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Acta Cryst. (2008). E64, m373    [ doi:10.1107/S1600536808001438 ]

Tris(ethane-1,2-diamine)copper(II) bis(trifluoroacetate)

E. V. Karpova, M. A. Zakharov, A. I. Boltalin and V. B. Rybakov

Abstract top

In the title complex, [Cu(H2NCH2CH2NH2)3](CF3COO)2, the environment of the Cu atom is distorted octahedral, formed by six N atoms from three chelating ethane-1,2-diamine ligands. The Cu-N distances range from 2.050 (2) to 2.300 (2) Å. This complex cation and the two trifluoroacetate anions are connected by weak N-H...O and N-H...F hydrogen bonds, forming a three-dimensional framework. In both anions, the F atoms are disordered over two positions; in one the site-occupancy factors are 0.55 and 0.45, in the other the values are 0.69 and 0.31.

Comment top

The present investigation is a continuation of experimental work to study the structure and properties of different carboxylate complexes (Karpova et al., 1998; Karpova et al., 2001; Gutnikov et al., 2006; Karpova et al., 2007). In the title compound, Cu(H2NCH2CH2NH2)3.(CF3COO)2, the asymmetric unit consists of a complex cation and two crystallographically independent anions. The environment of the Cu atom is distorted octahedral, formed by six N atoms from three chelate ethylenediamine groups. The two trifluoroacetate anions form N—H···O and N—H···F hydrogen bonds with NH2 groups of the cation, forming a three-dimensional framework.

Related literature top

For other carboxylate complexes, see: Karpova et al. (1998); Karpova et al. (2001); Gutnikov et al. (2006); Karpova et al. (2007).

Experimental top

An ethanol solution of [Cu(CF3COO)2(CH3CN)]2(CH3CN)2 was mixed with ethylenediamine in a 1:4 molar ratio. After several days blue prism-shaped crystals were formed in a desiccator over P4O10.

Refinement top

All H atoms were positioned geometrically and refined using a riding model (including free rotation about C—C or C—N bonds) with C—H = 0.97 Å, N—H = 0.90 Å and with Uiso(H) = 1.2Ueq(C,N). The DELU option in SHELXL97 was used with parameters 0.0001, 0.0001 for all bonds Cu1—N; for all C—O and C—F bonds. The MERG option with parameter 2 was used before refinement. The F atoms are disordered over two positions, with site occupancy ratios 0.55 (3)/0.45 (3) and 0.69 (2)/0.31 (2).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A view of the title compound, with the atom numbering scheme. Displacment ellipsoids are shown at the 50% probability level. H atoms are drawn as small spheres of arbitrary radius. Only the major disorder components are shown.
Tris(ethane-1,2-diamine)copper(II) bis(trifluoroacetate) top
Crystal data top
[Cu(C2H8N2)3](C2F3O2)2Z = 2
Mr = 469.90F000 = 482
Triclinic, P1Dx = 1.679 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 8.582 (6) ÅCell parameters from 250 reflections
b = 9.316 (6) Åθ = 18–24º
c = 12.859 (7) ŵ = 1.26 mm−1
α = 74.73 (3)ºT = 293 (2) K
β = 84.69 (4)ºPrism, blue
γ = 69.56 (3)º0.15 × 0.1 × 0.08 mm
V = 929.3 (10) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer		5406 independent reflections
Radiation source: fine–focus sealed tube4277 reflections with I > 2σ(I)
Monochromator: graphiteθmax = 30.0º
Detector resolution: 0.1 pixels mm-1θmin = 1.6º
T = 293(2) Kh = −11→12
φ and ω scansk = 0→13
Absorption correction: nonel = −17→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)] = 0.039H-atom parameters constrained
wR(F2) = 0.092  w = 1/[σ2(Fo2) + (0.0567P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max = 0.001
5406 reflectionsΔρmax = 0.24 e Å−3
300 parametersΔρmin = −0.24 e Å−3
45 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Cu(C2H8N2)3](C2F3O2)2γ = 69.56 (3)º
Mr = 469.90V = 929.3 (10) Å3
Triclinic, P1Z = 2
a = 8.582 (6) ÅMo Kα
b = 9.316 (6) ŵ = 1.26 mm−1
c = 12.859 (7) ÅT = 293 (2) K
α = 74.73 (3)º0.15 × 0.1 × 0.08 mm
β = 84.69 (4)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		5406 independent reflections
Absorption correction: none4277 reflections with I > 2σ(I)
? measured reflectionsRint = ?
Refinement top
R[F2 > 2σ(F2)] = 0.03945 restraints
wR(F2) = 0.092H-atom parameters constrained
S = 0.94Δρmax = 0.24 e Å−3
5406 reflectionsΔρmin = −0.24 e Å−3
300 parameters
Special details top

Experimental. The original HKL file was deleted and the present study was conducted using the merged data set.

Geometry. All s.u.'s (except the s.u.'s in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)
Cu10.94303 (3)0.85236 (3)0.778785 (18)0.03254 (8)
N10.8821 (2)0.8734 (2)0.93404 (13)0.0444 (3)
H1A0.96940.81310.97770.053*
H1B0.85870.97450.93620.053*
C10.7376 (3)0.8237 (3)0.97256 (17)0.0486 (5)
H1C0.69210.86101.03630.058*
H1D0.77260.70920.99230.058*
C20.6060 (3)0.8885 (3)0.88718 (19)0.0503 (5)
H2C0.51390.85050.91210.060*
H2D0.56411.00310.87080.060*
N20.6812 (2)0.8352 (2)0.79038 (16)0.0495 (4)
H2A0.62120.89770.73140.059*
H2B0.68660.73500.79680.059*
N30.8604 (2)1.1007 (2)0.71134 (15)0.0471 (4)
H3A0.80041.12440.65150.057*
H3B0.79481.15050.75890.057*
C31.0036 (3)1.1543 (3)0.68450 (19)0.0539 (5)
H3C0.96721.26810.67390.065*
H3D1.05311.12920.61770.065*
C41.1308 (3)1.0764 (3)0.77268 (19)0.0510 (5)
H4C1.22661.11020.75230.061*
H4D1.08431.10790.83820.061*
N41.1826 (2)0.9040 (2)0.79228 (15)0.0457 (4)
H4A1.22770.85640.85830.055*
H4B1.25770.86950.74280.055*
N50.9835 (2)0.8096 (2)0.62842 (13)0.0453 (4)
H5A0.89230.86580.58730.054*
H5B1.06880.83960.59650.054*
C51.0217 (3)0.6405 (3)0.6384 (2)0.0540 (5)
H5C1.07120.61340.57210.065*
H5D0.92080.61390.65220.065*
C61.1414 (3)0.5510 (3)0.7304 (2)0.0541 (5)
H6C1.16490.43820.74200.065*
H6D1.24510.57210.71440.065*
N61.0652 (2)0.6024 (2)0.82682 (15)0.0482 (4)
H6A1.14350.57830.87660.058*
H6B0.99140.55390.85550.058*
C70.7420 (3)0.3504 (3)0.91576 (18)0.0494 (4)
C80.5826 (4)0.4304 (4)0.8472 (3)0.0722 (6)
C90.5876 (3)0.1740 (3)0.4611 (2)0.0526 (5)
C100.4415 (4)0.2533 (4)0.5269 (3)0.0749 (6)
O10.8137 (3)0.4407 (2)0.92515 (17)0.0722 (5)
O20.7776 (3)0.2083 (2)0.95315 (17)0.0721 (5)
O30.7270 (2)0.1248 (2)0.50104 (16)0.0693 (5)
O40.5502 (3)0.1706 (3)0.37227 (17)0.0780 (6)
F1A0.495 (2)0.5750 (14)0.8639 (12)0.087 (2)0.55 (3)
F2A0.4769 (16)0.3531 (13)0.8668 (13)0.089 (3)0.55 (3)
F3A0.6064 (18)0.4591 (14)0.7404 (6)0.093 (3)0.55 (3)
F1B0.471 (2)0.537 (2)0.8865 (14)0.083 (2)0.45 (3)
F2B0.5182 (17)0.3267 (11)0.8290 (14)0.088 (2)0.45 (3)
F3B0.6454 (13)0.4960 (16)0.7584 (10)0.084 (3)0.45 (3)
F4A0.4601 (19)0.166 (3)0.6294 (12)0.095 (4)0.31 (2)
F5A0.2886 (15)0.281 (3)0.4998 (12)0.090 (4)0.31 (2)
F6A0.460 (3)0.3837 (19)0.529 (2)0.110 (5)0.31 (2)
F4B0.4729 (10)0.2254 (9)0.6304 (5)0.0850 (12)0.69 (2)
F5B0.3116 (8)0.2068 (10)0.5228 (6)0.0872 (13)0.69 (2)
F6B0.3834 (11)0.4109 (4)0.4916 (4)0.0858 (16)0.69 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03390 (11)0.03383 (12)0.03075 (11)−0.01198 (8)−0.00040 (7)−0.00858 (8)
N10.0453 (9)0.0514 (10)0.0380 (6)−0.0172 (8)0.0030 (6)−0.0134 (6)
C10.0495 (12)0.0522 (12)0.0418 (11)−0.0159 (10)0.0017 (9)−0.0102 (9)
C20.0459 (11)0.0535 (12)0.0534 (12)−0.0178 (10)−0.0004 (9)−0.0151 (10)
N20.0431 (7)0.0582 (10)0.0527 (10)−0.0214 (8)0.0005 (7)−0.0173 (9)
N30.0516 (9)0.0419 (7)0.0458 (9)−0.0141 (6)−0.0022 (7)−0.0090 (6)
C30.0558 (13)0.0551 (13)0.0501 (12)−0.0207 (11)−0.0030 (10)−0.0082 (10)
C40.0567 (13)0.0513 (12)0.0484 (12)−0.0217 (10)−0.0007 (10)−0.0126 (10)
N40.0435 (7)0.0539 (10)0.0436 (9)−0.0214 (7)0.0008 (6)−0.0122 (8)
N50.0497 (9)0.0504 (9)0.0371 (7)−0.0169 (8)−0.0005 (6)−0.0130 (7)
C50.0562 (13)0.0536 (13)0.0544 (13)−0.0187 (10)−0.0003 (10)−0.0168 (11)
C60.0556 (13)0.0511 (12)0.0564 (13)−0.0160 (10)0.0011 (10)−0.0178 (11)
N60.0492 (10)0.0468 (10)0.0468 (10)−0.0151 (8)−0.0046 (8)−0.0085 (8)
C70.0437 (11)0.0599 (10)0.0441 (11)−0.0142 (9)0.0010 (8)−0.0166 (9)
C80.0540 (14)0.0761 (15)0.0748 (13)−0.0134 (9)−0.0125 (11)−0.0069 (13)
C90.0515 (10)0.0506 (12)0.0544 (11)−0.0160 (10)0.0046 (9)−0.0141 (10)
C100.0646 (14)0.0808 (12)0.0766 (12)−0.0185 (13)0.0130 (13)−0.0279 (14)
O10.0695 (12)0.0765 (11)0.0789 (13)−0.0323 (10)−0.0057 (10)−0.0208 (10)
O20.0746 (12)0.0622 (9)0.0781 (13)−0.0197 (9)−0.0112 (10)−0.0157 (9)
O30.0593 (10)0.0788 (13)0.0688 (11)−0.0210 (9)−0.0023 (8)−0.0191 (10)
O40.0763 (13)0.0897 (15)0.0685 (11)−0.0219 (11)−0.0079 (9)−0.0262 (11)
F1A0.094 (5)0.078 (3)0.086 (5)−0.026 (2)−0.003 (3)−0.018 (4)
F2A0.085 (4)0.089 (3)0.097 (5)−0.036 (3)−0.012 (3)−0.018 (3)
F3A0.099 (5)0.099 (4)0.0789 (16)−0.032 (3)−0.003 (2)−0.0216 (19)
F1B0.077 (4)0.089 (6)0.085 (6)−0.026 (4)0.004 (3)−0.025 (5)
F2B0.086 (5)0.093 (3)0.089 (6)−0.033 (3)0.006 (4)−0.029 (3)
F3B0.078 (4)0.102 (5)0.075 (3)−0.033 (3)0.001 (2)−0.022 (3)
F4A0.070 (4)0.113 (10)0.093 (4)−0.038 (6)0.005 (3)0.000 (6)
F5A0.078 (3)0.116 (11)0.083 (5)−0.038 (6)0.005 (3)−0.029 (6)
F6A0.097 (9)0.098 (5)0.144 (12)−0.056 (6)0.016 (8)−0.020 (7)
F4B0.085 (3)0.091 (3)0.0800 (15)−0.033 (2)0.0010 (16)−0.0179 (17)
F5B0.080 (2)0.091 (3)0.090 (3)−0.030 (3)−0.0023 (18)−0.020 (3)
F6B0.082 (4)0.0829 (12)0.090 (2)−0.0239 (16)−0.0062 (19)−0.0192 (13)
Geometric parameters (Å, °) top
Cu1—N52.050 (2)N5—H5A0.9000
Cu1—N12.059 (2)N5—H5B0.9000
Cu1—N32.126 (2)C5—C61.503 (3)
Cu1—N62.136 (2)C5—H5C0.9700
Cu1—N22.297 (2)C5—H5D0.9700
Cu1—N42.300 (2)C6—N61.462 (3)
N1—C11.471 (3)C6—H6C0.9700
N1—H1A0.9000C6—H6D0.9700
N1—H1B0.9000N6—H6A0.9000
C1—C21.500 (3)N6—H6B0.9000
C1—H1C0.9700C7—O21.219 (3)
C1—H1D0.9700C7—O11.237 (3)
C2—N21.471 (3)C7—C81.539 (4)
C2—H2C0.9700C8—F1B1.291 (11)
C2—H2D0.9700C8—F3B1.311 (7)
N2—H2A0.9000C8—F2A1.312 (7)
N2—H2B0.9000C8—F3A1.338 (7)
N3—C31.462 (3)C8—F2B1.345 (9)
N3—H3A0.9000C8—F1A1.357 (9)
N3—H3B0.9000C9—O41.225 (3)
C3—C41.499 (3)C9—O31.230 (3)
C3—H3C0.9700C9—C101.524 (4)
C3—H3D0.9700C10—F6A1.286 (10)
C4—N41.466 (3)C10—F5A1.308 (11)
C4—H4C0.9700C10—F4B1.322 (6)
C4—H4D0.9700C10—F5B1.338 (5)
N4—H4A0.9000C10—F6B1.338 (5)
N4—H4B0.9000C10—F4A1.343 (11)
N5—C51.464 (3)
N5—Cu1—N1171.52 (7)H5A—N5—H5B108.3
N5—Cu1—N391.32 (8)N5—C5—C6107.7 (2)
N1—Cu1—N393.88 (8)N5—C5—H5C110.2
N5—Cu1—N681.82 (8)C6—C5—H5C110.2
N1—Cu1—N693.95 (8)N5—C5—H5D110.2
N3—Cu1—N6169.22 (7)C6—C5—H5D110.2
N5—Cu1—N292.91 (8)H5C—C5—H5D108.5
N1—Cu1—N280.03 (8)N6—C6—C5108.1 (2)
N3—Cu1—N294.49 (8)N6—C6—H6C110.1
N6—Cu1—N294.15 (9)C5—C6—H6C110.1
N5—Cu1—N498.13 (8)N6—C6—H6D110.1
N1—Cu1—N489.38 (8)C5—C6—H6D110.1
N3—Cu1—N479.81 (8)H6C—C6—H6D108.4
N6—Cu1—N492.88 (8)C6—N6—Cu1107.29 (14)
N2—Cu1—N4167.65 (7)C6—N6—H6A110.3
C1—N1—Cu1110.81 (14)Cu1—N6—H6A110.3
C1—N1—H1A109.5C6—N6—H6B110.3
Cu1—N1—H1A109.5Cu1—N6—H6B110.3
C1—N1—H1B109.5H6A—N6—H6B108.5
Cu1—N1—H1B109.5O2—C7—O1129.9 (2)
H1A—N1—H1B108.1O2—C7—C8115.2 (2)
N1—C1—C2110.86 (18)O1—C7—C8114.9 (2)
N1—C1—H1C109.5F1B—C8—F3B110.6 (7)
C2—C1—H1C109.5F1B—C8—F2A86.2 (6)
N1—C1—H1D109.5F3B—C8—F2A133.3 (5)
C2—C1—H1D109.5F1B—C8—F3A118.9 (10)
H1C—C1—H1D108.1F3B—C8—F3A28.3 (3)
N2—C2—C1107.94 (19)F2A—C8—F3A105.2 (5)
N2—C2—H2C110.1F1B—C8—F2B110.6 (7)
C1—C2—H2C110.1F3B—C8—F2B110.6 (5)
N2—C2—H2D110.1F2A—C8—F2B27.2 (3)
C1—C2—H2D110.1F3A—C8—F2B82.7 (5)
H2C—C2—H2D108.4F1B—C8—F1A21.0 (6)
C2—N2—Cu1105.49 (14)F3B—C8—F1A90.5 (6)
C2—N2—H2A110.6F2A—C8—F1A104.9 (5)
Cu1—N2—H2A110.6F3A—C8—F1A103.9 (6)
C2—N2—H2B110.6F2B—C8—F1A126.1 (7)
Cu1—N2—H2B110.6F1B—C8—C7112.6 (9)
H2A—N2—H2B108.8F3B—C8—C798.8 (7)
C3—N3—Cu1109.77 (15)F2A—C8—C7114.9 (4)
C3—N3—H3A109.7F3A—C8—C7115.3 (7)
Cu1—N3—H3A109.7F2B—C8—C7113.1 (5)
C3—N3—H3B109.7F1A—C8—C7111.6 (7)
Cu1—N3—H3B109.7O4—C9—O3128.0 (3)
H3A—N3—H3B108.2O4—C9—C10114.6 (3)
N3—C3—C4110.8 (2)O3—C9—C10117.4 (3)
N3—C3—H3C109.5F6A—C10—F5A109.5 (6)
C4—C3—H3C109.5F6A—C10—F4B79.6 (10)
N3—C3—H3D109.5F5A—C10—F4B117.5 (7)
C4—C3—H3D109.5F6A—C10—F5B135.3 (9)
H3C—C3—H3D108.1F5A—C10—F5B28.1 (8)
N4—C4—C3110.08 (19)F4B—C10—F5B105.9 (4)
N4—C4—H4C109.6F6A—C10—F6B34.5 (11)
C3—C4—H4C109.6F5A—C10—F6B77.3 (8)
N4—C4—H4D109.6F4B—C10—F6B105.2 (4)
C3—C4—H4D109.6F5B—C10—F6B105.2 (3)
H4C—C4—H4D108.2F6A—C10—F4A105.5 (7)
C4—N4—Cu1105.13 (14)F5A—C10—F4A106.4 (8)
C4—N4—H4A110.7F4B—C10—F4A26.0 (9)
Cu1—N4—H4A110.7F5B—C10—F4A86.2 (7)
C4—N4—H4B110.7F6B—C10—F4A128.0 (12)
Cu1—N4—H4B110.7F6A—C10—C9105.3 (6)
H4A—N4—H4B108.8F5A—C10—C9120.7 (7)
C5—N5—Cu1109.29 (14)F4B—C10—C9114.9 (4)
C5—N5—H5A109.8F5B—C10—C9111.5 (4)
Cu1—N5—H5A109.8F6B—C10—C9113.3 (3)
C5—N5—H5B109.8F4A—C10—C9108.5 (9)
Cu1—N5—H5B109.8
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···F1A0.902.543.248 (17)136
N2—H2B···F3B0.902.553.41 (2)161
N6—H6B···O10.902.153.048 (3)179
N1—H1A···O2i0.902.353.141 (3)147
N1—H1A···O1i0.902.533.377 (4)156
N4—H4A···O2i0.902.343.175 (3)154
N6—H6A···O1i0.902.563.326 (3)143
N1—H1B···O2ii0.902.113.002 (3)173
N2—H2A···F4Aii0.902.473.267 (15)148
N3—H3A···O3ii0.902.092.958 (3)162
N5—H5A···O3ii0.902.363.126 (3)143
N2—H2A···O4iii0.902.413.037 (3)127
N4—H4B···O4iv0.902.112.997 (3)168
N5—H5B···O3iv0.902.133.013 (3)167
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x, y+1, z; (iii) −x+1, −y+1, −z+1; (iv) −x+2, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···F1A0.902.543.248 (17)136
N2—H2B···F3B0.902.553.41 (2)161
N6—H6B···O10.902.153.048 (3)179
N1—H1A···O2i0.902.353.141 (3)147
N1—H1A···O1i0.902.533.377 (4)156
N4—H4A···O2i0.902.343.175 (3)154
N6—H6A···O1i0.902.563.326 (3)143
N1—H1B···O2ii0.902.113.002 (3)173
N2—H2A···F4Aii0.902.473.267 (15)148
N3—H3A···O3ii0.902.092.958 (3)162
N5—H5A···O3ii0.902.363.126 (3)143
N2—H2A···O4iii0.902.413.037 (3)127
N4—H4B···O4iv0.902.112.997 (3)168
N5—H5B···O3iv0.902.133.013 (3)167
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x, y+1, z; (iii) −x+1, −y+1, −z+1; (iv) −x+2, −y+1, −z+1.
Acknowledgements top

The authors gratefully acknowledge Zoja A. Starikova for the X-ray data collection. This investigation was supported by the Russian Fund of Basic Research, project No 05–03–33038–a.

references
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