(Z,Z)-1,4-Diiodo-1,4-bis-(trimethyl-silyl)buta-1,3-diene.

The asymmetric unit of the title compound, C(10)H(20)I(2)Si(2), contains two half-mol-ecules. Both complete molecules are generated by crystallographic inversion centers located at the mid-points of the central C-C single bonds; the butadiene groups are planar, with a trans conformation about the central C-C bond. The mol-ecules show short intra-molecular H⋯I contacts of 2.89 and 2.92 Å. The crystal packing shows no short inter-molecular contacts.

Related literature

For the synthesis of the title compound, see: Yamaguchi et al. (1998 ▶). For related structures, see: Saito et al. (2007 ▶); Yamamoto et al. (2002 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

C10H20I2Si2

M = 450.24

Triclinic,

a = 6.3553 (17) Å

b = 11.502 (2) Å

c = 11.698 (2) Å

α = 103.027 (13)°

β = 90.555 (17)°

γ = 90.99 (2)°

V = 832.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 3.89 mm−1

T = 155 (2) K

0.46 × 0.36 × 0.28 mm

Data collection

Siemens SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.275, T max = 0.336

15331 measured reflections

5837 independent reflections

5272 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.059

S = 1.03

5837 reflections

134 parameters

H-atom parameters constrained

Δρmax = 1.12 e Å−3

Δρmin = −0.94 e Å−3

Data collection: SMART (Siemens, 1995 ▶); cell refinement: SMART; data reduction: SAINT (Siemens, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803482X/su2074sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803482X/su2074Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H20I2Si2	Z = 2
Mr = 450.24	F(000) = 428
Triclinic, P1	Dx = 1.795 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3553 (17) Å	Cell parameters from 124 reflections
b = 11.502 (2) Å	θ = 3–23°
c = 11.698 (2) Å	µ = 3.89 mm−1
α = 103.027 (13)°	T = 155 K
β = 90.555 (17)°	Block, colorless
γ = 90.99 (2)°	0.46 × 0.36 × 0.28 mm
V = 832.9 (3) Å3

Siemens SMART 1K CCD diffractometer	5837 independent reflections
Radiation source: normal-focus sealed tube	5272 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 32.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −9→9
Tmin = 0.275, Tmax = 0.336	k = −17→17
15331 measured reflections	l = −17→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021	H-atom parameters constrained
wR(F2) = 0.059	w = 1/[σ2(Fo2) + (0.02P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.002
5837 reflections	Δρmax = 1.12 e Å−3
134 parameters	Δρmin = −0.94 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0130 (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.

	x	y	z	Uiso*/Ueq
I1	0.631493 (18)	0.679368 (10)	0.508829 (10)	0.02900 (4)
I2	0.124665 (17)	0.825214 (9)	0.402449 (9)	0.02623 (4)
Si1	0.76330 (7)	0.63323 (4)	0.77198 (4)	0.02223 (9)
Si2	0.47343 (7)	0.86551 (4)	0.19545 (4)	0.02225 (9)
C1	0.9715 (3)	0.51656 (14)	0.56130 (13)	0.0211 (3)
H1	1.0502	0.4804	0.6129	0.025*
C2	0.8224 (2)	0.59143 (13)	0.61143 (13)	0.0198 (3)
C3	0.9030 (3)	0.53065 (18)	0.84764 (16)	0.0321 (4)
H3A	0.8575	0.5446	0.9293	0.048*
H3B	1.0552	0.5455	0.8458	0.048*
H3C	0.8702	0.4478	0.8077	0.048*
C4	0.8577 (4)	0.79022 (18)	0.8278 (2)	0.0405 (5)
H4A	0.8270	0.8157	0.9116	0.061*
H4B	0.7858	0.8422	0.7848	0.061*
H4C	1.0098	0.7953	0.8165	0.061*
C5	0.4740 (3)	0.62065 (18)	0.79288 (17)	0.0322 (4)
H5A	0.4456	0.6250	0.8759	0.048*
H5B	0.4206	0.5442	0.7457	0.048*
H5C	0.4037	0.6862	0.7680	0.048*
C6	0.5181 (3)	0.98312 (14)	0.43727 (13)	0.0221 (3)
H6	0.6391	1.0180	0.4103	0.027*
C7	0.4013 (3)	0.90828 (14)	0.35421 (13)	0.0210 (3)
C8	0.6036 (3)	0.71790 (16)	0.16638 (17)	0.0332 (4)
H8A	0.7252	0.7220	0.2194	0.050*
H8B	0.6506	0.6974	0.0849	0.050*
H8C	0.5034	0.6567	0.1796	0.050*
C9	0.6592 (3)	0.98330 (18)	0.16797 (18)	0.0361 (4)
H9A	0.7846	0.9870	0.2182	0.054*
H9B	0.5901	1.0607	0.1859	0.054*
H9C	0.7005	0.9641	0.0854	0.054*
C10	0.2345 (3)	0.85504 (18)	0.09994 (16)	0.0342 (4)
H10A	0.2759	0.8370	0.0174	0.051*
H10B	0.1613	0.9312	0.1182	0.051*
H10C	0.1404	0.7914	0.1139	0.051*

	U11	U22	U33	U12	U13	U23
I1	0.02999 (7)	0.03118 (7)	0.02837 (7)	0.01194 (4)	0.00029 (5)	0.01117 (5)
I2	0.02378 (7)	0.02802 (7)	0.02598 (6)	−0.00570 (4)	−0.00083 (4)	0.00471 (4)
Si1	0.0211 (2)	0.0241 (2)	0.01973 (19)	0.00282 (16)	0.00184 (15)	0.00115 (16)
Si2	0.0263 (2)	0.0217 (2)	0.01793 (19)	0.00165 (16)	0.00037 (16)	0.00277 (15)
C1	0.0221 (7)	0.0224 (7)	0.0191 (6)	0.0036 (5)	0.0002 (5)	0.0049 (5)
C2	0.0193 (7)	0.0203 (7)	0.0200 (6)	0.0019 (5)	−0.0005 (5)	0.0046 (5)
C3	0.0302 (9)	0.0438 (10)	0.0248 (8)	0.0096 (7)	0.0031 (7)	0.0123 (7)
C4	0.0426 (12)	0.0312 (9)	0.0408 (11)	−0.0023 (8)	−0.0044 (9)	−0.0063 (8)
C5	0.0224 (9)	0.0423 (10)	0.0307 (9)	0.0045 (7)	0.0053 (7)	0.0050 (7)
C6	0.0213 (7)	0.0223 (7)	0.0217 (7)	−0.0019 (5)	0.0011 (5)	0.0030 (5)
C7	0.0219 (7)	0.0203 (7)	0.0207 (7)	0.0013 (5)	0.0008 (5)	0.0045 (5)
C8	0.0414 (11)	0.0279 (9)	0.0284 (8)	0.0081 (7)	−0.0002 (7)	0.0021 (7)
C9	0.0410 (11)	0.0339 (9)	0.0349 (9)	−0.0020 (8)	0.0109 (8)	0.0108 (8)
C10	0.0387 (11)	0.0388 (10)	0.0245 (8)	0.0034 (8)	−0.0048 (7)	0.0060 (7)

I1—C2	2.1207 (16)	C4—H4B	0.9800
I2—C7	2.1276 (17)	C4—H4C	0.9800
Si1—C3	1.8591 (19)	C5—H5A	0.9800
Si1—C4	1.863 (2)	C5—H5B	0.9800
Si1—C5	1.8647 (19)	C5—H5C	0.9800
Si1—C2	1.8742 (16)	C6—C7	1.350 (2)
Si2—C10	1.863 (2)	C6—C6ii	1.453 (3)
Si2—C8	1.8644 (19)	C6—H6	0.9500
Si2—C9	1.866 (2)	C8—H8A	0.9800
Si2—C7	1.8744 (16)	C8—H8B	0.9800
C1—C2	1.339 (2)	C8—H8C	0.9800
C1—C1i	1.450 (3)	C9—H9A	0.9800
C1—H1	0.9500	C9—H9B	0.9800
C3—H3A	0.9800	C9—H9C	0.9800
C3—H3B	0.9800	C10—H10A	0.9800
C3—H3C	0.9800	C10—H10B	0.9800
C4—H4A	0.9800	C10—H10C	0.9800
C3—Si1—C4	110.85 (10)	Si1—C5—H5A	109.5
C3—Si1—C5	109.79 (9)	Si1—C5—H5B	109.5
C4—Si1—C5	110.45 (10)	H5A—C5—H5B	109.5
C3—Si1—C2	109.04 (8)	Si1—C5—H5C	109.5
C4—Si1—C2	107.21 (9)	H5A—C5—H5C	109.5
C5—Si1—C2	109.45 (8)	H5B—C5—H5C	109.5
C10—Si2—C8	109.30 (9)	C7—C6—C6ii	128.06 (19)
C10—Si2—C9	110.53 (10)	C7—C6—H6	116.0
C8—Si2—C9	110.39 (10)	C6ii—C6—H6	116.0
C10—Si2—C7	110.61 (9)	C6—C7—Si2	123.88 (12)
C8—Si2—C7	108.94 (8)	C6—C7—I2	119.83 (12)
C9—Si2—C7	107.04 (8)	Si2—C7—I2	116.23 (8)
C2—C1—C1i	128.56 (19)	Si2—C8—H8A	109.5
C2—C1—H1	115.7	Si2—C8—H8B	109.5
C1i—C1—H1	115.7	H8A—C8—H8B	109.5
C1—C2—Si1	126.01 (12)	Si2—C8—H8C	109.5
C1—C2—I1	120.61 (12)	H8A—C8—H8C	109.5
Si1—C2—I1	113.35 (8)	H8B—C8—H8C	109.5
Si1—C3—H3A	109.5	Si2—C9—H9A	109.5
Si1—C3—H3B	109.5	Si2—C9—H9B	109.5
H3A—C3—H3B	109.5	H9A—C9—H9B	109.5
Si1—C3—H3C	109.5	Si2—C9—H9C	109.5
H3A—C3—H3C	109.5	H9A—C9—H9C	109.5
H3B—C3—H3C	109.5	H9B—C9—H9C	109.5
Si1—C4—H4A	109.5	Si2—C10—H10A	109.5
Si1—C4—H4B	109.5	Si2—C10—H10B	109.5
H4A—C4—H4B	109.5	H10A—C10—H10B	109.5
Si1—C4—H4C	109.5	Si2—C10—H10C	109.5
H4A—C4—H4C	109.5	H10A—C10—H10C	109.5
H4B—C4—H4C	109.5	H10B—C10—H10C	109.5
C1i—C1—C2—Si1	−178.07 (17)	C6ii—C6—C7—Si2	−176.55 (18)
C1i—C1—C2—I1	0.2 (3)	C6ii—C6—C7—I2	0.6 (3)
C3—Si1—C2—C1	−12.13 (17)	C10—Si2—C7—C6	−141.69 (15)
C4—Si1—C2—C1	107.93 (16)	C8—Si2—C7—C6	98.15 (16)
C5—Si1—C2—C1	−132.25 (15)	C9—Si2—C7—C6	−21.21 (17)
C3—Si1—C2—I1	169.49 (8)	C10—Si2—C7—I2	41.11 (11)
C4—Si1—C2—I1	−70.44 (11)	C8—Si2—C7—I2	−79.04 (11)
C5—Si1—C2—I1	49.37 (11)	C9—Si2—C7—I2	161.59 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···I1i	0.95	2.92	3.394 (2)	112
C6—H6···I2ii	0.95	2.89	3.378 (2)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯I1i	0.95	2.92	3.394 (2)	112
C6—H6⋯I2ii	0.95	2.89	3.378 (2)	113

Symmetry codes: (i) ; (ii) .