(E)-Methyl N′-[1-(4-hydroxy­phen­yl)ethyl­idene]hydrazinecarboxyl­ate

Lu-Ping Lv; Jian-Wu Xie; Wen-Bo Yu; Wei-Wei Li; Xian-Chao Hu

doi:10.1107/S1600536808024227

. 2008 Aug 6;64(Pt 9):o1675. doi: 10.1107/S1600536808024227

(E)-Methyl N′-[1-(4-hydroxyphenyl)ethylidene]hydrazinecarboxylate

Lu-Ping Lv ^a, Jian-Wu Xie ^a, Wen-Bo Yu ^a, Wei-Wei Li ^a, Xian-Chao Hu ^b,^*

PMCID: PMC2960493 PMID: 21201665

Abstract

The title compound, C₁₀H₁₂N₂O₃, adopts a trans configuration with respect to the C=N bond. The dihedral angle between the benzene ring and the hydrazine carboxylic acid plane is 8.29 (7)°. Molecules are linked into a three-dimensional network by N—H⋯O, O—H⋯O, O—H⋯N hydrogen bonds and C—H⋯π interactions.

Related literature

For general background, see: Parashar et al. (1988 ▶); Hadjoudis et al. (1987 ▶); Borg et al. (1999 ▶). For related structures, see: Shang et al. (2007 ▶).

Experimental

Crystal data

C₁₀H₁₂N₂O₃
M _r = 208.22
Orthorhombic,
a = 11.2532 (18) Å
b = 10.4310 (17) Å
c = 17.226 (3) Å
V = 2022.1 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 (2) K
0.31 × 0.27 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.972, T _max = 0.978
12287 measured reflections
1794 independent reflections
1626 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.098
S = 1.09
1794 reflections
140 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024227/bg2200sup1.cif

e-64-o1675-sup1.cif^{(16.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024227/bg2200Isup2.hkl

e-64-o1675-Isup2.hkl^{(86.6KB, 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
O1—H1⋯O21ⁱ	0.82	2.61	3.0523 (14)	116
O1—H1⋯N1ⁱ	0.82	2.03	2.8464 (14)	174
N2—H2A⋯O2ⁱⁱ	0.86	2.44	3.2777 (16)	164
C10—H10B⋯Cg1ⁱⁱⁱ	0.96	2.90	3.7169 (19)	144

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 ring.

Acknowledgments

The authors acknowledge financial support from Hangzhou Vocational and Technical College, China.

supplementary crystallographic information

Comment

Benzaldehydehydrazone derivatives have received considerable attentions for a long time due to their pharmacological activity (Parashar et al., 1988) and their photochromic properties(Hadjoudis et al., 1987). Meanwhile, it is an important intermediate of 1,3,4-oxadiazoles, which have been reported to be versatile compounds with interesting properties (Borg et al., 1999). As a further investigation of this type of derivatives, the crystal structure of the title compound, C₁₀H₁₂N₂O₃(Fig.1), is described here.

The title molecule (Fig.1) adopts a trans configuration with respect to the C═N bond. The N1/N2/O2/O3/C9/C10 plane of the hydrazine carboxylic acid methyl ester group is slightly twisted away from the attached ring, to which it subtends a dihedral angle of 8.29 (7)°. Bond lengths and angles agree with those observed for methyl N'-[(E)-4-methoxybenzylidene] hydrazinecarboxylate (Shang et al., 2007).

The molecules are linked into a three-dimensional network by N–H···O, O–H···O, O–H···N hydrogen bonds and C–H···π interactions. (Table 1).

Experimental

4-Hydroxy-acetophenone (1.36 g, 0.01 mol) and methyl hydrazinecarboxylate (0.90 g, 0.01 mol) were dissolved in stirred methanol (25 ml) and left for 4 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 80% yield. Crystals suitable for X-ray analysis were obtained by slow evaporation of a ethanol solution at room temperature (m.p. 483–485 K).