Di­bromo­di­phenyl­tellurium(IV)

organic papers

Acta Cryst.(2004). E60, o2511±o2512 doi:10.1107/S1600536804028284 Jens Beckmannet al. C₁₂H₁₀Br₂Te

o2511

Structure Reports Online

ISSN 1600-5368

Dibromodiphenyltellurium(IV)

Jens Beckmann,*³ Dainis Dakternieks, Andrew Duthie and Cassandra Mitchell

Centre for Chiral and Molecular Technologies, Deakin University, Geelong 3217, Victoria, Australia

³ Present address: Institut fuÈr Chemie, Freie UniversitaÈt Berlin, Fabeckstrasse 34-36, 14195 Berlin, Germany

Correspondence e-mail: beckmann@chemie.fu-berlin.de

Key indicators

Single-crystal X-ray study

T= 295 K

Mean(C±C) = 0.008 AÊ

Rfactor = 0.029

wRfactor = 0.070

Data-to-parameter ratio = 20.6

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved

The previously described structure of diphenyltellurium dibromide, C12H10Br2Te, has been reinvestigated. The mole-cule lies on a twofold rotation axis.

Comment

The supramolecular structures of diorganotellurium dihalides,

R2TeX2 (R = alkyl, aryl;X= F, Cl, Br, I), which have been analysed using the concepts of crystal engineering, have attracted great attention in recent years due to their diverse modes of secondary interactions (Zukerman-Schpector & Haiduc, 2001). We have now reinvestigated the structure of diphenyltellurium dibromide, ®rst described without inclusion of H atoms (Christofferson & McCullough, 1958) for comparison with similar compounds prepared by our group (Beckmann et al., 2004). The molecule lies on a twofold rotation axis. Unlike the recently investigated (Me2NC6H4)2-TeBr2 (Beckmann et al., 2004), which shows secondary Br Br, but no Te Br interactions, Ph2TeBr2 reveals two secondary Te Br interactions (Fig. 1).

Experimental

The title compound was prepared according to the original literature procedure (Krafft & Lyons, 1894)

Crystal data

C12H10Br2Te

Mr= 441.62

Tetragonal,I41

a= 11.4345 (7) AÊ

c= 9.8068 (12) AÊ

V= 1282.22 (19) AÊ3

Z= 4

Dx= 2.288 Mg mÿ3

MoKradiation Cell parameters from 2187

re¯ections

= 2.5±27.4

= 8.52 mmÿ1

T= 295 (2) K Block, yellow 0.400.350.35 mm

Data collection

Bruker SMART CCD area-detector diffractometer

'and!scans

Absorption correction: multi-scan (SADABS; Bruker, 2000)

Tmin= 0.043,Tmax= 0.050

3889 measured re¯ections

1419 independent re¯ections 1323 re¯ections withI> 2(I)

Rint= 0.027

max= 27.4

h=ÿ14!8

k=ÿ14!14

l=ÿ12!12

Refinement

Re®nement onF2

R[F2_{> 2(F}2_{)] = 0.029}

wR(F2_{) = 0.070}

S= 1.06 1419 re¯ections 69 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0337P)2]

whereP= (Fo2+ 2Fc2)/3

(/)max< 0.001 max= 0.74 e AÊÿ3 min=ÿ0.31 e AÊÿ3

Absolute structure: Flack (1983) Flack parameter = 0.069 (16)

Table 1

Selected geometric parameters (AÊ,_).

TeÐBr 2.6818 (6) TeÐC1 2.133 (5) BrÐTeÐBri _{177.31 (3)}

C1ÐTeÐBr 90.42 (12) C1

i_{ÐTeÐBr 91.36 (12)}

C1i_{ÐTeÐC1 96.9 (3)}

Symmetry code: (i)ÿx;1ÿy;z.

The H atoms were placed in geometrically calculated positions and re®ned using a riding model (CÐH = 0.93 AÊ). The isotropic displa-cement parameters were constrained at 1.2Ueq(C).

Data collection:SMART(Bruker, 2000); cell re®nement:SAINT

(Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics:

DIAMOND (Bergerhoff et al., 1996); software used to prepare material for publication:SHELXL97.

Dr Jonathan White (The University of Melbourne) is gratefully acknowledged for the X-ray data collection.

References

Beckmann, J., Dakternieks, D., Duthie, A., Mitchell, C. & SchuÈrmann, M. (2004).Aust. J. Chem.Submitted.

Bergerhoff, G., Berndt, M. & Brandenburg, K. (1996).J. Res. Natl Inst. Stand. Technol.101, 221±225.

Bruker (2000).SMART,SAINTandSADABS.Bruker AXS Inc., Madison, Wisconsin USA.

Christofferson, G. D. & McCullough, J. D. (1958).Acta Cryst.11, 249±256. Flack, H. D. (1983).Acta Cryst.A39, 876±881.

Krafft, F. & Lyons, R. E. (1894).Ber. Dtsch Chem. Ges.27, 1768.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.

Zukerman-Schpector, J. & Haiduc, I. (2001).Phosphorous Sulfur Silicon,171± 172, 73±112.

Figure 1

View of (I), showing the labelling of non-H atoms. Displacement ellipsoids are shown at 30% probability levels. [Symmetry codes: (i)ÿx, 1ÿy, z; (ii)1

supporting information

sup-1 Acta Cryst. (2004). E60, o2511–o2512

supporting information

Acta Cryst. (2004). E60, o2511–o2512 [https://doi.org/10.1107/S1600536804028284]

Dibromodiphenyltellurium(IV)

Jens Beckmann, Dainis Dakternieks, Andrew Duthie and Cassandra Mitchell

Dibromodiphenyltellurium

Crystal data C12H10Br2Te Mr = 441.62 Tetragonal, I41 Hall symbol: I 4bw a = 11.4345 (7) Å c = 9.8068 (12) Å V = 1282.22 (19) Å3 Z = 4

F(000) = 816

Dx = 2.288 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 2187 reflections θ = 2.5–27.4°

µ = 8.52 mm−1 T = 295 K Block, yellow

0.40 × 0.35 × 0.35 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

φ and ω scans

Absorption correction: multi-scan (SADABS; Bruker, 2000) Tmin = 0.043, Tmax = 0.050

3889 measured reflections 1419 independent reflections 1323 reflections with I > 2σ(I) Rint = 0.027

θmax = 27.4°, θmin = 2.5° h = −14→8

k = −14→14 l = −12→12

Refinement Refinement on F2 Least-squares matrix: full R[F2 _{> 2σ(F}2_{)] = 0.029} wR(F2_{) = 0.070} S = 1.06 1419 reflections 69 parameters 1 restraint

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained w = 1/[σ2_(F

o2) + (0.0337P)2] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max < 0.001

Δρmax = 0.74 e Å−3 Δρmin = −0.31 e Å−3

Absolute structure: Flack (1983) Absolute structure parameter: 0.069 (16)

Special details

Refinement. Refinement of F2 _{against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F}2_, conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

C1 −0.0041 (4) 0.3605 (4) 0.1772 (5) 0.0347 (10)

C2 −0.0883 (5) 0.2761 (4) 0.1666 (5) 0.0418 (12)

H2 −0.1455 0.2808 0.0994 0.050*

C3 −0.0870 (5) 0.1822 (4) 0.2591 (6) 0.0512 (13)

H3 −0.1433 0.1237 0.2530 0.061*

C4 −0.0043 (6) 0.1769 (4) 0.3563 (6) 0.0530 (15)

H4 −0.0045 0.1146 0.4171 0.064*

C5 0.0807 (6) 0.2617 (5) 0.3681 (6) 0.0511 (13)

H5 0.1376 0.2561 0.4355 0.061*

C6 0.0804 (4) 0.3546 (4) 0.2790 (6) 0.0420 (10)

H6 0.1364 0.4132 0.2868 0.050*

Br 0.23428 (5) 0.49056 (5) 0.02656 (6) 0.06433 (19)

Te 0.0000 0.5000 0.03297 (5) 0.03859 (13)

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

C1 0.036 (3) 0.029 (2) 0.039 (2) 0.0042 (18) 0.0033 (18) −0.0041 (17)

C2 0.040 (3) 0.039 (3) 0.046 (3) −0.001 (2) 0.001 (2) −0.006 (2)

C3 0.063 (3) 0.030 (2) 0.060 (4) −0.012 (2) 0.006 (3) −0.005 (2)

C4 0.074 (4) 0.030 (3) 0.055 (3) 0.003 (3) 0.002 (3) 0.010 (2)

C5 0.058 (4) 0.044 (3) 0.051 (3) 0.007 (3) −0.008 (3) 0.001 (2)

C6 0.042 (2) 0.032 (2) 0.052 (3) −0.0039 (18) −0.001 (3) −0.004 (2)

Br 0.0488 (3) 0.0730 (4) 0.0712 (4) 0.0032 (3) 0.0233 (3) −0.0011 (4)

Te 0.0419 (2) 0.0372 (2) 0.0366 (2) −0.00096 (17) 0.000 0.000

Geometric parameters (Å, º)

Te—Br 2.6818 (6) C4—C5 1.377 (8)

Te—C1 2.133 (5) C4—H4 0.9300

C1—C2 1.367 (7) C5—C6 1.376 (7)

C1—C6 1.391 (7) C5—H5 0.9300

C2—C3 1.406 (7) C6—H6 0.9300

C2—H2 0.9300 Te—C1i _{2.133 (5)}

C3—C4 1.344 (8) Te—Bri _{2.6818 (6)}

C3—H3 0.9300

Br—Te—Bri _{177.31 (3) C2—C3—H3 120.0}

C1—Te—Br 90.42 (12) C3—C4—C5 121.6 (5)

supporting information

sup-3 Acta Cryst. (2004). E60, o2511–o2512

C1i_{—Te—C1 96.9 (3) C5—C4—H4 119.2}

C2—C1—C6 120.7 (5) C6—C5—C4 119.3 (5)

C2—C1—Te 119.5 (4) C6—C5—H5 120.4

C6—C1—Te 119.8 (3) C4—C5—H5 120.4

C1—C2—C3 118.8 (5) C5—C6—C1 119.6 (4)

C1—C2—H2 120.6 C5—C6—H6 120.2

C3—C2—H2 120.6 C1—C6—H6 120.2

C4—C3—C2 119.9 (5) C1i_—Te—Bri _{90.42 (12)}

C4—C3—H3 120.0 C1—Te—Bri _{91.36 (12)}