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Volume 67 
Part 4 
Page o876  
April 2011  

Received 8 March 2011
Accepted 9 March 2011
Online 12 March 2011

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.004 Å
R = 0.074
wR = 0.232
Data-to-parameter ratio = 15.6
Details
Open access

2,5-Bis{2,2-bis[4-(dimethylamino)phenyl]ethenyl}-N,N'-diphenyl-N,N'-dipropylbenzene-1,4-diamine

aUniversity Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
Correspondence e-mail: detert@uni-mainz.de

The title compound, C60H68N6, was prepared by Horner olefination of a terephthaldialdehyde and a diarylmethyl phosphonate. There is one half-molecule, located on an inversion centre, in the asymmetric unit. The dihedral angle between the plane of the vinylene unit and the central ring is 36.79 (15)°, while those between the vinylene unit and the lateral phenyl rings are 53.04 (10) and 53.74 (9)°.

Related literature

For conjugated oligomers with basic sites as sensing materials for polarity and cations, see: Detert & Sugiono (2004[Detert, H. & Sugiono, E. (2004). Synth. Met. 147, 233-236.], 2005[Detert, H. & Sugiono, E. (2005). J. Lumin. 112, 372-376.]); Wilson & Bunz (2005[Wilson, J. N. & Bunz, U. H. F. (2005). J. Am. Chem. Soc. 127, 4124-4125.]); Zucchero et al. (2009[Zucchero, A. J., Tolosa, J., Tolbert, L. M. & Bunz, U. H. F. (2009). Chem. Eur. J. 15, 13075-13081.]). For typical synthetic approaches to larger stilbenoid dyes, see: Drefahl & Plötner (1961[Drefahl, G. & Plötner, G. (1961). Chem. Ber. 94, 907-914.]); Stalmach et al. (1996[Stalmach, U., Kolshorn, H., Brehm, I. & Meier, H. (1996). Liebigs Ann. pp. 1449-1456.]). For crystal structures of phenylenevinylene oligomers, see: van Hutten et al. (1999[Hutten, P. F. van, Wildeman, J., Meetsma, A. & Hadziioannou, G. (1999). J. Am. Chem. Soc. 121, 5910-5918.]); Detert et al. (2001[Detert, H., Schollmeyer, D. & Sugiono, E. (2001). Eur. J. Org. Chem. pp. 2927-2938.]). For optical properties of dyes which are highly sensitive towards environmental changes, see: Detert et al. (2001[Detert, H., Schollmeyer, D. & Sugiono, E. (2001). Eur. J. Org. Chem. pp. 2927-2938.]); Strehmel et al. (2003[Strehmel, B., Sarker, A. M. & Detert, H. (2003). ChemPhysChem, 4, 249-259.]); Nemkovich et al. (2010[Nemkovich, N. A., Detert, H. & Schmitt, V. (2010). Chem. Phys. 378, 37-41.]). For the synthesis of the title compound, see: Schmitt (2005[Schmitt, V. (2005). Diploma thesis, University of Mainz, Mainz, Germany.]); Zheng et al. (2003[Zheng, S., Barlow, S., Parker, T. C. & Marder, S. R. (2003). Tetrahedron Lett. 44, 7989-7992.]).

[Scheme 1]

Experimental

Crystal data
  • C60H68N6

  • Mr = 873.20

  • Monoclinic, C 2/c

  • a = 20.485 (9) Å

  • b = 12.0782 (16) Å

  • c = 21.108 (9) Å

  • [beta] = 107.60 (2)°

  • V = 4978 (3) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.52 mm-1

  • T = 193 K

  • 0.50 × 0.30 × 0.20 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • 4859 measured reflections

  • 4720 independent reflections

  • 3352 reflections with I > 2[sigma](I)

  • Rint = 0.064

  • 3 standard reflections every 60 min intensity decay: 2%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.074

  • wR(F2) = 0.232

  • S = 1.09

  • 4720 reflections

  • 303 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971[Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5488 ).


Acknowledgements

Financial support from the Deutsche Forschungsgemeinschaft is gratefully acknowledged.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Detert, H., Schollmeyer, D. & Sugiono, E. (2001). Eur. J. Org. Chem. pp. 2927-2938.
Detert, H. & Sugiono, E. (2004). Synth. Met. 147, 233-236.
Detert, H. & Sugiono, E. (2005). J. Lumin. 112, 372-376.  [ChemPort]
Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.
Drefahl, G. & Plötner, G. (1961). Chem. Ber. 94, 907-914.  [ChemPort]
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Hutten, P. F. van, Wildeman, J., Meetsma, A. & Hadziioannou, G. (1999). J. Am. Chem. Soc. 121, 5910-5918.
Nemkovich, N. A., Detert, H. & Schmitt, V. (2010). Chem. Phys. 378, 37-41.  [ChemPort]
Schmitt, V. (2005). Diploma thesis, University of Mainz, Mainz, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stalmach, U., Kolshorn, H., Brehm, I. & Meier, H. (1996). Liebigs Ann. pp. 1449-1456.
Strehmel, B., Sarker, A. M. & Detert, H. (2003). ChemPhysChem, 4, 249-259.  [ISI] [PubMed] [ChemPort]
Wilson, J. N. & Bunz, U. H. F. (2005). J. Am. Chem. Soc. 127, 4124-4125.  [ISI] [PubMed] [ChemPort]
Zheng, S., Barlow, S., Parker, T. C. & Marder, S. R. (2003). Tetrahedron Lett. 44, 7989-7992.  [ChemPort]
Zucchero, A. J., Tolosa, J., Tolbert, L. M. & Bunz, U. H. F. (2009). Chem. Eur. J. 15, 13075-13081.  [ChemPort]


Acta Cryst (2011). E67, o876  [ doi:10.1107/S160053681100910X ]

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