[Journal logo]

Volume 68 
Part 7 
Pages o2272-o2273  
July 2012  

Received 14 June 2012
Accepted 26 June 2012
Online 30 June 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.100
Data-to-parameter ratio = 14.4
Details
Open access

1,6-Bis[(2,2':6',2''-terpyridin-4'-yl)oxy]hexane

aUniversity of KwaZulu-Natal, School of Chemistry and Physics, Private Bag X01, Scottsville 3209, Pietermaritzburg, South Africa
Correspondence e-mail: 207513620@stu.ukzn.ac.za

The molecule of the title compound, C36H32N6O2, lies about an inversion center, located at the mid-point of the central C-C bond of the diether bridge. The terminal pyridine rings form dihedral angles of 4.67 (7) and 26.23 (7)° with the central ring. In the crystal, weak C-H...N and C-H...O interactions link the molecules into a three-dimensional network.

Related literature

For the structure of the unsubstituted 2,2':6',2"-terpyridine, see: Bessel et al. (1992[Bessel, C. A., See, R. F., Jameson, D. L., Churchill, M. R. & Takeuchi, K. J. (1992). J. Chem. Soc. Dalton Trans. pp. 3223-3228.]). For the structure of the precursor to the title compound, 4'-chloro-2,2':6',2"-terpyridine, see: Beves et al. (2006[Beves, J. E., Constable, E. C., Housecroft, C. E., Neuburger, M. & Schaffner, S. (2006). Acta Cryst. E62, o2497-o2498.]). For the structure of the 1,4-bis[(2,2':6',2"-terpyridin-4'-yl)oxy]-butane, see: Akerman et al. (2011[Akerman, M. P., Grimmer, C. D., Nikolayenko, V. I. & Reddy, D. (2011). Acta Cryst. E67, o3478-o3479.]). For a full review of functionalized 2,2':6',2"-terpyridine complexes, see: Fallahpour (2003[Fallahpour, R. A. (2003). Synthesis, 2, 155-184.]); Heller & Schubert (2003[Heller, M. & Schubert, U. S. (2003). Eur. J. Org. Chem. 6, 947-961.]). For a comprehensive summary of platinum(II) terpyridine complexes, see: Newkome et al. (2008[Newkome, G. R., Eryazici, I. & Moorefield, C. N. (2008). Chem. Rev. 108, 1834-1895.]). For the structure of bis(2,2':6',2"-terpyridyl)ether, see: Constable et al. (1995[Constable, E. C., Thompson, A. M., Harveson, P., Macko, L. & Zehnder, M. (1995). Chem. Eur. J. 1, 360-367.]). For the structure of related bis(terpyridine) compounds, linked by an alkoxy spacer, see: Constable et al. (2006[Constable, E. C., Chow, H. S., Housecroft, C. E., Neuburger, M. & Schaffner, S. (2006). Polyhedron, 25, 1831-1843.]). For the synthetic procedure, see: Constable et al. (2005[Constable, E. C., Housecroft, C. E., Neuburger, M., Schaffner, S. & Smith, C. B. (2005). Dalton Trans. pp. 2259-2267.]); Van der Schilden (2006[Van der Schilden, K. (2006). PhD thesis, Leiden University, The Netherlands.]).

[Scheme 1]

Experimental

Crystal data
  • C36H32N6O2

  • Mr = 580.7

  • Orthorhombic, P b c a

  • a = 15.139 (5) Å

  • b = 11.428 (5) Å

  • c = 16.760 (5) Å

  • V = 2899.6 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.40 × 0.20 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur 2 CCD diffractometer

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.967, Tmax = 0.983

  • 20354 measured reflections

  • 2859 independent reflections

  • 2098 reflections with I > 2[sigma](I)

  • Rint = 0.064

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.100

  • S = 0.94

  • 2859 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Short intermolecular contacts (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15...Oi 0.95 2.65 3.575 (2) 164
C1-H1...N3ii 0.95 2.71 3.654 (2) 174
C4-H4...N1iii 0.95 2.65 3.402 (2) 136
C2-H2...Oii 0.95 2.69 3.627 (2) 168
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); 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, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2063 ).


Acknowledgements

We wish to thank the Univeristy of Kwazulu-Natal for supporting this research by providing both funding and facilities.

References

Akerman, M. P., Grimmer, C. D., Nikolayenko, V. I. & Reddy, D. (2011). Acta Cryst. E67, o3478-o3479.  [CrossRef] [details]
Bessel, C. A., See, R. F., Jameson, D. L., Churchill, M. R. & Takeuchi, K. J. (1992). J. Chem. Soc. Dalton Trans. pp. 3223-3228.  [CrossRef]
Beves, J. E., Constable, E. C., Housecroft, C. E., Neuburger, M. & Schaffner, S. (2006). Acta Cryst. E62, o2497-o2498.  [CSD] [CrossRef] [details]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Constable, E. C., Chow, H. S., Housecroft, C. E., Neuburger, M. & Schaffner, S. (2006). Polyhedron, 25, 1831-1843.
Constable, E. C., Housecroft, C. E., Neuburger, M., Schaffner, S. & Smith, C. B. (2005). Dalton Trans. pp. 2259-2267.  [CSD] [CrossRef]
Constable, E. C., Thompson, A. M., Harveson, P., Macko, L. & Zehnder, M. (1995). Chem. Eur. J. 1, 360-367.  [CrossRef] [ChemPort]
Fallahpour, R. A. (2003). Synthesis, 2, 155-184.  [CrossRef]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Heller, M. & Schubert, U. S. (2003). Eur. J. Org. Chem. 6, 947-961.  [CrossRef]
Newkome, G. R., Eryazici, I. & Moorefield, C. N. (2008). Chem. Rev. 108, 1834-1895.  [ISI] [PubMed]
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Van der Schilden, K. (2006). PhD thesis, Leiden University, The Netherlands.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o2272-o2273   [ doi:10.1107/S1600536812029017 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.