Bis{μ-2,4-di-tert-butyl-6-[3-(1H-imidazol-1-yl)propyl­imino­meth­yl]phenolato}bis­[acetatocopper(II)]

Şahin, O.; Büyükgüngör, O.; Ulusoy, M.; Çetinkaya, B.

doi:10.1107/S1600536807063283

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m51

https://doi.org/10.1107/S1600536807063283

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Bis{μ-2,4-di-tert-butyl-6-[3-(1H-imidazol-1-yl)propyliminomethyl]phenolato}bis[acetatocopper(II)]

Onur Şahin,^a ^* Orhan Büyükgüngör,^a Mahmut Ulusoy ^b and Bekir Çetinkaya ^b

^aDepartment of Physics, Ondokuz Mayıs University, TR-55139, Samsun, Turkey, and ^bDepartment of Chemistry, Ege University, TR-35100, Izmir, Turkey
^*Correspondence e-mail: onurs@omu.edu.tr

(Received 30 October 2007; accepted 26 November 2007; online 6 December 2007)

In the centrosymmetric title compound, [Cu₂(C₂₁H₃₀N₃O)₂(C₂H₃O₂)₂], each Cu atom has a distorted tetrahedral coordination geometry defined by N and O atoms in a chelate ring, N of an imidazole ring, and an acetate O atom. The uncoordinated acetate O atom is disordered over two sites with occupancies 0.7:0.3.

Related literature

For related literature, see: Djebbar et al. (1997 ); Hansen et al. (1996 ); Huang et al. (2002 ); Lacroix et al. (2004 ); Tas et al. (2004 ).

Experimental

Crystal data

[Cu₂(C₂₁H₃₀N₃O)₂(C₂H₃O₂)₂]
M_r = 926.13
Monoclinic, P 2₁ /c
a = 14.1745 (11) Å
b = 10.2898 (8) Å
c = 19.0850 (17) Å
β = 116.502 (6)°
V = 2491.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 296 K
0.25 × 0.19 × 0.07 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.741, T_max = 0.914
34842 measured reflections
4905 independent reflections
2485 reflections with I > 2σ(I)
R_int = 0.167

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.128
S = 0.95
4905 reflections
275 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Selected bond lengths (Å)

N1—Cu1	1.957 (4)
N3—Cu1	1.989 (4)
O1—Cu1	1.910 (3)
O2—Cu1	1.966 (3)

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807063283/cf2164sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063283/cf2164Isup2.hkl

checkCIF report

Comment top

Considerable attention has been paid to the chemistry of metal complexes of Schiff bases containing nitrogen and other donors (Djebbar et al., 1997). This may be attributed to their stability, biochemical and analytical uses, and potential applications in fields such as oxidation catalysis, electrochemical and molecular materials with non-linear optical properties, and therapeutic applications (Lacroix et al., 2004). The use of the salen ligand framework in catalytic reactions has been receiving increasing interest due to the aforementioned advantage and its success in many newly discovered processes. Most notable is the asymmetric ring opening of epoxides by a Cr(salen)Cl catalyst which was developed by Jacobsen and co-workers in the mid-1990 s (Hansen et al., 1996). A very important reaction in organic synthesis which involves the use of predominantly chromium-based salen complexes is the Diels-Alder reaction. Indeed, there is a report where these catalysts have been employed as part of a lengthy synthetic strategy to afford complex natural products (Huang et al., 2002). In this study, we report the structural characterization of a dinuclear Cu(II) Schiff base complex, which was previously investigated by different techniques (Tas et al., 2004). We envisaged that the free imidazole group of the proposed structure (I) should interact with aliphatic alkyl halides such as n-butyl bromide to give novel copper(II) complexes, leading to ionic liquids. However, all attempts under different and drastic conditions failed. This led us to reconsider the proposed structure (I). Therefore, for detailed information about the coordination mode of the ligands and for full characterization of the complex, a single-crystal X-ray determination has been carried out.

The centrosymmetric molecular structure, with the atomic labelling scheme, is presented in Fig.1. The copper atom is in a distorted tetrahedral coordination geometry defined by atoms N1 and O1 in a chelate ring, N3 of an imidazole ring, and an acetate atom O2. Atoms N1 and O1 are bonded to Cu1 to form a six-membered chelate ring (–C1—C2—C7—N1—Cu1—O1-). The dihedral angle between the phenyl ring and this chelate ring is 6.5 (4)°. The significant difference between Cu—L bond distances [Cu—O1 = 1.910 (3) Å, Cu—O2 = 1.966 (3) Å, Cu—N1 = 1.957 (4)Å and Cu—N3 = 1.989 (4) Å] has also been observed in other copper complexes. The longer Cu1···O3 distance and the larger Cu1—O2—C22 angle suggest there is no bonding interaction between atoms Cu1 and O3.

Related literature top

For related literature, see: Djebbar et al. (1997); Hansen et al. (1996); Huang et al. (2002); Lacroix et al. (2004); Tas et al. (2004).

Experimental top

N-[1-(3-Aminopropyl)imidazole]-3,5-di-t-butylsalicylaldimine ligand and its copper(II) complex were synthesized according to the literature procedure (Tas et al., 2004).

Structure description top

For related literature, see: Djebbar et al. (1997); Hansen et al. (1996); Huang et al. (2002); Lacroix et al. (2004); Tas et al. (2004).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) 1 - x, 1 - y, 1 - z.]

Bis{µ-2,4-di-tert-butyl-6-[3-(1H-imidazol-1- yl)propyliminomethyl]phenolato}bis[acetatocopper(II)] top

Crystal data top

[Cu₂(C₂₁H₃₀N₃O)₂(C₂H₃O₂)₂]	F(000) = 980
M_r = 926.13	D_x = 1.235 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 29181 reflections
a = 14.1745 (11) Å	θ = 1.6–27.9°
b = 10.2898 (8) Å	µ = 0.90 mm⁻¹
c = 19.0850 (17) Å	T = 296 K
β = 116.502 (6)°	Prism, black
V = 2491.1 (4) Å³	0.25 × 0.19 × 0.07 mm
Z = 2

Data collection top

STOE IPDSII diffractometer	4905 independent reflections
Radiation source: fine-focus sealed tube	2485 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.167
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 2.2°
rotation method scans	h = −17→17
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
T_min = 0.741, T_max = 0.914	l = −23→23
34842 measured 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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0447P)²] where P = (F_o² + 2F_c²)/3
4905 reflections	(Δ/σ)_max < 0.001
275 parameters	Δρ_max = 0.31 e Å⁻³
12 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[Cu₂(C₂₁H₃₀N₃O)₂(C₂H₃O₂)₂]	V = 2491.1 (4) Å³
M_r = 926.13	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.1745 (11) Å	µ = 0.90 mm⁻¹
b = 10.2898 (8) Å	T = 296 K
c = 19.0850 (17) Å	0.25 × 0.19 × 0.07 mm
β = 116.502 (6)°

Data collection top

STOE IPDSII diffractometer	4905 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2485 reflections with I > 2σ(I)
T_min = 0.741, T_max = 0.914	R_int = 0.167
34842 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	12 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 0.95	Δρ_max = 0.31 e Å⁻³
4905 reflections	Δρ_min = −0.24 e Å⁻³
275 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	Occ. (<1)
C1	0.6847 (4)	0.6496 (5)	0.4074 (3)	0.0479 (12)
C2	0.6890 (4)	0.5548 (4)	0.3558 (3)	0.0478 (12)
C3	0.7777 (4)	0.5428 (5)	0.3420 (3)	0.0573 (14)
H3	0.7789	0.4768	0.3092	0.069*
C4	0.8623 (4)	0.6239 (5)	0.3749 (3)	0.0570 (14)
C5	0.8573 (4)	0.7181 (6)	0.4260 (3)	0.0635 (15)
H5	0.9142	0.7745	0.4491	0.076*
C6	0.7738 (4)	0.7346 (5)	0.4451 (3)	0.0531 (13)
C7	0.6028 (4)	0.4685 (5)	0.3117 (3)	0.0556 (13)
H7	0.6150	0.4070	0.2810	0.067*
C8	0.9600 (5)	0.6182 (6)	0.3599 (4)	0.0752 (17)
C9	0.9519 (6)	0.5078 (8)	0.3043 (6)	0.141 (4)
H9A	0.9468	0.4264	0.3269	0.169*
H9B	1.0136	0.5074	0.2955	0.169*
H9C	0.8904	0.5200	0.2554	0.169*
C10	0.9705 (7)	0.7427 (8)	0.3223 (5)	0.131 (3)
H10A	1.0295	0.7362	0.3105	0.157*
H10B	0.9814	0.8139	0.3576	0.157*
H10C	0.9073	0.7573	0.2748	0.157*
C11	1.0571 (5)	0.5926 (11)	0.4350 (5)	0.156 (4)
H11A	1.0500	0.5106	0.4563	0.187*
H11B	1.0656	0.6605	0.4719	0.187*
H11C	1.1177	0.5902	0.4250	0.187*
C12	0.7780 (4)	0.8338 (6)	0.5050 (3)	0.0671 (15)
C13	0.8787 (5)	0.9195 (8)	0.5362 (4)	0.113 (3)
H13A	0.8786	0.9778	0.5754	0.136*
H13B	0.8796	0.9687	0.4938	0.136*
H13C	0.9400	0.8650	0.5586	0.136*
C14	0.6846 (5)	0.9279 (6)	0.4704 (3)	0.0811 (17)
H14A	0.6199	0.8802	0.4537	0.097*
H14B	0.6853	0.9722	0.4264	0.097*
H14C	0.6900	0.9903	0.5094	0.097*
C15	0.7796 (5)	0.7619 (7)	0.5764 (3)	0.0817 (18)
H15A	0.7156	0.7132	0.5605	0.098*
H15B	0.7854	0.8240	0.6157	0.098*
H15C	0.8388	0.7039	0.5974	0.098*
C16	0.4370 (4)	0.3671 (5)	0.2586 (3)	0.0649 (16)
H16A	0.4696	0.3215	0.2306	0.078*
H16B	0.3740	0.4095	0.2203	0.078*
C17	0.4064 (5)	0.2697 (6)	0.3046 (3)	0.0698 (17)
H17A	0.3537	0.2114	0.2679	0.084*
H17B	0.3742	0.3162	0.3326	0.084*
C18	0.5027 (5)	0.8115 (6)	0.6368 (4)	0.0771 (18)
H18A	0.4521	0.8271	0.6571	0.092*
H18B	0.5294	0.8949	0.6300	0.092*
C19	0.4943 (4)	0.7166 (5)	0.5142 (3)	0.0657 (15)
H19	0.5638	0.7362	0.5260	0.079*
C20	0.3381 (4)	0.6471 (6)	0.4573 (3)	0.0665 (15)
H20	0.2764	0.6086	0.4207	0.080*
C21	0.3507 (5)	0.7013 (6)	0.5248 (4)	0.0705 (16)
H21	0.3002	0.7066	0.5433	0.085*
C22	0.2820 (5)	0.6256 (6)	0.2458 (4)	0.0721 (17)
C23	0.1666 (5)	0.6146 (8)	0.1897 (4)	0.122 (3)
H23A	0.1251	0.6322	0.2169	0.146*
H23B	0.1518	0.5283	0.1683	0.146*
H23C	0.1493	0.6763	0.1480	0.146*
N1	0.5106 (3)	0.4662 (4)	0.3098 (2)	0.0543 (11)
N2	0.4498 (4)	0.7462 (4)	0.5607 (3)	0.0620 (12)
N3	0.4297 (3)	0.6572 (4)	0.4504 (2)	0.0596 (11)
O1	0.6027 (2)	0.6631 (3)	0.42159 (19)	0.0557 (9)
O2	0.3149 (3)	0.5524 (4)	0.3042 (2)	0.0705 (11)
O3A	0.327 (3)	0.721 (4)	0.253 (2)	0.105 (5)	0.30 (4)
O3B	0.3390 (11)	0.6916 (16)	0.2238 (13)	0.105 (5)	0.70 (4)
Cu1	0.46586 (5)	0.58707 (6)	0.36829 (4)	0.0531 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.035 (3)	0.061 (3)	0.044 (3)	0.006 (2)	0.014 (2)	0.010 (2)
C2	0.041 (3)	0.054 (3)	0.051 (3)	0.006 (2)	0.022 (2)	0.006 (2)
C3	0.056 (3)	0.065 (4)	0.060 (3)	0.020 (3)	0.033 (3)	0.019 (3)
C4	0.040 (3)	0.064 (4)	0.069 (3)	0.011 (2)	0.026 (3)	0.020 (3)
C5	0.035 (3)	0.081 (4)	0.068 (4)	−0.001 (3)	0.018 (3)	0.014 (3)
C6	0.037 (3)	0.064 (3)	0.052 (3)	0.001 (2)	0.014 (2)	0.007 (3)
C7	0.058 (3)	0.066 (4)	0.046 (3)	0.005 (3)	0.026 (3)	0.001 (2)
C8	0.056 (3)	0.093 (5)	0.092 (4)	0.007 (3)	0.047 (3)	0.020 (4)
C9	0.119 (7)	0.128 (7)	0.242 (11)	0.001 (5)	0.141 (8)	−0.009 (8)
C10	0.145 (7)	0.129 (7)	0.175 (8)	−0.003 (6)	0.121 (7)	0.028 (6)
C11	0.059 (4)	0.294 (13)	0.134 (6)	0.047 (7)	0.061 (5)	0.069 (8)
C12	0.052 (3)	0.077 (4)	0.067 (4)	−0.010 (3)	0.022 (3)	−0.005 (3)
C13	0.090 (5)	0.139 (7)	0.117 (5)	−0.054 (5)	0.052 (4)	−0.053 (5)
C14	0.089 (4)	0.066 (4)	0.087 (4)	−0.005 (4)	0.037 (4)	−0.014 (3)
C15	0.065 (4)	0.113 (5)	0.052 (3)	0.014 (4)	0.014 (3)	−0.002 (3)
C16	0.063 (4)	0.077 (4)	0.055 (3)	−0.008 (3)	0.026 (3)	−0.023 (3)
C17	0.071 (4)	0.075 (4)	0.073 (4)	−0.029 (3)	0.040 (3)	−0.039 (3)
C18	0.100 (5)	0.061 (4)	0.089 (4)	0.000 (3)	0.059 (4)	−0.024 (3)
C19	0.053 (3)	0.085 (4)	0.070 (4)	−0.011 (3)	0.036 (3)	−0.020 (3)
C20	0.046 (3)	0.085 (4)	0.072 (4)	−0.007 (3)	0.029 (3)	−0.006 (3)
C21	0.063 (4)	0.086 (4)	0.081 (4)	−0.002 (3)	0.049 (3)	−0.012 (3)
C22	0.054 (4)	0.067 (5)	0.092 (5)	0.001 (3)	0.029 (4)	0.002 (4)
C23	0.063 (4)	0.150 (8)	0.110 (5)	−0.001 (5)	0.001 (4)	0.012 (5)
N1	0.046 (2)	0.069 (3)	0.047 (2)	−0.002 (2)	0.020 (2)	−0.003 (2)
N2	0.063 (3)	0.064 (3)	0.070 (3)	−0.002 (2)	0.039 (3)	−0.014 (2)
N3	0.044 (3)	0.078 (3)	0.062 (3)	−0.002 (2)	0.028 (2)	−0.012 (2)
O1	0.0381 (19)	0.073 (2)	0.058 (2)	−0.0021 (16)	0.0235 (17)	−0.0077 (17)
O2	0.048 (2)	0.096 (3)	0.068 (2)	−0.004 (2)	0.0253 (19)	−0.007 (2)
O3A	0.079 (5)	0.092 (7)	0.162 (12)	0.008 (4)	0.070 (6)	0.041 (7)
O3B	0.079 (5)	0.092 (7)	0.162 (12)	0.008 (4)	0.070 (6)	0.041 (7)
Cu1	0.0392 (3)	0.0685 (4)	0.0521 (3)	−0.0025 (4)	0.0207 (2)	−0.0072 (4)

Geometric parameters (Å, º) top

C1—O1	1.313 (5)	C14—H14C	0.960
C1—C2	1.407 (6)	C15—H15A	0.960
C1—C6	1.439 (7)	C15—H15B	0.960
C2—C3	1.399 (6)	C15—H15C	0.960
C2—C7	1.440 (7)	C16—N1	1.474 (6)
C3—C4	1.363 (7)	C16—C17	1.517 (7)
C3—H3	0.930	C16—H16A	0.970
C4—C5	1.400 (7)	C16—H16B	0.970
C4—C8	1.535 (7)	C17—C18ⁱ	1.524 (8)
C5—C6	1.395 (7)	C17—H17A	0.970
C5—H5	0.930	C17—H17B	0.970
C6—C12	1.514 (7)	C18—N2	1.467 (7)
C7—N1	1.291 (6)	C18—C17ⁱ	1.524 (8)
C7—H7	0.930	C18—H18A	0.970
C8—C11	1.503 (9)	C18—H18B	0.970
C8—C10	1.508 (9)	C19—N3	1.304 (6)
C8—C9	1.524 (10)	C19—N2	1.331 (6)
C9—H9A	0.960	C19—H19	0.930
C9—H9B	0.960	C20—C21	1.341 (7)
C9—H9C	0.960	C20—N3	1.366 (6)
C10—H10A	0.960	C20—H20	0.930
C10—H10B	0.960	C21—N2	1.341 (7)
C10—H10C	0.960	C21—H21	0.930
C11—H11A	0.960	C22—O3A	1.14 (4)
C11—H11B	0.960	C22—O2	1.249 (7)
C11—H11C	0.960	C22—O3B	1.263 (18)
C12—C14	1.532 (8)	C22—C23	1.509 (8)
C12—C15	1.541 (8)	C23—H23A	0.960
C12—C13	1.552 (8)	C23—H23B	0.960
C13—H13A	0.960	C23—H23C	0.960
C13—H13B	0.960	N1—Cu1	1.957 (4)
C13—H13C	0.960	N3—Cu1	1.989 (4)
C14—H14A	0.960	O1—Cu1	1.910 (3)
C14—H14B	0.960	O2—Cu1	1.966 (3)

O1—C1—C2	122.5 (4)	H14B—C14—H14C	109.5
O1—C1—C6	119.5 (4)	C12—C15—H15A	109.5
C2—C1—C6	118.0 (4)	C12—C15—H15B	109.5
C3—C2—C1	121.1 (5)	H15A—C15—H15B	109.5
C3—C2—C7	115.8 (5)	C12—C15—H15C	109.5
C1—C2—C7	123.1 (4)	H15A—C15—H15C	109.5
C4—C3—C2	122.7 (5)	H15B—C15—H15C	109.5
C4—C3—H3	118.7	N1—C16—C17	112.0 (4)
C2—C3—H3	118.7	N1—C16—H16A	109.2
C3—C4—C5	115.9 (5)	C17—C16—H16A	109.2
C3—C4—C8	125.0 (5)	N1—C16—H16B	109.2
C5—C4—C8	119.2 (5)	C17—C16—H16B	109.2
C6—C5—C4	125.4 (5)	H16A—C16—H16B	107.9
C6—C5—H5	117.3	C16—C17—C18ⁱ	114.9 (5)
C4—C5—H5	117.3	C16—C17—H17A	108.5
C5—C6—C1	116.9 (5)	C18ⁱ—C17—H17A	108.5
C5—C6—C12	121.8 (5)	C16—C17—H17B	108.5
C1—C6—C12	121.2 (4)	C18ⁱ—C17—H17B	108.5
N1—C7—C2	127.8 (5)	H17A—C17—H17B	107.5
N1—C7—H7	116.1	N2—C18—C17ⁱ	111.5 (4)
C2—C7—H7	116.1	N2—C18—H18A	109.3
C11—C8—C10	111.1 (7)	C17ⁱ—C18—H18A	109.3
C11—C8—C9	106.6 (6)	N2—C18—H18B	109.3
C10—C8—C9	107.1 (6)	C17ⁱ—C18—H18B	109.3
C11—C8—C4	110.3 (5)	H18A—C18—H18B	108.0
C10—C8—C4	110.2 (5)	N3—C19—N2	112.7 (5)
C9—C8—C4	111.4 (5)	N3—C19—H19	123.7
C8—C9—H9A	109.5	N2—C19—H19	123.7
C8—C9—H9B	109.5	C21—C20—N3	109.7 (5)
H9A—C9—H9B	109.5	C21—C20—H20	125.2
C8—C9—H9C	109.5	N3—C20—H20	125.2
H9A—C9—H9C	109.5	C20—C21—N2	107.1 (5)
H9B—C9—H9C	109.5	C20—C21—H21	126.5
C8—C10—H10A	109.5	N2—C21—H21	126.5
C8—C10—H10B	109.5	O3A—C22—O2	116 (2)
H10A—C10—H10B	109.5	O2—C22—O3B	125.6 (8)
C8—C10—H10C	109.5	O3A—C22—C23	121.2 (19)
H10A—C10—H10C	109.5	O2—C22—C23	116.3 (6)
H10B—C10—H10C	109.5	O3B—C22—C23	117.1 (9)
C8—C11—H11A	109.5	C22—C23—H23A	109.5
C8—C11—H11B	109.5	C22—C23—H23B	109.5
H11A—C11—H11B	109.5	H23A—C23—H23B	109.5
C8—C11—H11C	109.5	C22—C23—H23C	109.5
H11A—C11—H11C	109.5	H23A—C23—H23C	109.5
H11B—C11—H11C	109.5	H23B—C23—H23C	109.5
C6—C12—C14	111.4 (4)	C7—N1—C16	116.1 (4)
C6—C12—C15	108.9 (5)	C7—N1—Cu1	123.6 (3)
C14—C12—C15	110.7 (5)	C16—N1—Cu1	120.2 (3)
C6—C12—C13	113.1 (5)	C19—N2—C21	106.3 (5)
C14—C12—C13	106.0 (5)	C19—N2—C18	125.4 (5)
C15—C12—C13	106.6 (5)	C21—N2—C18	128.3 (5)
C12—C13—H13A	109.5	C19—N3—C20	104.3 (4)
C12—C13—H13B	109.5	C19—N3—Cu1	125.8 (4)
H13A—C13—H13B	109.5	C20—N3—Cu1	129.7 (4)
C12—C13—H13C	109.5	C1—O1—Cu1	128.9 (3)
H13A—C13—H13C	109.5	C22—O2—Cu1	108.4 (4)
H13B—C13—H13C	109.5	O1—Cu1—N1	93.07 (15)
C12—C14—H14A	109.5	O1—Cu1—O2	165.98 (17)
C12—C14—H14B	109.5	N1—Cu1—O2	93.98 (16)
H14A—C14—H14B	109.5	O1—Cu1—N3	89.40 (16)
C12—C14—H14C	109.5	N1—Cu1—N3	160.63 (17)
H14A—C14—H14C	109.5	O2—Cu1—N3	87.95 (16)

O1—C1—C2—C3	−179.9 (4)	C17—C16—N1—Cu1	−64.3 (5)
C6—C1—C2—C3	0.5 (6)	N3—C19—N2—C21	0.8 (7)
O1—C1—C2—C7	2.7 (7)	N3—C19—N2—C18	179.1 (5)
C6—C1—C2—C7	−176.9 (4)	C20—C21—N2—C19	−0.7 (7)
C1—C2—C3—C4	−2.5 (7)	C20—C21—N2—C18	−178.9 (5)
C7—C2—C3—C4	175.1 (4)	C17ⁱ—C18—N2—C19	−62.9 (7)
C2—C3—C4—C5	2.3 (7)	C17ⁱ—C18—N2—C21	115.0 (6)
C2—C3—C4—C8	−177.9 (5)	N2—C19—N3—C20	−0.7 (6)
C3—C4—C5—C6	−0.1 (7)	N2—C19—N3—Cu1	−176.3 (4)
C8—C4—C5—C6	−179.9 (5)	C21—C20—N3—C19	0.2 (6)
C4—C5—C6—C1	−1.8 (7)	C21—C20—N3—Cu1	175.6 (4)
C4—C5—C6—C12	176.1 (5)	C2—C1—O1—Cu1	−11.4 (6)
O1—C1—C6—C5	−178.2 (4)	C6—C1—O1—Cu1	168.3 (3)
C2—C1—C6—C5	1.5 (6)	O3A—C22—O2—Cu1	−26 (2)
O1—C1—C6—C12	4.0 (7)	O3B—C22—O2—Cu1	12.5 (16)
C2—C1—C6—C12	−176.4 (4)	C23—C22—O2—Cu1	−179.2 (5)
C3—C2—C7—N1	−174.9 (5)	C1—O1—Cu1—N1	11.6 (4)
C1—C2—C7—N1	2.6 (8)	C1—O1—Cu1—O2	−108.6 (7)
C3—C4—C8—C11	−119.3 (7)	C1—O1—Cu1—N3	172.3 (4)
C5—C4—C8—C11	60.5 (7)	C7—N1—Cu1—O1	−6.0 (4)
C3—C4—C8—C10	117.7 (6)	C16—N1—Cu1—O1	175.3 (4)
C5—C4—C8—C10	−62.5 (7)	C7—N1—Cu1—O2	161.9 (4)
C3—C4—C8—C9	−1.1 (8)	C16—N1—Cu1—O2	−16.9 (4)
C5—C4—C8—C9	178.7 (6)	C7—N1—Cu1—N3	−103.0 (6)
C5—C6—C12—C14	123.9 (5)	C16—N1—Cu1—N3	78.3 (6)
C1—C6—C12—C14	−58.3 (7)	C22—O2—Cu1—O1	33.7 (8)
C5—C6—C12—C15	−113.7 (5)	C22—O2—Cu1—N1	−86.3 (4)
C1—C6—C12—C15	64.1 (6)	C22—O2—Cu1—N3	113.0 (4)
C5—C6—C12—C13	4.6 (8)	C19—N3—Cu1—O1	−6.0 (5)
C1—C6—C12—C13	−177.6 (5)	C20—N3—Cu1—O1	179.6 (5)
N1—C16—C17—C18ⁱ	−63.0 (6)	C19—N3—Cu1—N1	91.6 (7)
N3—C20—C21—N2	0.3 (7)	C20—N3—Cu1—N1	−82.9 (7)
C2—C7—N1—C16	179.6 (5)	C19—N3—Cu1—O2	−172.2 (5)
C2—C7—N1—Cu1	0.8 (7)	C20—N3—Cu1—O2	13.3 (5)
C17—C16—N1—C7	116.9 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₂₁H₃₀N₃O)₂(C₂H₃O₂)₂]
M_r	926.13
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	14.1745 (11), 10.2898 (8), 19.0850 (17)
β (°)	116.502 (6)
V (Å³)	2491.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.25 × 0.19 × 0.07

Data collection
Diffractometer	STOE IPDSII
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.741, 0.914
No. of measured, independent and observed [I > 2σ(I)] reflections	34842, 4905, 2485
R_int	0.167
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.128, 0.95
No. of reflections	4905
No. of parameters	275
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.24

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

N1—Cu1	1.957 (4)	O1—Cu1	1.910 (3)
N3—Cu1	1.989 (4)	O2—Cu1	1.966 (3)

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant No. F279 of the University Research Fund).

References

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