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The title compound, C28H26N2Te2, prepared by reduction of (3,5-dimethyl­phen­yl)(2-nitro­phen­yl)tellurium(II), is the first structurally characterized example of an azo group bridging two TeII centers. The compound is centrosymmetric and the Te—N distance [2.6916 (19) Å] is longer than in non-bridging azo compounds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805018659/om6247sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805018659/om6247Isup2.hkl
Contains datablock I

CCDC reference: 277743

Key indicators

  • Single-crystal X-ray study
  • T = 105 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.026
  • wR factor = 0.062
  • Data-to-parameter ratio = 25.6

checkCIF/PLATON results

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Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(µ-Diazenediyldiphenyl-κ2C2,N2:κ2C2',N1)bis(3,5- dimethylphenyl)ditellurium(II) top
Crystal data top
C28H26N2Te2Z = 1
Mr = 645.71F(000) = 312
Triclinic, P1Dx = 1.735 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.8988 (10) ÅCell parameters from 3604 reflections
b = 7.935 (2) Åθ = 2.5–30.5°
c = 13.903 (4) ŵ = 2.38 mm1
α = 97.762 (10)°T = 105 K
β = 91.487 (10)°Lath fragment, red-orange
γ = 106.146 (15)°0.22 × 0.17 × 0.05 mm
V = 618.0 (3) Å3
Data collection top
Nonius KappaCCD (with Oxford Cryosystems Cryostream cooler)
diffractometer
3761 independent reflections
Radiation source: fine-focus sealed tube3378 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scans with κ offsetsθmax = 30.5°, θmin = 2.7°
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
h = 88
Tmin = 0.669, Tmax = 0.890k = 1111
18111 measured reflectionsl = 1919
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0299P)2 + 0.3859P]
where P = (Fo2 + 2Fc2)/3
3761 reflections(Δ/σ)max = 0.001
147 parametersΔρmax = 1.19 e Å3
0 restraintsΔρmin = 0.90 e Å3
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
Te10.15494 (2)0.690710 (18)0.332048 (10)0.01958 (5)
N10.0408 (3)0.4388 (2)0.51072 (13)0.0169 (3)
C10.2041 (4)0.3941 (3)0.44676 (15)0.0172 (4)
C20.2843 (4)0.4833 (3)0.36719 (15)0.0165 (4)
C30.4564 (4)0.4296 (3)0.31316 (16)0.0196 (4)
H30.51500.48790.25970.023*
C40.5421 (4)0.2938 (3)0.33619 (16)0.0204 (4)
H40.65980.26100.29880.024*
C50.4588 (4)0.2044 (3)0.41332 (17)0.0209 (4)
H50.51670.10970.42800.025*
C60.2900 (4)0.2554 (3)0.46836 (16)0.0200 (4)
H60.23220.19540.52130.024*
C70.3881 (4)0.7528 (3)0.21795 (16)0.0199 (4)
C80.3066 (4)0.6937 (3)0.12062 (17)0.0235 (5)
H80.15110.61690.10520.028*
C90.4514 (4)0.7463 (3)0.04563 (17)0.0248 (5)
C100.6786 (4)0.8606 (3)0.07043 (17)0.0248 (5)
H100.77820.89710.02000.030*
C110.7636 (4)0.9229 (3)0.16720 (17)0.0215 (4)
C120.6157 (4)0.8662 (3)0.24001 (16)0.0199 (4)
H120.67120.90590.30620.024*
C130.3633 (6)0.6804 (4)0.05938 (19)0.0373 (6)
H13A0.45950.75870.10100.056*
H13B0.19780.68020.06800.056*
H13C0.37540.55970.07730.056*
C141.0064 (4)1.0518 (3)0.19236 (19)0.0273 (5)
H14A1.12441.00450.15860.041*
H14B1.04291.06870.26280.041*
H14C1.00941.16590.17200.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Te10.01857 (8)0.02146 (8)0.02050 (8)0.00583 (6)0.00625 (5)0.00813 (5)
N10.0146 (8)0.0170 (8)0.0171 (8)0.0006 (6)0.0033 (6)0.0035 (6)
C10.0146 (9)0.0176 (9)0.0165 (10)0.0006 (8)0.0014 (7)0.0009 (7)
C20.0151 (9)0.0162 (9)0.0157 (9)0.0007 (7)0.0010 (7)0.0024 (7)
C30.0184 (10)0.0205 (10)0.0172 (10)0.0014 (8)0.0042 (8)0.0020 (8)
C40.0190 (10)0.0193 (10)0.0207 (10)0.0037 (8)0.0033 (8)0.0010 (8)
C50.0214 (10)0.0175 (10)0.0223 (11)0.0038 (8)0.0013 (8)0.0011 (8)
C60.0214 (10)0.0191 (10)0.0184 (10)0.0035 (8)0.0019 (8)0.0036 (8)
C70.0214 (10)0.0215 (10)0.0187 (10)0.0068 (8)0.0059 (8)0.0074 (8)
C80.0235 (11)0.0220 (11)0.0223 (11)0.0015 (9)0.0012 (8)0.0052 (8)
C90.0329 (12)0.0213 (11)0.0182 (11)0.0046 (10)0.0009 (9)0.0028 (8)
C100.0281 (12)0.0262 (11)0.0196 (11)0.0046 (10)0.0088 (9)0.0069 (9)
C110.0212 (10)0.0208 (10)0.0229 (11)0.0050 (9)0.0057 (8)0.0064 (8)
C120.0229 (10)0.0206 (10)0.0172 (10)0.0068 (8)0.0024 (8)0.0051 (8)
C130.0485 (17)0.0364 (14)0.0200 (12)0.0009 (13)0.0007 (11)0.0035 (10)
C140.0202 (11)0.0284 (12)0.0314 (13)0.0018 (10)0.0044 (9)0.0082 (10)
Geometric parameters (Å, º) top
Te1—C22.104 (2)C7—C81.397 (3)
Te1—C72.144 (2)C8—C91.399 (3)
Te1—N1i2.6916 (19)C8—H80.9500
N1—N1i1.263 (4)C9—C101.397 (4)
N1—C11.412 (3)C9—C131.509 (3)
C1—C61.396 (3)C10—C111.398 (3)
C1—C21.414 (3)C10—H100.9500
C2—C31.403 (3)C11—C121.393 (3)
C3—C41.381 (3)C11—C141.511 (3)
C3—H30.9500C12—H120.9500
C4—C51.391 (3)C13—H13A0.9800
C4—H40.9500C13—H13B0.9800
C5—C61.386 (3)C13—H13C0.9800
C5—H50.9500C14—H14A0.9800
C6—H60.9500C14—H14B0.9800
C7—C121.392 (3)C14—H14C0.9800
C2—Te1—C794.87 (8)C7—C8—H8119.6
C2—Te1—N1i68.31 (7)C9—C8—H8119.6
C7—Te1—N1i162.41 (7)C10—C9—C8118.4 (2)
N1i—N1—C1114.9 (2)C10—C9—C13121.1 (2)
C6—C1—N1115.29 (19)C8—C9—C13120.5 (2)
C6—C1—C2120.7 (2)C9—C10—C11122.0 (2)
N1—C1—C2123.98 (19)C9—C10—H10119.0
C3—C2—C1117.4 (2)C11—C10—H10119.0
C3—C2—Te1121.12 (15)C12—C11—C10118.1 (2)
C1—C2—Te1121.49 (15)C12—C11—C14120.8 (2)
C4—C3—C2121.3 (2)C10—C11—C14121.1 (2)
C4—C3—H3119.4C7—C12—C11121.5 (2)
C2—C3—H3119.4C7—C12—H12119.3
C3—C4—C5121.0 (2)C11—C12—H12119.3
C3—C4—H4119.5C9—C13—H13A109.5
C5—C4—H4119.5C9—C13—H13B109.5
C6—C5—C4119.0 (2)H13A—C13—H13B109.5
C6—C5—H5120.5C9—C13—H13C109.5
C4—C5—H5120.5H13A—C13—H13C109.5
C5—C6—C1120.7 (2)H13B—C13—H13C109.5
C5—C6—H6119.7C11—C14—H14A109.5
C1—C6—H6119.7C11—C14—H14B109.5
C12—C7—C8119.3 (2)H14A—C14—H14B109.5
C12—C7—Te1119.98 (16)C11—C14—H14C109.5
C8—C7—Te1120.44 (17)H14A—C14—H14C109.5
C7—C8—C9120.7 (2)H14B—C14—H14C109.5
N1i—N1—C1—C6178.3 (2)C2—Te1—C7—C1284.88 (19)
N1i—N1—C1—C23.4 (3)N1i—Te1—C7—C1268.3 (3)
C6—C1—C2—C31.6 (3)C2—Te1—C7—C8101.12 (19)
N1—C1—C2—C3176.72 (19)N1i—Te1—C7—C8117.7 (3)
C6—C1—C2—Te1179.30 (15)C12—C7—C8—C90.4 (4)
N1—C1—C2—Te12.4 (3)Te1—C7—C8—C9174.44 (18)
C7—Te1—C2—C33.80 (18)C7—C8—C9—C100.6 (4)
N1i—Te1—C2—C3178.47 (19)C7—C8—C9—C13179.3 (2)
C7—Te1—C2—C1175.31 (17)C8—C9—C10—C110.0 (4)
N1i—Te1—C2—C10.64 (15)C13—C9—C10—C11179.9 (2)
C1—C2—C3—C40.7 (3)C9—C10—C11—C120.7 (4)
Te1—C2—C3—C4179.82 (16)C9—C10—C11—C14177.7 (2)
C2—C3—C4—C50.6 (3)C8—C7—C12—C110.3 (3)
C3—C4—C5—C61.1 (3)Te1—C7—C12—C11173.74 (17)
C4—C5—C6—C10.2 (3)C10—C11—C12—C70.9 (3)
N1—C1—C6—C5177.27 (19)C14—C11—C12—C7177.5 (2)
C2—C1—C6—C51.1 (3)
Symmetry code: (i) x, y+1, z+1.
 

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