(E)-Methyl N′-(3-methoxy­benzyl­idene)hydrazinecarboxyl­ate

Lu-Ping Lv; Wen-Bo Yu; Chun-Yu Huang; Wei-Wei Li; Xian-Chao Hu

doi:10.1107/S1600536809033194

. 2009 Aug 26;65(Pt 9):o2243. doi: 10.1107/S1600536809033194

(E)-Methyl N′-(3-methoxybenzylidene)hydrazinecarboxylate

Lu-Ping Lv ^a, Wen-Bo Yu ^a, Chun-Yu Huang ^b, Wei-Wei Li ^a, Xian-Chao Hu ^c,^*

PMCID: PMC2970081 PMID: 21577641

Abstract

The title compound, C₁₀H₁₂N₂O₃, crystallizes with two independent molecules in the asymmetric unit which differ in the orientation of the methoxy group. Each independent molecule adopts a trans configuration with respect to the C=N bond. In the crystal structure, molecules are linked into chains running along [001] by N—H⋯O and N—H⋯N hydrogen bonds. In addition, an intermolecular C—H⋯π interaction is observed.

Related literature

For general background to the properties of benzaldehydehydrazone derivatives, see: Parashar et al. (1988 ▶); Hadjoudis et al. (1987 ▶); Borg et al. (1999 ▶); Kahwa et al. (1986 ▶); Santos et al. (2001 ▶). For a related structure, see: Shang et al. (2007 ▶).

Experimental

Crystal data

C₁₀H₁₂N₂O₃
M _r = 208.22
Monoclinic,
a = 18.207 (3) Å
b = 7.3677 (12) Å
c = 16.552 (3) Å
β = 104.243 (5)°
V = 2152.1 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 223 K
0.24 × 0.21 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.977, T _max = 0.989
11364 measured reflections
3790 independent reflections
3033 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.109
S = 1.07
3790 reflections
276 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 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/S1600536809033194/ci2891sup1.cif

e-65-o2243-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033194/ci2891Isup2.hkl

e-65-o2243-Isup2.hkl^{(182KB, 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
N2—H2⋯O5	0.86	2.07	2.9188 (18)	172
N4—H4⋯O2ⁱ	0.86	2.25	2.8365 (17)	126
N4—H4⋯N1ⁱ	0.86	2.55	3.3883 (19)	164
C11—H11B⋯Cg1ⁱⁱ	0.96	2.91	3.776 (3)	150

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the centroid of the C12–C17 ring.

Acknowledgments

The authors thank the Science and Technology Project of Zhejiang Province (grant No. 2007 F70077) and 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 compound contains two independent, but almost identical molecules in the asymmetric unit. Each independent molecule adopts a trans configuration with respect to the C═N bond. The N1/N2/O2/O3/C8/C9/C10 and N3/N4/O5/O6/C18/C19/C20 planes form dihedral angles of 4.51 (6)° and 13.80 (6)°, respectively, with the C2—C7 and C12—C17 planes. The dihedral angle between the two independent benzene rings is 59.18 (6)°. Bond lengths and angles are comparable to those observed for methylN'-[(E)-4-methoxybenzylidene]hydrazinecarboxylate (Shang et al., 2007).

In the crystal structure, molecules are linked into chains running along the [001] by N—H···O and N—H···N hydrogen bonds. In addition, an intermolecular C—H···π interaction is observed (Table 1).

Experimental

3-Methoxybenzaldehyde (1.36 g, 0.01 mol) and methyl hydrazinecarboxylate (0.90 g, 0.01 mol) were dissolved in stirred methanol (20 ml) and left for 2.5 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 95% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 436–438 K).