(E)-3-(2,3,4,5,6-Penta-fluoro-styr-yl)thio-phene.

The reaction of thio-phene-3-carboxaldehyde and perfluoro-benzyl-triphenyl-phospho-nium bromide in the presence of sodium hydride gave the title compound, C(12)H(5)F(5)S, in 70% yield. The thiophene and perfluorophenyl groups form a dihedral angle of 5.4 (2)°. The structure is characterized by a head-to-tail organization in a columnar arrangement due to π-π inter-actions between the thio-phene and penta-fluoro-phenyl rings with centroid-centroid distances in the range 3.698 (2)-3.802 (2) Å.

Related literature

For electronic materials with high conductivity due to complementary groups, see: Yamamoto et al. (2009 ▶); Hoeben et al. (2005 ▶). For a bottom-up approach to rational design of electronic materials, see: Lu & Lieber (2007 ▶). For thio­phene derivatives used in solar cells or oLEDs, see: Osaka & McCullough (2008 ▶); Mishra et al. (2009 ▶). For the structure of 2,5-dibromo-3-(2,3,4,5,6-penta­fluoro­styr­yl)thio­phene, see: Clément et al. (2010 ▶).

Experimental

Crystal data

C12H5F5S

M = 276.22

Monoclinic,

a = 5.8097 (15) Å

b = 24.581 (6) Å

c = 7.3224 (18) Å

β = 94.953 (4)°

V = 1041.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 100 K

0.31 × 0.21 × 0.05 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.637, T max = 0.746

5781 measured reflections

3056 independent reflections

2513 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.086

wR(F 2) = 0.186

S = 1.21

3056 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.58 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); 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 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009992/sj2740sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009992/sj2740Isup2.hkl

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

C12H5F5S	F(000) = 552
Mr = 276.22	Dx = 1.761 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2814 reflections
a = 5.8097 (15) Å	θ = 2.9–31.1°
b = 24.581 (6) Å	µ = 0.36 mm−1
c = 7.3224 (18) Å	T = 100 K
β = 94.953 (4)°	Plate, colourless
V = 1041.8 (4) Å3	0.31 × 0.21 × 0.05 mm
Z = 4

Bruker SMART APEX area-detector diffractometer	3056 independent reflections
Radiation source: fine-focus sealed tube	2513 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 31.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −5→8
Tmin = 0.637, Tmax = 0.746	k = −25→35
5781 measured reflections	l = −10→8

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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186	H-atom parameters constrained
S = 1.21	w = 1/[σ2(Fo2) + (0.0193P)2 + 5.9694P] where P = (Fo2 + 2Fc2)/3
3056 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.58 e Å−3
3 constraints

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.22542 (18)	0.54717 (4)	0.56342 (15)	0.0219 (2)
F9	−0.0433 (4)	0.80297 (10)	0.4285 (3)	0.0200 (5)
F10	−0.0888 (4)	0.91035 (10)	0.4229 (3)	0.0211 (5)
F12	0.6511 (4)	0.93050 (10)	0.7310 (3)	0.0218 (5)
F13	0.6987 (4)	0.82233 (10)	0.7475 (3)	0.0205 (5)
F11	0.2579 (5)	0.97589 (10)	0.5694 (4)	0.0244 (5)
C4	0.4895 (7)	0.62804 (17)	0.6462 (5)	0.0181 (7)
H4	0.6168	0.6489	0.6883	0.022*
C13	0.5023 (6)	0.84305 (17)	0.6626 (5)	0.0160 (7)
C3	0.2770 (6)	0.65098 (16)	0.5703 (5)	0.0154 (7)
C8	0.3328 (6)	0.80732 (16)	0.5885 (5)	0.0154 (7)
C12	0.4805 (6)	0.89877 (16)	0.6571 (5)	0.0162 (7)
C11	0.2808 (7)	0.92176 (16)	0.5756 (5)	0.0188 (8)
C9	0.1336 (7)	0.83262 (16)	0.5062 (5)	0.0161 (7)
C6	0.2239 (7)	0.70861 (16)	0.5483 (5)	0.0183 (7)
H6	0.0793	0.7182	0.4934	0.022*
C10	0.1082 (7)	0.88846 (17)	0.5015 (5)	0.0185 (8)
C7	0.3708 (7)	0.74870 (16)	0.6022 (5)	0.0178 (7)
H7	0.5149	0.7378	0.6548	0.021*
C2	0.1186 (7)	0.61079 (17)	0.5195 (5)	0.0179 (7)
H2	−0.0301	0.6177	0.4670	0.022*
C5	0.4880 (7)	0.57227 (17)	0.6512 (5)	0.0177 (7)
H5	0.6123	0.5509	0.6961	0.021*

	U11	U22	U33	U12	U13	U23
S1	0.0228 (5)	0.0195 (5)	0.0229 (5)	−0.0009 (4)	−0.0003 (4)	−0.0008 (4)
F9	0.0164 (11)	0.0213 (12)	0.0216 (12)	−0.0008 (9)	−0.0019 (9)	−0.0022 (9)
F10	0.0163 (11)	0.0242 (13)	0.0219 (12)	0.0053 (9)	−0.0039 (9)	0.0004 (10)
F12	0.0203 (11)	0.0239 (13)	0.0210 (12)	−0.0070 (10)	−0.0004 (9)	−0.0039 (10)
F13	0.0150 (10)	0.0257 (13)	0.0199 (12)	0.0008 (9)	−0.0033 (9)	−0.0005 (9)
F11	0.0309 (13)	0.0179 (12)	0.0240 (13)	0.0007 (10)	0.0003 (10)	−0.0014 (10)
C4	0.0169 (16)	0.0215 (19)	0.0159 (16)	−0.0013 (14)	0.0018 (13)	−0.0014 (15)
C13	0.0131 (15)	0.024 (2)	0.0107 (15)	0.0005 (14)	0.0010 (12)	0.0007 (14)
C3	0.0158 (16)	0.0196 (19)	0.0107 (15)	0.0011 (13)	0.0010 (13)	−0.0002 (13)
C8	0.0136 (16)	0.0198 (19)	0.0133 (16)	0.0009 (13)	0.0035 (13)	0.0000 (14)
C12	0.0150 (16)	0.0206 (19)	0.0129 (16)	−0.0048 (14)	0.0013 (13)	−0.0023 (14)
C11	0.026 (2)	0.0166 (19)	0.0137 (17)	0.0001 (15)	0.0035 (15)	−0.0014 (14)
C9	0.0158 (16)	0.0185 (19)	0.0141 (16)	−0.0014 (14)	0.0013 (13)	0.0011 (14)
C6	0.0206 (17)	0.0199 (19)	0.0148 (17)	0.0032 (15)	0.0028 (13)	0.0011 (14)
C10	0.0163 (17)	0.023 (2)	0.0170 (17)	0.0047 (14)	0.0036 (14)	0.0018 (15)
C7	0.0201 (17)	0.0189 (19)	0.0144 (16)	0.0018 (14)	0.0010 (14)	−0.0002 (14)
C2	0.0156 (17)	0.022 (2)	0.0152 (16)	−0.0009 (14)	−0.0018 (13)	−0.0003 (14)
C5	0.0170 (17)	0.022 (2)	0.0133 (16)	0.0035 (14)	−0.0020 (13)	−0.0002 (14)

S1—C2	1.703 (4)	C3—C2	1.380 (5)
S1—C5	1.718 (4)	C3—C6	1.456 (5)
F9—C9	1.345 (4)	C8—C9	1.403 (5)
F10—C10	1.348 (4)	C8—C7	1.460 (5)
F12—C12	1.338 (4)	C12—C11	1.379 (6)
F13—C13	1.350 (4)	C11—C10	1.370 (6)
F11—C11	1.338 (5)	C9—C10	1.381 (6)
C4—C5	1.371 (6)	C6—C7	1.341 (6)
C4—C3	1.425 (5)	C6—H6	0.9300
C4—H4	0.9300	C7—H7	0.9300
C13—C12	1.376 (6)	C2—H2	0.9300
C13—C8	1.394 (5)	C5—H5	0.9300
S1···S1i	3.5611 (17)	F10···H5iii	2.49
F9···F13ii	2.921 (3)	H5···F11iv	2.59
F10···F12ii	2.865 (3)	H2···F13iii	2.61
F10···C12ii	3.166 (4)	C3···C9v	3.392 (5)
F10···C5iii	3.056 (5)	C3···C13vi	3.365 (5)
C2—S1—C5	92.19 (19)	F9—C9—C10	116.9 (3)
C5—C4—C3	113.5 (4)	F9—C9—C8	120.9 (3)
C5—C4—H4	123.3	C10—C9—C8	122.3 (4)
C3—C4—H4	123.3	C7—C6—C3	124.0 (4)
F13—C13—C12	117.4 (3)	C7—C6—H6	118.0
F13—C13—C8	118.8 (4)	C3—C6—H6	118.0
C12—C13—C8	123.7 (4)	F10—C10—C11	119.8 (4)
C2—C3—C4	110.9 (4)	F10—C10—C9	119.5 (4)
C2—C3—C6	122.5 (4)	C11—C10—C9	120.7 (4)
C4—C3—C6	126.6 (4)	C6—C7—C8	128.1 (4)
C13—C8—C9	114.6 (4)	C6—C7—H7	116.0
C13—C8—C7	119.8 (3)	C8—C7—H7	116.0
C9—C8—C7	125.5 (4)	C3—C2—S1	112.5 (3)
F12—C12—C13	120.3 (3)	C3—C2—H2	123.7
F12—C12—C11	120.2 (4)	S1—C2—H2	123.7
C13—C12—C11	119.5 (4)	C4—C5—S1	110.9 (3)
F11—C11—C10	120.9 (4)	C4—C5—H5	124.6
F11—C11—C12	120.0 (4)	S1—C5—H5	124.6
C10—C11—C12	119.1 (4)
C5—C4—C3—C2	0.0 (5)	C2—C3—C6—C7	177.5 (4)
C5—C4—C3—C6	179.3 (4)	C4—C3—C6—C7	−1.7 (6)
F13—C13—C8—C9	178.9 (3)	F11—C11—C10—F10	−0.7 (6)
C12—C13—C8—C9	−0.1 (6)	C12—C11—C10—F10	179.4 (3)
F13—C13—C8—C7	−0.6 (5)	F11—C11—C10—C9	179.2 (4)
C12—C13—C8—C7	−179.6 (4)	C12—C11—C10—C9	−0.6 (6)
F13—C13—C12—F12	1.1 (5)	F9—C9—C10—F10	0.7 (5)
C8—C13—C12—F12	−179.9 (3)	C8—C9—C10—F10	−179.0 (3)
F13—C13—C12—C11	−178.5 (3)	F9—C9—C10—C11	−179.3 (3)
C8—C13—C12—C11	0.5 (6)	C8—C9—C10—C11	1.1 (6)
F12—C12—C11—F11	0.4 (6)	C3—C6—C7—C8	−179.1 (4)
C13—C12—C11—F11	−180.0 (4)	C13—C8—C7—C6	176.1 (4)
F12—C12—C11—C10	−179.7 (4)	C9—C8—C7—C6	−3.3 (7)
C13—C12—C11—C10	−0.1 (6)	C4—C3—C2—S1	0.1 (4)
C13—C8—C9—F9	179.7 (3)	C6—C3—C2—S1	−179.2 (3)
C7—C8—C9—F9	−0.9 (6)	C5—S1—C2—C3	−0.2 (3)
C13—C8—C9—C10	−0.7 (6)	C3—C4—C5—S1	−0.2 (4)
C7—C8—C9—C10	178.8 (4)	C2—S1—C5—C4	0.2 (3)