[Journal logo]

Volume 69 
Part 12 
Pages o1785-o1786  
December 2013  

Received 4 November 2013
Accepted 11 November 2013
Online 20 November 2013

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.004 Å
R = 0.057
wR = 0.174
Data-to-parameter ratio = 20.5
Details
Open access

(E)-N,N-Diethyl-2,6-diisopropyl-4-[2-(4-nitro­phen­yl)ethen­yl]aniline

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

The title compound, C24H32N2O2, was prepared by Horner olefination of 4-di­ethyl­amino-3,5-diiso­propyl­benzaldehyde and diethyl p-nitro­benzyl­phospho­nate. There are two independent mol­ecules (A and B) in the asymmetric unit. Their main axes, defined by the line connecting the N atoms of the nitro and amino groups, open an angle of 79.42 (3)°. Steric hindrance around the amino group is reflected in a long aryl C-N bond [1.434 (3) Å for mol­ecule A and 1.440 (3) Å for mol­ecule B], a pyramidal geometry [angle sum = 350.0 (2)° for mol­ecule A and 349.6 (2)° for mol­ecule B], and dihedral angles between the phenyl­ene group and the plane defined by the CH2-N-CH2 unit of 86.9 (3)° for mol­ecule A and 88.3 (3)° for mol­ecule B. This gives structural support for the electronic decoupling of the amino group from the nearly planar nitro­stilbene moiety (r.m.s. deviation for C, N and O atoms = 0.097 for mol­ecule A and 0.107 Å for mol­ecule B).

Related literature

For the synthesis of amino­nitro­stilbenes, see: Pfeiffer et al. (1915[Pfeiffer, P., Braude, S., Kleber, J., Marcon, G. & Wittkop, P. (1915). Ber. Dtsch Chem. Ges. 48, 1777-1809.]); Meier et al. (2004[Meier, H., Gerold, J., Kolshorn, H. & Muehling, B. (2004). Chem. Eur. J. 10, 360-370.]). For torsion-depent optical properties, see: Baumann et al. (1977[Baumann, W., Deckers, H., Loosen, K. D. & Petzke, F. (1977). Ber. Bunsen Ges. Phys. Chem. 81, 799-804.]); Wink & Detert (2013[Wink, C. & Detert, H. (2013). J. Phys. Org. Chem. 26, 137-143.]); Dekhtyar & Rettig (2007[Dekhtyar, M. & Rettig, W. (2007). J. Phys. Chem. A, 111, 2035-2039.]). For conjugated oligomers as sensing materials, see: Schmitt et al. (2008[Schmitt, V., Glang, S., Preis, J. & Detert, H. (2008). Sens. Lett. 6, 1-7.]); Zucchero et al. (2009[Zucchero, A. J., Tolosa, J., Tolbert, L. M. & Bunz, U. H. F. (2009). Chem. Eur. J. 15, 13075-13081.]). For the structures of donor-acceptor stilbenoid dyes, see: Schollmeyer & Detert (2011[Schollmeyer, D. & Detert, H. (2011). Acta Cryst. E67, o1384-o1385.]); Fischer et al. (2011[Fischer, J., Schmitt, V., Schollmeyer, D. & Detert, H. (2011). Acta Cryst. E67, o875.]). For structures of sterically crowded push-pull analogues, see: Wink & Detert (2013[Wink, C. & Detert, H. (2013). J. Phys. Org. Chem. 26, 137-143.]). For the synthesis of the starting materiel, see: Wink et al. (2011[Wink, C., Schollmeyer, D. & Detert, H. (2011). Acta Cryst. E67, o3336.]). 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.]); Schmitt et al. (2013[Schmitt, V., Moschel, S. & Detert, H. (2013). Eur. J. Org. Chem. 25, 5655-5669.]); Nemkovich et al. (2010[Nemkovich, N. A., Detert, H. & Schmitt, V. (2010). Chem. Phys. 378, 37-41.]).

[Scheme 1]

Experimental

Crystal data
  • C24H32N2O2

  • Mr = 380.52

  • Triclinic, [P \overline 1]

  • a = 7.3477 (7) Å

  • b = 15.4143 (14) Å

  • c = 20.3747 (19) Å

  • [alpha] = 104.642 (8)°

  • [beta] = 92.414 (8)°

  • [gamma] = 90.793 (7)°

  • V = 2230.0 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 193 K

  • 0.60 × 0.10 × 0.05 mm

Data collection
  • Stoe IPDS 2T diffractometer

  • 21656 measured reflections

  • 10640 independent reflections

  • 3887 reflections with I > 2[sigma](I)

  • Rint = 0.086

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.174

  • S = 0.79

  • 10640 reflections

  • 518 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Data collection: X-AREA (Stoe & Cie, 2011[Stoe & Cie (2011). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2011[Stoe & Cie (2011). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]); 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: BT6943 ).


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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Baumann, W., Deckers, H., Loosen, K. D. & Petzke, F. (1977). Ber. Bunsen Ges. Phys. Chem. 81, 799-804.  [CrossRef] [ChemPort]
Dekhtyar, M. & Rettig, W. (2007). J. Phys. Chem. A, 111, 2035-2039.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Detert, H. & Sugiono, E. (2005). J. Lumin. 112, 372-376.  [Web of Science] [CrossRef] [ChemPort]
Fischer, J., Schmitt, V., Schollmeyer, D. & Detert, H. (2011). Acta Cryst. E67, o875.  [CSD] [CrossRef] [IUCr Journals]
Meier, H., Gerold, J., Kolshorn, H. & Muehling, B. (2004). Chem. Eur. J. 10, 360-370.  [CrossRef] [PubMed] [ChemPort]
Nemkovich, N. A., Detert, H. & Schmitt, V. (2010). Chem. Phys. 378, 37-41.  [Web of Science] [CrossRef] [ChemPort]
Pfeiffer, P., Braude, S., Kleber, J., Marcon, G. & Wittkop, P. (1915). Ber. Dtsch Chem. Ges. 48, 1777-1809.  [CrossRef] [ChemPort]
Schmitt, V., Glang, S., Preis, J. & Detert, H. (2008). Sens. Lett. 6, 1-7.  [CrossRef]
Schmitt, V., Moschel, S. & Detert, H. (2013). Eur. J. Org. Chem. 25, 5655-5669.  [CSD] [CrossRef]
Schollmeyer, D. & Detert, H. (2011). Acta Cryst. E67, o1384-o1385.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (2011). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.
Wink, C. & Detert, H. (2013). J. Phys. Org. Chem. 26, 137-143.  [CrossRef]
Wink, C., Schollmeyer, D. & Detert, H. (2011). Acta Cryst. E67, o3336.  [CSD] [CrossRef] [IUCr Journals]
Zucchero, A. J., Tolosa, J., Tolbert, L. M. & Bunz, U. H. F. (2009). Chem. Eur. J. 15, 13075-13081.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1785-o1786   [ doi:10.1107/S1600536813030948 ]

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.