Dimethyl 2,5-bis-(5-hexyl-thio-phen-2-yl)benzene-1,4-dioate.

In the title compound, C(30)H(38)O(4)S(2), the centroid of the benzene ring lies on a center of inversion. The thio-phene ring is aligned at 49.8 (1)° with respect to the benzene ring. The alkyl chain adopts an extended zigzag conformation.

Related literature

The title compound and its derivatives are used in the preparation of organic semiconductors. For applications of these materials, see: Tian et al. (2010 ▶); Zhang et al. (2010 ▶). For the synthesis of related compounds, see: Fraind & Tovar (2010 ▶); Gurthrie & Tovar (2008 ▶), Hotta (2001 ▶); Kang et al. (1997 ▶); Lois et al. (2007 ▶); Shao & Zhao (2009 ▶); Zhao et al. (2007 ▶).

Experimental

Crystal data

C30H38O4S2

M = 526.72

Monoclinic,

a = 15.617 (6) Å

b = 8.083 (3) Å

c = 11.585 (4) Å

β = 104.470 (4)°

V = 1416.0 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.35 × 0.32 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.927, T max = 0.959

6083 measured reflections

2490 independent reflections

1865 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.104

S = 1.04

2490 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536811011718/ng5141sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011718/ng5141Isup2.hkl

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

C30H38O4S2	F(000) = 564
Mr = 526.72	Dx = 1.235 Mg m−3
Monoclinic, P2/c	Melting point: 362 K
Hall symbol: -P 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 15.617 (6) Å	Cell parameters from 1616 reflections
b = 8.083 (3) Å	θ = 2.5–25.8°
c = 11.585 (4) Å	µ = 0.22 mm−1
β = 104.470 (4)°	T = 293 K
V = 1416.0 (9) Å3	Block, colorless
Z = 2	0.35 × 0.32 × 0.19 mm

Bruker APEXII CCD diffractometer	2490 independent reflections
Radiation source: fine-focus sealed tube	1865 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→18
Tmin = 0.927, Tmax = 0.959	k = −8→9
6083 measured reflections	l = −13→13

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.1877P] where P = (Fo2 + 2Fc2)/3
2490 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.23 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
C1	0.07441 (12)	0.8250 (2)	−0.01209 (17)	0.0320 (5)
C2	0.03976 (12)	0.6534 (2)	−0.00661 (17)	0.0301 (4)
C3	0.07574 (12)	0.5472 (2)	0.08892 (16)	0.0309 (5)
C4	0.15632 (12)	0.5867 (2)	0.18357 (17)	0.0329 (5)
C5	0.16918 (13)	0.5716 (3)	0.30285 (18)	0.0411 (5)
H5	0.1254	0.5364	0.3388	0.049*
C6	0.25579 (14)	0.6143 (3)	0.36780 (19)	0.0457 (6)
H6	0.2739	0.6121	0.4506	0.055*
C7	0.30953 (12)	0.6585 (2)	0.29820 (18)	0.0364 (5)
C8	0.40559 (13)	0.7071 (3)	0.3327 (2)	0.0480 (6)
H8A	0.4122	0.8115	0.2946	0.058*
H8B	0.4393	0.6246	0.3020	0.058*
C9	0.44453 (13)	0.7245 (3)	0.4653 (2)	0.0472 (6)
H9A	0.4376	0.6205	0.5037	0.057*
H9B	0.4115	0.8080	0.4960	0.057*
C10	0.54203 (14)	0.7720 (3)	0.4984 (2)	0.0504 (6)
H10A	0.5750	0.6890	0.4672	0.060*
H10B	0.5489	0.8764	0.4604	0.060*
C11	0.58113 (14)	0.7884 (3)	0.6310 (2)	0.0539 (6)
H11A	0.5466	0.8688	0.6621	0.065*
H11B	0.5752	0.6830	0.6682	0.065*
C12	0.67691 (15)	0.8399 (3)	0.6673 (2)	0.0581 (7)
H12A	0.7115	0.7618	0.6342	0.070*
H12B	0.6827	0.9475	0.6330	0.070*
C13	0.71464 (18)	0.8491 (3)	0.7999 (2)	0.0792 (9)
H13A	0.6816	0.9277	0.8334	0.119*
H13B	0.7754	0.8833	0.8164	0.119*
H13C	0.7111	0.7422	0.8345	0.119*
C14	0.03448 (12)	0.3957 (2)	0.09348 (17)	0.0327 (5)
H14	0.0574	0.3248	0.1569	0.039*
C15	0.11166 (16)	1.0295 (3)	−0.1356 (2)	0.0549 (6)
H15A	0.0682	1.1060	−0.1218	0.082*
H15B	0.1181	1.0434	−0.2153	0.082*
H15C	0.1673	1.0503	−0.0797	0.082*
O1	0.08339 (9)	0.86154 (16)	−0.12051 (12)	0.0441 (4)
O2	0.09033 (9)	0.91985 (17)	0.07033 (12)	0.0444 (4)
S1	0.25288 (3)	0.65154 (7)	0.15037 (5)	0.0447 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0258 (10)	0.0378 (11)	0.0301 (12)	−0.0019 (8)	0.0026 (9)	−0.0002 (9)
C2	0.0278 (10)	0.0345 (10)	0.0280 (11)	−0.0041 (8)	0.0071 (8)	−0.0029 (9)
C3	0.0264 (10)	0.0364 (11)	0.0283 (12)	−0.0025 (8)	0.0039 (8)	−0.0035 (9)
C4	0.0285 (10)	0.0340 (10)	0.0337 (12)	−0.0047 (8)	0.0031 (9)	−0.0004 (9)
C5	0.0347 (12)	0.0546 (13)	0.0321 (13)	−0.0116 (10)	0.0048 (9)	0.0031 (10)
C6	0.0422 (13)	0.0577 (14)	0.0311 (13)	−0.0109 (10)	−0.0025 (10)	0.0009 (10)
C7	0.0282 (10)	0.0383 (11)	0.0379 (13)	−0.0035 (9)	−0.0010 (9)	−0.0023 (9)
C8	0.0298 (11)	0.0531 (13)	0.0562 (16)	−0.0086 (10)	0.0017 (11)	−0.0064 (11)
C9	0.0319 (12)	0.0486 (13)	0.0535 (15)	−0.0053 (10)	−0.0032 (11)	−0.0030 (11)
C10	0.0336 (12)	0.0491 (13)	0.0603 (17)	−0.0045 (10)	−0.0037 (11)	−0.0043 (12)
C11	0.0404 (13)	0.0528 (14)	0.0580 (17)	−0.0087 (11)	−0.0072 (12)	0.0015 (12)
C12	0.0387 (13)	0.0582 (15)	0.0659 (18)	−0.0052 (11)	−0.0086 (12)	−0.0039 (13)
C13	0.0651 (18)	0.085 (2)	0.066 (2)	−0.0177 (15)	−0.0225 (15)	0.0089 (16)
C14	0.0298 (10)	0.0379 (11)	0.0279 (11)	−0.0003 (8)	0.0023 (9)	0.0011 (9)
C15	0.0672 (16)	0.0483 (14)	0.0546 (16)	−0.0134 (12)	0.0257 (13)	0.0083 (11)
O1	0.0577 (10)	0.0423 (9)	0.0349 (9)	−0.0128 (7)	0.0162 (7)	−0.0015 (6)
O2	0.0542 (9)	0.0409 (8)	0.0345 (9)	−0.0097 (7)	0.0039 (7)	−0.0071 (7)
S1	0.0315 (3)	0.0660 (4)	0.0355 (4)	−0.0110 (3)	0.0062 (2)	−0.0034 (3)

C1—O2	1.201 (2)	C9—H9B	0.9700
C1—O1	1.331 (2)	C10—C11	1.510 (3)
C1—C2	1.496 (3)	C10—H10A	0.9700
C2—C14i	1.390 (3)	C10—H10B	0.9700
C2—C3	1.403 (3)	C11—C12	1.508 (3)
C3—C14	1.391 (3)	C11—H11A	0.9700
C3—C4	1.483 (2)	C11—H11B	0.9700
C4—C5	1.351 (3)	C12—C13	1.503 (3)
C4—S1	1.728 (2)	C12—H12A	0.9700
C5—C6	1.416 (3)	C12—H12B	0.9700
C5—H5	0.9300	C13—H13A	0.9600
C6—C7	1.349 (3)	C13—H13B	0.9600
C6—H6	0.9300	C13—H13C	0.9600
C7—C8	1.505 (3)	C14—C2i	1.390 (3)
C7—S1	1.721 (2)	C14—H14	0.9300
C8—C9	1.511 (3)	C15—O1	1.452 (2)
C8—H8A	0.9700	C15—H15A	0.9600
C8—H8B	0.9700	C15—H15B	0.9600
C9—C10	1.523 (3)	C15—H15C	0.9600
C9—H9A	0.9700
O2—C1—O1	123.96 (18)	C11—C10—H10A	108.8
O2—C1—C2	124.28 (18)	C9—C10—H10A	108.8
O1—C1—C2	111.74 (16)	C11—C10—H10B	108.8
C14i—C2—C3	119.57 (16)	C9—C10—H10B	108.8
C14i—C2—C1	118.65 (16)	H10A—C10—H10B	107.7
C3—C2—C1	121.56 (16)	C12—C11—C10	115.4 (2)
C14—C3—C2	118.10 (17)	C12—C11—H11A	108.4
C14—C3—C4	118.50 (17)	C10—C11—H11A	108.4
C2—C3—C4	123.39 (17)	C12—C11—H11B	108.4
C5—C4—C3	128.22 (18)	C10—C11—H11B	108.4
C5—C4—S1	109.88 (14)	H11A—C11—H11B	107.5
C3—C4—S1	121.82 (14)	C13—C12—C11	114.0 (2)
C4—C5—C6	113.54 (19)	C13—C12—H12A	108.7
C4—C5—H5	123.2	C11—C12—H12A	108.7
C6—C5—H5	123.2	C13—C12—H12B	108.7
C7—C6—C5	113.65 (19)	C11—C12—H12B	108.7
C7—C6—H6	123.2	H12A—C12—H12B	107.6
C5—C6—H6	123.2	C12—C13—H13A	109.5
C6—C7—C8	129.7 (2)	C12—C13—H13B	109.5
C6—C7—S1	110.14 (15)	H13A—C13—H13B	109.5
C8—C7—S1	120.20 (16)	C12—C13—H13C	109.5
C7—C8—C9	114.55 (19)	H13A—C13—H13C	109.5
C7—C8—H8A	108.6	H13B—C13—H13C	109.5
C9—C8—H8A	108.6	C2i—C14—C3	122.33 (18)
C7—C8—H8B	108.6	C2i—C14—H14	118.8
C9—C8—H8B	108.6	C3—C14—H14	118.8
H8A—C8—H8B	107.6	O1—C15—H15A	109.5
C8—C9—C10	113.74 (19)	O1—C15—H15B	109.5
C8—C9—H9A	108.8	H15A—C15—H15B	109.5
C10—C9—H9A	108.8	O1—C15—H15C	109.5
C8—C9—H9B	108.8	H15A—C15—H15C	109.5
C10—C9—H9B	108.8	H15B—C15—H15C	109.5
H9A—C9—H9B	107.7	C1—O1—C15	115.35 (16)
C11—C10—C9	113.8 (2)	C7—S1—C4	92.78 (10)
O2—C1—C2—C14i	129.1 (2)	C5—C6—C7—S1	1.1 (2)
O1—C1—C2—C14i	−49.3 (2)	C6—C7—C8—C9	−6.6 (3)
O2—C1—C2—C3	−45.5 (3)	S1—C7—C8—C9	174.20 (15)
O1—C1—C2—C3	136.11 (18)	C7—C8—C9—C10	179.42 (19)
C14i—C2—C3—C14	−0.7 (3)	C8—C9—C10—C11	−179.62 (19)
C1—C2—C3—C14	173.85 (17)	C9—C10—C11—C12	−178.4 (2)
C14i—C2—C3—C4	178.01 (17)	C10—C11—C12—C13	−177.9 (2)
C1—C2—C3—C4	−7.4 (3)	C2—C3—C14—C2i	0.7 (3)
C14—C3—C4—C5	−48.0 (3)	C4—C3—C14—C2i	−178.05 (17)
C2—C3—C4—C5	133.3 (2)	O2—C1—O1—C15	−2.0 (3)
C14—C3—C4—S1	128.25 (17)	C2—C1—O1—C15	176.42 (16)
C2—C3—C4—S1	−50.5 (2)	C6—C7—S1—C4	−0.48 (17)
C3—C4—C5—C6	177.57 (18)	C8—C7—S1—C4	178.84 (17)
S1—C4—C5—C6	0.9 (2)	C5—C4—S1—C7	−0.28 (16)
C4—C5—C6—C7	−1.4 (3)	C3—C4—S1—C7	−177.16 (16)
C5—C6—C7—C8	−178.1 (2)