Methyl 2-[(E)-3-hydr­oxy-4-methoxy­benzyl­idene]hydrazinecarboxyl­ate

Lu-Ping Lv; Tie-Ming Yu; Wen-Bo Yu; Wei-Wei Li; Xian-Chao Hu

doi:10.1107/S1600536809018996

. 2009 May 23;65(Pt 6):o1384. doi: 10.1107/S1600536809018996

Methyl 2-[(E)-3-hydroxy-4-methoxybenzylidene]hydrazinecarboxylate

Lu-Ping Lv ^a, Tie-Ming Yu ^a, Wen-Bo Yu ^a, Wei-Wei Li ^a, Xian-Chao Hu ^b,^*

PMCID: PMC2969549 PMID: 21583232

Abstract

The title compound, C₁₀H₁₂N₂O₄, adopts a trans configuration with respect to the C=N bond. The hydrazinecarboxylate group is twisted from the benzene ring by 6.62 (5)° and an intramolecular O—H⋯O hydrogen bond occurs. In the crystal structure, molecules are linked into a two-dimensional network parallel to (100) by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds. In addition, weak C—H⋯π interactions are observed.

Related literature

For properties of benzaldehydehydrazone derivatives, see: Parashar et al. (1988 ▶); Hadjoudis et al. (1987 ▶); Borg et al. (1999 ▶). For Schiff base metal complexes, see: Kahwa et al. (1986 ▶); Santos et al. (2001 ▶). For a related structure, see: Shang et al. (2007 ▶).

Experimental

Crystal data

C₁₀H₁₂N₂O₄
M _r = 224.22
Monoclinic,
a = 7.7223 (12) Å
b = 9.2106 (14) Å
c = 15.092 (2) Å
β = 100.944 (6)°
V = 1054.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 223 K
0.18 × 0.16 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.978, T _max = 0.982
5767 measured reflections
1944 independent reflections
1657 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.098
S = 1.05
1944 reflections
149 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 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/S1600536809018996/ci2804sup1.cif

e-65-o1384-sup1.cif^{(15.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018996/ci2804Isup2.hkl

e-65-o1384-Isup2.hkl^{(93.7KB, 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
O2—H2⋯O1	0.82	2.28	2.6871 (13)	112
O2—H2⋯O3ⁱ	0.82	2.20	2.9303 (13)	148
N2—H2A⋯O3ⁱⁱ	0.86	2.44	3.1951 (15)	147
C8—H8⋯O3ⁱⁱ	0.93	2.51	3.3185 (16)	146
C10—H10A⋯Cg1ⁱⁱⁱ	0.96	2.87	3.6878 (18)	143

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 is the centroid of the C2–C7 ring.

Acknowledgments

The authors thank Hangzhou Vocational and Technical College for financial support.

supplementary crystallographic information

Comment

Benzaldehydehydrazone derivatives have attracted much attention due to their pharmacological activity (Parashar et al., 1988) and their photochromic properties (Hadjoudis et al., 1987). They are important intermediates of 1,3,4-oxadiazoles, which have been reported to be versatile compounds with many interesting properties (Borg et al., 1999). Metal complexes based on Schiff bases have received considerable attention because they can be utilized as model compounds of active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). We report here the crystal structure of the title compound (Fig. 1).

The title molecule adopts a trans configuration with respect to the C═N bond. The hydrazinecarboxylate group is twisted from the benzene ring by 6.62 (5)°. The bond lengths and angles are comparable to those observed for methylN'-[(E)-4-methoxybenzylidene]hydrazinecarboxylate (Shang et al., 2007). An intramolecular O—H···O interaction is observed.

In the crystal structure, the molecules are linked into a two-dimensional network parallel to the (100) by O—H···O, N—H···O and C—H···O hydrogen bonds (Table 1 and Fig.2). In addition, a C—H···π interaction is observed.

Experimental

3-Hydroxy-4-methoxy-benzaldehyde (1.52 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 75% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 398–401 K).