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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1678.
Published online 2009 June 24. doi:  10.1107/S1600536809023654
PMCID: PMC2969481

Ethyl (E)-2-(2-furyl­idene)hydrazine­carboxyl­ate

Abstract

In the title compound, C8H10N2O3, the hydrazinecarboxyl­ate group is twisted from the furan ring by 6.98 (17)°. In the crystal, the mol­ecules are linked into one-dimensional chains running along the c axis by N—H(...)O hydrogen bonds.

Related literature

For general background, see: Parashar et al. (1988 [triangle]); Hadjoudis et al. (1987 [triangle]); Borg et al. (1999 [triangle]); Kahwa et al. (1986 [triangle]); Santos et al. (2001 [triangle]). For a related structure, see: Shang et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1678-scheme1.jpg

Experimental

Crystal data

  • C8H10N2O3
  • M r = 182.18
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1678-efi1.jpg
  • a = 14.150 (6) Å
  • b = 9.285 (5) Å
  • c = 8.108 (4) Å
  • β = 118.540 (16)°
  • V = 935.8 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 223 K
  • 0.24 × 0.22 × 0.17 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2002 [triangle]) T min = 0.975, T max = 0.985
  • 2344 measured reflections
  • 816 independent reflections
  • 733 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.071
  • S = 1.07
  • 816 reflections
  • 118 parameters
  • H-atom parameters constrained
  • Δρmax = 0.10 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023654/bg2272sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023654/bg2272Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors are grateful for financial suport from the Zhejiang University of Technology Foundation (grant No. 20080169) and the Analysis and Measurement Foundation of Zhejiang Province (grant No. 2008 F70003).

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).

In the title compound, C8H10N2O3 (I), the N1/N2/O2/O3/C6/C7 planes form dihedral angles of 6.98 (17)° with the O1/C1—C4 planes.The bond lengths and angles are comparable to those observed for methylN'-[(E)-4-methoxybenzylidene]hydrazinecarboxylate (Shang et al., 2007).

In the crystal structure, the molecules are linked into one-dimentional chains running along the c axis by N—H···O hydrogen bonds(Table 1,Fig.1).

Experimental

Furfuraldehyde (0.96 g, 0.01 mol) and Ethyl hydrazinecarboxylate (1.04 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 95% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 410–412 K).

Refinement

H atoms were positioned geometrically (N—H = 0.86 Å and C—H = 0.93 or 0.96 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(Cmethyl). In the absence of significant anomalous scattering effects, Friedel pairs were averaged.

Figures

Fig. 1.
The asymmetric unit of (I). Displacement ellipsoids are drawn at the 40% probability level.
Fig. 2.
Crystal packing of (I), showing the formation of chains along c. Hydrogen bonds are shown as dashed lines.

Crystal data

C8H10N2O3F(000) = 384
Mr = 182.18Dx = 1.293 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1451 reflections
a = 14.150 (6) Åθ = 2.7–25.0°
b = 9.285 (5) ŵ = 0.10 mm1
c = 8.108 (4) ÅT = 223 K
β = 118.540 (16)°Block, colourless
V = 935.8 (8) Å30.24 × 0.22 × 0.17 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer816 independent reflections
Radiation source: fine-focus sealed tube733 reflections with I > 2σ(I)
graphiteRint = 0.024
[var phi] and ω scansθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)h = −16→16
Tmin = 0.975, Tmax = 0.985k = −10→10
2344 measured reflectionsl = −8→9

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0384P)2 + 0.0727P] where P = (Fo2 + 2Fc2)/3
816 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.10 e Å3
0 restraintsΔρmin = −0.16 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O3−0.05924 (14)−0.0975 (2)0.4141 (2)0.0686 (5)
N20.10734 (15)−0.0174 (2)0.5472 (3)0.0561 (5)
H20.09340.01880.63090.067*
O10.41276 (15)0.0404 (2)0.6109 (3)0.0754 (6)
O20.04565 (14)−0.1545 (2)0.2815 (2)0.0654 (5)
N10.20660 (15)0.0030 (2)0.5573 (3)0.0527 (5)
C30.4583 (2)0.1980 (3)0.8408 (4)0.0702 (8)
H30.45550.25800.93020.084*
C50.27221 (19)0.0837 (3)0.6911 (3)0.0541 (6)
H50.25030.12480.77190.065*
C60.03274 (18)−0.0952 (3)0.4038 (3)0.0531 (6)
C40.37893 (19)0.1127 (2)0.7200 (3)0.0533 (6)
C7−0.1479 (2)−0.1819 (4)0.2726 (4)0.0785 (8)
H7A−0.1895−0.22340.32730.094*
H7B−0.1196−0.26010.22990.094*
C10.5472 (2)0.1804 (3)0.8079 (4)0.0745 (8)
H10.61380.22590.87050.089*
C20.5161 (2)0.0859 (4)0.6694 (5)0.0822 (9)
H2A0.55890.05440.61830.099*
C8−0.2181 (3)−0.0897 (5)0.1115 (5)0.1058 (12)
H8A−0.2758−0.14650.01900.159*
H8B−0.1769−0.04920.05710.159*
H8C−0.2473−0.01350.15370.159*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O30.0582 (10)0.0793 (13)0.0731 (12)−0.0042 (9)0.0354 (9)−0.0022 (10)
N20.0546 (12)0.0655 (13)0.0533 (11)0.0001 (10)0.0299 (9)−0.0041 (10)
O10.0585 (10)0.0904 (12)0.0779 (12)−0.0088 (10)0.0329 (10)−0.0277 (11)
O20.0669 (10)0.0755 (11)0.0593 (10)−0.0093 (9)0.0347 (9)−0.0106 (9)
N10.0517 (11)0.0574 (11)0.0510 (11)0.0013 (9)0.0261 (9)0.0025 (9)
C30.081 (2)0.0659 (17)0.0638 (16)−0.0113 (15)0.0347 (15)−0.0160 (13)
C50.0610 (14)0.0538 (14)0.0474 (13)0.0032 (13)0.0259 (11)0.0004 (12)
C60.0517 (13)0.0586 (15)0.0521 (14)0.0045 (11)0.0273 (11)0.0110 (12)
C40.0594 (14)0.0537 (13)0.0451 (12)0.0034 (11)0.0236 (11)−0.0002 (11)
C70.0616 (16)0.082 (2)0.092 (2)−0.0168 (16)0.0366 (16)−0.0043 (17)
C10.0593 (14)0.0745 (19)0.0787 (19)−0.0163 (14)0.0241 (14)−0.0068 (15)
C20.0567 (15)0.099 (2)0.095 (2)−0.0099 (15)0.0392 (15)−0.0218 (19)
C80.0683 (19)0.126 (3)0.103 (3)−0.012 (2)0.0241 (19)0.006 (2)

Geometric parameters (Å, °)

O3—C61.344 (3)C5—C41.438 (4)
O3—C71.459 (3)C5—H50.9300
N2—C61.347 (3)C7—C81.479 (5)
N2—N11.380 (2)C7—H7A0.9700
N2—H20.8600C7—H7B0.9700
O1—C21.371 (4)C1—C21.324 (4)
O1—C41.366 (3)C1—H10.9300
O2—C61.221 (3)C2—H2A0.9300
N1—C51.279 (3)C8—H8A0.9600
C3—C41.341 (4)C8—H8B0.9600
C3—C11.415 (4)C8—H8C0.9600
C3—H30.9300
C6—O3—C7117.0 (2)O3—C7—C8110.2 (3)
C6—N2—N1118.71 (18)O3—C7—H7A109.6
C6—N2—H2120.6C8—C7—H7A109.6
N1—N2—H2120.6O3—C7—H7B109.6
C2—O1—C4105.7 (2)C8—C7—H7B109.6
C5—N1—N2115.90 (18)H7A—C7—H7B108.1
C4—C3—C1107.7 (2)C2—C1—C3105.7 (2)
C4—C3—H3126.1C2—C1—H1127.1
C1—C3—H3126.1C3—C1—H1127.1
N1—C5—C4121.9 (2)C1—C2—O1111.5 (3)
N1—C5—H5119.1C1—C2—H2A124.3
C4—C5—H5119.1O1—C2—H2A124.3
O2—C6—O3124.6 (2)C7—C8—H8A109.5
O2—C6—N2125.6 (2)C7—C8—H8B109.5
O3—C6—N2109.7 (2)H8A—C8—H8B109.5
C3—C4—O1109.4 (2)C7—C8—H8C109.5
C3—C4—C5132.7 (2)H8A—C8—H8C109.5
O1—C4—C5117.9 (2)H8B—C8—H8C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.862.082.916 (3)164

Symmetry codes: (i) x, −y, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2272).

References

  • Borg, S., Vollinga, R. C., Labarre, M., Payza, K., Terenius, L. & Luthman, K. (1999). J. Med. Chem.42, 4331–4342. [PubMed]
  • Bruker (2002). SADABS, SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hadjoudis, E., Vittorakis, M. & Moustakali-Mavridis, J. (1987). Tetrahedron, 43, 1345–1360.
  • Kahwa, I. A., Selbin, J., Hsieh, T. Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 151, 201–208.
  • Parashar, R. K., Sharma, R. C., Kumar, A. & Mohanm, G. (1988). Inorg. Chim. Acta, 151, 201–208.
  • Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844.
  • Shang, Z.-H., Zhang, H.-L. & Ding, Y. (2007). Acta Cryst. E63, o3394.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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