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Acta Cryst. (2007). E63, m2496-m2497    [ doi:10.1107/S1600536807043267 ]

Aqua(azido)([mu]-azido)bis{2-[(2-dimethylaminoethylimino)methyl]-6-methoxyphenolato}dicopper(II) monohydrate

Y.-P. Diao and K. Li

Abstract top

The asymmetric unit of the title compound, [Cu2(C12H17N2O2)2(N3)([mu]-N3)(H2O)]·H2O, consists of a dinuclear complex molecule and a solvent water molecule. One Cu atom is six-coordinated by the phenol O atom and by one imine and one amine N atoms from one Schiff base ligand, the phenol and ether O atoms of the second Schiff base, together with a terminal N atom of the bridging azide ligand, in an octahedral geometry. The coordination environment of the second Cu atom contains a phenol O and imine and amine N atoms from one Schiff base ligand, two further N atoms, one from the bridging and the other from a terminal azide ligand, and a coordinated water molecule, also in an octahedral geometry. The crystal structure involves O-H...N and O-H...O hydrogen bonds.

Comment top

Polynuclear complexes play an important role in the development of coordination chemistry (Eshel et al., 2000; Jiang et al., 2005; Escuer et al., 2000; El-Behairy et al., 1997; Manhas et al., 2005). Some of the complexes have been found to have pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). A prime strategy for designing these molecular materials is to use suitable bridging ligands (Salem, 2005; Dohlakiya & Patel, 2005; Dey et al., 2004). The azide ligand displays a number of coordination modes and has become one of the most extensively studied building blocks in the field. We recently reported the structure of an azide-bridged polynuclear copper(II) complex (Diao, 2007) and we report herein the crystal structure of the related title complex (I), Fig 1.

The complex is an azide-bridged dinuclear copper(II) complex. One Cu atom is six-coordinated by the phenolic O atom, one imine, and one amine N atoms from one Schiff base ligand, the phenolic and ether O atoms of the second Schiff base, together with a terminal N atom of the bridging azide ligand, in an octahedral geometry. The coordination sphere of the second Cu atom contains a phenolic O, imine and amine N atoms from one Schiff base ligand, two N atoms one from the bridging and the other from a terminal azide ligand, and a coordinated water molecule, also in an octahedral geometry.

Related literature top

For background on the chemistry of polynuclear complexes, see: Eshel et al. (2000); Jiang et al. (2005); Escuer et al. (2000); El-Behairy et al. (1997); Manhas et al. (2005). For their biological activity, see: Brückner et al. (2000); Harrop et al. (2003); Ren et al. (2002). For polynuclear complexes involving bridging ligands, see: Salem (2005); Dohlakiya & Patel (2005); Dey et al. (2004). For a related structure, see: Diao (2007).

Experimental top

2-Hydroxy-3-methoxybenzaldehyde (0.2 mmol, 30.5 mg), N,N-dimethylethane-1,2-diamine (0.2 mmol, 17.5 mg), NaN3 (0.2 mmol, 13.0 mg), and Cu(CH3COO)2·H2O (0.2 mmol, 40.0 mg) were dissolved in an 95% ethanol solution (30 ml). The mixture was stirred at room temperature for 30 min to give a deep blue solution. After keeping the solution in air for a few days, deep blue crystals were formed.

Refinement top

The crystals were very weakly diffracting and few high angle reflections were obtained. This explains the low measured fraction of data in this determination. Water H atoms were located from a difference Fourier map and refined isotropically. All other H atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso = 1.2Ueq (C) for aromatic, 0.97 Å, Uiso = 1.2Ueq (C) for CH2 and 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. The structure of the complex with displacement parameters drawn at the 30% probability level. Hydrogen atoms have been omitted for clarity.
Aqua(azido)(µ-azido)bis{2-[(2-dimethylaminoethylimino)methyl]- 6-methoxyphenolato}dicopper(II) monohydrate top
Crystal data top
[Cu2(C12H17N2O2)2(N3)2(H2O)]·H2OF000 = 1432
Mr = 689.72Dx = 1.548 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2127 reflections
a = 16.232 (3) Åθ = 2.4–25.3º
b = 13.540 (2) ŵ = 1.49 mm−1
c = 13.997 (3) ÅT = 293 (2) K
β = 105.821 (2)ºBlock, deep blue
V = 2959.7 (9) Å30.45 × 0.40 × 0.38 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		6982 independent reflections
Radiation source: fine-focus sealed tube4183 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.083
T = 293(2) Kθmax = 28.3º
ω scansθmin = 1.3º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −20→20
Tmin = 0.553, Tmax = 0.601k = −17→18
25203 measured reflectionsl = −18→18
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)] = 0.066H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.178  w = 1/[σ2(Fo2) + (0.082P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
6982 reflectionsΔρmax = 0.85 e Å−3
397 parametersΔρmin = −0.53 e Å−3
6 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Cu2(C12H17N2O2)2(N3)2(H2O)]·H2OV = 2959.7 (9) Å3
Mr = 689.72Z = 4
Monoclinic, P21/cMo Kα
a = 16.232 (3) ŵ = 1.49 mm−1
b = 13.540 (2) ÅT = 293 (2) K
c = 13.997 (3) Å0.45 × 0.40 × 0.38 mm
β = 105.821 (2)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		6982 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		4183 reflections with I > 2σ(I)
Tmin = 0.553, Tmax = 0.601Rint = 0.083
25203 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0666 restraints
wR(F2) = 0.178H atoms treated by a mixture of
independent and constrained refinement
S = 1.02Δρmax = 0.85 e Å−3
6982 reflectionsΔρmin = −0.53 e Å−3
397 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*/Ueq
Cu10.22488 (4)0.59328 (4)0.30915 (4)0.03150 (18)
Cu20.28782 (4)0.41861 (4)0.46588 (4)0.03647 (19)
O10.3838 (2)0.7739 (2)0.5713 (2)0.0438 (9)
O20.2983 (2)0.6832 (2)0.4120 (2)0.0352 (8)
O30.1096 (2)0.6710 (2)0.3377 (2)0.0392 (8)
O40.19356 (19)0.5165 (2)0.4158 (2)0.0304 (7)
O5W0.3560 (2)0.5452 (2)0.5539 (3)0.0452 (9)
O6W0.1580 (5)0.9882 (5)0.3801 (7)0.138 (3)
N10.2379 (2)0.6839 (3)0.2025 (3)0.0325 (9)
N20.1402 (2)0.5160 (3)0.1842 (3)0.0353 (9)
N30.2400 (3)0.3880 (3)0.5808 (3)0.0411 (10)
N40.3881 (3)0.3180 (3)0.5377 (3)0.0473 (11)
N50.2209 (4)0.3096 (4)0.3707 (3)0.0614 (14)
N60.1723 (3)0.2499 (4)0.3811 (4)0.0616 (14)
N70.1258 (4)0.1903 (5)0.3929 (7)0.134 (3)
N80.3252 (3)0.4832 (3)0.3445 (3)0.0370 (9)
N90.3824 (3)0.4609 (3)0.3142 (3)0.0497 (11)
N100.4393 (4)0.4366 (5)0.2847 (5)0.094 (2)
C10.3224 (3)0.7735 (3)0.3996 (3)0.0292 (10)
C20.3684 (3)0.8273 (3)0.4848 (4)0.0358 (11)
C30.3930 (3)0.9227 (4)0.4769 (4)0.0477 (13)
H30.42140.95710.53380.057*
C40.3763 (4)0.9686 (4)0.3858 (5)0.0549 (15)
H40.39301.03380.38160.066*
C50.3355 (4)0.9186 (3)0.3019 (4)0.0473 (13)
H50.32560.94960.24060.057*
C60.3079 (3)0.8201 (3)0.3068 (4)0.0345 (11)
C70.4359 (4)0.8197 (5)0.6593 (4)0.0646 (18)
H7A0.49020.83730.64930.097*
H7B0.44460.77440.71390.097*
H7C0.40780.87800.67360.097*
C80.2659 (3)0.7731 (3)0.2133 (3)0.0351 (11)
H80.25850.81080.15600.042*
C90.1970 (3)0.6477 (4)0.1016 (3)0.0418 (12)
H9A0.23590.60470.07930.050*
H9B0.18190.70270.05580.050*
C100.1179 (3)0.5917 (4)0.1052 (4)0.0413 (12)
H10A0.07600.63700.11840.050*
H10B0.09290.56030.04160.050*
C110.1836 (4)0.4311 (4)0.1517 (4)0.0564 (16)
H11A0.14540.40070.09470.085*
H11B0.19990.38380.20460.085*
H11C0.23380.45400.13470.085*
C120.0606 (4)0.4801 (4)0.2041 (4)0.0552 (15)
H12A0.03300.53360.22820.083*
H12B0.07400.42870.25310.083*
H12C0.02290.45460.14390.083*
C130.1423 (3)0.5545 (3)0.4650 (3)0.0301 (10)
C140.0934 (3)0.6376 (3)0.4233 (3)0.0341 (11)
C150.0346 (3)0.6781 (4)0.4664 (4)0.0455 (13)
H150.00130.73130.43630.055*
C160.0250 (3)0.6399 (5)0.5546 (4)0.0545 (16)
H16−0.01470.66760.58370.065*
C170.0733 (3)0.5619 (5)0.5986 (4)0.0510 (14)
H170.06710.53790.65840.061*
C180.1334 (3)0.5161 (4)0.5550 (4)0.0404 (12)
C190.0756 (4)0.7652 (4)0.2999 (5)0.0628 (17)
H19A0.01430.76160.27850.094*
H19B0.09700.78300.24470.094*
H19C0.09280.81400.35120.094*
C200.1824 (3)0.4335 (4)0.6068 (4)0.0444 (13)
H200.17010.41220.66450.053*
C210.2859 (4)0.3068 (5)0.6420 (5)0.0649 (18)
H21A0.28250.31370.70980.078*
H21B0.26040.24400.61630.078*
C220.3736 (5)0.3103 (6)0.6392 (6)0.089 (2)
H22A0.40220.25120.67110.107*
H22B0.40090.36640.67830.107*
C230.4751 (4)0.3570 (5)0.5539 (6)0.087 (2)
H23A0.51430.31740.60270.130*
H23B0.47690.42390.57700.130*
H23C0.49090.35510.49270.130*
C240.3826 (6)0.2214 (5)0.4905 (7)0.121 (4)
H24A0.38640.22900.42370.182*
H24B0.32890.19110.48960.182*
H24C0.42870.18050.52710.182*
H5WA0.339 (5)0.595 (4)0.516 (5)0.146*
H5WB0.398 (4)0.564 (5)0.603 (4)0.146*
H6WB0.193 (5)0.960 (5)0.351 (7)0.146*
H6WA0.163 (6)1.0516 (10)0.377 (8)0.146*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0369 (3)0.0282 (3)0.0286 (3)−0.0004 (2)0.0074 (2)0.0004 (2)
Cu20.0433 (4)0.0298 (3)0.0350 (3)0.0013 (3)0.0084 (3)0.0036 (2)
O10.047 (2)0.045 (2)0.0332 (19)−0.0109 (16)0.0007 (16)−0.0076 (16)
O20.0448 (19)0.0294 (17)0.0280 (17)−0.0084 (14)0.0039 (15)0.0026 (14)
O30.0408 (19)0.0353 (18)0.042 (2)0.0120 (15)0.0128 (16)0.0020 (15)
O40.0332 (17)0.0309 (17)0.0282 (17)0.0033 (13)0.0104 (14)0.0050 (13)
O5W0.054 (2)0.037 (2)0.038 (2)−0.0076 (17)0.0005 (17)0.0050 (16)
O6W0.136 (6)0.104 (5)0.193 (8)−0.007 (5)0.078 (5)−0.027 (6)
N10.035 (2)0.031 (2)0.029 (2)0.0001 (17)0.0049 (17)0.0046 (16)
N20.044 (2)0.033 (2)0.026 (2)−0.0020 (18)0.0043 (18)−0.0004 (17)
N30.054 (3)0.036 (2)0.033 (2)−0.004 (2)0.011 (2)0.0099 (18)
N40.053 (3)0.038 (2)0.045 (3)0.009 (2)0.005 (2)0.010 (2)
N50.088 (4)0.041 (3)0.044 (3)−0.011 (3)0.000 (3)−0.003 (2)
N60.046 (3)0.037 (3)0.088 (4)0.005 (2)−0.004 (3)0.001 (3)
N70.075 (5)0.067 (5)0.252 (10)−0.018 (4)0.034 (6)0.017 (6)
N80.038 (2)0.037 (2)0.040 (2)0.0066 (18)0.017 (2)0.0013 (18)
N90.059 (3)0.040 (3)0.055 (3)0.005 (2)0.023 (3)0.003 (2)
N100.103 (5)0.099 (5)0.103 (5)0.030 (4)0.067 (4)0.012 (4)
C10.026 (2)0.025 (2)0.036 (3)0.0001 (18)0.008 (2)−0.0030 (19)
C20.039 (3)0.032 (3)0.037 (3)0.000 (2)0.011 (2)−0.001 (2)
C30.049 (3)0.038 (3)0.053 (3)−0.013 (2)0.008 (3)−0.014 (3)
C40.068 (4)0.031 (3)0.068 (4)−0.016 (3)0.022 (3)−0.005 (3)
C50.064 (4)0.032 (3)0.051 (3)−0.005 (2)0.024 (3)0.007 (2)
C60.036 (3)0.026 (2)0.041 (3)−0.002 (2)0.011 (2)0.002 (2)
C70.057 (4)0.087 (5)0.041 (3)−0.030 (3)−0.003 (3)−0.006 (3)
C80.038 (3)0.036 (3)0.034 (3)0.002 (2)0.014 (2)0.006 (2)
C90.058 (3)0.039 (3)0.028 (3)−0.006 (2)0.011 (2)0.003 (2)
C100.044 (3)0.048 (3)0.029 (2)0.000 (2)0.003 (2)−0.002 (2)
C110.083 (5)0.040 (3)0.039 (3)0.004 (3)0.005 (3)−0.008 (2)
C120.052 (3)0.058 (4)0.050 (3)−0.024 (3)0.006 (3)−0.003 (3)
C130.024 (2)0.036 (3)0.029 (2)−0.0091 (19)0.0049 (19)−0.009 (2)
C140.030 (2)0.038 (3)0.033 (3)−0.005 (2)0.005 (2)−0.010 (2)
C150.032 (3)0.050 (3)0.056 (4)−0.002 (2)0.014 (3)−0.016 (3)
C160.043 (3)0.070 (4)0.057 (4)−0.006 (3)0.024 (3)−0.025 (3)
C170.044 (3)0.075 (4)0.038 (3)−0.015 (3)0.018 (3)−0.015 (3)
C180.036 (3)0.050 (3)0.039 (3)−0.015 (2)0.016 (2)−0.011 (2)
C190.073 (4)0.049 (4)0.065 (4)0.027 (3)0.016 (3)0.015 (3)
C200.047 (3)0.056 (3)0.031 (3)−0.018 (3)0.012 (2)0.004 (2)
C210.080 (5)0.062 (4)0.057 (4)0.004 (3)0.025 (4)0.028 (3)
C220.087 (6)0.089 (6)0.086 (6)0.028 (4)0.013 (4)0.050 (4)
C230.047 (4)0.071 (5)0.139 (7)0.019 (3)0.018 (4)0.016 (5)
C240.122 (7)0.062 (5)0.142 (8)0.048 (5)−0.027 (6)−0.029 (5)
Geometric parameters (Å, °) top
Cu1—N11.987 (4)C5—C61.414 (6)
Cu1—O41.995 (3)C5—H50.9300
Cu1—O22.010 (3)C6—C81.448 (6)
Cu1—N82.163 (4)C7—H7A0.9600
Cu1—N22.176 (4)C7—H7B0.9600
Cu1—O32.275 (3)C7—H7C0.9600
Cu2—O42.001 (3)C8—H80.9300
Cu2—N32.010 (4)C9—C101.503 (7)
Cu2—N52.085 (5)C9—H9A0.9700
Cu2—N82.140 (4)C9—H9B0.9700
Cu2—N42.150 (4)C10—H10A0.9700
Cu2—O5W2.222 (3)C10—H10B0.9700
O1—C21.373 (6)C11—H11A0.9600
O1—C71.431 (6)C11—H11B0.9600
O2—C11.310 (5)C11—H11C0.9600
O3—C141.372 (6)C12—H12A0.9600
O3—C191.432 (6)C12—H12B0.9600
O4—C131.319 (5)C12—H12C0.9600
O5W—H5WA0.86 (6)C13—C181.407 (6)
O5W—H5WB0.86 (6)C13—C141.409 (7)
O6W—H6WB0.87 (8)C14—C151.373 (6)
O6W—H6WA0.866 (10)C15—C161.387 (7)
N1—C81.285 (6)C15—H150.9300
N1—C91.472 (6)C16—C171.358 (8)
N2—C121.476 (6)C16—H160.9300
N2—C101.478 (6)C17—C181.425 (7)
N2—C111.483 (6)C17—H170.9300
N3—C201.253 (7)C18—C201.448 (7)
N3—C211.467 (7)C19—H19A0.9600
N4—C241.456 (8)C19—H19B0.9600
N4—C231.466 (7)C19—H19C0.9600
N4—C221.506 (8)C20—H200.9300
N5—N61.166 (7)C21—C221.437 (9)
N6—N71.146 (7)C21—H21A0.9700
N8—N91.161 (6)C21—H21B0.9700
N9—N101.157 (7)C22—H22A0.9700
C1—C61.405 (6)C22—H22B0.9700
C1—C21.422 (6)C23—H23A0.9600
C2—C31.366 (6)C23—H23B0.9600
C3—C41.377 (8)C23—H23C0.9600
C3—H30.9300C24—H24A0.9600
C4—C51.360 (7)C24—H24B0.9600
C4—H40.9300C24—H24C0.9600
N1—Cu1—O4169.90 (14)O1—C7—H7A109.5
N1—Cu1—O290.00 (14)O1—C7—H7B109.5
O4—Cu1—O290.10 (12)H7A—C7—H7B109.5
N1—Cu1—N8111.68 (15)O1—C7—H7C109.5
O4—Cu1—N878.43 (14)H7A—C7—H7C109.5
O2—Cu1—N889.51 (14)H7B—C7—H7C109.5
N1—Cu1—N282.33 (15)N1—C8—C6125.7 (4)
O4—Cu1—N296.73 (13)N1—C8—H8117.1
O2—Cu1—N2171.31 (13)C6—C8—H8117.1
N8—Cu1—N297.11 (15)N1—C9—C10107.5 (4)
N1—Cu1—O396.18 (14)N1—C9—H9A110.2
O4—Cu1—O373.73 (12)C10—C9—H9A110.2
O2—Cu1—O387.11 (13)N1—C9—H9B110.2
N8—Cu1—O3151.94 (14)C10—C9—H9B110.2
N2—Cu1—O389.64 (14)H9A—C9—H9B108.5
O4—Cu2—N389.51 (15)N2—C10—C9109.8 (4)
O4—Cu2—N591.72 (17)N2—C10—H10A109.7
N3—Cu2—N596.77 (19)C9—C10—H10A109.7
O4—Cu2—N878.84 (13)N2—C10—H10B109.7
N3—Cu2—N8166.90 (16)C9—C10—H10B109.7
N5—Cu2—N889.60 (18)H10A—C10—H10B108.2
O4—Cu2—N4172.95 (15)N2—C11—H11A109.5
N3—Cu2—N484.47 (17)N2—C11—H11B109.5
N5—Cu2—N492.64 (19)H11A—C11—H11B109.5
N8—Cu2—N4106.72 (16)N2—C11—H11C109.5
O4—Cu2—O5W84.30 (13)H11A—C11—H11C109.5
N3—Cu2—O5W87.57 (15)H11B—C11—H11C109.5
N5—Cu2—O5W174.10 (16)N2—C12—H12A109.5
N8—Cu2—O5W85.36 (14)N2—C12—H12B109.5
N4—Cu2—O5W91.76 (15)H12A—C12—H12B109.5
C2—O1—C7117.0 (4)N2—C12—H12C109.5
C1—O2—Cu1127.7 (3)H12A—C12—H12C109.5
C14—O3—C19118.0 (4)H12B—C12—H12C109.5
C14—O3—Cu1111.4 (3)O4—C13—C18123.9 (4)
C19—O3—Cu1126.8 (3)O4—C13—C14117.4 (4)
C13—O4—Cu1120.9 (3)C18—C13—C14118.8 (4)
C13—O4—Cu2127.3 (3)O3—C14—C15125.0 (5)
Cu1—O4—Cu2106.29 (14)O3—C14—C13113.8 (4)
Cu2—O5W—H5WA104 (5)C15—C14—C13121.2 (5)
Cu2—O5W—H5WB146 (5)C14—C15—C16120.1 (5)
H5WA—O5W—H5WB109 (8)C14—C15—H15119.9
H6WB—O6W—H6WA109 (8)C16—C15—H15119.9
C8—N1—C9118.6 (4)C17—C16—C15120.2 (5)
C8—N1—Cu1126.8 (3)C17—C16—H16119.9
C9—N1—Cu1113.8 (3)C15—C16—H16119.9
C12—N2—C10108.8 (4)C16—C17—C18121.5 (5)
C12—N2—C11108.5 (4)C16—C17—H17119.3
C10—N2—C11110.4 (4)C18—C17—H17119.3
C12—N2—Cu1113.6 (3)C13—C18—C17118.2 (5)
C10—N2—Cu1103.8 (3)C13—C18—C20123.8 (5)
C11—N2—Cu1111.7 (3)C17—C18—C20118.0 (5)
C20—N3—C21119.9 (5)O3—C19—H19A109.5
C20—N3—Cu2127.8 (4)O3—C19—H19B109.5
C21—N3—Cu2112.1 (4)H19A—C19—H19B109.5
C24—N4—C23109.3 (6)O3—C19—H19C109.5
C24—N4—C22111.1 (6)H19A—C19—H19C109.5
C23—N4—C22105.6 (5)H19B—C19—H19C109.5
C24—N4—Cu2114.3 (4)N3—C20—C18125.9 (5)
C23—N4—Cu2114.7 (4)N3—C20—H20117.1
C22—N4—Cu2101.1 (3)C18—C20—H20117.1
N6—N5—Cu2131.6 (5)C22—C21—N3108.0 (5)
N7—N6—N5178.5 (7)C22—C21—H21A110.1
N9—N8—Cu2127.7 (4)N3—C21—H21A110.1
N9—N8—Cu1136.3 (4)C22—C21—H21B110.1
Cu2—N8—Cu196.01 (16)N3—C21—H21B110.1
N10—N9—N8178.5 (6)H21A—C21—H21B108.4
O2—C1—C6124.1 (4)C21—C22—N4116.0 (6)
O2—C1—C2118.3 (4)C21—C22—H22A108.3
C6—C1—C2117.6 (4)N4—C22—H22A108.3
C3—C2—O1125.6 (4)C21—C22—H22B108.3
C3—C2—C1121.0 (5)N4—C22—H22B108.3
O1—C2—C1113.4 (4)H22A—C22—H22B107.4
C2—C3—C4120.9 (5)N4—C23—H23A109.5
C2—C3—H3119.5N4—C23—H23B109.5
C4—C3—H3119.5H23A—C23—H23B109.5
C5—C4—C3120.0 (5)N4—C23—H23C109.5
C5—C4—H4120.0H23A—C23—H23C109.5
C3—C4—H4120.0H23B—C23—H23C109.5
C4—C5—C6120.9 (5)N4—C24—H24A109.5
C4—C5—H5119.5N4—C24—H24B109.5
C6—C5—H5119.5H24A—C24—H24B109.5
C1—C6—C5119.5 (4)N4—C24—H24C109.5
C1—C6—C8123.9 (4)H24A—C24—H24C109.5
C5—C6—C8116.6 (4)H24B—C24—H24C109.5
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5W—H5WB···N10i0.86 (6)2.69 (4)3.481 (8)155 (8)
O5W—H5WA···O10.86 (6)2.59 (6)3.129 (5)122 (6)
O5W—H5WA···O20.86 (6)1.86 (6)2.702 (4)167 (8)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5W—H5WB···N10i0.86 (6)2.69 (4)3.481 (8)155 (8)
O5W—H5WA···O10.86 (6)2.59 (6)3.129 (5)122 (6)
O5W—H5WA···O20.86 (6)1.86 (6)2.702 (4)167 (8)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

This project is supported by a research grant from the Dalian Medical University.

references
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