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Acta Cryst. (2008). E64, m760    [ doi:10.1107/S1600536808009495 ]

{2-[(5-Bromo-2-oxidobenzylidene)amino-[kappa]2N,O]-3-methylpentanoato-[kappa]O}(1,10-phenanthroline-[kappa]2N,N')copper(II) dihydrate

Z. Liu, Y.-L. Wang and Y. Wang

Abstract top

In the title compound, [Cu(C13H14BrNO3)(C12H8N2)]·2H2O, the CuII atom is pentacoordinated in a square-pyramidal geometry. The crystal packing is stabilized by O-H...O hydrogen bonds.

Comment top

Schiff base complexes play an important role in antibacterial and catalytic performance, and have attracted widespread interest by researchers (Jiang et al., 2003; Kettmann et al., 1993; Zhang, 2006). Meanwhile, Schiff base complexes containing isoleucine have been studied because they are of great significance in the biological and medical field (Royles et al., 2000; Feng et al., 2007; Li et al., 2006).

The central CuII atom is penta-coordinated (Fig.1). The quadratic planar is composed by O1, N2, O3and N1. The Schiff base forms two chelating rings(O1—C1—C2—N1—Cu1 and N1—C7—C8—C9—O3- Cu1) to the CuIIatom, with a diheral angle of 19.6 (4)° which is in the range observed for many copper Schiff base complexes. The N3 atom occupies the axial position with a N—Cu length of 2.229 (6) Å, comparing with the equatorial Cu—N bond lengths [Cu1—N1 1.924 (6)Å and N2—Cu1 1.975 (6)Å]. The crystal packing is stabilized by O—H···O hydrogen bonds (Fig. 2).

Related literature top

For related literature, see: Feng et al. (2007); Li et al. (2006); Royles & Sherrington (2000); Jiang et al. (2003); Kettmann et al. (1993); Zhang (2006); Zhang et al. (2003).

Experimental top

5-Bromo-2-hydroxy-benzaldehyde(0.5 mmol, 100.5 mg) was dissolved in hot ethanol(5 ml), then a mixture of D,L-isoleucine (0.5 mmol, 65.6 mg) and sodium hydroxide (1.0 mmol, 40 mg) was added. After stirring for 1 h, the copper dinitrate trihydrate(0.5 mmol, 120.8 mg) was added and refluxed for another 2 h. At last, an ethanol solution of Phen(0.5 mmol, 99.1 mg) was dropped gradually into to the reaction mixture and refluxed for further 3 h (Zhang et al., 2003; Zhang et al., 2006). The obtained green solution was filtered and held at room temperature for ten days, whereupon green crystals suitable for X-ray diffraction were obtained (yield: 45.2%, based on Cu).

Refinement top

All H atoms were positioned geometrically and were treated as riding atoms with C–H distances of 0.93 Å and Uiso(H) = 1.2 Ueq(C) and with O–H distances of 0.85 Å and Uiso(H) = 1.5 Ueq(O). The methyl groups were allowed to rotate but not to tip.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004) and SHELXTL (Sheldrick, 2008); 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. A view of the title compound, showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound.
{2-[(5-Bromo-2-oxidobenzylidene)amino-κ2N,O]-3-methylpentanoato-κO}(1,10- phenanthroline-κ2N,N')copper(II) top
Crystal data top
[Cu(C13H14BrNO3)(C12H8N2)]·2H2OF000 = 602
Mr = 591.94Dx = 1.550 Mg m−3
Monoclinic, P21Mo Kα radiation
λ = 0.71073 Å
a = 10.6184 (18) ÅCell parameters from 1263 reflections
b = 6.0520 (16) Åθ = 2.2–18.0º
c = 19.777 (3) ŵ = 2.48 mm−1
β = 93.481 (2)ºT = 298 (2) K
V = 1268.5 (4) Å3Block, green
Z = 20.65 × 0.10 × 0.07 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		4255 independent reflections
Radiation source: fine-focus sealed tube2269 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.053
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.9º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→10
Tmin = 0.296, Tmax = 0.846k = −7→7
6692 measured reflectionsl = −23→21
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.054  w = 1/[σ2(Fo2) + (0.0003P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.074(Δ/σ)max = 0.001
S = 0.96Δρmax = 0.52 e Å−3
4255 reflectionsΔρmin = −0.26 e Å−3
318 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 1785 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.054 (14)
Secondary atom site location: difference Fourier map
Crystal data top
[Cu(C13H14BrNO3)(C12H8N2)]·2H2OV = 1268.5 (4) Å3
Mr = 591.94Z = 2
Monoclinic, P21Mo Kα
a = 10.6184 (18) ŵ = 2.48 mm−1
b = 6.0520 (16) ÅT = 298 (2) K
c = 19.777 (3) Å0.65 × 0.10 × 0.07 mm
β = 93.481 (2)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		4255 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2269 reflections with I > 2σ(I)
Tmin = 0.296, Tmax = 0.846Rint = 0.053
6692 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.074Δρmax = 0.52 e Å−3
S = 0.96Δρmin = −0.26 e Å−3
4255 reflectionsAbsolute structure: Flack (1983), 1785 Friedel pairs
318 parametersFlack parameter: 0.054 (14)
1 restraint
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
Cu10.13990 (7)0.36558 (17)0.76571 (4)0.0503 (3)
Br1−0.25268 (7)0.10824 (17)0.46920 (4)0.0793 (3)
N10.2064 (5)0.1850 (11)0.6962 (3)0.0440 (18)
N20.0762 (6)0.5406 (11)0.8407 (3)0.052 (2)
N3−0.0327 (5)0.1749 (11)0.7873 (3)0.0451 (18)
O10.2695 (4)0.2179 (10)0.8245 (2)0.0594 (17)
O20.4200 (4)−0.0388 (10)0.8229 (2)0.077 (2)
O30.0499 (4)0.5429 (9)0.6982 (2)0.0540 (17)
O40.4374 (5)0.7917 (11)0.9519 (3)0.115 (3)
H260.51060.78400.97170.172*
H270.44800.78690.90970.172*
O50.3458 (5)0.3755 (14)0.9595 (3)0.124 (2)
H280.32130.32170.92130.186*
H290.36930.50680.95160.186*
C10.3385 (7)0.0792 (17)0.7944 (4)0.057 (2)
C20.3235 (5)0.0722 (14)0.7175 (3)0.050 (2)
H20.3166−0.08260.70320.060*
C30.4394 (6)0.1737 (12)0.6871 (3)0.056 (2)
H30.51360.10470.71010.067*
C40.4473 (6)0.4206 (12)0.7027 (4)0.068 (3)
H4A0.37660.49370.67870.082*
H4B0.43800.44100.75080.082*
C50.5670 (7)0.5334 (16)0.6844 (5)0.130 (5)
H5A0.63840.44730.70090.195*
H5B0.57150.67760.70460.195*
H5C0.56740.54710.63610.195*
C60.4453 (6)0.1239 (17)0.6124 (3)0.080 (3)
H6A0.38740.21800.58680.121*
H6B0.4229−0.02780.60410.121*
H6C0.52940.14980.59890.121*
C70.1408 (6)0.1318 (15)0.6429 (3)0.050 (2)
H70.16780.01300.61780.060*
C80.0288 (7)0.2422 (14)0.6194 (3)0.043 (2)
C9−0.0084 (7)0.4464 (14)0.6466 (4)0.043 (2)
C10−0.1150 (6)0.5530 (14)0.6133 (3)0.055 (3)
H10−0.13750.69350.62730.066*
C11−0.1843 (7)0.4556 (15)0.5618 (4)0.054 (2)
H11−0.25440.52800.54180.065*
C12−0.1509 (7)0.2463 (16)0.5385 (4)0.049 (3)
C13−0.0444 (6)0.1447 (15)0.5654 (3)0.049 (2)
H13−0.01990.00970.54800.059*
C140.1304 (8)0.7140 (15)0.8709 (4)0.065 (3)
H140.21110.75180.85920.078*
C150.0755 (11)0.843 (2)0.9188 (4)0.090 (3)
H150.11810.96470.93780.108*
C16−0.0422 (10)0.7901 (18)0.9377 (4)0.084 (4)
H16−0.08050.87440.97000.101*
C17−0.1043 (9)0.610 (2)0.9084 (4)0.069 (3)
C18−0.0414 (8)0.4876 (14)0.8610 (4)0.048 (2)
C19−0.1002 (7)0.2918 (15)0.8301 (4)0.050 (2)
C20−0.2215 (8)0.2353 (18)0.8491 (4)0.062 (3)
C21−0.2734 (8)0.042 (2)0.8195 (5)0.083 (4)
H21−0.3541−0.00350.82890.100*
C22−0.2037 (8)−0.0789 (18)0.7768 (4)0.082 (4)
H22−0.2362−0.20840.75730.098*
C23−0.0860 (8)−0.0077 (15)0.7629 (4)0.063 (3)
H23−0.0402−0.09410.73430.075*
C24−0.2293 (10)0.536 (2)0.9246 (5)0.090 (4)
H24−0.27250.61540.95620.108*
C25−0.2840 (9)0.359 (3)0.8958 (5)0.094 (4)
H25−0.36450.31820.90690.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0480 (5)0.0569 (7)0.0457 (6)−0.0033 (6)0.0014 (4)−0.0045 (6)
Br10.0785 (6)0.0890 (9)0.0672 (6)−0.0008 (6)−0.0220 (5)−0.0151 (7)
N10.034 (4)0.058 (5)0.040 (4)−0.009 (3)0.003 (3)0.012 (3)
N20.056 (5)0.051 (6)0.047 (4)−0.002 (4)−0.006 (3)−0.006 (4)
N30.053 (4)0.044 (5)0.038 (4)0.008 (4)0.003 (3)0.001 (3)
O10.053 (3)0.082 (5)0.044 (3)0.005 (3)0.004 (3)0.000 (3)
O20.058 (3)0.112 (6)0.061 (4)0.019 (3)0.002 (3)0.028 (4)
O30.062 (3)0.057 (5)0.041 (3)0.000 (3)−0.010 (2)−0.010 (3)
O40.124 (5)0.134 (8)0.083 (5)−0.028 (5)−0.019 (4)0.026 (5)
O50.188 (6)0.110 (6)0.070 (4)−0.040 (6)−0.032 (4)0.021 (5)
C10.050 (6)0.064 (7)0.056 (6)−0.006 (5)−0.001 (4)0.013 (6)
C20.038 (4)0.050 (6)0.061 (5)−0.006 (4)−0.005 (4)0.005 (5)
C30.052 (5)0.063 (8)0.053 (5)0.011 (5)0.007 (4)0.001 (5)
C40.053 (5)0.064 (9)0.088 (7)−0.019 (5)0.004 (4)0.011 (6)
C50.089 (7)0.105 (12)0.195 (12)−0.034 (8)0.005 (7)0.011 (9)
C60.077 (5)0.101 (9)0.064 (6)−0.001 (7)0.003 (4)−0.004 (7)
C70.050 (5)0.056 (6)0.046 (5)0.000 (5)0.006 (4)−0.005 (5)
C80.046 (5)0.055 (7)0.027 (5)0.000 (4)0.005 (4)0.000 (4)
C90.052 (5)0.045 (7)0.033 (5)0.006 (4)0.008 (4)−0.002 (4)
C100.076 (6)0.047 (7)0.042 (5)0.016 (5)0.000 (4)−0.009 (5)
C110.063 (6)0.049 (7)0.047 (6)0.018 (5)−0.009 (4)0.000 (5)
C120.044 (5)0.069 (8)0.035 (5)0.000 (5)0.001 (4)0.004 (5)
C130.065 (5)0.043 (6)0.040 (5)0.001 (5)0.008 (4)−0.003 (5)
C140.084 (7)0.051 (7)0.057 (6)−0.004 (6)−0.011 (5)0.006 (5)
C150.177 (10)0.058 (7)0.033 (5)0.006 (10)−0.008 (6)−0.009 (6)
C160.132 (9)0.074 (10)0.046 (6)0.041 (8)0.014 (6)−0.004 (6)
C170.095 (7)0.079 (8)0.032 (5)0.018 (8)0.000 (5)−0.005 (6)
C180.059 (6)0.056 (6)0.030 (5)0.014 (5)−0.002 (4)0.002 (4)
C190.047 (5)0.062 (8)0.040 (5)−0.004 (5)−0.004 (4)0.017 (5)
C200.052 (6)0.079 (8)0.055 (7)−0.003 (6)0.001 (5)0.014 (6)
C210.048 (6)0.120 (13)0.081 (8)−0.009 (7)−0.010 (5)0.041 (8)
C220.060 (6)0.105 (11)0.076 (7)−0.040 (7)−0.030 (5)0.024 (7)
C230.073 (7)0.046 (7)0.067 (6)−0.015 (5)−0.018 (5)−0.007 (5)
C240.089 (9)0.131 (14)0.052 (7)0.048 (8)0.030 (6)0.027 (7)
C250.070 (7)0.143 (12)0.072 (8)0.027 (10)0.020 (6)0.026 (9)
Geometric parameters (Å, °) top
Cu1—O31.922 (5)C6—H6C0.9600
Cu1—N11.924 (6)C7—C81.417 (9)
Cu1—O11.963 (5)C7—H70.9300
Cu1—N21.975 (6)C8—C131.411 (9)
Cu1—N32.229 (6)C8—C91.413 (9)
Br1—C121.888 (8)C9—C101.429 (9)
N1—C71.269 (7)C10—C111.355 (9)
N1—C21.458 (7)C10—H100.9300
N2—C141.322 (9)C11—C121.401 (10)
N2—C181.373 (8)C11—H110.9300
N3—C231.320 (9)C12—C131.367 (9)
N3—C191.343 (9)C13—H130.9300
O1—C11.284 (9)C14—C151.385 (11)
O2—C11.232 (8)C14—H140.9300
O3—C91.300 (8)C15—C161.365 (11)
O4—H260.8500C15—H150.9300
O4—H270.8500C16—C171.384 (13)
O5—H280.8501C16—H160.9300
O5—H290.8500C17—C181.396 (11)
C1—C21.520 (6)C17—C241.454 (12)
C2—C31.531 (6)C18—C191.456 (10)
C2—H20.9800C19—C201.405 (10)
C3—C61.512 (6)C20—C251.389 (12)
C3—C41.528 (6)C20—C211.406 (12)
C3—H30.9800C21—C221.368 (11)
C4—C51.506 (6)C21—H210.9300
C4—H4A0.9700C22—C231.365 (9)
C4—H4B0.9700C22—H220.9300
C5—H5A0.9600C23—H230.9300
C5—H5B0.9600C24—C251.330 (14)
C5—H5C0.9600C24—H240.9300
C6—H6A0.9600C25—H250.9300
C6—H6B0.9600
O3—Cu1—N190.5 (2)N1—C7—H7118.0
O3—Cu1—O1165.3 (2)C8—C7—H7118.0
N1—Cu1—O183.7 (2)C13—C8—C9120.0 (7)
O3—Cu1—N292.5 (2)C13—C8—C7117.6 (8)
N1—Cu1—N2177.0 (3)C9—C8—C7122.4 (7)
O1—Cu1—N293.4 (2)O3—C9—C8124.1 (7)
O3—Cu1—N392.42 (19)O3—C9—C10119.0 (8)
N1—Cu1—N3100.6 (2)C8—C9—C10116.9 (7)
O1—Cu1—N3101.9 (2)C11—C10—C9121.9 (8)
N2—Cu1—N379.1 (3)C11—C10—H10119.0
C7—N1—C2122.5 (7)C9—C10—H10119.0
C7—N1—Cu1122.0 (5)C10—C11—C12120.2 (8)
C2—N1—Cu1113.8 (4)C10—C11—H11119.9
C14—N2—C18115.6 (7)C12—C11—H11119.9
C14—N2—Cu1127.3 (7)C13—C12—C11120.0 (8)
C18—N2—Cu1116.9 (6)C13—C12—Br1120.5 (7)
C23—N3—C19115.9 (7)C11—C12—Br1119.5 (7)
C23—N3—Cu1134.7 (6)C12—C13—C8120.8 (8)
C19—N3—Cu1109.0 (5)C12—C13—H13119.6
C1—O1—Cu1115.0 (5)C8—C13—H13119.6
C9—O3—Cu1119.2 (5)N2—C14—C15124.6 (9)
H26—O4—H27106.2N2—C14—H14117.7
H28—O5—H29105.7C15—C14—H14117.7
O2—C1—O1124.8 (7)C16—C15—C14119.0 (11)
O2—C1—C2118.0 (8)C16—C15—H15120.5
O1—C1—C2117.0 (7)C14—C15—H15120.5
N1—C2—C1108.2 (6)C15—C16—C17119.6 (10)
N1—C2—C3112.9 (6)C15—C16—H16120.2
C1—C2—C3110.1 (6)C17—C16—H16120.2
N1—C2—H2108.5C16—C17—C18117.6 (10)
C1—C2—H2108.5C16—C17—C24124.6 (11)
C3—C2—H2108.5C18—C17—C24117.8 (11)
C6—C3—C4112.8 (7)N2—C18—C17123.7 (9)
C6—C3—C2112.7 (6)N2—C18—C19116.3 (8)
C4—C3—C2110.4 (6)C17—C18—C19120.1 (9)
C6—C3—H3106.8N3—C19—C20125.0 (9)
C4—C3—H3106.8N3—C19—C18117.4 (7)
C2—C3—H3106.8C20—C19—C18117.6 (9)
C5—C4—C3115.6 (7)C25—C20—C19121.9 (10)
C5—C4—H4A108.4C25—C20—C21122.3 (11)
C3—C4—H4A108.4C19—C20—C21115.7 (9)
C5—C4—H4B108.4C22—C21—C20119.2 (10)
C3—C4—H4B108.4C22—C21—H21120.4
H4A—C4—H4B107.4C20—C21—H21120.4
C4—C5—H5A109.5C23—C22—C21119.4 (10)
C4—C5—H5B109.5C23—C22—H22120.3
H5A—C5—H5B109.5C21—C22—H22120.3
C4—C5—H5C109.5N3—C23—C22124.7 (9)
H5A—C5—H5C109.5N3—C23—H23117.7
H5B—C5—H5C109.5C22—C23—H23117.7
C3—C6—H6A109.5C25—C24—C17122.2 (11)
C3—C6—H6B109.5C25—C24—H24118.9
H6A—C6—H6B109.5C17—C24—H24118.9
C3—C6—H6C109.5C24—C25—C20120.4 (11)
H6A—C6—H6C109.5C24—C25—H25119.8
H6B—C6—H6C109.5C20—C25—H25119.8
N1—C7—C8124.1 (8)
O3—Cu1—N1—C7−38.3 (6)Cu1—O3—C9—C8−28.3 (9)
O1—Cu1—N1—C7155.2 (6)Cu1—O3—C9—C10153.4 (5)
N2—Cu1—N1—C7139 (5)C13—C8—C9—O3176.7 (7)
N3—Cu1—N1—C754.2 (7)C7—C8—C9—O3−5.4 (11)
O3—Cu1—N1—C2156.3 (5)C13—C8—C9—C10−5.0 (10)
O1—Cu1—N1—C2−10.2 (5)C7—C8—C9—C10172.9 (7)
N2—Cu1—N1—C2−26 (5)O3—C9—C10—C11−176.1 (7)
N3—Cu1—N1—C2−111.1 (5)C8—C9—C10—C115.6 (11)
O3—Cu1—N2—C14−92.1 (6)C9—C10—C11—C12−1.4 (12)
N1—Cu1—N2—C1491 (5)C10—C11—C12—C13−3.4 (11)
O1—Cu1—N2—C1474.5 (6)C10—C11—C12—Br1177.4 (6)
N3—Cu1—N2—C14175.9 (6)C11—C12—C13—C83.8 (11)
O3—Cu1—N2—C1883.0 (5)Br1—C12—C13—C8−177.0 (5)
N1—Cu1—N2—C18−94 (5)C9—C8—C13—C120.5 (10)
O1—Cu1—N2—C18−110.5 (5)C7—C8—C13—C12−177.5 (6)
N3—Cu1—N2—C18−9.0 (5)C18—N2—C14—C15−1.7 (11)
O3—Cu1—N3—C2390.0 (7)Cu1—N2—C14—C15173.4 (7)
N1—Cu1—N3—C23−1.0 (7)N2—C14—C15—C160.9 (14)
O1—Cu1—N3—C23−86.7 (7)C14—C15—C16—C17−0.4 (14)
N2—Cu1—N3—C23−177.9 (7)C15—C16—C17—C180.9 (14)
O3—Cu1—N3—C19−82.0 (5)C15—C16—C17—C24179.7 (9)
N1—Cu1—N3—C19−173.0 (5)C14—N2—C18—C172.3 (11)
O1—Cu1—N3—C19101.3 (5)Cu1—N2—C18—C17−173.4 (6)
N2—Cu1—N3—C1910.1 (5)C14—N2—C18—C19−177.6 (6)
O3—Cu1—O1—C1−66.4 (12)Cu1—N2—C18—C196.7 (8)
N1—Cu1—O1—C11.0 (6)C16—C17—C18—N2−1.9 (13)
N2—Cu1—O1—C1−179.9 (6)C24—C17—C18—N2179.3 (8)
N3—Cu1—O1—C1100.6 (6)C16—C17—C18—C19178.0 (7)
N1—Cu1—O3—C942.5 (5)C24—C17—C18—C19−0.8 (12)
O1—Cu1—O3—C9109.1 (10)C23—N3—C19—C20−1.1 (11)
N2—Cu1—O3—C9−137.3 (5)Cu1—N3—C19—C20172.5 (6)
N3—Cu1—O3—C9−58.1 (5)C23—N3—C19—C18176.6 (6)
Cu1—O1—C1—O2−175.7 (7)Cu1—N3—C19—C18−9.7 (7)
Cu1—O1—C1—C28.3 (9)N2—C18—C19—N33.1 (9)
C7—N1—C2—C1−149.3 (7)C17—C18—C19—N3−176.8 (7)
Cu1—N1—C2—C116.0 (7)N2—C18—C19—C20−179.0 (7)
C7—N1—C2—C388.5 (8)C17—C18—C19—C201.1 (11)
Cu1—N1—C2—C3−106.2 (5)N3—C19—C20—C25177.4 (8)
O2—C1—C2—N1167.9 (7)C18—C19—C20—C25−0.3 (12)
O1—C1—C2—N1−15.8 (10)N3—C19—C20—C21−0.6 (11)
O2—C1—C2—C3−68.2 (10)C18—C19—C20—C21−178.3 (7)
O1—C1—C2—C3108.0 (8)C25—C20—C21—C22−176.4 (9)
N1—C2—C3—C6−72.6 (8)C19—C20—C21—C221.6 (12)
C1—C2—C3—C6166.3 (8)C20—C21—C22—C23−0.9 (14)
N1—C2—C3—C454.6 (8)C19—N3—C23—C222.0 (11)
C1—C2—C3—C4−66.5 (9)Cu1—N3—C23—C22−169.6 (6)
C6—C3—C4—C5−61.5 (9)C21—C22—C23—N3−1.0 (13)
C2—C3—C4—C5171.4 (6)C16—C17—C24—C25−178.9 (11)
C2—N1—C7—C8−177.8 (6)C18—C17—C24—C25−0.1 (15)
Cu1—N1—C7—C818.1 (10)C17—C24—C25—C200.9 (18)
N1—C7—C8—C13−170.6 (7)C19—C20—C25—C24−0.6 (17)
N1—C7—C8—C911.5 (11)C21—C20—C25—C24177.2 (10)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H28···O10.852.062.904 (8)174
O5—H29···O40.851.872.708 (10)168
O4—H26···O5i0.852.062.853 (8)156
O4—H27···O2ii0.852.022.746 (7)143
Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) x, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H28···O10.852.062.904 (8)174
O5—H29···O40.851.872.708 (10)168
O4—H26···O5i0.852.062.853 (8)156
O4—H27···O2ii0.852.022.746 (7)143
Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) x, y+1, z.
Acknowledgements top

We acknowledge financial support by the Key Laboratory of Non-ferrous Metal Materials and New Processing Technology, Ministry of Education, China.

references
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