2-Eth­oxy-4-[2-(3-nitro­phen­yl)­hydrazono­meth­yl]phenol

Jun-Qiang Chen; Ling Jiang; Shu-Mian Li; Yu-Zhen Chen

doi:10.1107/S1600536809037908

. 2009 Sep 26;65(Pt 10):o2536. doi: 10.1107/S1600536809037908

2-Ethoxy-4-[2-(3-nitrophenyl)hydrazonomethyl]phenol

Jun-Qiang Chen ^a,^*, Ling Jiang ^b, Shu-Mian Li ^b, Yu-Zhen Chen ^b

PMCID: PMC2970498 PMID: 21577980

Abstract

The title Schiff base compound, C₁₅H₁₅N₃O₄, was prepared from a condensation reaction of 3-ethoxy-4-hydroxybenzaldehyde and 3-nitrophenylhydrazine. The molecule is nearly planar; the dihedral angle between the hydroxybenzene ring and the nitrobenzene ring is 6.57 (7)°. O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonding helps to stabilize the crystal structure.

Related literature

For applications of Schiff base compounds, see: Kahwa et al. (1986 ▶); Santos et al. (2001 ▶).

Experimental

Crystal data

C₁₅H₁₅N₃O₄
M _r = 301.30
Monoclinic,
a = 12.4160 (6) Å
b = 7.7429 (4) Å
c = 16.2249 (9) Å
β = 110.497 (6)°
V = 1461.04 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.20 × 0.16 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.979, T _max = 0.982
5606 measured reflections
2835 independent reflections
1558 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.077
S = 0.80
2835 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037908/xu2611sup1.cif

e-65-o2536-sup1.cif^{(17KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037908/xu2611Isup2.hkl

e-65-o2536-Isup2.hkl^{(139.2KB, 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
O2—H2A⋯O1	0.89 (2)	2.14 (2)	2.6582 (16)	116.7 (18)
O2—H2A⋯N1ⁱ	0.89 (2)	2.32 (2)	3.0345 (19)	137.0 (15)
C11—H11A⋯O2ⁱⁱ	0.93	2.56	3.340 (2)	141

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

supplementary crystallographic information

Comment

The chemistry of Schiff base has attracted a great deal of interest in recent years. These compounds play an important role in the development of various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of our study of the coordination chemistry of Schiff bases, we synthesized the title compound and determined its crystal structure.

The molecular structure of (I) is shown in Fig. 1. The hydroxybenzene ring and the nitrobenzene ring is roughly co-planar, making a dihedral angle of 6.57 (7)°. Intramolecular O—H···O hydrogen bond and intermolecular O—H···N and C—H···O hydrogen bonds are observed (Table 1), they help to stabilize the crystal structure (Fig. 2).

Experimental

2-Nitrophenylhydrazine (1 mmol, 0.153 g) was dissolved in anhydrous ethanol (15 ml). The solution was stirred for several min at 351 K, 3-ethoxy-4-hydroxybenzaldehyde (1 mmol, 0.166 g) in ethanol (8 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The solid product was isolated and recrystallized from methanol, red single crystals were obtained after 3 d.