Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, [Cu(C16H16N4)2](ClO4)2, the CuII atom lies on an inversion centre and has a distorted square-planar geometry. In each ligand, the dihedral angle between the triazole and pyridine rings is 9.1 (3)°, and that between the triazole and benzene rings is 85.01 (14)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057686/cf2155sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057686/cf2155Isup2.hkl
Contains datablock I

CCDC reference: 672690

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.058
  • wR factor = 0.127
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (2) 2.22 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

The coordination chemistry of 1,2,4-triazole derivatives has attracted great attention in recent years (Bencini et al., 1987; Koningsbruggen et al., 1995; Moliner et al., 1998; Moliner et al., 2001; Klingele & Brooker 2003; Klingele et al., 2005). Some spin-crossover complexes of 1,2,4-triazoles with iron(II) salts have been reported, which could be used 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). We report here the crystal structure analysis of the title compound, (I).

The structure of (I) is shown in Fig.1. In the crystal structure, the CuII atom lies on an inversion centre and is coordinated by two 3-ethyl-4-(p-methylphenyl)-5-(2-pyridyl)-1,2,4-triazole ligands in a distorted square-planar geometry. In each ligand, the dihedral angle between the triazole and pyridine rings is 9.1 (3)°, and that between the triazole and benzene rings is 85.01 (14)°.

Related literature top

For related literature, see: Bencini et al. (1987); Garcia et al. (1997); Kahn & Martinez (1998); Klingele & Brooker (2003); Klingele et al. (2005); Koningsbruggen (2004); Koningsbruggen et al. (1995); Lavrenova & Larionov (1998); Matouzenko et al. (2004); Moliner et al. (1998, 2001).

Experimental top

The title compound was prepared by reaction of 3-ethyl-4-(p-methylphenyl)-5-(2-pyridyl)-1,2,4-triazole with copper(II) perchlorate in acetonitrile and water. To a warm solution of 1.06 grams of 3-ethyl-4-(p-methylphenyl)-5-(2-pyridyl)-1,2,4-triazole (4.0 mmol) in 20 ml acetonitrile-water (V/V = 1:1), 0.52 grams of copper(II) perchlorate (2.0 mmol) was added. The filtrate was left to stand at room temperature for several days, and single crystals suitable for X-ray diffraction were collected.

Refinement top

All H atoms were located in a difference Fourier map and allowed to ride on their parent atoms at distances of 0.93Å (aromatic), 0.96Å (methyl) and 0.97Å (methylene), and with Uiso(H) values of 1.2 or 1.5 times Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atomic labelling. Displacement ellipsoids are shown at the 30% probability level.
Bis[3-ethyl-4-(4-methylphenyl)-5-(2-pyridyl)-4H-1,2,4-triazole-\k2N,N']copper(II) bis(perchlorate) top
Crystal data top
[Cu(C16H16N4)2](ClO4)2Z = 1
Mr = 791.10F(000) = 407
Triclinic, P1Dx = 1.534 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0113 (14) ÅCell parameters from 1954 reflections
b = 8.3126 (14) Åθ = 2.6–25.9°
c = 14.215 (3) ŵ = 0.86 mm1
α = 99.374 (3)°T = 291 K
β = 102.689 (3)°Block, blue
γ = 107.041 (2)°0.26 × 0.20 × 0.18 mm
V = 856.4 (3) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer
3294 independent reflections
Radiation source: sealed tube2297 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ϕ and ω scansθmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 99
Tmin = 0.808, Tmax = 0.861k = 104
4686 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0658P)2]
where P = (Fo2 + 2Fc2)/3
3294 reflections(Δ/σ)max < 0.001
234 parametersΔρmax = 0.82 e Å3
1 restraintΔρmin = 0.47 e Å3
Crystal data top
[Cu(C16H16N4)2](ClO4)2γ = 107.041 (2)°
Mr = 791.10V = 856.4 (3) Å3
Triclinic, P1Z = 1
a = 8.0113 (14) ÅMo Kα radiation
b = 8.3126 (14) ŵ = 0.86 mm1
c = 14.215 (3) ÅT = 291 K
α = 99.374 (3)°0.26 × 0.20 × 0.18 mm
β = 102.689 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer
3294 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
2297 reflections with I > 2σ(I)
Tmin = 0.808, Tmax = 0.861Rint = 0.031
4686 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0581 restraint
wR(F2) = 0.127H-atom parameters constrained
S = 1.03Δρmax = 0.82 e Å3
3294 reflectionsΔρmin = 0.47 e Å3
234 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
xyzUiso*/Ueq
C10.2672 (5)0.8169 (5)0.4734 (3)0.0436 (8)
H10.28710.87530.42420.052*
C20.3614 (5)0.7036 (5)0.4944 (3)0.0464 (9)
H20.44790.69200.46200.056*
C30.3255 (6)0.6094 (5)0.5632 (3)0.0517 (10)
H30.38000.52690.57410.062*
C40.2066 (5)0.6394 (5)0.6158 (3)0.0439 (8)
H40.18490.58290.66550.053*
C50.1218 (4)0.7550 (4)0.5924 (2)0.0346 (7)
C60.0067 (5)0.8021 (4)0.6396 (2)0.0331 (7)
C70.1790 (6)0.8482 (5)0.7319 (3)0.0514 (9)
C80.2685 (6)0.8364 (6)0.8112 (3)0.0594 (11)
H8A0.17710.84510.87110.071*
H8B0.35780.72060.79380.071*
C90.3609 (7)0.9592 (7)0.8374 (4)0.0722 (14)
H9A0.31161.01530.90700.108*
H9B0.48890.89750.82320.108*
H9C0.34251.04480.79930.108*
C100.0172 (5)0.6772 (5)0.7884 (2)0.0405 (7)
C110.1746 (6)0.7618 (6)0.8615 (3)0.0551 (10)
H110.23710.87830.86740.066*
C120.2433 (6)0.6748 (6)0.9279 (3)0.0574 (11)
H120.34850.73460.98000.069*
C130.1561 (6)0.5013 (5)0.9166 (3)0.0473 (9)
C140.0003 (6)0.4204 (6)0.8422 (3)0.0560 (10)
H140.05820.30250.83420.067*
C150.0762 (6)0.5021 (5)0.7780 (3)0.0563 (11)
H150.18620.44310.72930.068*
C160.2347 (6)0.4050 (6)0.9865 (4)0.0607 (11)
H16A0.31070.35350.95810.091*
H16B0.13730.31580.99650.091*
H16C0.30570.48481.04920.091*
Cl10.35945 (13)0.75087 (13)0.28048 (7)0.0529 (3)
Cu10.00001.00000.50000.03407 (19)
N10.1517 (4)0.8428 (4)0.5214 (2)0.0366 (6)
N20.0939 (4)0.8995 (4)0.6031 (2)0.0387 (6)
N30.2055 (5)0.9288 (5)0.6598 (2)0.0503 (8)
N40.0578 (4)0.7672 (4)0.7204 (2)0.0428 (7)
O110.4876 (4)0.8173 (4)0.3132 (2)0.0591 (8)
O120.2782 (4)0.8561 (4)0.2241 (2)0.0564 (7)
O130.2264 (4)0.7560 (4)0.3667 (2)0.0594 (8)
O140.4462 (4)0.5766 (4)0.2267 (2)0.0740 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.058 (2)0.050 (2)0.0445 (19)0.0306 (18)0.0273 (18)0.0285 (17)
C20.055 (2)0.057 (2)0.050 (2)0.0327 (19)0.0264 (17)0.0321 (18)
C30.066 (3)0.060 (2)0.060 (2)0.046 (2)0.029 (2)0.036 (2)
C40.0469 (19)0.047 (2)0.055 (2)0.0257 (17)0.0234 (17)0.0300 (18)
C50.0441 (17)0.0351 (17)0.0335 (15)0.0162 (15)0.0167 (14)0.0193 (14)
C60.0402 (15)0.0269 (15)0.0345 (16)0.0145 (13)0.0089 (13)0.0101 (12)
C70.066 (2)0.054 (2)0.061 (2)0.034 (2)0.037 (2)0.0349 (19)
C80.060 (2)0.073 (3)0.049 (2)0.017 (2)0.026 (2)0.024 (2)
C90.075 (3)0.074 (3)0.069 (3)0.021 (3)0.033 (3)0.015 (3)
C100.0628 (18)0.0398 (18)0.0293 (14)0.0239 (16)0.0186 (12)0.0169 (13)
C110.059 (2)0.050 (2)0.056 (2)0.0147 (18)0.0140 (14)0.0198 (18)
C120.058 (2)0.067 (3)0.052 (2)0.026 (2)0.0083 (19)0.029 (2)
C130.060 (2)0.055 (2)0.0360 (18)0.0219 (19)0.0214 (17)0.0206 (17)
C140.066 (2)0.051 (2)0.057 (2)0.024 (2)0.012 (2)0.028 (2)
C150.066 (2)0.041 (2)0.056 (2)0.0145 (19)0.0016 (19)0.0248 (19)
C160.068 (3)0.058 (3)0.071 (3)0.032 (2)0.024 (2)0.031 (2)
Cl10.0524 (5)0.0504 (6)0.0511 (5)0.0100 (4)0.0129 (4)0.0157 (4)
Cu10.0445 (3)0.0388 (3)0.0348 (3)0.0229 (3)0.0183 (2)0.0261 (3)
N10.0407 (15)0.0344 (14)0.0394 (15)0.0156 (13)0.0090 (12)0.0198 (12)
N20.0468 (15)0.0495 (18)0.0299 (13)0.0191 (13)0.0173 (12)0.0234 (12)
N30.065 (2)0.066 (2)0.0453 (18)0.0412 (18)0.0238 (16)0.0341 (16)
N40.0607 (18)0.0420 (16)0.0392 (15)0.0266 (14)0.0190 (14)0.0224 (13)
O110.0631 (17)0.0517 (17)0.0564 (17)0.0120 (14)0.0141 (14)0.0147 (14)
O120.0551 (15)0.0517 (17)0.0565 (16)0.0090 (13)0.0131 (13)0.0177 (14)
O130.0586 (16)0.0471 (16)0.0525 (18)0.0096 (13)0.0075 (14)0.0152 (14)
O140.068 (2)0.0549 (19)0.066 (2)0.0070 (16)0.0069 (17)0.0063 (16)
Geometric parameters (Å, º) top
C1—N11.310 (5)C10—N41.449 (4)
C1—C21.398 (5)C11—C121.395 (5)
C1—H10.930C11—H110.930
C2—C31.376 (5)C12—C131.371 (6)
C2—H20.930C12—H120.930
C3—C41.387 (5)C13—C141.351 (6)
C3—H30.930C13—C161.518 (5)
C4—C51.372 (4)C14—C151.367 (5)
C4—H40.930C14—H140.930
C5—N11.361 (4)C15—H150.930
C5—C61.456 (4)C16—H16A0.960
C6—N21.312 (4)C16—H16B0.960
C6—N41.348 (4)C16—H16C0.960
C7—N31.325 (4)Cl1—O121.398 (3)
C7—N41.356 (5)Cl1—O141.407 (3)
C7—C81.464 (5)Cl1—O131.422 (3)
C8—C91.474 (6)Cl1—O111.426 (3)
C8—H8A0.970Cl1—Cu13.5736 (11)
C8—H8B0.970Cu1—N21.982 (3)
C9—H9A0.960Cu1—N2i1.982 (3)
C9—H9B0.960Cu1—N1i2.043 (3)
C9—H9C0.960Cu1—N12.043 (3)
C10—C111.353 (6)N2—N31.374 (4)
C10—C151.394 (5)
N1—C1—C2121.6 (3)C14—C13—C16121.7 (4)
N1—C1—H1119.2C12—C13—C16120.1 (4)
C2—C1—H1119.2C13—C14—C15123.7 (4)
C3—C2—C1119.6 (3)C13—C14—H14118.1
C3—C2—H2120.2C15—C14—H14118.1
C1—C2—H2120.2C14—C15—C10117.4 (4)
C2—C3—C4118.8 (3)C14—C15—H15121.3
C2—C3—H3120.6C10—C15—H15121.3
C4—C3—H3120.6C13—C16—H16A109.5
C5—C4—C3118.0 (3)C13—C16—H16B109.5
C5—C4—H4121.0H16A—C16—H16B109.5
C3—C4—H4121.0C13—C16—H16C109.5
N1—C5—C4123.0 (3)H16A—C16—H16C109.5
N1—C5—C6111.5 (3)H16B—C16—H16C109.5
C4—C5—C6125.5 (3)O12—Cl1—O14112.3 (2)
N2—C6—N4108.3 (3)O12—Cl1—O13110.27 (18)
N2—C6—C5119.5 (3)O14—Cl1—O13108.0 (2)
N4—C6—C5132.2 (3)O12—Cl1—O11108.75 (19)
N3—C7—N4109.7 (3)O14—Cl1—O11110.0 (2)
N3—C7—C8127.6 (4)O13—Cl1—O11107.42 (19)
N4—C7—C8122.7 (3)O12—Cl1—Cu190.71 (12)
C7—C8—C9120.8 (4)O14—Cl1—Cu1138.86 (16)
C7—C8—H8A107.1O11—Cl1—Cu192.63 (13)
C9—C8—H8A107.1N2—Cu1—N2i180
C7—C8—H8B107.1N2—Cu1—N1i99.18 (12)
C9—C8—H8B107.1N2i—Cu1—N1i80.82 (12)
H8A—C8—H8B106.8N2—Cu1—N180.82 (12)
C8—C9—H9A109.5N2i—Cu1—N199.18 (12)
C8—C9—H9B109.5N1i—Cu1—N1180
H9A—C9—H9B109.5N2—Cu1—Cl1101.05 (9)
C8—C9—H9C109.5N2i—Cu1—Cl178.95 (9)
H9A—C9—H9C109.5N1i—Cu1—Cl176.99 (8)
H9B—C9—H9C109.5N1—Cu1—Cl1103.01 (8)
C11—C10—C15120.4 (4)C1—N1—C5118.7 (3)
C11—C10—N4120.6 (3)C1—N1—Cu1127.2 (2)
C15—C10—N4119.0 (3)C5—N1—Cu1114.1 (2)
C10—C11—C12120.1 (4)C6—N2—N3109.5 (3)
C10—C11—H11120.0C6—N2—Cu1113.3 (2)
C12—C11—H11120.0N3—N2—Cu1136.0 (2)
C13—C12—C11120.1 (4)C7—N3—N2105.7 (3)
C13—C12—H12120.0C6—N4—C7106.8 (3)
C11—C12—H12120.0C6—N4—C10126.5 (3)
C14—C13—C12118.2 (4)C7—N4—C10126.3 (3)
Symmetry code: (i) x, y+2, z+1.

Experimental details

Crystal data
Chemical formula[Cu(C16H16N4)2](ClO4)2
Mr791.10
Crystal system, space groupTriclinic, P1
Temperature (K)291
a, b, c (Å)8.0113 (14), 8.3126 (14), 14.215 (3)
α, β, γ (°)99.374 (3), 102.689 (3), 107.041 (2)
V3)856.4 (3)
Z1
Radiation typeMo Kα
µ (mm1)0.86
Crystal size (mm)0.26 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.808, 0.861
No. of measured, independent and
observed [I > 2σ(I)] reflections
4686, 3294, 2297
Rint0.031
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.127, 1.03
No. of reflections3294
No. of parameters234
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.82, 0.47

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Bruker, 2000).

Selected geometric parameters (Å, º) top
Cu1—N21.982 (3)Cu1—N12.043 (3)
N2—Cu1—N180.82 (12)
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds