(E)-Methyl N′-(2-furylmethyl­ene)­hydrazinecarboxyl­ate

Lu-Ping Lv; Yong-Zhao Zhang; Xiao-Min Ding; Wen-Bo Yu; Xian-Chao Hu

doi:10.1107/S1600536808033825

. 2008 Oct 22;64(Pt 11):o2146. doi: 10.1107/S1600536808033825

(E)-Methyl N′-(2-furylmethylene)hydrazinecarboxylate

Lu-Ping Lv ^a, Yong-Zhao Zhang ^a, Xiao-Min Ding ^a, Wen-Bo Yu ^b, Xian-Chao Hu ^c,^*

PMCID: PMC2959771 PMID: 21581006

Abstract

The title compound, C₇H₈N₂O₃, crystallizes with two independent but essentially identical molecules in the asymmetric unit. Each molecule adopts a trans configuration with respect to the C=N bond. The hydrazinecarboxylate group is twisted from the furan ring by 7.78 (13)° in one molecule and by 7.01 (17)° in the other. In the crystal structure, molecules are linked into chains running along [010] by bifurcated N—H⋯(N,O) and N—H⋯O hydrogen bonds. In addition, weak C—H⋯O interactions and an O⋯C short contact [2.896 (3) Å] are observed.

Related literature

For general background, 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

C₇H₈N₂O₃
M _r = 168.15
Monoclinic,
a = 14.9185 (17) Å
b = 7.8124 (9) Å
c = 15.1299 (19) Å
β = 105.251 (7)°
V = 1701.3 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 193 (2) K
0.19 × 0.17 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.978, T _max = 0.982
4679 measured reflections
1601 independent reflections
1399 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.085
S = 1.07
1601 reflections
218 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.09 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/S1600536808033825/ci2688sup1.cif

e-64-o2146-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033825/ci2688Isup2.hkl

e-64-o2146-Isup2.hkl^{(77.3KB, 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—H2A⋯O5	0.86	2.36	3.138 (3)	151
N2—H2A⋯N3	0.86	2.52	3.242 (3)	141
N4—H4⋯O2ⁱ	0.86	2.11	2.913 (3)	156
C2—H2⋯O5ⁱⁱ	0.93	2.60	3.521 (4)	172
C10—H10⋯O5ⁱⁱⁱ	0.93	2.59	3.508 (4)	171

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

Acknowledgments

The authors thank Hangzhou Vocational and Technical College, China, 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 intermidiates 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 essentially 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/C6/C7 and N3/N4/O5/O6/C13/C14 planes form dihedral angles of 7.78 (13) and 7.01 (17)°, respectively, with the O1/C1–C4 and O4/C8–C11 planes. The dihedral angle between the two independent furan rings is 85.17 (11)°. The bond lengths and angles are comparable to those observed for methyl N'-[(E)-4-methoxybenzylidene]hydrazinecarboxylate (Shang et al., 2007).

In the crystal structure, the molecules are linked into chains running along the [010] by N—H···O and N—H···N hydrogen bonds (Table 1 and Fig.2). In addition, weak C—H···O interactions and an O4···C5 short contact [2.896 (3) Å] are also observed.

Experimental

Furfuraldehyde (0.96 g, 0.01 mol) and methyl hydrazinecarboxylate (0.90 g, 0.01 mol) were dissolved in stirred methanol (20 ml) and left for 3 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 85% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 408–413 K).