metal-organic compounds
Bis{μ-5-(diethylamino)-2-[(2-oxidoethoxy)iminomethyl]phenolato}dicopper(II) acetone solvate
aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: dongwk@mail.lzjtu.cn
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 μ-dialkoxo-bridged binuclear structure with both CuII centers exhibiting a square-planar coordination geometry.
Related literature
For related literature, see: Bu et al. (1990); Dong et al. (2007a,b); Sun et al. (2008); Zhang et al. (2007).
Experimental
Crystal data
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Data collection: SMART (Siemens, 1996); cell SAINT (Siemens, 1996); 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: SHELXTL.
Supporting information
10.1107/S1600536808024707/gk2162sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808024707/gk2162Isup2.hkl
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.
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
in the riding model approximation, with Uiso(H) = 1.2Ueq(C).Data collection: SMART (Siemens, 1996); cell
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).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. |
[Cu2(C13H18N2O3)2]·C3H6O | F(000) = 1432 |
Mr = 685.75 | Dx = 1.491 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2917 reflections |
a = 20.633 (3) Å | θ = 2.4–22.9° |
b = 11.6045 (14) Å | µ = 1.44 mm−1 |
c = 13.0738 (17) Å | T = 298 K |
β = 102.635 (2)° | Prismatic, dark-brown |
V = 3054.6 (7) Å3 | 0.53 × 0.49 × 0.47 mm |
Z = 4 |
Bruker SMART 1000 CCD diffractometer | 5363 independent reflections |
Radiation source: fine-focus sealed tube | 2967 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.092 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −23→24 |
Tmin = 0.515, Tmax = 0.550 | k = −13→9 |
14726 measured reflections | l = −15→15 |
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)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.229 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1245P)2] where P = (Fo2 + 2Fc2)/3 |
5363 reflections | (Δ/σ)max = 0.001 |
385 parameters | Δρmax = 0.88 e Å−3 |
0 restraints | Δρmin = −1.07 e Å−3 |
[Cu2(C13H18N2O3)2]·C3H6O | V = 3054.6 (7) Å3 |
Mr = 685.75 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 20.633 (3) Å | µ = 1.44 mm−1 |
b = 11.6045 (14) Å | T = 298 K |
c = 13.0738 (17) Å | 0.53 × 0.49 × 0.47 mm |
β = 102.635 (2)° |
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 = 0.550 | Rint = 0.092 |
14726 measured reflections |
R[F2 > 2σ(F2)] = 0.075 | 0 restraints |
wR(F2) = 0.229 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.88 e Å−3 |
5363 reflections | Δρmin = −1.07 e Å−3 |
385 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.50062 (4) | 0.85967 (8) | 0.08317 (7) | 0.0325 (3) | |
Cu2 | 0.40492 (4) | 0.91965 (8) | 0.21830 (7) | 0.0350 (3) | |
N1 | 0.4892 (3) | 0.7990 (5) | −0.0554 (5) | 0.0362 (15) | |
N2 | 0.8064 (3) | 0.8744 (7) | 0.0240 (6) | 0.061 (2) | |
N3 | 0.4087 (3) | 1.0305 (6) | 0.3279 (5) | 0.0419 (16) | |
N4 | 0.0932 (4) | 0.9250 (8) | 0.2481 (7) | 0.075 (3) | |
O1 | 0.4275 (2) | 0.7535 (4) | −0.1126 (4) | 0.0392 (13) | |
O2 | 0.4116 (2) | 0.8328 (5) | 0.0968 (4) | 0.0412 (13) | |
O3 | 0.5922 (2) | 0.8847 (4) | 0.0975 (4) | 0.0398 (13) | |
O4 | 0.4662 (2) | 1.0969 (4) | 0.3692 (4) | 0.0447 (14) | |
O5 | 0.4970 (2) | 0.9318 (4) | 0.2158 (4) | 0.0395 (13) | |
O6 | 0.3153 (2) | 0.8842 (5) | 0.2103 (4) | 0.0456 (14) | |
O7 | 0.1481 (6) | 0.5560 (10) | 0.0993 (9) | 0.154 (4) | |
C1 | 0.3732 (3) | 0.8175 (7) | −0.0905 (6) | 0.0398 (19) | |
H1A | 0.3337 | 0.7991 | −0.1433 | 0.048* | |
H1B | 0.3822 | 0.8990 | −0.0968 | 0.048* | |
C2 | 0.3591 (3) | 0.7965 (7) | 0.0148 (6) | 0.042 (2) | |
H2A | 0.3189 | 0.8373 | 0.0199 | 0.051* | |
H2B | 0.3513 | 0.7149 | 0.0226 | 0.051* | |
C3 | 0.5347 (3) | 0.7810 (6) | −0.1079 (6) | 0.0386 (18) | |
H3 | 0.5222 | 0.7487 | −0.1744 | 0.046* | |
C4 | 0.6025 (3) | 0.8082 (7) | −0.0690 (6) | 0.0389 (18) | |
C5 | 0.6286 (4) | 0.8589 (7) | 0.0283 (6) | 0.0413 (19) | |
C6 | 0.6954 (4) | 0.8808 (7) | 0.0556 (7) | 0.048 (2) | |
H6 | 0.7128 | 0.9147 | 0.1203 | 0.058* | |
C7 | 0.7386 (4) | 0.8539 (8) | −0.0103 (7) | 0.051 (2) | |
C8 | 0.7128 (4) | 0.8060 (7) | −0.1067 (7) | 0.050 (2) | |
H8 | 0.7405 | 0.7888 | −0.1520 | 0.060* | |
C9 | 0.6464 (3) | 0.7839 (7) | −0.1356 (6) | 0.044 (2) | |
H9 | 0.6293 | 0.7518 | −0.2012 | 0.053* | |
C10 | 0.8505 (4) | 0.8597 (8) | −0.0509 (8) | 0.064 (3) | |
H10A | 0.8255 | 0.8780 | −0.1209 | 0.077* | |
H10B | 0.8868 | 0.9143 | −0.0334 | 0.077* | |
C11 | 0.8781 (5) | 0.7429 (9) | −0.0516 (8) | 0.080 (3) | |
H11A | 0.9047 | 0.7255 | 0.0165 | 0.120* | |
H11B | 0.9051 | 0.7389 | −0.1026 | 0.120* | |
H11C | 0.8425 | 0.6882 | −0.0690 | 0.120* | |
C12 | 0.8390 (5) | 0.9014 (9) | 0.1339 (8) | 0.072 (3) | |
H12A | 0.8152 | 0.8672 | 0.1827 | 0.087* | |
H12B | 0.8847 | 0.8750 | 0.1506 | 0.087* | |
C13 | 0.8354 (6) | 1.0267 (10) | 0.1358 (10) | 0.097 (4) | |
H13A | 0.8504 | 1.0576 | 0.0769 | 0.146* | |
H13B | 0.8631 | 1.0550 | 0.1996 | 0.146* | |
H13C | 0.7903 | 1.0500 | 0.1321 | 0.146* | |
C14 | 0.5245 (3) | 1.0263 (7) | 0.3815 (6) | 0.0422 (19) | |
H14A | 0.5166 | 0.9544 | 0.4147 | 0.051* | |
H14B | 0.5611 | 1.0652 | 0.4280 | 0.051* | |
C15 | 0.5443 (3) | 0.9998 (7) | 0.2812 (6) | 0.0397 (19) | |
H15A | 0.5498 | 1.0713 | 0.2456 | 0.048* | |
H15B | 0.5866 | 0.9599 | 0.2960 | 0.048* | |
C16 | 0.3585 (4) | 1.0680 (7) | 0.3631 (7) | 0.049 (2) | |
H16 | 0.3665 | 1.1265 | 0.4128 | 0.058* | |
C17 | 0.2923 (4) | 1.0267 (7) | 0.3318 (7) | 0.048 (2) | |
C18 | 0.2740 (4) | 0.9378 (8) | 0.2589 (7) | 0.051 (2) | |
C19 | 0.2075 (4) | 0.9048 (8) | 0.2342 (7) | 0.059 (3) | |
H19 | 0.1954 | 0.8429 | 0.1889 | 0.071* | |
C20 | 0.1578 (4) | 0.9599 (9) | 0.2739 (8) | 0.065 (3) | |
C21 | 0.1795 (5) | 1.0508 (8) | 0.3459 (8) | 0.066 (3) | |
H21 | 0.1487 | 1.0888 | 0.3761 | 0.079* | |
C22 | 0.2412 (4) | 1.0817 (8) | 0.3705 (7) | 0.057 (2) | |
H22 | 0.2527 | 1.1436 | 0.4161 | 0.069* | |
C23 | 0.0379 (5) | 1.0076 (11) | 0.2675 (10) | 0.087 (3) | |
H23A | 0.0533 | 1.0868 | 0.2728 | 0.104* | |
H23B | −0.0013 | 1.0020 | 0.2112 | 0.104* | |
C24 | 0.0237 (6) | 0.9686 (12) | 0.3669 (10) | 0.110 (4) | |
H24A | 0.0075 | 0.8908 | 0.3595 | 0.165* | |
H24B | −0.0093 | 1.0177 | 0.3856 | 0.165* | |
H24C | 0.0636 | 0.9718 | 0.4208 | 0.165* | |
C25 | 0.0727 (5) | 0.8171 (10) | 0.1932 (10) | 0.083 (3) | |
H25A | 0.1089 | 0.7620 | 0.2083 | 0.100* | |
H25B | 0.0352 | 0.7848 | 0.2170 | 0.100* | |
C26 | 0.0544 (6) | 0.8385 (12) | 0.0819 (10) | 0.109 (4) | |
H26A | 0.0138 | 0.8818 | 0.0659 | 0.164* | |
H26B | 0.0482 | 0.7664 | 0.0450 | 0.164* | |
H26C | 0.0890 | 0.8815 | 0.0607 | 0.164* | |
C27 | 0.2690 (8) | 0.5540 (14) | 0.1403 (14) | 0.151 (6) | |
H27A | 0.2945 | 0.6170 | 0.1761 | 0.226* | |
H27B | 0.2914 | 0.5225 | 0.0894 | 0.226* | |
H27C | 0.2645 | 0.4954 | 0.1901 | 0.226* | |
C28 | 0.2039 (10) | 0.5947 (16) | 0.0880 (15) | 0.139 (6) | |
C29 | 0.1968 (7) | 0.6857 (14) | 0.0057 (12) | 0.135 (5) | |
H29A | 0.1514 | 0.6892 | −0.0323 | 0.202* | |
H29B | 0.2249 | 0.6678 | −0.0417 | 0.202* | |
H29C | 0.2095 | 0.7589 | 0.0382 | 0.202* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0317 (5) | 0.0379 (6) | 0.0287 (5) | −0.0031 (4) | 0.0086 (4) | −0.0046 (4) |
Cu2 | 0.0319 (5) | 0.0410 (6) | 0.0332 (6) | −0.0024 (4) | 0.0093 (4) | −0.0071 (4) |
N1 | 0.030 (3) | 0.043 (4) | 0.036 (4) | −0.004 (3) | 0.010 (3) | −0.005 (3) |
N2 | 0.047 (4) | 0.071 (5) | 0.067 (6) | 0.000 (4) | 0.018 (4) | −0.004 (4) |
N3 | 0.036 (3) | 0.045 (4) | 0.047 (4) | −0.005 (3) | 0.014 (3) | −0.010 (3) |
N4 | 0.057 (5) | 0.081 (6) | 0.090 (7) | −0.005 (5) | 0.025 (5) | −0.023 (5) |
O1 | 0.034 (3) | 0.046 (3) | 0.038 (3) | −0.003 (2) | 0.009 (2) | −0.014 (3) |
O2 | 0.034 (3) | 0.052 (3) | 0.039 (3) | −0.006 (2) | 0.012 (2) | −0.011 (3) |
O3 | 0.034 (3) | 0.047 (3) | 0.041 (3) | −0.007 (2) | 0.013 (2) | −0.010 (3) |
O4 | 0.042 (3) | 0.042 (3) | 0.050 (4) | −0.008 (3) | 0.011 (3) | −0.011 (3) |
O5 | 0.035 (3) | 0.048 (3) | 0.037 (3) | −0.008 (2) | 0.013 (2) | −0.011 (3) |
O6 | 0.038 (3) | 0.051 (3) | 0.050 (4) | −0.004 (3) | 0.015 (3) | −0.017 (3) |
O7 | 0.137 (9) | 0.164 (11) | 0.162 (11) | −0.028 (8) | 0.036 (8) | −0.006 (8) |
C1 | 0.033 (4) | 0.046 (5) | 0.038 (5) | −0.004 (4) | 0.005 (3) | −0.007 (4) |
C2 | 0.035 (4) | 0.051 (5) | 0.041 (5) | −0.004 (4) | 0.009 (3) | −0.011 (4) |
C3 | 0.036 (4) | 0.042 (5) | 0.038 (5) | −0.003 (4) | 0.010 (3) | −0.003 (4) |
C4 | 0.036 (4) | 0.043 (5) | 0.041 (5) | −0.001 (4) | 0.014 (3) | −0.004 (4) |
C5 | 0.036 (4) | 0.045 (5) | 0.046 (5) | −0.001 (4) | 0.015 (4) | −0.005 (4) |
C6 | 0.039 (5) | 0.055 (5) | 0.052 (5) | −0.005 (4) | 0.015 (4) | −0.004 (4) |
C7 | 0.041 (5) | 0.057 (6) | 0.059 (6) | −0.003 (4) | 0.017 (4) | −0.004 (5) |
C8 | 0.042 (5) | 0.058 (6) | 0.055 (6) | 0.000 (4) | 0.019 (4) | −0.003 (5) |
C9 | 0.041 (4) | 0.048 (5) | 0.045 (5) | 0.001 (4) | 0.014 (4) | −0.003 (4) |
C10 | 0.049 (5) | 0.074 (7) | 0.072 (7) | −0.001 (5) | 0.020 (5) | −0.002 (6) |
C11 | 0.066 (6) | 0.085 (8) | 0.092 (8) | 0.011 (6) | 0.026 (6) | 0.006 (7) |
C12 | 0.053 (6) | 0.087 (8) | 0.078 (8) | −0.004 (6) | 0.017 (5) | −0.007 (6) |
C13 | 0.090 (8) | 0.088 (9) | 0.111 (11) | −0.004 (7) | 0.017 (7) | −0.006 (8) |
C14 | 0.038 (4) | 0.044 (5) | 0.043 (5) | −0.008 (4) | 0.006 (4) | −0.008 (4) |
C15 | 0.034 (4) | 0.044 (5) | 0.040 (5) | −0.010 (4) | 0.008 (3) | −0.009 (4) |
C16 | 0.045 (5) | 0.050 (5) | 0.053 (6) | −0.002 (4) | 0.017 (4) | −0.014 (4) |
C17 | 0.043 (5) | 0.052 (5) | 0.054 (6) | −0.005 (4) | 0.022 (4) | −0.016 (5) |
C18 | 0.044 (5) | 0.058 (6) | 0.058 (6) | −0.003 (4) | 0.023 (4) | −0.014 (5) |
C19 | 0.049 (5) | 0.064 (6) | 0.069 (7) | −0.005 (5) | 0.024 (5) | −0.017 (5) |
C20 | 0.053 (6) | 0.071 (7) | 0.076 (7) | −0.006 (5) | 0.023 (5) | −0.018 (6) |
C21 | 0.055 (6) | 0.071 (7) | 0.077 (7) | −0.003 (5) | 0.027 (5) | −0.020 (6) |
C22 | 0.050 (5) | 0.060 (6) | 0.065 (6) | −0.004 (5) | 0.023 (5) | −0.019 (5) |
C23 | 0.069 (7) | 0.096 (9) | 0.098 (10) | −0.007 (6) | 0.025 (6) | −0.018 (7) |
C24 | 0.097 (9) | 0.115 (11) | 0.116 (12) | −0.014 (8) | 0.019 (8) | −0.015 (9) |
C25 | 0.063 (7) | 0.092 (9) | 0.100 (10) | −0.008 (6) | 0.027 (6) | −0.021 (8) |
C26 | 0.097 (9) | 0.118 (11) | 0.108 (12) | −0.006 (8) | 0.013 (8) | −0.005 (9) |
C27 | 0.123 (13) | 0.170 (18) | 0.157 (17) | −0.019 (12) | 0.025 (12) | 0.007 (13) |
C28 | 0.128 (14) | 0.151 (16) | 0.145 (16) | −0.031 (13) | 0.047 (13) | 0.010 (12) |
C29 | 0.125 (12) | 0.144 (14) | 0.135 (14) | −0.020 (11) | 0.028 (10) | −0.008 (12) |
Cu1—O3 | 1.880 (5) | C11—H11A | 0.9600 |
Cu1—O2 | 1.909 (5) | C11—H11B | 0.9600 |
Cu1—N1 | 1.910 (6) | C11—H11C | 0.9600 |
Cu1—O5 | 1.942 (5) | C12—C13 | 1.456 (14) |
Cu1—Cu2 | 3.0051 (12) | C12—H12A | 0.9700 |
Cu2—O6 | 1.874 (5) | C12—H12B | 0.9700 |
Cu2—O2 | 1.911 (5) | C13—H13A | 0.9600 |
Cu2—O5 | 1.912 (5) | C13—H13B | 0.9600 |
Cu2—N3 | 1.914 (6) | C13—H13C | 0.9600 |
N1—C3 | 1.295 (8) | C14—C15 | 1.488 (10) |
N1—O1 | 1.428 (7) | C14—H14A | 0.9700 |
N2—C7 | 1.394 (10) | C14—H14B | 0.9700 |
N2—C12 | 1.480 (12) | C15—H15A | 0.9700 |
N2—C10 | 1.485 (11) | C15—H15B | 0.9700 |
N3—C16 | 1.297 (9) | C16—C17 | 1.421 (11) |
N3—O4 | 1.419 (7) | C16—H16 | 0.9300 |
N4—C20 | 1.363 (11) | C17—C18 | 1.400 (11) |
N4—C25 | 1.459 (13) | C17—C22 | 1.416 (10) |
N4—C23 | 1.552 (12) | C18—C19 | 1.392 (11) |
O1—C1 | 1.425 (8) | C19—C20 | 1.401 (11) |
O2—C2 | 1.412 (8) | C19—H19 | 0.9300 |
O3—C5 | 1.330 (8) | C20—C21 | 1.419 (13) |
O4—C14 | 1.435 (8) | C21—C22 | 1.295 (11) |
O5—C15 | 1.393 (8) | C21—H21 | 0.9300 |
O6—C18 | 1.324 (8) | C22—H22 | 0.9300 |
O7—C28 | 1.275 (16) | C23—C24 | 1.465 (14) |
C1—C2 | 1.488 (10) | C23—H23A | 0.9700 |
C1—H1A | 0.9700 | C23—H23B | 0.9700 |
C1—H1B | 0.9700 | C24—H24A | 0.9600 |
C2—H2A | 0.9700 | C24—H24B | 0.9600 |
C2—H2B | 0.9700 | C24—H24C | 0.9600 |
C3—C4 | 1.417 (10) | C25—C26 | 1.442 (15) |
C3—H3 | 0.9300 | C25—H25A | 0.9700 |
C4—C5 | 1.398 (11) | C25—H25B | 0.9700 |
C4—C9 | 1.415 (10) | C26—H26A | 0.9600 |
C5—C6 | 1.371 (10) | C26—H26B | 0.9600 |
C6—C7 | 1.403 (11) | C26—H26C | 0.9600 |
C6—H6 | 0.9300 | C27—C28 | 1.45 (2) |
C7—C8 | 1.374 (12) | C27—H27A | 0.9600 |
C8—C9 | 1.365 (10) | C27—H27B | 0.9600 |
C8—H8 | 0.9300 | C27—H27C | 0.9600 |
C9—H9 | 0.9300 | C28—C29 | 1.49 (2) |
C10—C11 | 1.470 (13) | C29—H29A | 0.9600 |
C10—H10A | 0.9700 | C29—H29B | 0.9600 |
C10—H10B | 0.9700 | C29—H29C | 0.9600 |
O3—Cu1—O2 | 169.2 (2) | H11B—C11—H11C | 109.5 |
O3—Cu1—N1 | 93.7 (2) | C13—C12—N2 | 102.3 (9) |
O2—Cu1—N1 | 96.1 (2) | C13—C12—H12A | 111.3 |
O3—Cu1—O5 | 94.5 (2) | N2—C12—H12A | 111.3 |
O2—Cu1—O5 | 76.2 (2) | C13—C12—H12B | 111.3 |
N1—Cu1—O5 | 170.1 (2) | N2—C12—H12B | 111.3 |
O3—Cu1—Cu2 | 132.92 (15) | H12A—C12—H12B | 109.2 |
O2—Cu1—Cu2 | 38.15 (15) | C12—C13—H13A | 109.5 |
N1—Cu1—Cu2 | 133.02 (17) | C12—C13—H13B | 109.5 |
O5—Cu1—Cu2 | 38.40 (13) | H13A—C13—H13B | 109.5 |
O6—Cu2—O2 | 95.0 (2) | C12—C13—H13C | 109.5 |
O6—Cu2—O5 | 170.6 (2) | H13A—C13—H13C | 109.5 |
O2—Cu2—O5 | 76.8 (2) | H13B—C13—H13C | 109.5 |
O6—Cu2—N3 | 93.9 (2) | O4—C14—C15 | 113.7 (6) |
O2—Cu2—N3 | 167.9 (2) | O4—C14—H14A | 108.8 |
O5—Cu2—N3 | 94.9 (2) | C15—C14—H14A | 108.8 |
O6—Cu2—Cu1 | 133.10 (16) | O4—C14—H14B | 108.8 |
O2—Cu2—Cu1 | 38.11 (14) | C15—C14—H14B | 108.8 |
O5—Cu2—Cu1 | 39.11 (14) | H14A—C14—H14B | 107.7 |
N3—Cu2—Cu1 | 132.15 (18) | O5—C15—C14 | 111.6 (6) |
C3—N1—O1 | 109.2 (6) | O5—C15—H15A | 109.3 |
C3—N1—Cu1 | 127.5 (5) | C14—C15—H15A | 109.3 |
O1—N1—Cu1 | 123.0 (4) | O5—C15—H15B | 109.3 |
C7—N2—C12 | 124.0 (7) | C14—C15—H15B | 109.3 |
C7—N2—C10 | 119.0 (8) | H15A—C15—H15B | 108.0 |
C12—N2—C10 | 116.8 (7) | N3—C16—C17 | 125.3 (8) |
C16—N3—O4 | 110.4 (6) | N3—C16—H16 | 117.4 |
C16—N3—Cu2 | 125.9 (6) | C17—C16—H16 | 117.4 |
O4—N3—Cu2 | 122.9 (4) | C18—C17—C22 | 117.7 (7) |
C20—N4—C25 | 122.6 (8) | C18—C17—C16 | 122.9 (7) |
C20—N4—C23 | 119.3 (8) | C22—C17—C16 | 119.3 (8) |
C25—N4—C23 | 117.8 (8) | O6—C18—C19 | 117.7 (8) |
C1—O1—N1 | 110.6 (5) | O6—C18—C17 | 124.5 (7) |
C2—O2—Cu1 | 124.9 (4) | C19—C18—C17 | 117.8 (7) |
C2—O2—Cu2 | 127.3 (4) | C18—C19—C20 | 123.6 (9) |
Cu1—O2—Cu2 | 103.7 (2) | C18—C19—H19 | 118.2 |
C5—O3—Cu1 | 127.0 (5) | C20—C19—H19 | 118.2 |
N3—O4—C14 | 110.0 (5) | N4—C20—C19 | 121.9 (9) |
C15—O5—Cu2 | 126.6 (4) | N4—C20—C21 | 122.3 (8) |
C15—O5—Cu1 | 129.3 (4) | C19—C20—C21 | 115.8 (8) |
Cu2—O5—Cu1 | 102.5 (2) | C22—C21—C20 | 121.4 (9) |
C18—O6—Cu2 | 126.9 (5) | C22—C21—H21 | 119.3 |
O1—C1—C2 | 115.1 (6) | C20—C21—H21 | 119.3 |
O1—C1—H1A | 108.5 | C21—C22—C17 | 123.7 (9) |
C2—C1—H1A | 108.5 | C21—C22—H22 | 118.2 |
O1—C1—H1B | 108.5 | C17—C22—H22 | 118.2 |
C2—C1—H1B | 108.5 | C24—C23—N4 | 104.5 (10) |
H1A—C1—H1B | 107.5 | C24—C23—H23A | 110.8 |
O2—C2—C1 | 112.4 (6) | N4—C23—H23A | 110.8 |
O2—C2—H2A | 109.1 | C24—C23—H23B | 110.8 |
C1—C2—H2A | 109.1 | N4—C23—H23B | 110.8 |
O2—C2—H2B | 109.1 | H23A—C23—H23B | 108.9 |
C1—C2—H2B | 109.1 | C23—C24—H24A | 109.5 |
H2A—C2—H2B | 107.9 | C23—C24—H24B | 109.5 |
N1—C3—C4 | 123.2 (7) | H24A—C24—H24B | 109.5 |
N1—C3—H3 | 118.4 | C23—C24—H24C | 109.5 |
C4—C3—H3 | 118.4 | H24A—C24—H24C | 109.5 |
C5—C4—C9 | 118.3 (7) | H24B—C24—H24C | 109.5 |
C5—C4—C3 | 125.0 (7) | C26—C25—N4 | 109.4 (11) |
C9—C4—C3 | 116.7 (7) | C26—C25—H25A | 109.8 |
O3—C5—C6 | 117.8 (7) | N4—C25—H25A | 109.8 |
O3—C5—C4 | 123.5 (7) | C26—C25—H25B | 109.8 |
C6—C5—C4 | 118.7 (7) | N4—C25—H25B | 109.8 |
C5—C6—C7 | 122.4 (8) | H25A—C25—H25B | 108.2 |
C5—C6—H6 | 118.8 | C25—C26—H26A | 109.5 |
C7—C6—H6 | 118.8 | C25—C26—H26B | 109.5 |
C8—C7—N2 | 121.6 (8) | H26A—C26—H26B | 109.5 |
C8—C7—C6 | 118.9 (8) | C25—C26—H26C | 109.5 |
N2—C7—C6 | 119.5 (8) | H26A—C26—H26C | 109.5 |
C9—C8—C7 | 119.6 (8) | H26B—C26—H26C | 109.5 |
C9—C8—H8 | 120.2 | C28—C27—H27A | 109.5 |
C7—C8—H8 | 120.2 | C28—C27—H27B | 109.5 |
C8—C9—C4 | 122.1 (8) | H27A—C27—H27B | 109.5 |
C8—C9—H9 | 119.0 | C28—C27—H27C | 109.5 |
C4—C9—H9 | 119.0 | H27A—C27—H27C | 109.5 |
C11—C10—N2 | 113.8 (8) | H27B—C27—H27C | 109.5 |
C11—C10—H10A | 108.8 | O7—C28—C27 | 126.8 (18) |
N2—C10—H10A | 108.8 | O7—C28—C29 | 112.6 (17) |
C11—C10—H10B | 108.8 | C27—C28—C29 | 120.5 (16) |
N2—C10—H10B | 108.8 | C28—C29—H29A | 109.5 |
H10A—C10—H10B | 107.7 | C28—C29—H29B | 109.5 |
C10—C11—H11A | 109.5 | H29A—C29—H29B | 109.5 |
C10—C11—H11B | 109.5 | C28—C29—H29C | 109.5 |
H11A—C11—H11B | 109.5 | H29A—C29—H29C | 109.5 |
C10—C11—H11C | 109.5 | H29B—C29—H29C | 109.5 |
H11A—C11—H11C | 109.5 | ||
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—O6 | 14.9 (4) | Cu2—O2—C2—C1 | 134.5 (6) |
O5—Cu1—Cu2—O6 | −172.3 (3) | O1—C1—C2—O2 | 64.6 (9) |
O3—Cu1—Cu2—O2 | −170.9 (3) | O1—N1—C3—C4 | −175.2 (7) |
N1—Cu1—Cu2—O2 | 17.8 (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—O5 | 169.3 (4) | Cu1—O3—C5—C6 | −177.8 (5) |
N1—Cu1—Cu2—O5 | −172.8 (4) | Cu1—O3—C5—C4 | 0.5 (11) |
O3—Cu1—Cu2—N3 | 19.7 (4) | C9—C4—C5—O3 | −179.4 (7) |
O2—Cu1—Cu2—N3 | −169.3 (4) | C3—C4—C5—O3 | 2.0 (13) |
N1—Cu1—Cu2—N3 | −151.5 (4) | C9—C4—C5—C6 | −1.2 (12) |
O5—Cu1—Cu2—N3 | 21.3 (4) | C3—C4—C5—C6 | −179.8 (8) |
O3—Cu1—N1—C3 | 3.2 (7) | O3—C5—C6—C7 | 178.2 (7) |
O2—Cu1—N1—C3 | −172.3 (7) | C4—C5—C6—C7 | −0.2 (13) |
Cu2—Cu1—N1—C3 | 176.8 (5) | C12—N2—C7—C8 | −166.2 (9) |
O3—Cu1—N1—O1 | 175.6 (5) | C10—N2—C7—C8 | 8.8 (13) |
O2—Cu1—N1—O1 | 0.1 (5) | C12—N2—C7—C6 | 12.7 (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—C8 | 1.4 (14) |
O2—Cu2—N3—C16 | 129.1 (11) | C5—C6—C7—N2 | −177.5 (8) |
O5—Cu2—N3—C16 | 175.3 (7) | N2—C7—C8—C9 | 177.8 (8) |
Cu1—Cu2—N3—C16 | 162.0 (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—C8 | 1.5 (12) |
O5—Cu2—N3—O4 | 6.4 (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—C11 | 84.7 (11) |
Cu1—N1—O1—C1 | 36.0 (7) | C7—N2—C12—C13 | −90.3 (10) |
O3—Cu1—O2—C2 | −163.5 (10) | C10—N2—C12—C13 | 94.6 (10) |
N1—Cu1—O2—C2 | −8.5 (6) | N3—O4—C14—C15 | 75.3 (7) |
O5—Cu1—O2—C2 | 165.3 (6) | Cu2—O5—C15—C14 | 23.7 (9) |
Cu2—Cu1—O2—C2 | 158.5 (7) | Cu1—O5—C15—C14 | −173.3 (5) |
O3—Cu1—O2—Cu2 | 38.0 (13) | O4—C14—C15—O5 | −65.7 (9) |
N1—Cu1—O2—Cu2 | −167.0 (3) | O4—N3—C16—C17 | 175.1 (8) |
O5—Cu1—O2—Cu2 | 6.8 (2) | Cu2—N3—C16—C17 | 5.1 (13) |
O6—Cu2—O2—C2 | 20.1 (6) | N3—C16—C17—C18 | 1.0 (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—C19 | 173.8 (6) |
Cu1—Cu2—O2—C2 | −157.8 (7) | Cu2—O6—C18—C17 | −5.0 (13) |
O6—Cu2—O2—Cu1 | 177.9 (3) | C22—C17—C18—O6 | 175.0 (8) |
O5—Cu2—O2—Cu1 | −6.9 (2) | C16—C17—C18—O6 | −1.2 (15) |
N3—Cu2—O2—Cu1 | 40.8 (13) | C22—C17—C18—C19 | −3.8 (13) |
O2—Cu1—O3—C5 | 152.7 (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—C20 | 3.6 (15) |
Cu2—Cu1—O3—C5 | −176.0 (5) | C25—N4—C20—C19 | 11.0 (16) |
C16—N3—O4—C14 | 148.0 (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—C15 | 173.3 (6) | C23—N4—C20—C21 | 20.1 (15) |
N3—Cu2—O5—C15 | 2.3 (6) | C18—C19—C20—N4 | −179.8 (9) |
Cu1—Cu2—O5—C15 | 166.6 (7) | C18—C19—C20—C21 | −2.5 (15) |
O2—Cu2—O5—Cu1 | 6.7 (2) | N4—C20—C21—C22 | 179.1 (10) |
N3—Cu2—O5—Cu1 | −164.3 (3) | C19—C20—C21—C22 | 1.8 (15) |
O3—Cu1—O5—C15 | 12.8 (6) | C20—C21—C22—C17 | −2.3 (16) |
O2—Cu1—O5—C15 | −172.8 (7) | C18—C17—C22—C21 | 3.3 (15) |
Cu2—Cu1—O5—C15 | −166.1 (8) | C16—C17—C22—C21 | 179.6 (9) |
O3—Cu1—O5—Cu2 | 178.8 (2) | C20—N4—C23—C24 | −98.5 (11) |
O2—Cu1—O5—Cu2 | −6.8 (2) | C25—N4—C23—C24 | 87.4 (12) |
O2—Cu2—O6—C18 | −163.7 (7) | C20—N4—C25—C26 | −93.3 (12) |
N3—Cu2—O6—C18 | 8.0 (7) | C23—N4—C25—C26 | 80.6 (12) |
Cu1—Cu2—O6—C18 | −161.9 (6) |
Experimental details
Crystal data | |
Chemical formula | [Cu2(C13H18N2O3)2]·C3H6O |
Mr | 685.75 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 20.633 (3), 11.6045 (14), 13.0738 (17) |
β (°) | 102.635 (2) |
V (Å3) | 3054.6 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.44 |
Crystal size (mm) | 0.53 × 0.49 × 0.47 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.515, 0.550 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14726, 5363, 2967 |
Rint | 0.092 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.075, 0.229, 1.00 |
No. of reflections | 5363 |
No. of parameters | 385 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.88, −1.07 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
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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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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)°.