Tris(dimethyl­phenyl­silyl)methane­tellurenyl iodide

The crystal structure of TpsiTeI [Tpsi = tris­(dimethyl­phenyl­silyl)meth­yl], C₂₅H₃₃ISi₃Te, exhibits discrete mol­ecules without Te...I, Te...Te or I...I inter­molecular contacts. TpsiTeI was prepared by cleavage of its parent ditellane with iodine, and represents a kinetically stabilized alkanetellurenyl iodide with a very bulky substituent. The mol­ecule possesses an angular C—Te—I arrangement [110.53 (7)°] with a Te—I single bond [2.7178 (7) Å].

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.031
• wR factor = 0.073
• Data-to-parameter ratio = 22.5

checkCIF/PLATON results

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Alert level C
PLAT322_ALERT_2_C Check Hybridisation of  Si1    in Main Residue .          ?

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

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

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Computing details

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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1996); software used to prepare material for publication: SHELXL97.

Tris(dimethylphenylsilyl)methanetellurenyl iodide

Crystal data

C25H33ISi3Te	F(000) = 1320
Mr = 672.28	Dx = 1.642 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6375 reflections
a = 16.076 (3) Å	θ = 3.1–27.5°
b = 17.248 (3) Å	µ = 2.37 mm^−1
c = 9.995 (2) Å	T = 200 K
β = 101.18 (3)°	Block, dark green
V = 2718.9 (9) Å^3	0.08 × 0.05 × 0.04 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	4995 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Vertically mounted graphite crystal monochromator	θmax = 27.5°, θmin = 3.2°
Detector resolution: 9 pixels mm^-1	h = −20→20
φ? ω? scans	k = −22→21
12153 measured reflections	l = −12→12
6229 independent reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0278P)^2 + 1.9905P] where P = (Fo^2 + 2Fc^2)/3
6229 reflections	(Δ/σ)max = 0.002
277 parameters	Δρmax = 0.79 e Å^−3
0 restraints	Δρmin = −1.35 e Å^−3

Special details

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
I1	0.284758 (17)	0.587630 (13)	1.10898 (2)	0.05022 (8)
Te1	0.332126 (12)	0.578803 (11)	0.862760 (19)	0.03246 (7)
Si1	0.35690 (5)	0.47194 (5)	0.62668 (8)	0.02888 (17)
Si2	0.16234 (4)	0.49684 (4)	0.67015 (8)	0.02599 (16)
Si3	0.28857 (5)	0.38037 (4)	0.85767 (8)	0.03015 (17)
C1	0.27788 (16)	0.47408 (15)	0.7510 (3)	0.0248 (5)
C2	0.30891 (19)	0.42521 (18)	0.4610 (3)	0.0380 (7)
H2A	0.2922	0.3720	0.4777	0.046*
H2B	0.3505	0.4245	0.4011	0.046*
H2C	0.2588	0.4547	0.4173	0.046*
C3	0.45965 (19)	0.4231 (2)	0.6991 (4)	0.0442 (8)
H3A	0.4496	0.3679	0.7126	0.053*
H3B	0.4845	0.4469	0.7868	0.053*
H3C	0.4988	0.4290	0.6358	0.053*
C4	0.38904 (17)	0.57411 (16)	0.5877 (3)	0.0303 (6)
C5	0.4650 (2)	0.6069 (2)	0.6573 (3)	0.0420 (7)
H5A	0.5002	0.5779	0.7269	0.050*
C6	0.4901 (2)	0.6805 (2)	0.6271 (4)	0.0528 (9)
H6A	0.5411	0.7018	0.6778	0.063*
C7	0.4418 (2)	0.7231 (2)	0.5245 (4)	0.0551 (10)
H7A	0.4590	0.7738	0.5046	0.066*
C8	0.3681 (2)	0.69155 (19)	0.4505 (4)	0.0453 (8)
H8A	0.3351	0.7202	0.3780	0.054*
C9	0.34221 (18)	0.61822 (18)	0.4817 (3)	0.0343 (6)
H9A	0.2914	0.5974	0.4297	0.041*
C10	0.10913 (19)	0.40948 (17)	0.5811 (3)	0.0368 (7)
H10A	0.1020	0.3701	0.6487	0.044*
H10B	0.1440	0.3884	0.5195	0.044*
H10C	0.0534	0.4242	0.5284	0.044*
C11	0.09993 (18)	0.52935 (19)	0.7989 (3)	0.0381 (7)
H11A	0.1012	0.4889	0.8682	0.046*
H11B	0.0411	0.5391	0.7538	0.046*
H11C	0.1247	0.5771	0.8426	0.046*
C12	0.14905 (17)	0.57639 (16)	0.5380 (3)	0.0289 (6)
C13	0.12082 (17)	0.56005 (18)	0.3996 (3)	0.0333 (6)
H13A	0.1122	0.5075	0.3717	0.040*
C14	0.10502 (19)	0.6179 (2)	0.3018 (3)	0.0432 (8)
H14A	0.0858	0.6050	0.2086	0.052*
C15	0.1174 (2)	0.6949 (2)	0.3409 (4)	0.0482 (9)
H15A	0.1074	0.7349	0.2744	0.058*
C16	0.1442 (2)	0.71287 (19)	0.4762 (4)	0.0463 (8)
H16A	0.1524	0.7656	0.5033	0.056*
C17	0.15953 (19)	0.65457 (17)	0.5739 (3)	0.0373 (7)
H17A	0.1775	0.6682	0.6671	0.045*
C18	0.38399 (19)	0.3821 (2)	0.9977 (3)	0.0433 (8)
H18A	0.4342	0.3948	0.9600	0.052*
H18B	0.3915	0.3310	1.0415	0.052*
H18C	0.3764	0.4213	1.0653	0.052*
C19	0.2935 (2)	0.29505 (17)	0.7424 (3)	0.0408 (7)
H19A	0.2427	0.2943	0.6702	0.049*
H19B	0.2964	0.2470	0.7955	0.049*
H19C	0.3440	0.2994	0.7015	0.049*
C20	0.19685 (18)	0.35774 (16)	0.9447 (3)	0.0327 (6)
C21	0.1909 (2)	0.39005 (19)	1.0709 (3)	0.0436 (8)
H21A	0.2332	0.4255	1.1132	0.052*
C22	0.1249 (2)	0.3717 (2)	1.1353 (4)	0.0511 (9)
H22A	0.1223	0.3950	1.2205	0.061*
C23	0.0631 (2)	0.3203 (2)	1.0787 (4)	0.0472 (8)
H23A	0.0170	0.3091	1.1224	0.057*
C24	0.0689 (2)	0.28527 (19)	0.9570 (4)	0.0431 (8)
H24A	0.0274	0.2483	0.9179	0.052*
C25	0.13443 (19)	0.30339 (17)	0.8913 (3)	0.0377 (7)
H25A	0.1373	0.2783	0.8076	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.07253 (17)	0.04763 (14)	0.03456 (13)	−0.00422 (11)	0.02042 (11)	−0.00759 (9)
Te1	0.03236 (11)	0.03485 (11)	0.02977 (11)	−0.00552 (8)	0.00503 (8)	−0.00599 (8)
Si1	0.0240 (4)	0.0349 (4)	0.0282 (4)	0.0025 (3)	0.0063 (3)	−0.0011 (3)
Si2	0.0224 (4)	0.0283 (4)	0.0265 (4)	0.0017 (3)	0.0028 (3)	−0.0002 (3)
Si3	0.0284 (4)	0.0306 (4)	0.0305 (4)	0.0028 (3)	0.0032 (3)	0.0038 (3)
C1	0.0236 (13)	0.0267 (13)	0.0233 (13)	−0.0012 (10)	0.0025 (10)	−0.0022 (11)
C2	0.0384 (17)	0.0429 (18)	0.0334 (16)	0.0023 (13)	0.0082 (13)	−0.0069 (13)
C3	0.0307 (16)	0.055 (2)	0.048 (2)	0.0082 (14)	0.0091 (14)	0.0068 (16)
C4	0.0235 (14)	0.0395 (16)	0.0281 (14)	−0.0045 (11)	0.0055 (11)	−0.0043 (12)
C5	0.0310 (16)	0.0557 (19)	0.0395 (18)	−0.0087 (14)	0.0069 (14)	−0.0031 (15)
C6	0.0353 (18)	0.061 (2)	0.060 (2)	−0.0196 (16)	0.0058 (16)	−0.0139 (19)
C7	0.048 (2)	0.0398 (19)	0.079 (3)	−0.0114 (16)	0.0170 (19)	−0.0023 (19)
C8	0.0422 (19)	0.0391 (18)	0.056 (2)	−0.0001 (14)	0.0128 (16)	0.0060 (16)
C9	0.0273 (15)	0.0408 (17)	0.0359 (16)	−0.0026 (12)	0.0091 (12)	−0.0032 (13)
C10	0.0301 (15)	0.0366 (16)	0.0408 (18)	−0.0021 (12)	−0.0004 (13)	0.0040 (13)
C11	0.0301 (15)	0.0503 (18)	0.0350 (16)	0.0060 (13)	0.0093 (13)	0.0027 (14)
C12	0.0227 (13)	0.0312 (14)	0.0328 (15)	0.0054 (11)	0.0055 (11)	0.0012 (12)
C13	0.0247 (14)	0.0415 (16)	0.0323 (16)	0.0040 (12)	0.0024 (12)	0.0005 (13)
C14	0.0342 (17)	0.062 (2)	0.0328 (17)	0.0080 (15)	0.0059 (13)	0.0112 (16)
C15	0.0395 (18)	0.051 (2)	0.055 (2)	0.0080 (15)	0.0123 (16)	0.0247 (17)
C16	0.0423 (19)	0.0336 (16)	0.063 (2)	0.0067 (14)	0.0096 (16)	0.0099 (16)
C17	0.0360 (16)	0.0334 (16)	0.0418 (17)	0.0077 (12)	0.0055 (13)	−0.0023 (14)
C18	0.0344 (17)	0.0511 (19)	0.0408 (18)	0.0071 (14)	−0.0014 (14)	0.0134 (15)
C19	0.0436 (18)	0.0301 (15)	0.050 (2)	0.0063 (13)	0.0113 (15)	0.0029 (14)
C20	0.0336 (16)	0.0297 (14)	0.0338 (16)	0.0022 (12)	0.0042 (12)	0.0054 (12)
C21	0.052 (2)	0.0395 (17)	0.0402 (18)	−0.0113 (15)	0.0124 (15)	−0.0025 (15)
C22	0.059 (2)	0.050 (2)	0.049 (2)	−0.0040 (17)	0.0229 (18)	−0.0051 (17)
C23	0.0422 (19)	0.052 (2)	0.052 (2)	−0.0004 (15)	0.0188 (16)	0.0137 (17)
C24	0.0352 (17)	0.0426 (18)	0.049 (2)	−0.0062 (14)	0.0023 (15)	0.0115 (15)
C25	0.0441 (18)	0.0362 (16)	0.0307 (16)	−0.0021 (13)	0.0024 (13)	0.0046 (13)

Geometric parameters (Å, º)

I1—Te1	2.7178 (7)	C10—H10C	0.9800
Te1—C1	2.212 (3)	C11—H11A	0.9800
Si1—C2	1.869 (3)	C11—H11B	0.9800
Si1—C3	1.870 (3)	C11—H11C	0.9800
Si1—C4	1.898 (3)	C12—C17	1.397 (4)
Si1—C1	1.942 (3)	C12—C13	1.398 (4)
Si2—C11	1.865 (3)	C13—C14	1.386 (4)
Si2—C10	1.870 (3)	C13—H13A	0.9500
Si2—C12	1.888 (3)	C14—C15	1.387 (5)
Si2—C1	1.917 (3)	C14—H14A	0.9500
Si3—C18	1.866 (3)	C15—C16	1.373 (5)
Si3—C19	1.880 (3)	C15—H15A	0.9500
Si3—C20	1.892 (3)	C16—C17	1.390 (4)
Si3—C1	1.925 (3)	C16—H16A	0.9500
C2—H2A	0.9800	C17—H17A	0.9500
C2—H2B	0.9800	C18—H18A	0.9800
C2—H2C	0.9800	C18—H18B	0.9800
C3—H3A	0.9800	C18—H18C	0.9800
C3—H3B	0.9800	C19—H19A	0.9800
C3—H3C	0.9800	C19—H19B	0.9800
C4—C9	1.400 (4)	C19—H19C	0.9800
C4—C5	1.403 (4)	C20—C21	1.399 (5)
C5—C6	1.382 (5)	C20—C25	1.401 (4)
C5—H5A	0.9500	C21—C22	1.380 (5)
C6—C7	1.373 (5)	C21—H21A	0.9500
C6—H6A	0.9500	C22—C23	1.369 (5)
C7—C8	1.381 (5)	C22—H22A	0.9500
C7—H7A	0.9500	C23—C24	1.378 (5)
C8—C9	1.386 (4)	C23—H23A	0.9500
C8—H8A	0.9500	C24—C25	1.381 (4)
C9—H9A	0.9500	C24—H24A	0.9500
C10—H10A	0.9800	C25—H25A	0.9500
C10—H10B	0.9800
C1—Te1—I1	110.53 (7)	Si2—C10—H10C	109.5
C2—Si1—C3	109.31 (15)	H10A—C10—H10C	109.5
C2—Si1—C4	107.50 (14)	H10B—C10—H10C	109.5
C3—Si1—C4	104.01 (14)	Si2—C11—H11A	109.5
C2—Si1—C1	111.50 (13)	Si2—C11—H11B	109.5
C3—Si1—C1	113.53 (14)	H11A—C11—H11B	109.5
C4—Si1—C1	110.59 (12)	Si2—C11—H11C	109.5
C11—Si2—C10	108.24 (15)	H11A—C11—H11C	109.5
C11—Si2—C12	105.15 (13)	H11B—C11—H11C	109.5
C10—Si2—C12	105.86 (13)	C17—C12—C13	116.7 (3)
C11—Si2—C1	112.17 (13)	C17—C12—Si2	122.0 (2)
C10—Si2—C1	110.61 (13)	C13—C12—Si2	121.1 (2)
C12—Si2—C1	114.38 (12)	C14—C13—C12	122.2 (3)
C18—Si3—C19	110.22 (15)	C14—C13—H13A	118.9
C18—Si3—C20	105.00 (14)	C12—C13—H13A	118.9
C19—Si3—C20	104.46 (14)	C13—C14—C15	119.6 (3)
C18—Si3—C1	111.99 (13)	C13—C14—H14A	120.2
C19—Si3—C1	109.12 (13)	C15—C14—H14A	120.2
C20—Si3—C1	115.72 (12)	C16—C15—C14	119.6 (3)
Si2—C1—Si3	112.36 (13)	C16—C15—H15A	120.2
Si2—C1—Si1	115.75 (14)	C14—C15—H15A	120.2
Si3—C1—Si1	109.82 (13)	C15—C16—C17	120.5 (3)
Si2—C1—Te1	107.49 (12)	C15—C16—H16A	119.7
Si3—C1—Te1	114.96 (12)	C17—C16—H16A	119.7
Si1—C1—Te1	95.50 (11)	C16—C17—C12	121.4 (3)
Si1—C2—H2A	109.5	C16—C17—H17A	119.3
Si1—C2—H2B	109.5	C12—C17—H17A	119.3
H2A—C2—H2B	109.5	Si3—C18—H18A	109.5
Si1—C2—H2C	109.5	Si3—C18—H18B	109.5
H2A—C2—H2C	109.5	H18A—C18—H18B	109.5
H2B—C2—H2C	109.5	Si3—C18—H18C	109.5
Si1—C3—H3A	109.5	H18A—C18—H18C	109.5
Si1—C3—H3B	109.5	H18B—C18—H18C	109.5
H3A—C3—H3B	109.5	Si3—C19—H19A	109.5
Si1—C3—H3C	109.5	Si3—C19—H19B	109.5
H3A—C3—H3C	109.5	H19A—C19—H19B	109.5
H3B—C3—H3C	109.5	Si3—C19—H19C	109.5
C9—C4—C5	116.4 (3)	H19A—C19—H19C	109.5
C9—C4—Si1	122.2 (2)	H19B—C19—H19C	109.5
C5—C4—Si1	121.2 (2)	C21—C20—C25	116.2 (3)
C6—C5—C4	121.7 (3)	C21—C20—Si3	121.9 (2)
C6—C5—H5A	119.2	C25—C20—Si3	121.8 (2)
C4—C5—H5A	119.2	C22—C21—C20	121.5 (3)
C7—C6—C5	120.5 (3)	C22—C21—H21A	119.3
C7—C6—H6A	119.7	C20—C21—H21A	119.3
C5—C6—H6A	119.7	C23—C22—C21	121.2 (3)
C6—C7—C8	119.4 (3)	C23—C22—H22A	119.4
C6—C7—H7A	120.3	C21—C22—H22A	119.4
C8—C7—H7A	120.3	C22—C23—C24	118.8 (3)
C7—C8—C9	120.2 (3)	C22—C23—H23A	120.6
C7—C8—H8A	119.9	C24—C23—H23A	120.6
C9—C8—H8A	119.9	C23—C24—C25	120.6 (3)
C8—C9—C4	121.7 (3)	C23—C24—H24A	119.7
C8—C9—H9A	119.2	C25—C24—H24A	119.7
C4—C9—H9A	119.2	C24—C25—C20	121.7 (3)
Si2—C10—H10A	109.5	C24—C25—H25A	119.1
Si2—C10—H10B	109.5	C20—C25—H25A	119.1
H10A—C10—H10B	109.5
C11—Si2—C1—Si3	71.55 (18)	C9—C4—C5—C6	3.1 (5)
C10—Si2—C1—Si3	−49.41 (18)	Si1—C4—C5—C6	178.3 (3)
C12—Si2—C1—Si3	−168.81 (13)	C4—C5—C6—C7	−1.8 (6)
C11—Si2—C1—Si1	−161.18 (15)	C5—C6—C7—C8	−0.6 (6)
C10—Si2—C1—Si1	77.87 (18)	C6—C7—C8—C9	1.4 (6)
C12—Si2—C1—Si1	−41.54 (18)	C7—C8—C9—C4	0.0 (5)
C11—Si2—C1—Te1	−55.90 (17)	C5—C4—C9—C8	−2.2 (4)
C10—Si2—C1—Te1	−176.85 (13)	Si1—C4—C9—C8	−177.3 (2)
C12—Si2—C1—Te1	63.74 (16)	C11—Si2—C12—C17	47.6 (3)
C18—Si3—C1—Si2	−152.29 (15)	C10—Si2—C12—C17	162.1 (2)
C19—Si3—C1—Si2	85.40 (17)	C1—Si2—C12—C17	−75.9 (3)
C20—Si3—C1—Si2	−32.01 (18)	C11—Si2—C12—C13	−126.7 (2)
C18—Si3—C1—Si1	77.34 (17)	C10—Si2—C12—C13	−12.2 (3)
C19—Si3—C1—Si1	−44.97 (17)	C1—Si2—C12—C13	109.8 (2)
C20—Si3—C1—Si1	−162.38 (13)	C17—C12—C13—C14	0.9 (4)
C18—Si3—C1—Te1	−28.93 (19)	Si2—C12—C13—C14	175.5 (2)
C19—Si3—C1—Te1	−151.24 (14)	C12—C13—C14—C15	0.1 (5)
C20—Si3—C1—Te1	91.35 (16)	C13—C14—C15—C16	−0.8 (5)
C2—Si1—C1—Si2	−39.75 (19)	C14—C15—C16—C17	0.5 (5)
C3—Si1—C1—Si2	−163.74 (15)	C15—C16—C17—C12	0.6 (5)
C4—Si1—C1—Si2	79.80 (16)	C13—C12—C17—C16	−1.3 (4)
C2—Si1—C1—Si3	88.78 (16)	Si2—C12—C17—C16	−175.8 (2)
C3—Si1—C1—Si3	−35.21 (19)	C18—Si3—C20—C21	39.9 (3)
C4—Si1—C1—Si3	−151.68 (12)	C19—Si3—C20—C21	155.9 (3)
C2—Si1—C1—Te1	−152.19 (12)	C1—Si3—C20—C21	−84.1 (3)
C3—Si1—C1—Te1	83.82 (15)	C18—Si3—C20—C25	−135.3 (2)
C4—Si1—C1—Te1	−32.65 (14)	C19—Si3—C20—C25	−19.3 (3)
I1—Te1—C1—Si2	80.09 (12)	C1—Si3—C20—C25	100.7 (2)
I1—Te1—C1—Si3	−45.83 (14)	C25—C20—C21—C22	−2.8 (5)
I1—Te1—C1—Si1	−160.70 (6)	Si3—C20—C21—C22	−178.3 (3)
C2—Si1—C4—C9	34.5 (3)	C20—C21—C22—C23	0.7 (6)
C3—Si1—C4—C9	150.3 (3)	C21—C22—C23—C24	1.8 (5)
C1—Si1—C4—C9	−87.4 (3)	C22—C23—C24—C25	−2.0 (5)
C2—Si1—C4—C5	−140.4 (3)	C23—C24—C25—C20	−0.2 (5)
C3—Si1—C4—C5	−24.5 (3)	C21—C20—C25—C24	2.6 (4)
C1—Si1—C4—C5	97.7 (3)	Si3—C20—C25—C24	178.1 (2)