3,5-Dibromo-2-[2,5-dibut-oxy-4-(3,5-dibromo-thio-phen-2-yl)phen-yl]thio-phene.

The title mol-ecule, C(22)H(22)Br(4)O(2)S(2), is centrosymmetric with an inversion centre located at the centre of the benzene ring. The 3,5-dibromo-thio-phene groups are twisted relative to the benzene ring, making a dihedral angle of 41.43 (9)°.

Related literature

The title compound belongs to the family of aryl­thio­phenes, compounds frequently used as electroluminescent oligomers to produce polymers for LED applications. For a related structure and background references, see: Promarak & Ruchirawat (2007 ▶); Huang et al. (2007 ▶). For related structures, see: Li et al. (2008 ▶); Kuriger et al. (2008 ▶); Ali et al. (2008 ▶).

Experimental

Crystal data

C22H22Br4O2S2

M = 702.16

Monoclinic,

a = 13.0156 (3) Å

b = 7.8157 (2) Å

c = 12.2264 (2) Å

β = 101.027 (2)°

V = 1220.78 (5) Å3

Z = 2

Cu Kα radiation

μ = 9.79 mm−1

T = 150 K

0.24 × 0.10 × 0.07 mm

Data collection

Oxford Diffraction Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.202, T max = 0.547

12067 measured reflections

2349 independent reflections

2272 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.084

S = 1.10

2349 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.98 e Å−3

Δρmin = −0.54 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; 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/S1600536811045235/gk2422sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045235/gk2422Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045235/gk2422Isup3.cml

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

C22H22Br4O2S2	F(000) = 684
Mr = 702.16	Dx = 1.910 Mg m−3
Monoclinic, P21/c	Melting point = 417–419 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 13.0156 (3) Å	Cell parameters from 7985 reflections
b = 7.8157 (2) Å	θ = 3–71°
c = 12.2264 (2) Å	µ = 9.79 mm−1
β = 101.027 (2)°	T = 150 K
V = 1220.78 (5) Å3	Prismatic, yellow
Z = 2	0.24 × 0.10 × 0.07 mm

Oxford Diffraction Gemini diffractometer	2349 independent reflections
Radiation source: fine-focus sealed tube	2272 reflections with I > 2σ(I)
graphite	Rint = 0.037
ω/2θ scans	θmax = 71.0°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	h = −15→15
Tmin = 0.202, Tmax = 0.547	k = −9→9
12067 measured reflections	l = −14→14

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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0574P)2 + 0.8587P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
2349 reflections	Δρmax = 0.98 e Å−3
138 parameters	Δρmin = −0.54 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0057 (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
Br1	0.85564 (2)	0.22645 (4)	0.97981 (2)	0.02292 (14)
Br2	0.43160 (2)	0.45620 (4)	0.82956 (2)	0.01904 (14)
S1	0.74092 (5)	0.36060 (9)	0.74910 (5)	0.01532 (18)
O1	0.70059 (14)	0.6197 (2)	0.57663 (15)	0.0142 (4)
C1	0.60951 (19)	0.4183 (3)	0.7216 (2)	0.0119 (5)
C2	0.56937 (19)	0.3982 (3)	0.8164 (2)	0.0122 (5)
C3	0.6403 (2)	0.3333 (3)	0.9103 (2)	0.0143 (5)
H3	0.6239	0.3128	0.9799	0.017*
C4	0.7353 (2)	0.3055 (3)	0.8837 (2)	0.0143 (5)
C5	0.5550 (2)	0.4615 (3)	0.6079 (2)	0.0115 (5)
C6	0.6011 (2)	0.5643 (3)	0.5364 (2)	0.0113 (5)
C7	0.4545 (2)	0.3963 (3)	0.5690 (2)	0.0125 (5)
H7	0.4243	0.3250	0.6150	0.015*
C8	0.7491 (2)	0.7284 (3)	0.5067 (2)	0.0158 (5)
H8A	0.7077	0.8311	0.4876	0.019*
H8B	0.7549	0.6692	0.4384	0.019*
C9	0.8561 (2)	0.7736 (4)	0.5713 (3)	0.0193 (6)
H9A	0.8917	0.8437	0.5247	0.023*
H9B	0.8963	0.6692	0.5884	0.023*
C10	0.8543 (2)	0.8692 (4)	0.6796 (3)	0.0278 (7)
H10A	0.8147	0.9742	0.6627	0.033*
H10B	0.8186	0.7995	0.7264	0.033*
C11	0.9630 (3)	0.9124 (5)	0.7433 (4)	0.0411 (9)
H11A	1.0016	0.8086	0.7632	0.062*
H11B	0.9574	0.9744	0.8097	0.062*
H11C	0.9987	0.9813	0.6974	0.062*

	U11	U22	U33	U12	U13	U23
Br1	0.0157 (2)	0.0312 (2)	0.0196 (2)	0.00459 (11)	−0.00230 (13)	0.00655 (11)
Br2	0.01321 (19)	0.0258 (2)	0.0200 (2)	0.00462 (10)	0.00798 (13)	0.00194 (10)
S1	0.0078 (3)	0.0252 (4)	0.0130 (3)	0.0008 (2)	0.0021 (2)	0.0026 (2)
O1	0.0071 (8)	0.0178 (9)	0.0168 (9)	−0.0044 (7)	−0.0001 (7)	0.0041 (7)
C1	0.0075 (11)	0.0121 (11)	0.0160 (13)	−0.0016 (9)	0.0024 (10)	0.0002 (10)
C2	0.0096 (12)	0.0118 (11)	0.0157 (12)	−0.0010 (9)	0.0037 (9)	−0.0015 (10)
C3	0.0155 (13)	0.0152 (13)	0.0130 (12)	0.0008 (10)	0.0045 (10)	0.0012 (10)
C4	0.0131 (13)	0.0151 (12)	0.0133 (12)	0.0009 (10)	−0.0010 (10)	0.0026 (10)
C5	0.0097 (12)	0.0128 (12)	0.0124 (12)	0.0005 (9)	0.0034 (10)	0.0003 (9)
C6	0.0078 (12)	0.0104 (12)	0.0160 (12)	−0.0019 (9)	0.0032 (10)	−0.0024 (9)
C7	0.0099 (12)	0.0130 (12)	0.0157 (12)	−0.0018 (10)	0.0048 (9)	0.0023 (9)
C8	0.0102 (13)	0.0181 (13)	0.0193 (13)	−0.0037 (10)	0.0036 (11)	0.0050 (10)
C9	0.0080 (13)	0.0205 (14)	0.0289 (15)	−0.0028 (10)	0.0025 (11)	0.0040 (11)
C10	0.0136 (15)	0.0281 (16)	0.0406 (19)	−0.0038 (11)	0.0021 (13)	−0.0073 (13)
C11	0.0219 (17)	0.039 (2)	0.057 (2)	−0.0070 (15)	−0.0077 (16)	−0.0178 (18)

Br1—C4	1.874 (3)	C7—C6i	1.387 (4)
Br2—C2	1.886 (3)	C7—H7	0.9300
S1—C4	1.716 (3)	C8—C9	1.506 (4)
S1—C1	1.738 (3)	C8—H8A	0.9700
O1—C6	1.365 (3)	C8—H8B	0.9700
O1—C8	1.434 (3)	C9—C10	1.524 (4)
C1—C2	1.368 (4)	C9—H9A	0.9700
C1—C5	1.474 (4)	C9—H9B	0.9700
C2—C3	1.422 (4)	C10—C11	1.517 (4)
C3—C4	1.355 (4)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
C5—C7	1.400 (4)	C11—H11A	0.9600
C5—C6	1.404 (4)	C11—H11B	0.9600
C6—C7i	1.387 (4)	C11—H11C	0.9600
C4—S1—C1	91.70 (13)	O1—C8—H8A	110.3
C6—O1—C8	117.94 (19)	C9—C8—H8A	110.3
C2—C1—C5	129.2 (2)	O1—C8—H8B	110.3
C2—C1—S1	109.12 (19)	C9—C8—H8B	110.3
C5—C1—S1	121.31 (19)	H8A—C8—H8B	108.5
C1—C2—C3	115.5 (2)	C8—C9—C10	113.8 (2)
C1—C2—Br2	124.6 (2)	C8—C9—H9A	108.8
C3—C2—Br2	119.89 (19)	C10—C9—H9A	108.8
C4—C3—C2	110.2 (2)	C8—C9—H9B	108.8
C4—C3—H3	124.9	C10—C9—H9B	108.8
C2—C3—H3	124.9	H9A—C9—H9B	107.7
C3—C4—S1	113.4 (2)	C11—C10—C9	112.8 (3)
C3—C4—Br1	126.5 (2)	C11—C10—H10A	109.0
S1—C4—Br1	120.03 (15)	C9—C10—H10A	109.0
C7—C5—C6	118.7 (2)	C11—C10—H10B	109.0
C7—C5—C1	119.1 (2)	C9—C10—H10B	109.0
C6—C5—C1	122.2 (2)	H10A—C10—H10B	107.8
O1—C6—C7i	123.7 (2)	C10—C11—H11A	109.5
O1—C6—C5	116.5 (2)	C10—C11—H11B	109.5
C7i—C6—C5	119.8 (2)	H11A—C11—H11B	109.5
C6i—C7—C5	121.5 (2)	C10—C11—H11C	109.5
C6i—C7—H7	119.2	H11A—C11—H11C	109.5
C5—C7—H7	119.2	H11B—C11—H11C	109.5
O1—C8—C9	107.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Br2	0.93	2.80	3.289 (2)	114