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Volume 69 
Part 1 
Page o22  
January 2013  

Received 21 November 2012
Accepted 30 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.152
Data-to-parameter ratio = 12.2
Details
Open access

2,2'-({4-[(4-Nitrophenyl)diazenyl]phenyl}imino)diethanol

aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10903, Thailand, and bDepartment of Textile Science, Faculty of Agro-Industry, Kasetsart University, Bangkok 10900, Thailand
Correspondence e-mail: fsciska@ku.ac.th

In the title compound, C16H18N4O4, the molecule assumes an E conformation with respect to the N=N double bond. The aromatic rings are not coplanar, with a dihedral angle of 7.51 (8)°. The nitro group is tilted by 4.71 (11)° relative to the attached benzene ring. In the crystal, molecules are connected through O-H...O hydrogen bonds forming a double-stranded chain parallel to the b axis.

Related literature

For the properties of azo disperse dyes, see: Suesat et al. (2011[Suesat, J., Mungmeechai, T., Suwanruji, P., Parasuk, W., Taylor, J. A. & Phillips, D. A. S. (2011). Color Technol. 127, 217-222.]). For the structure of related compounds, see: Zhang et al. (1998[Zhang, D.-C., Ge, L.-Q., Fei, Z.-H., Zhang, Y.-Q. & Yu, K.-B. (1998). Acta Cryst. C54, 1909-1911.]); Adams et al. (2004[Adams, H., Allen, R. W. K., Chin, J., O'Sullivan, B., Styring, P. & Sutton, L. R. (2004). Acta Cryst. E60, o289-o290.]).

[Scheme 1]

Experimental

Crystal data
  • C16H18N4O4

  • Mr = 330.34

  • Monoclinic, P 21 /c

  • a = 19.000 (3) Å

  • b = 7.3502 (16) Å

  • c = 11.0825 (16) Å

  • [beta] = 92.060 (8)°

  • V = 1546.7 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.24 × 0.16 × 0.04 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 7008 measured reflections

  • 2671 independent reflections

  • 1642 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.152

  • S = 0.93

  • 2671 reflections

  • 219 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O4i 0.82 1.90 2.700 (3) 164
O4-H4...O1ii 0.82 1.90 2.718 (3) 172
Symmetry codes: (i) x, y+1, z; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5028 ).


Acknowledgements

The authors thank the Kasetsart University Research and Development Institute and the Department of Chemistry, Faculty of Science, Kasetsart University, for research funds.

References

Adams, H., Allen, R. W. K., Chin, J., O'Sullivan, B., Styring, P. & Sutton, L. R. (2004). Acta Cryst. E60, o289-o290.  [CSD] [CrossRef] [details]
Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Suesat, J., Mungmeechai, T., Suwanruji, P., Parasuk, W., Taylor, J. A. & Phillips, D. A. S. (2011). Color Technol. 127, 217-222.  [CrossRef] [ChemPort]
Zhang, D.-C., Ge, L.-Q., Fei, Z.-H., Zhang, Y.-Q. & Yu, K.-B. (1998). Acta Cryst. C54, 1909-1911.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o22  [ doi:10.1107/S1600536812049239 ]

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