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Volume 69 
Part 4 
Page o547  
April 2013  

Received 12 March 2013
Accepted 13 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.224
Data-to-parameter ratio = 13.7
Details
Open access

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

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

  • [beta] = 102.211 (3)°

  • V = 1381.2 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.20 × 0.18 × 0.15 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] 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 > 2[sigma](I)

  • Rint = 0.023

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

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.224

  • S = 1.10

  • 1277 reflections

  • 93 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2572 ).


Acknowledgements

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

References

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.
Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
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.  [ISI] [CrossRef] [ChemPort] [details]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Saito, T., Kitani, M. & Ishibashi, T. (1988). Jpn Patent No. JP 63156731.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o547  [ doi:10.1107/S1600536813007009 ]

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