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In the crystal structure of the title complex, [Cu2(C10H20N4O2)(C10H8N2)2](ClO4)2, the deprotonated dmaeoxd2− ligand {H2dmaeoxd is N,N′-bis­[2-(dimethyl­amino)­ethyl]­oxamide} occupies an inversion centre at the mid-point of the central C—C bond and is thus in a trans conformation. The two CuII atoms are located in slightly distorted square-based pyramidal environments. The binuclear units inter­act with each other via π–π inter­actions to form a one-dimensional chain extending in the c direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107067558/av3130sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107067558/av3130Isup2.hkl
Contains datablock I

CCDC reference: 682789

Comment top

There has been a great interest in the crystal engineering of self-assembled supramolecular architectures formed through relatively weak interactions such as hydrogen bonds and ππ stacking interactions (Blake et al., 1999; Lin et al., 2003). It is well known that N,N'-bis(substituent)oxamides could be good candidates for the formation of polynuclear complexes, because their coordinating ability towards transition metal ions can be modified and tuned by changing the nature of the amide substituents (Ojima & Nonoyama, 1988). A typical feature of these ligands is an easy transformation of cis–trans conformations, which makes it practical to design tunable molecular materials with desired properties (Chen et al., 1998). To date, many polynuclear complexes containing oxamide-bridges have been synthesized and their properties studied extensively (Messori et al., 2003; Wang et al., 2004). However, as far as we are aware, there are few studies of the influence of substituents in the amine groups of the bridging ligand on their coordination environments and supramolecular structures. Taking into account the above facts and in continuation of our work on polynuclear complexes with bridging oxamide groups (Li et al., 2003, 2004), we chose N,N'-bis[2-(dimethylamino)ethyl]oxamide (H2dmaeoxd) as bridging ligand and 2,2'-bipyridine as terminal ligand to synthesize the title binuclear copper(II) complex formulated as [Cu(dmaeoxd)(bpy)2](ClO4)2, (I). The influence of the methyl substituents in the amine groups of the bridging ligand on the structures is also discussed.

The molecular structure of (I) (Fig. 1) consists of a centrosymmetric dinuclear copper(II) cation and two uncoordinated perchlorate anions. The [Cu2(dmaeoxd)(bpy)2]2+ cation has a transoid conformation and occupies a special inversion centre at the middle of the C15—C15i bond [symmetry code: (i) -x, -y, 2 - z], which is similar to another complex, [Cu(apox)(bpy)2](NO3)2, (II) [H2(apox) is N,N'-bis(3-aminopropyl)oxamide; Boyd & Rickard, 2006]. The N4/O1/C15/C15i/N4i/O1i bridging group is planar, and atom Cu1 is displaced by 0.069 (4) Å from this plane. The Cu···Cu separation through the bridge is 5.249 (2) Å. Within the oxamide fragment, the C—O and C—N bonds have partial double-bond character [N4—C15 = 1.292 (4) and C15—O1 = 1.263 (3) Å, Table 1], while the length of the C15—C15i single bond [1.533 (5) Å] is between the value of 1.541 (3) Å in [H4dmaeoxd](NO3)2 (Sun et al., 2006) and that of 1.520 Å in compound (II).

Due to the rigidity of the ligands, the pentacoordinated CuII atom has a distorted square-pyramidal geometry. Atom N1 of the bpy ligand occupies the apical position, while the other N atom, N2, as well as two N atoms (N3, N4) and one O atom (O1i) from the dmaeoxd ligand, form the basal coordination plane, with a maximum deviation of 0.0238 (13) Å for atom N4. Atom Cu1 is displaced out of the basal plane towards the apex by 0.0751 (17) Å. The axial Cu1—N1 distance of 2.218 (3) Å is significantly longer than those in the basal plane. The bis-tridentate dmaeoxd ligand produces two five-membered chelate rings with each CuII atom. The ring formed by the ethylenediamine fragment adopts a twist form, with puckering parameters (Cremer & Pople, 1975) of ϕ = 56.7 (4)° and Q = 0.448 (3) Å. In the ring, the Cu1—N3 (amine) distance [2.092 (3) Å] is longer than the Cu1—N4 (amidic) distance [1.903 (2) Å] by 0.189 (4) Å. This difference is larger than that of 0.0698 (18) Å in compound (II), in which the corresponding Cu—N bonds are in a six-membered ring. The dihedral angle between the oxamide bridge and the coordination basal plane is 8.07 (15)°, which is much smaller than the angle of 19.7° in compound (II).

The terminal bpy ligand is present in the usual chelating bidentate mode with a bite angle of 78.36 (10)°. The C5—N1, C6—N2 and C5—C6 distances of 1.332 (4), 1.351 (4) and 1.494 (4) Å, respectively, are typical CN and Csp2—Csp2 values. The 12-atom plane of the bpy ligand (r.m.s. deviation 0.0238 Å) is nearly perpendicular to the oxamide bridge, with a dihedral angle of 84.03 (7)°, which is larger than the angle of 72.5° in compound (II).

Compared with compound (II), the bpy ligands of the title compound do not contribute to C—H···O hydrogen bonds. In addition, due to the substitution of the H atoms of the primary amine by a methyl group, the dmaeoxd ligand does not participate in any hydrogen bonds, which is different from eight other reported binuclear complexes bridged by oxen [H2oxen is N,N'-bis(2-aminoethyl)oxamide] (Cambridge Structural Database, Version?; Allen, 2002). The pyridine rings of the bpy ligand are involved in offset ππ stacking interactions, by means of which, as shown in Fig. 2, the [Cu2(dmaeoxd)(bpy)2]2+ cations assemble into a two-dimensional supramolecular structure parallel to the bc plane. The nearest separation is 3.405 (5) Å to atom C10iii [symmetry code: (iii) -x, -y, 1 - z]. Further investigation concerning the influence of substituents on supramolecular structure is in progress in our laboratory.

Related literature top

For related literature, see: Allen (2002); Blake et al. (1999); Boyd & Rickard (2006); Chen et al. (1998); Cremer & Pople (1975); Li et al. (2003, 2004); Lin et al. (2003); Messori et al. (2003); Ojima & Nonoyama (1988); Ojima & Yamada (1970); Sun et al. (2006); Wang et al. (2004).

Experimental top

All reagents were of AR grade and were used without further purification. The H2dmaeoxd ligand was synthesized according to the method of Ojima & Yamada (1970). [Cu(dmaeoxd)(bpy)2](ClO4)2 was obtained as follows. To a solution of H2dmaeoxd (0.0230 g, 0.1 mmol) in methanol (10 ml) were added successively piperidine (0.2 mmol) and a solution of Cu(ClO4)2·6H2O (0.0741 g, 0.2 mmol) in methanol (5 ml). After stirring for 20 min, bpy (0.0312 g, 0.2 mmol) in methanol (5 ml) was added. The reaction mixture was stirred at 333 K for a further 2 h. The green precipitate which formed was collected by suction filtration, washed several times with methanol and diethyl ether, and dried over P2O5 under reduced pressure (yield 0.0637 g, 73%). Green crystals of the title compound suitable for X-ray analysis were obtained from a methanol–acetonitrile (1:1 v/v) mixture by slow evaporation for one week at room temperature. Analysis, calculated for C30H36Cl2N8O10Cu2 (%): C 41.58, H 4.19, N 12.93%; found: C 41.52, H 4.14, N 12.92%. Spectroscopic analysis: IR (KBr pellet, γ, cm-1): 1648 (vs), 1474 (m), 1442 (s), 1090 (vs), 770 (m), 623 (s).

Refinement top

All H atoms were positioned geometrically, with C—H distances of 0.93 (sp2C—H), 0.97 (CH2) or 0.96 Å (CH3). They were then treated using a riding model, with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(methyl C).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry code: (i) -x, -y, 2 - z.]
[Figure 2] Fig. 2. A view showing the ππ stacking interactions, viewed down the c axis. H atoms and the ClO4- anion have been omitted for clarity. [Symmetry codes: (i) -x, -y, 2 - z; (ii) -x, 1 - y, 1 - z; (iii) -x, -y, 1 - z.]
{µ-N,N'-Bis[2-(dimethylamino)ethyl]oxamidato(2-)-κ6N,N',O':N'',N''',O}bis[(2,2'-bipyridine-κ2N,N')copper(II)] bis(perchlorate) top
Crystal data top
[Cu2(C10H20N4O2)(C10H8N2)2](ClO4)2Z = 1
Mr = 866.67F(000) = 444
Triclinic, P1Dx = 1.610 Mg m3
Hall symbol: -p 1Mo Kα radiation, λ = 0.71073 Å
a = 8.6631 (17) ÅCell parameters from 2853 reflections
b = 10.144 (2) Åθ = 2.4–27.7°
c = 10.569 (2) ŵ = 1.41 mm1
α = 79.73 (3)°T = 298 K
β = 78.02 (3)°Block, green
γ = 87.08 (3)°0.22 × 0.16 × 0.13 mm
V = 893.9 (3) Å3
Data collection top
Bruker APEX area-detector
diffractometer
3189 independent reflections
Radiation source: fine-focus sealed tube2778 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ϕ and ω scansθmax = 25.2°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1010
Tmin = 0.747, Tmax = 0.838k = 127
4847 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0678P)2 + 0.3896P]
where P = (Fo2 + 2Fc2)/3
3189 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
[Cu2(C10H20N4O2)(C10H8N2)2](ClO4)2γ = 87.08 (3)°
Mr = 866.67V = 893.9 (3) Å3
Triclinic, P1Z = 1
a = 8.6631 (17) ÅMo Kα radiation
b = 10.144 (2) ŵ = 1.41 mm1
c = 10.569 (2) ÅT = 298 K
α = 79.73 (3)°0.22 × 0.16 × 0.13 mm
β = 78.02 (3)°
Data collection top
Bruker APEX area-detector
diffractometer
3189 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2778 reflections with I > 2σ(I)
Tmin = 0.747, Tmax = 0.838Rint = 0.014
4847 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 1.05Δρmax = 0.53 e Å3
3189 reflectionsΔρmin = 0.40 e Å3
235 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
Cu10.13801 (4)0.14679 (4)0.77887 (3)0.04023 (15)
O10.0559 (2)0.0280 (2)1.15406 (18)0.0450 (5)
N10.0220 (3)0.3240 (3)0.7625 (3)0.0495 (6)
N20.1150 (3)0.1671 (2)0.5931 (2)0.0385 (5)
N30.3601 (3)0.2320 (3)0.7507 (2)0.0481 (6)
N40.1634 (3)0.1025 (3)0.9562 (2)0.0424 (6)
C10.0927 (5)0.3934 (4)0.8552 (4)0.0676 (10)
H10.05940.37930.93480.081*
C20.2129 (5)0.4850 (4)0.8378 (4)0.0705 (11)
H20.26070.53070.90490.085*
C30.2603 (4)0.5073 (4)0.7205 (4)0.0675 (10)
H30.33880.57060.70520.081*
C40.1901 (4)0.4348 (3)0.6252 (4)0.0546 (8)
H40.22160.44770.54490.066*
C50.0724 (3)0.3424 (3)0.6498 (3)0.0397 (6)
C60.0064 (3)0.2565 (3)0.5534 (3)0.0381 (6)
C70.0291 (4)0.2644 (3)0.4309 (3)0.0501 (7)
H70.10450.32580.40450.060*
C80.0474 (4)0.1813 (4)0.3482 (3)0.0548 (8)
H80.02250.18470.26620.066*
C90.1602 (4)0.0938 (4)0.3867 (3)0.0543 (8)
H90.21530.03890.33050.065*
C100.1911 (4)0.0881 (3)0.5101 (3)0.0477 (7)
H100.26710.02760.53680.057*
C110.3788 (5)0.3565 (4)0.6500 (4)0.0726 (11)
H11A0.47540.39920.64950.109*
H11B0.29140.41640.67070.109*
H11C0.38150.33410.56510.109*
C120.4884 (5)0.1379 (5)0.7137 (5)0.0783 (12)
H12A0.58740.17580.71460.117*
H12B0.48840.12110.62720.117*
H12C0.47340.05540.77510.117*
C130.3610 (5)0.2690 (4)0.8806 (3)0.0636 (10)
H13A0.29410.34740.89200.076*
H13B0.46740.29070.88470.076*
C140.3006 (4)0.1517 (4)0.9907 (3)0.0578 (9)
H14A0.38090.08180.99600.069*
H14B0.27200.18181.07470.069*
C150.0627 (3)0.0201 (3)1.0343 (3)0.0383 (6)
Cl10.35087 (11)0.25757 (10)0.77526 (10)0.0666 (3)
O110.4172 (6)0.2598 (8)0.6467 (4)0.202 (3)
O120.4653 (5)0.2779 (6)0.8502 (5)0.154 (2)
O130.2628 (6)0.1442 (5)0.7901 (6)0.162 (2)
O140.2401 (7)0.3631 (5)0.8124 (5)0.1421 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0457 (2)0.0484 (2)0.0292 (2)0.00128 (16)0.01167 (14)0.00859 (15)
O10.0515 (11)0.0576 (13)0.0303 (10)0.0070 (10)0.0158 (8)0.0089 (9)
N10.0554 (15)0.0515 (16)0.0449 (14)0.0055 (12)0.0102 (11)0.0185 (12)
N20.0410 (12)0.0443 (13)0.0321 (11)0.0006 (10)0.0095 (9)0.0093 (10)
N30.0480 (14)0.0586 (16)0.0380 (13)0.0084 (12)0.0077 (11)0.0078 (11)
N40.0482 (13)0.0507 (14)0.0323 (12)0.0050 (12)0.0149 (10)0.0091 (10)
C10.080 (3)0.073 (2)0.055 (2)0.010 (2)0.0111 (18)0.0311 (18)
C20.066 (2)0.064 (2)0.082 (3)0.0085 (19)0.001 (2)0.037 (2)
C30.0507 (19)0.057 (2)0.094 (3)0.0063 (17)0.0091 (19)0.019 (2)
C40.0467 (17)0.0515 (19)0.067 (2)0.0026 (15)0.0153 (15)0.0089 (16)
C50.0388 (14)0.0378 (15)0.0423 (15)0.0060 (12)0.0072 (12)0.0059 (12)
C60.0379 (14)0.0414 (15)0.0361 (14)0.0077 (12)0.0081 (11)0.0066 (12)
C70.0573 (18)0.0532 (18)0.0446 (17)0.0005 (15)0.0231 (14)0.0060 (14)
C80.070 (2)0.066 (2)0.0344 (15)0.0090 (18)0.0192 (14)0.0117 (14)
C90.063 (2)0.065 (2)0.0394 (16)0.0040 (17)0.0080 (14)0.0219 (15)
C100.0516 (17)0.0524 (18)0.0412 (16)0.0063 (14)0.0099 (13)0.0151 (14)
C110.074 (2)0.075 (3)0.067 (2)0.021 (2)0.0193 (19)0.003 (2)
C120.056 (2)0.086 (3)0.093 (3)0.004 (2)0.009 (2)0.025 (2)
C130.066 (2)0.079 (3)0.0515 (19)0.0226 (19)0.0153 (16)0.0175 (18)
C140.0598 (19)0.077 (2)0.0423 (17)0.0174 (18)0.0217 (15)0.0070 (16)
C150.0448 (15)0.0435 (15)0.0306 (13)0.0023 (12)0.0130 (12)0.0113 (11)
Cl10.0624 (5)0.0731 (6)0.0720 (6)0.0187 (5)0.0241 (4)0.0263 (5)
O110.131 (4)0.391 (10)0.075 (3)0.017 (5)0.002 (3)0.046 (4)
O120.115 (3)0.243 (6)0.143 (4)0.059 (4)0.086 (3)0.085 (4)
O130.133 (4)0.105 (3)0.286 (7)0.050 (3)0.087 (4)0.092 (4)
O140.203 (5)0.108 (3)0.130 (4)0.038 (3)0.078 (3)0.003 (3)
Geometric parameters (Å, º) top
Cu1—N41.903 (2)C6—C71.379 (4)
Cu1—N21.988 (2)C7—C81.371 (5)
Cu1—O1i2.045 (2)C7—H70.9300
Cu1—N32.092 (3)C8—C91.362 (5)
Cu1—N12.218 (3)C8—H80.9300
O1—C151.263 (3)C9—C101.375 (4)
O1—Cu1i2.045 (2)C9—H90.9300
N1—C51.332 (4)C10—H100.9300
N1—C11.335 (4)C11—H11A0.9600
N2—C101.343 (4)C11—H11B0.9600
N2—C61.351 (4)C11—H11C0.9600
N3—C121.464 (5)C12—H12A0.9600
N3—C131.488 (4)C12—H12B0.9600
N3—C111.492 (5)C12—H12C0.9600
N4—C151.292 (4)C13—C141.537 (5)
N4—C141.449 (4)C13—H13A0.9700
C1—C21.379 (6)C13—H13B0.9700
C1—H10.9300C14—H14A0.9700
C2—C31.364 (6)C14—H14B0.9700
C2—H20.9300C15—C15i1.533 (5)
C3—C41.375 (5)Cl1—O131.362 (4)
C3—H30.9300Cl1—O111.364 (4)
C4—C51.382 (4)Cl1—O121.379 (4)
C4—H40.9300Cl1—O141.421 (5)
C5—C61.494 (4)
N4—Cu1—N2172.37 (10)C8—C7—H7120.2
N4—Cu1—O1i83.44 (9)C6—C7—H7120.2
N2—Cu1—O1i92.92 (9)C9—C8—C7119.7 (3)
N4—Cu1—N382.92 (10)C9—C8—H8120.2
N2—Cu1—N399.63 (10)C7—C8—H8120.2
O1i—Cu1—N3164.14 (10)C8—C9—C10118.9 (3)
N4—Cu1—N1108.19 (10)C8—C9—H9120.6
N2—Cu1—N178.36 (10)C10—C9—H9120.6
O1i—Cu1—N188.81 (10)N2—C10—C9122.1 (3)
N3—Cu1—N1103.12 (11)N2—C10—H10119.0
C15—O1—Cu1i109.10 (17)C9—C10—H10119.0
C5—N1—C1118.3 (3)N3—C11—H11A109.5
C5—N1—Cu1111.13 (19)N3—C11—H11B109.5
C1—N1—Cu1129.2 (3)H11A—C11—H11B109.5
C10—N2—C6118.9 (2)N3—C11—H11C109.5
C10—N2—Cu1123.1 (2)H11A—C11—H11C109.5
C6—N2—Cu1117.68 (18)H11B—C11—H11C109.5
C12—N3—C13111.8 (3)N3—C12—H12A109.5
C12—N3—C11109.0 (3)N3—C12—H12B109.5
C13—N3—C11108.4 (3)H12A—C12—H12B109.5
C12—N3—Cu1112.1 (2)N3—C12—H12C109.5
C13—N3—Cu1103.15 (19)H12A—C12—H12C109.5
C11—N3—Cu1112.3 (2)H12B—C12—H12C109.5
C15—N4—C14124.8 (2)N3—C13—C14109.8 (3)
C15—N4—Cu1116.41 (18)N3—C13—H13A109.7
C14—N4—Cu1118.5 (2)C14—C13—H13A109.7
N1—C1—C2122.7 (4)N3—C13—H13B109.7
N1—C1—H1118.6C14—C13—H13B109.7
C2—C1—H1118.6H13A—C13—H13B108.2
C3—C2—C1118.8 (3)N4—C14—C13105.7 (3)
C3—C2—H2120.6N4—C14—H14A110.6
C1—C2—H2120.6C13—C14—H14A110.6
C2—C3—C4118.9 (3)N4—C14—H14B110.6
C2—C3—H3120.6C13—C14—H14B110.6
C4—C3—H3120.6H14A—C14—H14B108.7
C3—C4—C5119.5 (3)O1—C15—N4129.1 (2)
C3—C4—H4120.3O1—C15—C15i118.8 (3)
C5—C4—H4120.3N4—C15—C15i112.2 (3)
N1—C5—C4121.7 (3)O13—Cl1—O11111.7 (4)
N1—C5—C6115.4 (2)O13—Cl1—O12113.2 (3)
C4—C5—C6122.9 (3)O11—Cl1—O12110.1 (3)
N2—C6—C7120.7 (3)O13—Cl1—O14104.8 (3)
N2—C6—C5116.2 (2)O11—Cl1—O14105.4 (4)
C7—C6—C5123.0 (3)O12—Cl1—O14111.1 (3)
C8—C7—C6119.6 (3)
N4—Cu1—N1—C5166.3 (2)C1—C2—C3—C42.0 (6)
N2—Cu1—N1—C59.7 (2)C2—C3—C4—C50.8 (5)
O1i—Cu1—N1—C583.6 (2)C1—N1—C5—C42.8 (5)
N3—Cu1—N1—C5107.0 (2)Cu1—N1—C5—C4170.8 (2)
N4—Cu1—N1—C10.1 (3)C1—N1—C5—C6177.0 (3)
N2—Cu1—N1—C1176.1 (3)Cu1—N1—C5—C69.0 (3)
O1i—Cu1—N1—C182.8 (3)C3—C4—C5—N11.7 (5)
N3—Cu1—N1—C186.6 (3)C3—C4—C5—C6178.1 (3)
O1i—Cu1—N2—C1094.2 (2)C10—N2—C6—C71.6 (4)
N3—Cu1—N2—C1076.0 (2)Cu1—N2—C6—C7172.3 (2)
N1—Cu1—N2—C10177.6 (3)C10—N2—C6—C5179.3 (3)
O1i—Cu1—N2—C679.4 (2)Cu1—N2—C6—C56.9 (3)
N3—Cu1—N2—C6110.3 (2)N1—C5—C6—N22.3 (4)
N1—Cu1—N2—C68.8 (2)C4—C5—C6—N2177.5 (3)
N4—Cu1—N3—C1292.2 (3)N1—C5—C6—C7178.6 (3)
N2—Cu1—N3—C1280.5 (3)C4—C5—C6—C71.6 (4)
O1i—Cu1—N3—C1261.3 (4)N2—C6—C7—C80.4 (5)
N1—Cu1—N3—C12160.7 (2)C5—C6—C7—C8179.5 (3)
N4—Cu1—N3—C1328.2 (2)C6—C7—C8—C91.4 (5)
N2—Cu1—N3—C13159.0 (2)C7—C8—C9—C102.0 (5)
O1i—Cu1—N3—C1359.1 (4)C6—N2—C10—C91.0 (4)
N1—Cu1—N3—C1378.9 (2)Cu1—N2—C10—C9172.5 (2)
N4—Cu1—N3—C11144.7 (3)C8—C9—C10—N20.8 (5)
N2—Cu1—N3—C1142.6 (3)C12—N3—C13—C1474.2 (4)
O1i—Cu1—N3—C11175.6 (3)C11—N3—C13—C14165.7 (3)
N1—Cu1—N3—C1137.6 (3)Cu1—N3—C13—C1446.4 (3)
O1i—Cu1—N4—C152.8 (2)C15—N4—C14—C13167.2 (3)
N3—Cu1—N4—C15169.1 (2)Cu1—N4—C14—C1319.3 (4)
N1—Cu1—N4—C1589.4 (2)N3—C13—C14—N444.0 (4)
O1i—Cu1—N4—C14176.8 (3)Cu1i—O1—C15—N4177.9 (3)
N3—Cu1—N4—C145.0 (2)Cu1i—O1—C15—C15i1.9 (4)
N1—Cu1—N4—C1496.6 (3)C14—N4—C15—O14.1 (5)
C5—N1—C1—C21.4 (6)Cu1—N4—C15—O1177.7 (2)
Cu1—N1—C1—C2167.0 (3)C14—N4—C15—C15i176.1 (3)
N1—C1—C2—C31.0 (6)Cu1—N4—C15—C15i2.4 (4)
Symmetry code: (i) x, y, z+2.

Experimental details

Crystal data
Chemical formula[Cu2(C10H20N4O2)(C10H8N2)2](ClO4)2
Mr866.67
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)8.6631 (17), 10.144 (2), 10.569 (2)
α, β, γ (°)79.73 (3), 78.02 (3), 87.08 (3)
V3)893.9 (3)
Z1
Radiation typeMo Kα
µ (mm1)1.41
Crystal size (mm)0.22 × 0.16 × 0.13
Data collection
DiffractometerBruker APEX area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.747, 0.838
No. of measured, independent and
observed [I > 2σ(I)] reflections
4847, 3189, 2778
Rint0.014
(sin θ/λ)max1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.110, 1.05
No. of reflections3189
No. of parameters235
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.40

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1994), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
Cu1—N41.903 (2)N1—C51.332 (4)
Cu1—N21.988 (2)N2—C61.351 (4)
Cu1—O1i2.045 (2)N4—C151.292 (4)
Cu1—N32.092 (3)C5—C61.494 (4)
Cu1—N12.218 (3)C15—C15i1.533 (5)
O1—C151.263 (3)
N4—Cu1—N2172.37 (10)N2—Cu1—N178.36 (10)
N4—Cu1—O1i83.44 (9)O1i—Cu1—N188.81 (10)
N2—Cu1—O1i92.92 (9)N3—Cu1—N1103.12 (11)
N4—Cu1—N382.92 (10)O1—C15—N4129.1 (2)
N2—Cu1—N399.63 (10)O1—C15—C15i118.8 (3)
O1i—Cu1—N3164.14 (10)N4—C15—C15i112.2 (3)
N4—Cu1—N1108.19 (10)
Cu1—N1—C5—C69.0 (3)Cu1—N2—C6—C56.9 (3)
Symmetry code: (i) x, y, z+2.
 

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