Bis[3-ethyl-4-(4-methoxy­phen­yl)-5-(2-pyrid­yl)-4H-1,2,4-triazole-κ2N1,N5]bis­(perchlorato-κO)copper(II) acetonitrile disolvate

Huang, L.; Wang, Z.; Zhang, X.; Wu, P.

doi:10.1107/S1600536808012026

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages m741-m742

doi:10.1107/S1600536808012026

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Bis[3-ethyl-4-(4-methoxyphenyl)-5-(2-pyridyl)-4H-1,2,4-triazole-κ²N¹,N⁵]bis(perchlorato-κO)copper(II) acetonitrile disolvate

Liaocheng Huang,^a Zuoxiang Wang,^a ^* Xiaoming Zhang ^a and Pingfeng Wu ^a

^aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: wangzx0908@yahoo.com.cn

(Received 25 March 2008; accepted 25 April 2008; online 30 April 2008)

In the title compound, [Cu(ClO₄)₂(C₁₆H₁₆N₄O)₂]·2CH₃CN, the Cu^II atom, located on an inversion center, is in a tetragonally distorted octahedral environment, coordinated by four N atoms of two bidentate 3-ethyl-4-(4-methoxyphenyl)-5-(2-pyridyl)-4H-1,2,4-triazole ligands in equatorial positions and by the O atoms of two perchlorate groups in axial positions. The long axial Cu—O bond of 2.4743 (17) Å is the result of the Jahn–Teller effect.

Related literature

For related literature, see: Bencini et al. (1987 ); Garcia et al. (1997 ); Kahn & Martinez (1998 ); Klingele et al. (2005 , 2006 ); Koningsbruggen (2004 ); Koningsbruggen et al. (1995 ); Lavrenova & Larionov (1998 ); Matouzenko et al. (2004 ); Moliner et al. (1998 , 2001 ); Wang et al. (2005 ); Zhou et al., (2006a ,b ).

Experimental

Crystal data

[Cu(ClO₄)₂(C₁₆H₁₆N₄O)₂]·2C₂H₃N
M_r = 905.21
Triclinic, $[P \overline 1]$
a = 8.3286 (11) Å
b = 9.1266 (14) Å
c = 14.225 (2) Å
α = 100.516 (7)°
β = 101.067 (4)°
γ = 98.780 (4)°
V = 1023.4 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.73 mm⁻¹
T = 293 (2) K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.864, T_max = 0.867
8302 measured reflections
3565 independent reflections
3170 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.120
S = 1.16
3565 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—N2	1.9892 (16)
Cu1—N1	2.0261 (18)
Cu1—O2	2.4743 (17)

N2ⁱ—Cu1—N2	180
N2ⁱ—Cu1—N1	99.31 (7)
N2—Cu1—N1	80.69 (7)
N1—Cu1—N1ⁱ	180
N2ⁱ—Cu1—O2	92.07 (7)
N2—Cu1—O2	87.93 (7)
N1—Cu1—O2	92.61 (7)
N1ⁱ—Cu1—O2	87.39 (7)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012026/gk2140sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012026/gk2140Isup2.hkl

checkCIF report

Comment top

1,2,4-Triazole derivatives can be used as bridging ligands in transition metal coordination chemistry (Bencini et al., 1987; Koningsbruggen et al., 1995; Moliner et al., 1998, 2001; Klingele et al., 2005, 2006). Some spin-crossover complexes of 1,2,4-triazoles with iron(II) salts have been reported with potential applications as molecular-based memory devices, displays and optical switches (Garcia et al., 1997; Lavrenova & Larionov, 1998; Kahn & Martinez, 1998; Koningsbruggen 2004; Matouzenko et al., 2004). Recently we have reported synthesis of some new 3,4-disubstituted-5-(2-pyridyl)-1,2,4-triazole ligands and crystal structures of their transition-metal complexes (Wang et al., 2005; Zhou et al., 2006a,b). Here we report the crystal structure of the title compound (Fig. 1). The Cu^II atom is located on an inversion center. It shows a tetragonally distorted octahedral coordination geometry and is coordinated by two bis-chelating 3-ethyl-4-(4-methoxyphenyl)-5-(2-pyridyl)-1,2,4-triazole ligands with the CuN₂N'₂ chromophore in the equatorial plane and two O atoms of two perchlorate groups in axial positions.

Related literature top

For related literature, see: Bencini et al. (1987); Garcia et al. (1997); Kahn & Martinez (1998); Klingele et al. (2005, 2006); Koningsbruggen (2004); Koningsbruggen et al. (1995); Lavrenova & Larionov (1998); Matouzenko et al. (2004); Moliner et al. (1998, 2001); Wang et al. (2005); Zhou et al., (2006a,b).

Experimental top

The title compound was prepared by the reaction of 3-ethyl-4-(4-methoxyphenyl)-5-(2-pyridyl)-1,2,4-triazole with copper(II) perchlorate in acetonitrile. To a warm solution of 3-ethyl-4-(4-methoxyphenyl)-5-(2-pyridyl)-1,2,4-triazole (1.120 g, 4.0 mmol) in 20 ml acetonitrile, copper(II) perchlorate (0.525 g, 2.0 mmol) was added. After several days blue single crystals suitable for X-ray analysis were collected.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids shown at the 30% probability level. Symmetry code (i):-x + 1,-y + 1,-z + 1

Bis[3-ethyl-4-(4-methoxyphenyl)-5-(2-pyridyl)-4H-1,2,4-triazole- κ²N¹,N⁵]bis(perchlorato-κO)copper(II) acetonitrile disolvate top

Crystal data top

[Cu(ClO₄)₂(C₁₆H₁₆N₄O)₂]·2C₂H₃N	Z = 1
M_r = 905.21	F(000) = 467
Triclinic, P1	D_x = 1.469 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3286 (11) Å	Cell parameters from 2714 reflections
b = 9.1266 (14) Å	θ = 3.1–27.5°
c = 14.225 (2) Å	µ = 0.73 mm⁻¹
α = 100.516 (7)°	T = 293 K
β = 101.067 (4)°	Prism, blue
γ = 98.780 (4)°	0.20 × 0.20 × 0.20 mm
V = 1023.4 (3) Å³

Data collection top

Rigaku Mercury2 diffractometer	3565 independent reflections
Radiation source: fine-focus sealed tube	3170 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 13.6612 pixels mm^-1	θ_max = 25.0°, θ_min = 2.3°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −10→10
T_min = 0.864, T_max = 0.867	l = −16→16
8302 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0739P)²] where P = (F_o² + 2F_c²)/3
3565 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[Cu(ClO₄)₂(C₁₆H₁₆N₄O)₂]·2C₂H₃N	γ = 98.780 (4)°
M_r = 905.21	V = 1023.4 (3) Å³
Triclinic, P1	Z = 1
a = 8.3286 (11) Å	Mo Kα radiation
b = 9.1266 (14) Å	µ = 0.73 mm⁻¹
c = 14.225 (2) Å	T = 293 K
α = 100.516 (7)°	0.20 × 0.20 × 0.20 mm
β = 101.067 (4)°

Data collection top

Rigaku Mercury2 diffractometer	3565 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3170 reflections with I > 2σ(I)
T_min = 0.864, T_max = 0.867	R_int = 0.031
8302 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.16	Δρ_max = 0.46 e Å⁻³
3565 reflections	Δρ_min = −0.54 e Å⁻³
271 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	0.5000	0.5000	0.5000	0.03204 (16)
Cl1	0.54072 (7)	0.50192 (6)	0.25312 (4)	0.04015 (18)
O1	−0.0616 (2)	−0.3362 (2)	0.02788 (13)	0.0619 (5)
O2	0.6082 (2)	0.5545 (2)	0.35718 (12)	0.0508 (4)
O3	0.4928 (4)	0.3415 (2)	0.23080 (16)	0.0795 (7)
O4	0.6656 (3)	0.5460 (3)	0.20330 (15)	0.0827 (8)
O5	0.4003 (3)	0.5667 (3)	0.2258 (2)	0.0942 (8)
N1	0.2619 (2)	0.43579 (19)	0.42008 (13)	0.0325 (4)
N2	0.4977 (2)	0.28147 (18)	0.44924 (13)	0.0329 (4)
N3	0.6125 (2)	0.1869 (2)	0.45117 (13)	0.0370 (4)
N4	0.3825 (2)	0.07416 (18)	0.34047 (12)	0.0315 (4)
N5	0.7131 (5)	0.9957 (4)	0.1193 (3)	0.1093 (12)
C1	0.5401 (3)	0.0628 (2)	0.38456 (15)	0.0354 (5)
C2	0.3617 (3)	0.2129 (2)	0.38257 (14)	0.0302 (5)
C3	0.2210 (3)	0.2907 (2)	0.36606 (15)	0.0305 (4)
C4	0.0646 (3)	0.2305 (3)	0.30709 (16)	0.0401 (5)
H1	0.0398	0.1314	0.2703	0.048*
C5	−0.0554 (3)	0.3207 (3)	0.30364 (18)	0.0455 (6)
H2	−0.1622	0.2825	0.2647	0.055*
C6	−0.0147 (3)	0.4656 (3)	0.35806 (19)	0.0470 (6)
H3	−0.0940	0.5272	0.3566	0.056*
C7	0.1451 (3)	0.5213 (2)	0.41562 (17)	0.0410 (5)
H4	0.1716	0.6208	0.4521	0.049*
C8	0.2691 (3)	−0.0342 (2)	0.25825 (15)	0.0317 (5)
C9	0.2728 (3)	−0.0173 (3)	0.16435 (16)	0.0419 (6)
H5	0.3484	0.0613	0.1543	0.050*
C10	0.1638 (3)	−0.1176 (3)	0.08535 (17)	0.0467 (6)
H10A	0.1665	−0.1073	0.0218	0.056*
C11	0.0513 (3)	−0.2327 (3)	0.10070 (17)	0.0425 (6)
C12	0.0493 (3)	−0.2497 (3)	0.19559 (19)	0.0491 (6)
H12A	−0.0261	−0.3281	0.2059	0.059*
C13	0.1592 (3)	−0.1503 (3)	0.27446 (17)	0.0433 (6)
H13A	0.1589	−0.1618	0.3381	0.052*
C14	−0.0529 (5)	−0.3328 (4)	−0.0708 (2)	0.0801 (11)
H14A	−0.1345	−0.4146	−0.1148	0.120*
H14B	0.0564	−0.3439	−0.0795	0.120*
H14C	−0.0748	−0.2377	−0.0845	0.120*
C15	0.6135 (3)	−0.0739 (3)	0.3591 (2)	0.0476 (6)
H15A	0.6122	−0.0932	0.2896	0.057*
H15B	0.5440	−0.1609	0.3710	0.057*
C16	0.7893 (3)	−0.0596 (3)	0.4159 (2)	0.0558 (7)
H16A	0.8271	−0.1528	0.3978	0.084*
H16B	0.7922	−0.0392	0.4849	0.084*
H16C	0.8606	0.0221	0.4013	0.084*
C17	0.6382 (5)	0.8821 (5)	0.0784 (3)	0.0736 (9)
C18	0.5389 (5)	0.7344 (4)	0.0255 (3)	0.0826 (10)
H18A	0.4634	0.6987	0.0633	0.124*
H18B	0.6113	0.6636	0.0150	0.124*
H18C	0.4766	0.7434	−0.0367	0.124*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0291 (2)	0.0242 (2)	0.0355 (2)	0.00483 (15)	−0.00289 (16)	−0.00093 (16)
Cl1	0.0357 (3)	0.0382 (3)	0.0421 (3)	0.0009 (2)	0.0040 (2)	0.0079 (3)
O1	0.0567 (12)	0.0558 (11)	0.0491 (11)	−0.0125 (9)	−0.0083 (9)	−0.0088 (9)
O2	0.0526 (11)	0.0506 (10)	0.0418 (9)	0.0000 (8)	0.0062 (8)	0.0047 (8)
O3	0.135 (2)	0.0369 (10)	0.0564 (12)	−0.0054 (12)	0.0259 (13)	−0.0023 (9)
O4	0.0610 (14)	0.126 (2)	0.0611 (12)	−0.0114 (13)	0.0182 (11)	0.0415 (14)
O5	0.0570 (14)	0.0994 (18)	0.1069 (19)	0.0306 (13)	−0.0222 (13)	0.0044 (16)
N1	0.0316 (9)	0.0288 (9)	0.0332 (9)	0.0056 (7)	0.0016 (7)	0.0032 (7)
N2	0.0332 (10)	0.0277 (9)	0.0323 (9)	0.0052 (7)	−0.0005 (8)	0.0016 (7)
N3	0.0376 (10)	0.0279 (9)	0.0399 (10)	0.0092 (8)	−0.0005 (8)	0.0008 (8)
N4	0.0342 (10)	0.0241 (8)	0.0312 (9)	0.0021 (7)	0.0023 (7)	0.0014 (7)
N5	0.121 (3)	0.095 (3)	0.104 (3)	−0.002 (2)	0.036 (2)	0.009 (2)
C1	0.0390 (12)	0.0282 (11)	0.0342 (11)	0.0045 (9)	0.0036 (9)	0.0016 (9)
C2	0.0335 (11)	0.0241 (9)	0.0294 (10)	0.0017 (8)	0.0044 (9)	0.0027 (8)
C3	0.0315 (11)	0.0270 (10)	0.0290 (10)	0.0018 (8)	0.0023 (8)	0.0041 (8)
C4	0.0364 (12)	0.0352 (12)	0.0407 (12)	0.0016 (10)	0.0008 (10)	0.0012 (10)
C5	0.0300 (12)	0.0494 (14)	0.0483 (14)	0.0028 (10)	−0.0041 (10)	0.0062 (12)
C6	0.0347 (12)	0.0467 (13)	0.0552 (14)	0.0142 (11)	−0.0007 (11)	0.0062 (12)
C7	0.0379 (13)	0.0329 (11)	0.0475 (13)	0.0090 (10)	0.0033 (11)	0.0021 (10)
C8	0.0346 (11)	0.0238 (10)	0.0308 (10)	0.0027 (9)	0.0023 (9)	−0.0011 (8)
C9	0.0464 (13)	0.0348 (12)	0.0366 (12)	−0.0056 (10)	0.0059 (10)	0.0023 (10)
C10	0.0569 (16)	0.0456 (13)	0.0295 (11)	−0.0004 (12)	0.0035 (11)	0.0031 (10)
C11	0.0409 (13)	0.0345 (11)	0.0393 (12)	0.0012 (10)	−0.0031 (10)	−0.0064 (10)
C12	0.0502 (15)	0.0362 (12)	0.0514 (14)	−0.0105 (11)	0.0104 (12)	0.0022 (11)
C13	0.0509 (14)	0.0363 (12)	0.0359 (12)	−0.0048 (11)	0.0089 (11)	0.0028 (10)
C14	0.093 (3)	0.072 (2)	0.0437 (16)	−0.0080 (19)	−0.0183 (16)	−0.0116 (15)
C15	0.0515 (15)	0.0332 (12)	0.0524 (14)	0.0174 (11)	0.0020 (12)	−0.0022 (11)
C16	0.0468 (15)	0.0451 (14)	0.0750 (19)	0.0169 (12)	0.0103 (14)	0.0091 (13)
C17	0.078 (2)	0.085 (2)	0.0633 (19)	0.016 (2)	0.0250 (18)	0.0214 (19)
C18	0.092 (3)	0.087 (3)	0.069 (2)	0.019 (2)	0.0183 (19)	0.0167 (19)

Geometric parameters (Å, º) top

Cu1—N2ⁱ	1.9892 (16)	C6—C7	1.387 (3)
Cu1—N2	1.9892 (16)	C6—H3	0.9300
Cu1—N1	2.0261 (18)	C7—H4	0.9300
Cu1—N1ⁱ	2.0261 (18)	C8—C13	1.375 (3)
Cu1—O2	2.4743 (17)	C8—C9	1.378 (3)
Cl1—O5	1.410 (2)	C9—C10	1.380 (3)
Cl1—O4	1.416 (2)	C9—H5	0.9300
Cl1—O3	1.416 (2)	C10—C11	1.376 (3)
Cl1—O2	1.4409 (18)	C10—H10A	0.9300
O1—C11	1.359 (3)	C11—C12	1.389 (4)
O1—C14	1.425 (4)	C12—C13	1.378 (3)
N1—C7	1.336 (3)	C12—H12A	0.9300
N1—C3	1.360 (3)	C13—H13A	0.9300
N2—C2	1.315 (3)	C14—H14A	0.9600
N2—N3	1.382 (2)	C14—H14B	0.9600
N3—C1	1.313 (3)	C14—H14C	0.9600
N4—C2	1.349 (2)	C15—C16	1.504 (4)
N4—C1	1.370 (3)	C15—H15A	0.9700
N4—C8	1.451 (2)	C15—H15B	0.9700
N5—C17	1.116 (5)	C16—H16A	0.9600
C1—C15	1.488 (3)	C16—H16B	0.9600
C2—C3	1.463 (3)	C16—H16C	0.9600
C3—C4	1.377 (3)	C17—C18	1.455 (5)
C4—C5	1.387 (3)	C18—H18A	0.9600
C4—H1	0.9300	C18—H18B	0.9600
C5—C6	1.361 (3)	C18—H18C	0.9600
C5—H2	0.9300

N2ⁱ—Cu1—N2	180.0	N1—C7—C6	121.7 (2)
N2ⁱ—Cu1—N1	99.31 (7)	N1—C7—H4	119.1
N2—Cu1—N1	80.69 (7)	C6—C7—H4	119.1
N2ⁱ—Cu1—N1ⁱ	80.69 (7)	C13—C8—C9	120.95 (19)
N2—Cu1—N1ⁱ	99.31 (7)	C13—C8—N4	120.21 (18)
N1—Cu1—N1ⁱ	180.0	C9—C8—N4	118.83 (18)
N2ⁱ—Cu1—O2	92.07 (7)	C8—C9—C10	119.6 (2)
N2—Cu1—O2	87.93 (7)	C8—C9—H5	120.2
N1—Cu1—O2	92.61 (7)	C10—C9—H5	120.2
N1ⁱ—Cu1—O2	87.39 (7)	C11—C10—C9	119.9 (2)
O5—Cl1—O4	110.60 (17)	C11—C10—H10A	120.0
O5—Cl1—O3	109.64 (17)	C9—C10—H10A	120.0
O4—Cl1—O3	109.77 (15)	O1—C11—C10	124.3 (2)
O5—Cl1—O2	109.11 (14)	O1—C11—C12	115.6 (2)
O4—Cl1—O2	108.51 (12)	C10—C11—C12	120.0 (2)
O3—Cl1—O2	109.19 (12)	C13—C12—C11	120.0 (2)
C11—O1—C14	117.6 (2)	C13—C12—H12A	120.0
Cl1—O2—Cu1	131.53 (10)	C11—C12—H12A	120.0
C7—N1—C3	118.35 (18)	C8—C13—C12	119.4 (2)
C7—N1—Cu1	126.54 (14)	C8—C13—H13A	120.3
C3—N1—Cu1	115.11 (14)	C12—C13—H13A	120.3
C2—N2—N3	109.04 (16)	O1—C14—H14A	109.5
C2—N2—Cu1	112.95 (14)	O1—C14—H14B	109.5
N3—N2—Cu1	136.71 (14)	H14A—C14—H14B	109.5
C1—N3—N2	105.81 (18)	O1—C14—H14C	109.5
C2—N4—C1	105.79 (17)	H14A—C14—H14C	109.5
C2—N4—C8	127.23 (18)	H14B—C14—H14C	109.5
C1—N4—C8	126.67 (17)	C1—C15—C16	113.9 (2)
N3—C1—N4	110.41 (18)	C1—C15—H15A	108.8
N3—C1—C15	126.3 (2)	C16—C15—H15A	108.8
N4—C1—C15	123.28 (19)	C1—C15—H15B	108.8
N2—C2—N4	108.94 (18)	C16—C15—H15B	108.8
N2—C2—C3	119.51 (17)	H15A—C15—H15B	107.7
N4—C2—C3	131.54 (18)	C15—C16—H16A	109.5
N1—C3—C4	122.13 (19)	C15—C16—H16B	109.5
N1—C3—C2	110.79 (17)	H16A—C16—H16B	109.5
C4—C3—C2	127.06 (18)	C15—C16—H16C	109.5
C3—C4—C5	118.8 (2)	H16A—C16—H16C	109.5
C3—C4—H1	120.6	H16B—C16—H16C	109.5
C5—C4—H1	120.6	N5—C17—C18	179.4 (5)
C6—C5—C4	119.1 (2)	C17—C18—H18A	109.5
C6—C5—H2	120.4	C17—C18—H18B	109.5
C4—C5—H2	120.4	H18A—C18—H18B	109.5
C5—C6—C7	119.9 (2)	C17—C18—H18C	109.5
C5—C6—H3	120.0	H18A—C18—H18C	109.5
C7—C6—H3	120.0	H18B—C18—H18C	109.5

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(ClO₄)₂(C₁₆H₁₆N₄O)₂]·2C₂H₃N
M_r	905.21
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.3286 (11), 9.1266 (14), 14.225 (2)
α, β, γ (°)	100.516 (7), 101.067 (4), 98.780 (4)
V (Å³)	1023.4 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.864, 0.867
No. of measured, independent and observed [I > 2σ(I)] reflections	8302, 3565, 3170
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.120, 1.16
No. of reflections	3565
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.54

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu1—N2	1.9892 (16)	Cu1—O2	2.4743 (17)
Cu1—N1	2.0261 (18)

N2ⁱ—Cu1—N2	180.0	N2ⁱ—Cu1—O2	92.07 (7)
N2ⁱ—Cu1—N1	99.31 (7)	N2—Cu1—O2	87.93 (7)
N2—Cu1—N1	80.69 (7)	N1—Cu1—O2	92.61 (7)
N1—Cu1—N1ⁱ	180.0	N1ⁱ—Cu1—O2	87.39 (7)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We are grateful to Jingye Pharmochemical Pilot Plant for financial assistance through project 8507041056.

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