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Acta Cryst. (2007). E63, m1887-m1888    [ doi:10.1107/S1600536807028255 ]

(Dihydroxyglyoxime-[kappa]2N,N')bis(1,10-phenanthroline-[kappa]2N,N')copper(II) dinitrate dihydrate

T. Liu, Z.-W. Wang, Y.-X. Wang and Z.-P. Xie

Abstract top

In the molecule of the title compound, [Cu(C12H8N2)2(C2H4N2O4)](NO3)2·2H2O, the Cu atom has a distorted octahedral coordination formed by six N atoms from one dihydroxyglyoxime and two 1,10-phenanthroline ligands. In the crystal structure, molecules are linked into a three-dimensional framework by O-H...O and C-H...O hydrogen bonds and by [pi]-[pi] stacking interactions, with a centroid-centroid distance of 3.5692 (5) Å (symmetry code: 1 - x, 2 - y, 1 - z).

Comment top

In recent years, interest in the chemistry of metal-oxygen clusters has grown because of their applications in areas including catalysis, materials chemistry and biochemistry (Pope, 1983; Pope & Müller, 2001). π-π Stacking between aromatic rings is related to the electron-transfer process in some biological systems (Deisenhofer & Michel, 1989; Wall et al., 1999). Aromatic polycyclic compounds, such as phenanthroline, quinoline and benzimidazole, have commonly shown π-π stacking in metal complexes (Wu et al., 2003; Pan & Xu, 2004; Liu et al., 2004; Li et al., 2005). As a bidentate flexible ligand, dihydroxyglyoxime is also a good ligand with excellent coordination capabilities for generating mono-, bi- or trinuclear complexes, which are commonly used as precursors for the formation of supramolecular architectures (Chaudhuri et al., 1991; Cervera et al., 1997). We report here the crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The six N atoms of one dihydroxyglyoxime and two 1,10-phenanthroline (phen) ligands are coordinated to the Cu atom, in a distorted octahedral arrangement (Table 1). The dihydroxyglyoxime and two phen ligands are each planar, and the phen ligands are nearly perpendicular to each other, with a dihedral angle of 87.21 (5)°.

In the crystal structure, there is a three-dimensional framework (Fig. 2) formed by O—H···O and C—H···O hydrogen bonds (Table 2). There are π-π stacking interactions between adjacent phen ligands with a centroid-centroid distance of 3.543 (2) Å (symmetry code: 1 - x, 2 - y, 1 - z). These π-π stacking interactions and hydrogen bonds lead to a supramolecular network structure (Fig. 2).

Related literature top

For general background, see: Pope (1983); Pope & Müller (2001); Deisenhofer & Michel (1989); Wall et al. (1999); Allen et al. (1987). For related literature, see: Wu et al. (2003); Pan & Xu (2004); Liu et al. (2004); Li et al. (2005); Chaudhuri et al. (1991); Cervera et al. (1997).

Experimental top

Copper(II) dinitrate hexahydrate (296 mg, 1 mmol), phen (396 mg, 2 mmol) and dihydroxyglyoxime (120 mg, 1 mmol) were dissolved in ethanol (20 ml). The mixture was heated for 5 h under reflux with stirring. It was then filtered to give a clear solution, into which diethyl ether vapour was allowed to condense in a closed vessel. After being allowed to stand for a few days at room temperature, some blue single crystals suitable for X-ray diffraction analysis precipitated.

Refinement top

H atoms of the water molecules were located in a difference synthesis and refined isotropically [O—H = 0.84 (3)–0.86 (9) Å, Uiso(H) = 0.450 (8)–0.59 (5) Å2]. The remaining H atoms were positioned geometrically, with O—H = 0.82 Å (for OH) and C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.2 for aromatic H atoms and x = 1.5 for OH H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The structure of the cationic complex of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Solvent molecules and nitrate anions have been omitted for clarity.
[Figure 2] Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.
(Dihydroxyglyoxime-κ2N,N')bis(1,10-phenanthroline-κ2N,N')copper(II) dinitrate dihydrate top
Crystal data top
[Cu(C12H8N2)2(C2H4N2O4)](NO3)2·2H2OF(000) = 1444
Mr = 704.07Dx = 1.534 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5663 reflections
a = 13.9108 (7) Åθ = 2.2–24.9°
b = 12.011 (3) ŵ = 0.79 mm−1
c = 18.338 (4) ÅT = 273 K
β = 95.897 (5)°Prism, blue
V = 3047.8 (10) Å30.30 × 0.23 × 0.18 mm
Z = 4
Data collection top
Bruker APEXII area-detector
diffractometer		6028 independent reflections
Radiation source: fine-focus sealed tube3118 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −17→17
Tmin = 0.798, Tmax = 0.871k = −15→15
19706 measured reflectionsl = −22→22
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0966P)2]
where P = (Fo2 + 2Fc2)/3
6028 reflections(Δ/σ)max = 0.005
444 parametersΔρmax = 0.79 e Å−3
12 restraintsΔρmin = −0.61 e Å−3
Crystal data top
[Cu(C12H8N2)2(C2H4N2O4)](NO3)2·2H2OV = 3047.8 (10) Å3
Mr = 704.07Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.9108 (7) ŵ = 0.79 mm−1
b = 12.011 (3) ÅT = 273 K
c = 18.338 (4) Å0.30 × 0.23 × 0.18 mm
β = 95.897 (5)°
Data collection top
Bruker APEXII area-detector
diffractometer		6028 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3118 reflections with I > 2σ(I)
Tmin = 0.798, Tmax = 0.871Rint = 0.041
19706 measured reflectionsθmax = 26.4°
Refinement top
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.167Δρmax = 0.79 e Å−3
S = 1.00Δρmin = −0.61 e Å−3
6028 reflectionsAbsolute structure: ?
444 parametersFlack parameter: ?
12 restraintsRogers parameter: ?
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
Cu10.77579 (4)0.75553 (5)0.03828 (3)0.0432 (2)
O10.7961 (3)0.9961 (3)0.04774 (18)0.0483 (9)
H1A0.80000.99540.00340.072*
O20.8338 (3)0.6031 (3)0.1481 (2)0.0563 (10)
H2A0.87120.59210.18500.085*
O30.9324 (4)0.7551 (5)0.2458 (3)0.1201 (19)
H3A0.99080.75450.24310.180*
O40.9039 (5)0.9954 (5)0.1835 (4)0.133 (2)
H4A0.95200.97960.21110.199*
O50.7739 (3)0.1302 (3)0.9096 (3)0.0814 (13)
O60.8930 (3)0.0159 (3)0.9283 (2)0.0641 (11)
O70.8887 (4)0.1343 (4)0.8437 (3)0.116 (2)
O80.7394 (6)0.8785 (7)0.2880 (4)0.166 (3)
O90.6158 (7)0.8835 (7)0.3358 (5)0.184 (3)
O100.6387 (9)1.0077 (7)0.2627 (6)0.345 (11)
O110.5584 (13)0.4277 (14)0.1452 (12)0.497 (14)
O120.701 (2)0.340 (2)0.2000 (12)0.59 (2)
N10.6533 (3)0.7801 (3)0.0767 (2)0.0376 (9)
N20.7067 (3)0.8187 (3)−0.0534 (2)0.0355 (9)
N30.7384 (3)0.6056 (3)0.0042 (2)0.0396 (9)
N40.8936 (2)0.7245 (3)−0.0073 (2)0.0343 (9)
N50.8376 (3)0.7047 (3)0.1298 (2)0.0391 (9)
N60.8219 (2)0.8937 (3)0.0767 (2)0.0350 (9)
N70.8515 (3)0.0921 (4)0.8922 (3)0.0569 (12)
N80.6658 (6)0.9287 (9)0.2899 (5)0.130 (4)
C10.6305 (4)0.7620 (4)0.1432 (3)0.0491 (13)
H10.67780.73680.17890.059*
C20.5357 (4)0.7800 (5)0.1620 (3)0.0604 (15)
H20.52130.76580.20950.072*
C30.4666 (4)0.8173 (4)0.1120 (3)0.0557 (15)
H30.40440.82910.12480.067*
C40.4874 (3)0.8387 (4)0.0409 (3)0.0461 (13)
C50.4204 (4)0.8802 (4)−0.0169 (4)0.0583 (15)
H50.35660.8924−0.00810.070*
C60.4477 (4)0.9023 (4)−0.0846 (4)0.0615 (16)
H60.40250.9298−0.12110.074*
C70.5462 (4)0.8834 (4)−0.1004 (3)0.0497 (13)
C80.5808 (4)0.9063 (4)−0.1659 (3)0.0594 (15)
H80.53980.9356−0.20440.071*
C90.6761 (5)0.8862 (4)−0.1748 (3)0.0598 (15)
H90.70010.9030−0.21900.072*
C100.7367 (4)0.8403 (4)−0.1171 (3)0.0464 (13)
H100.80060.8247−0.12420.056*
C110.6124 (3)0.8403 (3)−0.0443 (3)0.0398 (12)
C120.5832 (3)0.8180 (3)0.0253 (3)0.0371 (11)
C130.6609 (4)0.5462 (4)0.0146 (3)0.0554 (14)
H130.61470.57610.04220.066*
C140.6468 (4)0.4405 (5)−0.0147 (4)0.0681 (18)
H140.59130.4008−0.00690.082*
C150.7131 (4)0.3945 (4)−0.0545 (3)0.0674 (17)
H150.70340.3235−0.07410.081*
C160.7968 (4)0.4544 (4)−0.0662 (3)0.0447 (12)
C170.8721 (4)0.4155 (4)−0.1062 (3)0.0511 (14)
H170.86550.3468−0.12960.061*
C180.9512 (4)0.4742 (4)−0.1111 (3)0.0533 (14)
H180.99970.4447−0.13660.064*
C190.9650 (3)0.5830 (4)−0.0780 (3)0.0415 (12)
C201.0481 (4)0.6512 (4)−0.0796 (3)0.0487 (13)
H201.10030.6273−0.10340.058*
C211.0500 (3)0.7503 (4)−0.0464 (3)0.0479 (12)
H211.10400.7957−0.04740.057*
C220.9725 (3)0.7865 (4)−0.0103 (3)0.0429 (12)
H220.97580.85600.01220.051*
C230.8906 (3)0.6243 (4)−0.0405 (2)0.0367 (11)
C240.8064 (3)0.5595 (4)−0.0348 (2)0.0367 (11)
C250.8804 (3)0.7815 (4)0.1715 (3)0.0401 (11)
C260.8672 (3)0.8918 (4)0.1413 (3)0.0430 (12)
H11A0.514 (4)0.400 (3)0.116 (3)0.500 (16)*
H12A0.673 (10)0.286 (4)0.220 (6)0.59 (5)*
H11B0.557 (2)0.4964 (15)0.1531 (19)0.450 (8)*
H12B0.729 (3)0.317 (3)0.1644 (18)0.587 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0397 (4)0.0421 (4)0.0469 (4)0.0020 (3)0.0012 (3)−0.0024 (3)
O10.060 (2)0.0367 (18)0.047 (2)0.0085 (15)0.0012 (18)−0.0016 (16)
O20.059 (2)0.050 (2)0.057 (3)0.0037 (17)−0.0072 (18)0.0168 (18)
O30.106 (4)0.149 (5)0.097 (4)0.000 (4)−0.027 (3)0.018 (3)
O40.148 (6)0.112 (4)0.133 (6)−0.017 (4)−0.010 (4)−0.042 (4)
O50.059 (3)0.079 (3)0.107 (4)0.012 (2)0.016 (3)0.008 (3)
O60.064 (2)0.051 (2)0.076 (3)0.0083 (19)0.004 (2)0.014 (2)
O70.117 (4)0.116 (4)0.124 (5)0.031 (3)0.054 (4)0.053 (4)
O80.149 (6)0.189 (8)0.158 (7)−0.025 (6)0.007 (6)−0.034 (5)
O90.222 (10)0.186 (8)0.142 (7)0.006 (7)0.009 (6)−0.017 (6)
O100.49 (2)0.122 (7)0.349 (15)−0.081 (8)−0.327 (14)0.109 (8)
O110.46 (3)0.62 (3)0.47 (3)0.05 (3)0.35 (3)0.10 (3)
O120.48 (3)0.94 (6)0.34 (3)−0.12 (3)0.01 (2)−0.40 (3)
N10.037 (2)0.034 (2)0.042 (3)0.0023 (16)0.0026 (18)−0.0003 (18)
N20.040 (2)0.030 (2)0.035 (3)0.0036 (16)−0.0011 (18)−0.0033 (18)
N30.035 (2)0.034 (2)0.049 (3)−0.0009 (17)0.0014 (19)−0.0016 (19)
N40.031 (2)0.031 (2)0.040 (2)0.0034 (15)−0.0023 (16)−0.0020 (17)
N50.035 (2)0.040 (2)0.042 (3)0.0049 (18)0.0047 (18)0.006 (2)
N60.034 (2)0.031 (2)0.040 (3)0.0020 (16)0.0013 (18)−0.0020 (18)
N70.051 (3)0.054 (3)0.067 (4)−0.007 (2)0.011 (3)0.009 (3)
N80.084 (6)0.195 (11)0.108 (7)−0.026 (6)0.003 (5)−0.081 (8)
C10.043 (3)0.058 (3)0.046 (3)0.008 (2)0.005 (2)0.006 (3)
C20.053 (3)0.070 (4)0.060 (4)0.001 (3)0.016 (3)−0.002 (3)
C30.037 (3)0.056 (3)0.077 (5)−0.002 (2)0.016 (3)−0.016 (3)
C40.037 (3)0.032 (3)0.068 (4)−0.002 (2)−0.002 (3)−0.009 (3)
C50.036 (3)0.050 (3)0.087 (5)0.004 (2)−0.003 (3)−0.006 (3)
C60.051 (3)0.045 (3)0.084 (5)0.010 (3)−0.020 (3)−0.007 (3)
C70.053 (3)0.038 (3)0.054 (4)0.001 (2)−0.014 (3)−0.006 (3)
C80.075 (4)0.048 (3)0.050 (4)0.011 (3)−0.016 (3)−0.001 (3)
C90.092 (5)0.045 (3)0.040 (4)−0.003 (3)−0.004 (3)−0.001 (3)
C100.060 (3)0.041 (3)0.038 (3)0.004 (2)0.003 (3)−0.005 (2)
C110.043 (3)0.027 (2)0.047 (3)0.002 (2)−0.009 (2)−0.001 (2)
C120.034 (3)0.030 (2)0.047 (3)0.0008 (19)0.000 (2)−0.005 (2)
C130.043 (3)0.045 (3)0.079 (4)−0.004 (2)0.008 (3)−0.005 (3)
C140.053 (4)0.045 (3)0.107 (5)−0.013 (3)0.007 (3)−0.011 (3)
C150.070 (4)0.035 (3)0.093 (5)−0.009 (3)−0.008 (4)−0.012 (3)
C160.052 (3)0.033 (3)0.046 (3)0.006 (2)−0.010 (2)−0.001 (2)
C170.072 (4)0.037 (3)0.042 (3)0.009 (3)−0.003 (3)−0.007 (2)
C180.075 (4)0.051 (3)0.033 (3)0.031 (3)0.001 (3)−0.006 (3)
C190.046 (3)0.047 (3)0.031 (3)0.013 (2)−0.002 (2)0.004 (2)
C200.043 (3)0.063 (4)0.041 (3)0.013 (3)0.008 (2)0.005 (3)
C210.037 (3)0.060 (3)0.047 (3)−0.003 (3)0.004 (2)0.003 (3)
C220.042 (3)0.039 (3)0.047 (3)0.003 (2)0.000 (2)−0.003 (2)
C230.038 (3)0.038 (3)0.033 (3)0.007 (2)−0.005 (2)0.002 (2)
C240.042 (3)0.032 (2)0.034 (3)0.005 (2)−0.004 (2)0.000 (2)
C250.039 (3)0.049 (3)0.032 (3)0.002 (2)0.001 (2)0.002 (2)
C260.042 (3)0.043 (3)0.043 (3)−0.002 (2)0.005 (2)−0.013 (2)
Geometric parameters (Å, º) top
Cu1—N11.933 (4)C3—C41.388 (7)
Cu1—N21.999 (4)C3—H30.9300
Cu1—N31.959 (4)C4—C121.414 (6)
Cu1—N41.950 (3)C4—C51.428 (7)
Cu1—N51.906 (4)C5—C61.361 (8)
Cu1—N61.889 (4)C5—H50.9300
O1—N61.372 (4)C6—C71.448 (7)
O1—H1A0.8200C6—H60.9300
O2—N51.269 (5)C7—C81.365 (7)
O2—H2A0.8200C7—C111.408 (7)
O3—C251.509 (6)C8—C91.374 (7)
O3—H3A0.8200C8—H80.9300
O4—C261.525 (6)C9—C101.397 (7)
O4—H4A0.8200C9—H90.9300
O5—N71.244 (5)C10—H100.9300
O6—N71.237 (5)C11—C121.403 (6)
O7—N71.188 (6)C13—C141.384 (7)
O8—N81.192 (9)C13—H130.9300
O9—N81.268 (9)C14—C151.353 (7)
O10—N81.119 (10)C14—H140.9300
O11—H11A0.84 (5)C15—C161.403 (7)
O11—H11B0.84 (3)C15—H150.9300
O12—H12A0.86 (9)C16—C241.389 (6)
O12—H12B0.84 (4)C16—C171.419 (7)
N1—C11.309 (6)C17—C181.317 (7)
N1—C121.363 (6)C17—H170.9300
N2—C101.305 (6)C18—C191.445 (7)
N2—C111.365 (5)C18—H180.9300
N3—C131.323 (6)C19—C231.391 (6)
N3—C241.360 (5)C19—C201.419 (7)
N4—C221.332 (6)C20—C211.336 (6)
N4—C231.348 (5)C20—H200.9300
N5—C251.302 (6)C21—C221.392 (6)
N6—C261.284 (6)C21—H210.9300
C1—C21.414 (7)C22—H220.9300
C1—H10.9300C23—C241.419 (6)
C2—C31.336 (8)C25—C261.440 (6)
C2—H20.9300
N1—Cu1—N283.30 (16)C7—C6—H6119.6
N1—Cu1—N392.39 (15)C8—C7—C11117.0 (5)
N1—Cu1—N4175.33 (15)C8—C7—C6124.8 (5)
N1—Cu1—N593.57 (16)C11—C7—C6118.2 (5)
N1—Cu1—N690.45 (15)C7—C8—C9120.0 (5)
N2—Cu1—N389.54 (15)C7—C8—H8120.0
N2—Cu1—N493.71 (15)C9—C8—H8120.0
N2—Cu1—N5175.49 (15)C8—C9—C10119.6 (5)
N2—Cu1—N695.51 (15)C8—C9—H9120.2
N3—Cu1—N483.97 (15)C10—C9—H9120.2
N3—Cu1—N593.86 (17)N2—C10—C9122.1 (5)
N3—Cu1—N6174.47 (16)N2—C10—H10118.9
N4—Cu1—N589.60 (15)C9—C10—H10118.9
N4—Cu1—N693.42 (15)N2—C11—C12116.5 (4)
N5—Cu1—N681.23 (17)N2—C11—C7123.0 (5)
N6—O1—H1A109.5C12—C11—C7120.5 (5)
N5—O2—H2A109.5N1—C12—C11116.1 (4)
C25—O3—H3A109.5N1—C12—C4122.7 (5)
C26—O4—H4A109.5C11—C12—C4121.1 (4)
H11A—O11—H11B118 (3)N3—C13—C14121.6 (5)
H12A—O12—H12B111 (7)N3—C13—H13119.2
C1—N1—C12118.4 (4)C14—C13—H13119.2
C1—N1—Cu1128.4 (3)C15—C14—C13120.4 (5)
C12—N1—Cu1113.1 (3)C15—C14—H14119.8
C10—N2—C11118.2 (4)C13—C14—H14119.8
C10—N2—Cu1131.1 (3)C14—C15—C16119.7 (5)
C11—N2—Cu1110.7 (3)C14—C15—H15120.1
C13—N3—C24118.5 (4)C16—C15—H15120.1
C13—N3—Cu1130.1 (3)C24—C16—C15116.7 (5)
C24—N3—Cu1111.4 (3)C24—C16—C17118.0 (5)
C22—N4—C23117.9 (4)C15—C16—C17125.3 (5)
C22—N4—Cu1130.0 (3)C18—C17—C16121.6 (5)
C23—N4—Cu1112.1 (3)C18—C17—H17119.2
O2—N5—C25123.7 (4)C16—C17—H17119.2
O2—N5—Cu1120.9 (3)C17—C18—C19122.2 (5)
C25—N5—Cu1115.3 (3)C17—C18—H18118.9
C26—N6—O1117.2 (4)C19—C18—H18118.9
C26—N6—Cu1116.4 (3)C23—C19—C20117.0 (5)
O1—N6—Cu1125.3 (3)C23—C19—C18117.1 (5)
O7—N7—O6120.1 (5)C20—C19—C18125.9 (5)
O7—N7—O5119.4 (5)C21—C20—C19118.9 (5)
O6—N7—O5120.3 (5)C21—C20—H20120.6
O10—N8—O8131.8 (13)C19—C20—H20120.6
O10—N8—O9118.5 (11)C20—C21—C22121.0 (5)
O8—N8—O9109.5 (11)C20—C21—H21119.5
N1—C1—C2121.5 (5)C22—C21—H21119.5
N1—C1—H1119.2N4—C22—C21121.8 (4)
C2—C1—H1119.2N4—C22—H22119.1
C3—C2—C1120.4 (5)C21—C22—H22119.1
C3—C2—H2119.8N4—C23—C19123.5 (4)
C1—C2—H2119.8N4—C23—C24116.3 (4)
C2—C3—C4120.2 (5)C19—C23—C24120.2 (4)
C2—C3—H3119.9N3—C24—C16123.1 (4)
C4—C3—H3119.9N3—C24—C23116.1 (4)
C3—C4—C12116.7 (5)C16—C24—C23120.8 (4)
C3—C4—C5125.3 (5)N5—C25—C26113.1 (4)
C12—C4—C5117.9 (5)N5—C25—O3121.9 (5)
C6—C5—C4121.5 (5)C26—C25—O3124.8 (5)
C6—C5—H5119.2N6—C26—C25113.8 (4)
C4—C5—H5119.2N6—C26—O4124.0 (5)
C5—C6—C7120.7 (5)C25—C26—O4122.2 (5)
C5—C6—H6119.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O6i0.932.553.289 (6)137
C18—H18···O2ii0.932.423.269 (7)152
C5—H5···O1iii0.932.553.354 (6)145
C3—H3···O5iv0.932.543.387 (7)151
O1—H1A···O6v0.822.002.697 (5)143
O1—H1A···O5v0.822.362.991 (5)134
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, −y+1, −z; (iii) −x+1, −y+2, −z; (iv) −x+1, −y+1, −z+1; (v) x, y+1, z−1.
Selected geometric parameters (Å, º) top
Cu1—N11.933 (4)Cu1—N41.950 (3)
Cu1—N21.999 (4)Cu1—N51.906 (4)
Cu1—N31.959 (4)Cu1—N61.889 (4)
N1—Cu1—N283.30 (16)N2—Cu1—N695.51 (15)
N1—Cu1—N392.39 (15)N3—Cu1—N483.97 (15)
N1—Cu1—N4175.33 (15)N3—Cu1—N593.86 (17)
N1—Cu1—N593.57 (16)N3—Cu1—N6174.47 (16)
N1—Cu1—N690.45 (15)N4—Cu1—N589.60 (15)
N2—Cu1—N389.54 (15)N4—Cu1—N693.42 (15)
N2—Cu1—N493.71 (15)N5—Cu1—N681.23 (17)
N2—Cu1—N5175.49 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O6i0.932.553.289 (6)137
C18—H18···O2ii0.932.423.269 (7)152
C5—H5···O1iii0.932.553.354 (6)145
C3—H3···O5iv0.932.543.387 (7)151
O1—H1A···O6v0.822.002.697 (5)143
O1—H1A···O5v0.822.362.991 (5)134
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, −y+1, −z; (iii) −x+1, −y+2, −z; (iv) −x+1, −y+1, −z+1; (v) x, y+1, z−1.
Acknowledgements top

This work was supported by the Science and Technology Bureau of Jian, Jiangxi Province of China (grant No. 20052817).

references
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