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Volume 69 
Part 9 
Page o1470  
September 2013  

Received 18 August 2013
Accepted 20 August 2013
Online 23 August 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.054
wR = 0.178
Data-to-parameter ratio = 13.6
Details
Open access

4-Ethoxy-N-(4-ethoxyphenyl)-N-(4-nitrophenyl)aniline

aDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, Key Laboratory of Functional Inorganic Materials Chemistry, Hefei 230039, People's Republic of China
Correspondence e-mail: jywu1957@163.com

In the title molecule, C22H22N2O4, the ethoxyphenyl rings are oriented at dihedral angles of 69.31 (13) and 75.90 (13)° to the nitrophenyl ring and are twisted to each other, making a dihedral angle of 78.55 (13)°. In the crystal, weak C-H...O hydrogen bonds and C-H...[pi] interaction link the molecules into a three-dimensional supramolecular architecture.

Related literature

For applications of triphenylamine derivatives, see: Liu et al. (2012[Liu, B., Zhang, Q., Ding, H.-J., Du, Y.-J., Wang, C.-K., Wu, J.-Y., Li, S.-L., Zhou, H.-P., Yang, J.-X. & Tian, Y.-P. (2012). Dyes Pigments, 95, 149-160.]). For related compounds, see: Wang et al. (2011[Wang, X.-M., Jin, F., Chen, Z.-G., Liu, S.-Q., Wang, X.-H., Duan, X.-M., Tao, X.-T. & Jiang, M.-H. (2011). J. Phys. Chem. C, 115, 776-784.]); Gudeika et al. (2012[Gudeika, D., Michaleviciute, A., Lygaitis, R., Grigalevicius, S., Miasojedovas, A., Jursenas, S. & Sini, G. (2012). J. Phys. Chem. C, 116, 14811-14819.]).

[Scheme 1]

Experimental

Crystal data
  • C22H22N2O4

  • Mr = 378.42

  • Monoclinic, P 21 /c

  • a = 10.926 (5) Å

  • b = 18.380 (5) Å

  • c = 10.345 (5) Å

  • [beta] = 107.998 (5)°

  • V = 1975.8 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • 13718 measured reflections

  • 3456 independent reflections

  • 1884 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.178

  • S = 0.98

  • 3456 reflections

  • 255 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C7-C12 benzene ring.

D-H...A D-H H...A D...A D-H...A
C7-H7...O3i 0.93 2.56 3.371 (5) 146
C14-H14B...O4ii 0.96 2.55 3.458 (4) 158
C17-H17...Cg2iii 0.93 2.78 3.700 (4) 173
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y, -z; (iii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5734 ).


Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 21071001), the Education Committee of Anhui Province (grant No. KJ2010A030) and the Natural Science Foundation of Anhui Province (grant No. 1208085MB22).

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Gudeika, D., Michaleviciute, A., Lygaitis, R., Grigalevicius, S., Miasojedovas, A., Jursenas, S. & Sini, G. (2012). J. Phys. Chem. C, 116, 14811-14819.  [CrossRef] [ChemPort]
Liu, B., Zhang, Q., Ding, H.-J., Du, Y.-J., Wang, C.-K., Wu, J.-Y., Li, S.-L., Zhou, H.-P., Yang, J.-X. & Tian, Y.-P. (2012). Dyes Pigments, 95, 149-160.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wang, X.-M., Jin, F., Chen, Z.-G., Liu, S.-Q., Wang, X.-H., Duan, X.-M., Tao, X.-T. & Jiang, M.-H. (2011). J. Phys. Chem. C, 115, 776-784.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1470  [ doi:10.1107/S1600536813023386 ]

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