(E)-2-Acetyl­pyrazine 4-nitro­phenyl­hydrazone

Shan, S.; Tian, Y.-L.; Wang, S.-H.; Wang, W.-L.; Xu, Y.-L.

doi:10.1107/S1600536808017479

Volume 64
Part 7
Page o1265
July 2008

Received 7 June 2008
Accepted 10 June 2008
Online 13 June 2008

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R = 0.043
wR = 0.150
Data-to-parameter ratio = 15.8
Details

(E)-2-Acetylpyrazine 4-nitrophenylhydrazone

Shang Shan,^a ^* Yu-Liang Tian,^a Shan-Heng Wang,^a Wen-Long Wang ^a and Ying-Li Xu ^a

^aCollege of Chemical Engineering and Materials Science, Zhejiang University of Technology, People's Republic of China
Correspondence e-mail: shanshang@mail.hz.zj.cn

In the title compound, C₁₂H₁₁N₅O₂, the molecule adopts an E configuration, with the benzene and pyrazine rings located on opposite sides of the N=C double bond. The face-to-face separations of 3.413 (14) and 3.430 (8) Å, respectively between parallel benzene rings and between pyrazine rings indicate the existence of [pi] - [pi] stacking between adjacent molecules. The crystal structure also contains N-HN and C-HO hydrogen bonding.

Related literature

For general background, see: Okabe et al. (1993); Hu et al. (2001); Chen et al. (2007). For a related structure, see: Shan et al. (2008).

Experimental

Crystal data

C₁₂H₁₁N₅O₂
M_r = 257.26
Monoclinic, P 2₁ /n
a = 8.0101 (6) Å
b = 12.5154 (11) Å
c = 12.1506 (12) Å
= 98.564 (2)°
V = 1204.51 (18) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 295 (2) K
0.40 × 0.38 × 0.26 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: none
11633 measured reflections
2747 independent reflections
1446 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.149
S = 1.08
2747 reflections
174 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2NN5ⁱ	0.91	2.30	3.185 (2)	164
C11-H11O1ⁱⁱ	0.93	2.60	3.300 (3)	133
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x-1, y-1, z.

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2248 ).

Acknowledgements

The work was supported by the Natural Science Foundation of Zhejiang Province of China (No. M203027).

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
Chen, Z.-Y., Wu, G.-Q., Jiang, F.-X., Tian, Y.-L. & Shan, S. (2007). Acta Cryst. E63, o1919-o1920.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Hu, W., Sun, N. & Yang, Z. (2001). Chem. J. Chin. Univ. 22, 2014-2017.
Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678-1680.
Rigaku. (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku. (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Shan, S., Tian, Y.-L., Wang, S.-H., Wang, W.-L. & Xu, Y.-L. (2008). Acta Cryst. E64, o1153.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds