1,4-Dimeth-oxy-2,5-bis-{2-[4-(trifluoro-meth-yl)phen-yl]ethyn-yl}benzene.

The asymmetric unit of the title compound, C(26)H(16)F(6)O(2), contains one half of the mol-ecule situated on an inversion centre. In the rod-like mol-ecule, the two terminal benzene rings form a dihedral angle of 71.9 (1)° with the central benzene ring. The trifluoro-methyl group is rotationally disordered over two orientations in a 0.53 (1):0.47 (1) ratio. The crystal packing exhibits no classical inter-molecular inter-actions.

Related literature

For applications and details of the synthesis of (aryl­ene)­ethynylene derivatives, see: Dirk et al. (2001 ▶); Miljanić et al. (2005 ▶); Morin et al. (2007 ▶). For the crystal structure of a related 1,4-bis­(p-tolyl­ethyn­yl)benzene, see: Filatov & Petrukhina (2005 ▶).

Experimental

Crystal data

C26H16F6O2

M = 474.39

Monoclinic,

a = 11.1473 (4) Å

b = 13.0795 (6) Å

c = 7.5875 (4) Å

β = 97.467 (3)°

V = 1096.88 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.22 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.973, T max = 0.977

9899 measured reflections

2484 independent reflections

1753 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.04

2484 reflections

184 parameters

30 restraints

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.21 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681102099X/cv5093sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102099X/cv5093Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681102099X/cv5093Isup3.cml

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

C26H16F6O2	F(000) = 484
Mr = 474.39	Dx = 1.436 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.1473 (4) Å	θ = 2.4–27.4°
b = 13.0795 (6) Å	µ = 0.13 mm−1
c = 7.5875 (4) Å	T = 293 K
β = 97.467 (3)°	Block, colourless
V = 1096.88 (9) Å3	0.22 × 0.20 × 0.19 mm
Z = 2

Bruker APEXII CCD diffractometer	2484 independent reflections
Radiation source: fine-focus sealed tube	1753 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 27.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −14→14
Tmin = 0.973, Tmax = 0.977	k = −15→16
9899 measured reflections	l = −9→9

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0488P)2 + 0.235P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2484 reflections	Δρmax = 0.16 e Å−3
184 parameters	Δρmin = −0.21 e Å−3
30 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: 0.011 (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	Occ. (<1)
C1	0.75647 (18)	0.83209 (17)	0.5592 (3)	0.0718 (6)
C2	0.63855 (14)	0.85402 (14)	0.6275 (2)	0.0527 (4)
C3	0.54917 (16)	0.78099 (15)	0.6153 (3)	0.0588 (5)
H3	0.5617	0.7178	0.5647	0.071*
C4	0.44076 (15)	0.80134 (14)	0.6781 (2)	0.0562 (5)
H4	0.3805	0.7518	0.6697	0.067*
C5	0.42165 (13)	0.89548 (14)	0.7537 (2)	0.0473 (4)
C6	0.51220 (16)	0.96868 (14)	0.7635 (3)	0.0589 (5)
H6	0.4999	1.0322	0.8131	0.071*
C7	0.62038 (16)	0.94824 (15)	0.7003 (3)	0.0608 (5)
H7	0.6806	0.9978	0.7069	0.073*
C8	0.31058 (14)	0.91755 (14)	0.8243 (2)	0.0525 (4)
C9	0.22045 (14)	0.93931 (13)	0.8846 (2)	0.0497 (4)
C10	0.10877 (13)	0.96910 (12)	0.9454 (2)	0.0452 (4)
C11	0.03456 (14)	1.03921 (12)	0.8455 (2)	0.0477 (4)
H11	0.0584	1.0656	0.7417	0.057*
C12	0.07381 (13)	0.92971 (12)	1.1021 (2)	0.0455 (4)
C13	0.1199 (2)	0.82346 (18)	1.3576 (3)	0.0769 (6)
H13A	0.1109	0.8791	1.4372	0.115*
H13B	0.1823	0.7782	1.4105	0.115*
H13C	0.0449	0.7867	1.3348	0.115*
O1	0.15207 (10)	0.86246 (10)	1.19450 (17)	0.0605 (4)
F1	0.7461 (6)	0.8553 (4)	0.3877 (5)	0.0928 (16)	0.530 (10)
F2	0.8484 (5)	0.8832 (9)	0.6296 (14)	0.183 (5)	0.530 (10)
F3	0.7807 (6)	0.7351 (3)	0.5523 (9)	0.125 (3)	0.530 (10)
F1'	0.7695 (6)	0.7396 (4)	0.5079 (11)	0.136 (4)	0.470 (10)
F2'	0.8458 (4)	0.8398 (6)	0.6905 (7)	0.0953 (18)	0.470 (10)
F3'	0.7830 (9)	0.8979 (10)	0.4453 (17)	0.205 (6)	0.470 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0550 (12)	0.0973 (17)	0.0678 (14)	0.0107 (11)	0.0252 (10)	−0.0029 (13)
C2	0.0413 (8)	0.0727 (12)	0.0462 (9)	0.0070 (8)	0.0135 (7)	−0.0022 (8)
C3	0.0545 (10)	0.0638 (12)	0.0603 (11)	0.0052 (8)	0.0152 (8)	−0.0127 (9)
C4	0.0465 (9)	0.0623 (11)	0.0613 (11)	−0.0033 (8)	0.0128 (8)	−0.0070 (9)
C5	0.0374 (8)	0.0606 (10)	0.0454 (9)	0.0062 (7)	0.0118 (7)	0.0025 (8)
C6	0.0543 (10)	0.0562 (11)	0.0703 (12)	0.0008 (8)	0.0239 (9)	−0.0095 (9)
C7	0.0468 (9)	0.0697 (12)	0.0696 (12)	−0.0083 (8)	0.0213 (9)	−0.0073 (10)
C8	0.0438 (9)	0.0616 (11)	0.0542 (10)	0.0045 (8)	0.0146 (7)	0.0039 (8)
C9	0.0409 (8)	0.0552 (10)	0.0552 (10)	0.0014 (7)	0.0142 (7)	0.0028 (8)
C10	0.0354 (7)	0.0494 (9)	0.0531 (9)	−0.0011 (7)	0.0144 (7)	−0.0027 (7)
C11	0.0422 (8)	0.0532 (10)	0.0503 (9)	−0.0016 (7)	0.0162 (7)	0.0039 (8)
C12	0.0379 (8)	0.0464 (9)	0.0532 (10)	0.0014 (6)	0.0099 (7)	0.0029 (7)
C13	0.0759 (13)	0.0846 (15)	0.0732 (14)	0.0208 (11)	0.0207 (11)	0.0317 (12)
O1	0.0510 (7)	0.0679 (8)	0.0653 (8)	0.0144 (6)	0.0170 (6)	0.0167 (6)
F1	0.089 (3)	0.120 (3)	0.081 (2)	0.005 (2)	0.0551 (18)	0.006 (2)
F2	0.056 (3)	0.278 (10)	0.228 (8)	−0.065 (5)	0.068 (4)	−0.175 (8)
F3	0.119 (4)	0.109 (4)	0.168 (5)	0.074 (3)	0.095 (4)	0.067 (4)
F1'	0.071 (3)	0.180 (8)	0.163 (5)	0.005 (3)	0.031 (3)	−0.118 (6)
F2'	0.0321 (19)	0.142 (4)	0.115 (3)	0.0013 (19)	0.0200 (17)	0.000 (3)
F3'	0.142 (8)	0.247 (10)	0.260 (10)	0.105 (7)	0.157 (8)	0.190 (9)

C1—F2	1.281 (4)	C6—C7	1.380 (2)
C1—F3'	1.281 (4)	C6—H6	0.9300
C1—F1'	1.285 (4)	C7—H7	0.9300
C1—F3	1.300 (4)	C8—C9	1.191 (2)
C1—F2'	1.318 (4)	C9—C10	1.437 (2)
C1—F1	1.327 (4)	C10—C11	1.391 (2)
C1—C2	1.502 (2)	C10—C12	1.397 (2)
C2—C3	1.375 (3)	C11—C12i	1.381 (2)
C2—C7	1.376 (3)	C11—H11	0.9300
C3—C4	1.381 (2)	C12—O1	1.3664 (19)
C3—H3	0.9300	C12—C11i	1.381 (2)
C4—C5	1.386 (2)	C13—O1	1.427 (2)
C4—H4	0.9300	C13—H13A	0.9600
C5—C6	1.386 (2)	C13—H13B	0.9600
C5—C8	1.441 (2)	C13—H13C	0.9600
F2—C1—F3'	71.9 (5)	C5—C4—H4	119.9
F2—C1—F1'	120.1 (5)	C6—C5—C4	119.06 (14)
F3'—C1—F1'	112.5 (6)	C6—C5—C8	119.78 (16)
F2—C1—F3	111.5 (5)	C4—C5—C8	121.15 (16)
F3'—C1—F3	124.1 (6)	C7—C6—C5	120.70 (17)
F1'—C1—F3	15.5 (5)	C7—C6—H6	119.6
F2—C1—F2'	32.8 (6)	C5—C6—H6	119.6
F3'—C1—F2'	103.9 (7)	C2—C7—C6	119.57 (17)
F1'—C1—F2'	101.3 (4)	C2—C7—H7	120.2
F3—C1—F2'	87.9 (5)	C6—C7—H7	120.2
F2—C1—F1	104.7 (6)	C9—C8—C5	177.5 (2)
F3'—C1—F1	35.2 (8)	C8—C9—C10	175.89 (19)
F1'—C1—F1	85.2 (4)	C11—C10—C12	119.64 (13)
F3—C1—F1	100.1 (4)	C11—C10—C9	118.86 (14)
F2'—C1—F1	133.2 (3)	C12—C10—C9	121.50 (15)
F2—C1—C2	116.4 (3)	C12i—C11—C10	121.18 (15)
F3'—C1—C2	113.2 (3)	C12i—C11—H11	119.4
F1'—C1—C2	115.0 (4)	C10—C11—H11	119.4
F3—C1—C2	113.4 (3)	O1—C12—C11i	124.45 (15)
F2'—C1—C2	109.5 (3)	O1—C12—C10	116.37 (13)
F1—C1—C2	109.1 (3)	C11i—C12—C10	119.18 (15)
C3—C2—C7	120.41 (15)	O1—C13—H13A	109.5
C3—C2—C1	120.20 (17)	O1—C13—H13B	109.5
C7—C2—C1	119.38 (17)	H13A—C13—H13B	109.5
C2—C3—C4	120.11 (17)	O1—C13—H13C	109.5
C2—C3—H3	119.9	H13A—C13—H13C	109.5
C4—C3—H3	119.9	H13B—C13—H13C	109.5
C3—C4—C5	120.14 (17)	C12—O1—C13	117.37 (13)
C3—C4—H4	119.9
F2—C1—C2—C3	−154.8 (8)	C8—C5—C6—C7	178.50 (18)
F3'—C1—C2—C3	124.7 (9)	C3—C2—C7—C6	0.9 (3)
F1'—C1—C2—C3	−6.6 (5)	C1—C2—C7—C6	−179.94 (18)
F3—C1—C2—C3	−23.5 (4)	C5—C6—C7—C2	−0.3 (3)
F2'—C1—C2—C3	−119.9 (4)	C6—C5—C8—C9	−1(5)
F1—C1—C2—C3	87.1 (3)	C4—C5—C8—C9	178 (100)
F2—C1—C2—C7	26.0 (8)	C5—C8—C9—C10	85 (5)
F3'—C1—C2—C7	−54.5 (10)	C8—C9—C10—C11	−11 (3)
F1'—C1—C2—C7	174.2 (5)	C8—C9—C10—C12	169 (3)
F3—C1—C2—C7	157.3 (4)	C12—C10—C11—C12i	−0.4 (3)
F2'—C1—C2—C7	60.9 (4)	C9—C10—C11—C12i	179.90 (16)
F1—C1—C2—C7	−92.1 (3)	C11—C10—C12—O1	−179.04 (15)
C7—C2—C3—C4	−0.8 (3)	C9—C10—C12—O1	0.6 (2)
C1—C2—C3—C4	−179.95 (18)	C11—C10—C12—C11i	0.4 (3)
C2—C3—C4—C5	0.0 (3)	C9—C10—C12—C11i	−179.92 (16)
C3—C4—C5—C6	0.6 (3)	C11i—C12—O1—C13	−1.1 (3)
C3—C4—C5—C8	−178.37 (17)	C10—C12—O1—C13	178.26 (17)
C4—C5—C6—C7	−0.5 (3)