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Volume 64 
Part 10 
Page o2001  
October 2008  

Received 14 August 2008
Accepted 19 September 2008
Online 24 September 2008

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Key indicators
Single-crystal Synchrotron study
T = 120 K
Mean [sigma](C-C) = 0.014 Å
R = 0.099
wR = 0.294
Data-to-parameter ratio = 7.6
Details
Open access

Dibenzo-18-crown-6

Geraldo M. de Lima,a James L. Wardella and William T. A. Harrisonb*

aDepartamento de Quimica, Universidade Federal de Minas Gerais, UFMG, Avenida Antônio Carlos 6627, Belo Horizonte, MG, CEP 31270-901, Brazil, and bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
Correspondence e-mail: w.harrison@abdn.ac.uk

The asymmetric unit of the title compound, C20H24O6, contains two molecules that are identical within standard deviations concerning bond lengths and angles as well as their conformations. In the crystal structure, weak C-H...O interactions help to consolidate the packing.

Related literature

For background, see: Hutton & Oakes (1976[Hutton, R. E. & Oakes, V. (1976). Adv. Chem. Ser. 157, 113-122.]); Baur & Kassner (1992[Baur, W. H. & Kassner, D. (1992). Acta Cryst. B48, 356-369.]); Grotjahn et al. (2001[Grotjahn, M., Lehmann, S., Aurich, J. & Kleinpeter, E. (2001). J. Phys. Org. Chem. 14, 43-51.]); Barranikov et al. (2002[Barranikov, V. P., Guseinov, S. S. & V'ugin, A. I. (2002). Russ. J. Coord. Chem. 28, 153-162.]); Su et al. (2003[Su, C. C., Lu, L. H. & Liu, L. K. (2003). J. Phys. Chem. A, 107, 4563-4567.]). 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. 1, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C20H24O6

  • Mr = 360.39

  • Monoclinic, C c

  • a = 4.902 (3) Å

  • b = 28.58 (2) Å

  • c = 25.06 (2) Å

  • [beta] = 92.049 (8)°

  • V = 3509 (4) Å3

  • Z = 8

  • Synchrotron radiation

  • [lambda] = 0.6946 Å

  • [mu] = 0.10 mm-1

  • T = 120 (2) K

  • 0.04 × 0.02 × 0.02 mm
Data collection

  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: none

  • 13644 measured reflections

  • 3564 independent reflections

  • 2972 reflections with I > 2[sigma](I)

  • Rint = 0.054
Refinement

  • R[F2 > 2[sigma](F2)] = 0.098

  • wR(F2) = 0.294

  • S = 1.15

  • 3564 reflections

  • 470 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.50 e Å-3

  • [Delta][rho]min = -0.52 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C16-H16...O8i 0.95 2.57 3.46 (1) 157
C26-H26...O5ii 0.95 2.54 3.42 (1) 155
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2081 ).

Acknowledgements

We thank Professor Bill Clegg (University of Newcastle/Daresbury Laboratory) for collecting the diffraction data and performing the initial processing.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 1, pp. S1-19.
Barranikov, V. P., Guseinov, S. S. & V'ugin, A. I. (2002). Russ. J. Coord. Chem. 28, 153-162.
Baur, W. H. & Kassner, D. (1992). Acta Cryst. B48, 356-369.  [CrossRef] [ISI] [details]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Grotjahn, M., Lehmann, S., Aurich, J. & Kleinpeter, E. (2001). J. Phys. Org. Chem. 14, 43-51.  [CrossRef] [ChemPort]
Hutton, R. E. & Oakes, V. (1976). Adv. Chem. Ser. 157, 113-122.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Su, C. C., Lu, L. H. & Liu, L. K. (2003). J. Phys. Chem. A, 107, 4563-4567.  [CrossRef] [ChemPort]

Acta Cryst (2008). E64, o2001  [ doi:10.1107/S1600536808030250 ]

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