4,4′-Bis(2-methoxy­lstyr­yl)biphen­yl

Li, Y.-F.; Jian, F.-F.

doi:10.1107/S1600536809026920

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1930

doi:10.1107/S1600536809026920

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4,4′-Bis(2-methoxylstyryl)biphenyl

Yu-Feng Li ^a and Fang-Fang Jian ^b ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 24 June 2009; accepted 9 July 2009; online 18 July 2009)

The title compound, C₃₀H₂₆O₂, was prepared by the reaction of a Wittig reagent and 2-methoxybenzaldehyde. The molecule lies about an inversion centre located at the midpoint of the C—C bond between the inner benzene rings. The crystal structure is stabilized by C—H⋯π interactions.

Related literature

For the optical properties of ethylene biphenyls, see: Song et al. (2003 ). For comparative bond lengths, see: Trueblood et al. (1982 ).

Experimental

Crystal data

C₃₀H₂₆O₂
M_r = 418.51
Monoclinic, P 2₁ /c
a = 15.499 (3) Å
b = 5.5050 (11) Å
c = 13.445 (3) Å
β = 98.61 (3)°
V = 1134.2 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
2541 measured reflections
2431 independent reflections
1144 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.218
S = 1.01
2431 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1C⋯Cg1ⁱ	0.96	2.76	3.611 (3)	149
C15—H15A⋯Cg2ⁱⁱ	0.93	2.91	3.643 (3)	137
Symmetry codes: (i) x, y-1, z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 and Cg2 are the centroids of the C2–C7 and C10–C15 rings,respectively.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026920/at2831sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026920/at2831Isup2.hkl

checkCIF report

Comment top

Ethylene biphenyl have received considerable attention in the literature. They are attractive from several points of view, such as the optics characteristic. (Song et al., 2003). As part of our search for new ethylene biphenyl compounds we synthesized the title compound (I), and describe its structure here.

As shown in Fig. 1, the molecule has an inversion centre lied on the midpoint of the C—C bond between the inner benzene rings. The C8—C9 bond length of 1.314 (4)Å is comparable with C—C double bond [1.336 (2) Å] reported (Trueblood et al., 1982).

In the structure, there is no classcial hydrogen bonds. The crystal structure is stabilized by C—H···π interactions (Table 1).

Related literature top

For the optical properties of ethylene biphenyls, see: Song et al. (2003). For comparison bond lengths, see: Trueblood et al. (1982). Cg1 and Cg2 are the centroids of the C2–C7 and C10–C15 rings,respectively.

Experimental top

A mixture of the Wittig-reagent (0.1 mol), and 2-methoxybenzaldehyde (0.2 mol) was stirred in refluxing N,N-dimethylformamide (20 mL) for 4 h to afford the title compound (0.084 mol, yield 84%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

4,4'-Bis(2-methoxylstyryl)biphenyl top

Crystal data top

C₃₀H₂₆O₂	F(000) = 444
M_r = 418.51	D_x = 1.225 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 987 reflections
a = 15.499 (3) Å	θ = 2.2–27.5°
b = 5.5050 (11) Å	µ = 0.08 mm⁻¹
c = 13.445 (3) Å	T = 293 K
β = 98.61 (3)°	Block, yellow
V = 1134.2 (4) Å³	0.25 × 0.20 × 0.18 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	1144 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 27.0°, θ_min = 1.3°
ϕ and ω scans	h = −18→18
2541 measured reflections	k = −6→0
2431 independent reflections	l = −16→0

Refinement top

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)] = 0.065	H-atom parameters constrained
wR(F²) = 0.218	w = 1/[σ²(F_o²) + (0.1165P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2431 reflections	Δρ_max = 0.22 e Å⁻³
146 parameters	Δρ_min = −0.18 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: 0.045 (8)

Crystal data top

C₃₀H₂₆O₂	V = 1134.2 (4) Å³
M_r = 418.51	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.499 (3) Å	µ = 0.08 mm⁻¹
b = 5.5050 (11) Å	T = 293 K
c = 13.445 (3) Å	0.25 × 0.20 × 0.18 mm
β = 98.61 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1144 reflections with I > 2σ(I)
2541 measured reflections	R_int = 0.031
2431 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.218	H-atom parameters constrained
S = 1.01	Δρ_max = 0.22 e Å⁻³
2431 reflections	Δρ_min = −0.18 e Å⁻³
146 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.37628 (14)	0.1134 (4)	0.17470 (14)	0.0684 (7)
C1	0.4420 (2)	−0.0626 (6)	0.1680 (2)	0.0738 (11)
H1A	0.4491	−0.1627	0.2271	0.111*
H1B	0.4961	0.0178	0.1627	0.111*
H1C	0.4254	−0.1619	0.1096	0.111*
C2	0.35652 (18)	0.2759 (5)	0.09673 (19)	0.0493 (7)
C3	0.3997 (2)	0.2830 (6)	0.0136 (2)	0.0602 (9)
H3A	0.4442	0.1727	0.0082	0.072*
C4	0.3770 (2)	0.4529 (7)	−0.0611 (2)	0.0665 (10)
H4A	0.4066	0.4568	−0.1164	0.080*
C5	0.3114 (2)	0.6160 (6)	−0.0545 (2)	0.0625 (9)
H5A	0.2963	0.7302	−0.1051	0.075*
C6	0.26746 (19)	0.6097 (6)	0.0283 (2)	0.0565 (8)
H6A	0.2233	0.7216	0.0327	0.068*
C7	0.28816 (16)	0.4391 (5)	0.10519 (19)	0.0456 (7)
C8	0.24047 (17)	0.4232 (5)	0.19277 (19)	0.0497 (8)
H8A	0.2537	0.2911	0.2354	0.060*
C9	0.18161 (18)	0.5755 (5)	0.2166 (2)	0.0493 (8)
H9A	0.1705	0.7120	0.1759	0.059*
C10	0.13109 (17)	0.5531 (5)	0.30137 (19)	0.0434 (7)
C11	0.1426 (2)	0.3639 (6)	0.3705 (2)	0.0616 (9)
H11A	0.1851	0.2472	0.3654	0.074*
C12	0.0920 (2)	0.3457 (5)	0.4468 (2)	0.0615 (9)
H12A	0.1016	0.2159	0.4914	0.074*
C13	0.02809 (16)	0.5122 (5)	0.45942 (19)	0.0406 (6)
C14	0.0180 (2)	0.7035 (5)	0.3911 (2)	0.0556 (8)
H14A	−0.0239	0.8216	0.3970	0.067*
C15	0.0683 (2)	0.7237 (6)	0.3145 (2)	0.0576 (9)
H15A	0.0596	0.8553	0.2707	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0824 (16)	0.0795 (15)	0.0477 (12)	0.0305 (13)	0.0238 (11)	0.0099 (12)
C1	0.083 (2)	0.081 (3)	0.057 (2)	0.027 (2)	0.0114 (17)	−0.0030 (18)
C2	0.0517 (16)	0.0613 (18)	0.0365 (15)	−0.0004 (15)	0.0114 (12)	−0.0031 (14)
C3	0.0571 (18)	0.082 (2)	0.0457 (17)	0.0071 (17)	0.0228 (15)	−0.0038 (17)
C4	0.0594 (19)	0.104 (3)	0.0409 (17)	−0.0055 (19)	0.0235 (14)	0.0008 (18)
C5	0.0603 (19)	0.089 (2)	0.0393 (16)	−0.0015 (19)	0.0110 (14)	0.0128 (17)
C6	0.0491 (16)	0.075 (2)	0.0465 (16)	0.0034 (16)	0.0091 (13)	0.0075 (16)
C7	0.0404 (15)	0.063 (2)	0.0350 (14)	−0.0034 (13)	0.0107 (11)	−0.0011 (13)
C8	0.0475 (16)	0.065 (2)	0.0393 (15)	0.0066 (15)	0.0136 (12)	0.0041 (14)
C9	0.0523 (17)	0.0556 (19)	0.0423 (15)	−0.0007 (15)	0.0142 (12)	0.0004 (13)
C10	0.0411 (15)	0.0501 (17)	0.0397 (15)	−0.0015 (13)	0.0081 (12)	−0.0064 (13)
C11	0.0591 (18)	0.065 (2)	0.067 (2)	0.0249 (16)	0.0306 (16)	0.0138 (17)
C12	0.067 (2)	0.063 (2)	0.0608 (19)	0.0243 (17)	0.0318 (16)	0.0209 (16)
C13	0.0403 (14)	0.0462 (15)	0.0357 (13)	−0.0002 (12)	0.0078 (10)	−0.0044 (12)
C14	0.0585 (18)	0.0579 (19)	0.0554 (17)	0.0198 (15)	0.0248 (14)	0.0066 (15)
C15	0.0662 (19)	0.062 (2)	0.0490 (16)	0.0172 (16)	0.0235 (15)	0.0154 (15)

Geometric parameters (Å, º) top

O1—C2	1.377 (3)	C8—C9	1.314 (4)
O1—C1	1.419 (4)	C8—H8A	0.9300
C1—H1A	0.9600	C9—C10	1.482 (4)
C1—H1B	0.9600	C9—H9A	0.9300
C1—H1C	0.9600	C10—C15	1.383 (4)
C2—C3	1.386 (4)	C10—C11	1.389 (4)
C2—C7	1.407 (4)	C11—C12	1.386 (4)
C3—C4	1.379 (4)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C13	1.379 (4)
C4—C5	1.370 (4)	C12—H12A	0.9300
C4—H4A	0.9300	C13—C14	1.391 (4)
C5—C6	1.390 (4)	C13—C13ⁱ	1.500 (5)
C5—H5A	0.9300	C14—C15	1.387 (4)
C6—C7	1.398 (4)	C14—H14A	0.9300
C6—H6A	0.9300	C15—H15A	0.9300
C7—C8	1.484 (3)

C2—O1—C1	118.4 (2)	C9—C8—C7	127.1 (3)
O1—C1—H1A	109.5	C9—C8—H8A	116.5
O1—C1—H1B	109.5	C7—C8—H8A	116.5
H1A—C1—H1B	109.5	C8—C9—C10	126.9 (3)
O1—C1—H1C	109.5	C8—C9—H9A	116.5
H1A—C1—H1C	109.5	C10—C9—H9A	116.5
H1B—C1—H1C	109.5	C15—C10—C11	116.5 (2)
O1—C2—C3	123.6 (3)	C15—C10—C9	120.3 (3)
O1—C2—C7	116.0 (2)	C11—C10—C9	123.2 (2)
C3—C2—C7	120.5 (3)	C12—C11—C10	121.3 (3)
C4—C3—C2	120.4 (3)	C12—C11—H11A	119.4
C4—C3—H3A	119.8	C10—C11—H11A	119.4
C2—C3—H3A	119.8	C13—C12—C11	122.7 (3)
C5—C4—C3	120.5 (3)	C13—C12—H12A	118.7
C5—C4—H4A	119.7	C11—C12—H12A	118.7
C3—C4—H4A	119.7	C12—C13—C14	115.7 (2)
C4—C5—C6	119.5 (3)	C12—C13—C13ⁱ	122.4 (3)
C4—C5—H5A	120.2	C14—C13—C13ⁱ	121.8 (3)
C6—C5—H5A	120.2	C15—C14—C13	122.1 (3)
C5—C6—C7	121.6 (3)	C15—C14—H14A	119.0
C5—C6—H6A	119.2	C13—C14—H14A	119.0
C7—C6—H6A	119.2	C10—C15—C14	121.7 (3)
C6—C7—C2	117.5 (2)	C10—C15—H15A	119.2
C6—C7—C8	122.7 (3)	C14—C15—H15A	119.2
C2—C7—C8	119.8 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···Cg1ⁱⁱ	0.96	2.76	3.611 (3)	149
C15—H15A···Cg2ⁱⁱⁱ	0.93	2.91	3.643 (3)	137

Symmetry codes: (ii) x, y−1, z; (iii) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₀H₂₆O₂
M_r	418.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.499 (3), 5.5050 (11), 13.445 (3)
β (°)	98.61 (3)
V (Å³)	1134.2 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2541, 2431, 1144
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.218, 1.01
No. of reflections	2431
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···Cg1ⁱ	0.96	2.76	3.611 (3)	149
C15—H15A···Cg2ⁱⁱ	0.93	2.91	3.643 (3)	137

Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z+1/2.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Song, H. C., Xu, X. H. & Liu, G. R. (2003). Chin. Chem. Res. 14, 1–5. CAS Google Scholar
Trueblood, K., Mirsky, K., Maverick, E., Knobler, C. & Grossenbacher, L. (1982). Acta Cryst. B38, 2428–2435. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar