1,4-Bis[4-(tert-butyl-diphenyl-silyl)buta-1,3-diyn-yl]benzene.

The title centrosymmetric mol-ecule, C(46)H(42)Si(2), is composed of a central benzene ring with buta-1,3-diynyl chains at positions 1 and 4. These chains are terminated by tert-butyl-diphenyl-silyl groups, hence the molecule is dumbbell in shape. The mol-ecules are connected via C-H⋯π inter-actions in the structure, so forming an undulating two-dimensional network in the bc plane. There is also a weak π-π inter-action involving centrosymmetrically related phenyl rings with a centroid-centroid distance of 3.8359 (11) Å.

Related literature

For polyynes and acetyl­enic arrays, see: Ginsburg et al. (1995 ▶); Siemsen et al. (2000 ▶); Brandsma (1988 ▶). For uses and other properties of conjugated carbon–carbon triple bonds, see: Swager (2005 ▶); Tobe & Wakabayashi (2005 ▶); Höger (2005 ▶); Zhou et al. (1994 ▶); Maruyama & Kawabata (1990 ▶); Lee et al. (2000 ▶). For information on the ‘one-pot’ tandem synthesis – Corey–Fuchs reaction/Negishi coupling, see: Corey & Fuchs (1972 ▶); Desai & McKelvie (1962 ▶); King et al. (1977 ▶). For the crystal structure of the trimethyl­silyl analogue, see: Shi Shun et al. (2003 ▶). For the synthesis and crystal structure of related compounds, see: Chalifoux et al. (2009 ▶); Kim (2009 ▶); West et al. (2008 ▶). For a description of the Cambridge Structural Database, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C46H42Si2

M = 650.98

Monoclinic,

a = 8.535 (1) Å

b = 17.2060 (14) Å

c = 13.4923 (14) Å

β = 104.064 (9)°

V = 1922.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 173 K

0.45 × 0.38 × 0.30 mm

Data collection

Stoe IPDS-2 diffractometer

Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009 ▶) T min = 0.919, T max = 1.184

19707 measured reflections

4403 independent reflections

3260 reflections with I > 2σ(I)

R int = 0.098

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.104

S = 0.96

4403 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.29 e Å−3

Data collection: X-AREA (Stoe & Cie, 2009 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000351X/fb2180sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000351X/fb2180Isup2.hkl

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

C46H42Si2	F(000) = 692
Mr = 650.98	Dx = 1.125 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13367 reflections
a = 8.535 (1) Å	θ = 2.0–29.6°
b = 17.2060 (14) Å	µ = 0.12 mm−1
c = 13.4923 (14) Å	T = 173 K
β = 104.064 (9)°	Block, colourless
V = 1922.0 (3) Å3	0.45 × 0.38 × 0.30 mm
Z = 2

Stoe IPDS-2 diffractometer	4403 independent reflections
Radiation source: fine-focus sealed tube	3260 reflections with I > 2σ(I)
graphite	Rint = 0.098
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009)	h = −11→11
Tmin = 0.919, Tmax = 1.184	k = −22→22
19707 measured reflections	l = −16→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: difference Fourier map
wR(F2) = 0.104	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0586P)2] where P = (Fo2 + 2Fc2)/3
4403 reflections	(Δ/σ)max = 0.001
220 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.29 e Å−3
81 constraints

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
Si1	0.21188 (5)	0.33985 (2)	0.45574 (3)	0.0274 (1)
C1	0.17432 (18)	0.37157 (8)	0.57829 (12)	0.0319 (4)
C2	0.15087 (18)	0.39564 (8)	0.65764 (11)	0.0304 (4)
C3	0.12243 (18)	0.42333 (8)	0.74707 (11)	0.0313 (4)
C4	0.09221 (18)	0.44715 (8)	0.82412 (11)	0.0312 (4)
C5	0.04697 (17)	0.47453 (8)	0.91335 (11)	0.0284 (4)
C6	−0.09906 (19)	0.51441 (9)	0.90339 (11)	0.0330 (4)
C7	0.14561 (19)	0.46019 (9)	1.01075 (11)	0.0331 (5)
C8	0.35951 (17)	0.25716 (8)	0.48565 (11)	0.0305 (4)
C9	0.4176 (2)	0.21781 (10)	0.41082 (14)	0.0442 (5)
C10	0.5271 (2)	0.15713 (11)	0.43600 (17)	0.0545 (6)
C11	0.5821 (2)	0.13405 (11)	0.53583 (19)	0.0556 (7)
C12	0.5256 (2)	0.17083 (11)	0.61040 (16)	0.0559 (7)
C13	0.4161 (2)	0.23146 (10)	0.58596 (13)	0.0397 (5)
C14	0.29838 (17)	0.42645 (8)	0.40325 (11)	0.0304 (4)
C15	0.2355 (2)	0.50019 (9)	0.41244 (14)	0.0423 (5)
C16	0.2954 (2)	0.56598 (10)	0.37522 (15)	0.0478 (6)
C17	0.4212 (2)	0.55952 (10)	0.32833 (14)	0.0458 (6)
C18	0.4861 (2)	0.48762 (11)	0.31796 (16)	0.0504 (6)
C19	0.4256 (2)	0.42169 (10)	0.35525 (14)	0.0420 (5)
C20	0.00954 (18)	0.30897 (9)	0.37155 (13)	0.0346 (4)
C21	−0.0513 (2)	0.23744 (11)	0.41817 (17)	0.0535 (7)
C22	0.0254 (2)	0.28984 (12)	0.26356 (14)	0.0521 (6)
C23	−0.1143 (2)	0.37500 (11)	0.36436 (16)	0.0518 (6)
H6	−0.16650	0.52410	0.83740	0.0400*
H7	0.24460	0.43300	1.01790	0.0400*
H9	0.38100	0.23300	0.34130	0.0530*
H10	0.56440	0.13140	0.38380	0.0650*
H11	0.65830	0.09300	0.55310	0.0670*
H12	0.56190	0.15460	0.67950	0.0670*
H13	0.37870	0.25610	0.63890	0.0480*
H15	0.14930	0.50540	0.44510	0.0510*
H16	0.24970	0.61550	0.38200	0.0570*
H17	0.46320	0.60460	0.30320	0.0550*
H18	0.57240	0.48300	0.28520	0.0610*
H19	0.47180	0.37240	0.34790	0.0500*
H21A	−0.06650	0.25060	0.48590	0.0800*
H21B	0.02800	0.19540	0.42450	0.0800*
H21C	−0.15440	0.22050	0.37400	0.0800*
H22A	0.06540	0.33560	0.23410	0.0780*
H22B	−0.08040	0.27500	0.22090	0.0780*
H22C	0.10140	0.24670	0.26660	0.0780*
H23A	−0.12390	0.38880	0.43310	0.0780*
H23B	−0.21950	0.35780	0.32320	0.0780*
H23C	−0.07830	0.42050	0.33220	0.0780*

	U11	U22	U33	U12	U13	U23
Si1	0.0368 (2)	0.0266 (2)	0.0211 (2)	0.0044 (2)	0.0119 (2)	−0.0017 (2)
C1	0.0410 (8)	0.0295 (7)	0.0284 (8)	0.0031 (6)	0.0144 (6)	−0.0001 (6)
C2	0.0400 (8)	0.0268 (7)	0.0270 (8)	0.0025 (6)	0.0131 (6)	0.0007 (5)
C3	0.0434 (8)	0.0276 (7)	0.0251 (7)	0.0022 (6)	0.0128 (6)	0.0007 (5)
C4	0.0443 (8)	0.0256 (7)	0.0258 (8)	0.0017 (6)	0.0126 (6)	0.0002 (5)
C5	0.0414 (8)	0.0238 (6)	0.0222 (7)	−0.0018 (5)	0.0123 (6)	−0.0034 (5)
C6	0.0428 (8)	0.0344 (8)	0.0205 (7)	0.0048 (6)	0.0053 (6)	−0.0006 (5)
C7	0.0385 (8)	0.0343 (8)	0.0274 (8)	0.0069 (6)	0.0099 (6)	−0.0016 (6)
C8	0.0347 (7)	0.0297 (7)	0.0286 (8)	0.0012 (6)	0.0106 (6)	−0.0017 (6)
C9	0.0543 (10)	0.0447 (9)	0.0381 (9)	0.0140 (8)	0.0200 (8)	−0.0009 (7)
C10	0.0552 (10)	0.0494 (10)	0.0658 (13)	0.0164 (9)	0.0279 (10)	−0.0062 (9)
C11	0.0427 (9)	0.0473 (10)	0.0738 (15)	0.0183 (8)	0.0083 (9)	0.0025 (9)
C12	0.0556 (11)	0.0562 (12)	0.0482 (11)	0.0151 (9)	−0.0023 (9)	0.0086 (9)
C13	0.0449 (8)	0.0413 (9)	0.0309 (8)	0.0075 (7)	0.0052 (7)	0.0000 (7)
C14	0.0377 (8)	0.0326 (7)	0.0206 (7)	0.0008 (6)	0.0065 (6)	−0.0013 (5)
C15	0.0587 (10)	0.0329 (8)	0.0408 (10)	0.0019 (7)	0.0230 (8)	−0.0018 (7)
C16	0.0661 (11)	0.0312 (8)	0.0468 (11)	−0.0019 (8)	0.0151 (9)	−0.0006 (7)
C17	0.0515 (10)	0.0422 (9)	0.0400 (10)	−0.0132 (8)	0.0040 (8)	0.0058 (7)
C18	0.0444 (9)	0.0535 (11)	0.0583 (12)	−0.0030 (8)	0.0219 (9)	0.0091 (9)
C19	0.0415 (8)	0.0396 (9)	0.0494 (11)	0.0023 (7)	0.0195 (8)	0.0043 (7)
C20	0.0388 (8)	0.0296 (7)	0.0348 (8)	0.0038 (6)	0.0079 (6)	−0.0041 (6)
C21	0.0524 (10)	0.0420 (10)	0.0671 (14)	−0.0065 (8)	0.0165 (10)	0.0016 (9)
C22	0.0584 (11)	0.0587 (11)	0.0357 (10)	−0.0017 (9)	0.0049 (8)	−0.0165 (8)
C23	0.0429 (9)	0.0461 (10)	0.0598 (13)	0.0130 (8)	−0.0001 (9)	−0.0124 (9)

Si1—C1	1.8418 (16)	C20—C22	1.532 (2)
Si1—C8	1.8782 (15)	C20—C23	1.539 (2)
Si1—C14	1.8764 (15)	C6—H6	0.9500
Si1—C20	1.8978 (17)	C7—H7	0.9500
C1—C2	1.209 (2)	C9—H9	0.9500
C2—C3	1.373 (2)	C10—H10	0.9500
C3—C4	1.202 (2)	C11—H11	0.9500
C4—C5	1.431 (2)	C12—H12	0.9500
C5—C6	1.400 (2)	C13—H13	0.9500
C5—C7	1.400 (2)	C15—H15	0.9500
C6—C7i	1.384 (2)	C16—H16	0.9500
C8—C9	1.402 (2)	C17—H17	0.9500
C8—C13	1.394 (2)	C18—H18	0.9500
C9—C10	1.387 (3)	C19—H19	0.9500
C10—C11	1.373 (3)	C21—H21A	0.9800
C11—C12	1.372 (3)	C21—H21B	0.9800
C12—C13	1.386 (3)	C21—H21C	0.9800
C14—C15	1.395 (2)	C22—H22A	0.9800
C14—C19	1.395 (2)	C22—H22B	0.9800
C15—C16	1.386 (2)	C22—H22C	0.9800
C16—C17	1.377 (3)	C23—H23A	0.9800
C17—C18	1.376 (3)	C23—H23B	0.9800
C18—C19	1.390 (3)	C23—H23C	0.9800
C20—C21	1.529 (3)
C1—Si1—C8	106.60 (7)	C6i—C7—H7	120.00
C1—Si1—C14	105.89 (6)	C8—C9—H9	119.00
C1—Si1—C20	106.78 (7)	C10—C9—H9	119.00
C8—Si1—C14	112.19 (7)	C9—C10—H10	120.00
C8—Si1—C20	112.45 (7)	C11—C10—H10	120.00
C14—Si1—C20	112.38 (7)	C10—C11—H11	120.00
Si1—C1—C2	177.19 (13)	C12—C11—H11	120.00
C1—C2—C3	179.29 (17)	C11—C12—H12	120.00
C2—C3—C4	177.85 (17)	C13—C12—H12	120.00
C3—C4—C5	176.80 (17)	C8—C13—H13	119.00
C4—C5—C6	119.77 (13)	C12—C13—H13	119.00
C4—C5—C7	120.55 (14)	C14—C15—H15	119.00
C6—C5—C7	119.65 (14)	C16—C15—H15	119.00
C5—C6—C7i	120.29 (14)	C15—C16—H16	120.00
C5—C7—C6i	120.06 (15)	C17—C16—H16	120.00
Si1—C8—C9	123.17 (12)	C16—C17—H17	120.00
Si1—C8—C13	120.33 (12)	C18—C17—H17	120.00
C9—C8—C13	116.50 (14)	C17—C18—H18	120.00
C8—C9—C10	121.47 (17)	C19—C18—H18	120.00
C9—C10—C11	120.49 (18)	C14—C19—H19	119.00
C10—C11—C12	119.27 (18)	C18—C19—H19	119.00
C11—C12—C13	120.65 (19)	C20—C21—H21A	109.00
C8—C13—C12	121.63 (16)	C20—C21—H21B	109.00
Si1—C14—C15	119.58 (12)	C20—C21—H21C	110.00
Si1—C14—C19	123.40 (11)	H21A—C21—H21B	110.00
C15—C14—C19	117.02 (14)	H21A—C21—H21C	109.00
C14—C15—C16	121.81 (16)	H21B—C21—H21C	109.00
C15—C16—C17	119.88 (16)	C20—C22—H22A	109.00
C16—C17—C18	119.82 (16)	C20—C22—H22B	109.00
C17—C18—C19	120.17 (17)	C20—C22—H22C	109.00
C14—C19—C18	121.29 (16)	H22A—C22—H22B	109.00
Si1—C20—C21	109.25 (12)	H22A—C22—H22C	109.00
Si1—C20—C22	110.59 (11)	H22B—C22—H22C	109.00
Si1—C20—C23	110.02 (11)	C20—C23—H23A	109.00
C21—C20—C22	109.62 (15)	C20—C23—H23B	109.00
C21—C20—C23	108.87 (14)	C20—C23—H23C	109.00
C22—C20—C23	108.48 (15)	H23A—C23—H23B	109.00
C5—C6—H6	120.00	H23A—C23—H23C	109.00
C7i—C6—H6	120.00	H23B—C23—H23C	109.00
C5—C7—H7	120.00
C1—Si1—C8—C9	−179.84 (13)	C4—C5—C6—C7i	178.71 (14)
C1—Si1—C8—C13	0.69 (15)	C7—C5—C6—C7i	0.2 (2)
C14—Si1—C8—C9	−64.36 (15)	C4—C5—C7—C6i	−178.70 (14)
C14—Si1—C8—C13	116.16 (13)	C6—C5—C7—C6i	−0.2 (2)
C20—Si1—C8—C9	63.47 (15)	C5—C6—C7i—C5i	−0.2 (2)
C20—Si1—C8—C13	−116.00 (13)	Si1—C8—C9—C10	179.77 (13)
C1—Si1—C14—C15	−40.17 (15)	C13—C8—C9—C10	−0.7 (2)
C1—Si1—C14—C19	139.24 (14)	Si1—C8—C13—C12	−179.70 (13)
C8—Si1—C14—C15	−156.07 (13)	C9—C8—C13—C12	0.8 (2)
C8—Si1—C14—C19	23.34 (16)	C8—C9—C10—C11	−0.2 (3)
C20—Si1—C14—C15	76.05 (14)	C9—C10—C11—C12	1.1 (3)
C20—Si1—C14—C19	−104.54 (14)	C10—C11—C12—C13	−1.0 (3)
C1—Si1—C20—C21	−65.38 (13)	C11—C12—C13—C8	0.1 (3)
C1—Si1—C20—C22	173.89 (12)	Si1—C14—C15—C16	179.82 (14)
C1—Si1—C20—C23	54.08 (13)	C19—C14—C15—C16	0.4 (3)
C8—Si1—C20—C21	51.20 (13)	Si1—C14—C19—C18	−179.71 (14)
C8—Si1—C20—C22	−69.54 (13)	C15—C14—C19—C18	−0.3 (3)
C8—Si1—C20—C23	170.66 (11)	C14—C15—C16—C17	−0.5 (3)
C14—Si1—C20—C21	178.93 (11)	C15—C16—C17—C18	0.5 (3)
C14—Si1—C20—C22	58.20 (13)	C16—C17—C18—C19	−0.4 (3)
C14—Si1—C20—C23	−61.61 (14)	C17—C18—C19—C14	0.3 (3)

D	H	Centroid	C—H	H···Cg	D···Cg	D—H···Cg
C6	H6	Cg2i	0.95	2.85	3.7703 (17)	164
C7	H7	Cg1ii	0.95	2.95	3.8516 (18)	160

Table 1

C—H⋯π inter­actions (Å, °)

Cg1 and Cg2 are the centroids of the C8–C13 and C14–C19 rings, respectively.

D	H	Centroid	C—H	H⋯Cg	D⋯Cg	D—H⋯Cg
C6	H6	Cg2i	0.95	2.85	3.7703 (17)	164
C7	H7	Cg1ii	0.95	2.95	3.8516 (18)	160

Symmetry codes: (i) ; (ii) .