Thio­phene-2-carbaldehyde 2,4-dinitro­phenyl­hydrazone

Yin, Z.; Qian, H.; Li, H.; Hu, J.; Zhang, C.

doi:10.1107/S1600536808038397

Volume 64
Part 12
Page o2421
December 2008

Received 13 November 2008
Accepted 18 November 2008
Online 22 November 2008

Key indicators
Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.003 Å
R = 0.045
wR = 0.087
Data-to-parameter ratio = 12.4
Details

Thiophene-2-carbaldehyde 2,4-dinitrophenylhydrazone

Zhi-gang Yin,^a ^* Heng-yu Qian,^a He-ping Li,^b Jie Hu ^a and Chun-xia Zhang ^a

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

In the approximately planar molecule of the title compound, C₁₁H₈N₄O₄S, the dihedral angle between the thiophene and benzene rings is 5.73 (10)°. In the crystal structure, bifurcated inter/intramolecular N-H(O,O) hydrogen bonds are present. The intermolecular links lead to inversion dimers containing an R₂²(12) graph-set motif.

Related literature

For general background, see: Okabe et al. (1993). For graph-set notation, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₁₁H₈N₄O₄S
M_r = 292.27
Monoclinic, P 2₁ /c
a = 4.8994 (17) Å
b = 9.520 (3) Å
c = 25.708 (8) Å
= 92.71 (2)°
V = 1197.7 (7) Å³
Z = 4
Mo K radiation
= 0.29 mm^-1
T = 291 (2) K
0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.915, T_max = 0.929
11010 measured reflections
2285 independent reflections
1718 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.087
S = 1.02
2285 reflections
184 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.16 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H1O1ⁱ	0.87 (2)	2.57 (2)	3.338 (2)	148.2 (19)
N3-H1O1	0.87 (2)	2.01 (2)	2.630 (2)	127.4 (19)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2406 ).

Acknowledgements

The authors express their deep appreciation to the Startup Fund for PhDs of Natural Scientific Research of Zhengzhou University of Light Industry (grant No. 2005001) and the Startup Fund for Masters of Natural Scientific Research of Zhengzhou University of Light Industry (grant No. 000455).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678-1680.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds