Tri­phenyl­tellurium chloride

Ambika Chopra; Shalini Jain; Sanjay K Srivastava; Sushil K Gupta; Ray J Butcher

doi:10.1107/S160053681400498X

. 2014 Mar 12;70(Pt 4):o421–o422. doi: 10.1107/S160053681400498X

Triphenyltellurium chloride

Ambika Chopra ^a, Shalini Jain ^a, Sanjay K Srivastava ^a,^*, Sushil K Gupta ^a, Ray J Butcher ^b

PMCID: PMC3998628 PMID: 24826133

Abstract

The asymmetric unit of the title compound, C₁₈H₁₅ClTe, contains two molecules which are in inverted orientations. The compound displays a tetrahedral geometry around the Te atom in spite of there being five electron domains. This is attributed to the fact that the lone pair is not sterically active. The dihedral angles between the three phenyl rings are 76.51 (16)/73.75 (16)/71.06 (17) and 78.60 (17)/77.67 (16)/79.11 (16)° in the two molecules. The crystal packing features eight C—H⋯π interactions.

Related literature

For the first synthesis of the title compound, see: Günther et al. (1974 ▶). For related compounds, see: Klapötke et al. (2001 ▶); Naumann et al. (2002 ▶). For chalcogen-bearing compounds, see: Srivastava et al. (2010 ▶, 2011 ▶); Rastogi et al. (2011 ▶). For organotellurium(IV) derivatives that form metal complexes and supramolecular aggregations, see: Santos et al. (2007 ▶); Teikink & Zukerman-Schpector (2010 ▶). For their applications as antileishmanial and antibacterial agents, see: Lima et al. (2009 ▶); Soni et al. (2005 ▶).

Experimental

Crystal data

C₁₈H₁₅ClTe
M _r = 394.35
Monoclinic,
a = 18.7514 (3) Å
b = 9.60800 (15) Å
c = 18.4367 (3) Å
β = 105.2453 (16)°
V = 3204.74 (9) Å³
Z = 8
Cu Kα radiation
μ = 16.07 mm⁻¹
T = 123 K
0.25 × 0.12 × 0.08 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.215, T _max = 1.000
12435 measured reflections
6446 independent reflections
5854 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.077
S = 1.04
6446 reflections
361 parameters
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −1.24 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681400498X/jj2184sup1.cif

e-70-0o421-sup1.cif^{(455.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400498X/jj2184Isup2.hkl

e-70-0o421-Isup2.hkl^{(353.2KB, hkl)}

Click here for additional data file.^{(5.2KB, cml)}

Supporting information file. DOI: 10.1107/S160053681400498X/jj2184Isup3.cml

CCDC reference: 990042

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1, Cg2, Cg3, Cg4, Cg5 and Cg6 are the centroids of the C1A–C6A, C7A–C12A, C13A–C18A, C1B–C6B, C7B–C12B and C13B–C18B phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2A—H2AA⋯Cg2ⁱ	0.95	2.96	3.587 (4)	125
C5A—H5AA⋯Cg4	0.95	2.65	3.497 (4)	149
C10A—H10A⋯Cg1ⁱⁱ	0.95	2.83	3.580 (4)	137
C5B—H5BA⋯Cg5ⁱⁱⁱ	0.95	2.76	3.532 (4)	139
C11A—H11A⋯Cg3^iv	0.95	2.91	3.601 (4)	131
C12B—H12B⋯Cg6^v	0.95	2.95	3.671 (3)	134
C14B—H14B⋯Cg4^vi	0.95	2.86	3.589 (4)	134
C17B—H17B⋯Cg2	0.95	2.78	3.679 (4)	158

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

Acknowledgments

AC and SJ thank the JUG for the award of a University Fellowship. RJB acknowledges the NSF–MRI program (grant No. CHE0619278) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

1. Introduction

In recent years organotellurium compounds have been widely used as ligands forming complexes with supramolecular behaviour (Santos et al., 2007; Teikink et al., 2010; Srivastava et al., 2011). These compounds have interesting applications as antileishmanial and antibacterial agents (Lima et al., 2009; Soni et al., 2005). The crystal structures of related compounds, tris(pentafluorophenyl)tellurium chloride, (C₆H₅)₃TeCl and tris(pentafluorophenyl)tellurium bromide, (C₆H₅)₃TeBr have been reported earlier (Klapötke et al., 2001; Naumann et al., 2002). As part of our investigations on the chalcogen bearing compounds (Srivastava et al. 2010; Rastogi et al. 2011), we herein report the synthesis and X-ray crystal structure analysis of the title compound, triphenyltellurium chloride.

2. Experimental

2.1. Synthesis and crystallization

The title compound was prepared by the modified procedure described earlier (Günther et al.,1974). A mixture of TeCl₄ (26.8 g, 0.1 mol) and AlCl₃ (39.9 g, 0.3 mol) in 300 mL dry benzene was placed into a 500 mL two-necked, round-bottom flask equipped with a magnetic stirring bar, a nitrogen inlet and a reflux condenser. The reflux condenser was connected with Tygon tubing to a gas dispersion tube immersed in water containing phenolphthalein indicator. The reaction mixture was heated to reflux under nitrogen. Vigorous hydrogen chloride evolution occurred immediately. The hydrogen chloride was swept through the condenser into phenolphthalein solution by nitrogen and titrated with NaOH solution. The reaction mixture was poured into 400 mL of ice and water, when three equivalents of HCl had evolved. A dark colored solid was separated by filtration of the quenched reaction mixture and dissolved in minimum amount of boiling water. The hot mixture was then quickly filtered to give a clear colorless solution. On cooling the filtrate, a white crystalline solid of triphenyltellurium chloride separated out. The compound was crystallized in ethanol and chloroform mixture (60:40) to give white crystals suitable for X-ray analysis in 72% yield. M.P. 249-250 °C. Anal. calc. for C₁₈H₁₅ClTe(%): C,54.82; H,3.83; Cl,8.99; Te,32.35. Found: C,54.88; H,3.86; Cl,9.16; Te,32.30.

2.2. Refinement

H atoms were positioned geometrically and refined using the riding model, with C–H distance of 0.95 Å, with U_iso (H) = 1.20 U_eq (C) atoms.

3. Results and discussion

The molecular structure of the title compound, C18H15ClTe, is shown in Fig.1. The asymmetric unit of the structure contains two molecules which are in inverted orientations. The molecule displays a tetrahedral geometry around the Te atom (sum of bond angles, 436.56°) in spite of being five electron domains. This attributes the fact that the lone pair is not sterically active. This is in contrast with the reported structure of distorted octahedral geometry for (C₆F₅)₃TeCl (Klapotke et al., 2001) and trigonal bipyramidal geometry for (C₆F₅)₃TeBr (Naumann et al., 2002). This clearly indicates that there is no effect of free electron pair at Te in the present structure. The dihedral angles between the mean planes of the three phenyl rings C7A–C12A, C1A–C6A, C13A–C18A in molecule A and C7B–C12B, C1B–C6B, C13B–C18B in molecule B are 76.51 (16)/73.75 (16) and 78.60 (17)/77.67 (16)°, respectively, in the two molecules indicating that there is no conjugation between three aromatic rings. The two phenyl rings at C7 and C13 are inclined at an angle of 71.06 (17)° in molecule A and 79.11 (16)° in molecule B. The crystal packing is stabilized by eight C—H···π intermolecular interactions (Table 1, Fig.2).