PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o3000.
Published online 2010 October 31. doi:  10.1107/S1600536810042613
PMCID: PMC3009162

1,2-Bis(4-methyl­phen­oxy)ethane

Abstract

In the title compound, C16H18O2, the two aromatic rings are almost orthogonal, making a dihedral angle of 89.41 (2)°. There is a C—H(...)π contact between the methyl­ene group and the 4-methyl­phenyl ring. The molecule exhibits twofold symmetry..

Related literature

For background to the uses of the title compound and further synthetic details, see: Xiao et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3000-scheme1.jpg

Experimental

Crystal data

  • C16H18O2
  • M r = 242.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3000-efi1.jpg
  • a = 27.173 (5) Å
  • b = 5.5510 (11) Å
  • c = 9.2780 (19) Å
  • β = 93.55 (3)°
  • V = 1396.8 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.30 × 0.30 × 0.05 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.978, T max = 0.996
  • 2542 measured reflections
  • 1276 independent reflections
  • 636 reflections with I > 2σ(I)
  • R int = 0.083
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.131
  • S = 1.00
  • 1276 reflections
  • 82 parameters
  • H-atom parameters constrained
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 [triangle]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042613/ng5032sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042613/ng5032Isup2.hkl

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

Acknowledgments

This research work was supported financially by the Department of Science and Technology of Jiangsu Province (BE200830457) and ‘863’ project (2007 A A02Z211) of the Ministry of Science and Technology.

supplementary crystallographic information

Experimental

p-Cresol (30.3 g,0.28 mol) was added to a stirred solution of sodium hydroxide(16 g,0.4 mol) in 200 ml of ethanol at room temperature. After stirring for 1 h, ethylene dibromide(28.1 g,0.15 mol) was added. The reaction mixture was stirred and heated under refluxing for another 15 h and then poured into a 5% aqueous solution of NaOH (500 ml). The resulting mixture was cooled to room temperature and filtered. The remaining solid was washed with water(2 x 50 ml) and ethanol(2 x 40 ml),and then dried in vacuo to give the products 13.6 g as white solids (40.1%) (Xiao et al., 2007) Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Refinement

H atoms were positioned geometrically with C—H = 0.93, 0.98 and 0.97 Å for aromatic, methine and methylene H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2 (or 1.5 for methyl groups) times Ueq(C).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability levels.
Fig. 2.
A practical packing diagram of the title compound. There is no intramolecular or intermolecular hydrogen bonds in the crystal.

Crystal data

C16H18O2F(000) = 520
Mr = 242.30Dx = 1.152 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 27.173 (5) ÅCell parameters from 25 reflections
b = 5.5510 (11) Åθ = 9–12°
c = 9.2780 (19) ŵ = 0.08 mm1
β = 93.55 (3)°T = 293 K
V = 1396.8 (5) Å3Prism, colorless
Z = 40.30 × 0.30 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer636 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.083
graphiteθmax = 25.3°, θmin = 1.5°
ω/2θ scansh = −32→32
Absorption correction: ψ scan (North et al., 1968)k = 0→6
Tmin = 0.978, Tmax = 0.996l = −11→11
2542 measured reflections3 standard reflections every 200 reflections
1276 independent reflections intensity decay: 1%

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.022P)2] where P = (Fo2 + 2Fc2)/3
1276 reflections(Δ/σ)max < 0.001
82 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = −0.14 e Å3

Special details

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)

xyzUiso*/Ueq
O0.52863 (6)0.2044 (3)0.12559 (15)0.0667 (6)
C10.65274 (9)0.1203 (6)−0.0026 (3)0.0768 (9)
H1A0.67930.01470.00750.092*
C20.61155 (9)0.0757 (5)0.0739 (2)0.0660 (7)
H2A0.6105−0.05780.13420.079*
C30.57211 (9)0.2313 (5)0.0597 (2)0.0543 (6)
C40.57452 (9)0.4268 (5)−0.0305 (2)0.0635 (7)
H4A0.54790.5321−0.04110.076*
C50.61569 (10)0.4681 (5)−0.1049 (3)0.0704 (8)
H5A0.61660.6022−0.16470.085*
C60.65576 (10)0.3158 (6)−0.0932 (3)0.0752 (9)
C70.70126 (10)0.3646 (6)−0.1759 (3)0.1183 (13)
H7A0.72540.2418−0.15390.177*
H7B0.71470.5190−0.14850.177*
H7C0.69240.3637−0.27770.177*
C80.52487 (8)0.0048 (5)0.2210 (2)0.0663 (8)
H8A0.54990.01690.29980.080*
H8B0.5300−0.14440.16960.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O0.0811 (12)0.0665 (12)0.0532 (9)0.0140 (11)0.0085 (9)0.0125 (11)
C10.0708 (18)0.082 (2)0.0774 (18)0.0161 (17)0.0044 (15)−0.001 (2)
C20.0797 (17)0.0638 (18)0.0538 (14)0.0115 (17)−0.0030 (13)0.0044 (16)
C30.0670 (16)0.0574 (16)0.0382 (12)0.0066 (15)−0.0003 (12)−0.0046 (13)
C40.0806 (18)0.0546 (17)0.0548 (13)0.0090 (15)0.0012 (13)0.0019 (16)
C50.0858 (19)0.0658 (19)0.0595 (15)−0.0035 (17)0.0023 (15)0.0060 (17)
C60.0771 (19)0.087 (2)0.0617 (16)−0.0028 (19)0.0093 (15)−0.006 (2)
C70.088 (2)0.152 (4)0.118 (2)−0.005 (2)0.0279 (19)0.008 (3)
C80.0914 (19)0.0611 (16)0.0462 (12)0.0077 (15)0.0023 (12)0.0064 (14)

Geometric parameters (Å, °)

O—C31.372 (2)C5—C61.377 (4)
O—C81.426 (3)C5—H5A0.9300
C1—C61.378 (4)C6—C71.519 (3)
C1—C21.384 (3)C7—H7A0.9600
C1—H1A0.9300C7—H7B0.9600
C2—C31.376 (3)C7—H7C0.9600
C2—H2A0.9300C8—C8i1.485 (4)
C3—C41.375 (3)C8—H8A0.9700
C4—C51.370 (3)C8—H8B0.9700
C4—H4A0.9300
C3—O—C8117.25 (18)C1—C6—C5117.0 (3)
C6—C1—C2122.3 (3)C1—C6—C7122.0 (3)
C6—C1—H1A118.9C5—C6—C7121.0 (3)
C2—C1—H1A118.9C6—C7—H7A109.5
C3—C2—C1119.2 (3)C6—C7—H7B109.5
C3—C2—H2A120.4H7A—C7—H7B109.5
C1—C2—H2A120.4C6—C7—H7C109.5
O—C3—C4115.6 (2)H7A—C7—H7C109.5
O—C3—C2125.2 (2)H7B—C7—H7C109.5
C4—C3—C2119.2 (2)O—C8—C8i109.05 (18)
C5—C4—C3120.7 (3)O—C8—H8A109.9
C5—C4—H4A119.7C8i—C8—H8A109.9
C3—C4—H4A119.7O—C8—H8B109.9
C4—C5—C6121.6 (3)C8i—C8—H8B109.9
C4—C5—H5A119.2H8A—C8—H8B108.3
C6—C5—H5A119.2
C6—C1—C2—C3−0.1 (4)C3—C4—C5—C60.5 (4)
C8—O—C3—C4−179.46 (19)C2—C1—C6—C50.1 (4)
C8—O—C3—C22.8 (3)C2—C1—C6—C7179.5 (2)
C1—C2—C3—O177.9 (2)C4—C5—C6—C1−0.3 (4)
C1—C2—C3—C40.2 (3)C4—C5—C6—C7−179.7 (3)
O—C3—C4—C5−178.3 (2)C3—O—C8—C8i−179.03 (19)
C2—C3—C4—C5−0.4 (3)

Symmetry codes: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8—H8A···Cg10.972.853.664 (3)142

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5032).

References

  • Enraf–Nonius (1994). CAD-4 EXPRESS Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Xiao, X., Sun, J., Li, X., Li, H. & Wang, Y. (2007). J. Mol. Catal. A, 267, 86–91.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography