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Volume 70 
Part 5 
Page o617  
May 2014  

Received 10 April 2014
Accepted 24 April 2014
Online 30 April 2014

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.077
wR = 0.316
Data-to-parameter ratio = 15.3
Details
Open access

1,6-Bis(p-tol­yloxy)hexa­ne

aHigh Technology Research Institute of Nanjing University, Changzhou 213162, Jiangsu, People's Republic of China, and bSchool of Petrochemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, People's Republic of China
Correspondence e-mail: wkcoool@163.com

The title compound, C20H26O2, crystallized with one half-mol­ecule in the asymmetric unit. The whole mol­ecule is generated by inversion symmetry, with the center of inversion being situated at the mid-point of the central -CH2-CH2- bond of the bridging hexane chain. In the crystal, mol­ecules stack in columns along the b axis. C-H...[pi] inter­actions are present within the columns.

Related literature

For the properties and synthesis of the title compound, see: Saito et al. (1988[Saito, T., Kitani, M. & Ishibashi, T. (1988). 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
  • C20H26O2

  • Mr = 298.41

  • Monoclinic, P 21 /c

  • a = 18.932 (12) Å

  • b = 7.327 (4) Å

  • c = 6.352 (4) Å

  • [beta] = 91.000 (13)°

  • V = 881.0 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 293 K

  • 0.25 × 0.20 × 0.18 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 = 0.983, Tmax = 0.987

  • 4572 measured reflections

  • 1544 independent reflections

  • 963 reflections with I > 2[sigma](I)

  • Rint = 0.117

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

Refinement
  • R[F2 > 2[sigma](F2)] = 0.077

  • wR(F2) = 0.316

  • S = 1.10

  • 1544 reflections

  • 101 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2-C7 benzene ring.

D-H...A D-H H...A D...A D-H...A
C4-H4...Cgi 0.93 2.95 3.696 (4) 138
C7-H7...Cgii 0.93 2.84 3.572 (4) 137
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].

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.]); software used to prepare material for publication: SHELXTL.


Supporting information for this paper is available from the IUCr electronic archives (Reference: SU2725 ).


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.  [CrossRef]
Enraf-Nonius (1985). CAD-4 Software. 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.  [CrossRef] [IUCr Journals]
Saito, T., Kitani, M. & Ishibashi, T. (1988). Patent No. JP 63156731.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o617  [ doi:10.1107/S1600536814009222 ]

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