1,4-Bis[4-(tert-butyl-sulfan-yl)phen-yl]buta-1,3-diyne.

The asymmetric unit of the title compound, C(24)H(26)S(2), consits of one half-mol-ecule, which is located on a center of inversion. The two benzene rings are exactly coplanar while the tert-butyl group is oriented nearly perpendicular to the ring plane [C-S-C-C = -81.14 (11)°].

Related literature

For background to this work, see: Pearson & Tour (1997 ▶); Kergueris et al. (1999 ▶). For related structures, see: Kergueris et al. (1999 ▶); Mayor et al. (2003 ▶). For the synthetic procedure, see: van Dijk et al. (2006 ▶). For the unsubstituted 1,4-diphenyl­buta-1,3-diyne, see: Hori et al. (1987 ▶).

Experimental

Crystal data

C24H26S2

M = 378.57

Monoclinic,

a = 13.6286 (5) Å

b = 6.4269 (2) Å

c = 14.1290 (5) Å

β = 116.937 (2)°

V = 1103.29 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 153 K

0.53 × 0.20 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.881, T max = 0.989

11825 measured reflections

3028 independent reflections

2450 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.091

S = 1.04

3028 reflections

121 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017710/nc2274sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017710/nc2274Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017710/nc2274Isup3.cml

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

C24H26S2	F(000) = 404
Mr = 378.57	Dx = 1.140 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.6286 (5) Å	Cell parameters from 4805 reflections
b = 6.4269 (2) Å	θ = 2.8–30.5°
c = 14.1290 (5) Å	µ = 0.25 mm−1
β = 116.937 (2)°	T = 153 K
V = 1103.29 (7) Å3	Plate, colourless
Z = 2	0.53 × 0.20 × 0.05 mm

Bruker APEXII CCD area-detector diffractometer	3028 independent reflections
Radiation source: fine-focus sealed tube	2450 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
phi and ω scans	θmax = 29.4°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −17→18
Tmin = 0.881, Tmax = 0.989	k = −8→8
11825 measured reflections	l = −19→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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0415P)2 + 0.3498P] where P = (Fo2 + 2Fc2)/3
3028 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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	0.93054 (2)	0.80456 (5)	0.55276 (2)	0.02231 (10)
C1	0.93335 (10)	0.62309 (18)	0.64857 (9)	0.0206 (2)
C2	0.90994 (11)	0.68270 (19)	0.73135 (10)	0.0250 (3)
H2	0.8874	0.8214	0.7343	0.030*
C3	0.91924 (11)	0.5417 (2)	0.80912 (10)	0.0261 (3)
H3	0.9019	0.5832	0.8643	0.031*
C4	0.95429 (10)	0.33764 (19)	0.80637 (10)	0.0234 (3)
C5	0.97762 (11)	0.2782 (2)	0.72369 (10)	0.0257 (3)
H5	1.0013	0.1402	0.7212	0.031*
C6	0.96658 (11)	0.41878 (19)	0.64538 (10)	0.0247 (3)
H6	0.9817	0.3760	0.5890	0.030*
C7	0.78266 (11)	0.8255 (2)	0.45814 (11)	0.0308 (3)
C8	0.73566 (15)	0.6125 (3)	0.41517 (14)	0.0523 (5)
H8A	0.7786	0.5482	0.3831	0.078*
H8B	0.6589	0.6271	0.3614	0.078*
H8C	0.7391	0.5247	0.4733	0.078*
C9	0.78203 (13)	0.9643 (3)	0.37009 (13)	0.0467 (4)
H9A	0.7060	0.9860	0.3159	0.070*
H9B	0.8241	0.8972	0.3378	0.070*
H9C	0.8155	1.0989	0.4001	0.070*
C10	0.72009 (13)	0.9298 (3)	0.51159 (14)	0.0480 (4)
H10A	0.7237	0.8416	0.5697	0.072*
H10B	0.6430	0.9492	0.4595	0.072*
H10C	0.7534	1.0653	0.5399	0.072*
C11	0.97122 (11)	0.1931 (2)	0.88969 (10)	0.0259 (3)
C12	0.98954 (11)	0.0698 (2)	0.95990 (10)	0.0265 (3)

	U11	U22	U33	U12	U13	U23
S1	0.02344 (15)	0.02417 (15)	0.02180 (16)	0.00002 (11)	0.01242 (12)	0.00352 (11)
C1	0.0213 (5)	0.0224 (5)	0.0181 (6)	−0.0005 (4)	0.0090 (5)	0.0011 (4)
C2	0.0327 (7)	0.0210 (6)	0.0255 (6)	0.0017 (5)	0.0169 (5)	0.0000 (5)
C3	0.0347 (7)	0.0264 (6)	0.0222 (6)	0.0008 (5)	0.0173 (5)	−0.0011 (5)
C4	0.0267 (6)	0.0230 (6)	0.0205 (6)	−0.0010 (5)	0.0107 (5)	0.0013 (4)
C5	0.0330 (7)	0.0218 (6)	0.0237 (6)	0.0030 (5)	0.0141 (5)	−0.0002 (5)
C6	0.0307 (6)	0.0257 (6)	0.0212 (6)	0.0022 (5)	0.0148 (5)	−0.0005 (5)
C7	0.0244 (6)	0.0385 (7)	0.0259 (7)	0.0009 (5)	0.0083 (5)	0.0080 (6)
C8	0.0453 (9)	0.0535 (10)	0.0391 (9)	−0.0178 (8)	0.0026 (8)	−0.0021 (8)
C9	0.0375 (8)	0.0616 (11)	0.0362 (8)	0.0078 (7)	0.0125 (7)	0.0244 (8)
C10	0.0305 (8)	0.0661 (11)	0.0508 (10)	0.0153 (8)	0.0215 (7)	0.0150 (9)
C11	0.0321 (6)	0.0246 (6)	0.0235 (6)	0.0000 (5)	0.0147 (5)	−0.0011 (5)
C12	0.0340 (7)	0.0246 (6)	0.0246 (6)	0.0015 (5)	0.0167 (6)	−0.0007 (5)

S1—C1	1.7740 (12)	C7—C9	1.528 (2)
S1—C7	1.8509 (13)	C7—C10	1.526 (2)
C1—C2	1.3980 (17)	C8—H8A	0.9800
C1—C6	1.3964 (17)	C8—H8B	0.9800
C2—C3	1.3852 (17)	C8—H8C	0.9800
C2—H2	0.9500	C9—H9A	0.9800
C3—C4	1.4022 (17)	C9—H9B	0.9800
C3—H3	0.9500	C9—H9C	0.9800
C4—C5	1.3957 (17)	C10—H10A	0.9800
C4—C11	1.4339 (17)	C10—H10B	0.9800
C5—C6	1.3828 (17)	C10—H10C	0.9800
C5—H5	0.9500	C11—C12	1.2042 (18)
C6—H6	0.9500	C12—C12i	1.370 (3)
C7—C8	1.517 (2)
C1—S1—C7	103.83 (6)	C9—C7—S1	103.49 (10)
C2—C1—C6	119.01 (11)	C10—C7—S1	110.13 (10)
C2—C1—S1	121.60 (9)	C7—C8—H8A	109.5
C6—C1—S1	119.27 (9)	C7—C8—H8B	109.5
C3—C2—C1	120.72 (11)	H8A—C8—H8B	109.5
C3—C2—H2	119.6	C7—C8—H8C	109.5
C1—C2—H2	119.6	H8A—C8—H8C	109.5
C2—C3—C4	119.99 (12)	H8B—C8—H8C	109.5
C2—C3—H3	120.0	C7—C9—H9A	109.5
C4—C3—H3	120.0	C7—C9—H9B	109.5
C5—C4—C3	119.25 (11)	H9A—C9—H9B	109.5
C5—C4—C11	119.79 (11)	C7—C9—H9C	109.5
C3—C4—C11	120.89 (11)	H9A—C9—H9C	109.5
C6—C5—C4	120.49 (11)	H9B—C9—H9C	109.5
C6—C5—H5	119.8	C7—C10—H10A	109.5
C4—C5—H5	119.8	C7—C10—H10B	109.5
C5—C6—C1	120.52 (11)	H10A—C10—H10B	109.5
C5—C6—H6	119.7	C7—C10—H10C	109.5
C1—C6—H6	119.7	H10A—C10—H10C	109.5
C8—C7—C9	110.82 (14)	H10B—C10—H10C	109.5
C8—C7—C10	111.40 (14)	C12—C11—C4	177.35 (14)
C9—C7—C10	110.38 (13)	C11—C12—C12i	179.74 (18)
C8—C7—S1	110.35 (11)
C7—S1—C1—C2	−81.14 (11)	C11—C4—C5—C6	−177.00 (12)
C7—S1—C1—C6	103.04 (11)	C4—C5—C6—C1	0.9 (2)
C6—C1—C2—C3	−0.12 (19)	C2—C1—C6—C5	−0.87 (19)
S1—C1—C2—C3	−175.95 (10)	S1—C1—C6—C5	175.06 (10)
C1—C2—C3—C4	1.1 (2)	C1—S1—C7—C8	−55.80 (12)
C2—C3—C4—C5	−1.11 (19)	C1—S1—C7—C9	−174.41 (11)
C2—C3—C4—C11	175.99 (12)	C1—S1—C7—C10	67.60 (12)
C3—C4—C5—C6	0.13 (19)