(Z,E,Z)-1,6-Di-1-naphthyl-hexa-1,3,5-triene.

The title compound, C(26)H(20), lies about an inversion centre. The naphthalene unit and the hexa-triene chain are each approximately planar (maximum deviations of 0.0143 and 0.0042 Å, respectively), and are inclined to one another at a dihedral angle of 49.20 (4)°. The dihedral angle between the two naphthalene ring systems of neighboring mol-ecules is 85.71 (4)°.

Related literature

For the potential use of α,ω-diaryl­polyenes as non-linear optical materials, see: Geskin et al. (2003 ▶); Rumi et al. (2000 ▶). For a study of the relationship between the crystal structure and the photophysical properties of 1,6-diaryl­hexa-1,3,5-trienes, see: Sonoda et al. (2006 ▶); Sonoda, Goto et al. (2007 ▶). For related structures, see: Aldoshin et al. (1984 ▶); Sonoda et al. (2005 ▶); Sonoda, Tsuzuki et al. (2007 ▶).

Experimental

Crystal data

C26H20

M = 332.42

Monoclinic,

a = 5.0071 (8) Å

b = 11.0709 (17) Å

c = 16.110 (3) Å

β = 96.535 (3)°

V = 887.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 203 (2) K

0.30 × 0.10 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.910, T max = 0.997

5367 measured reflections

2023 independent reflections

1366 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.114

S = 1.01

2023 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000592/at2699sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000592/at2699Isup2.hkl

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

C26H20	F(000) = 352
Mr = 332.42	Dx = 1.244 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1467 reflections
a = 5.0071 (8) Å	θ = 2.6–27.1°
b = 11.0709 (17) Å	µ = 0.07 mm−1
c = 16.110 (3) Å	T = 203 K
β = 96.535 (3)°	Rectangular, pale yellow
V = 887.2 (3) Å3	0.30 × 0.10 × 0.05 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2023 independent reflections
Radiation source: rotating unit	1366 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 8.366 pixels mm-1	θmax = 28.3°, θmin = 2.2°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→14
Tmin = 0.910, Tmax = 0.997	l = −21→20
5367 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.1208P] where P = (Fo2 + 2Fc2)/3
2023 reflections	(Δ/σ)max = 0.001
118 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Experimental. Sheldrick, G. M. (1996). SADABS, program for scaling and correction of area detector data. University of Göttingen, Germany.

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	0.0718 (2)	0.18611 (12)	0.28101 (8)	0.0349 (3)
C2	0.2135 (3)	0.10461 (14)	0.33764 (9)	0.0425 (4)
H2	0.3383	0.0511	0.3183	0.051*
C3	0.1719 (3)	0.10250 (15)	0.42018 (9)	0.0506 (4)
H3	0.2711	0.0489	0.4570	0.061*
C4	−0.0171 (3)	0.17947 (16)	0.45017 (9)	0.0536 (4)
H4	−0.0446	0.1773	0.5069	0.064*
C5	−0.1600 (3)	0.25694 (15)	0.39761 (9)	0.0501 (4)
H5	−0.2894	0.3068	0.4182	0.060*
C6	−0.1188 (3)	0.26465 (13)	0.31206 (8)	0.0399 (3)
C7	−0.2601 (3)	0.34839 (14)	0.25750 (10)	0.0476 (4)
H7	−0.3870	0.4002	0.2776	0.057*
C8	−0.2140 (3)	0.35465 (14)	0.17611 (10)	0.0482 (4)
H8	−0.3063	0.4120	0.1406	0.058*
C9	−0.0295 (3)	0.27621 (13)	0.14452 (9)	0.0428 (4)
H9	−0.0016	0.2818	0.0879	0.051*
C10	0.1111 (3)	0.19160 (13)	0.19424 (8)	0.0369 (3)
C11	0.3027 (3)	0.10910 (13)	0.16049 (8)	0.0411 (3)
H11	0.4733	0.1020	0.1911	0.049*
C12	0.2587 (3)	0.04314 (13)	0.09057 (8)	0.0407 (3)
H12	0.4052	−0.0023	0.0761	0.049*
C13	0.0132 (3)	0.03363 (13)	0.03492 (8)	0.0386 (3)
H13	−0.1374	0.0771	0.0483	0.046*

	U11	U22	U33	U12	U13	U23
C1	0.0329 (6)	0.0326 (7)	0.0385 (7)	−0.0064 (6)	0.0006 (5)	−0.0059 (6)
C2	0.0416 (7)	0.0409 (8)	0.0441 (8)	−0.0017 (7)	0.0005 (6)	−0.0029 (7)
C3	0.0553 (9)	0.0523 (10)	0.0422 (8)	−0.0077 (8)	−0.0030 (7)	0.0048 (7)
C4	0.0622 (10)	0.0612 (11)	0.0381 (8)	−0.0137 (9)	0.0089 (7)	−0.0070 (8)
C5	0.0512 (9)	0.0513 (10)	0.0492 (9)	−0.0072 (8)	0.0121 (7)	−0.0165 (8)
C6	0.0383 (7)	0.0377 (8)	0.0435 (8)	−0.0067 (6)	0.0034 (6)	−0.0116 (6)
C7	0.0439 (8)	0.0402 (8)	0.0579 (9)	0.0055 (7)	0.0028 (7)	−0.0130 (7)
C8	0.0502 (8)	0.0384 (8)	0.0533 (9)	0.0053 (7)	−0.0059 (7)	−0.0020 (7)
C9	0.0464 (8)	0.0419 (8)	0.0394 (7)	−0.0024 (7)	0.0017 (6)	−0.0013 (6)
C10	0.0346 (7)	0.0366 (8)	0.0392 (7)	−0.0057 (6)	0.0023 (5)	−0.0051 (6)
C11	0.0360 (7)	0.0463 (9)	0.0409 (7)	−0.0001 (6)	0.0042 (6)	−0.0021 (7)
C12	0.0383 (7)	0.0434 (8)	0.0419 (7)	0.0007 (6)	0.0110 (6)	−0.0015 (7)
C13	0.0388 (7)	0.0384 (8)	0.0404 (7)	−0.0014 (6)	0.0127 (6)	0.0004 (6)

C1—C2	1.4153 (19)	C7—H7	0.9400
C1—C6	1.4232 (19)	C8—C9	1.405 (2)
C1—C10	1.4350 (18)	C8—H8	0.9400
C2—C3	1.369 (2)	C9—C10	1.3736 (19)
C2—H2	0.9400	C9—H9	0.9400
C3—C4	1.400 (2)	C10—C11	1.4727 (19)
C3—H3	0.9400	C11—C12	1.3395 (19)
C4—C5	1.351 (2)	C11—H11	0.9400
C4—H4	0.9400	C12—C13	1.4404 (18)
C5—C6	1.419 (2)	C12—H12	0.9400
C5—H5	0.9400	C13—C13i	1.343 (3)
C6—C7	1.411 (2)	C13—H13	0.9400
C7—C8	1.359 (2)
C2—C1—C6	118.04 (13)	C6—C7—H7	119.8
C2—C1—C10	122.72 (13)	C7—C8—C9	120.61 (14)
C6—C1—C10	119.24 (12)	C7—C8—H8	119.7
C3—C2—C1	121.08 (14)	C9—C8—H8	119.7
C3—C2—H2	119.5	C10—C9—C8	121.66 (13)
C1—C2—H2	119.5	C10—C9—H9	119.2
C2—C3—C4	120.56 (15)	C8—C9—H9	119.2
C2—C3—H3	119.7	C9—C10—C1	118.61 (13)
C4—C3—H3	119.7	C9—C10—C11	121.32 (13)
C5—C4—C3	120.03 (14)	C1—C10—C11	120.06 (12)
C5—C4—H4	120.0	C12—C11—C10	126.65 (12)
C3—C4—H4	120.0	C12—C11—H11	116.7
C4—C5—C6	121.45 (15)	C10—C11—H11	116.7
C4—C5—H5	119.3	C11—C12—C13	127.61 (13)
C6—C5—H5	119.3	C11—C12—H12	116.2
C7—C6—C5	121.78 (14)	C13—C12—H12	116.2
C7—C6—C1	119.41 (13)	C13i—C13—C12	123.89 (16)
C5—C6—C1	118.81 (14)	C13i—C13—H13	118.1
C8—C7—C6	120.41 (14)	C12—C13—H13	118.1
C8—C7—H7	119.8
C6—C1—C2—C3	−1.0 (2)	C6—C7—C8—C9	1.4 (2)
C10—C1—C2—C3	179.57 (13)	C7—C8—C9—C10	−0.4 (2)
C1—C2—C3—C4	1.4 (2)	C8—C9—C10—C1	−1.6 (2)
C2—C3—C4—C5	−0.1 (2)	C8—C9—C10—C11	179.55 (13)
C3—C4—C5—C6	−1.5 (2)	C2—C1—C10—C9	−178.01 (13)
C4—C5—C6—C7	−177.64 (14)	C6—C1—C10—C9	2.54 (18)
C4—C5—C6—C1	1.9 (2)	C2—C1—C10—C11	0.90 (19)
C2—C1—C6—C7	178.92 (12)	C6—C1—C10—C11	−178.55 (12)
C10—C1—C6—C7	−1.60 (19)	C9—C10—C11—C12	−48.6 (2)
C2—C1—C6—C5	−0.66 (18)	C1—C10—C11—C12	132.53 (15)
C10—C1—C6—C5	178.82 (12)	C10—C11—C12—C13	−3.0 (2)
C5—C6—C7—C8	179.19 (14)	C11—C12—C13—C13i	179.04 (17)
C1—C6—C7—C8	−0.4 (2)