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

Duangthongyou, T.; Suwanruji, P.; Suesat, J.; Achiwawanich, S.

doi:10.1107/S1600536812049239

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 (C-C) = 0.003 Å
R = 0.044
wR = 0.152
Data-to-parameter ratio = 12.2
Details

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

Tanwawan Duangthongyou,^a Potjanart Suwanruji,^a Jantip Suesat ^b and Supakit Achiwawanich ^a ^*

^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-HO 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). For the structure of related compounds, see: Zhang et al. (1998); Adams et al. (2004).

Experimental

Crystal data

C₁₆H₁₈N₄O₄
M_r = 330.34
Monoclinic, P 2₁ /c
a = 19.000 (3) Å
b = 7.3502 (16) Å
c = 11.0825 (16) Å
= 92.060 (8)°
V = 1546.7 (5) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.152
S = 0.93
2671 reflections
219 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O4ⁱ	0.82	1.90	2.700 (3)	164
O4-H4O1ⁱⁱ	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); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Suesat, J., Mungmeechai, T., Suwanruji, P., Parasuk, W., Taylor, J. A. & Phillips, D. A. S. (2011). Color Technol. 127, 217-222.
Zhang, D.-C., Ge, L.-Q., Fei, Z.-H., Zhang, Y.-Q. & Yu, K.-B. (1998). Acta Cryst. C54, 1909-1911.

organic compounds