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

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ISSN: 2056-9890

1,2-Bis(4-meth­­oxy­phen­­oxy)ethane

aSchool of Petrochemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, People's Republic of China, and bHigh Technology Research Institute of Nanjing University, Changzhou 213162, Jiangsu, People's Republic of China
*Correspondence e-mail: wkcoool@yahoo.cn

(Received 12 March 2013; accepted 13 March 2013; online 16 March 2013)

The whole mol­ecule of the title compound, C16H18O4, is generated by twofold rotational symmetry; the twofold axis bis­ects the central C—C bond. The O—C—C—O torsion angle about the central C—C bond is 69.45 (16)°. Symmetry-related benzene rings are inclined to one another by 64.91 (8)°. In the crystal, mol­ecules are connected by C—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the synthesis, uses and properties of the title compound, see: Saito et al. (1988[Saito, T., Kitani, M. & Ishibashi, T. (1988). Jpn Patent No. JP 63156731.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C16H18O4

  • Mr = 274.32

  • Monoclinic, C 2/c

  • a = 26.073 (4) Å

  • b = 5.5538 (8) Å

  • c = 9.7591 (14) Å

  • β = 102.211 (3)°

  • V = 1381.2 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.20 × 0.18 × 0.15 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.981, Tmax = 0.986

  • 3780 measured reflections

  • 1277 independent reflections

  • 976 reflections with I > 2σ(I)

  • Rint = 0.023

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.224

  • S = 1.10

  • 1277 reflections

  • 93 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1—H1B⋯O1i 0.96 2.60 3.453 (2) 148
C6—H6⋯O2ii 0.93 2.59 3.490 (2) 163
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (ii) -x, -y+2, -z.

Data collection: CAD-4 Software (Enraf–Nonius, 1985[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The tittle compound is used as an important organic synthesis intermediate. It is used as a sensitizer for thermal recording materials and materials for polyester-resin monomers and fire-resistant materials (Saito et al.,1988). We report herein on the crystal structure of the title compound.

The molecular structure of the title molecule is shown in Fig. 1. The bond lengths (Allen et al., 1987) and angles are within normal ranges. The molecule has two-fold rotational symmetry, the 2-fold axis bisecting bond C8-C8A. The central O2-C8-C8A-O2A torsion angles is 69.45 (16) °. The symmetry related benzene rings [C2-C7 and C2A-C7A; symmetry code (A) -x, y, -z-1/2], are inclined to one another by 64.91 (8) °.

In the crystal, molecules are linked via C—H···O hydrogen bonds forming a three-dimensional network (Fig. 2 and Table 1).

Related literature top

For the synthesis, uses and properties of the title compound, see: Saito et al. (1988). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by a method reported in literature (Saito et al., 1988). To a solution of 1,2-dibromoethane (2.3 g, 12 mmol) and 4-methoxyphenol (3.1 g, 25 mmol) in acetonitrile (100 ml) was added anhydrous potassium carbonate (6.2 g, 45 mmol), and the mixture was stirred overnight at 338 K. The reaction mixture was filtered and the filtrate evaporated under reduced pressure. The residue was subjected to flash chromatography on silica gel, eluting with (10:1/ petroleum ether:ethyl acetate) to give title compound (Yield 2.13 g). Colourless block-like crystals of the title compound were obtained by slow evaporation of a solution in ethanol (20 ml) after about 7 d.

Refinement top

All H atoms were positioned geometrically and constrained to ride on their parent atom: C—H = 0.93 Å (aromatic H), 0.97 Å (CH2), and 0.96 Å (CH3) with Uiso(H) = k × Ueq(C), where k = 1.5 for CH3 H atoms, and = 1.2 for other H atoms.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view along the b axis of the crystal packing of the title compound, showing the C-H···O hydrogen bonds (dashed lines; see Table 1 for details; H atoms not involved in these interactions have been omitted for clarity).
1,2-Bis(4-methoxyphenoxy)ethane top
Crystal data top
C16H18O4F(000) = 584
Mr = 274.32Dx = 1.319 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1571 reflections
a = 26.073 (4) Åθ = 3.2–30.3°
b = 5.5538 (8) ŵ = 0.09 mm1
c = 9.7591 (14) ÅT = 293 K
β = 102.211 (3)°Block, colourless
V = 1381.2 (4) Å30.20 × 0.18 × 0.15 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
976 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 25.5°, θmin = 1.6°
ω/2θ scansh = 3124
Absorption correction: ψ scan
(North et al., 1968)
k = 65
Tmin = 0.981, Tmax = 0.986l = 1111
3780 measured reflections3 standard reflections every 200 reflections
1277 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.224 w = 1/[σ2(Fo2) + (0.168P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
1277 reflectionsΔρmax = 0.26 e Å3
93 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.020 (6)
Crystal data top
C16H18O4V = 1381.2 (4) Å3
Mr = 274.32Z = 4
Monoclinic, C2/cMo Kα radiation
a = 26.073 (4) ŵ = 0.09 mm1
b = 5.5538 (8) ÅT = 293 K
c = 9.7591 (14) Å0.20 × 0.18 × 0.15 mm
β = 102.211 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
976 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.023
Tmin = 0.981, Tmax = 0.9863 standard reflections every 200 reflections
3780 measured reflections intensity decay: 1%
1277 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.224H-atom parameters constrained
S = 1.10Δρmax = 0.26 e Å3
1277 reflectionsΔρmin = 0.29 e Å3
93 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
O10.20123 (6)0.7928 (2)0.33002 (13)0.0496 (5)
O20.02888 (5)0.7020 (2)0.10672 (11)0.0412 (5)
C10.20477 (9)0.9943 (3)0.42124 (19)0.0545 (8)
C20.15790 (7)0.7773 (3)0.22314 (17)0.0332 (6)
C30.15573 (7)0.5837 (3)0.13368 (16)0.0364 (6)
C40.11377 (7)0.5526 (3)0.02195 (16)0.0343 (6)
C50.07272 (7)0.7183 (3)0.00101 (16)0.0316 (5)
C60.07499 (7)0.9113 (3)0.08874 (15)0.0352 (6)
C70.11697 (7)0.9435 (3)0.20009 (16)0.0361 (6)
C80.02601 (7)0.5040 (3)0.20015 (15)0.0369 (6)
H1A0.206401.139500.369000.0820*
H1B0.235900.980700.493800.0820*
H1C0.174500.998800.462500.0820*
H30.183000.472100.148700.0440*
H40.113000.421500.037700.0410*
H60.047701.022300.074000.0420*
H70.117901.075400.259300.0430*
H8A0.030600.354600.147400.0440*
H8B0.053900.515800.251800.0440*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0415 (9)0.0576 (10)0.0417 (9)0.0100 (6)0.0089 (6)0.0100 (6)
O20.0360 (9)0.0484 (9)0.0342 (8)0.0108 (5)0.0037 (6)0.0086 (5)
C10.0498 (13)0.0594 (14)0.0457 (12)0.0018 (9)0.0094 (9)0.0141 (8)
C20.0324 (10)0.0394 (11)0.0261 (9)0.0017 (7)0.0024 (7)0.0032 (6)
C30.0336 (11)0.0408 (11)0.0340 (10)0.0103 (7)0.0052 (7)0.0028 (7)
C40.0373 (11)0.0348 (10)0.0307 (9)0.0061 (7)0.0067 (7)0.0021 (6)
C50.0302 (10)0.0388 (10)0.0250 (8)0.0028 (6)0.0041 (7)0.0024 (6)
C60.0339 (10)0.0355 (10)0.0345 (10)0.0087 (7)0.0037 (8)0.0003 (7)
C70.0393 (11)0.0346 (10)0.0335 (9)0.0039 (7)0.0054 (8)0.0039 (6)
C80.0375 (11)0.0425 (11)0.0286 (9)0.0043 (6)0.0024 (8)0.0033 (6)
Geometric parameters (Å, º) top
O1—C11.421 (2)C8—C8i1.493 (2)
O1—C21.369 (2)C1—H1A0.9600
O2—C51.371 (2)C1—H1B0.9600
O2—C81.4203 (19)C1—H1C0.9600
C2—C31.379 (2)C3—H30.9300
C2—C71.393 (3)C4—H40.9300
C3—C41.382 (2)C6—H60.9300
C4—C51.393 (3)C7—H70.9300
C5—C61.378 (2)C8—H8A0.9700
C6—C71.381 (2)C8—H8B0.9700
C1—O1—C2117.44 (15)H1A—C1—H1B109.00
C5—O2—C8117.16 (13)H1A—C1—H1C110.00
O1—C2—C3116.64 (15)H1B—C1—H1C110.00
O1—C2—C7124.21 (15)C2—C3—H3119.00
C3—C2—C7119.16 (16)C4—C3—H3119.00
C2—C3—C4121.10 (16)C3—C4—H4120.00
C3—C4—C5119.81 (15)C5—C4—H4120.00
O2—C5—C4124.55 (14)C5—C6—H6119.00
O2—C5—C6116.53 (15)C7—C6—H6119.00
C4—C5—C6118.91 (15)C2—C7—H7120.00
C5—C6—C7121.42 (16)C6—C7—H7120.00
C2—C7—C6119.60 (15)O2—C8—H8A110.00
O2—C8—C8i109.61 (14)O2—C8—H8B110.00
O1—C1—H1A109.00H8A—C8—H8B108.00
O1—C1—H1B109.00C8i—C8—H8A110.00
O1—C1—H1C109.00C8i—C8—H8B110.00
C1—O1—C2—C3178.49 (16)C3—C2—C7—C60.2 (3)
C1—O1—C2—C71.2 (2)C2—C3—C4—C50.3 (3)
C8—O2—C5—C41.2 (2)C3—C4—C5—O2178.66 (16)
C8—O2—C5—C6179.96 (15)C3—C4—C5—C60.2 (3)
C5—O2—C8—C8i175.16 (13)O2—C5—C6—C7179.05 (15)
O1—C2—C3—C4179.60 (16)C4—C5—C6—C70.1 (2)
C7—C2—C3—C40.1 (3)C5—C6—C7—C20.3 (3)
O1—C2—C7—C6179.87 (16)O2—C8—C8i—O2i69.45 (16)
Symmetry code: (i) x, y, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O1ii0.962.603.453 (2)148
C6—H6···O2iii0.932.593.490 (2)163
Symmetry codes: (ii) x+1/2, y+3/2, z+1; (iii) x, y+2, z.

Experimental details

Crystal data
Chemical formulaC16H18O4
Mr274.32
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)26.073 (4), 5.5538 (8), 9.7591 (14)
β (°) 102.211 (3)
V3)1381.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.18 × 0.15
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.981, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
3780, 1277, 976
Rint0.023
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.224, 1.10
No. of reflections1277
No. of parameters93
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.29

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O1i0.962.603.453 (2)148
C6—H6···O2ii0.932.593.490 (2)163
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x, y+2, z.
 

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science
First citationEnraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CrossRef CAS IUCr Journals
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science
First citationSaito, T., Kitani, M. & Ishibashi, T. (1988). Jpn Patent No. JP 63156731.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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COMMUNICATIONS
ISSN: 2056-9890
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