organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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(1E,3E)-1,4-Bis(4-meth­­oxy­phen­yl)buta-1,3-diene

aPhotosciences and Photonics Section, Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology, CSIR, Trivandrum, Kerala 695 019, India, and bDepartment of Chemistry and Biochemistry and Center for Nanoscience, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121-4400, USA
*Correspondence e-mail: sureshdas@niist.res.in

(Received 6 July 2010; accepted 16 September 2010; online 30 September 2010)

The title compound, C18H18O2, which exhibits blue emission in the solid state, is an inter­mediate in the preparation of liquid crystals and polymers. The mol­ecule is located on an inversion centre. In the crystal, mol­ecules are arranged in a herringbone motif.

Related literature

For related structures, see: George et al. (1998[George, M., Das, S., Ashokan, C. V., Rath, N. P. & George, M. V. (1998). Acta Cryst. C54, 1033-1036.]); Vishnumurthy et al. (2002[Vishnumurthy, K., Guru Row, T. N. & Venkatesan, K. (2002). Photochem. Photobiol. Sci. 1, 427-430.]); Davis et al. (2004[Davis, R., Abraham, S., Rath, N. P. & Das, S. (2004). New J. Chem. 28, 1368-1372.], 2008[Davis, R., Kumar, N. S. S., Abraham, S., Suresh, C. H., Rath, N. P., Tamaoki, N. & Das, S. (2008). J. Phys. Chem. C, 112, 2137-2146.]); Kumar et al. (2009[Kumar, N. S. S., Varghese, S., Suresh, C. H., Rath, N. P. & Das, S. (2009). J. Phys. Chem. C, 113, 11927-11935.]); Ono et al. (2009[Ono, K., Tokura, O. & Tomura, M. (2009). Acta Cryst. E65, o2118.]). For the synthesis and the use of the title compound in the preparation of polymers and chiral liquid crystals, see: Rotarski (1908[Rotarski, Th. (1908). Ber. Dtsch Chem. Ges. 41, 1994-1998.]); Wang et al. (2003[Wang, S. J., Tjong, S. C., Meng, Y. Z., Fung, M. K., Lee, S. T. & Hay, A. S. (2003). J. Appl. Polym. Sci. 89, 1645-1651.]); Das et al. (2008[Das, S., Narayan, G., Abraham, S., Jayaraman, N., Singh, M. K., Prasad, S. K. & Rao, D. S. S. (2008). Adv. Funct. Mater. 18, 1632-1640.]). For mol­ecules with a herringbone arrangement, see: Koren et al. (2003[Koren, A. B., Curtis, M. D., Francis, A. H. & Kampf, J. W. (2003). J. Am. Chem. Soc. 125, 5040-5050.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18O2

  • Mr = 266.32

  • Orthorhombic, P b c a

  • 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[Sheldrick, G. M. (2006). SADABS. University of Göttingen, Germany.]) Tmin = 0.981, Tmax = 0.983

  • 40427 measured reflections

  • 1658 independent reflections

  • 1287 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 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[Bruker (2001). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Although the crystal structures of a number of butadiene molecules have been reported (George et al., 1998; Vishnumurthy et al., 2002; Davis et al., 2004, 2008; Kumar et al., 2009; Ono et al., 2009), that of the title compound, C18H18O2, (I), has not been determined and the structure is reported here (Fig. 1). There are four molecules of (I) per unit cell. The symmetrical molecules are arranged in a herringbone fashion (Koren et al., 2003) in which the molecules are packed in an edge-to-face orientation (Fig. 2).

Thermal properties: On heating, crystals of (I) melted at 237 °C, which on further heating sublimed at 246 °C. The sublimed-condensed crystals were chemically unaltered as evidenced by NMR and MS analyses.

Related literature top

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 top

A mixture of diethyl-4-methoxybenzylphosphonate (1 equiv) and potassium tert-butoxide (5 equiv) were stirred in dry DMF at room temperature and cooled to 273 K. 4-Methoxycinnamaldehyde (1 equiv) dissolved in dry DMF was slowly added into the solution. The reaction mixture was allowed to stir for 12 h at room temperature. TLC analysis indicated completion of reaction. Reaction mixture was poured into ice water, extracted with dichloromethane and concentrated under reduced pressure. The residue was washed with ethyl acetate and filtered. The compound being insoluble in ethyl acetate remained in the residue. This was repeatedly washed with ethyl acetate (small quantities) to obtain pure title compound. The small amount of compound which remained in the filtrate was recovered by column chromatography through silica gel (100–200 mesh), using 5% ethyl acetate/hexane as the mobile phase. Single crystals obtained from ethylacetate at room temperature were of poor quality (high R value) and the structure determination was carried out at 100 K. Fresh crystals were grown from chloroform/hexanes at room temperature which were of higher quality to permit X-ray analysis at 293 K. The data presented herein are from the latter determination.

Refinement top

H atoms bonded to N and O atoms were located in a difference map and refined with distance restraints of O—H = 0.84 (2) and N—H = 0.87 (2) Å, and with Uiso(H) = 1.2Ueq(N,O). Other H atoms were positioned geometrically and refined using a riding model (including free rotation about the ethanol C—C bond), with C—H = 0.95–0.99 Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The herringbone packing of (I) in the crystal structure.
(1E,3E)-1,4-Bis(4-methoxyphenyl)buta-1,3-diene top
Crystal data top
C18H18O2F(000) = 568
Mr = 266.32Dx = 1.224 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 7512 reflections
a = 7.3543 (3) Åθ = 2.6–23.6°
b = 6.2617 (3) ŵ = 0.08 mm1
c = 31.3872 (13) ÅT = 293 K
V = 1445.39 (11) Å3Pyramidal, colourless
Z = 40.25 × 0.22 × 0.22 mm
Data collection top
Bruker X8 APEXII CCD area-detector
diffractometer
1658 independent reflections
Radiation source: fine-focus sealed tube1287 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ϕ and ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: numerical
(SADABS; Sheldrick, 2006)
h = 89
Tmin = 0.981, Tmax = 0.983k = 88
40427 measured reflectionsl = 4037
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-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 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.13 e Å3
Crystal data top
C18H18O2V = 1445.39 (11) Å3
Mr = 266.32Z = 4
Orthorhombic, PbcaMo Kα radiation
a = 7.3543 (3) ŵ = 0.08 mm1
b = 6.2617 (3) ÅT = 293 K
c = 31.3872 (13) Å0.25 × 0.22 × 0.22 mm
Data collection top
Bruker X8 APEXII CCD area-detector
diffractometer
1658 independent reflections
Absorption correction: numerical
(SADABS; Sheldrick, 2006)
1287 reflections with I > 2σ(I)
Tmin = 0.981, Tmax = 0.983Rint = 0.036
40427 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 1.08Δρmax = 0.13 e Å3
1658 reflectionsΔρmin = 0.13 e Å3
92 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.01884 (15)0.42509 (16)0.19955 (3)0.0584 (3)
C10.00667 (17)0.4944 (2)0.15818 (4)0.0420 (3)
C20.07908 (18)0.3855 (2)0.12580 (4)0.0458 (3)
H20.13410.25430.13100.055*
C30.08211 (18)0.4740 (2)0.08547 (4)0.0441 (3)
H30.13860.39880.06360.053*
C40.00422 (16)0.6707 (2)0.07623 (4)0.0396 (3)
C50.08465 (17)0.7752 (2)0.10963 (4)0.0440 (3)
H50.14110.90560.10460.053*
C60.09002 (18)0.6884 (2)0.14980 (4)0.0455 (3)
H60.15010.76050.17160.055*
C70.02594 (18)0.7620 (2)0.03382 (4)0.0452 (3)
H70.07690.67290.01330.054*
C80.01863 (18)0.9584 (2)0.02086 (4)0.0461 (3)
H80.07771.04720.04020.055*
C90.0738 (3)0.2339 (3)0.21039 (5)0.0789 (6)
H9A0.02540.11760.19400.118*
H9B0.05770.20500.24020.118*
H9C0.20100.24970.20430.118*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0773 (7)0.0568 (6)0.0410 (6)0.0056 (6)0.0018 (5)0.0061 (5)
C10.0447 (7)0.0442 (7)0.0371 (7)0.0047 (6)0.0013 (5)0.0012 (6)
C20.0485 (8)0.0395 (7)0.0495 (8)0.0068 (6)0.0004 (6)0.0015 (6)
C30.0454 (7)0.0431 (7)0.0439 (7)0.0041 (6)0.0049 (6)0.0034 (6)
C40.0366 (6)0.0405 (7)0.0416 (7)0.0029 (5)0.0018 (5)0.0007 (5)
C50.0446 (7)0.0395 (7)0.0479 (8)0.0056 (6)0.0001 (6)0.0005 (6)
C60.0485 (8)0.0439 (7)0.0441 (7)0.0043 (6)0.0036 (6)0.0047 (6)
C70.0464 (7)0.0484 (8)0.0407 (7)0.0010 (6)0.0012 (6)0.0009 (6)
C80.0463 (7)0.0488 (8)0.0430 (7)0.0031 (6)0.0036 (6)0.0015 (6)
C90.1102 (16)0.0692 (11)0.0574 (10)0.0158 (11)0.0010 (10)0.0204 (9)
Geometric parameters (Å, º) top
O1—C11.3721 (15)C5—C61.3735 (18)
O1—C91.4190 (19)C5—H50.9300
C1—C21.3768 (18)C6—H60.9300
C1—C61.3860 (18)C7—C81.3367 (19)
C2—C31.3820 (18)C7—H70.9300
C2—H20.9300C8—C8i1.435 (3)
C3—C41.3890 (18)C8—H80.9300
C3—H30.9300C9—H9A0.9600
C4—C51.3978 (18)C9—H9B0.9600
C4—C71.4573 (18)C9—H9C0.9600
C1—O1—C9117.55 (12)C5—C6—C1120.54 (12)
O1—C1—C2124.87 (12)C5—C6—H6119.7
O1—C1—C6115.34 (12)C1—C6—H6119.7
C2—C1—C6119.78 (12)C8—C7—C4127.73 (13)
C1—C2—C3119.00 (12)C8—C7—H7116.1
C1—C2—H2120.5C4—C7—H7116.1
C3—C2—H2120.5C7—C8—C8i124.37 (17)
C2—C3—C4122.70 (12)C7—C8—H8117.8
C2—C3—H3118.6C8i—C8—H8117.8
C4—C3—H3118.6O1—C9—H9A109.5
C3—C4—C5116.82 (12)O1—C9—H9B109.5
C3—C4—C7119.55 (12)H9A—C9—H9B109.5
C5—C4—C7123.56 (12)O1—C9—H9C109.5
C6—C5—C4121.12 (12)H9A—C9—H9C109.5
C6—C5—H5119.4H9B—C9—H9C109.5
C4—C5—H5119.4
C9—O1—C1—C24.3 (2)C7—C4—C5—C6175.32 (12)
C9—O1—C1—C6176.19 (14)C4—C5—C6—C10.1 (2)
O1—C1—C2—C3179.72 (12)O1—C1—C6—C5179.15 (12)
C6—C1—C2—C30.81 (19)C2—C1—C6—C51.33 (19)
C1—C2—C3—C40.9 (2)C3—C4—C7—C8170.76 (13)
C2—C3—C4—C52.09 (19)C5—C4—C7—C86.0 (2)
C2—C3—C4—C7174.90 (13)C4—C7—C8—C8i175.49 (15)
C3—C4—C5—C61.54 (18)
Symmetry code: (i) x, y+2, z.

Experimental details

Crystal data
Chemical formulaC18H18O2
Mr266.32
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)7.3543 (3), 6.2617 (3), 31.3872 (13)
V3)1445.39 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.25 × 0.22 × 0.22
Data collection
DiffractometerBruker X8 APEXII CCD area-detector
diffractometer
Absorption correctionNumerical
(SADABS; Sheldrick, 2006)
Tmin, Tmax0.981, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
40427, 1658, 1287
Rint0.036
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.110, 1.08
No. of reflections1658
No. of parameters92
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.13, 0.13

Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Footnotes

Present address: Piramal Healthcare Limited, Mumbai 400013, India.

Acknowledgements

Research grants from the Department of Science and Technology (DST), Government of India, are gratefully acknowledged. This is contribution No. PPS-300 from PPS-NIIST. GN is grateful to the Council of Scientific and Industrial Research (CSIR) for a research fellowship. Funding from the National Science Foundation (MRI,CHE-0420497) for purchase of the APEXII diffractometer is also acknowledged.

References

First citationBruker (2001). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationDas, S., Narayan, G., Abraham, S., Jayaraman, N., Singh, M. K., Prasad, S. K. & Rao, D. S. S. (2008). Adv. Funct. Mater. 18, 1632–1640.  Web of Science CrossRef CAS
First citationDavis, R., Abraham, S., Rath, N. P. & Das, S. (2004). New J. Chem. 28, 1368–1372.  Web of Science CSD CrossRef CAS
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First citationOno, K., Tokura, O. & Tomura, M. (2009). Acta Cryst. E65, o2118.  Web of Science CSD CrossRef IUCr Journals
First citationRotarski, Th. (1908). Ber. Dtsch Chem. Ges. 41, 1994–1998.  CrossRef CAS
First citationSheldrick, G. M. (2006). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
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First citationWang, S. J., Tjong, S. C., Meng, Y. Z., Fung, M. K., Lee, S. T. & Hay, A. S. (2003). J. Appl. Polym. Sci. 89, 1645–1651.  Web of Science CrossRef CAS

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