2,4,6-Tri-tert-butyl­benzene­tellurenyl iodide

The crystal structure of Mes*TeI (Mes* = 2,4,6-tri-tert-butyl­phen­yl), C₁₈H₂₉ITe, exhibits discrete mol­ecules without Te...I, Te...Te or I...I inter­molecular contacts. The compound was prepared by cleavage of its parent ditellane with iodine, and represents a kinetically stabilized arenetellurenyl iodide with a very bulky substituent. The mol­ecule possesses an angular C—Te—I arrangement [95.75 (8)°] with a Te—I single bond [2.7181 (6) Å].

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C)= 0.005 Å
• R factor = 0.026
• wR factor = 0.062
• Data-to-parameter ratio = 19.8

checkCIF/PLATON results

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Computing details

Data collection: IPDS EXPOSE (Stoe & Cie, 1996); 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.

2,4,6-tri-tert-butylbenzenetellurenyl iodide

Crystal data

C18H29ITe	F(000) = 968
Mr = 499.93	Monoclinic P (as derived from metrics)
Monoclinic, P21/c	Dx = 1.702 Mg m^−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.805 (4) Å	Cell parameters from 5000 reflections
b = 6.0230 (12) Å	θ = 2.3–25.9°
c = 18.504 (4) Å	µ = 3.10 mm^−1
β = 100.47 (3)°	T = 200 K
V = 1951.3 (7) Å^3	Rod, green
Z = 4	0.35 × 0.08 × 0.05 mm

Data collection

Stoe IPDS diffractometer	3761 independent reflections
Radiation source: fine focus sealed tube	3019 reflections with I > 2σ(I)
Vertically mounted graphite crystal monochromator	Rint = 0.059
Detector resolution: 9 pixels mm^-1	θmax = 25.9°, θmin = 2.2°
area detection scans	h = −21→19
Absorption correction: numerical [X-SHAPE (Stoe & Cie, 1997) and X-RED (Stoe & Cie, 1997)]	k = −7→7
Tmin = 0.543, Tmax = 0.877	l = −22→22
13085 measured 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.062	H-atom parameters constrained
S = 0.93	w = 1/[σ^2(Fo^2) + (0.0328P)^2] where P = (Fo^2 + 2Fc^2)/3
3761 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.65 e Å^−3
0 restraints	Δρmin = −1.18 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	0.058437 (16)	−0.28743 (4)	0.457323 (16)	0.04187 (9)
Te1	0.109947 (13)	0.12292 (4)	0.429442 (13)	0.02854 (8)
C1	0.21151 (17)	0.0086 (5)	0.39299 (17)	0.0214 (7)
C2	0.27798 (19)	−0.0348 (6)	0.44561 (18)	0.0250 (7)
C3	0.33431 (19)	−0.1653 (6)	0.42373 (18)	0.0250 (7)
H3A	0.3786	−0.1994	0.4590	0.030*
C4	0.32902 (18)	−0.2475 (5)	0.35348 (18)	0.0225 (7)
C5	0.26654 (18)	−0.1817 (5)	0.30197 (18)	0.0214 (7)
H5A	0.2638	−0.2292	0.2526	0.026*
C6	0.20772 (17)	−0.0507 (5)	0.31812 (17)	0.0207 (6)
C7	0.2959 (2)	0.0599 (6)	0.52533 (19)	0.0314 (8)
C8	0.2844 (3)	0.3146 (7)	0.5240 (2)	0.0436 (10)
H8A	0.2300	0.3486	0.5088	0.052*
H8B	0.3132	0.3814	0.4892	0.052*
H8C	0.3026	0.3751	0.5732	0.052*
C9	0.2495 (2)	−0.0528 (7)	0.5767 (2)	0.0398 (9)
H9A	0.1956	−0.0113	0.5625	0.048*
H9B	0.2685	−0.0052	0.6274	0.048*
H9C	0.2546	−0.2143	0.5732	0.048*
C10	0.3802 (2)	0.0253 (9)	0.5606 (2)	0.0511 (11)
H10A	0.4130	0.0863	0.5283	0.061*
H10B	0.3905	−0.1338	0.5679	0.061*
H10C	0.3909	0.1014	0.6082	0.061*
C11	0.14562 (18)	0.0304 (6)	0.25335 (18)	0.0251 (7)
C12	0.1337 (2)	0.2830 (6)	0.2566 (2)	0.0321 (8)
H12A	0.1114	0.3195	0.2998	0.039*
H12B	0.0991	0.3317	0.2121	0.039*
H12C	0.1829	0.3585	0.2600	0.039*
C13	0.0696 (2)	−0.0939 (6)	0.2498 (2)	0.0345 (8)
H13A	0.0476	−0.0569	0.2932	0.041*
H13B	0.0786	−0.2543	0.2487	0.041*
H13C	0.0340	−0.0498	0.2053	0.041*
C14	0.1706 (2)	−0.0122 (7)	0.1795 (2)	0.0402 (10)
H14A	0.1334	0.0542	0.1398	0.048*
H14B	0.1735	−0.1725	0.1713	0.048*
H14C	0.2209	0.0546	0.1801	0.048*
C15	0.39101 (18)	−0.3948 (6)	0.3307 (2)	0.0268 (7)
C16	0.4519 (2)	−0.4625 (8)	0.3954 (2)	0.0478 (11)
H16A	0.4754	−0.3294	0.4203	0.057*
H16B	0.4911	−0.5511	0.3777	0.057*
H16C	0.4286	−0.5509	0.4299	0.057*
C17	0.4294 (2)	−0.2661 (7)	0.2758 (3)	0.0479 (11)
H17A	0.4520	−0.1294	0.2989	0.057*
H17B	0.3912	−0.2287	0.2324	0.057*
H17C	0.4694	−0.3581	0.2610	0.057*
C18	0.3553 (2)	−0.6085 (6)	0.2945 (2)	0.0371 (9)
H18A	0.3162	−0.5705	0.2519	0.045*
H18B	0.3319	−0.6924	0.3300	0.045*
H18C	0.3950	−0.6989	0.2785	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.04868 (16)	0.02551 (13)	0.05811 (18)	−0.00995 (11)	0.02748 (13)	0.00115 (12)
Te1	0.03344 (13)	0.01826 (12)	0.04003 (14)	0.00111 (9)	0.02296 (10)	−0.00119 (10)
C1	0.0246 (16)	0.0165 (16)	0.0265 (17)	−0.0011 (12)	0.0137 (13)	0.0008 (13)
C2	0.0319 (17)	0.0224 (16)	0.0238 (17)	−0.0077 (14)	0.0133 (14)	−0.0001 (14)
C3	0.0252 (17)	0.0265 (18)	0.0232 (17)	−0.0038 (13)	0.0042 (13)	0.0023 (14)
C4	0.0214 (15)	0.0188 (16)	0.0290 (18)	−0.0019 (13)	0.0095 (13)	0.0002 (13)
C5	0.0234 (16)	0.0210 (16)	0.0209 (16)	−0.0005 (13)	0.0067 (13)	−0.0029 (13)
C6	0.0214 (15)	0.0197 (15)	0.0231 (16)	−0.0023 (13)	0.0094 (12)	−0.0010 (13)
C7	0.041 (2)	0.0324 (19)	0.0225 (17)	−0.0107 (16)	0.0093 (15)	−0.0064 (15)
C8	0.061 (3)	0.036 (2)	0.037 (2)	−0.019 (2)	0.018 (2)	−0.0129 (18)
C9	0.057 (2)	0.041 (2)	0.0240 (18)	−0.011 (2)	0.0148 (17)	0.0000 (17)
C10	0.053 (3)	0.070 (3)	0.028 (2)	−0.010 (2)	0.0012 (19)	−0.014 (2)
C11	0.0234 (16)	0.0246 (17)	0.0279 (17)	0.0005 (14)	0.0065 (13)	0.0017 (14)
C12	0.0267 (18)	0.0288 (18)	0.042 (2)	0.0010 (15)	0.0084 (15)	0.0111 (17)
C13	0.0295 (18)	0.028 (2)	0.044 (2)	−0.0017 (15)	0.0015 (16)	−0.0006 (16)
C14	0.039 (2)	0.055 (3)	0.0253 (19)	0.0160 (19)	0.0026 (16)	0.0012 (18)
C15	0.0218 (16)	0.0246 (18)	0.0355 (19)	0.0022 (14)	0.0096 (14)	−0.0008 (15)
C16	0.029 (2)	0.057 (3)	0.055 (3)	0.0164 (19)	0.0014 (18)	−0.004 (2)
C17	0.041 (2)	0.043 (2)	0.070 (3)	0.0097 (18)	0.036 (2)	0.011 (2)
C18	0.0335 (19)	0.030 (2)	0.049 (2)	0.0062 (16)	0.0099 (17)	−0.0059 (17)

Geometric parameters (Å, º)

I1—Te1	2.7181 (6)	C11—C14	1.534 (5)
Te1—C1	2.155 (3)	C11—C13	1.538 (5)
C1—C2	1.414 (5)	C11—C12	1.539 (5)
C1—C6	1.420 (4)	C12—H12A	0.9800
C2—C3	1.391 (5)	C12—H12B	0.9800
C2—C7	1.560 (5)	C12—H12C	0.9800
C3—C4	1.378 (5)	C13—H13A	0.9800
C3—H3A	0.9500	C13—H13B	0.9800
C4—C5	1.385 (5)	C13—H13C	0.9800
C4—C15	1.534 (4)	C14—H14A	0.9800
C5—C6	1.386 (4)	C14—H14B	0.9800
C5—H5A	0.9500	C14—H14C	0.9800
C6—C11	1.554 (5)	C15—C16	1.518 (5)
C7—C9	1.527 (5)	C15—C17	1.534 (5)
C7—C10	1.539 (6)	C15—C18	1.534 (5)
C7—C8	1.547 (6)	C16—H16A	0.9800
C8—H8A	0.9800	C16—H16B	0.9800
C8—H8B	0.9800	C16—H16C	0.9800
C8—H8C	0.9800	C17—H17A	0.9800
C9—H9A	0.9800	C17—H17B	0.9800
C9—H9B	0.9800	C17—H17C	0.9800
C9—H9C	0.9800	C18—H18A	0.9800
C10—H10A	0.9800	C18—H18B	0.9800
C10—H10B	0.9800	C18—H18C	0.9800
C10—H10C	0.9800
C1—Te1—I1	95.75 (8)	C14—C11—C6	110.7 (3)
C2—C1—C6	120.7 (3)	C13—C11—C6	112.1 (3)
C2—C1—Te1	119.3 (2)	C12—C11—C6	111.4 (3)
C6—C1—Te1	119.5 (2)	C11—C12—H12A	109.5
C3—C2—C1	117.5 (3)	C11—C12—H12B	109.5
C3—C2—C7	116.6 (3)	H12A—C12—H12B	109.5
C1—C2—C7	125.9 (3)	C11—C12—H12C	109.5
C4—C3—C2	123.2 (3)	H12A—C12—H12C	109.5
C4—C3—H3A	118.4	H12B—C12—H12C	109.5
C2—C3—H3A	118.4	C11—C13—H13A	109.5
C3—C4—C5	117.1 (3)	C11—C13—H13B	109.5
C3—C4—C15	122.5 (3)	H13A—C13—H13B	109.5
C5—C4—C15	120.3 (3)	C11—C13—H13C	109.5
C4—C5—C6	123.9 (3)	H13A—C13—H13C	109.5
C4—C5—H5A	118.0	H13B—C13—H13C	109.5
C6—C5—H5A	118.0	C11—C14—H14A	109.5
C5—C6—C1	116.7 (3)	C11—C14—H14B	109.5
C5—C6—C11	118.2 (3)	H14A—C14—H14B	109.5
C1—C6—C11	125.0 (3)	C11—C14—H14C	109.5
C9—C7—C10	105.8 (3)	H14A—C14—H14C	109.5
C9—C7—C8	111.4 (3)	H14B—C14—H14C	109.5
C10—C7—C8	104.9 (3)	C16—C15—C4	112.7 (3)
C9—C7—C2	112.7 (3)	C16—C15—C17	108.5 (3)
C10—C7—C2	111.6 (3)	C4—C15—C17	108.6 (3)
C8—C7—C2	110.1 (3)	C16—C15—C18	107.4 (3)
C7—C8—H8A	109.5	C4—C15—C18	110.1 (3)
C7—C8—H8B	109.5	C17—C15—C18	109.5 (3)
H8A—C8—H8B	109.5	C15—C16—H16A	109.5
C7—C8—H8C	109.5	C15—C16—H16B	109.5
H8A—C8—H8C	109.5	H16A—C16—H16B	109.5
H8B—C8—H8C	109.5	C15—C16—H16C	109.5
C7—C9—H9A	109.5	H16A—C16—H16C	109.5
C7—C9—H9B	109.5	H16B—C16—H16C	109.5
H9A—C9—H9B	109.5	C15—C17—H17A	109.5
C7—C9—H9C	109.5	C15—C17—H17B	109.5
H9A—C9—H9C	109.5	H17A—C17—H17B	109.5
H9B—C9—H9C	109.5	C15—C17—H17C	109.5
C7—C10—H10A	109.5	H17A—C17—H17C	109.5
C7—C10—H10B	109.5	H17B—C17—H17C	109.5
H10A—C10—H10B	109.5	C15—C18—H18A	109.5
C7—C10—H10C	109.5	C15—C18—H18B	109.5
H10A—C10—H10C	109.5	H18A—C18—H18B	109.5
H10B—C10—H10C	109.5	C15—C18—H18C	109.5
C14—C11—C13	106.1 (3)	H18A—C18—H18C	109.5
C14—C11—C12	105.3 (3)	H18B—C18—H18C	109.5
C13—C11—C12	110.9 (3)
I1—Te1—C1—C2	−84.8 (2)	C3—C2—C7—C9	−108.2 (4)
I1—Te1—C1—C6	86.6 (2)	C1—C2—C7—C9	74.9 (5)
C6—C1—C2—C3	−9.2 (5)	C3—C2—C7—C10	10.7 (5)
Te1—C1—C2—C3	162.1 (2)	C1—C2—C7—C10	−166.2 (3)
C6—C1—C2—C7	167.7 (3)	C3—C2—C7—C8	126.7 (3)
Te1—C1—C2—C7	−21.0 (4)	C1—C2—C7—C8	−50.1 (4)
C1—C2—C3—C4	1.8 (5)	C5—C6—C11—C14	−11.9 (4)
C7—C2—C3—C4	−175.3 (3)	C1—C6—C11—C14	164.5 (3)
C2—C3—C4—C5	4.6 (5)	C5—C6—C11—C13	106.3 (3)
C2—C3—C4—C15	−178.8 (3)	C1—C6—C11—C13	−77.3 (4)
C3—C4—C5—C6	−4.0 (5)	C5—C6—C11—C12	−128.8 (3)
C15—C4—C5—C6	179.3 (3)	C1—C6—C11—C12	47.6 (4)
C4—C5—C6—C1	−3.0 (5)	C3—C4—C15—C16	7.5 (5)
C4—C5—C6—C11	173.7 (3)	C5—C4—C15—C16	−176.1 (3)
C2—C1—C6—C5	9.7 (5)	C3—C4—C15—C17	−112.8 (4)
Te1—C1—C6—C5	−161.6 (2)	C5—C4—C15—C17	63.7 (4)
C2—C1—C6—C11	−166.8 (3)	C3—C4—C15—C18	127.4 (3)
Te1—C1—C6—C11	22.0 (4)	C5—C4—C15—C18	−56.2 (4)