4,4'-Bis[2-(3,4-dibutyl-2-thienylethyn-yl)]biphen-yl.

The mol-ecule of the title compound, C(40)H(46)S(2), reveals C(i) symmetry. An inversion centre is located at the mid-point of the C-C bond of the biphenyl unit; the asymmetric unit comprises one-half of the mol-ecule. The conjugated backbone is nearly planar, with a mean deviation of 0.041 Å.

Related literature

For general background, see: Brad Wan et al. (2000 ▶); Cornil et al. (2001 ▶); Grosshenny et al. (1997 ▶); Huang & Tour (1998 ▶); Tour (1996 ▶). For related structures, see: Baudour (1972 ▶); Charbonneau & Delugeard (1977 ▶); Domenicano et al. (1975 ▶); Robertson (1961 ▶). For the synthesis, see: Liu et al. (2005 ▶).

Experimental

Crystal data

C40H46S2

M = 590.89

Triclinic,

a = 9.2040 (18) Å

b = 9.3640 (19) Å

c = 10.582 (2) Å

α = 85.69 (3)°

β = 85.18 (3)°

γ = 69.41 (3)°

V = 849.7 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.18 mm−1

T = 293 (2) K

0.62 × 0.40 × 0.07 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995 ▶) T min = 0.805, T max = 0.992

3595 measured reflections

3595 independent reflections

2287 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.241

S = 1.07

3595 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.42 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2001 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: SHELXTL.

Crystal structure: contains datablocks 070712a, I. DOI: 10.1107/S1600536808036143/kp2189sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036143/kp2189Isup2.hkl

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

C40H46S2	V = 849.7 (3) Å3
Mr = 590.89	Z = 1
Triclinic, P1	F000 = 318
a = 9.2040 (18) Å	Dx = 1.155 Mg m−3
b = 9.3640 (19) Å	Mo Kα radiation λ = 0.71073 Å
c = 10.582 (2) Å	µ = 0.18 mm−1
α = 85.69 (3)º	T = 293 (2) K
β = 85.18 (3)º	Neddle, yellow
γ = 69.41 (3)º	0.62 × 0.40 × 0.07 mm

Rigaku R-AXIS RAPID IP diffractometer	3595 independent reflections
Radiation source: fine-focus sealed tube	2287 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.0000
Detector resolution: 0.76 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 2.3º
Oscillation scans	h = 0→11
Absorption correction: empirical (using intensity measurements)(ABSCOR; Higashi, 1995)	k = −10→12
Tmin = 0.805, Tmax = 0.992	l = −13→13
3595 measured reflections

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)] = 0.067	H-atom parameters constrained
wR(F2) = 0.241	w = 1/[σ2(Fo2) + (0.1672P)2 + 0.1626P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3595 reflections	Δρmax = 0.44 e Å−3
190 parameters	Δρmin = −0.42 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
S1	0.34733 (8)	0.37884 (8)	0.02833 (7)	0.0512 (3)
C1	−0.2000 (4)	0.5223 (4)	0.3588 (3)	0.0657 (9)
H1A	−0.1334	0.5778	0.3558	0.079*
C2	−0.3290 (4)	0.5588 (4)	0.4443 (3)	0.0615 (8)
H2A	−0.3467	0.6388	0.4973	0.074*
C3	−0.4314 (3)	0.4808 (3)	0.4534 (2)	0.0393 (5)
C4	−0.4016 (4)	0.3655 (4)	0.3702 (4)	0.0750 (12)
H4A	−0.4696	0.3116	0.3721	0.090*
C5	−0.2733 (4)	0.3276 (5)	0.2840 (4)	0.0816 (13)
H5A	−0.2573	0.2494	0.2295	0.098*
C6	−0.1694 (3)	0.4041 (3)	0.2779 (2)	0.0439 (6)
C7	−0.0335 (3)	0.3631 (3)	0.1922 (3)	0.0476 (6)
C8	0.0798 (3)	0.3289 (3)	0.1211 (2)	0.0440 (6)
C9	0.2138 (3)	0.2853 (3)	0.0369 (2)	0.0415 (6)
C10	0.2565 (3)	0.1695 (3)	−0.0473 (2)	0.0387 (5)
C11	0.3994 (3)	0.1568 (3)	−0.1180 (2)	0.0419 (6)
C12	0.4587 (3)	0.2635 (3)	−0.0862 (3)	0.0497 (7)
H12	0.5507	0.2720	−0.1235	0.060*
C13	0.1620 (3)	0.0701 (3)	−0.0634 (3)	0.0463 (6)
H13A	0.0948	0.0719	0.0126	0.056*
H13B	0.2317	−0.0344	−0.0728	0.056*
C14	0.4717 (3)	0.0371 (3)	−0.2152 (3)	0.0515 (7)
H14A	0.4910	−0.0630	−0.1731	0.062*
H14B	0.3969	0.0498	−0.2784	0.062*
C15	0.0618 (3)	0.1215 (3)	−0.1791 (3)	0.0503 (6)
H15A	0.1267	0.1352	−0.2527	0.060*
H15B	0.0233	0.0412	−0.1960	0.060*
C16	0.6214 (3)	0.0406 (3)	−0.2825 (3)	0.0498 (7)
H16A	0.6965	0.0293	−0.2201	0.060*
H16B	0.6025	0.1390	−0.3274	0.060*
C17	−0.0748 (3)	0.2680 (4)	−0.1618 (3)	0.0575 (7)
H17A	−0.0376	0.3445	−0.1336	0.069*
H17B	−0.1465	0.2501	−0.0953	0.069*
C18	0.6894 (3)	−0.0855 (4)	−0.3767 (3)	0.0604 (8)
H18A	0.7095	−0.1838	−0.3314	0.073*
H18B	0.6131	−0.0752	−0.4380	0.073*
C19	−0.1626 (4)	0.3311 (4)	−0.2807 (3)	0.0680 (9)
H19A	−0.2477	0.4233	−0.2623	0.102*
H19B	−0.2019	0.2571	−0.3085	0.102*
H19C	−0.0936	0.3526	−0.3464	0.102*
C20	0.8373 (5)	−0.0823 (6)	−0.4465 (4)	0.0866 (13)
H20A	0.8747	−0.1641	−0.5037	0.130*
H20B	0.9140	−0.0944	−0.3866	0.130*
H20C	0.8177	0.0135	−0.4937	0.130*

	U11	U22	U33	U12	U13	U23
S1	0.0432 (4)	0.0556 (4)	0.0568 (5)	−0.0203 (3)	0.0164 (3)	−0.0206 (3)
C1	0.0576 (17)	0.080 (2)	0.070 (2)	−0.0398 (16)	0.0352 (15)	−0.0323 (17)
C2	0.0596 (17)	0.0696 (18)	0.0622 (18)	−0.0334 (15)	0.0336 (14)	−0.0329 (15)
C3	0.0314 (11)	0.0457 (12)	0.0341 (11)	−0.0071 (9)	0.0110 (9)	−0.0058 (9)
C4	0.0615 (18)	0.088 (2)	0.090 (2)	−0.0447 (18)	0.0481 (18)	−0.055 (2)
C5	0.068 (2)	0.090 (2)	0.097 (3)	−0.0424 (19)	0.054 (2)	−0.062 (2)
C6	0.0326 (11)	0.0505 (14)	0.0415 (13)	−0.0084 (10)	0.0130 (10)	−0.0066 (10)
C7	0.0395 (13)	0.0532 (14)	0.0433 (14)	−0.0099 (11)	0.0122 (11)	−0.0087 (11)
C8	0.0372 (12)	0.0506 (14)	0.0393 (13)	−0.0113 (11)	0.0109 (10)	−0.0059 (10)
C9	0.0326 (11)	0.0477 (13)	0.0404 (12)	−0.0116 (10)	0.0126 (10)	−0.0065 (10)
C10	0.0321 (11)	0.0443 (12)	0.0366 (12)	−0.0116 (9)	0.0080 (9)	−0.0025 (9)
C11	0.0315 (11)	0.0488 (13)	0.0406 (13)	−0.0098 (10)	0.0118 (9)	−0.0082 (10)
C12	0.0360 (12)	0.0596 (15)	0.0526 (15)	−0.0182 (11)	0.0201 (11)	−0.0148 (12)
C13	0.0430 (13)	0.0452 (13)	0.0514 (14)	−0.0190 (11)	0.0110 (11)	−0.0048 (11)
C14	0.0385 (13)	0.0582 (16)	0.0552 (16)	−0.0142 (12)	0.0173 (11)	−0.0212 (13)
C15	0.0452 (13)	0.0580 (15)	0.0509 (15)	−0.0225 (12)	0.0100 (11)	−0.0140 (12)
C16	0.0374 (13)	0.0617 (16)	0.0442 (14)	−0.0113 (12)	0.0149 (11)	−0.0129 (12)
C17	0.0475 (15)	0.0641 (18)	0.0589 (17)	−0.0165 (13)	0.0028 (13)	−0.0116 (14)
C18	0.0478 (15)	0.077 (2)	0.0428 (15)	−0.0039 (14)	0.0070 (12)	−0.0187 (14)
C19	0.0546 (18)	0.080 (2)	0.068 (2)	−0.0214 (17)	−0.0071 (15)	−0.0038 (17)
C20	0.063 (2)	0.111 (3)	0.061 (2)	−0.003 (2)	0.0313 (17)	−0.018 (2)

S1—C12	1.702 (3)	C13—H13A	0.9700
S1—C9	1.735 (3)	C13—H13B	0.9700
C1—C6	1.385 (4)	C14—C16	1.507 (3)
C1—C2	1.387 (4)	C14—H14A	0.9700
C1—H1A	0.9300	C14—H14B	0.9700
C2—C3	1.375 (4)	C15—C17	1.511 (4)
C2—H2A	0.9300	C15—H15A	0.9700
C3—C4	1.382 (4)	C15—H15B	0.9700
C3—C3i	1.490 (4)	C16—C18	1.527 (4)
C4—C5	1.387 (4)	C16—H16A	0.9700
C4—H4A	0.9300	C16—H16B	0.9700
C5—C6	1.377 (4)	C17—C19	1.519 (5)
C5—H5A	0.9300	C17—H17A	0.9700
C6—C7	1.435 (3)	C17—H17B	0.9700
C7—C8	1.193 (3)	C18—C20	1.502 (5)
C8—C9	1.414 (3)	C18—H18A	0.9700
C9—C10	1.382 (3)	C18—H18B	0.9700
C10—C11	1.428 (3)	C19—H19A	0.9600
C10—C13	1.507 (4)	C19—H19B	0.9600
C11—C12	1.369 (4)	C19—H19C	0.9600
C11—C14	1.514 (3)	C20—H20A	0.9600
C12—H12	0.9300	C20—H20B	0.9600
C13—C15	1.539 (4)	C20—H20C	0.9600
C12—S1—C9	91.29 (12)	C11—C14—H14A	108.5
C6—C1—C2	120.7 (3)	C16—C14—H14B	108.5
C6—C1—H1A	119.7	C11—C14—H14B	108.5
C2—C1—H1A	119.7	H14A—C14—H14B	107.5
C3—C2—C1	122.4 (3)	C17—C15—C13	113.7 (2)
C3—C2—H2A	118.8	C17—C15—H15A	108.8
C1—C2—H2A	118.8	C13—C15—H15A	108.8
C2—C3—C4	116.4 (2)	C17—C15—H15B	108.8
C2—C3—C3i	122.1 (3)	C13—C15—H15B	108.8
C4—C3—C3i	121.5 (3)	H15A—C15—H15B	107.7
C3—C4—C5	122.0 (3)	C14—C16—C18	112.4 (2)
C3—C4—H4A	119.0	C14—C16—H16A	109.1
C5—C4—H4A	119.0	C18—C16—H16A	109.1
C6—C5—C4	121.1 (3)	C14—C16—H16B	109.1
C6—C5—H5A	119.5	C18—C16—H16B	109.1
C4—C5—H5A	119.5	H16A—C16—H16B	107.9
C5—C6—C1	117.5 (2)	C15—C17—C19	114.3 (3)
C5—C6—C7	121.7 (2)	C15—C17—H17A	108.7
C1—C6—C7	120.8 (2)	C19—C17—H17A	108.7
C8—C7—C6	179.8 (4)	C15—C17—H17B	108.7
C7—C8—C9	178.8 (3)	C19—C17—H17B	108.7
C10—C9—C8	126.9 (2)	H17A—C17—H17B	107.6
C10—C9—S1	111.52 (17)	C20—C18—C16	113.2 (3)
C8—C9—S1	121.6 (2)	C20—C18—H18A	108.9
C9—C10—C11	112.0 (2)	C16—C18—H18A	108.9
C9—C10—C13	123.8 (2)	C20—C18—H18B	108.9
C11—C10—C13	124.2 (2)	C16—C18—H18B	108.9
C12—C11—C10	111.9 (2)	H18A—C18—H18B	107.7
C12—C11—C14	126.0 (2)	C17—C19—H19A	109.5
C10—C11—C14	122.0 (2)	C17—C19—H19B	109.5
C11—C12—S1	113.24 (18)	H19A—C19—H19B	109.5
C11—C12—H12	123.4	C17—C19—H19C	109.5
S1—C12—H12	123.4	H19A—C19—H19C	109.5
C10—C13—C15	112.8 (2)	H19B—C19—H19C	109.5
C10—C13—H13A	109.0	C18—C20—H20A	109.5
C15—C13—H13A	109.0	C18—C20—H20B	109.5
C10—C13—H13B	109.0	H20A—C20—H20B	109.5
C15—C13—H13B	109.0	C18—C20—H20C	109.5
H13A—C13—H13B	107.8	H20A—C20—H20C	109.5
C16—C14—C11	115.3 (2)	H20B—C20—H20C	109.5
C16—C14—H14A	108.5
C12—C11—C10—C9	−0.6 (4)	C4—C5—C6—C1	−1.5 (1)
C12—S1—C9—C10	0.1 (8)	C1—C2—C3—C4	−1.6 (0)
C10—C11—C12—S1	0.5 (1)	C5—C4—C3—C2	1.5 (0)
C11—C12—S1—C9	−0.2 (0)	C5—C6—C1—C2	1.4 (2)
C11—C10—C9—S1	0.4 (9)	C9—C8—C7—C6	93.5 (2)
C11—C10—C9—C8	−179.9 (8)	C10—C9—C8—C7	24.6 (9)
C12—S1—C9—C8	−179.7 (4)	S1—C9—C8—C7	−155.8 (2)
C7—C6—C5—C4	177.9 (5)	C5—C6—C7—C8	−117.5 (4)
C7—C6—C1—C2	−178.0 (5)	C1—C6—C7—C8	61.9 (0)
C6—C5—C4—C3	0.0 (4)	C4—C3—C3—C4	90.0 (0)
C6—C1—C2—C3	0.1 (5)