[Journal logo]

Volume 67 
Part 6 
Pages o1384-o1385  
June 2011  

Received 2 May 2011
Accepted 3 May 2011
Online 11 May 2011

[bt5539sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.082
wR = 0.239
Data-to-parameter ratio = 20.7
Details
Open access

N,N-Dihexyl-4-[2-(4-nitrophenyl)vinyl]aniline

Dieter Schollmeyera and Heiner Deterta*

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

The title compound, C26H36N2O2, was prepared by Horner olefination of p-dihexylaminobenzaldehyde and diethyl p-nitrobenzylphosphonate. It crystallizes with two independent molecules in the asymmetric unit. Both have similar geometries of the [pi]-systems but the conformations of all hexyl chains are different. Whereas one hexyl chain of the first molecule shows the typical all-anti conformation, the second is arranged in a gauche-anti-gauche-anti conformation with N-C-C-C, C-C-C-C, C-C-C-C and C-C-C-C torsion angles of -65.1 (4), 167.3 (3), 63.3 (4), and 179.4 (3)°. One of the hexyl chains in the other molecule has an anti-anti-gauche-anti conformation [N-C-C-C, C-C-C-C, C-C-C-C and C-C-C-C torsion angles = 179.6 (3), -179.8 (3), -68.7 (5) and -178.8 (4)°], the other starts with an anti-gauche-gauche sequence. Molecules A and B are composed of five planar subunits. The angle sums around the N atoms are in the range 356 (2)-360.0 (2)°. Torsion angles between these segments do not exceed 4.9 (4)°, except for one of the alkyl chains each [molecule A = 26.2 (4)°; molecule B = -6.0 (4)°]. The high planarity of the molecules and the short aniline C-N bonds [1.385 (3) Å in molecule A and 1.378 (3) Å in molecule B] indicate a strong electronic coupling through the stilbene unit. One methylene group is disordered over two positions with an occupancy ratio of 0.72:0.28.

Related literature

For chromophores and fluorophores based on quadrupolar donor-acceptor-substituted stilbenoid systems, see: Detert & Sugiono (2005[Detert, H. & Sugiono, E. (2005). J. Lumin. 112, 372-376.]); 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.]). Similar aminonitrostilbenes had been prepared earlier, see: Pfeiffer et al. (1915[Pfeiffer, P., Braude, S., Kleber, J., Marcon, G. & Wittkop, P. (1915). Ber. Dtsch Chem. Ges. 48, 1777-809.]); Chardonnens & Heinrich (1939[Chardonnens, L. & Heinrich, P. (1939). Helv. Chim. Acta, 22, 1471-82.]); Meier et al. (2004[Meier, H., Gerold, J., Kolshorn, H. & Muehling, B. (2004). Chem. Eur. J. 10, 360-370.]). The optical properties of these dyes are strongly dependent on charge transfer and torsion angles, see: Baumann et al. (1977[Baumann, W., Deckers, H., Loosen, K. D. & Petzke, F. (1977). Ber. Bunsen Ges. Phys. Chem. 81, 799-804.]); Goerner (1998[Goerner, H. (1998). Ber. Bunsen Ges. Phys. Chem. 102, 726-737.]); Dekhtyar & Rettig (2007[Dekhtyar, M. & Rettig, W. (2007). J. Phys. Chem. A, 111, 2035-2039.]). Conjugated oligomers with basic sites are sensing materials for polarity and cations, see: 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 a comparable compound, see: Fischer et al. (2011[Fischer, J., Schmitt, V., Schollmeyer, D. & Detert, H. (2011). Acta Cryst. E67, o875.]).

[Scheme 1]

Experimental

Crystal data

  • C26H36N2O2

  • Mr = 408.57

  • Triclinic, [P \overline 1]

  • a = 9.6574 (9) Å

  • b = 11.4153 (10) Å

  • c = 23.604 (2) Å

  • [alpha] = 93.297 (3)°

  • [beta] = 94.834 (3)°

  • [gamma] = 112.696 (3)°

  • V = 2380.6 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 173 K

  • 0.54 × 0.37 × 0.06 mm
Data collection

  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (PLATON; Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) Tmin = 0.936, Tmax = 0.996

  • 90478 measured reflections

  • 11464 independent reflections

  • 7228 reflections with I > 2[sigma](I)

  • Rint = 0.062
Refinement

  • R[F2 > 2[sigma](F2)] = 0.082

  • wR(F2) = 0.239

  • S = 1.02

  • 11464 reflections

  • 553 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.76 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: BT5539 ).

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]
Baumann, W., Deckers, H., Loosen, K. D. & Petzke, F. (1977). Ber. Bunsen Ges. Phys. Chem. 81, 799-804.  [ChemPort]
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chardonnens, L. & Heinrich, P. (1939). Helv. Chim. Acta, 22, 1471-82.  [ChemPort]
Dekhtyar, M. & Rettig, W. (2007). J. Phys. Chem. A, 111, 2035-2039.  [ISI] [PubMed] [ChemPort]
Detert, H. & Sugiono, E. (2005). J. Lumin. 112, 372-376.  [ChemPort]
Fischer, J., Schmitt, V., Schollmeyer, D. & Detert, H. (2011). Acta Cryst. E67, o875.  [CSD] [CrossRef] [details]
Goerner, H. (1998). Ber. Bunsen Ges. Phys. Chem. 102, 726-737.  [ChemPort]
Meier, H., Gerold, J., Kolshorn, H. & Muehling, B. (2004). Chem. Eur. J. 10, 360-370.  [ChemPort]
Nemkovich, N. A., Detert, H. & Schmitt, V. (2010). Chem. Phys. 378, 37-41.  [ChemPort]
Pfeiffer, P., Braude, S., Kleber, J., Marcon, G. & Wittkop, P. (1915). Ber. Dtsch Chem. Ges. 48, 1777-809.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
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]
Zucchero, A. J., Tolosa, J., Tolbert, L. M. & Bunz, U. H. F. (2009). Chem. Eur. J. 15, 13075-13081.  [ChemPort]

Acta Cryst (2011). E67, o1384-o1385   [ doi:10.1107/S1600536811016709 ]

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.