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Volume 68 
Part 11 
Page o3239  
November 2012  

Received 8 October 2012
Accepted 23 October 2012
Online 31 October 2012

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.045
wR = 0.115
Data-to-parameter ratio = 30.7
Details
Open access

5,7,8,10,11,13,14,16-Octahydro-6,15-(ethanoxyethanoxyethano)-1,4:17,20-dietheno[9,12,6,15]benzodioxadiazacyclodocosine1

Heath A. Barnett,a Frank R. Fronczeka* and Steven F. Watkinsa

aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
Correspondence e-mail: ffroncz@lsu.edu

The title compound, C32H40N2O4, is a 1,10-diaza-18-crown-6 cryptand with an o-terphenyl bridge. In the polyether ring, two adjacent -CH2- groups are disordered with very nearly equal populations of two conformers. The ordered bond lengths are normal, with average C-C = 1.511 (3) Å, C-O = 1.421 (3) Å, and C-N = 1.466 (4) Å. The r.m.s. deviations of the three rings of the terphenyl bridge vary from 0.007 to 0.009 Å and the two rings ortho to one another are twisted by 50.75 (5) and 47.76 (4)° with respect to the third ring. The N...N distance is 5.408 (1) Å.

Related literature

For the synthesis of the title compound, see: Rossa & Vögtle (1981[Rossa, L. & Vögtle, F. (1981). Liebigs Ann. Chem. pp. 459-466.]). For the structure of the NaSCN complex, see: Weber (1981[Weber, G. (1981). Acta Cryst. B37, 1832-1835.]). For a related structure, see: Vögtle et al. (1983[Vögtle, F., Muller, W. M., Puff, H. & Friedrichs, E. (1983). Chem. Ber. 116, 2344-2354.]). For the synthesis of cryptands, see: Dietrich et al. (1969a[Dietrich, B., Lehn, J. M. & Sauvage, J. P. (1969a). Tetrahedron Lett. 34, 2885-2888.],b[Dietrich, B., Lehn, J. M. & Sauvage, J. P. (1969b). Tetrahedron Lett. 34, 2889-2892.]). For a background to guest-host interactions, see: Dunitz et al. (1974[Dunitz, J. D., Dobler, M., Seiler, P. & Phizackerley, R. P. (1974). Acta Cryst. B30, 2733-2738.]); Cram & Trueblood (1981[Cram, D. J. & Trueblood, K. N. (1981). Top. Curr. Chem. 98, 43-106.]); Cram (1988[Cram, D. J. (1988). J. Inclusion Phenom. 6, 397-413.]).

[Scheme 1]

Experimental

Crystal data

  • C32H40N2O4

  • Mr = 516.66

  • Triclinic, [P \overline 1]

  • a = 9.6757 (3) Å

  • b = 12.1582 (4) Å

  • c = 12.5129 (5) Å

  • [alpha] = 88.178 (2)°

  • [beta] = 82.616 (2)°

  • [gamma] = 78.072 (2)°

  • V = 1428.26 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.33 × 0.32 × 0.22 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.975, Tmax = 0.983

  • 10763 measured reflections

  • 10763 independent reflections

  • 5346 reflections with I > 2[sigma](I)
Refinement

  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.115

  • S = 0.81

  • 10763 reflections

  • 351 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS86 (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 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2212 ).

Acknowledgements

The purchase of the diffractometer was made possible by grant No. LEQSF(1999-2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

References

Cram, D. J. (1988). J. Inclusion Phenom. 6, 397-413.  [CrossRef] [ChemPort]
Cram, D. J. & Trueblood, K. N. (1981). Top. Curr. Chem. 98, 43-106.  [CrossRef] [ChemPort]
Dietrich, B., Lehn, J. M. & Sauvage, J. P. (1969a). Tetrahedron Lett. 34, 2885-2888.  [CrossRef]
Dietrich, B., Lehn, J. M. & Sauvage, J. P. (1969b). Tetrahedron Lett. 34, 2889-2892.  [CrossRef]
Dunitz, J. D., Dobler, M., Seiler, P. & Phizackerley, R. P. (1974). Acta Cryst. B30, 2733-2738.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Rossa, L. & Vögtle, F. (1981). Liebigs Ann. Chem. pp. 459-466.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Vögtle, F., Muller, W. M., Puff, H. & Friedrichs, E. (1983). Chem. Ber. 116, 2344-2354.
Weber, G. (1981). Acta Cryst. B37, 1832-1835.  [CrossRef] [details]

Acta Cryst (2012). E68, o3239  [ doi:10.1107/S1600536812044017 ]

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