Dichlorido-1κCl,3κCl-bis­{μ-2,2′-[pro­pane-1,3-diylbis(imino­methyl­ene)]di­phenol­ato}-1:2κ6O,N,N′,O′:O,O′;2:3κ6O,O′:O,N,N′,O′-tricopper(II)

Ateş, B.M.; Ercan, F.; Svoboda, I.; Fuess, H.; Atakol, O.

doi:10.1107/S1600536808003048

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Pages m481-m482

doi:10.1107/S1600536808003048

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Dichlorido-1κCl,3κCl-bis{μ-2,2′-[propane-1,3-diylbis(iminomethylene)]diphenolato}-1:2κ⁶O,N,N′,O′:O,O′;2:3κ⁶O,O′:O,N,N′,O′-tricopper(II)

Bürke Meltem Ateş,^a Filiz Ercan,^a Ingrid Svoboda,^b Hartmut Fuess ^b and Orhan Atakol ^c ^*

^aDepartment of Engineering Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey, ^bDarmstadt University of Technology, Institute of Materials Science, Petersenstrasse 23, D-64287 Darmstadt, Germany, and ^cDepartment of Chemistry, Ankara University Science Faculty, 06100 Ankara, Turkey
^*Correspondence e-mail: burke.ates@taek.gov.tr

(Received 27 November 2007; accepted 28 January 2008; online 15 February 2008)

The title linear trinuclear copper(II) complex, [Cu₃(C₁₇H₂₀N₂O₂)₂Cl₂], was obtained from N,N′-bis(2-hydroxybenzyl)-1,3-propanediamine and CuCl₂. The overall charge of the three Cu²⁺ ions is balanced by four deprotonated phenol groups and two Cl⁻ ligands. The complex is centrosymmetric with the central Cu²⁺ occupying a special position ( $[\overline{1}]$ ). This Cu²⁺ ion is coordinated by the four phenolate O atoms in a square-planar fashion. The second Cu²⁺ occupies a general position in a square-pyramidal fashion. Two phenolate O atoms and two amine N form the basal plane, with Cl⁻ ligands occupying the fifth coordination site.

Related literature

For related literature, see: Addison et al. (1984 ); Atakol et al. (1999 ); Cremer & Pople (1975 ); Ercan et al. (2002 ); Fukuhara et al. (1990 ); Gerli et al. (1991 ); Mikuriya et al. (2001 ); Song et al. (2003 , 2005 ); Spek (2003 ); Uhlenbrock et al. (1996 ); Yıldırım & Atakol (2002 ).

Experimental

Crystal data

[Cu₃(C₁₇H₂₀N₂O₂)₂Cl₂]
M_r = 830.25
Monoclinic, P 2₁ /c
a = 11.0189 (7) Å
b = 15.3861 (8) Å
c = 10.7441 (8) Å
β = 106.959 (7)°
V = 1742.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.01 mm⁻¹
T = 100 (2) K
0.36 × 0.22 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2002 $[Oxford Diffraction (2002). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Poland.]$ ) T_min = 0.531, T_max = 0.766
12067 measured reflections
3481 independent reflections
2969 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.075
S = 1.10
3481 reflections
220 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu2—Cl1	2.5092 (7)
Cu2—Cu1	2.9138 (3)
O1—Cu1	1.9191 (15)
O1—Cu2	1.9825 (16)
O2—Cu1	1.9108 (16)
O2—Cu2	1.9632 (16)
N1—Cu2	1.995 (2)
N2—Cu2	1.995 (2)

O2—Cu1—O1	80.93 (7)
O2—Cu1—Cu2	41.91 (5)
O1—Cu1—Cu2	42.52 (5)
O2—Cu2—O1	78.09 (7)
O2—Cu2—N1	163.99 (8)
O1—Cu2—N1	92.91 (7)
O2—Cu2—N2	93.17 (7)
O1—Cu2—N2	168.74 (8)
O2—Cu2—Cl1	89.92 (5)
O1—Cu2—Cl1	88.09 (5)
Cu1—O1—Cu2	96.62 (7)
Cu1—O2—Cu2	97.54 (7)

Data collection: CrysAlis CCD (Oxford Diffraction, 2002 $[Oxford Diffraction (2002). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Poland.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2002 $[Oxford Diffraction (2002). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Poland.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003048/fi2056sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003048/fi2056Isup2.hkl

checkCIF report

Comment top

Bis-N,N'-bis(2-hydroxybenzyl)-1,3-propane-diamine is an ONNO type Schiff base and there have been various polynuclear complexes synthesized since 1990 (Fukuhara et al., 1990; Gerli et al., 1991; Uhlenbrock et al., 1996, Mikuriya et al., 2001).

In this study, N,N'-bis(salicylidene)-1,3-propane-diamine was reduced into a symmetrical phenol-amine compound by the help of NaBH₄. A trinuclear Cu(II) complex was prepared by the reaction of the ligand obtained with CuCl₂ and its molecular structure was determined. Previously, this complex had been prepared in MeOH solution and crystallized in its tetra-solvated form (Song et al., 2005). The trinuclear complex obtained in this structure is not solvated and has different crystallographic details.

As can seen from PLATON (Spek, 2003), the terminal Cu(II) ion has a square pyramidal coordination formed by the two phenolic oxygen and two iminic nitrogen atoms of the ligand and a chloride ion. There has been a T factor defined for five membered coordination sphere (Addison et al., 1984). This factor is given as T=a-b/60, where a and b correspond to two largest angles around the metal atom. If T=0 the coordination is an ideal square pyramid and if T=1 the coordination is ideal trigonal bipyramid. If the values listed in molecular geometry are employed the T value is found as 0.078 indicating that the terminal Cu(II) atoms has a near ideal square pyramidal symmetry. The Cu—Cl bond is longer than other coordination bonds (2.509 Å). The bond length in the square base are very close to each other (1.963 Å). The chalate ring (Cu2, N1, N2, C8, C9, C10) formed by the terminal Cu(II) ions has an almost ideal chair conformation. The conformation of the ring was analysed using PLATON. The Cremer-Pople puckering parameters are Q_T=1.374 (6), θ=-38.9 (2), ϕ=120.34 (12)° (Cremer et al., 1975).

The central Cu(II) ion is coordinated between four phenolic oxygen donors. The Cu1—O2 and Cu1—O1 distances are 1.911 Å and 1.919 Å, respectively. The phenolic O atoms act as bridging ligands between the central and the terminal Cu ions. The distance between Cu2 and an L.S. plane through O1, N1, N2 and O2 is 0.1894 (3) Å.. That is why the six membered chelate ring conformation of Schiff base complexes was reported as almost ideal (Yıldırım et al., 2002). The smallest Cu—Cu distance determined in similar complexes was reported as 2.914 Å (Song et al., 2005; Song et al., 2003). The Cu2—Cu1 distance in the title compound is 2.9138 (3) Å and thus close to the shortest reported distances. In complexes containing m-bonds such as AcO– and HCOO– this distance is bigger than 3.0 Å (Ercan et al., 2002; Atakol et al., 1999).

Related literature top

For related literature, see: Addison et al. (1984); Atakol et al. (1999); Cremer & Pople (1975); Ercan et al. (2002); Fukuhara et al. (1990); Gerli et al. (1991); Mikuriya et al. (2001); Song et al. (2003, 2005); Spek (2003); Uhlenbrock et al. (1996); Yıldırım & Atakol (2002).

Experimental top

N,N'-bis(salicylidene)-1,3-propane-diamine was dissolved by slightly heating in MeOH (80 ml). NaBH₄ was added into this solution in its solid form with small portions and the resulting mixture was rigorously stirred. The addition of NaBH₄ was continued unless the solution became completely colorless. The colorless solution was mixed with ice (300 g) and kept on the bench for 24 h. The white precipitate was the reduced product of N,N'-bis(2-hydroxybenzyl)-1,3-propane-diamine (m.p. 379–380 K, yield % 87, the N—H streching band is observed at 3273 cm^-1). N,N'-bis (2-hydroxybenzyl)-1,3-propane-diamine (0.285 g, 1 mmole) was dissolved in dmf (dimethyl-formamide)(20 ml) by heating and a solution of CuCl₂.2H₂O (0.255 g, 1.5 mmole) in hot dmf (20 ml) was added to it and the resulting mixture was kept on the bench for 4–5 d. The resulting crystals were filtered off, washed with EtOH and dried in oven at 353 K.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED (Oxford Diffraction, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level [symmetry code: (i) -x, -y, 1 - z].

Dichlorido-1κCl,3κCl-bis{µ-2,2'-[propane-1,3- diylbis(iminomethylene)]diphenolato}- 1:2κ⁶O,N,N',O':O,O';2:3κ⁶O,O':O,N,N',O'-tricopper(II) top

Crystal data top

[Cu₃(C₁₇H₂₀N₂O₂)₂Cl₂]	F(000) = 850
M_r = 830.25	D_x = 1.583 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4076 reflections
a = 11.0189 (7) Å	θ = 2.4–26.4°
b = 15.3861 (8) Å	µ = 2.01 mm⁻¹
c = 10.7441 (8) Å	T = 100 K
β = 106.959 (7)°	Prism, dark green
V = 1742.3 (2) Å³	0.36 × 0.22 × 0.14 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur diffractometer	3481 independent reflections
Radiation source: fine-focus sealed tube	2969 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 26.4°, θ_min = 4.1°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2002)	h = −13→13
T_min = 0.531, T_max = 0.766	k = −18→18
12067 measured reflections	l = −7→13

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0379P)² + 1.1376P] where P = (F_o² + 2F_c²)/3
3481 reflections	(Δ/σ)_max = 0.019
220 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Cu₃(C₁₇H₂₀N₂O₂)₂Cl₂]	V = 1742.3 (2) Å³
M_r = 830.25	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0189 (7) Å	µ = 2.01 mm⁻¹
b = 15.3861 (8) Å	T = 100 K
c = 10.7441 (8) Å	0.36 × 0.22 × 0.14 mm
β = 106.959 (7)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	3481 independent reflections
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2002)	2969 reflections with I > 2σ(I)
T_min = 0.531, T_max = 0.766	R_int = 0.025
12067 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.57 e Å⁻³
3481 reflections	Δρ_min = −0.32 e Å⁻³
220 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

	x	y	z	U_iso*/U_eq
Cu1	0.0000	0.0000	0.5000	0.01443 (11)
Cu2	0.02986 (3)	0.187585 (17)	0.48593 (3)	0.01380 (10)
Cl1	0.04255 (6)	0.16106 (4)	0.71982 (6)	0.02363 (16)
O1	−0.10643 (15)	0.09894 (10)	0.43769 (17)	0.0170 (4)
O2	0.12675 (15)	0.08066 (10)	0.48475 (17)	0.0187 (4)
N1	−0.09257 (18)	0.28603 (13)	0.4363 (2)	0.0153 (4)
H1A	−0.080 (3)	0.3050 (19)	0.369 (3)	0.028*
N2	0.18192 (18)	0.26353 (13)	0.5115 (2)	0.0158 (4)
H2A	0.180 (3)	0.2855 (19)	0.437 (3)	0.028*
C1	−0.2034 (2)	0.10818 (15)	0.3275 (2)	0.0153 (5)
C2	−0.2429 (2)	0.04128 (16)	0.2376 (2)	0.0185 (5)
H2	−0.2027	−0.0139	0.2531	0.022*
C3	−0.3414 (2)	0.05583 (17)	0.1253 (3)	0.0214 (5)
H3	−0.3684	0.0102	0.0639	0.026*
C4	−0.4010 (2)	0.13600 (17)	0.1012 (3)	0.0222 (6)
H4	−0.4680	0.1455	0.0236	0.027*
C5	−0.3617 (2)	0.20233 (16)	0.1919 (2)	0.0198 (5)
H5	−0.4021	0.2574	0.1753	0.024*
C6	−0.2644 (2)	0.18960 (15)	0.3063 (2)	0.0159 (5)
C7	−0.2269 (2)	0.25755 (16)	0.4097 (2)	0.0188 (5)
H7A	−0.2831	0.3086	0.3828	0.023*
H7B	−0.2396	0.2344	0.4910	0.023*
C8	−0.0623 (2)	0.35758 (15)	0.5329 (3)	0.0202 (5)
H8A	−0.0640	0.3349	0.6186	0.024*
H8B	−0.1282	0.4031	0.5063	0.024*
C9	0.0669 (2)	0.39773 (15)	0.5461 (3)	0.0216 (6)
H9A	0.0678	0.4190	0.4594	0.026*
H9B	0.0771	0.4489	0.6041	0.026*
C10	0.1804 (2)	0.33853 (16)	0.5985 (3)	0.0208 (5)
H10A	0.2590	0.3728	0.6105	0.025*
H10B	0.1798	0.3163	0.6848	0.025*
C11	0.3017 (2)	0.21331 (16)	0.5631 (2)	0.0191 (5)
H11A	0.3026	0.1874	0.6477	0.023*
H11B	0.3744	0.2539	0.5792	0.023*
C12	0.3198 (2)	0.14203 (15)	0.4743 (2)	0.0160 (5)
C13	0.4258 (2)	0.13781 (16)	0.4284 (2)	0.0198 (5)
H13	0.4855	0.1840	0.4470	0.024*
C14	0.4451 (2)	0.06791 (17)	0.3567 (3)	0.0226 (6)
H14	0.5182	0.0658	0.3268	0.027*
C15	0.3588 (2)	0.00111 (16)	0.3285 (2)	0.0205 (5)
H15	0.3731	−0.0473	0.2797	0.025*
C16	0.2508 (2)	0.00332 (15)	0.3702 (2)	0.0178 (5)
H16	0.1911	−0.0429	0.3494	0.021*
C17	0.2309 (2)	0.07401 (15)	0.4429 (2)	0.0152 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0114 (2)	0.0123 (2)	0.0181 (2)	−0.00059 (15)	0.00195 (17)	0.00469 (16)
Cu2	0.01222 (16)	0.01216 (15)	0.01634 (17)	0.00004 (10)	0.00307 (12)	0.00049 (11)
Cl1	0.0282 (3)	0.0268 (3)	0.0169 (3)	0.0022 (3)	0.0081 (3)	0.0001 (3)
O1	0.0138 (8)	0.0133 (8)	0.0197 (9)	−0.0007 (6)	−0.0016 (7)	0.0035 (7)
O2	0.0151 (9)	0.0141 (8)	0.0297 (10)	−0.0003 (6)	0.0110 (8)	0.0025 (7)
N1	0.0147 (10)	0.0151 (10)	0.0164 (11)	−0.0005 (8)	0.0049 (9)	0.0001 (8)
N2	0.0157 (10)	0.0145 (10)	0.0157 (11)	−0.0019 (8)	0.0022 (9)	−0.0001 (9)
C1	0.0096 (11)	0.0198 (12)	0.0169 (13)	−0.0009 (9)	0.0047 (10)	0.0066 (10)
C2	0.0146 (12)	0.0189 (12)	0.0228 (13)	−0.0008 (9)	0.0067 (10)	0.0034 (11)
C3	0.0182 (12)	0.0244 (13)	0.0213 (14)	−0.0060 (10)	0.0053 (11)	−0.0019 (11)
C4	0.0167 (12)	0.0304 (15)	0.0182 (14)	−0.0028 (10)	0.0030 (11)	0.0053 (11)
C5	0.0132 (12)	0.0218 (13)	0.0246 (14)	0.0018 (9)	0.0057 (11)	0.0070 (11)
C6	0.0104 (11)	0.0176 (12)	0.0213 (13)	−0.0012 (9)	0.0072 (10)	0.0029 (10)
C7	0.0129 (11)	0.0194 (12)	0.0254 (14)	0.0031 (9)	0.0075 (11)	0.0021 (11)
C8	0.0238 (13)	0.0155 (12)	0.0207 (14)	0.0045 (10)	0.0053 (11)	−0.0033 (10)
C9	0.0266 (14)	0.0148 (12)	0.0228 (14)	0.0011 (10)	0.0061 (12)	−0.0037 (10)
C10	0.0210 (13)	0.0153 (12)	0.0233 (14)	−0.0041 (10)	0.0020 (11)	−0.0055 (11)
C11	0.0133 (12)	0.0212 (12)	0.0209 (14)	−0.0010 (9)	0.0019 (10)	0.0012 (10)
C12	0.0138 (11)	0.0181 (12)	0.0140 (12)	0.0012 (9)	0.0010 (10)	0.0034 (10)
C13	0.0136 (12)	0.0247 (14)	0.0198 (13)	−0.0014 (10)	0.0028 (10)	0.0046 (11)
C14	0.0167 (12)	0.0313 (14)	0.0222 (14)	0.0048 (11)	0.0094 (11)	0.0085 (12)
C15	0.0239 (13)	0.0205 (13)	0.0177 (13)	0.0079 (10)	0.0067 (11)	0.0023 (10)
C16	0.0170 (12)	0.0169 (12)	0.0178 (13)	0.0004 (9)	0.0026 (10)	0.0036 (10)
C17	0.0125 (11)	0.0185 (12)	0.0139 (12)	0.0023 (9)	0.0027 (10)	0.0060 (10)

Geometric parameters (Å, º) top

Cu2—Cl1	2.5092 (7)	C7—H7B	0.9900
Cu2—Cu1	2.9138 (3)	C8—N1	1.483 (3)
Cu1—O2ⁱ	1.9108 (16)	C8—C9	1.520 (4)
Cu1—O1ⁱ	1.9191 (15)	C8—H8A	0.9900
Cu1—Cu2ⁱ	2.9138 (3)	C8—H8B	0.9900
O1—Cu1	1.9191 (15)	C9—C10	1.517 (3)
O1—Cu2	1.9825 (16)	C9—H9A	0.9900
O2—Cu1	1.9108 (16)	C9—H9B	0.9900
O2—Cu2	1.9632 (16)	C10—N2	1.488 (3)
N1—Cu2	1.995 (2)	C10—H10A	0.9900
N1—H1A	0.82 (3)	C10—H10B	0.9900
N2—Cu2	1.995 (2)	C11—N2	1.490 (3)
N2—H2A	0.86 (3)	C11—C12	1.505 (3)
C1—O1	1.351 (3)	C11—H11A	0.9900
C1—C2	1.392 (3)	C11—H11B	0.9900
C1—C6	1.408 (3)	C12—C13	1.394 (3)
C2—C3	1.386 (3)	C12—C17	1.406 (3)
C2—H2	0.9500	C13—C14	1.376 (4)
C3—C4	1.386 (4)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.373 (4)
C4—C5	1.390 (4)	C14—H14	0.9500
C4—H4	0.9500	C15—C16	1.389 (3)
C5—C6	1.389 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—C17	1.393 (3)
C6—C7	1.493 (3)	C16—H16	0.9500
C7—N1	1.489 (3)	C17—O2	1.353 (3)
C7—H7A	0.9900

O2—Cu1—O2ⁱ	180.00 (10)	C3—C4—C5	119.2 (2)
O2—Cu1—O1	80.93 (7)	C3—C4—H4	120.4
O2ⁱ—Cu1—O1	99.07 (7)	C5—C4—H4	120.4
O2—Cu1—O1ⁱ	99.07 (7)	C6—C5—C4	121.3 (2)
O2ⁱ—Cu1—O1ⁱ	80.93 (7)	C6—C5—H5	119.4
O1—Cu1—O1ⁱ	180.0	C4—C5—H5	119.4
O2—Cu1—Cu2	41.91 (5)	C5—C6—C1	118.5 (2)
O2ⁱ—Cu1—Cu2	138.09 (5)	C5—C6—C7	122.3 (2)
O1—Cu1—Cu2	42.52 (5)	C1—C6—C7	119.1 (2)
O1ⁱ—Cu1—Cu2	137.48 (5)	N1—C7—C6	113.15 (19)
O2—Cu1—Cu2ⁱ	138.09 (5)	N1—C7—H7A	108.9
O2ⁱ—Cu1—Cu2ⁱ	41.91 (5)	C6—C7—H7A	108.9
O1—Cu1—Cu2ⁱ	137.48 (5)	N1—C7—H7B	109.0
O1ⁱ—Cu1—Cu2ⁱ	42.52 (5)	C6—C7—H7B	108.9
Cu2—Cu1—Cu2ⁱ	180.000 (11)	H7A—C7—H7B	107.8
O2—Cu2—O1	78.09 (7)	N1—C8—C9	112.4 (2)
O2—Cu2—N1	163.99 (8)	N1—C8—H8A	109.1
O1—Cu2—N1	92.91 (7)	C9—C8—H8A	109.1
O2—Cu2—N2	93.17 (7)	N1—C8—H8B	109.1
O1—Cu2—N2	168.74 (8)	C9—C8—H8B	109.1
N1—Cu2—N2	93.87 (8)	H8A—C8—H8B	107.9
O2—Cu2—Cl1	89.92 (5)	C10—C9—C8	116.0 (2)
O1—Cu2—Cl1	88.09 (5)	C10—C9—H9A	108.3
N1—Cu2—Cl1	103.12 (6)	C8—C9—H9A	108.3
N2—Cu2—Cl1	99.10 (6)	C10—C9—H9B	108.3
O2—Cu2—Cu1	40.55 (5)	C8—C9—H9B	108.3
O1—Cu2—Cu1	40.86 (4)	H9A—C9—H9B	107.4
N1—Cu2—Cu1	133.49 (6)	N2—C10—C9	113.1 (2)
N2—Cu2—Cu1	132.54 (6)	N2—C10—H10A	109.0
Cl1—Cu2—Cu1	76.178 (16)	C9—C10—H10A	109.0
C1—O1—Cu1	129.48 (14)	N2—C10—H10B	109.0
C1—O1—Cu2	120.13 (13)	C9—C10—H10B	109.0
Cu1—O1—Cu2	96.62 (7)	H10A—C10—H10B	107.8
C17—O2—Cu1	133.74 (15)	N2—C11—C12	114.1 (2)
C17—O2—Cu2	125.53 (14)	N2—C11—H11A	108.7
Cu1—O2—Cu2	97.54 (7)	C12—C11—H11A	108.7
C8—N1—C7	111.16 (19)	N2—C11—H11B	108.7
C8—N1—Cu2	112.34 (15)	C12—C11—H11B	108.7
C7—N1—Cu2	112.63 (15)	H11A—C11—H11B	107.6
C8—N1—H1A	107 (2)	C13—C12—C17	118.5 (2)
C7—N1—H1A	110 (2)	C13—C12—C11	122.5 (2)
Cu2—N1—H1A	103 (2)	C17—C12—C11	118.8 (2)
C10—N2—C11	109.87 (19)	C14—C13—C12	121.1 (2)
C10—N2—Cu2	112.19 (15)	C14—C13—H13	119.4
C11—N2—Cu2	111.40 (15)	C12—C13—H13	119.4
C10—N2—H2A	106.1 (19)	C15—C14—C13	119.9 (2)
C11—N2—H2A	109.0 (19)	C15—C14—H14	120.1
Cu2—N2—H2A	108 (2)	C13—C14—H14	120.1
O1—C1—C2	122.5 (2)	C14—C15—C16	120.9 (2)
O1—C1—C6	117.0 (2)	C14—C15—H15	119.5
C2—C1—C6	120.5 (2)	C16—C15—H15	119.5
C3—C2—C1	119.5 (2)	C15—C16—C17	119.3 (2)
C3—C2—H2	120.3	C15—C16—H16	120.3
C1—C2—H2	120.3	C17—C16—H16	120.3
C2—C3—C4	121.0 (2)	O2—C17—C16	122.2 (2)
C2—C3—H3	119.5	O2—C17—C12	117.6 (2)
C4—C3—H3	119.5	C16—C17—C12	120.2 (2)

O1—C1—C2—C3	−178.7 (2)	C1—O1—Cu2—N2	−84.8 (4)
C6—C1—C2—C3	1.3 (3)	Cu1—O1—Cu2—N2	59.1 (4)
C1—C2—C3—C4	0.1 (4)	C1—O1—Cu2—Cl1	145.23 (16)
C2—C3—C4—C5	−0.5 (4)	Cu1—O1—Cu2—Cl1	−70.93 (6)
C3—C4—C5—C6	−0.4 (4)	C1—O1—Cu2—Cu1	−143.8 (2)
C4—C5—C6—C1	1.7 (4)	C8—N1—Cu2—O2	−168.1 (2)
C4—C5—C6—C7	−175.4 (2)	C7—N1—Cu2—O2	65.5 (3)
O1—C1—C6—C5	177.8 (2)	C8—N1—Cu2—O1	136.78 (16)
C2—C1—C6—C5	−2.1 (3)	C7—N1—Cu2—O1	10.33 (17)
O1—C1—C6—C7	−5.0 (3)	C8—N1—Cu2—N2	−52.22 (17)
C2—C1—C6—C7	175.0 (2)	C7—N1—Cu2—N2	−178.67 (17)
C5—C6—C7—N1	−119.7 (2)	C8—N1—Cu2—Cl1	48.06 (16)
C1—C6—C7—N1	63.2 (3)	C7—N1—Cu2—Cl1	−78.39 (16)
N1—C8—C9—C10	−64.3 (3)	C8—N1—Cu2—Cu1	131.34 (14)
C8—C9—C10—N2	63.9 (3)	C7—N1—Cu2—Cu1	4.9 (2)
N2—C11—C12—C13	122.6 (2)	C10—N2—Cu2—O2	−143.06 (16)
N2—C11—C12—C17	−61.6 (3)	C11—N2—Cu2—O2	−19.41 (17)
C17—C12—C13—C14	−1.6 (4)	C10—N2—Cu2—O1	178.2 (3)
C11—C12—C13—C14	174.2 (2)	C11—N2—Cu2—O1	−58.1 (5)
C12—C13—C14—C15	0.5 (4)	C10—N2—Cu2—N1	51.32 (17)
C13—C14—C15—C16	0.7 (4)	C11—N2—Cu2—N1	174.98 (17)
C14—C15—C16—C17	−0.7 (4)	C10—N2—Cu2—Cl1	−52.64 (16)
C15—C16—C17—O2	179.0 (2)	C11—N2—Cu2—Cl1	71.02 (16)
C15—C16—C17—C12	−0.4 (3)	C10—N2—Cu2—Cu1	−132.18 (14)
C13—C12—C17—O2	−177.9 (2)	C11—N2—Cu2—Cu1	−8.5 (2)
C11—C12—C17—O2	6.1 (3)	C17—O2—Cu1—O1	−139.7 (2)
C13—C12—C17—C16	1.5 (3)	Cu2—O2—Cu1—O1	20.00 (8)
C11—C12—C17—C16	−174.5 (2)	C17—O2—Cu1—O1ⁱ	40.3 (2)
C9—C8—N1—C7	−170.9 (2)	Cu2—O2—Cu1—O1ⁱ	−160.00 (8)
C9—C8—N1—Cu2	61.9 (2)	C17—O2—Cu1—Cu2	−159.7 (3)
C6—C7—N1—C8	176.1 (2)	C17—O2—Cu1—Cu2ⁱ	20.3 (3)
C6—C7—N1—Cu2	−56.8 (2)	Cu2—O2—Cu1—Cu2ⁱ	180.0
C9—C10—N2—C11	174.7 (2)	C1—O1—Cu1—O2	118.85 (19)
C9—C10—N2—Cu2	−60.8 (2)	Cu2—O1—Cu1—O2	−19.76 (8)
C12—C11—N2—C10	−173.3 (2)	C1—O1—Cu1—O2ⁱ	−61.15 (19)
C12—C11—N2—Cu2	61.7 (2)	Cu2—O1—Cu1—O2ⁱ	160.24 (8)
C2—C1—O1—Cu1	0.6 (3)	C1—O1—Cu1—Cu2	138.6 (2)
C6—C1—O1—Cu1	−179.40 (15)	C1—O1—Cu1—Cu2ⁱ	−41.4 (2)
C2—C1—O1—Cu2	131.2 (2)	Cu2—O1—Cu1—Cu2ⁱ	180.0
C6—C1—O1—Cu2	−48.8 (3)	O1—Cu2—Cu1—O2	150.01 (11)
C16—C17—O2—Cu1	15.6 (3)	N1—Cu2—Cu1—O2	158.32 (12)
C12—C17—O2—Cu1	−164.97 (17)	N2—Cu2—Cu1—O2	−16.86 (11)
C16—C17—O2—Cu2	−139.41 (19)	Cl1—Cu2—Cu1—O2	−106.58 (8)
C12—C17—O2—Cu2	40.0 (3)	O2—Cu2—Cu1—O2ⁱ	180.0
C17—O2—Cu2—O1	142.55 (19)	O1—Cu2—Cu1—O2ⁱ	−29.99 (11)
Cu1—O2—Cu2—O1	−19.52 (7)	N1—Cu2—Cu1—O2ⁱ	−21.68 (12)
C17—O2—Cu2—N1	85.7 (3)	N2—Cu2—Cu1—O2ⁱ	163.14 (11)
Cu1—O2—Cu2—N1	−76.4 (3)	Cl1—Cu2—Cu1—O2ⁱ	73.42 (8)
C17—O2—Cu2—N2	−30.28 (19)	O2—Cu2—Cu1—O1	−150.01 (11)
Cu1—O2—Cu2—N2	167.64 (8)	N1—Cu2—Cu1—O1	8.31 (11)
C17—O2—Cu2—Cl1	−129.39 (18)	N2—Cu2—Cu1—O1	−166.86 (11)
Cu1—O2—Cu2—Cl1	68.54 (6)	Cl1—Cu2—Cu1—O1	103.41 (8)
C17—O2—Cu2—Cu1	162.1 (2)	O2—Cu2—Cu1—O1ⁱ	29.99 (11)
C1—O1—Cu2—O2	−124.44 (17)	O1—Cu2—Cu1—O1ⁱ	180.0
Cu1—O1—Cu2—O2	19.40 (7)	N1—Cu2—Cu1—O1ⁱ	−171.69 (11)
C1—O1—Cu2—N1	42.19 (17)	N2—Cu2—Cu1—O1ⁱ	13.14 (11)
Cu1—O1—Cu2—N1	−173.97 (8)	Cl1—Cu2—Cu1—O1ⁱ	−76.59 (8)

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu₃(C₁₇H₂₀N₂O₂)₂Cl₂]
M_r	830.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.0189 (7), 15.3861 (8), 10.7441 (8)
β (°)	106.959 (7)
V (Å³)	1742.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.01
Crystal size (mm)	0.36 × 0.22 × 0.14

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2002)
T_min, T_max	0.531, 0.766
No. of measured, independent and observed [I > 2σ(I)] reflections	12067, 3481, 2969
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.075, 1.10
No. of reflections	3481
No. of parameters	220
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.32

Computer programs: CrysAlis CCD (Oxford Diffraction, 2002), CrysAlis RED (Oxford Diffraction, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Cu2—Cl1	2.5092 (7)	O2—Cu1	1.9108 (16)
Cu2—Cu1	2.9138 (3)	O2—Cu2	1.9632 (16)
O1—Cu1	1.9191 (15)	N1—Cu2	1.995 (2)
O1—Cu2	1.9825 (16)	N2—Cu2	1.995 (2)

O2—Cu1—O1	80.93 (7)	O2—Cu2—N2	93.17 (7)
O2—Cu1—Cu2	41.91 (5)	O1—Cu2—N2	168.74 (8)
O1—Cu1—Cu2	42.52 (5)	O2—Cu2—Cl1	89.92 (5)
O2—Cu2—O1	78.09 (7)	O1—Cu2—Cl1	88.09 (5)
O2—Cu2—N1	163.99 (8)	Cu1—O1—Cu2	96.62 (7)
O1—Cu2—N1	92.91 (7)	Cu1—O2—Cu2	97.54 (7)

Acknowledgements

OA is grateful to DAAD for support and acknowledges the financial support of the Ankara University Research Fund (grant No. 20050705105).

References

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