1-(2-Furylmethyl­ene)-2-(2-nitro­phen­yl)hydrazine

Yin, Z.-G.; Fei, Z.-L.; Qian, H.-Y.; Zhu, X.-W.; Zhang, C.-X.

doi:10.1107/S1600536809037052

Volume 65
Part 10
Page o2534
October 2009

Received 11 September 2009
Accepted 13 September 2009
Online 26 September 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.007 Å
R = 0.070
wR = 0.195
Data-to-parameter ratio = 13.2
Details

1-(2-Furylmethylene)-2-(2-nitrophenyl)hydrazine

Zhi-Gang Yin,^a ^* Zong-Lei Fei,^a Heng-Yu Qian,^a Xue-Wen Zhu ^a and Chun-Xia Zhang ^a

^aKey Laboratory of Surface and Interface Science of Henan, School of Materials & Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China
Correspondence e-mail: yinck@263.net

The title Schiff base compound, C₁₁H₉N₃O₃, was obtained from a condensation reaction of furan-2-carbaldehyde and 2-nitrophenylhydrazine. The molecule is roughly planar, the largest deviation from the mean plane defined by all non-H atoms being 0.097 (4). An in ntramolecular N-HO hydrogen bond might influence the planar conformation of the molecule. In the crystal, weak C-HO hydrogen bonds link the molecules, forming a chain.

Related literature

For the role played by Schiff base compounds in the development of various proteins and enzymes, see: Kahwa et al. (1986); Santos et al. (2001).

Experimental

Crystal data

C₁₁H₉N₃O₃
M_r = 231.21
Monoclinic, P 2₁ /n
a = 15.852 (3) Å
b = 3.8000 (12) Å
c = 17.721 (4) Å
= 97.89 (2)°
V = 1057.4 (5) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 296 K
0.21 × 0.19 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998) T_min = 0.979, T_max = 0.982
3497 measured reflections
2033 independent reflections
619 reflections with I > 2(I)
R_int = 0.063

Refinement

R[F² > 2(F²)] = 0.070
wR(F²) = 0.195
S = 0.73
2033 reflections
154 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1	0.86	1.98	2.599 (5)	128
C2-H2AO2ⁱ	0.93	2.48	3.360 (7)	158
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2486 ).

Acknowledgements

The authors would like to express their deep appreciation to the startup fund for PhDs of the Natural Scientific Research of Zhengzhou University of Light Industry (No. 2005001) and the Fund for Natural Scientific Research of Zhengzhou University of Light Industry (000455).

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. AXS Inc., Madison, Wisconsin, USA.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, U.SA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Kahwa, I. A., Selbin, I., Hsieh, T. C. Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179-185.
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838-844.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds