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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
CCDC reference: 277743
Key indicators
- Single-crystal X-ray study
- T = 105 K
- Mean (C-C)= 0.003 Å
- R factor = 0.026
- wR factor = 0.062
- Data-to-parameter ratio = 25.6
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
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
C28H26N2Te2 | Z = 1 |
Mr = 645.71 | F(000) = 312 |
Triclinic, P1 | Dx = 1.735 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.8988 (10) Å | Cell parameters from 3604 reflections |
b = 7.935 (2) Å | θ = 2.5–30.5° |
c = 13.903 (4) Å | µ = 2.38 mm−1 |
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 tube | 3378 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω scans with κ offsets | θmax = 30.5°, θmin = 2.7° |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | h = −8→8 |
Tmin = 0.669, Tmax = 0.890 | k = −11→11 |
18111 measured reflections | l = −19→19 |
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)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.062 | H-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 parameters | Δρmax = 1.19 e Å−3 |
0 restraints | Δρmin = −0.90 e Å−3 |
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 | Uiso*/Ueq | |
Te1 | 0.15494 (2) | 0.690710 (18) | 0.332048 (10) | 0.01958 (5) | |
N1 | 0.0408 (3) | 0.4388 (2) | 0.51072 (13) | 0.0169 (3) | |
C1 | 0.2041 (4) | 0.3941 (3) | 0.44676 (15) | 0.0172 (4) | |
C2 | 0.2843 (4) | 0.4833 (3) | 0.36719 (15) | 0.0165 (4) | |
C3 | 0.4564 (4) | 0.4296 (3) | 0.31316 (16) | 0.0196 (4) | |
H3 | 0.5150 | 0.4879 | 0.2597 | 0.023* | |
C4 | 0.5421 (4) | 0.2938 (3) | 0.33619 (16) | 0.0204 (4) | |
H4 | 0.6598 | 0.2610 | 0.2988 | 0.024* | |
C5 | 0.4588 (4) | 0.2044 (3) | 0.41332 (17) | 0.0209 (4) | |
H5 | 0.5167 | 0.1097 | 0.4280 | 0.025* | |
C6 | 0.2900 (4) | 0.2554 (3) | 0.46836 (16) | 0.0200 (4) | |
H6 | 0.2322 | 0.1954 | 0.5213 | 0.024* | |
C7 | 0.3881 (4) | 0.7528 (3) | 0.21795 (16) | 0.0199 (4) | |
C8 | 0.3066 (4) | 0.6937 (3) | 0.12062 (17) | 0.0235 (5) | |
H8 | 0.1511 | 0.6169 | 0.1052 | 0.028* | |
C9 | 0.4514 (4) | 0.7463 (3) | 0.04563 (17) | 0.0248 (5) | |
C10 | 0.6786 (4) | 0.8606 (3) | 0.07043 (17) | 0.0248 (5) | |
H10 | 0.7782 | 0.8971 | 0.0200 | 0.030* | |
C11 | 0.7636 (4) | 0.9229 (3) | 0.16720 (17) | 0.0215 (4) | |
C12 | 0.6157 (4) | 0.8662 (3) | 0.24001 (16) | 0.0199 (4) | |
H12 | 0.6712 | 0.9059 | 0.3062 | 0.024* | |
C13 | 0.3633 (6) | 0.6804 (4) | −0.05938 (19) | 0.0373 (6) | |
H13A | 0.4595 | 0.7587 | −0.1010 | 0.056* | |
H13B | 0.1978 | 0.6802 | −0.0680 | 0.056* | |
H13C | 0.3754 | 0.5597 | −0.0773 | 0.056* | |
C14 | 1.0064 (4) | 1.0518 (3) | 0.19236 (19) | 0.0273 (5) | |
H14A | 1.1244 | 1.0045 | 0.1586 | 0.041* | |
H14B | 1.0429 | 1.0687 | 0.2628 | 0.041* | |
H14C | 1.0094 | 1.1659 | 0.1720 | 0.041* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Te1 | 0.01857 (8) | 0.02146 (8) | 0.02050 (8) | 0.00583 (6) | 0.00625 (5) | 0.00813 (5) |
N1 | 0.0146 (8) | 0.0170 (8) | 0.0171 (8) | 0.0006 (6) | 0.0033 (6) | 0.0035 (6) |
C1 | 0.0146 (9) | 0.0176 (9) | 0.0165 (10) | 0.0006 (8) | 0.0014 (7) | 0.0009 (7) |
C2 | 0.0151 (9) | 0.0162 (9) | 0.0157 (9) | 0.0007 (7) | 0.0010 (7) | 0.0024 (7) |
C3 | 0.0184 (10) | 0.0205 (10) | 0.0172 (10) | 0.0014 (8) | 0.0042 (8) | 0.0020 (8) |
C4 | 0.0190 (10) | 0.0193 (10) | 0.0207 (10) | 0.0037 (8) | 0.0033 (8) | −0.0010 (8) |
C5 | 0.0214 (10) | 0.0175 (10) | 0.0223 (11) | 0.0038 (8) | 0.0013 (8) | 0.0011 (8) |
C6 | 0.0214 (10) | 0.0191 (10) | 0.0184 (10) | 0.0035 (8) | 0.0019 (8) | 0.0036 (8) |
C7 | 0.0214 (10) | 0.0215 (10) | 0.0187 (10) | 0.0068 (8) | 0.0059 (8) | 0.0074 (8) |
C8 | 0.0235 (11) | 0.0220 (11) | 0.0223 (11) | 0.0015 (9) | 0.0012 (8) | 0.0052 (8) |
C9 | 0.0329 (12) | 0.0213 (11) | 0.0182 (11) | 0.0046 (10) | 0.0009 (9) | 0.0028 (8) |
C10 | 0.0281 (12) | 0.0262 (11) | 0.0196 (11) | 0.0046 (10) | 0.0088 (9) | 0.0069 (9) |
C11 | 0.0212 (10) | 0.0208 (10) | 0.0229 (11) | 0.0050 (9) | 0.0057 (8) | 0.0064 (8) |
C12 | 0.0229 (10) | 0.0206 (10) | 0.0172 (10) | 0.0068 (8) | 0.0024 (8) | 0.0051 (8) |
C13 | 0.0485 (17) | 0.0364 (14) | 0.0200 (12) | 0.0009 (13) | 0.0007 (11) | 0.0035 (10) |
C14 | 0.0202 (11) | 0.0284 (12) | 0.0314 (13) | 0.0018 (10) | 0.0044 (9) | 0.0082 (10) |
Geometric parameters (Å, º) top
Te1—C2 | 2.104 (2) | C7—C8 | 1.397 (3) |
Te1—C7 | 2.144 (2) | C8—C9 | 1.399 (3) |
Te1—N1i | 2.6916 (19) | C8—H8 | 0.9500 |
N1—N1i | 1.263 (4) | C9—C10 | 1.397 (4) |
N1—C1 | 1.412 (3) | C9—C13 | 1.509 (3) |
C1—C6 | 1.396 (3) | C10—C11 | 1.398 (3) |
C1—C2 | 1.414 (3) | C10—H10 | 0.9500 |
C2—C3 | 1.403 (3) | C11—C12 | 1.393 (3) |
C3—C4 | 1.381 (3) | C11—C14 | 1.511 (3) |
C3—H3 | 0.9500 | C12—H12 | 0.9500 |
C4—C5 | 1.391 (3) | C13—H13A | 0.9800 |
C4—H4 | 0.9500 | C13—H13B | 0.9800 |
C5—C6 | 1.386 (3) | C13—H13C | 0.9800 |
C5—H5 | 0.9500 | C14—H14A | 0.9800 |
C6—H6 | 0.9500 | C14—H14B | 0.9800 |
C7—C12 | 1.392 (3) | C14—H14C | 0.9800 |
| | | |
C2—Te1—C7 | 94.87 (8) | C7—C8—H8 | 119.6 |
C2—Te1—N1i | 68.31 (7) | C9—C8—H8 | 119.6 |
C7—Te1—N1i | 162.41 (7) | C10—C9—C8 | 118.4 (2) |
N1i—N1—C1 | 114.9 (2) | C10—C9—C13 | 121.1 (2) |
C6—C1—N1 | 115.29 (19) | C8—C9—C13 | 120.5 (2) |
C6—C1—C2 | 120.7 (2) | C9—C10—C11 | 122.0 (2) |
N1—C1—C2 | 123.98 (19) | C9—C10—H10 | 119.0 |
C3—C2—C1 | 117.4 (2) | C11—C10—H10 | 119.0 |
C3—C2—Te1 | 121.12 (15) | C12—C11—C10 | 118.1 (2) |
C1—C2—Te1 | 121.49 (15) | C12—C11—C14 | 120.8 (2) |
C4—C3—C2 | 121.3 (2) | C10—C11—C14 | 121.1 (2) |
C4—C3—H3 | 119.4 | C7—C12—C11 | 121.5 (2) |
C2—C3—H3 | 119.4 | C7—C12—H12 | 119.3 |
C3—C4—C5 | 121.0 (2) | C11—C12—H12 | 119.3 |
C3—C4—H4 | 119.5 | C9—C13—H13A | 109.5 |
C5—C4—H4 | 119.5 | C9—C13—H13B | 109.5 |
C6—C5—C4 | 119.0 (2) | H13A—C13—H13B | 109.5 |
C6—C5—H5 | 120.5 | C9—C13—H13C | 109.5 |
C4—C5—H5 | 120.5 | H13A—C13—H13C | 109.5 |
C5—C6—C1 | 120.7 (2) | H13B—C13—H13C | 109.5 |
C5—C6—H6 | 119.7 | C11—C14—H14A | 109.5 |
C1—C6—H6 | 119.7 | C11—C14—H14B | 109.5 |
C12—C7—C8 | 119.3 (2) | H14A—C14—H14B | 109.5 |
C12—C7—Te1 | 119.98 (16) | C11—C14—H14C | 109.5 |
C8—C7—Te1 | 120.44 (17) | H14A—C14—H14C | 109.5 |
C7—C8—C9 | 120.7 (2) | H14B—C14—H14C | 109.5 |
| | | |
N1i—N1—C1—C6 | −178.3 (2) | C2—Te1—C7—C12 | −84.88 (19) |
N1i—N1—C1—C2 | 3.4 (3) | N1i—Te1—C7—C12 | −68.3 (3) |
C6—C1—C2—C3 | −1.6 (3) | C2—Te1—C7—C8 | 101.12 (19) |
N1—C1—C2—C3 | 176.72 (19) | N1i—Te1—C7—C8 | 117.7 (3) |
C6—C1—C2—Te1 | 179.30 (15) | C12—C7—C8—C9 | 0.4 (4) |
N1—C1—C2—Te1 | −2.4 (3) | Te1—C7—C8—C9 | 174.44 (18) |
C7—Te1—C2—C3 | −3.80 (18) | C7—C8—C9—C10 | −0.6 (4) |
N1i—Te1—C2—C3 | −178.47 (19) | C7—C8—C9—C13 | 179.3 (2) |
C7—Te1—C2—C1 | 175.31 (17) | C8—C9—C10—C11 | 0.0 (4) |
N1i—Te1—C2—C1 | 0.64 (15) | C13—C9—C10—C11 | −179.9 (2) |
C1—C2—C3—C4 | 0.7 (3) | C9—C10—C11—C12 | 0.7 (4) |
Te1—C2—C3—C4 | 179.82 (16) | C9—C10—C11—C14 | −177.7 (2) |
C2—C3—C4—C5 | 0.6 (3) | C8—C7—C12—C11 | 0.3 (3) |
C3—C4—C5—C6 | −1.1 (3) | Te1—C7—C12—C11 | −173.74 (17) |
C4—C5—C6—C1 | 0.2 (3) | C10—C11—C12—C7 | −0.9 (3) |
N1—C1—C6—C5 | −177.27 (19) | C14—C11—C12—C7 | 177.5 (2) |
C2—C1—C6—C5 | 1.1 (3) | | |
Symmetry code: (i) −x, −y+1, −z+1. |
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