2,2'-[2,5-Bis(hex-yloxy)-1,4-phenyl-ene]dithio-phene.

The asymmetric unit of the title compound, C(26)H(34)O(2)S(2), comprises one half-mol-ecule located on an inversion centre. The thio-phene groups are twisted relative to the benzene ring, making a dihedral angle of 5.30 (7)°, and the n-hexyl groups are in a fully extended conformation. In the crystal, there are short C-H⋯π contacts involving the thio-phene groups.

Related literature

For the synthesis and general background references, see: Carle et al. (2010 ▶); Promarak & Ruchirawat (2007 ▶); Bouachrine et al. (2002 ▶).

Experimental

Crystal data

C26H34O2S2

M = 442.65

Monoclinic,

a = 12.2996 (3) Å

b = 5.4298 (1) Å

c = 17.6872 (4) Å

β = 103.982 (2)°

V = 1146.23 (4) Å3

Z = 2

Cu Kα radiation

μ = 2.25 mm−1

T = 150 K

0.26 × 0.11 × 0.03 mm

Data collection

Oxford Diffraction Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.592, T max = 0.935

8010 measured reflections

2216 independent reflections

2018 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.113

S = 1.04

2216 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); 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, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681202404X/gk2496sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202404X/gk2496Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202404X/gk2496Isup3.cml

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

C26H34O2S2	F(000) = 476
Mr = 442.65	Dx = 1.283 Mg m−3
Monoclinic, P21/c	Melting point = 369–367 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 12.2996 (3) Å	Cell parameters from 3985 reflections
b = 5.4298 (1) Å	θ = 4–71°
c = 17.6872 (4) Å	µ = 2.25 mm−1
β = 103.982 (2)°	T = 150 K
V = 1146.23 (4) Å3	Thin plate, colourless
Z = 2	0.26 × 0.11 × 0.03 mm

Oxford Diffraction Gemini diffractometer	2216 independent reflections
Radiation source: fine-focus sealed tube	2018 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scans	θmax = 71.3°, θmin = 3.7°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	h = −15→14
Tmin = 0.592, Tmax = 0.935	k = −6→6
8010 measured reflections	l = −21→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0739P)2 + 0.5049P] where P = (Fo2 + 2Fc2)/3
2216 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer 1986) with a nominal stability of 0.1 K.Cosier, J. & Glazer, A.M., (1986)., J. Appl. Cryst.105 107.

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	0.29977 (3)	0.23308 (7)	0.14406 (2)	0.02015 (17)
O1	0.33781 (9)	0.3460 (2)	0.00566 (6)	0.0185 (3)
C1	0.41842 (12)	0.1767 (3)	0.00089 (8)	0.0151 (3)
C2	0.44944 (12)	0.0140 (3)	0.06456 (8)	0.0146 (3)
C3	0.46770 (12)	0.1612 (3)	−0.06175 (8)	0.0153 (3)
H3	0.4451	0.2703	−0.1031	0.018*
C4	0.39762 (12)	0.0159 (3)	0.13132 (8)	0.0144 (3)
C5	0.41723 (12)	−0.1539 (3)	0.19221 (8)	0.0163 (3)
H5	0.4667	−0.2856	0.1962	0.020*
C6	0.35315 (13)	−0.1034 (3)	0.24751 (9)	0.0190 (3)
H6	0.3560	−0.1990	0.2916	0.023*
C7	0.28728 (13)	0.0999 (3)	0.22898 (9)	0.0205 (3)
H7	0.2408	0.1595	0.2592	0.025*
C8	0.30066 (12)	0.5135 (3)	−0.05794 (8)	0.0161 (3)
H8A	0.2722	0.4229	−0.1059	0.019*
H8B	0.3624	0.6160	−0.0643	0.019*
C9	0.20894 (12)	0.6715 (3)	−0.03966 (8)	0.0162 (3)
H9A	0.2394	0.7674	0.0069	0.019*
H9B	0.1504	0.5663	−0.0294	0.019*
C10	0.15873 (13)	0.8453 (3)	−0.10717 (9)	0.0173 (3)
H10A	0.2181	0.9460	−0.1184	0.021*
H10B	0.1269	0.7482	−0.1532	0.021*
C11	0.06820 (13)	1.0129 (3)	−0.09008 (9)	0.0180 (3)
H11A	0.1007	1.1141	−0.0451	0.022*
H11B	0.0102	0.9122	−0.0770	0.022*
C12	0.01499 (13)	1.1804 (3)	−0.15839 (9)	0.0206 (3)
H12A	0.0732	1.2796	−0.1718	0.025*
H12B	−0.0182	1.0791	−0.2032	0.025*
C13	−0.07480 (13)	1.3507 (3)	−0.14123 (10)	0.0237 (4)
H13A	−0.1337	1.2538	−0.1291	0.036*
H13B	−0.1050	1.4511	−0.1861	0.036*
H13C	−0.0422	1.4544	−0.0977	0.036*

	U11	U22	U33	U12	U13	U23
S1	0.0231 (3)	0.0238 (3)	0.0156 (2)	0.00695 (14)	0.00873 (17)	0.00228 (13)
O1	0.0210 (6)	0.0222 (6)	0.0139 (5)	0.0084 (4)	0.0074 (4)	0.0046 (4)
C1	0.0131 (7)	0.0172 (7)	0.0143 (7)	0.0013 (6)	0.0021 (5)	−0.0007 (6)
C2	0.0135 (7)	0.0185 (7)	0.0117 (7)	−0.0007 (6)	0.0028 (5)	−0.0012 (5)
C3	0.0166 (7)	0.0174 (7)	0.0115 (7)	0.0015 (6)	0.0022 (5)	0.0024 (5)
C4	0.0126 (7)	0.0175 (7)	0.0124 (7)	0.0002 (5)	0.0016 (5)	−0.0023 (5)
C5	0.0158 (7)	0.0220 (8)	0.0119 (7)	−0.0011 (6)	0.0049 (6)	−0.0027 (6)
C6	0.0197 (7)	0.0247 (8)	0.0128 (7)	−0.0018 (6)	0.0042 (6)	0.0007 (6)
C7	0.0211 (8)	0.0286 (8)	0.0138 (7)	0.0016 (6)	0.0079 (6)	−0.0008 (6)
C8	0.0175 (7)	0.0189 (7)	0.0116 (7)	0.0033 (6)	0.0030 (5)	0.0018 (5)
C9	0.0165 (7)	0.0184 (7)	0.0139 (7)	0.0018 (6)	0.0040 (6)	−0.0001 (6)
C10	0.0184 (7)	0.0188 (7)	0.0146 (7)	0.0028 (6)	0.0039 (6)	0.0008 (6)
C11	0.0188 (7)	0.0181 (7)	0.0170 (7)	0.0019 (6)	0.0041 (6)	−0.0003 (6)
C12	0.0193 (8)	0.0235 (8)	0.0193 (8)	0.0048 (6)	0.0054 (6)	0.0026 (6)
C13	0.0207 (8)	0.0236 (8)	0.0257 (8)	0.0060 (6)	0.0037 (6)	0.0011 (7)

S1—C7	1.7071 (15)	C8—H8A	0.9700
S1—C4	1.7380 (15)	C8—H8B	0.9700
O1—C1	1.3697 (18)	C9—C10	1.530 (2)
O1—C8	1.4326 (17)	C9—H9A	0.9700
C1—C3	1.388 (2)	C9—H9B	0.9700
C1—C2	1.409 (2)	C10—C11	1.524 (2)
C2—C3i	1.404 (2)	C10—H10A	0.9700
C2—C4	1.471 (2)	C10—H10B	0.9700
C3—C2i	1.404 (2)	C11—C12	1.527 (2)
C3—H3	0.9300	C11—H11A	0.9700
C4—C5	1.394 (2)	C11—H11B	0.9700
C5—C6	1.423 (2)	C12—C13	1.526 (2)
C5—H5	0.9300	C12—H12A	0.9700
C6—C7	1.362 (2)	C12—H12B	0.9700
C6—H6	0.9300	C13—H13A	0.9600
C7—H7	0.9300	C13—H13B	0.9600
C8—C9	1.513 (2)	C13—H13C	0.9600
C7—S1—C4	92.24 (7)	C8—C9—H9A	109.4
C1—O1—C8	118.42 (11)	C10—C9—H9A	109.4
O1—C1—C3	123.50 (14)	C8—C9—H9B	109.4
O1—C1—C2	115.58 (13)	C10—C9—H9B	109.4
C3—C1—C2	120.92 (14)	H9A—C9—H9B	108.0
C3i—C2—C1	117.07 (13)	C11—C10—C9	112.96 (12)
C3i—C2—C4	119.49 (13)	C11—C10—H10A	109.0
C1—C2—C4	123.42 (13)	C9—C10—H10A	109.0
C1—C3—C2i	122.00 (14)	C11—C10—H10B	109.0
C1—C3—H3	119.0	C9—C10—H10B	109.0
C2i—C3—H3	119.0	H10A—C10—H10B	107.8
C5—C4—C2	126.00 (13)	C10—C11—C12	113.12 (13)
C5—C4—S1	110.17 (11)	C10—C11—H11A	109.0
C2—C4—S1	123.82 (11)	C12—C11—H11A	109.0
C4—C5—C6	112.47 (14)	C10—C11—H11B	109.0
C4—C5—H5	123.8	C12—C11—H11B	109.0
C6—C5—H5	123.8	H11A—C11—H11B	107.8
C7—C6—C5	112.76 (14)	C13—C12—C11	113.32 (13)
C7—C6—H6	123.6	C13—C12—H12A	108.9
C5—C6—H6	123.6	C11—C12—H12A	108.9
C6—C7—S1	112.35 (12)	C13—C12—H12B	108.9
C6—C7—H7	123.8	C11—C12—H12B	108.9
S1—C7—H7	123.8	H12A—C12—H12B	107.7
O1—C8—C9	107.75 (11)	C12—C13—H13A	109.5
O1—C8—H8A	110.2	C12—C13—H13B	109.5
C9—C8—H8A	110.2	H13A—C13—H13B	109.5
O1—C8—H8B	110.2	C12—C13—H13C	109.5
C9—C8—H8B	110.2	H13A—C13—H13C	109.5
H8A—C8—H8B	108.5	H13B—C13—H13C	109.5
C8—C9—C10	111.36 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1ii	0.93	2.85	3.5809 (16)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1, C4–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg1i	0.93	2.85	3.5809 (16)	137

Symmetry code: (i) .