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The title compound, [Cu2(C13H14N3)2Cl2], is a neutral dimeric copper(II) complex. The two CuII atoms are asymmetrically bridged by two chloride ions. Each CuII atom is also bound to the three N atoms of a deprotonated tridentate Schiff base ligand, giving a distorted square-pyramidal N3Cl2 coordination environment overall. The dinuclear complex lies across an inversion centre in the space group P\overline{1}. This work demonstrates the effect of ligand flexibility and steric constraints on the structures of copper(II) complexes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108028783/gd3235sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108028783/gd3235Isup2.hkl
Contains datablock I

CCDC reference: 707199

Comment top

In recent years, much attention has been paid to the complexes of a wide range of acyclic Schiff base ligands, in particular pyridine-containing systems. However, much less is known about complexes of the pyrrole analogues of such ligands, despite their potentially interesting similarities to porphyrins. Recently, our focus has been on the copper(II) chemistry of N3 tridentate Schiff base ligands, in particular mixed pyrrole–imine–pyridine ligands. Ligands L1-, L2- and L3-, the deprotonated forms of HL1, HL2 and HL3 {where HL1 is N-(1H-pyrrol-2-ylmethylene)-2-pyridineethanamine, HL2 is N-(1-(1H-pyrrol-2-yl)ethylidene)(pyridin-2-yl)methanamine and HL3 is N-[1-(1H-pyrrol-2-yl)ethylidene]-2-(pyridine-2-yl)ethanamine}, are of this type.

These ligands are closely related to pyridine–imine–pyridine ligands, which have been well studied (Arriortua et al., 1991; Cortés et al., 1992, 1995; Garland et al., 1996; Larramendi et al., 1991; Larramendi et al., 1992; Rojo et al., 1990). In our previous work using ligands L1- and L2-, monomeric, dimeric and one-dimensional chain polymeric copper(II) complexes have been synthesized (Li, Moubaraki et al., 2008; Li, Zhao et al., 2008), depending on the nature of the ligand and the choice of halide or pseudohalide coligand. Among these complexes, the dimeric and one-dimensional chain polymeric complexes exhibit weak antiferromagnetic exchange.

These examples, together with those obtained with the pyridine–imine–pyridine ligands mentioned above, indicate that the use of less flexible tridentate ligands tends to result in the formation of monomeric and dimeric complexes, while the use of more flexible tridentate ligands tends to give rise to dimeric or polymeric complexes. Ligand L3- is very closely related to L1- and L2-, with its flexibility being similar to that of L1- but greater than that of L2-. In addition, attachment of a methyl substituent to the C atom of the imino CN bond of L1-, which results in L3-, imposes some steric constraints on L3-. These differences in ligand flexibility and steric constraints are expected to influence the structural properties of the complexes of this ligand. The title compound, [Cu2(µ-Cl)2(L3)2], (I), has been prepared using L3- as the next example within the framework of our ongoing studies. We report here the crystal structure of (I) and compare it with those of the copper(II) complexes of ligands L1-, L2- and some other reported closely related tridentate ligands.

The asymmetric unit of (I) (Fig. 1) contains one-half of the neutral dimeric molecule; the other half is generated by a centre of inversion. The two CuII ions are asymmetrically bridged by two Cl- ions. Each Cu atom is also bound to the three N atoms (one deprotonated pyrrole N donor, one pyridine N donor and one imine N donor) of the tridentate ligand, L3-, giving an N3Cl2 coordination environment overall. The coordination geometry about each CuII ion can be described as a distorted square pyramid according to the τ value of 0.14 (Addison et al., 1984). The basal coordination sites are occupied by the three N atoms of L3- and one bridging Cl- ion, Cl1. The apical position is occupied by the second bridging Cl- ion, Cl1i [symmetry code: (i) -x + 1, -y, -z]. The apical Cu—Cl bond is significantly longer than the basal Cu—Cl bond (Table 1), a feature which appears frequently in square-pyramidal copper(II) complexes (Urtiaga et al., 1996; Rojo et al., 1987). The coordination mode and geometry about the CuII ions in (I) are very similar to those observed for the CuII ions in the analogous doubly halide-bridged dimers of ligand L1-, [Cu2(L1)2(µ-X)2] [X = Cl-, (II); X = Br-, (III)] (Li, Moubaraki et al., 2008). However, the low completeness of the dataset for complex (II) prevents detailed comparison of the geometric parameters between structures (I) and (II). On the other hand, the chloridocopper(II) complex of ligand L2- is a monomer, [Cu(L2)Cl], (IV), and the central CuII ion is bound to the three N atoms of L2- and to one Cl- ion in a square-planar N3Cl coordination (Li, Zhao et al., 2008). So the coordination mode and arrangement of donor atoms around the CuII centre in (IV) are different from those observed for the copper(II) dimers of L1- and L3-, (I)–(III).

Of the three basal Cu—N bond distances in (I), the shortest (Cu1—N1) occurs between the Cu atom and the deprotonated negatively charged pyrrole N atom and the longest (Cu1—N3) between the Cu atom and the pyridine N donor which is trans to the pyrrole N atom. This phenomenon was also seen in (II)–(IV). In the coordination polyhedron, the average value of the Cl(apical)—Cu1—atom(basal) angles is 96.0°, while the average value of the cis basal angles is 89.5°. The three Cu—N basal bond distances and one cis basal angle (N1—Cu1—N2) in (I) are very close to those in (III) and (IV). The other three cis basal angles in (I) are quite different from those in (IV), although they are very similar to the corresponding ones in (III). As expected, the cis basal angle N2—Cu1—N3 in (I) [90.17 (11)°] is much larger than that in (IV) [80.55 (9)°], since in (I) it forms in the six-membered pyridine–imine chelate, while in (IV) it forms in the five-membered pyridine–imine chelate. On the other hand, the two cis N—Cu—Cl basal angles in (I) are smaller than those in (IV). These bond distances and angles also compare well with the values reported for related copper(II) complexes (Bertrand & Kirkwood, 1972; Brooker & Carter, 1995; Colacio et al., 2000; Larramendi et al., 1991; Matsumoto et al., 1999). It is worth noting that the Cu—N3 distance lies at the high end of the literature values. This is probably because of the strong bond between the deprotonated negatively charged pyrrole N atom and the CuII atom.

The two basal planes, N1/N2/N3/Cl1 and N1i/N2i/N3i/Cl1i, are exactly parallel to each other, by symmetry, and the average distance between them is just 2.922 Å. The four basal atoms are closely coplanar, with a maximum deviation from the mean basal plane of only 0.0773 (14) Å observed for the imine atom N2. The Cu atom is located 0.2063 (13) Å out of the basal plane towards the apical ligand.

The bridging Cu2Cl2 core is exactly planar, due to the presence of the crystallographic inversion centre in the middle of the dimer, and is approximately rectangular with angles Cu1—Cl1—Cu1i = 90.85 (4)° and Cl1—Cu1—Cl1i = 89.15 (4)°. The same type of bridging Cu2X2 core was also found in (II) (X = Cl-) and (III) (X = Br-), as well as in [Cu2(apyhist)2(µ-Cl)2](ClO4)2 [apyhist = (4-imidazolyl)ethylene-2-amino-1-ethylpyridine], (V) (Alves et al., 2003), and [Cu2(terpy)2(µ-Cl)2](PF6)2 (terpy = 2,2':6',2''-terpyridine), (VI) (Rojo et al., 1987). These angles are close to the corresponding angles in (III) [Cu—Br—Cui = 88.23 (5)° and Br—Cu—Bri = 91.77 (5)°]. The Cu2Cl2 plane is nearly perpendicular to the basal N3Cl planes, with a dihedral angle of 87.40 (5)°, which is smaller than the corresponding angle in (III) [97.75 (6)°]. The intramolecular Cu···Cu separation is 3.5573 (14) Å, which is, as expected, shorter than in (III) [3.7721 (27) Å]. However, (I) has a slightly longer Cu···Cu separation compared with that in (V) [3.478 (1) Å] and (VI) [3.510 (14) Å]. This is presumably because (I) has a longer Cu—Cl(basal) bond distance and a larger Cu—Cl—Cui bond angle in comparison with the corresponding values in (V) [2.271 (1) Å and 87.46 (4)°] and (VI) [2.218 (19) Å and 89.9 (2)°].

Ligands L1-, L2- and L3- are very closely related to each other. However, complexation of them with CuCl2 gives two different structural types, monomer and dimer. Examination of these ligands shows that L1- and L3- have similar flexibility but both ligands are more flexible than L2-. Correspondingly, copper(II) dimers (I) and (II) formed with L3- and L1-, respectively, while the copper(II) monomer, (IV), was obtained with L2-. It is probably the reduced flexibility and greater steric constraint of L2- that results in the formation of such a monomer. In addition, comparison of (I) and (II) indicates that attachment of a bulky methyl substituent to the imino C atom of L1-, which gives L3- and imposes some steric constraints on L3-, makes (I) more distorted towards trigonal–bipyramidal than (II) [τ = 0.14 for (I) and nearly zero for (II)], although the imposed steric constrains have no influence on the dimerization of the [Cu(L3)Cl] unit to form the dimer (I), [Cu2(L3)2(µ-Cl)2]. However, the introduction of a bulky Br substituent at the β position on the pyrrole ring of L1- results in the formation of a singly bromide-bridged one-dimensional chain polymeric copper(II) complex (Li, Moubaraki et al., 2008).

Related literature top

For related literature, see: Addison et al. (1984); Alves et al. (2003); Arriortua et al. (1991); Bertrand & Kirkwood (1972); Brooker & Carter (1995); Colacio et al. (2000); Cortés et al. (1992, 1995); Garland et al. (1996); Larramendi et al. (1991, 1992); Li, Moubaraki, Murray & Brooker (2008); Li, Zhao, Tang & Tao (2008); Matsumoto et al. (1999); Rojo et al. (1987, 1990); Urtiaga et al. (1996).

Experimental top

Ligand HL3 was synthesized from the condensation of 2-acetylpyrrole with 2-(2-aminoethyl)pyridine. To a solution of HL3 (0.340 mmol) in methanol (5 ml) was added triethylamine (0.347 mmol) in methanol (5 ml). To the resulting solution was added a green solution of copper(II) chloride dihydrate (0.338 mmol) in methanol (5 ml), and a precipitate formed. The resulting mixture was stirred for 3.5 h, after which the solid was collected by filtration, washed with methanol and dried in vacuo (yield 0.083 g, 79% based on copper(II) chloride used). Single crystals of complex (I) suitable for X-ray determination were obtained by vapour diffusion of diethyl ether into a dichloromethane solution. Analysis, found: C 50.15, H 4.65, N 13.44%; calculated for C26H28N6Cu2Cl2: C 50.16, H 4.53, N, 13.50%.

Refinement top

H atoms were positioned geometrically and refined using a riding model, with C—H bonds = 0.93–0.98 Å, and with Uiso (H) = 1.2Ueq(C), or 1.5Ueq(C) for the methyl group.

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the title compound, with the atomic 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 + 1,-y,-z.]
Bis(µ2-chlorido)-bis{2-[1-(2-pyridylethylimino)ethyl]pyrrolato- κ3N,N',N''}dicopper(II) top
Crystal data top
[Cu2Cl2(C13H14N3)2]Z = 1
Mr = 622.54F(000) = 318
Triclinic, P1Dx = 1.643 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71070 Å
a = 8.122 (2) ÅCell parameters from 2087 reflections
b = 8.412 (3) Åθ = 3.2–25.3°
c = 9.240 (3) ŵ = 1.93 mm1
α = 91.973 (8)°T = 213 K
β = 93.386 (9)°Block, green-blue
γ = 92.464 (8)°0.42 × 0.20 × 0.05 mm
V = 629.2 (3) Å3
Data collection top
Rigaku Mercury CCD
diffractometer
2286 independent reflections
Radiation source: fine-focus sealed tube1939 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 7.31 pixels mm-1θmax = 25.3°, θmin = 3.2°
ω scansh = 99
Absorption correction: multi-scan
(Jacobson, 1998)
k = 910
Tmin = 0.531, Tmax = 0.908l = 1111
6145 measured reflections
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0281P)2 + 0.5114P]
where P = (Fo2 + 2Fc2)/3
2286 reflections(Δ/σ)max < 0.001
165 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
[Cu2Cl2(C13H14N3)2]γ = 92.464 (8)°
Mr = 622.54V = 629.2 (3) Å3
Triclinic, P1Z = 1
a = 8.122 (2) ÅMo Kα radiation
b = 8.412 (3) ŵ = 1.93 mm1
c = 9.240 (3) ÅT = 213 K
α = 91.973 (8)°0.42 × 0.20 × 0.05 mm
β = 93.386 (9)°
Data collection top
Rigaku Mercury CCD
diffractometer
2286 independent reflections
Absorption correction: multi-scan
(Jacobson, 1998)
1939 reflections with I > 2σ(I)
Tmin = 0.531, Tmax = 0.908Rint = 0.036
6145 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.085H-atom parameters constrained
S = 1.13Δρmax = 0.53 e Å3
2286 reflectionsΔρmin = 0.35 e Å3
165 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
Cu10.47083 (5)0.02517 (5)0.18855 (4)0.02431 (15)
Cl10.67831 (10)0.11924 (10)0.04848 (9)0.0263 (2)
N10.6040 (3)0.1449 (3)0.2636 (3)0.0252 (7)
N20.3179 (3)0.0567 (3)0.3349 (3)0.0228 (6)
N30.3426 (3)0.2280 (3)0.1740 (3)0.0242 (6)
C10.7456 (4)0.2176 (4)0.2406 (4)0.0296 (8)
H10.81600.19300.16650.036*
C20.7729 (5)0.3335 (4)0.3409 (4)0.0334 (9)
H20.86290.40010.34700.040*
C30.6419 (5)0.3322 (4)0.4309 (4)0.0309 (9)
H30.62570.39770.50970.037*
C40.5394 (4)0.2152 (4)0.3813 (4)0.0232 (8)
C50.3788 (4)0.1650 (4)0.4159 (4)0.0251 (8)
C60.1539 (4)0.0004 (4)0.3542 (4)0.0319 (9)
H6A0.15830.07930.43430.038*
H6B0.07980.08930.37820.038*
C70.0886 (4)0.0727 (4)0.2152 (4)0.0294 (8)
H7A0.09990.00260.13350.035*
H7B0.02930.09060.22180.035*
C80.1770 (4)0.2272 (4)0.1861 (4)0.0275 (8)
C90.0917 (5)0.3663 (5)0.1745 (4)0.0383 (10)
H90.02340.36310.18110.046*
C100.1749 (5)0.5083 (5)0.1534 (4)0.0415 (10)
H100.11740.60250.14510.050*
C110.3434 (5)0.5108 (4)0.1447 (4)0.0336 (9)
H110.40400.60660.13260.040*
C120.4205 (5)0.3698 (4)0.1542 (4)0.0283 (8)
H120.53540.37180.14640.034*
C130.2892 (5)0.2385 (5)0.5360 (4)0.0347 (9)
H13A0.25850.15540.60340.052*
H13B0.36050.31060.58670.052*
H13C0.19050.29700.49570.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0218 (2)0.0254 (3)0.0263 (3)0.00143 (17)0.00315 (18)0.00524 (18)
Cl10.0213 (4)0.0301 (5)0.0277 (5)0.0012 (4)0.0033 (4)0.0043 (4)
N10.0226 (16)0.0242 (16)0.0293 (17)0.0005 (12)0.0037 (13)0.0046 (12)
N20.0251 (15)0.0206 (15)0.0230 (16)0.0020 (12)0.0038 (13)0.0012 (12)
N30.0252 (16)0.0260 (16)0.0214 (15)0.0014 (13)0.0004 (13)0.0039 (12)
C10.026 (2)0.027 (2)0.036 (2)0.0001 (16)0.0038 (17)0.0008 (16)
C20.028 (2)0.029 (2)0.044 (2)0.0067 (16)0.0006 (18)0.0033 (17)
C30.038 (2)0.026 (2)0.029 (2)0.0011 (16)0.0016 (17)0.0046 (15)
C40.0278 (19)0.0218 (18)0.0196 (18)0.0015 (15)0.0003 (15)0.0021 (14)
C50.030 (2)0.0237 (18)0.0208 (18)0.0061 (15)0.0019 (16)0.0018 (14)
C60.025 (2)0.033 (2)0.039 (2)0.0004 (16)0.0056 (17)0.0033 (17)
C70.0206 (19)0.035 (2)0.032 (2)0.0020 (16)0.0021 (16)0.0001 (16)
C80.0247 (19)0.035 (2)0.0232 (19)0.0032 (16)0.0012 (16)0.0003 (15)
C90.029 (2)0.043 (3)0.044 (2)0.0130 (19)0.0019 (19)0.0046 (19)
C100.052 (3)0.030 (2)0.043 (2)0.015 (2)0.001 (2)0.0021 (18)
C110.052 (3)0.025 (2)0.025 (2)0.0031 (18)0.0066 (19)0.0057 (15)
C120.033 (2)0.029 (2)0.0227 (19)0.0005 (17)0.0020 (16)0.0018 (15)
C130.040 (2)0.038 (2)0.027 (2)0.0008 (18)0.0084 (18)0.0097 (17)
Geometric parameters (Å, º) top
Cu1—N11.952 (3)C5—C131.499 (5)
Cu1—N22.009 (3)C6—C71.520 (5)
Cu1—N32.041 (3)C6—H6A0.9800
Cu1—Cl12.3139 (10)C6—H6B0.9800
Cu1—Cl1i2.6676 (11)C7—C81.498 (5)
Cl1—Cu1i2.6676 (11)C7—H7A0.9800
N1—C11.350 (4)C7—H7B0.9800
N1—C41.375 (4)C8—C91.389 (5)
N2—C51.295 (4)C9—C101.372 (6)
N2—C61.451 (4)C9—H90.9400
N3—C121.349 (4)C10—C111.376 (6)
N3—C81.356 (4)C10—H100.9400
C1—C21.384 (5)C11—C121.368 (5)
C1—H10.9400C11—H110.9400
C2—C31.389 (5)C12—H120.9400
C2—H20.9400C13—H13A0.9700
C3—C41.388 (5)C13—H13B0.9700
C3—H30.9400C13—H13C0.9700
C4—C51.439 (5)
N1—Cu1—N281.45 (11)C4—C5—C13121.0 (3)
N1—Cu1—N3162.52 (11)N2—C6—C7109.5 (3)
N2—Cu1—N390.17 (11)N2—C6—H6A109.8
N1—Cu1—Cl192.66 (9)C7—C6—H6A109.8
N2—Cu1—Cl1171.19 (8)N2—C6—H6B109.8
N3—Cu1—Cl193.70 (8)C7—C6—H6B109.8
N1—Cu1—Cl1i101.06 (9)H6A—C6—H6B108.2
N2—Cu1—Cl1i98.38 (8)C8—C7—C6112.8 (3)
N3—Cu1—Cl1i95.30 (8)C8—C7—H7A109.0
Cl1—Cu1—Cl1i89.15 (4)C6—C7—H7A109.0
Cu1—Cl1—Cu1i90.85 (4)C8—C7—H7B109.0
C1—N1—C4106.2 (3)C6—C7—H7B109.0
C1—N1—Cu1140.7 (2)H7A—C7—H7B107.8
C4—N1—Cu1113.0 (2)N3—C8—C9121.0 (3)
C5—N2—C6121.2 (3)N3—C8—C7118.2 (3)
C5—N2—Cu1114.2 (2)C9—C8—C7120.8 (3)
C6—N2—Cu1124.6 (2)C10—C9—C8120.3 (4)
C12—N3—C8117.1 (3)C10—C9—H9119.9
C12—N3—Cu1121.0 (2)C8—C9—H9119.9
C8—N3—Cu1121.9 (2)C9—C10—C11119.0 (3)
N1—C1—C2110.7 (3)C9—C10—H10120.5
N1—C1—H1124.7C11—C10—H10120.5
C2—C1—H1124.7C12—C11—C10118.1 (4)
C1—C2—C3106.8 (3)C12—C11—H11120.9
C1—C2—H2126.6C10—C11—H11120.9
C3—C2—H2126.6N3—C12—C11124.4 (3)
C4—C3—C2106.4 (3)N3—C12—H12117.8
C4—C3—H3126.8C11—C12—H12117.8
C2—C3—H3126.8C5—C13—H13A109.5
N1—C4—C3109.9 (3)C5—C13—H13B109.5
N1—C4—C5115.2 (3)H13A—C13—H13B109.5
C3—C4—C5134.6 (3)C5—C13—H13C109.5
N2—C5—C4115.6 (3)H13A—C13—H13C109.5
N2—C5—C13123.4 (3)H13B—C13—H13C109.5
N1—Cu1—Cl1—Cu1i101.03 (9)Cu1—N1—C4—C3178.7 (2)
N3—Cu1—Cl1—Cu1i95.26 (8)C1—N1—C4—C5174.3 (3)
Cl1i—Cu1—Cl1—Cu1i0.0Cu1—N1—C4—C57.1 (4)
N2—Cu1—N1—C1175.1 (4)C2—C3—C4—N10.0 (4)
N3—Cu1—N1—C1122.7 (4)C2—C3—C4—C5172.7 (4)
Cl1—Cu1—N1—C111.5 (4)C6—N2—C5—C4177.3 (3)
Cl1i—Cu1—N1—C178.2 (4)Cu1—N2—C5—C43.9 (4)
N2—Cu1—N1—C47.0 (2)C6—N2—C5—C131.2 (5)
N3—Cu1—N1—C455.1 (5)Cu1—N2—C5—C13177.6 (3)
Cl1—Cu1—N1—C4166.4 (2)N1—C4—C5—N22.0 (4)
Cl1i—Cu1—N1—C4104.0 (2)C3—C4—C5—N2174.4 (4)
N1—Cu1—N2—C56.1 (2)N1—C4—C5—C13176.4 (3)
N3—Cu1—N2—C5158.5 (2)C3—C4—C5—C134.1 (6)
Cl1i—Cu1—N2—C5106.1 (2)C5—N2—C6—C7158.0 (3)
N1—Cu1—N2—C6175.2 (3)Cu1—N2—C6—C723.3 (4)
N3—Cu1—N2—C620.2 (3)N2—C6—C7—C870.1 (4)
Cl1i—Cu1—N2—C675.1 (3)C12—N3—C8—C91.7 (5)
N1—Cu1—N3—C1283.5 (5)Cu1—N3—C8—C9179.4 (3)
N2—Cu1—N3—C12144.5 (3)C12—N3—C8—C7177.1 (3)
Cl1—Cu1—N3—C1227.6 (2)Cu1—N3—C8—C71.7 (4)
Cl1i—Cu1—N3—C12117.1 (2)C6—C7—C8—N358.4 (4)
N1—Cu1—N3—C895.3 (4)C6—C7—C8—C9120.5 (4)
N2—Cu1—N3—C834.3 (3)N3—C8—C9—C101.4 (6)
Cl1—Cu1—N3—C8153.6 (2)C7—C8—C9—C10177.5 (4)
Cl1i—Cu1—N3—C864.1 (3)C8—C9—C10—C110.3 (6)
C4—N1—C1—C20.2 (4)C9—C10—C11—C121.5 (6)
Cu1—N1—C1—C2178.1 (3)C8—N3—C12—C110.5 (5)
N1—C1—C2—C30.1 (4)Cu1—N3—C12—C11179.4 (3)
C1—C2—C3—C40.1 (4)C10—C11—C12—N31.1 (6)
C1—N1—C4—C30.1 (4)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···Cl1i0.982.733.559 (4)143
C7—H7B···Cl1ii0.982.813.630 (4)142
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.

Experimental details

Crystal data
Chemical formula[Cu2Cl2(C13H14N3)2]
Mr622.54
Crystal system, space groupTriclinic, P1
Temperature (K)213
a, b, c (Å)8.122 (2), 8.412 (3), 9.240 (3)
α, β, γ (°)91.973 (8), 93.386 (9), 92.464 (8)
V3)629.2 (3)
Z1
Radiation typeMo Kα
µ (mm1)1.93
Crystal size (mm)0.42 × 0.20 × 0.05
Data collection
DiffractometerRigaku Mercury CCD
diffractometer
Absorption correctionMulti-scan
(Jacobson, 1998)
Tmin, Tmax0.531, 0.908
No. of measured, independent and
observed [I > 2σ(I)] reflections
6145, 2286, 1939
Rint0.036
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.085, 1.13
No. of reflections2286
No. of parameters165
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.35

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2001), CrystalStructure (Molecular Structure Corporation & Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Selected bond lengths (Å) top
Cu1—N11.952 (3)Cu1—Cl12.3139 (10)
Cu1—N22.009 (3)Cu1—Cl1i2.6676 (11)
Cu1—N32.041 (3)
Symmetry code: (i) x+1, y, z.
 

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