2-(4-Meth­oxy­phen­oxy)acetohydrazide

Gang Liu; Jie Gao

doi:10.1107/S160053681202435X

. 2012 May 31;68(Pt 6):o1969. doi: 10.1107/S160053681202435X

2-(4-Methoxyphenoxy)acetohydrazide

Gang Liu ^a,^*, Jie Gao ^a

PMCID: PMC3379517 PMID: 22719715

Abstract

The title compound, C₉H₁₂N₂O₃, was synthesized by the reaction of ethyl 2-(4-methoxyphenoxy)acetate with hydrazine hydrate in ethanol. In the acetohydrazide group, the N—N bond is relatively short [1.413 (2) Å], suggesting some degree of electronic delocalization in the molecule. In the crystal, molecules are linked into sheets lying parallel to the ab plane by N—H⋯N and N—H⋯O hydrogen bonds.

Related literature

For general background to and the biological activity of hydrazides, see: Khattab (2005 ▶); Ozdemir et al. (2009 ▶); Ashiq et al. (2009 ▶); Zhang & Shi (2009 ▶). For related structures, see: Dutkiewicz et al. (2009 ▶); Fun et al. (2009 ▶, 2010a ▶,b ▶, 2011 ▶). graphic file with name e-68-o1969-scheme1.jpg

Experimental

Crystal data

C₉H₁₂N₂O₃
M _r = 196.21
Orthorhombic,
a = 4.0964 (17) Å
b = 6.382 (3) Å
c = 35.608 (14) Å
V = 930.9 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.30 × 0.25 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.969, T _max = 0.981
4782 measured reflections
1631 independent reflections
1503 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.089
S = 0.88
1631 reflections
140 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.09 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 datablock(s) global, I. DOI: 10.1107/S160053681202435X/rk2352sup1.cif

e-68-o1969-sup1.cif^{(15.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202435X/rk2352Isup2.hkl

e-68-o1969-Isup2.hkl^{(80.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681202435X/rk2352Isup3.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
N2—H2A⋯O3ⁱ	0.89 (2)	2.51 (2)	3.155 (2)	130.4 (16)
N1—H1⋯N2ⁱⁱ	0.88 (2)	2.18 (2)	2.984 (2)	152.2 (18)
N2—H2B⋯O3ⁱⁱⁱ	0.91 (2)	2.13 (2)	3.027 (2)	167.5 (18)

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

supplementary crystallographic information

Comment

Hydrazides have been of great interest for many years because they have different biological activities and been used for the synthesis of various heterocyclic compounds (Khattab, 2005; Dutkiewicz et al., 2009; Ozdemir et al., 2009; Ashiq et al., 2009; Zhang & Shi, 2009; Fun et al., 2009, 2010a,b, 2011). In order to search for new hydrazide compounds with higher bioactivity, the title compound, was synthesized. Its molecular and crystal structures were determined. The molecular structure is shown in Fig. 1. In the crystal structure (Fig. 2), molecules are linked into infinite two-dimensional networks by the classical intermolecular N–H···N and N–H···O hydrogen bonds. For parameters of these interactions, see Table 1.

Experimental

The title compound was synthesized by the reaction of 2-(4-methoxyphenoxy)acetate (1 mmol) with hydrazine hydrate 85% (1.1 mmol) in ethanol (15 ml) under reflux conditions (338 K) for 5 h. The solvent was removed and the solid product recrystallized from ethanol. After six days colourless crystals suitable for X-ray diffraction study were obtained.