Diacetonitrile­[N,N′-bis­(3,4,5-trimethoxy­benzyl­idene)ethyl­enediamine]copper(I) perchlorate

Khalaji, A.D.; Brad, K.; Zhang, Y.

doi:10.1107/S1600536807065919

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m189

https://doi.org/10.1107/S1600536807065919

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Diacetonitrile[N,N′-bis(3,4,5-trimethoxybenzylidene)ethylenediamine]copper(I) perchlorate

Aliakbar Dehno Khalaji,^a Korbanjhon Brad ^b and Yan Zhang ^c ^*

^aDepartment of Science, Gorgan University of Agricultural Sciences and Natural Resources, Gorgan 49189-43464, Iran, ^bSchool of Chemistry and Biological Science, Yili Normal University, Yining 835000, People's Republic of China, and ^cCollege of Pharmaceuticals and Biotechnology, Tianjin University, Tianjin 300072, People's Republic of China
^*Correspondence e-mail: cpzyyan@hotmail.com

(Received 13 November 2007; accepted 6 December 2007; online 12 December 2007)

In the title compound, [Cu(C₂H₃N)₂(C₂₂H₂₈N₂O₆)]ClO₄, the Cu atom is coordinated by two N atoms from one bidentate Schiff base ligand and two N atoms from two acetonitrile groups. The Cu atom adopts a tetrahedral geometry. The Cu—N(ligand) distances are 2.076 (3) and 2.089 (3) Å, and the Cu—N(acetonitrile) distances are 1.964 (4) and 1.975 (4) Å.

Related literature

For related literature, see: Amirnasr et al. (2006 ); Chowdhury et al. (2000 ); Dakin et al. (2000 ); Khalaji et al. (2007 ).

Experimental

Crystal data

[Cu(C₂H₃N)₂(C₂₂H₂₈N₂O₆)]ClO₄
M_r = 661.56
Triclinic, $[P \overline 1]$
a = 9.869 (2) Å
b = 11.903 (3) Å
c = 14.904 (3) Å
α = 80.537 (4)°
β = 71.677 (4)°
γ = 68.285 (4)°
V = 1541.9 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.85 mm⁻¹
T = 294 (2) K
0.24 × 0.22 × 0.18 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.821, T_max = 0.862
8034 measured reflections
5414 independent reflections
3408 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.141
S = 1.01
5414 reflections
387 parameters
34 restraints
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.37 e Å⁻³

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807065919/bt2614sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065919/bt2614Isup2.hkl

checkCIF report

Comment top

Copper(I) complexes have long been used in organic synthesis as catalyst (Dakin et al., 2000), and the design of supramolecular arrays (Amirnasr et al., 2006).

The coordination of the Cu atom is nearly tetrahedral (Fig. 1), with four N atoms, two from two acetonitrile groups and the other two from one bidentate Schiff base ligand (3,4,5-MeO-ba)₂en, forming the CuN4 chromophore. Although a tetrahedral geometry is to be expected for a four-coordinated Cu(I) complexes, the geometry about the Cu(I) in this structure is distorted by the bite angle of the chelating ligand. The N(1)—Cu(1)—N(2) angle is 84.97 (13) and N(3)—Cu(1)—N(4) angle is 103.04 (16)° in this structure being smaller than the tetrahedral values, however, other angles are larger than the tetrahedral values, which posses approximate C2 local symmetry. The Cu—N bond lengths [Cu(1)—N(3), 1.964 (4); Cu(1)—N(4), 1.975 (4); Cu(1)—N(2), 2.076 (3) and Cu(1)—N(1) 2.089 (3) Å] agree well with the same distances in other tetrahedral copper(I) complexes (Chowdhury et al., 2000.; Dakin et al., 2000). The N(1)=C(7) and N(2)=C(13) bond lengths of 1.274 (5) and 1.277 (5) Å, respectively, conform to the value for a double bond, while the C(11)—N(1) and C(12)—N(2) bond lengths of 1.475 (5) and 1.468 (5) Å, respectively, conform to the value for a single bond and are comparable to the corresponding values observed in other tetrahedral copper(I) complexes (Chowdhury et al., 2000.; Dakin et al., 2000). The ligand adopts a Z,Z configuration in this structure.

Related literature top

For related literature, see: Amirnasr et al. (2006); Chowdhury et al. (2000); Dakin et al. (2000); Khalaji et al. (2007).

Experimental top

The N,N'-Bis(3,4,5-trimethoxybenzylidene)ethylenediamine (3,4,5-MeO-ba)₂en) ligand was prepared as reported elsewhere (Khalaji et al., 2007). The reaction between [Cu(CH₃CN)₄]ClO₄ (0.326 mg, 0.1 mol) and the (3,4,5-MeO-ba)₂en ligand (0.416 g, 0.1 mol) in 10 ml CH₃CN at room temperature lead to the formation of the copper(I) complex.

Structure description top

Copper(I) complexes have long been used in organic synthesis as catalyst (Dakin et al., 2000), and the design of supramolecular arrays (Amirnasr et al., 2006).

For related literature, see: Amirnasr et al. (2006); Chowdhury et al. (2000); Dakin et al. (2000); Khalaji et al. (2007).

Computing details top

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

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellopsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

Diacetonitrile[N,N'-bis(3,4,5-trimethoxybenzylidene)ethylenediamine]copper(I) perchlorate top

Crystal data top

[Cu(C₂H₃N)₂(C₂₂H₂₈N₂O₆)]ClO₄	Z = 2
M_r = 661.56	F(000) = 688
Triclinic, P1	D_x = 1.425 Mg m⁻³
a = 9.869 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.903 (3) Å	Cell parameters from 2161 reflections
c = 14.904 (3) Å	θ = 2.3–22.6°
α = 80.537 (4)°	µ = 0.85 mm⁻¹
β = 71.677 (4)°	T = 294 K
γ = 68.285 (4)°	Block, blue
V = 1541.9 (6) Å³	0.24 × 0.22 × 0.18 mm

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	5414 independent reflections
Radiation source: fine-focus sealed tube	3408 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
φ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→9
T_min = 0.821, T_max = 0.862	k = −14→14
8034 measured reflections	l = −17→16

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0591P)² + 1.2218P] where P = (F_o² + 2F_c²)/3
5414 reflections	(Δ/σ)_max = 0.001
387 parameters	Δρ_max = 0.62 e Å⁻³
34 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Cu(C₂H₃N)₂(C₂₂H₂₈N₂O₆)]ClO₄	γ = 68.285 (4)°
M_r = 661.56	V = 1541.9 (6) Å³
Triclinic, P1	Z = 2
a = 9.869 (2) Å	Mo Kα radiation
b = 11.903 (3) Å	µ = 0.85 mm⁻¹
c = 14.904 (3) Å	T = 294 K
α = 80.537 (4)°	0.24 × 0.22 × 0.18 mm
β = 71.677 (4)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	5414 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3408 reflections with I > 2σ(I)
T_min = 0.821, T_max = 0.862	R_int = 0.025
8034 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	34 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.01	Δρ_max = 0.62 e Å⁻³
5414 reflections	Δρ_min = −0.37 e Å⁻³
387 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	0.16626 (7)	0.63549 (5)	0.25396 (4)	0.0508 (2)
O1	0.3716 (4)	0.9169 (3)	0.3552 (2)	0.0588 (9)
O2	0.5608 (4)	0.8412 (3)	0.4633 (2)	0.0591 (9)
O3	0.7220 (4)	0.6058 (3)	0.4854 (2)	0.0602 (9)
O4	−0.3452 (4)	0.5705 (3)	0.0206 (2)	0.0612 (9)
O5	−0.4326 (3)	0.8102 (3)	0.0469 (2)	0.0612 (9)
O6	−0.3194 (4)	0.8895 (3)	0.1522 (2)	0.0575 (8)
N1	0.3752 (4)	0.5043 (3)	0.2585 (2)	0.0410 (8)
N2	0.1072 (4)	0.4906 (3)	0.2395 (2)	0.0419 (8)
N3	0.0368 (5)	0.7333 (4)	0.3633 (3)	0.0572 (10)
N4	0.1843 (5)	0.7587 (4)	0.1488 (3)	0.0563 (10)
C1	0.4243 (5)	0.7104 (4)	0.3181 (3)	0.0429 (10)
H1	0.3572	0.7356	0.2809	0.051*
C2	0.4436 (5)	0.7945 (4)	0.3627 (3)	0.0430 (10)
C3	0.5417 (5)	0.7562 (4)	0.4204 (3)	0.0454 (11)
C4	0.6249 (5)	0.6343 (4)	0.4300 (3)	0.0445 (11)
C5	0.6075 (5)	0.5508 (4)	0.3837 (3)	0.0413 (10)
H5	0.6643	0.4692	0.3890	0.050*
C6	0.5055 (4)	0.5889 (4)	0.3293 (3)	0.0390 (10)
C7	0.4868 (5)	0.4930 (4)	0.2891 (3)	0.0414 (10)
H7	0.5627	0.4175	0.2856	0.050*
C8	0.2938 (6)	0.9615 (4)	0.2841 (4)	0.0693 (15)
H8A	0.3606	0.9302	0.2245	0.104*
H8B	0.2611	1.0483	0.2792	0.104*
H8C	0.2070	0.9359	0.3006	0.104*
C9	0.4800 (7)	0.8526 (5)	0.5606 (3)	0.0781 (17)
H9A	0.3737	0.8725	0.5678	0.117*
H9B	0.4954	0.9156	0.5847	0.117*
H9C	0.5162	0.7774	0.5952	0.117*
C10	0.8171 (5)	0.4835 (5)	0.4891 (4)	0.0629 (14)
H10A	0.7560	0.4330	0.5154	0.094*
H10B	0.8822	0.4742	0.5280	0.094*
H10C	0.8778	0.4601	0.4263	0.094*
C11	0.3764 (5)	0.3933 (4)	0.2262 (3)	0.0454 (11)
H11A	0.4520	0.3231	0.2462	0.054*
H11B	0.4017	0.3972	0.1576	0.054*
C12	0.2208 (5)	0.3823 (4)	0.2684 (3)	0.0484 (11)
H12A	0.2186	0.3107	0.2466	0.058*
H12B	0.1979	0.3744	0.3368	0.058*
C13	0.0175 (5)	0.4718 (4)	0.2024 (3)	0.0438 (10)
H13	0.0289	0.3915	0.1986	0.053*
C14	−0.1009 (5)	0.5636 (4)	0.1656 (3)	0.0415 (10)
C15	−0.1659 (5)	0.5225 (4)	0.1129 (3)	0.0463 (11)
H15	−0.1354	0.4401	0.1048	0.056*
C16	−0.2752 (5)	0.6037 (4)	0.0728 (3)	0.0459 (11)
C17	−0.3221 (5)	0.7267 (4)	0.0850 (3)	0.0472 (11)
C18	−0.2617 (5)	0.7676 (4)	0.1413 (3)	0.0439 (10)
C19	−0.1508 (5)	0.6868 (4)	0.1807 (3)	0.0437 (10)
H19	−0.1096	0.7144	0.2172	0.052*
C20	−0.3010 (6)	0.4441 (5)	0.0093 (4)	0.0627 (14)
H20A	−0.1954	0.4137	−0.0245	0.094*
H20B	−0.3603	0.4312	−0.0255	0.094*
H20C	−0.3174	0.4024	0.0705	0.094*
C21	−0.3830 (7)	0.8362 (5)	−0.0515 (4)	0.0844 (18)
H21A	−0.2835	0.8417	−0.0672	0.127*
H21B	−0.4521	0.9118	−0.0688	0.127*
H21C	−0.3797	0.7728	−0.0854	0.127*
C22	−0.2715 (6)	0.9347 (4)	0.2153 (4)	0.0640 (14)
H22A	−0.2970	0.8969	0.2774	0.096*
H22B	−0.3215	1.0207	0.2179	0.096*
H22C	−0.1636	0.9168	0.1932	0.096*
C23	0.1908 (6)	0.8331 (5)	0.0939 (4)	0.0683 (15)
C24	0.1990 (9)	0.9299 (7)	0.0201 (6)	0.140 (3)
H24A	0.1483	0.9267	−0.0244	0.211*
H24B	0.3034	0.9196	−0.0121	0.211*
H24C	0.1507	1.0069	0.0484	0.211*
C25	−0.0322 (6)	0.7962 (5)	0.4216 (4)	0.0623 (13)
C26	−0.1195 (9)	0.8770 (7)	0.4981 (5)	0.122 (3)
H26A	−0.0530	0.8831	0.5308	0.183*
H26B	−0.1941	0.8458	0.5415	0.183*
H26C	−0.1694	0.9558	0.4728	0.183*
Cl1	0.90012 (16)	0.16995 (12)	0.24864 (12)	0.0791 (5)
O7	0.7647 (5)	0.2159 (4)	0.2193 (4)	0.1252 (17)
O8	0.8825 (8)	0.2455 (5)	0.3203 (4)	0.171 (2)
O9	0.9177 (5)	0.0509 (3)	0.2878 (4)	0.1263 (18)
O10	1.0251 (6)	0.1770 (5)	0.1751 (4)	0.181 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0576 (4)	0.0406 (3)	0.0556 (4)	−0.0112 (3)	−0.0229 (3)	−0.0059 (3)
O1	0.073 (2)	0.0404 (18)	0.062 (2)	−0.0110 (16)	−0.0250 (18)	−0.0062 (15)
O2	0.086 (2)	0.061 (2)	0.0467 (19)	−0.0406 (18)	−0.0180 (18)	−0.0074 (16)
O3	0.070 (2)	0.061 (2)	0.065 (2)	−0.0230 (18)	−0.0396 (19)	−0.0019 (17)
O4	0.060 (2)	0.067 (2)	0.069 (2)	−0.0138 (17)	−0.0355 (18)	−0.0186 (17)
O5	0.0487 (19)	0.072 (2)	0.053 (2)	−0.0032 (17)	−0.0211 (17)	−0.0051 (17)
O6	0.064 (2)	0.0464 (19)	0.062 (2)	−0.0118 (16)	−0.0244 (18)	−0.0060 (16)
N1	0.046 (2)	0.041 (2)	0.041 (2)	−0.0138 (16)	−0.0177 (17)	−0.0072 (16)
N2	0.046 (2)	0.040 (2)	0.045 (2)	−0.0157 (17)	−0.0179 (18)	−0.0002 (16)
N3	0.062 (3)	0.053 (2)	0.054 (3)	−0.012 (2)	−0.017 (2)	−0.009 (2)
N4	0.062 (3)	0.051 (2)	0.057 (3)	−0.019 (2)	−0.021 (2)	−0.001 (2)
C1	0.041 (2)	0.047 (3)	0.043 (3)	−0.016 (2)	−0.017 (2)	0.000 (2)
C2	0.044 (2)	0.039 (2)	0.043 (3)	−0.014 (2)	−0.007 (2)	−0.0030 (19)
C3	0.059 (3)	0.050 (3)	0.035 (2)	−0.030 (2)	−0.011 (2)	−0.002 (2)
C4	0.048 (3)	0.053 (3)	0.039 (2)	−0.024 (2)	−0.015 (2)	0.003 (2)
C5	0.040 (2)	0.039 (2)	0.046 (3)	−0.0119 (19)	−0.017 (2)	−0.0001 (19)
C6	0.037 (2)	0.043 (2)	0.036 (2)	−0.0124 (19)	−0.009 (2)	−0.0067 (19)
C7	0.040 (2)	0.037 (2)	0.045 (3)	−0.0072 (19)	−0.013 (2)	−0.0063 (19)
C8	0.078 (4)	0.043 (3)	0.079 (4)	−0.005 (3)	−0.034 (3)	0.005 (3)
C9	0.112 (5)	0.076 (4)	0.052 (3)	−0.038 (4)	−0.016 (3)	−0.018 (3)
C10	0.050 (3)	0.081 (4)	0.057 (3)	−0.013 (3)	−0.024 (3)	−0.005 (3)
C11	0.047 (3)	0.041 (2)	0.051 (3)	−0.010 (2)	−0.020 (2)	−0.010 (2)
C12	0.059 (3)	0.038 (2)	0.056 (3)	−0.014 (2)	−0.031 (2)	0.001 (2)
C13	0.047 (3)	0.041 (2)	0.049 (3)	−0.020 (2)	−0.015 (2)	−0.003 (2)
C14	0.039 (2)	0.046 (3)	0.042 (2)	−0.016 (2)	−0.012 (2)	−0.002 (2)
C15	0.042 (3)	0.051 (3)	0.050 (3)	−0.016 (2)	−0.014 (2)	−0.008 (2)
C16	0.040 (3)	0.062 (3)	0.039 (2)	−0.018 (2)	−0.011 (2)	−0.012 (2)
C17	0.040 (3)	0.059 (3)	0.038 (2)	−0.011 (2)	−0.010 (2)	−0.006 (2)
C18	0.042 (3)	0.046 (3)	0.040 (2)	−0.013 (2)	−0.006 (2)	−0.007 (2)
C19	0.046 (3)	0.050 (3)	0.040 (2)	−0.020 (2)	−0.011 (2)	−0.006 (2)
C20	0.066 (3)	0.073 (4)	0.063 (3)	−0.028 (3)	−0.026 (3)	−0.017 (3)
C21	0.091 (4)	0.086 (4)	0.054 (4)	−0.005 (3)	−0.024 (3)	0.006 (3)
C22	0.079 (4)	0.051 (3)	0.067 (3)	−0.023 (3)	−0.020 (3)	−0.011 (3)
C23	0.058 (3)	0.074 (4)	0.072 (4)	−0.026 (3)	−0.020 (3)	0.013 (3)
C24	0.127 (7)	0.140 (7)	0.138 (7)	−0.061 (6)	−0.040 (6)	0.082 (6)
C25	0.064 (3)	0.059 (3)	0.061 (3)	−0.015 (3)	−0.018 (3)	−0.008 (3)
C26	0.122 (6)	0.130 (6)	0.088 (5)	−0.010 (5)	−0.003 (4)	−0.061 (5)
Cl1	0.0556 (8)	0.0482 (8)	0.1228 (13)	−0.0165 (6)	−0.0139 (9)	0.0000 (8)
O7	0.096 (3)	0.092 (3)	0.170 (5)	−0.005 (3)	−0.056 (3)	0.015 (3)
O8	0.241 (6)	0.128 (4)	0.180 (5)	−0.090 (4)	−0.064 (5)	−0.029 (4)
O9	0.115 (4)	0.062 (3)	0.216 (5)	−0.036 (3)	−0.077 (4)	0.029 (3)
O10	0.120 (4)	0.152 (5)	0.209 (6)	−0.055 (4)	0.053 (4)	−0.015 (4)

Geometric parameters (Å, º) top

Cu1—N3	1.964 (4)	C10—H10B	0.9600
Cu1—N4	1.975 (4)	C10—H10C	0.9600
Cu1—N2	2.076 (3)	C11—C12	1.511 (6)
Cu1—N1	2.089 (3)	C11—H11A	0.9700
O1—C2	1.367 (5)	C11—H11B	0.9700
O1—C8	1.422 (5)	C12—H12A	0.9700
O2—C3	1.377 (5)	C12—H12B	0.9700
O2—C9	1.420 (6)	C13—C14	1.456 (6)
O3—C4	1.372 (5)	C13—H13	0.9300
O3—C10	1.414 (6)	C14—C15	1.394 (6)
O4—C16	1.372 (5)	C14—C19	1.395 (6)
O4—C20	1.425 (5)	C15—C16	1.378 (6)
O5—C17	1.379 (5)	C15—H15	0.9300
O5—C21	1.413 (6)	C16—C17	1.386 (6)
O6—C18	1.366 (5)	C17—C18	1.400 (6)
O6—C22	1.426 (5)	C18—C19	1.382 (6)
N1—C7	1.274 (5)	C19—H19	0.9300
N1—C11	1.475 (5)	C20—H20A	0.9600
N2—C13	1.277 (5)	C20—H20B	0.9600
N2—C12	1.468 (5)	C20—H20C	0.9600
N3—C25	1.115 (6)	C21—H21A	0.9600
N4—C23	1.108 (6)	C21—H21B	0.9600
C1—C6	1.382 (6)	C21—H21C	0.9600
C1—C2	1.385 (6)	C22—H22A	0.9600
C1—H1	0.9300	C22—H22B	0.9600
C2—C3	1.398 (6)	C22—H22C	0.9600
C3—C4	1.387 (6)	C23—C24	1.463 (8)
C4—C5	1.385 (6)	C24—H24A	0.9600
C5—C6	1.390 (5)	C24—H24B	0.9600
C5—H5	0.9300	C24—H24C	0.9600
C6—C7	1.465 (5)	C25—C26	1.449 (8)
C7—H7	0.9300	C26—H26A	0.9600
C8—H8A	0.9600	C26—H26B	0.9600
C8—H8B	0.9600	C26—H26C	0.9600
C8—H8C	0.9600	Cl1—O10	1.387 (4)
C9—H9A	0.9600	Cl1—O9	1.410 (4)
C9—H9B	0.9600	Cl1—O7	1.422 (4)
C9—H9C	0.9600	Cl1—O8	1.436 (4)
C10—H10A	0.9600

N3—Cu1—N4	103.04 (16)	N2—C12—C11	109.3 (3)
N3—Cu1—N2	115.70 (15)	N2—C12—H12A	109.8
N4—Cu1—N2	120.15 (14)	C11—C12—H12A	109.8
N3—Cu1—N1	120.65 (14)	N2—C12—H12B	109.8
N4—Cu1—N1	112.89 (15)	C11—C12—H12B	109.8
N2—Cu1—N1	84.97 (13)	H12A—C12—H12B	108.3
C2—O1—C8	117.0 (3)	N2—C13—C14	126.6 (4)
C3—O2—C9	114.4 (4)	N2—C13—H13	116.7
C4—O3—C10	116.4 (3)	C14—C13—H13	116.7
C16—O4—C20	116.7 (4)	C15—C14—C19	119.9 (4)
C17—O5—C21	114.5 (4)	C15—C14—C13	116.3 (4)
C18—O6—C22	117.5 (4)	C19—C14—C13	123.8 (4)
C7—N1—C11	115.9 (3)	C16—C15—C14	120.1 (4)
C7—N1—Cu1	137.8 (3)	C16—C15—H15	119.9
C11—N1—Cu1	105.8 (2)	C14—C15—H15	119.9
C13—N2—C12	116.2 (3)	O4—C16—C15	123.6 (4)
C13—N2—Cu1	137.6 (3)	O4—C16—C17	115.9 (4)
C12—N2—Cu1	105.3 (2)	C15—C16—C17	120.4 (4)
C25—N3—Cu1	174.3 (4)	O5—C17—C16	121.9 (4)
C23—N4—Cu1	175.7 (4)	O5—C17—C18	118.5 (4)
C6—C1—C2	119.5 (4)	C16—C17—C18	119.5 (4)
C6—C1—H1	120.2	O6—C18—C19	124.5 (4)
C2—C1—H1	120.2	O6—C18—C17	115.2 (4)
O1—C2—C1	124.6 (4)	C19—C18—C17	120.3 (4)
O1—C2—C3	115.3 (4)	C18—C19—C14	119.7 (4)
C1—C2—C3	120.1 (4)	C18—C19—H19	120.2
O2—C3—C4	120.6 (4)	C14—C19—H19	120.2
O2—C3—C2	119.3 (4)	O4—C20—H20A	109.5
C4—C3—C2	120.0 (4)	O4—C20—H20B	109.5
O3—C4—C5	124.6 (4)	H20A—C20—H20B	109.5
O3—C4—C3	115.8 (4)	O4—C20—H20C	109.5
C5—C4—C3	119.6 (4)	H20A—C20—H20C	109.5
C4—C5—C6	120.2 (4)	H20B—C20—H20C	109.5
C4—C5—H5	119.9	O5—C21—H21A	109.5
C6—C5—H5	119.9	O5—C21—H21B	109.5
C1—C6—C5	120.5 (4)	H21A—C21—H21B	109.5
C1—C6—C7	123.4 (4)	O5—C21—H21C	109.5
C5—C6—C7	116.0 (4)	H21A—C21—H21C	109.5
N1—C7—C6	125.5 (4)	H21B—C21—H21C	109.5
N1—C7—H7	117.2	O6—C22—H22A	109.5
C6—C7—H7	117.2	O6—C22—H22B	109.5
O1—C8—H8A	109.5	H22A—C22—H22B	109.5
O1—C8—H8B	109.5	O6—C22—H22C	109.5
H8A—C8—H8B	109.5	H22A—C22—H22C	109.5
O1—C8—H8C	109.5	H22B—C22—H22C	109.5
H8A—C8—H8C	109.5	N4—C23—C24	178.9 (7)
H8B—C8—H8C	109.5	C23—C24—H24A	109.5
O2—C9—H9A	109.5	C23—C24—H24B	109.5
O2—C9—H9B	109.5	H24A—C24—H24B	109.5
H9A—C9—H9B	109.5	C23—C24—H24C	109.5
O2—C9—H9C	109.5	H24A—C24—H24C	109.5
H9A—C9—H9C	109.5	H24B—C24—H24C	109.5
H9B—C9—H9C	109.5	N3—C25—C26	178.9 (6)
O3—C10—H10A	109.5	C25—C26—H26A	109.5
O3—C10—H10B	109.5	C25—C26—H26B	109.5
H10A—C10—H10B	109.5	H26A—C26—H26B	109.5
O3—C10—H10C	109.5	C25—C26—H26C	109.5
H10A—C10—H10C	109.5	H26A—C26—H26C	109.5
H10B—C10—H10C	109.5	H26B—C26—H26C	109.5
N1—C11—C12	108.6 (3)	O10—Cl1—O9	112.7 (3)
N1—C11—H11A	110.0	O10—Cl1—O7	111.7 (4)
C12—C11—H11A	110.0	O9—Cl1—O7	108.6 (3)
N1—C11—H11B	110.0	O10—Cl1—O8	106.8 (4)
C12—C11—H11B	110.0	O9—Cl1—O8	109.3 (3)
H11A—C11—H11B	108.4	O7—Cl1—O8	107.5 (3)

N3—Cu1—N1—C7	−40.7 (5)	C4—C5—C6—C7	−175.5 (4)
N4—Cu1—N1—C7	81.7 (5)	C11—N1—C7—C6	−176.6 (4)
N2—Cu1—N1—C7	−157.7 (4)	Cu1—N1—C7—C6	−6.1 (7)
N3—Cu1—N1—C11	130.4 (3)	C1—C6—C7—N1	−16.5 (7)
N4—Cu1—N1—C11	−107.2 (3)	C5—C6—C7—N1	161.2 (4)
N2—Cu1—N1—C11	13.5 (3)	C7—N1—C11—C12	133.0 (4)
N3—Cu1—N2—C13	86.2 (5)	Cu1—N1—C11—C12	−40.4 (4)
N4—Cu1—N2—C13	−38.5 (5)	C13—N2—C12—C11	128.1 (4)
N1—Cu1—N2—C13	−152.1 (5)	Cu1—N2—C12—C11	−43.2 (4)
N3—Cu1—N2—C12	−105.5 (3)	N1—C11—C12—N2	58.1 (4)
N4—Cu1—N2—C12	129.8 (3)	C12—N2—C13—C14	−177.9 (4)
N1—Cu1—N2—C12	16.2 (3)	Cu1—N2—C13—C14	−10.5 (7)
N4—Cu1—N3—C25	−27 (4)	N2—C13—C14—C15	168.6 (4)
N2—Cu1—N3—C25	−160 (4)	N2—C13—C14—C19	−11.8 (7)
N1—Cu1—N3—C25	100 (4)	C19—C14—C15—C16	2.5 (6)
N3—Cu1—N4—C23	13 (6)	C13—C14—C15—C16	−177.9 (4)
N2—Cu1—N4—C23	143 (6)	C20—O4—C16—C15	0.7 (6)
N1—Cu1—N4—C23	−119 (6)	C20—O4—C16—C17	−178.5 (4)
C8—O1—C2—C1	−11.7 (6)	C14—C15—C16—O4	−179.6 (4)
C8—O1—C2—C3	168.5 (4)	C14—C15—C16—C17	−0.4 (7)
C6—C1—C2—O1	178.7 (4)	C21—O5—C17—C16	−76.3 (6)
C6—C1—C2—C3	−1.6 (6)	C21—O5—C17—C18	106.9 (5)
C9—O2—C3—C4	−81.4 (5)	O4—C16—C17—O5	0.1 (6)
C9—O2—C3—C2	102.2 (5)	C15—C16—C17—O5	−179.1 (4)
O1—C2—C3—O2	−1.0 (6)	O4—C16—C17—C18	176.9 (4)
C1—C2—C3—O2	179.2 (4)	C15—C16—C17—C18	−2.4 (7)
O1—C2—C3—C4	−177.5 (4)	C22—O6—C18—C19	−5.9 (6)
C1—C2—C3—C4	2.8 (6)	C22—O6—C18—C17	174.7 (4)
C10—O3—C4—C5	4.6 (6)	O5—C17—C18—O6	−0.6 (6)
C10—O3—C4—C3	−174.6 (4)	C16—C17—C18—O6	−177.4 (4)
O2—C3—C4—O3	1.4 (6)	O5—C17—C18—C19	180.0 (4)
C2—C3—C4—O3	177.8 (4)	C16—C17—C18—C19	3.2 (6)
O2—C3—C4—C5	−177.9 (4)	O6—C18—C19—C14	179.5 (4)
C2—C3—C4—C5	−1.4 (6)	C17—C18—C19—C14	−1.1 (6)
O3—C4—C5—C6	179.8 (4)	C15—C14—C19—C18	−1.7 (6)
C3—C4—C5—C6	−1.1 (6)	C13—C14—C19—C18	178.7 (4)
C2—C1—C6—C5	−0.9 (6)	Cu1—N4—C23—C24	−151 (34)
C2—C1—C6—C7	176.6 (4)	Cu1—N3—C25—C26	−87 (36)
C4—C5—C6—C1	2.3 (6)

Experimental details

Crystal data
Chemical formula	[Cu(C₂H₃N)₂(C₂₂H₂₈N₂O₆)]ClO₄
M_r	661.56
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	9.869 (2), 11.903 (3), 14.904 (3)
α, β, γ (°)	80.537 (4), 71.677 (4), 68.285 (4)
V (Å³)	1541.9 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.85
Crystal size (mm)	0.24 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.821, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	8034, 5414, 3408
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.141, 1.01
No. of reflections	5414
No. of parameters	387
No. of restraints	34
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.37

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

References

Amirnasr, M., Khalaji, A. D. & Falvello, L. R. (2006). Inorg. Chim. Acta, 359, 713–717. CrossRef CAS Google Scholar
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Chowdhury, S., Patra, G. K., Drew, M. G. B., Chattopadhyay, N. & Datta, D. (2000). J. Chem. Soc. Dalton Trans. pp. 235–237. Web of Science CSD CrossRef Google Scholar
Dakin, L. A., Ong, P. C., Panek, J. S., Staples, R. J. & Stavropoulos, P. (2000). Organometallics, 19, 2896–2908. Web of Science CSD CrossRef CAS Google Scholar
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