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Acta Cryst. (2007). E63, m2007    [ doi:10.1107/S1600536807030747 ]

Bis([mu]-biphenyl-2,2'-dicarboxylato)bis[(2,2'-bipyridine)copper(II)] tetrahydrate

H.-Y. He, Y.-L. Zhou and J. Gao

Abstract top

The title compound, [Cu2(C14H8O4)2(C10H8N2)2]·4H2O, contains a centrosymmetric binuclear copper(II) complex, with Cu...Cu = 5.6865 (16) Å. The Cu atom displays a cis-CuN2O2 square-planar geometry, although two long (>2.6 Å) Cu...O contacts complete a distorted cis-CuN2O4 octahedron. The crystal packing is consolidated by O-H...O hydrogen bonds to form infinite chains. One water molecule is disordered over two sites, with occupancy factors of ca 0.7 and 0.3.

Comment top

Binuclear copper(II) complexes have been intensely investigated owing to their potential application as magnetic materials and catalysts (Zhu et al., 2001). Here we present the synthesis and crystal structure of the title compound, (I), [Cu2(dpa)2(bipy)2]·4H2O (dpa = the diphenyl-2,2'dicarboxylato dianion and bipy = 2,2'-bipyridine), which contains a centrosymmetric binuclear complex. The copper(II) atom adopts a distorted square geometry (Table 1, Fig. 1). The bipy ligand shows its classical bidentate coordination mode, albeit with a shorter mean Cu—N bond length than in the related complex [Cu2(C2O4)(C12H8N2)2(C3H7NO)2](ClO4)2 (Wang et al., 2006). The dpa ligand adopts a µ2-bridged coordination and the dihedral angle between its aromatic rings is 86.7 (2)°. As well as the short Cu—O bonds, two long (> 2.60 Å) Cu—O contacts that might be regarded as secondary bonds (He & Zhu, 2003) complete a distorted octahedron. The Cu···Cui (i = 1 − x, 1 − y, 1 − z) distance bridged by the dpa ligands is 5.6865 (16) Å.

The complex (I) is extended into one dimensional framework by O—H···O hydrogen bonds (Table 2, Fig.2).

Related literature top

For related literature, see: He & Zhu (2003); Wang et al. (2006); Zhu et al. (2001).

Experimental top

0.0705 g (0.3 mmol) Cu(NO3)2·6H2O, 0.0734 g diphenyl-2,2'-dicarboxyl acid) and 0.0473 g 2,2'-bipyridine were dissolved in 20 ml water, to obtain a blue solution. After about two weeks at room temperature, blue plates of (I) were obtained and filtered off.

Refinement top

The C-bound H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The water H atoms were located in a diference map and refined with a distance restraint of O—H = 0.85 (1) Å and the constraint Uiso(H) = 1.5Ueq(O). Due to the disorder of the water molecules the location of their H atoms should be regarded as less certain.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level (arbitrary spheres for the H atoms).
[Figure 2] Fig. 2. The one dimensional chain in (I) formed by O—H···O hydrogen bongs. Displacement ellipsoids are drawn at the 30% probability level. The bipy ligands are omitted for clarity.
Bis(µ-biphenyl-2,2'-dicarboxylato)bis[(2,2'-bipyridine)copper(II)] tetrahydrate top
Crystal data top
[Cu2(C14H8O4)2(C10H8N2)2]·4H2OF000 = 1020
Mr = 991.92Dx = 1.496 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 15487 reflections
a = 11.428 (3) Åθ = 2.0–25º
b = 9.816 (2) ŵ = 1.04 mm−1
c = 19.774 (4) ÅT = 293 (2) K
β = 97.098 (4)ºPlate, blue
V = 2201.2 (9) Å30.19 × 0.12 × 0.02 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer		3875 independent reflections
Radiation source: fine-focus sealed tube2635 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.091
T = 293(2) Kθmax = 25.0º
ω scansθmin = 2.0º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.827, Tmax = 0.980k = −11→11
15487 measured reflectionsl = −23→23
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difmap and geom
R[F2 > 2σ(F2)] = 0.058H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.132  w = 1/[σ2(Fo2) + (0.0523P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3875 reflectionsΔρmax = 0.40 e Å−3
326 parametersΔρmin = −0.39 e Å−3
9 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Cu2(C14H8O4)2(C10H8N2)2]·4H2OV = 2201.2 (9) Å3
Mr = 991.92Z = 2
Monoclinic, P21/nMo Kα
a = 11.428 (3) ŵ = 1.04 mm−1
b = 9.816 (2) ÅT = 293 (2) K
c = 19.774 (4) Å0.19 × 0.12 × 0.02 mm
β = 97.098 (4)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		3875 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2635 reflections with I > 2σ(I)
Tmin = 0.827, Tmax = 0.980Rint = 0.091
15487 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0589 restraints
wR(F2) = 0.132H atoms treated by a mixture of
independent and constrained refinement
S = 1.02Δρmax = 0.40 e Å−3
3875 reflectionsΔρmin = −0.39 e Å−3
326 parameters
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*/UeqOcc. (<1)
O3−0.1297 (3)−0.3198 (3)−0.11357 (19)0.0617 (10)
C24−0.0584 (4)−0.2244 (4)−0.1138 (2)0.0349 (11)
O4−0.0740 (2)−0.1116 (3)−0.08590 (14)0.0358 (7)
O5−0.1362 (3)0.2058 (4)−0.02708 (18)0.0670 (11)
O6−0.2335 (5)−0.5841 (6)−0.1210 (4)0.095 (3)0.703 (7)
O6'−0.1884 (17)−0.515 (2)−0.0306 (11)0.192 (11)0.297 (7)
H6A−0.201 (8)−0.639 (4)−0.091 (3)0.288*0.703 (7)
H6B−0.204 (8)−0.505 (3)−0.112 (5)0.288*0.703 (7)
H6B'−0.202 (6)−0.53 (3)−0.073 (3)0.288*0.297 (7)
H6A'−0.114 (3)−0.51 (3)−0.020 (5)0.288*0.297 (7)
H5B−0.066 (2)0.223 (9)−0.036 (3)0.288*
H5A−0.132 (6)0.170 (8)0.012 (2)0.288*
Cu10.21213 (4)0.14650 (5)0.03932 (2)0.03214 (16)
O20.2010 (2)0.0042 (3)−0.07275 (14)0.0422 (8)
O10.1142 (2)0.1934 (3)−0.04561 (14)0.0377 (7)
N20.3250 (3)0.0462 (3)0.10571 (16)0.0343 (9)
N10.3617 (3)0.2201 (3)0.01224 (16)0.0332 (9)
C180.1004 (3)−0.1420 (4)−0.1838 (2)0.0314 (10)
C110.1296 (3)0.0982 (4)−0.0884 (2)0.0290 (10)
C50.4607 (3)0.1641 (4)0.0449 (2)0.0334 (10)
C120.0576 (3)0.1050 (4)−0.15634 (19)0.0305 (10)
C170.0412 (3)−0.0076 (4)−0.1992 (2)0.0329 (10)
C230.0521 (3)−0.2448 (4)−0.1464 (2)0.0308 (10)
C60.4389 (3)0.0638 (4)0.0973 (2)0.0322 (10)
C80.4958 (4)−0.0963 (5)0.1854 (2)0.0536 (14)
H80.5538−0.14420.21270.064*
C16−0.0338 (4)0.0043 (5)−0.2599 (2)0.0385 (11)
H16−0.0467−0.0713−0.28820.046*
C220.1106 (4)−0.3689 (5)−0.1356 (2)0.0427 (12)
H220.0785−0.4369−0.11070.051*
C130.0006 (4)0.2268 (4)−0.1761 (2)0.0375 (11)
H130.01110.3026−0.14790.045*
C15−0.0894 (4)0.1248 (5)−0.2792 (2)0.0487 (13)
H15−0.13870.1307−0.32020.058*
C70.5268 (4)−0.0085 (5)0.1364 (2)0.0441 (12)
H70.60540.00230.12970.053*
C190.2051 (4)−0.1712 (4)−0.2100 (2)0.0408 (12)
H190.2373−0.1056−0.23620.049*
C20.4777 (4)0.3556 (5)−0.0524 (3)0.0559 (14)
H20.48170.4218−0.08570.067*
C200.2626 (4)−0.2930 (5)−0.1986 (2)0.0496 (13)
H200.3333−0.3082−0.21620.060*
C100.2967 (4)−0.0408 (4)0.1524 (2)0.0430 (12)
H100.2174−0.05300.15720.052*
C40.5699 (4)0.2020 (5)0.0290 (2)0.0472 (13)
H40.63780.16230.05150.057*
C14−0.0716 (4)0.2355 (5)−0.2377 (2)0.0460 (13)
H14−0.10820.3176−0.25080.055*
C10.3707 (4)0.3143 (5)−0.0355 (2)0.0507 (13)
H10.30240.3529−0.05790.061*
C210.2161 (4)−0.3922 (5)−0.1615 (2)0.0492 (13)
H210.2550−0.4750−0.15360.059*
C30.5780 (4)0.2990 (5)−0.0201 (3)0.0576 (15)
H30.65130.3257−0.03130.069*
C90.3793 (4)−0.1136 (5)0.1939 (2)0.0520 (14)
H90.3571−0.17280.22670.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.057 (2)0.043 (2)0.090 (3)−0.0187 (17)0.0289 (19)−0.0131 (18)
C240.036 (2)0.038 (3)0.029 (2)−0.002 (2)−0.0003 (19)0.008 (2)
O40.0300 (15)0.0339 (17)0.0458 (18)−0.0023 (13)0.0140 (14)−0.0038 (14)
O50.050 (2)0.088 (3)0.063 (2)0.015 (2)0.0054 (18)0.009 (2)
O60.071 (4)0.060 (4)0.151 (7)−0.010 (3)−0.005 (4)0.038 (4)
O6'0.24 (2)0.095 (15)0.28 (3)0.015 (15)0.16 (2)0.057 (16)
Cu10.0225 (3)0.0413 (3)0.0322 (3)0.0016 (2)0.0020 (2)0.0023 (3)
O20.0353 (17)0.0431 (18)0.0443 (19)0.0077 (14)−0.0101 (14)−0.0023 (15)
O10.0327 (16)0.0478 (19)0.0311 (16)0.0110 (14)−0.0023 (13)−0.0057 (14)
N20.0287 (19)0.044 (2)0.030 (2)−0.0011 (16)0.0006 (15)0.0037 (17)
N10.034 (2)0.036 (2)0.029 (2)−0.0029 (16)0.0020 (16)0.0042 (16)
C180.031 (2)0.034 (2)0.029 (2)−0.0021 (19)0.0016 (18)−0.004 (2)
C110.021 (2)0.032 (2)0.034 (2)−0.0012 (18)0.0039 (18)0.003 (2)
C50.026 (2)0.036 (3)0.038 (3)0.0020 (19)0.0039 (19)−0.010 (2)
C120.027 (2)0.038 (3)0.026 (2)−0.0052 (18)0.0019 (17)0.0020 (19)
C170.029 (2)0.038 (3)0.033 (2)−0.0057 (19)0.0098 (19)0.004 (2)
C230.030 (2)0.036 (3)0.027 (2)−0.0016 (19)0.0031 (19)−0.0040 (19)
C60.028 (2)0.036 (2)0.032 (2)0.0040 (19)0.0007 (18)−0.006 (2)
C80.051 (3)0.058 (3)0.047 (3)0.010 (2)−0.011 (2)0.011 (3)
C160.037 (3)0.045 (3)0.033 (3)−0.002 (2)−0.001 (2)0.002 (2)
C220.047 (3)0.041 (3)0.040 (3)0.003 (2)0.006 (2)−0.003 (2)
C130.040 (3)0.035 (3)0.038 (3)−0.001 (2)0.007 (2)0.007 (2)
C150.042 (3)0.064 (3)0.036 (3)−0.002 (2)−0.008 (2)0.012 (2)
C70.033 (3)0.058 (3)0.040 (3)0.003 (2)−0.001 (2)0.000 (2)
C190.035 (2)0.047 (3)0.041 (3)0.000 (2)0.008 (2)0.000 (2)
C20.061 (3)0.051 (3)0.058 (3)−0.011 (3)0.019 (3)0.016 (3)
C200.036 (3)0.066 (3)0.049 (3)0.009 (2)0.012 (2)−0.007 (3)
C100.038 (3)0.043 (3)0.048 (3)−0.002 (2)0.008 (2)0.003 (2)
C40.032 (3)0.052 (3)0.057 (3)0.000 (2)0.007 (2)0.000 (3)
C140.045 (3)0.045 (3)0.048 (3)0.008 (2)0.002 (2)0.015 (2)
C10.048 (3)0.053 (3)0.051 (3)−0.003 (2)0.008 (2)0.014 (3)
C210.050 (3)0.046 (3)0.051 (3)0.018 (2)0.003 (2)−0.006 (2)
C30.045 (3)0.062 (3)0.069 (4)−0.005 (3)0.023 (3)0.002 (3)
C90.054 (3)0.051 (3)0.049 (3)−0.001 (2)0.000 (2)0.019 (2)
Geometric parameters (Å, °) top
O3—C241.242 (5)C23—C221.394 (6)
C24—O41.260 (5)C6—C71.385 (5)
C24—C231.500 (6)C8—C91.372 (6)
C24—Cu1i2.545 (4)C8—C71.375 (6)
O4—Cu1i1.953 (3)C8—H80.9300
O5—H5B0.855 (18)C16—C151.375 (6)
O5—H5A0.86 (2)C16—H160.9300
O6—H6A0.85 (2)C22—C211.386 (6)
O6—H6B0.86 (2)C22—H220.9300
O6—H6B'1.09 (8)C13—C141.387 (6)
O6'—H6B'0.85 (2)C13—H130.9300
O6'—H6A'0.85 (2)C15—C141.361 (6)
Cu1—O4i1.953 (3)C15—H150.9300
Cu1—O11.955 (3)C7—H70.9300
Cu1—N21.984 (3)C19—C201.369 (6)
Cu1—N11.989 (3)C19—H190.9300
O2—C111.245 (4)C2—C31.360 (6)
O1—C111.287 (5)C2—C11.368 (6)
N2—C101.326 (5)C2—H20.9300
N2—C61.343 (5)C20—C211.366 (6)
N1—C11.334 (5)C20—H200.9300
N1—C51.348 (5)C10—C91.373 (6)
C18—C191.392 (5)C10—H100.9300
C18—C231.404 (6)C4—C31.371 (6)
C18—C171.496 (5)C4—H40.9300
C11—C121.488 (5)C14—H140.9300
C5—C41.376 (6)C1—H10.9300
C5—C61.474 (6)C21—H210.9300
C12—C171.391 (5)C3—H30.9300
C12—C131.394 (6)C9—H90.9300
C17—C161.392 (5)
O3—C24—O4122.2 (4)C7—C6—C5124.1 (4)
O3—C24—C23119.2 (4)C9—C8—C7120.2 (4)
O4—C24—C23118.5 (4)C9—C8—H8119.9
O3—C24—Cu1i74.0 (3)C7—C8—H8119.9
O4—C24—Cu1i48.49 (19)C15—C16—C17121.8 (4)
C23—C24—Cu1i165.1 (3)C15—C16—H16119.1
C24—O4—Cu1i102.6 (2)C17—C16—H16119.1
H5B—O5—H5A109 (3)C21—C22—C23120.7 (4)
H6A—O6—H6B108 (3)C21—C22—H22119.7
H6A—O6—H6B'68 (10)C23—C22—H22119.7
H6B—O6—H6B'48 (10)C14—C13—C12120.4 (4)
H6B'—O6'—H6A'109 (4)C14—C13—H13119.8
O4i—Cu1—O192.09 (12)C12—C13—H13119.8
O4i—Cu1—N295.61 (13)C14—C15—C16119.3 (4)
O1—Cu1—N2160.33 (13)C14—C15—H15120.3
O4i—Cu1—N1164.13 (13)C16—C15—H15120.3
O1—Cu1—N195.89 (12)C8—C7—C6118.8 (4)
N2—Cu1—N181.29 (13)C8—C7—H7120.6
O4i—Cu1—C24i28.88 (12)C6—C7—H7120.6
O1—Cu1—C24i93.65 (12)C20—C19—C18122.4 (4)
N2—Cu1—C24i101.82 (13)C20—C19—H19118.8
N1—Cu1—C24i136.39 (14)C18—C19—H19118.8
C11—O1—Cu1106.5 (2)C3—C2—C1119.4 (5)
C10—N2—C6119.5 (4)C3—C2—H2120.3
C10—N2—Cu1125.8 (3)C1—C2—H2120.3
C6—N2—Cu1114.5 (3)C21—C20—C19120.0 (4)
C1—N1—C5119.2 (4)C21—C20—H20120.0
C1—N1—Cu1125.9 (3)C19—C20—H20120.0
C5—N1—Cu1114.9 (3)N2—C10—C9122.8 (4)
C19—C18—C23117.4 (4)N2—C10—H10118.6
C19—C18—C17119.6 (4)C9—C10—H10118.6
C23—C18—C17122.9 (4)C3—C4—C5119.4 (4)
O2—C11—O1120.9 (4)C3—C4—H4120.3
O2—C11—C12122.0 (4)C5—C4—H4120.3
O1—C11—C12117.1 (3)C15—C14—C13120.6 (4)
N1—C5—C4120.8 (4)C15—C14—H14119.7
N1—C5—C6113.9 (3)C13—C14—H14119.7
C4—C5—C6125.3 (4)N1—C1—C2121.9 (5)
C17—C12—C13119.2 (4)N1—C1—H1119.1
C17—C12—C11122.1 (4)C2—C1—H1119.1
C13—C12—C11118.6 (4)C20—C21—C22119.7 (4)
C12—C17—C16118.7 (4)C20—C21—H21120.2
C12—C17—C18123.6 (4)C22—C21—H21120.2
C16—C17—C18117.7 (4)C2—C3—C4119.3 (5)
C22—C23—C18119.8 (4)C2—C3—H3120.3
C22—C23—C24117.7 (4)C4—C3—H3120.3
C18—C23—C24122.5 (4)C8—C9—C10117.9 (4)
N2—C6—C7120.8 (4)C8—C9—H9121.1
N2—C6—C5115.1 (3)C10—C9—H9121.1
O3—C24—O4—Cu1i7.1 (5)C17—C18—C23—C24−5.0 (6)
C23—C24—O4—Cu1i−170.9 (3)O3—C24—C23—C22−40.9 (6)
O4i—Cu1—O1—C11−111.8 (2)O4—C24—C23—C22137.2 (4)
N2—Cu1—O1—C111.4 (5)Cu1i—C24—C23—C22109.9 (11)
N1—Cu1—O1—C1181.9 (3)O3—C24—C23—C18142.3 (4)
C24i—Cu1—O1—C11−140.7 (3)O4—C24—C23—C18−39.6 (6)
O4i—Cu1—N2—C1015.1 (4)Cu1i—C24—C23—C18−66.9 (12)
O1—Cu1—N2—C10−97.5 (5)C10—N2—C6—C70.5 (6)
N1—Cu1—N2—C10179.4 (4)Cu1—N2—C6—C7−174.8 (3)
C24i—Cu1—N2—C1043.7 (4)C10—N2—C6—C5−179.2 (4)
O4i—Cu1—N2—C6−170.0 (3)Cu1—N2—C6—C55.6 (5)
O1—Cu1—N2—C677.4 (5)N1—C5—C6—N2−1.6 (5)
N1—Cu1—N2—C6−5.7 (3)C4—C5—C6—N2177.8 (4)
C24i—Cu1—N2—C6−141.4 (3)N1—C5—C6—C7178.8 (4)
O4i—Cu1—N1—C1−97.5 (6)C4—C5—C6—C7−1.8 (7)
O1—Cu1—N1—C122.3 (4)C12—C17—C16—C151.6 (6)
N2—Cu1—N1—C1−177.3 (4)C18—C17—C16—C15−178.2 (4)
C24i—Cu1—N1—C1−79.3 (4)C18—C23—C22—C21−0.1 (6)
O4i—Cu1—N1—C584.6 (6)C24—C23—C22—C21−177.0 (4)
O1—Cu1—N1—C5−155.6 (3)C17—C12—C13—C140.1 (6)
N2—Cu1—N1—C54.8 (3)C11—C12—C13—C14−177.1 (4)
C24i—Cu1—N1—C5102.8 (3)C17—C16—C15—C14−0.5 (7)
Cu1—O1—C11—O2−3.4 (4)C9—C8—C7—C61.4 (7)
Cu1—O1—C11—C12175.8 (3)N2—C6—C7—C8−1.6 (7)
C1—N1—C5—C4−0.6 (6)C5—C6—C7—C8178.0 (4)
Cu1—N1—C5—C4177.4 (3)C23—C18—C19—C20−2.0 (6)
C1—N1—C5—C6178.8 (4)C17—C18—C19—C20−179.0 (4)
Cu1—N1—C5—C6−3.2 (4)C18—C19—C20—C211.3 (7)
O2—C11—C12—C1717.5 (6)C6—N2—C10—C90.9 (7)
O1—C11—C12—C17−161.7 (4)Cu1—N2—C10—C9175.6 (3)
O2—C11—C12—C13−165.4 (4)N1—C5—C4—C30.6 (7)
O1—C11—C12—C1315.3 (5)C6—C5—C4—C3−178.7 (4)
C13—C12—C17—C16−1.4 (6)C16—C15—C14—C13−0.8 (7)
C11—C12—C17—C16175.7 (4)C12—C13—C14—C151.1 (7)
C13—C12—C17—C18178.4 (4)C5—N1—C1—C20.1 (7)
C11—C12—C17—C18−4.5 (6)Cu1—N1—C1—C2−177.7 (4)
C19—C18—C17—C12−94.7 (5)C3—C2—C1—N10.4 (8)
C23—C18—C17—C1288.5 (5)C19—C20—C21—C220.1 (7)
C19—C18—C17—C1685.1 (5)C23—C22—C21—C20−0.7 (7)
C23—C18—C17—C16−91.8 (5)C1—C2—C3—C4−0.4 (8)
C19—C18—C23—C221.4 (6)C5—C4—C3—C2−0.1 (8)
C17—C18—C23—C22178.3 (4)C7—C8—C9—C10−0.1 (7)
C19—C18—C23—C24178.1 (4)N2—C10—C9—C8−1.1 (7)
Symmetry codes: (i) −x, −y, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O2ii0.85 (5)2.29 (7)3.009 (5)144 (6)
O5—H5B···O10.86 (3)2.11 (3)2.932 (4)160 (8)
O6—H6A···O5iii0.85 (6)2.06 (5)2.903 (8)171 (7)
O6—H6B···O30.86 (5)2.01 (5)2.849 (7)167 (9)
Symmetry codes: (ii) −x, −y, −z; (iii) x, y−1, z.
Table 1
Selected geometric parameters (Å) top
Cu1—O4i1.953 (3)Cu1—N21.984 (3)
Cu1—O11.955 (3)Cu1—N11.989 (3)
Symmetry codes: (i) −x, −y, −z.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O2ii0.85 (5)2.29 (7)3.009 (5)144 (6)
O5—H5B···O10.86 (3)2.11 (3)2.932 (4)160 (8)
O6—H6A···O5iii0.85 (6)2.06 (5)2.903 (8)171 (7)
O6—H6B···O30.86 (5)2.01 (5)2.849 (7)167 (9)
Symmetry codes: (ii) −x, −y, −z; (iii) x, y−1, z.
references
References top

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Sheldrick, G. M. (1996). SADABS. University of Göttingen,Germany.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Wang, H.-D., Zhou, Y.-L., He, H.-Y., Tu, X.-H. & Zhu, L.-G. (2006). Acta Cryst. E62, m1081–m1082.

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