(1E,3E)-1,4-Bis(4-meth-oxy-phen-yl)buta-1,3-diene.

The title compound, C(18)H(18)O(2), which exhibits blue emission in the solid state, is an inter-mediate in the preparation of liquid crystals and polymers. The mol-ecule is located on an inversion centre. In the crystal, mol-ecules are arranged in a herringbone motif.

Related literature

For related structures, see: George et al. (1998 ▶); Vishnumurthy et al. (2002 ▶); Davis et al. (2004 ▶, 2008 ▶); Kumar et al. (2009 ▶); Ono et al. (2009 ▶). For the synthesis and the use of the title compound in the preparation of polymers and chiral liquid crystals, see: Rotarski (1908 ▶); Wang et al. (2003 ▶); Das et al. (2008 ▶). For mol­ecules with a herringbone arrangement, see: Koren et al. (2003 ▶).

Experimental

Crystal data

C18H18O2

M = 266.32

Orthorhombic,

a = 7.3543 (3) Å

b = 6.2617 (3) Å

c = 31.3872 (13) Å

V = 1445.39 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.25 × 0.22 × 0.22 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer

Absorption correction: numerical (SADABS; Sheldrick, 2006 ▶) T min = 0.981, T max = 0.983

40427 measured reflections

1658 independent reflections

1287 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.110

S = 1.08

1658 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S1600536810037141/is2575sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037141/is2575Isup2.hkl

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

C18H18O2	F(000) = 568
Mr = 266.32	Dx = 1.224 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7512 reflections
a = 7.3543 (3) Å	θ = 2.6–23.6°
b = 6.2617 (3) Å	µ = 0.08 mm−1
c = 31.3872 (13) Å	T = 293 K
V = 1445.39 (11) Å3	Pyramidal, colourless
Z = 4	0.25 × 0.22 × 0.22 mm

Bruker X8 APEXII CCD area-detector diffractometer	1658 independent reflections
Radiation source: fine-focus sealed tube	1287 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 27.5°, θmin = 1.3°
Absorption correction: numerical (SADABS; Sheldrick, 2006)	h = −8→9
Tmin = 0.981, Tmax = 0.983	k = −8→8
40427 measured reflections	l = −40→37

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0429P)2 + 0.3178P] where P = (Fo2 + 2Fc2)/3
1658 reflections	(Δ/σ)max < 0.001
92 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

Experimental. 2010–02-01 # Formatted by publCIF

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
O1	−0.01884 (15)	0.42509 (16)	0.19955 (3)	0.0584 (3)
C1	−0.00667 (17)	0.4944 (2)	0.15818 (4)	0.0420 (3)
C2	0.07908 (18)	0.3855 (2)	0.12580 (4)	0.0458 (3)
H2	0.1341	0.2543	0.1310	0.055*
C3	0.08211 (18)	0.4740 (2)	0.08547 (4)	0.0441 (3)
H3	0.1386	0.3988	0.0636	0.053*
C4	0.00422 (16)	0.6707 (2)	0.07623 (4)	0.0396 (3)
C5	−0.08465 (17)	0.7752 (2)	0.10963 (4)	0.0440 (3)
H5	−0.1411	0.9056	0.1046	0.053*
C6	−0.09002 (18)	0.6884 (2)	0.14980 (4)	0.0455 (3)
H6	−0.1501	0.7605	0.1716	0.055*
C7	0.02594 (18)	0.7620 (2)	0.03382 (4)	0.0452 (3)
H7	0.0769	0.6729	0.0133	0.054*
C8	−0.01863 (18)	0.9584 (2)	0.02086 (4)	0.0461 (3)
H8	−0.0777	1.0472	0.0402	0.055*
C9	0.0738 (3)	0.2339 (3)	0.21039 (5)	0.0789 (6)
H9A	0.0254	0.1176	0.1940	0.118*
H9B	0.0577	0.2050	0.2402	0.118*
H9C	0.2010	0.2497	0.2043	0.118*

	U11	U22	U33	U12	U13	U23
O1	0.0773 (7)	0.0568 (6)	0.0410 (6)	0.0056 (6)	0.0018 (5)	0.0061 (5)
C1	0.0447 (7)	0.0442 (7)	0.0371 (7)	−0.0047 (6)	−0.0013 (5)	0.0012 (6)
C2	0.0485 (8)	0.0395 (7)	0.0495 (8)	0.0068 (6)	0.0004 (6)	0.0015 (6)
C3	0.0454 (7)	0.0431 (7)	0.0439 (7)	0.0041 (6)	0.0049 (6)	−0.0034 (6)
C4	0.0366 (6)	0.0405 (7)	0.0416 (7)	−0.0029 (5)	−0.0018 (5)	−0.0007 (5)
C5	0.0446 (7)	0.0395 (7)	0.0479 (8)	0.0056 (6)	0.0001 (6)	−0.0005 (6)
C6	0.0485 (8)	0.0439 (7)	0.0441 (7)	0.0043 (6)	0.0036 (6)	−0.0047 (6)
C7	0.0464 (7)	0.0484 (8)	0.0407 (7)	−0.0010 (6)	−0.0012 (6)	−0.0009 (6)
C8	0.0463 (7)	0.0488 (8)	0.0430 (7)	−0.0031 (6)	−0.0036 (6)	0.0015 (6)
C9	0.1102 (16)	0.0692 (11)	0.0574 (10)	0.0158 (11)	−0.0010 (10)	0.0204 (9)

O1—C1	1.3721 (15)	C5—C6	1.3735 (18)
O1—C9	1.4190 (19)	C5—H5	0.9300
C1—C2	1.3768 (18)	C6—H6	0.9300
C1—C6	1.3860 (18)	C7—C8	1.3367 (19)
C2—C3	1.3820 (18)	C7—H7	0.9300
C2—H2	0.9300	C8—C8i	1.435 (3)
C3—C4	1.3890 (18)	C8—H8	0.9300
C3—H3	0.9300	C9—H9A	0.9600
C4—C5	1.3978 (18)	C9—H9B	0.9600
C4—C7	1.4573 (18)	C9—H9C	0.9600
C1—O1—C9	117.55 (12)	C5—C6—C1	120.54 (12)
O1—C1—C2	124.87 (12)	C5—C6—H6	119.7
O1—C1—C6	115.34 (12)	C1—C6—H6	119.7
C2—C1—C6	119.78 (12)	C8—C7—C4	127.73 (13)
C1—C2—C3	119.00 (12)	C8—C7—H7	116.1
C1—C2—H2	120.5	C4—C7—H7	116.1
C3—C2—H2	120.5	C7—C8—C8i	124.37 (17)
C2—C3—C4	122.70 (12)	C7—C8—H8	117.8
C2—C3—H3	118.6	C8i—C8—H8	117.8
C4—C3—H3	118.6	O1—C9—H9A	109.5
C3—C4—C5	116.82 (12)	O1—C9—H9B	109.5
C3—C4—C7	119.55 (12)	H9A—C9—H9B	109.5
C5—C4—C7	123.56 (12)	O1—C9—H9C	109.5
C6—C5—C4	121.12 (12)	H9A—C9—H9C	109.5
C6—C5—H5	119.4	H9B—C9—H9C	109.5
C4—C5—H5	119.4
C9—O1—C1—C2	4.3 (2)	C7—C4—C5—C6	−175.32 (12)
C9—O1—C1—C6	−176.19 (14)	C4—C5—C6—C1	0.1 (2)
O1—C1—C2—C3	−179.72 (12)	O1—C1—C6—C5	179.15 (12)
C6—C1—C2—C3	0.81 (19)	C2—C1—C6—C5	−1.33 (19)
C1—C2—C3—C4	0.9 (2)	C3—C4—C7—C8	−170.76 (13)
C2—C3—C4—C5	−2.09 (19)	C5—C4—C7—C8	6.0 (2)
C2—C3—C4—C7	174.90 (13)	C4—C7—C8—C8i	175.49 (15)
C3—C4—C5—C6	1.54 (18)