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

Tanwawan Duangthongyou; Potjanart Suwanruji; Jantip Suesat; Supakit Achiwawanich

doi:10.1107/S1600536812049239

. 2012 Dec 5;69(Pt 1):o22. doi: 10.1107/S1600536812049239

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

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

PMCID: PMC3588337 PMID: 23476410

Abstract

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 ▶). For the structure of related compounds, see: Zhang et al. (1998 ▶); Adams et al. (2004 ▶). graphic file with name e-69-00o22-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₈N₄O₄
M _r = 330.34
Monoclinic,
a = 19.000 (3) Å
b = 7.3502 (16) Å
c = 11.0825 (16) Å
β = 92.060 (8)°
V = 1546.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.152
S = 0.93
2671 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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 Material

Click here for additional data file.^{(18.9KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049239/rz5028sup1.cif

e-69-00o22-sup1.cif^{(18.9KB, cif)}

Click here for additional data file.^{(131.2KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049239/rz5028Isup2.hkl

e-69-00o22-Isup2.hkl^{(131.2KB, hkl)}

Click here for additional data file.^{(6.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812049239/rz5028Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

Comment

A series of azo disperse dyes was recently synthesized by our group in order to study the influence of substituents on the chromatic properties of the dyes (Suesat et al., 2011). We report herein the crystal structure of one of these dyes.

The molecule of the title compound (Fig. 1) displays an E configuration about the N═N double bond and is not planar, the dihedral angle between the aromatic ring being 7.51 (8)°. This value may be compared with those observed in the related compounds 4'-(dimethylamino)-2-nitroazobenzene (5.3 (2)°; Zhang et al., 1998) and 4'-(dimethylamino)-4-nitroazobenzene (2.1 (4)°; Adams et al., 2004). The nitro group is tilted by 4.71 (11)° with respect to the attached C7–C11 benzene ring. In the crystal structure, molecules are linked by O—H···O hydrogen bonds (Table 1) to form double-stranded chain parallel to the b axis (Fig. 2).

Experimental

The azo disperse dye was prepared by dissolving 4-nitroaniline (0.01 mol) in 50 ml of an acetic acid/propionic acid (43:7 v/v) mixture. The solution was stirred and the temperature was kept in the range of 0–5°C. Diazotization took place when nitrosyl sulfuric acid (HNO₅S) was added to the solution and stirred at 0–5°C for 30–60 minutes. The coupling component N-bis-β-hydroxyethyl aniline (0.01 mol) was then dissolved in 40 ml acetone, distilled water was added to make the total volume of 200 ml and sulfamic acid (0.5 g) was added. The coupling reaction was performed by slow addition of the diazonium salt solution to the coupling solution at 0–5°C. The reaction continued for 2 h with stirring and was monitored using TLC. On completion of the coupling reaction, the dye precipitate was collected by filtration and dried at room temperature. The dye was purified by recrystallization in n-propanol. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a purified dye solution in n-propanol.