(E)-2-{N-Ethyl-4-[(4-nitro­phen­yl)diazen­yl]anilino}ethyl acrylate

Mohammad Yousefi; Hossein Hosseini; Vahid Amani; Mansour Arab Chamjangali; Hamid Reza Khavasi

doi:10.1107/S1600536808003085

. 2008 Apr 2;64(Pt 5):o789. doi: 10.1107/S1600536808003085

(E)-2-{N-Ethyl-4-[(4-nitrophenyl)diazenyl]anilino}ethyl acrylate

Mohammad Yousefi ^a,^*, Hossein Hosseini ^b, Vahid Amani ^a, Mansour Arab Chamjangali ^c, Hamid Reza Khavasi ^d

PMCID: PMC2961144 PMID: 21202282

Abstract

In the molecule of the title compound, C₁₉H₂₀N₄O₄, the rings are almost coplanar, forming a dihedral angle of 0.76 (3)°. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules.

Related literature

For related literature, see: Peters & Freeman (1991 ▶); Gregory (1991 ▶); Gur et al. (2007 ▶); Venkataraman (1970 ▶); Srinivasa et al. (2003 ▶). For bond-length data, see: Lacroix et al. (2000 ▶); Gunnlaugsson et al. (2001 ▶).

Experimental

Crystal data

C₁₉H₂₀N₄O₄
M _r = 368.39
Orthorhombic,
a = 8.1518 (9) Å
b = 10.6651 (11) Å
c = 20.6782 (19) Å
V = 1797.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 120 (2) K
0.5 × 0.2 × 0.06 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: numerical [shape of crystal determined optically (X-SHAPE and X-RED; Stoe & Cie, 2005 ▶)] T _min = 0.980, T _max = 0.990
15596 measured reflections
2456 independent reflections
2346 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.079
S = 1.12
2456 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-STEP32 (Stoe & Cie, 2000 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003085/hk2424sup1.cif

e-64-0o789-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003085/hk2424Isup2.hkl

e-64-0o789-Isup2.hkl^{(120.7KB, hkl)}

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
C15—H15A⋯O4ⁱ	0.97	2.40	3.189 (2)	138

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Symmetry code: (i) Inline graphic .

Acknowledgments

We are grateful to the Islamic Azad University, Shahr-e-Rey Branch, and Imam Hossein University for financial support.

supplementary crystallographic information

Comment

It is well known for many years that dyes have been most widely used in fields such as dyeing textile fibers, biomedical studies, advanced applications in organic synthesis and high technology areas like lasers, liquid crystalline displays, electrooptical devices and ink-jet printers (Peters & Freeman, 1991; Gregory 1991; Gur et al., 2007). Azo colorants are the most versatile class of dyes (Venkataraman 1970). They can also be used as indicators in chemical laboratories and as stains in the biological field (Srinivasa et al., 2003). We report herein the synthesis and crystal structure of the title compound, (I).

In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are within normal ranges (Lacroix et al., 2000; Gunnlaugsson et al., 2001). Rings A (C1—C6) and B (C7—C12) are, of course, planar and the dihedral angle between them is 0.76 (3)°, so they are also almost coplanar. The atoms N1, N2, N3, N4, O1 and O2 are at the distances of -0.124 (2) Å, 0.070 (3) Å, -0.016 (2) Å, 0.162 (3) Å, -0.066 (3) Å and -0.255 (2) Å, respectively, to the best plane of the coplanar rings.

In the crystal structure, intermolecular C—H···O hydrogen bonds link the molecules, in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, (I), to a magnetically stirred solution of 4-nitro-4'-[N-ethyl-N-(2-hydroxyethyl)-amino]azobenzene (2.48 mmol) in THF (20 ml), was added dropwise acryloyl chloride (2.48 mmol) in dry nitrogen atmosphere. After 2 h, the mixture was filtered and the desired product was precipitated out by adding water. The solid filtered and washed several times with water, and then dried. The orange precipitated product was recrystallized from ethyl alcohol. After 72 h, orange plate crystals of (I) were isolated (yield; 52.0%, m.p. 397–398 K).