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

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

doi:10.1107/S1600536808001438

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m373

doi:10.1107/S1600536808001438

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

Elena V. Karpova,^a Maxim A. Zakharov,^b Alexandr I. Boltalin ^a and Victor B. Rybakov ^b ^*

^aInorganic Chemistry Division, Chemistry Department, Moscow State University, 119991 Leninskie Gory 1-3, Moscow, Russian Federation, and ^bGeneral Chemistry Division, Chemistry Department, Moscow State University, 119991 Leninskie Gory 1-3, Moscow, Russian Federation
^*Correspondence e-mail: rybakov20021@yandex.ru

(Received 18 December 2007; accepted 14 January 2008; online 18 January 2008)

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.

Related literature

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

Experimental

Crystal data

[Cu(C₂H₈N₂)₃](C₂F₃O₂)₂
M_r = 469.90
Triclinic, $[P \overline 1]$
a = 8.582 (6) Å
b = 9.316 (6) Å
c = 12.859 (7) Å
α = 74.73 (3)°
β = 84.69 (4)°
γ = 69.56 (3)°
V = 929.3 (10) Å³
Z = 2
Mo Kα radiation
μ = 1.26 mm⁻¹
T = 293 (2) K
0.15 × 0.1 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
5406 independent reflections
4277 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.092
S = 0.94
5406 reflections
300 parameters
45 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯F1A	0.90	2.54	3.248 (17)	136
N2—H2B⋯F3B	0.90	2.55	3.41 (2)	161
N6—H6B⋯O1	0.90	2.15	3.048 (3)	179
N1—H1A⋯O2ⁱ	0.90	2.35	3.141 (3)	147
N1—H1A⋯O1ⁱ	0.90	2.53	3.377 (4)	156
N4—H4A⋯O2ⁱ	0.90	2.34	3.175 (3)	154
N6—H6A⋯O1ⁱ	0.90	2.56	3.326 (3)	143
N1—H1B⋯O2ⁱⁱ	0.90	2.11	3.002 (3)	173
N2—H2A⋯F4Aⁱⁱ	0.90	2.47	3.267 (15)	148
N3—H3A⋯O3ⁱⁱ	0.90	2.09	2.958 (3)	162
N5—H5A⋯O3ⁱⁱ	0.90	2.36	3.126 (3)	143
N2—H2A⋯O4ⁱⁱⁱ	0.90	2.41	3.037 (3)	127
N4—H4B⋯O4^iv	0.90	2.11	2.997 (3)	168
N5—H5B⋯O3^iv	0.90	2.13	3.013 (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.

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

Supporting information

Crystal structure: contains datablocks global, I, publication_text. DOI: 10.1107/S1600536808001438/wn2235sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808001438/wn2235Isup2.hkl

checkCIF report

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.

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

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)₂	Z = 2
M_r = 469.90	F(000) = 482
Triclinic, P1	D_x = 1.679 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.582 (6) Å	Cell parameters from 250 reflections
b = 9.316 (6) Å	θ = 18–24°
c = 12.859 (7) Å	µ = 1.26 mm⁻¹
α = 74.73 (3)°	T = 293 K
β = 84.69 (4)°	Prism, blue
γ = 69.56 (3)°	0.15 × 0.1 × 0.08 mm
V = 929.3 (10) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4277 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tube	θ_max = 30.0°, θ_min = 1.6°
Graphite monochromator	h = −11→12
Detector resolution: 0.1 pixels mm^-1	k = 0→13
ϕ and ω scans	l = −17→18
5406 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0567P)²] where P = (F_o² + 2F_c²)/3
5406 reflections	(Δ/σ)_max = 0.001
300 parameters	Δρ_max = 0.24 e Å⁻³
45 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Cu(C₂H₈N₂)₃](C₂F₃O₂)₂	γ = 69.56 (3)°
M_r = 469.90	V = 929.3 (10) Å³
Triclinic, P1	Z = 2
a = 8.582 (6) Å	Mo Kα radiation
b = 9.316 (6) Å	µ = 1.26 mm⁻¹
c = 12.859 (7) Å	T = 293 K
α = 74.73 (3)°	0.15 × 0.1 × 0.08 mm
β = 84.69 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4277 reflections with I > 2σ(I)
5406 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	45 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 0.94	Δρ_max = 0.24 e Å⁻³
5406 reflections	Δρ_min = −0.25 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.94303 (3)	0.85236 (3)	0.778785 (18)	0.03254 (8)
N1	0.8821 (2)	0.8734 (2)	0.93404 (13)	0.0444 (3)
H1A	0.9694	0.8131	0.9777	0.053*
H1B	0.8587	0.9745	0.9362	0.053*
C1	0.7376 (3)	0.8237 (3)	0.97256 (17)	0.0486 (5)
H1C	0.6921	0.8610	1.0363	0.058*
H1D	0.7726	0.7092	0.9923	0.058*
C2	0.6060 (3)	0.8885 (3)	0.88718 (19)	0.0503 (5)
H2C	0.5139	0.8505	0.9121	0.060*
H2D	0.5641	1.0031	0.8708	0.060*
N2	0.6812 (2)	0.8352 (2)	0.79038 (16)	0.0495 (4)
H2A	0.6212	0.8977	0.7314	0.059*
H2B	0.6866	0.7350	0.7968	0.059*
N3	0.8604 (2)	1.1007 (2)	0.71134 (15)	0.0471 (4)
H3A	0.8004	1.1244	0.6515	0.057*
H3B	0.7948	1.1505	0.7589	0.057*
C3	1.0036 (3)	1.1543 (3)	0.68450 (19)	0.0539 (5)
H3C	0.9672	1.2681	0.6739	0.065*
H3D	1.0531	1.1292	0.6177	0.065*
C4	1.1308 (3)	1.0764 (3)	0.77268 (19)	0.0510 (5)
H4C	1.2266	1.1102	0.7523	0.061*
H4D	1.0843	1.1079	0.8382	0.061*
N4	1.1826 (2)	0.9040 (2)	0.79228 (15)	0.0457 (4)
H4A	1.2277	0.8564	0.8583	0.055*
H4B	1.2577	0.8695	0.7428	0.055*
N5	0.9835 (2)	0.8096 (2)	0.62842 (13)	0.0453 (4)
H5A	0.8923	0.8658	0.5873	0.054*
H5B	1.0688	0.8396	0.5965	0.054*
C5	1.0217 (3)	0.6405 (3)	0.6384 (2)	0.0540 (5)
H5C	1.0712	0.6134	0.5721	0.065*
H5D	0.9208	0.6139	0.6522	0.065*
C6	1.1414 (3)	0.5510 (3)	0.7304 (2)	0.0541 (5)
H6C	1.1649	0.4382	0.7420	0.065*
H6D	1.2451	0.5721	0.7144	0.065*
N6	1.0652 (2)	0.6024 (2)	0.82682 (15)	0.0482 (4)
H6A	1.1435	0.5783	0.8766	0.058*
H6B	0.9914	0.5539	0.8555	0.058*
C7	0.7420 (3)	0.3504 (3)	0.91576 (18)	0.0494 (4)
C8	0.5826 (4)	0.4304 (4)	0.8472 (3)	0.0722 (6)
C9	0.5876 (3)	0.1740 (3)	0.4611 (2)	0.0526 (5)
C10	0.4415 (4)	0.2533 (4)	0.5269 (3)	0.0749 (6)
O1	0.8137 (3)	0.4407 (2)	0.92515 (17)	0.0722 (5)
O2	0.7776 (3)	0.2083 (2)	0.95315 (17)	0.0721 (5)
O3	0.7270 (2)	0.1248 (2)	0.50104 (16)	0.0693 (5)
O4	0.5502 (3)	0.1706 (3)	0.37227 (17)	0.0780 (6)
F1A	0.495 (2)	0.5750 (14)	0.8639 (12)	0.087 (2)	0.55 (3)
F2A	0.4769 (16)	0.3531 (13)	0.8668 (13)	0.089 (3)	0.55 (3)
F3A	0.6064 (18)	0.4591 (14)	0.7404 (6)	0.093 (3)	0.55 (3)
F1B	0.471 (2)	0.537 (2)	0.8865 (14)	0.083 (2)	0.45 (3)
F2B	0.5182 (17)	0.3267 (11)	0.8290 (14)	0.088 (2)	0.45 (3)
F3B	0.6454 (13)	0.4960 (16)	0.7584 (10)	0.084 (3)	0.45 (3)
F4A	0.4601 (19)	0.166 (3)	0.6294 (12)	0.095 (4)	0.31 (2)
F5A	0.2886 (15)	0.281 (3)	0.4998 (12)	0.090 (4)	0.31 (2)
F6A	0.460 (3)	0.3837 (19)	0.529 (2)	0.110 (5)	0.31 (2)
F4B	0.4729 (10)	0.2254 (9)	0.6304 (5)	0.0850 (12)	0.69 (2)
F5B	0.3116 (8)	0.2068 (10)	0.5228 (6)	0.0872 (13)	0.69 (2)
F6B	0.3834 (11)	0.4109 (4)	0.4916 (4)	0.0858 (16)	0.69 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.03390 (11)	0.03383 (12)	0.03075 (11)	−0.01198 (8)	−0.00040 (7)	−0.00858 (8)
N1	0.0453 (9)	0.0514 (10)	0.0380 (6)	−0.0172 (8)	0.0030 (6)	−0.0134 (6)
C1	0.0495 (12)	0.0522 (12)	0.0418 (11)	−0.0159 (10)	0.0017 (9)	−0.0102 (9)
C2	0.0459 (11)	0.0535 (12)	0.0534 (12)	−0.0178 (10)	−0.0004 (9)	−0.0151 (10)
N2	0.0431 (7)	0.0582 (10)	0.0527 (10)	−0.0214 (8)	0.0005 (7)	−0.0173 (9)
N3	0.0516 (9)	0.0419 (7)	0.0458 (9)	−0.0141 (6)	−0.0022 (7)	−0.0090 (6)
C3	0.0558 (13)	0.0551 (13)	0.0501 (12)	−0.0207 (11)	−0.0030 (10)	−0.0082 (10)
C4	0.0567 (13)	0.0513 (12)	0.0484 (12)	−0.0217 (10)	−0.0007 (10)	−0.0126 (10)
N4	0.0435 (7)	0.0539 (10)	0.0436 (9)	−0.0214 (7)	0.0008 (6)	−0.0122 (8)
N5	0.0497 (9)	0.0504 (9)	0.0371 (7)	−0.0169 (8)	−0.0005 (6)	−0.0130 (7)
C5	0.0562 (13)	0.0536 (13)	0.0544 (13)	−0.0187 (10)	−0.0003 (10)	−0.0168 (11)
C6	0.0556 (13)	0.0511 (12)	0.0564 (13)	−0.0160 (10)	0.0011 (10)	−0.0178 (11)
N6	0.0492 (10)	0.0468 (10)	0.0468 (10)	−0.0151 (8)	−0.0046 (8)	−0.0085 (8)
C7	0.0437 (11)	0.0599 (10)	0.0441 (11)	−0.0142 (9)	0.0010 (8)	−0.0166 (9)
C8	0.0540 (14)	0.0761 (15)	0.0748 (13)	−0.0134 (9)	−0.0125 (11)	−0.0069 (13)
C9	0.0515 (10)	0.0506 (12)	0.0544 (11)	−0.0160 (10)	0.0046 (9)	−0.0141 (10)
C10	0.0646 (14)	0.0808 (12)	0.0766 (12)	−0.0185 (13)	0.0130 (13)	−0.0279 (14)
O1	0.0695 (12)	0.0765 (11)	0.0789 (13)	−0.0323 (10)	−0.0057 (10)	−0.0208 (10)
O2	0.0746 (12)	0.0622 (9)	0.0781 (13)	−0.0197 (9)	−0.0112 (10)	−0.0157 (9)
O3	0.0593 (10)	0.0788 (13)	0.0688 (11)	−0.0210 (9)	−0.0023 (8)	−0.0191 (10)
O4	0.0763 (13)	0.0897 (15)	0.0685 (11)	−0.0219 (11)	−0.0079 (9)	−0.0262 (11)
F1A	0.094 (5)	0.078 (3)	0.086 (5)	−0.026 (2)	−0.003 (3)	−0.018 (4)
F2A	0.085 (4)	0.089 (3)	0.097 (5)	−0.036 (3)	−0.012 (3)	−0.018 (3)
F3A	0.099 (5)	0.099 (4)	0.0789 (16)	−0.032 (3)	−0.003 (2)	−0.0216 (19)
F1B	0.077 (4)	0.089 (6)	0.085 (6)	−0.026 (4)	0.004 (3)	−0.025 (5)
F2B	0.086 (5)	0.093 (3)	0.089 (6)	−0.033 (3)	0.006 (4)	−0.029 (3)
F3B	0.078 (4)	0.102 (5)	0.075 (3)	−0.033 (3)	0.001 (2)	−0.022 (3)
F4A	0.070 (4)	0.113 (10)	0.093 (4)	−0.038 (6)	0.005 (3)	0.000 (6)
F5A	0.078 (3)	0.116 (11)	0.083 (5)	−0.038 (6)	0.005 (3)	−0.029 (6)
F6A	0.097 (9)	0.098 (5)	0.144 (12)	−0.056 (6)	0.016 (8)	−0.020 (7)
F4B	0.085 (3)	0.091 (3)	0.0800 (15)	−0.033 (2)	0.0010 (16)	−0.0179 (17)
F5B	0.080 (2)	0.091 (3)	0.090 (3)	−0.030 (3)	−0.0023 (18)	−0.020 (3)
F6B	0.082 (4)	0.0829 (12)	0.090 (2)	−0.0239 (16)	−0.0062 (19)	−0.0192 (13)

Geometric parameters (Å, º) top

Cu1—N5	2.050 (2)	N5—H5A	0.9000
Cu1—N1	2.059 (2)	N5—H5B	0.9000
Cu1—N3	2.126 (2)	C5—C6	1.503 (3)
Cu1—N6	2.136 (2)	C5—H5C	0.9700
Cu1—N2	2.297 (2)	C5—H5D	0.9700
Cu1—N4	2.300 (2)	C6—N6	1.462 (3)
N1—C1	1.471 (3)	C6—H6C	0.9700
N1—H1A	0.9000	C6—H6D	0.9700
N1—H1B	0.9000	N6—H6A	0.9000
C1—C2	1.500 (3)	N6—H6B	0.9000
C1—H1C	0.9700	C7—O2	1.219 (3)
C1—H1D	0.9700	C7—O1	1.237 (3)
C2—N2	1.471 (3)	C7—C8	1.539 (4)
C2—H2C	0.9700	C8—F1B	1.291 (11)
C2—H2D	0.9700	C8—F3B	1.311 (7)
N2—H2A	0.9000	C8—F2A	1.312 (7)
N2—H2B	0.9000	C8—F3A	1.338 (7)
N3—C3	1.462 (3)	C8—F2B	1.345 (9)
N3—H3A	0.9000	C8—F1A	1.357 (9)
N3—H3B	0.9000	C9—O4	1.225 (3)
C3—C4	1.499 (3)	C9—O3	1.230 (3)
C3—H3C	0.9700	C9—C10	1.524 (4)
C3—H3D	0.9700	C10—F6A	1.286 (10)
C4—N4	1.466 (3)	C10—F5A	1.308 (11)
C4—H4C	0.9700	C10—F4B	1.322 (6)
C4—H4D	0.9700	C10—F5B	1.338 (5)
N4—H4A	0.9000	C10—F6B	1.338 (5)
N4—H4B	0.9000	C10—F4A	1.343 (11)
N5—C5	1.464 (3)

N5—Cu1—N1	171.52 (7)	H5A—N5—H5B	108.3
N5—Cu1—N3	91.32 (8)	N5—C5—C6	107.7 (2)
N1—Cu1—N3	93.88 (8)	N5—C5—H5C	110.2
N5—Cu1—N6	81.82 (8)	C6—C5—H5C	110.2
N1—Cu1—N6	93.95 (8)	N5—C5—H5D	110.2
N3—Cu1—N6	169.22 (7)	C6—C5—H5D	110.2
N5—Cu1—N2	92.91 (8)	H5C—C5—H5D	108.5
N1—Cu1—N2	80.03 (8)	N6—C6—C5	108.1 (2)
N3—Cu1—N2	94.49 (8)	N6—C6—H6C	110.1
N6—Cu1—N2	94.15 (9)	C5—C6—H6C	110.1
N5—Cu1—N4	98.13 (8)	N6—C6—H6D	110.1
N1—Cu1—N4	89.38 (8)	C5—C6—H6D	110.1
N3—Cu1—N4	79.81 (8)	H6C—C6—H6D	108.4
N6—Cu1—N4	92.88 (8)	C6—N6—Cu1	107.29 (14)
N2—Cu1—N4	167.65 (7)	C6—N6—H6A	110.3
C1—N1—Cu1	110.81 (14)	Cu1—N6—H6A	110.3
C1—N1—H1A	109.5	C6—N6—H6B	110.3
Cu1—N1—H1A	109.5	Cu1—N6—H6B	110.3
C1—N1—H1B	109.5	H6A—N6—H6B	108.5
Cu1—N1—H1B	109.5	O2—C7—O1	129.9 (2)
H1A—N1—H1B	108.1	O2—C7—C8	115.2 (2)
N1—C1—C2	110.86 (18)	O1—C7—C8	114.9 (2)
N1—C1—H1C	109.5	F1B—C8—F3B	110.6 (7)
C2—C1—H1C	109.5	F1B—C8—F2A	86.2 (6)
N1—C1—H1D	109.5	F3B—C8—F2A	133.3 (5)
C2—C1—H1D	109.5	F1B—C8—F3A	118.9 (10)
H1C—C1—H1D	108.1	F3B—C8—F3A	28.3 (3)
N2—C2—C1	107.94 (19)	F2A—C8—F3A	105.2 (5)
N2—C2—H2C	110.1	F1B—C8—F2B	110.6 (7)
C1—C2—H2C	110.1	F3B—C8—F2B	110.6 (5)
N2—C2—H2D	110.1	F2A—C8—F2B	27.2 (3)
C1—C2—H2D	110.1	F3A—C8—F2B	82.7 (5)
H2C—C2—H2D	108.4	F1B—C8—F1A	21.0 (6)
C2—N2—Cu1	105.49 (14)	F3B—C8—F1A	90.5 (6)
C2—N2—H2A	110.6	F2A—C8—F1A	104.9 (5)
Cu1—N2—H2A	110.6	F3A—C8—F1A	103.9 (6)
C2—N2—H2B	110.6	F2B—C8—F1A	126.1 (7)
Cu1—N2—H2B	110.6	F1B—C8—C7	112.6 (9)
H2A—N2—H2B	108.8	F3B—C8—C7	98.8 (7)
C3—N3—Cu1	109.77 (15)	F2A—C8—C7	114.9 (4)
C3—N3—H3A	109.7	F3A—C8—C7	115.3 (7)
Cu1—N3—H3A	109.7	F2B—C8—C7	113.1 (5)
C3—N3—H3B	109.7	F1A—C8—C7	111.6 (7)
Cu1—N3—H3B	109.7	O4—C9—O3	128.0 (3)
H3A—N3—H3B	108.2	O4—C9—C10	114.6 (3)
N3—C3—C4	110.8 (2)	O3—C9—C10	117.4 (3)
N3—C3—H3C	109.5	F6A—C10—F5A	109.5 (6)
C4—C3—H3C	109.5	F6A—C10—F4B	79.6 (10)
N3—C3—H3D	109.5	F5A—C10—F4B	117.5 (7)
C4—C3—H3D	109.5	F6A—C10—F5B	135.3 (9)
H3C—C3—H3D	108.1	F5A—C10—F5B	28.1 (8)
N4—C4—C3	110.08 (19)	F4B—C10—F5B	105.9 (4)
N4—C4—H4C	109.6	F6A—C10—F6B	34.5 (11)
C3—C4—H4C	109.6	F5A—C10—F6B	77.3 (8)
N4—C4—H4D	109.6	F4B—C10—F6B	105.2 (4)
C3—C4—H4D	109.6	F5B—C10—F6B	105.2 (3)
H4C—C4—H4D	108.2	F6A—C10—F4A	105.5 (7)
C4—N4—Cu1	105.13 (14)	F5A—C10—F4A	106.4 (8)
C4—N4—H4A	110.7	F4B—C10—F4A	26.0 (9)
Cu1—N4—H4A	110.7	F5B—C10—F4A	86.2 (7)
C4—N4—H4B	110.7	F6B—C10—F4A	128.0 (12)
Cu1—N4—H4B	110.7	F6A—C10—C9	105.3 (6)
H4A—N4—H4B	108.8	F5A—C10—C9	120.7 (7)
C5—N5—Cu1	109.29 (14)	F4B—C10—C9	114.9 (4)
C5—N5—H5A	109.8	F5B—C10—C9	111.5 (4)
Cu1—N5—H5A	109.8	F6B—C10—C9	113.3 (3)
C5—N5—H5B	109.8	F4A—C10—C9	108.5 (9)
Cu1—N5—H5B	109.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···F1A	0.90	2.54	3.248 (17)	136
N2—H2B···F3B	0.90	2.55	3.41 (2)	161
N6—H6B···O1	0.90	2.15	3.048 (3)	179
N1—H1A···O2ⁱ	0.90	2.35	3.141 (3)	147
N1—H1A···O1ⁱ	0.90	2.53	3.377 (4)	156
N4—H4A···O2ⁱ	0.90	2.34	3.175 (3)	154
N6—H6A···O1ⁱ	0.90	2.56	3.326 (3)	143
N1—H1B···O2ⁱⁱ	0.90	2.11	3.002 (3)	173
N2—H2A···F4Aⁱⁱ	0.90	2.47	3.267 (15)	148
N3—H3A···O3ⁱⁱ	0.90	2.09	2.958 (3)	162
N5—H5A···O3ⁱⁱ	0.90	2.36	3.126 (3)	143
N2—H2A···O4ⁱⁱⁱ	0.90	2.41	3.037 (3)	127
N4—H4B···O4^iv	0.90	2.11	2.997 (3)	168
N5—H5B···O3^iv	0.90	2.13	3.013 (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.

Experimental details

Crystal data
Chemical formula	[Cu(C₂H₈N₂)₃](C₂F₃O₂)₂
M_r	469.90
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.582 (6), 9.316 (6), 12.859 (7)
α, β, γ (°)	74.73 (3), 84.69 (4), 69.56 (3)
V (Å³)	929.3 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.26
Crystal size (mm)	0.15 × 0.1 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	?, 5406, 4277
R_int	?
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.092, 0.94
No. of reflections	5406
No. of parameters	300
No. of restraints	45
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.25

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···F1A	0.90	2.54	3.248 (17)	136.0
N2—H2B···F3B	0.90	2.55	3.41 (2)	161.0
N6—H6B···O1	0.90	2.15	3.048 (3)	179.2
N1—H1A···O2ⁱ	0.90	2.35	3.141 (3)	147.2
N1—H1A···O1ⁱ	0.90	2.53	3.377 (4)	156.4
N4—H4A···O2ⁱ	0.90	2.34	3.175 (3)	154.4
N6—H6A···O1ⁱ	0.90	2.56	3.326 (3)	143.3
N1—H1B···O2ⁱⁱ	0.90	2.11	3.002 (3)	172.8
N2—H2A···F4Aⁱⁱ	0.90	2.47	3.267 (15)	148.3
N3—H3A···O3ⁱⁱ	0.90	2.09	2.958 (3)	162.1
N5—H5A···O3ⁱⁱ	0.90	2.36	3.126 (3)	143.3
N2—H2A···O4ⁱⁱⁱ	0.90	2.41	3.037 (3)	127.0
N4—H4B···O4^iv	0.90	2.11	2.997 (3)	167.8
N5—H5B···O3^iv	0.90	2.13	3.013 (3)	167.0

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

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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