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Volume 69 
Part 8 
Page o1280  
August 2013  

Received 30 June 2013
Accepted 15 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.113
Data-to-parameter ratio = 24.1
Details
Open access

N,N-Diethyl-4-[(E)-(pyridin-3-yl)diazenyl]aniline

aD. Ghitu Institute of Electronic Engineering and Nanotechnologies, 3/3 Academy Street, MD-2028, Chisinau, Republic of Moldova,bDepartment of Chemistry and Biology, New Mexico Highlands University, 803 University Avenue, Las Vegas, NM 87701, USA, and cSaint-Petersburg National Research University of Information Technologies, Mechanics and Optics, Kronverkskiy Prospekt 49, 197101 Saint Petersburg, Russian Federation
Correspondence e-mail: sergiudraguta@gmail.com

The molecule of the title compound, C15H18N4, adopts a trans conformation with respect to the diazo N=N bond. The dihedral angle between the benzene and pyridine rings in the molecule is 8.03 (5)°. In the crystal, a weak C-H...[pi] interaction arranges the molecules into a corrugated ribbon, with an antiparallel orientation of neighboring molecules propagating in the [100] direction.

Related literature

For details of the synthesis, see: Peor et al. (2008[Peor, N., Sfez, R. & Yitzchaik, Sh. (2008). J. Am. Chem. Soc. 130, 4158-4165.]). For nonlinear optical properties of stilbene derivatives, see: Forrest et al. (1996[Forrest, S., Burrows, P., Stroustrup, A., Strickland, D. & Ban, V. (1996). Appl. Phys. Lett. 68, 1326-1332.]). For the comparision of nonlinear optical properties of stilbene and diazo derivatives, see: Chemla & Zyss (1987[Chemla, D. S. & Zyss, J. (1987). Nonlinear Optical Properties of Organic Molecules and Crystals, Vol. 1, pp. 232-277. New York: Academic Press.]); Morley (1995[Morley, J. (1995). J. Chem. Soc. Perkin Trans. 2, pp. 731-738.]). For second-harmonic generation in the P212121 space group, see: Rivera et al. (2006[Rivera, J. M., Reyes, H., Cortés, A., Santillan, R., Lacroix, P. G., Lepetit, C., Nakatani, K. & Farfán, N. (2006). Chem. Mater. 18, 1174-1179.]). For the distribution of endocyclic angles in pyridine derivatives, see: Draguta et al. (2012[Draguta, S., Khrustalev, V. N., Fonari, M. S., Antipin, M. Y. & Timofeeva, T. V. (2012). Acta Cryst. E68, o3353.]).

[Scheme 1]

Experimental

Crystal data
  • C15H18N4

  • Mr = 254.33

  • Orthorhombic, P 21 21 21

  • a = 7.4332 (7) Å

  • b = 9.1093 (8) Å

  • c = 20.1946 (19) Å

  • V = 1367.4 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.977, Tmax = 0.985

  • 16318 measured reflections

  • 4195 independent reflections

  • 4012 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.113

  • S = 1.00

  • 4195 reflections

  • 174 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.62 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of C6-C11 ring.

D-H...A D-H H...A D...A D-H...A
C3-H3...Cgi 0.95 2.60 3.483 (2) 158
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). 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: CV5422 ).


Acknowledgements

The authors are grateful for NSF support via DMR grant Nos. 0934212 (PREM) and CHE 0832622.

References

Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Chemla, D. S. & Zyss, J. (1987). Nonlinear Optical Properties of Organic Molecules and Crystals, Vol. 1, pp. 232-277. New York: Academic Press.
Draguta, S., Khrustalev, V. N., Fonari, M. S., Antipin, M. Y. & Timofeeva, T. V. (2012). Acta Cryst. E68, o3353.  [CSD] [CrossRef] [IUCr Journals]
Forrest, S., Burrows, P., Stroustrup, A., Strickland, D. & Ban, V. (1996). Appl. Phys. Lett. 68, 1326-1332.  [CrossRef] [ChemPort] [Web of Science]
Morley, J. (1995). J. Chem. Soc. Perkin Trans. 2, pp. 731-738.
Peor, N., Sfez, R. & Yitzchaik, Sh. (2008). J. Am. Chem. Soc. 130, 4158-4165.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Rivera, J. M., Reyes, H., Cortés, A., Santillan, R., Lacroix, P. G., Lepetit, C., Nakatani, K. & Farfán, N. (2006). Chem. Mater. 18, 1174-1179.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1280  [ doi:10.1107/S1600536813019545 ]

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