O4110.4 (6)N3—C16—H16117.4
C16—N3—Cu2125.9 (6)C17—C16—H16117.4
O4—N3—Cu2122.9 (4)C18—C17—C22117.7 (7)
C20—N4—C25122.6 (8)C18—C17—C16122.9 (7)
C20—N4—C23119.3 (8)C22—C17—C16119.3 (8)
C25—N4—C23117.8 (8)O6—C18—C19117.7 (8)
C1—O1—N1110.6 (5)O6—C18—C17124.5 (7)
C2—O2—Cu1124.9 (4)C19—C18—C17117.8 (7)
C2—O2—Cu2127.3 (4)C18—C19—C20123.6 (9)
Cu1—O2—Cu2103.7 (2)C18—C19—H19118.2
C5—O3—Cu1127.0 (5)C20—C19—H19118.2
N3—O4—C14110.0 (5)N4—C20—C19121.9 (9)
C15—O5—Cu2126.6 (4)N4—C20—C21122.3 (8)
C15—O5—Cu1129.3 (4)C19—C20—C21115.8 (8)
Cu2—O5—Cu1102.5 (2)C22—C21—C20121.4 (9)
C18—O6—Cu2126.9 (5)C22—C21—H21119.3
O1—C1—C2115.1 (6)C20—C21—H21119.3
O1—C1—H1A108.5C21—C22—C17123.7 (9)
C2—C1—H1A108.5C21—C22—H22118.2
O1—C1—H1B108.5C17—C22—H22118.2
C2—C1—H1B108.5C24—C23—N4104.5 (10)
H1A—C1—H1B107.5C24—C23—H23A110.8
O2—C2—C1112.4 (6)N4—C23—H23A110.8
O2—C2—H2A109.1C24—C23—H23B110.8
C1—C2—H2A109.1N4—C23—H23B110.8
O2—C2—H2B109.1H23A—C23—H23B108.9
C1—C2—H2B109.1C23—C24—H24A109.5
H2A—C2—H2B107.9C23—C24—H24B109.5
N1—C3—C4123.2 (7)H24A—C24—H24B109.5
N1—C3—H3118.4C23—C24—H24C109.5
C4—C3—H3118.4H24A—C24—H24C109.5
C5—C4—C9118.3 (7)H24B—C24—H24C109.5
C5—C4—C3125.0 (7)C26—C25—N4109.4 (11)
C9—C4—C3116.7 (7)C26—C25—H25A109.8
O3—C5—C6117.8 (7)N4—C25—H25A109.8
O3—C5—C4123.5 (7)C26—C25—H25B109.8
C6—C5—C4118.7 (7)N4—C25—H25B109.8
C5—C6—C7122.4 (8)H25A—C25—H25B108.2
C5—C6—H6118.8C25—C26—H26A109.5
C7—C6—H6118.8C25—C26—H26B109.5
C8—C7—N2121.6 (8)H26A—C26—H26B109.5
C8—C7—C6118.9 (8)C25—C26—H26C109.5
N2—C7—C6119.5 (8)H26A—C26—H26C109.5
C9—C8—C7119.6 (8)H26B—C26—H26C109.5
C9—C8—H8120.2C28—C27—H27A109.5
C7—C8—H8120.2C28—C27—H27B109.5
C8—C9—C4122.1 (8)H27A—C27—H27B109.5
C8—C9—H9119.0C28—C27—H27C109.5
C4—C9—H9119.0H27A—C27—H27C109.5
C11—C10—N2113.8 (8)H27B—C27—H27C109.5
C11—C10—H10A108.8O7—C28—C27126.8 (18)
N2—C10—H10A108.8O7—C28—C29112.6 (17)
C11—C10—H10B108.8C27—C28—C29120.5 (16)
N2—C10—H10B108.8C28—C29—H29A109.5
H10A—C10—H10B107.7C28—C29—H29B109.5
C10—C11—H11A109.5H29A—C29—H29B109.5
C10—C11—H11B109.5C28—C29—H29C109.5
H11A—C11—H11B109.5H29A—C29—H29C109.5
C10—C11—H11C109.5H29B—C29—H29C109.5
H11A—C11—H11C109.5
O3—Cu1—Cu2—O6−173.8 (3)N1—O1—C1—C2−73.6 (8)
O2—Cu1—Cu2—O6−2.9 (3)Cu1—O2—C2—C1−18.9 (9)
N1—Cu1—Cu2—O614.9 (4)Cu2—O2—C2—C1134.5 (6)
O5—Cu1—Cu2—O6−172.3 (3)O1—C1—C2—O264.6 (9)
O3—Cu1—Cu2—O2−170.9 (3)O1—N1—C3—C4−175.2 (7)
N1—Cu1—Cu2—O217.8 (4)Cu1—N1—C3—C4−1.9 (11)
O5—Cu1—Cu2—O2−169.3 (4)N1—C3—C4—C5−1.2 (13)
O3—Cu1—Cu2—O5−1.6 (3)N1—C3—C4—C9−179.8 (7)
O2—Cu1—Cu2—O5169.3 (4)Cu1—O3—C5—C6−177.8 (5)
N1—Cu1—Cu2—O5−172.8 (4)Cu1—O3—C5—C40.5 (11)
O3—Cu1—Cu2—N319.7 (4)C9—C4—C5—O3−179.4 (7)
O2—Cu1—Cu2—N3−169.3 (4)C3—C4—C5—O32.0 (13)
N1—Cu1—Cu2—N3−151.5 (4)C9—C4—C5—C6−1.2 (12)
O5—Cu1—Cu2—N321.3 (4)C3—C4—C5—C6−179.8 (8)
O3—Cu1—N1—C33.2 (7)O3—C5—C6—C7178.2 (7)
O2—Cu1—N1—C3−172.3 (7)C4—C5—C6—C7−0.2 (13)
Cu2—Cu1—N1—C3176.8 (5)C12—N2—C7—C8−166.2 (9)
O3—Cu1—N1—O1175.6 (5)C10—N2—C7—C88.8 (13)
O2—Cu1—N1—O10.1 (5)C12—N2—C7—C612.7 (13)
Cu2—Cu1—N1—O1−10.8 (7)C10—N2—C7—C6−172.3 (8)
O6—Cu2—N3—C16−8.1 (7)C5—C6—C7—C81.4 (14)
O2—Cu2—N3—C16129.1 (11)C5—C6—C7—N2−177.5 (8)
O5—Cu2—N3—C16175.3 (7)N2—C7—C8—C9177.8 (8)
Cu1—Cu2—N3—C16162.0 (6)C6—C7—C8—C9−1.1 (13)
O6—Cu2—N3—O4−177.0 (5)C7—C8—C9—C4−0.3 (13)
O2—Cu2—N3—O4−39.8 (15)C5—C4—C9—C81.5 (12)
O5—Cu2—N3—O46.4 (6)C3—C4—C9—C8−179.8 (7)
Cu1—Cu2—N3—O4−6.9 (7)C7—N2—C10—C11−90.6 (11)
C3—N1—O1—C1−150.4 (6)C12—N2—C10—C1184.7 (11)
Cu1—N1—O1—C136.0 (7)C7—N2—C12—C13−90.3 (10)
O3—Cu1—O2—C2−163.5 (10)C10—N2—C12—C1394.6 (10)
N1—Cu1—O2—C2−8.5 (6)N3—O4—C14—C1575.3 (7)
O5—Cu1—O2—C2165.3 (6)Cu2—O5—C15—C1423.7 (9)
Cu2—Cu1—O2—C2158.5 (7)Cu1—O5—C15—C14−173.3 (5)
O3—Cu1—O2—Cu238.0 (13)O4—C14—C15—O5−65.7 (9)
N1—Cu1—O2—Cu2−167.0 (3)O4—N3—C16—C17175.1 (8)
O5—Cu1—O2—Cu26.8 (2)Cu2—N3—C16—C175.1 (13)
O6—Cu2—O2—C220.1 (6)N3—C16—C17—C181.0 (15)
O5—Cu2—O2—C2−164.7 (6)N3—C16—C17—C22−175.1 (8)
N3—Cu2—O2—C2−117.0 (12)Cu2—O6—C18—C19173.8 (6)
Cu1—Cu2—O2—C2−157.8 (7)Cu2—O6—C18—C17−5.0 (13)
O6—Cu2—O2—Cu1177.9 (3)C22—C17—C18—O6175.0 (8)
O5—Cu2—O2—Cu1−6.9 (2)C16—C17—C18—O6−1.2 (15)
N3—Cu2—O2—Cu140.8 (13)C22—C17—C18—C19−3.8 (13)
O2—Cu1—O3—C5152.7 (11)C16—C17—C18—C19−179.9 (9)
N1—Cu1—O3—C5−2.4 (6)O6—C18—C19—C20−175.2 (9)
O5—Cu1—O3—C5−177.0 (6)C17—C18—C19—C203.6 (15)
Cu2—Cu1—O3—C5−176.0 (5)C25—N4—C20—C1911.0 (16)
C16—N3—O4—C14148.0 (7)C23—N4—C20—C19−162.8 (10)
Cu2—N3—O4—C14−41.6 (7)C25—N4—C20—C21−166.1 (11)
O2—Cu2—O5—C15173.3 (6)C23—N4—C20—C2120.1 (15)
N3—Cu2—O5—C152.3 (6)C18—C19—C20—N4−179.8 (9)
Cu1—Cu2—O5—C15166.6 (7)C18—C19—C20—C21−2.5 (15)
O2—Cu2—O5—Cu16.7 (2)N4—C20—C21—C22179.1 (10)
N3—Cu2—O5—Cu1−164.3 (3)C19—C20—C21—C221.8 (15)
O3—Cu1—O5—C1512.8 (6)C20—C21—C22—C17−2.3 (16)
O2—Cu1—O5—C15−172.8 (7)C18—C17—C22—C213.3 (15)
Cu2—Cu1—O5—C15−166.1 (8)C16—C17—C22—C21179.6 (9)
O3—Cu1—O5—Cu2178.8 (2)C20—N4—C23—C24−98.5 (11)
O2—Cu1—O5—Cu2−6.8 (2)C25—N4—C23—C2487.4 (12)
O2—Cu2—O6—C18−163.7 (7)C20—N4—C25—C26−93.3 (12)
N3—Cu2—O6—C188.0 (7)C23—N4—C25—C2680.6 (12)
Cu1—Cu2—O6—C18−161.9 (6)
Acknowledgements top

This work was supported by the Foundation of the Education Department of Gansu Province (No. 0604–01) and the `Qing Lan' Talent Engineering Funds of Lanzhou Jiaotong University (No. QL-03–01 A), which are gratefully acknowledged.

references
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