Bis(1-naphth­yl) telluride

Yellow crystals of the title compound, C₂₀H₁₄Te, were obtained serendipitously in an attempt to recrystallize the reduction product of (1-C₁₀H₇)[(CH(Me)COC₆H₅)]TeCl₂ from dichloro­methane. The mol­ecule exhibits an angular geometry with almost equal Te-C_ar­yl bonds and a C-Te-C angle close to values observed for other diaryl tellurides. One of the aromatic ring systems lies in the C-Te-C plane and the other is oriented at 76.81 (6)°, giving an almost T-shaped conformation that is compatible with the steric demand of 1-naphthyl ligands.

Key indicators

• Single-crystal X-ray study
• T = 130 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.028
• wR factor = 0.073
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT074_ALERT_1_C Occupancy Parameter = 0.0 for ..................        CG1
PLAT074_ALERT_1_C Occupancy Parameter = 0.0 for ..................        CG2
PLAT074_ALERT_1_C Occupancy Parameter = 0.0 for ..................        CG3
PLAT074_ALERT_1_C Occupancy Parameter = 0.0 for ..................        CG4
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.46
PLAT432_ALERT_2_C Short Inter X...Y Contact  Te     ..  C5      ..       3.50 Ang.

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Te          (*)       3.08

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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

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S1. Comment

The molecule of the title compound, (I) (Fig.1), adopts angular geometry similar to other symmetrical diaryltellurides, (4-XC₆H₅)₂Te, X = OMe (Farran et al., 1997); X = OH, NH₂, NMe₂ (Engman et al., 2002). Both Te—C_aryl bonds are 2.119 (2) Å and inclined at 96.32 (9)⁰. These bond parameters are quite close to the reported average values of 2.116 (20) Å (Allen, et al., 1987) and 96 (3)⁰ (Allen et al., 1993) which indicate little steric influence of 1-naphthyl ligands on the molecular geometry of (I). With sterically more demanding aryl ligands enlarged values for these bond parameters have been reported in the case of mesityl [2.140 (3) Å each, 101.0 (1)⁰ (Klapötke et al., 2005)], nonafluoromesityl [2.151 (5) Å each, 107.4 (2)⁰ (Voelker et al., 1999)] and supermesityl [2.156 (5) Å, 2.157 (5) Å, 107.3 (2)⁰ (Wieber et al., 1995)] analogues. However, the almost T-shaped conformation adopted by the molecule with an interplanar angle of 79.87 (4)⁰ between the planar [to within 0.005 (5) and 0.014 (7) Å] naphthalene rings may be attributed to steric repulsion between 1-naphthyl ligands.

The centroids of the four aromatic rings, defined as Cg1 (C1—C4, C9—C10), Cg2 (C5—C10), Cg3 (C11—C14, C19—C20) and Cg4 (C15—C20) are involved in the crystal packing of (I). Centrosymmetric pairs of molecules joined by reciprocal π(Cg1)···π(Cg2) interactions of 3.875 (1) Å (symmetry code: 1 – x, – y, 1 – z) are further connected via a Te···π(Cg2) = 3.9567 (2) Å (symmetry code: 1 – x, – y, 1 – z) contact and four C—H···π(ring centroid) interactions [C4—H4···π(Cg2) = 2.748 Å (symmetry code: 1/2 – x, 1/2 + y, z), C7—H7···π(Cg3) = 2.772 Å (symmetry code: 1 – x, 1 – y, 1 – z), C15—H15···π(Cg3) = 2.724 Å (symmetry code: 1 – x, -1/2 + y, 1/2 – z)) and C6—H6···π(Cg4) = 2.852 Å (symmetry code: 1 – x, 1 – y, 1 – z)] to form a three-dimensional network.

Bis(1-naphthyl)telluride, prepared earlier by the transfer of aryl ligands from (1-C₁₀H₇)₂Hg (Lyons et al., 1908) or (1-C₁₀H₇)₃Bi (Arnauld et al., 1999) to elemental tellurium has also been obtained by detelluration of (1-C₁₀H₇)₂Te₂ , analogous to that of dimesitylditelluride (Akiba et al., 1984). The angular geometry of (1-C₁₀H₇)₂Te is quite similar to bis(p-substituted phenyl)tellurides (Farran et al., 1997; Engman et al., 2002) and the aromatic rings are oriented to give rise to nearly T-shaped conformation, presumably due to steric repulsion of 1-naphthyl units. However, the steric influence of the 1-naphthyl ligand on the molecular geometry of the title compound is neglibible when compared with the mesityl (Klapötke et al., 2005), nonafluoromesityl (Voelker et al., 1999) or supermesityl (Wieber et al., 1995) analogues. The Te—C bond lengths and included angle compare well with the average values tabulated elsewhere (Allen, et al., 1987; Allen et al., 1993) and supramolecular associative η⁶-(1-C₁₀H₇)···Te interactions observed in the crystal packing of (1-C₁₀H₇)₂Te₂ (Schulz Lang, et al., 2002) are absent in the present case.

Related literature

Bis(1-naphthyl)telluride, prepared earlier by the transfer of aryl ligands from (1-C₁₀H₇)₂Hg (Lyons et al., 1908) or (1-C₁₀H₇)₃Bi (Arnauld et al., 1999) to elemental tellurium has also been obtained by detelluration of (1-C₁₀H₇)₂Te₂ , analogous to that of dimesitylditelluride (Akiba et al., 1984). The angular geometry of (1-C₁₀H₇)₂Te is quite similar to bis(p-substituted phenyl)tellurides (Farran et al., 1997; Engman et al., 2002) and the aromatic rings are oriented to give rise to nearly T-shaped conformation, presumably due to steric repulsion of 1-naphthyl units. However, the steric influence of the 1-naphthyl ligand on the molecular geometry of the title compound is neglibible when compared with the mesityl (Klapötke et al., 2005), nonafluoromesityl (Voelker et al., 1999) or supermesityl (Wieber et al., 1995) analogues. The Te—C bond lengths and included angle compare well with the average values tabulated elsewhere (Allen, et al., 1987; Allen et al., 1993) and supramolecular associative η⁶-(1-C₁₀H₇)···Te interactions observed in the crystal packing of (1-C₁₀H₇)₂Te₂ (Schulz Lang, et al., 2002) are absent in the present case.

S2. Experimental

Compound (I) was serendipitously obtained on recrystallization of the reduction product of (1-C₁₀H₇)[(CH(Me)COC₆H₅)]TeCl₂ from dichloromethane. Detelluration of the corresponding ditelluride, (1-C₁₀H₇)₂Te₂ with metallic copper, analogous to that of dimesitylditelluride (Akiba et al., 1984), also gave (I) in better yield.

S3. Refinement

The H atoms were placed in geometrically calculated positions using a riding model (C—H_arom. 0.95 Å) and the isotropic temperature factors constrained at 1.2 times U_eq of the carrier C atom. The maximum residual electron density of 1.048 e ų is near the Te atom.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenberg & Putz, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

	Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. The packing of (I) viewed along the b axis, showing pairs of molecules joined by reciprocal π···π interactions that are connected via C—H···π (ring centroid) interactions. H atoms not involved in the weak interactions have been omitted.

Bis(1-naphthyl) telluride

Crystal data

C20H14Te	F(000) = 1488
Mr = 381.91	Dx = 1.672 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6102 reflections
a = 14.0662 (6) Å	θ = 2.9–27.5°
b = 8.7390 (4) Å	µ = 1.95 mm^−1
c = 24.6881 (11) Å	T = 130 K
V = 3034.8 (2) Å^3	Block, yellow
Z = 8	0.45 × 0.40 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3477 independent reflections
Radiation source: sealed tube	3158 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→18
Tmin = 0.460, Tmax = 0.676	k = −11→5
11725 measured reflections	l = −28→32

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0396P)^2 + 2.317P] where P = (Fo^2 + 2Fc^2)/3
3477 reflections	(Δ/σ)max = 0.002
190 parameters	Δρmax = 1.05 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

Experimental. Characterization data for Compound (I) are: M.p. 108 ⁰C [lit. 108 - 109 ⁰C, Arnauld et al., 1999; 126.5 ⁰C, Lyons et al., 1908];d ¹³C (100.54 MHz, relative to Me₄Si in CDCl₃) 117.47, 126.29, 126.59, 126.96, 128.81, 129.19, 131.24, 133.76, 135.77, 137.97; d ¹²⁵Te (126.19 MHz, relative to Me₂Te, in CDCl₃) 466.5.

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.45233 (17)	0.0854 (3)	0.42238 (10)	0.0245 (5)
C2	0.40556 (19)	−0.0337 (3)	0.39838 (11)	0.0301 (5)
H2	0.4267	−0.0706	0.3642	0.036*
C3	0.32599 (19)	−0.1029 (3)	0.42369 (11)	0.0330 (6)
H3	0.2948	−0.1866	0.4068	0.040*
C4	0.29434 (18)	−0.0495 (3)	0.47212 (11)	0.0302 (5)
H4	0.2401	−0.0950	0.4885	0.036*
C5	0.31020 (18)	0.1264 (3)	0.54989 (10)	0.0299 (5)
H5	0.2561	0.0810	0.5664	0.036*
C6	0.35715 (19)	0.2418 (3)	0.57576 (10)	0.0320 (5)
H6	0.3361	0.2755	0.6103	0.038*
C7	0.4367 (2)	0.3111 (3)	0.55135 (11)	0.0320 (6)
H7	0.4691	0.3914	0.5696	0.038*
C8	0.46782 (18)	0.2640 (3)	0.50170 (10)	0.0280 (5)
H8	0.5210	0.3131	0.4856	0.034*
C9	0.34127 (17)	0.0736 (3)	0.49871 (10)	0.0252 (5)
C10	0.42193 (16)	0.1426 (3)	0.47375 (10)	0.0231 (5)
C11	0.50952 (17)	0.3739 (3)	0.35264 (9)	0.0226 (4)
C12	0.41523 (16)	0.4055 (3)	0.36146 (10)	0.0245 (5)
H12	0.3783	0.3376	0.3829	0.029*
C13	0.37230 (17)	0.5371 (3)	0.33913 (10)	0.0273 (5)
H13	0.3068	0.5567	0.3456	0.033*
C14	0.42384 (17)	0.6364 (3)	0.30837 (10)	0.0280 (5)
H14	0.3939	0.7239	0.2932	0.034*
C15	0.57735 (18)	0.7114 (3)	0.26683 (10)	0.0289 (5)
H15	0.5487	0.8003	0.2519	0.035*
C16	0.67125 (19)	0.6829 (3)	0.25723 (10)	0.0310 (6)
H16	0.7072	0.7512	0.2354	0.037*
C17	0.71505 (18)	0.5523 (3)	0.27965 (10)	0.0283 (5)
H17	0.7806	0.5334	0.2731	0.034*
C18	0.66396 (17)	0.4529 (3)	0.31069 (9)	0.0239 (5)
H18	0.6947	0.3658	0.3256	0.029*
C19	0.52199 (17)	0.6101 (3)	0.29884 (9)	0.0238 (5)
C20	0.56571 (16)	0.4768 (3)	0.32116 (9)	0.0222 (5)
Te	0.574114 (11)	0.171144 (18)	0.382005 (6)	0.02580 (8)
Cg1	0.3736	0.0192	0.4482	0.010*	0.00
Cg2	0.3892	0.1932	0.5252	0.010*	0.00
Cg3	0.4681	0.5066	0.3303	0.010*	0.00
Cg4	0.6192	0.5811	0.2891	0.010*	0.00

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0233 (11)	0.0249 (11)	0.0254 (12)	0.0004 (9)	0.0023 (9)	0.0034 (9)
C2	0.0315 (12)	0.0282 (13)	0.0306 (12)	0.0011 (10)	−0.0002 (11)	−0.0034 (10)
C3	0.0313 (13)	0.0277 (13)	0.0398 (14)	−0.0051 (11)	−0.0019 (11)	−0.0042 (11)
C4	0.0248 (12)	0.0273 (12)	0.0386 (14)	−0.0027 (10)	0.0026 (10)	0.0028 (10)
C5	0.0285 (12)	0.0325 (13)	0.0287 (12)	0.0051 (10)	0.0055 (10)	0.0064 (10)
C6	0.0350 (13)	0.0365 (14)	0.0246 (12)	0.0065 (11)	0.0016 (11)	−0.0007 (10)
C7	0.0382 (15)	0.0307 (13)	0.0272 (13)	0.0002 (10)	−0.0056 (11)	−0.0044 (10)
C8	0.0285 (12)	0.0270 (12)	0.0285 (12)	−0.0012 (10)	−0.0015 (10)	0.0015 (10)
C9	0.0241 (11)	0.0241 (11)	0.0274 (12)	0.0030 (9)	−0.0003 (9)	0.0076 (9)
C10	0.0236 (12)	0.0222 (11)	0.0235 (12)	0.0027 (9)	−0.0015 (9)	0.0054 (9)
C11	0.0271 (11)	0.0230 (10)	0.0176 (10)	−0.0014 (9)	−0.0020 (9)	−0.0007 (9)
C12	0.0237 (11)	0.0281 (12)	0.0218 (11)	−0.0006 (9)	0.0009 (9)	−0.0002 (9)
C13	0.0224 (11)	0.0336 (13)	0.0261 (12)	0.0040 (10)	−0.0027 (9)	−0.0029 (10)
C14	0.0312 (13)	0.0268 (12)	0.0261 (12)	0.0041 (10)	−0.0083 (10)	0.0001 (10)
C15	0.0352 (14)	0.0269 (12)	0.0247 (12)	−0.0007 (10)	−0.0068 (10)	0.0052 (10)
C16	0.0371 (15)	0.0288 (13)	0.0271 (12)	−0.0090 (10)	−0.0002 (11)	0.0065 (9)
C17	0.0254 (12)	0.0323 (13)	0.0273 (12)	−0.0029 (10)	0.0020 (10)	0.0000 (10)
C18	0.0255 (11)	0.0250 (11)	0.0213 (11)	0.0006 (9)	0.0004 (9)	0.0023 (9)
C19	0.0291 (12)	0.0234 (11)	0.0188 (10)	−0.0014 (10)	−0.0055 (9)	0.0002 (9)
C20	0.0254 (11)	0.0246 (11)	0.0168 (10)	−0.0006 (9)	−0.0026 (8)	−0.0029 (9)
Te	0.02321 (11)	0.02626 (11)	0.02792 (11)	0.00278 (6)	0.00458 (6)	0.00745 (6)

Geometric parameters (Å, º)

C1—C2	1.366 (4)	C11—C12	1.372 (3)
C1—C10	1.429 (3)	C11—C20	1.427 (3)
C1—Te	2.119 (2)	C11—Te	2.119 (2)
C2—C3	1.417 (4)	C12—C13	1.412 (3)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.359 (4)	C13—C14	1.362 (4)
C3—H3	0.9500	C13—H13	0.9500
C4—C9	1.423 (3)	C14—C19	1.419 (3)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.364 (4)	C15—C16	1.365 (4)
C5—C9	1.414 (3)	C15—C19	1.420 (3)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.408 (4)	C16—C17	1.410 (4)
C6—H6	0.9500	C16—H16	0.9500
C7—C8	1.365 (4)	C17—C18	1.363 (3)
C7—H7	0.9500	C17—H17	0.9500
C8—C10	1.421 (4)	C18—C20	1.421 (3)
C8—H8	0.9500	C18—H18	0.9500
C9—C10	1.425 (3)	C19—C20	1.428 (3)
Cg1···Cg2^i	3.8752 (1)	Cg3···H15^iii	2.7238
Cg2···Te^i	3.9567 (2)	Cg3···H7^iv	2.7721
Cg2···H4^ii	2.7485	Cg4···H6^iv	2.8525
C2—C1—C10	120.5 (2)	C12—C11—Te	121.88 (18)
C2—C1—Te	117.04 (19)	C20—C11—Te	118.41 (17)
C10—C1—Te	122.39 (17)	C11—C12—C13	121.0 (2)
C1—C2—C3	120.9 (2)	C11—C12—H12	119.5
C1—C2—H2	119.5	C13—C12—H12	119.5
C3—C2—H2	119.5	C14—C13—C12	120.6 (2)
C4—C3—C2	120.0 (2)	C14—C13—H13	119.7
C4—C3—H3	120.0	C12—C13—H13	119.7
C2—C3—H3	120.0	C13—C14—C19	120.5 (2)
C3—C4—C9	120.9 (2)	C13—C14—H14	119.8
C3—C4—H4	119.5	C19—C14—H14	119.8
C9—C4—H4	119.5	C16—C15—C19	120.9 (2)
C6—C5—C9	120.7 (2)	C16—C15—H15	119.5
C6—C5—H5	119.7	C19—C15—H15	119.5
C9—C5—H5	119.7	C15—C16—C17	120.2 (2)
C5—C6—C7	120.2 (2)	C15—C16—H16	119.9
C5—C6—H6	119.9	C17—C16—H16	119.9
C7—C6—H6	119.9	C18—C17—C16	120.4 (2)
C8—C7—C6	120.6 (2)	C18—C17—H17	119.8
C8—C7—H7	119.7	C16—C17—H17	119.8
C6—C7—H7	119.7	C17—C18—C20	121.4 (2)
C7—C8—C10	121.1 (2)	C17—C18—H18	119.3
C7—C8—H8	119.5	C20—C18—H18	119.3
C10—C8—H8	119.5	C14—C19—C15	121.7 (2)
C5—C9—C4	121.0 (2)	C14—C19—C20	119.2 (2)
C5—C9—C10	119.6 (2)	C15—C19—C20	119.2 (2)
C4—C9—C10	119.3 (2)	C18—C20—C11	123.0 (2)
C8—C10—C9	117.9 (2)	C18—C20—C19	118.0 (2)
C8—C10—C1	123.8 (2)	C11—C20—C19	119.1 (2)
C9—C10—C1	118.3 (2)	C1—Te—C11	96.32 (9)
C12—C11—C20	119.7 (2)	H15^iii—Cg3—H7^iv	154.7
C10—C1—C2—C3	0.1 (4)	C11—C12—C13—C14	−0.2 (4)
Te—C1—C2—C3	177.1 (2)	C12—C13—C14—C19	−0.8 (4)
C1—C2—C3—C4	1.0 (4)	C19—C15—C16—C17	−0.7 (4)
C2—C3—C4—C9	−1.4 (4)	C15—C16—C17—C18	0.5 (4)
C9—C5—C6—C7	0.7 (4)	C16—C17—C18—C20	0.3 (4)
C5—C6—C7—C8	0.0 (4)	C13—C14—C19—C15	179.8 (2)
C6—C7—C8—C10	−1.0 (4)	C13—C14—C19—C20	1.0 (4)
C6—C5—C9—C4	178.3 (2)	C16—C15—C19—C14	−178.8 (2)
C6—C5—C9—C10	−0.5 (4)	C16—C15—C19—C20	0.0 (4)
C3—C4—C9—C5	−178.1 (2)	C17—C18—C20—C11	178.8 (2)
C3—C4—C9—C10	0.7 (4)	C17—C18—C20—C19	−1.0 (3)
C7—C8—C10—C9	1.2 (4)	C12—C11—C20—C18	179.4 (2)
C7—C8—C10—C1	−178.4 (2)	Te—C11—C20—C18	−2.9 (3)
C5—C9—C10—C8	−0.4 (3)	C12—C11—C20—C19	−0.8 (3)
C4—C9—C10—C8	−179.2 (2)	Te—C11—C20—C19	176.93 (16)
C5—C9—C10—C1	179.2 (2)	C14—C19—C20—C18	179.6 (2)
C4—C9—C10—C1	0.4 (3)	C15—C19—C20—C18	0.8 (3)
C2—C1—C10—C8	178.8 (2)	C14—C19—C20—C11	−0.2 (3)
Te—C1—C10—C8	2.0 (3)	C15—C19—C20—C11	−179.0 (2)
C2—C1—C10—C9	−0.8 (3)	C2—C1—Te—C11	105.2 (2)
Te—C1—C10—C9	−177.60 (16)	C10—C1—Te—C11	−77.9 (2)
C20—C11—C12—C13	1.0 (4)	C12—C11—Te—C1	−2.4 (2)
Te—C11—C12—C13	−176.60 (18)	C20—C11—Te—C1	179.90 (17)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1/2, y+1/2, z; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, −y+1, −z+1.