Bis[3-ethyl-4-(4-methoxy-phen-yl)-5-(2-pyrid-yl)-4H-1,2,4-triazole-κN,N]bis-(perchlorato-κO)copper(II) acetonitrile disolvate.

In the title compound, [Cu(ClO(4))(2)(C(16)H(16)N(4)O)(2)]·2CH(3)CN, the Cu(II) atom, located on an inversion center, is in a tetra-gonally distorted octa-hedral environment, coordinated by four N atoms of two bidentate 3-ethyl-4-(4-methoxy-phen-yl)-5-(2-pyrid-yl)-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 = 905.21

Triclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.120

S = 1.16

3565 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.54 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(ClO4)2(C16H16N4O)2]·2C2H3N	Z = 1
Mr = 905.21	F000 = 467
Triclinic, P1	Dx = 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 = 3.1–27.5º
c = 14.225 (2) Å	µ = 0.73 mm−1
α = 100.516 (7)º	T = 293 (2) K
β = 101.067 (4)º	Prism, blue
γ = 98.780 (4)º	0.20 × 0.20 × 0.20 mm
V = 1023.4 (3) Å3

Rigaku Mercury2 diffractometer	3565 independent reflections
Radiation source: fine-focus sealed tube	3170 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
Detector resolution: 13.6612 pixels mm-1	θmax = 25.0º
T = 293(2) K	θmin = 2.3º
ω scans	h = −9→9
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	k = −10→10
Tmin = 0.864, Tmax = 0.867	l = −16→16
8302 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0739P)2] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max < 0.001
3565 reflections	Δρmax = 0.46 e Å−3
271 parameters	Δρmin = −0.54 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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) .