(E)-2-Acetyl­pyrazine 4-nitro­phenyl­hydrazone

Shang Shan; Yu-Liang Tian; Shan-Heng Wang; Wen-Long Wang; Ying-Li Xu

doi:10.1107/S1600536808017479

. 2008 Jun 13;64(Pt 7):o1265. doi: 10.1107/S1600536808017479

(E)-2-Acetylpyrazine 4-nitrophenylhydrazone

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

PMCID: PMC2961878 PMID: 21202899

Abstract

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 π–π stacking between adjacent molecules. The crystal structure also contains N—H⋯N and C—H⋯O 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,
a = 8.0101 (6) Å
b = 12.5154 (11) Å
c = 12.1506 (12) Å
β = 98.564 (2)°
V = 1204.51 (18) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.149
S = 1.08
2747 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017479/sg2248sup1.cif

e-64-o1265-sup1.cif^{(15.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017479/sg2248Isup2.hkl

e-64-o1265-Isup2.hkl^{(132.1KB, 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—H2N⋯N5ⁱ	0.91	2.30	3.185 (2)	164
C11—H11⋯O1ⁱⁱ	0.93	2.60	3.300 (3)	133

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

Acknowledgments

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

supplementary crystallographic information

Comment

Hydrazone and its derivatives have attracted much attention because of their potential application in biology (Okabe et al., 1993; Hu et al., 2001). As part of an ongoing investigation into anti-cancer compounds (Chen et al., 2007), the title compound has recently been prepared in our laboratory and its crystal structure is presented here.

The molecular structure of the title compound is shown in Fig. 1. The molecule adopts an E-configuration, with the benzene and pyrazine rings located on the opposite positions of the N3=C7 double bond, similar to that found in a related structure, (E)-2-Furyl methyl ketone 2,4-dinitrophenylhydrazone (Shan et al., 2008). The pyrazine plane is twisted with respect to the benzene ring by a smaller dihedral angle of 14.25 (10)°.

The partially overlapped arrangement is observed between parallel benzene rings and between parallel pyrazine rings (Fig. 2), face-to-face separations of 3.413 (14) [for benzene rings] and 3.430 (8) Å [for pyrazine rings] are significantly shorter than van der Waals thickness of the aromatic ring (3.70 Å), and indicate the existence of π-π stacking between the adjacent molecules. Intermolecular N—H···N and weak C—H···O hydrogen bondings are present in the crystal structure (Table 1).

Experimental

4-Nitrophenylhydrazine (0.31 g, 2 mmol) was dissolved in ethanol (10 ml), then H₂SO₄ solution (98%, 0.5 ml) was added slowly to the ethanol solution with stirring. The solution was heated at about 333 K for several minutes until the solution cleared. An ethanol solution (5 ml) of acetylpyrazine (0.24 g, 2 mmol) was dropped slowly into the above solution with continuous stirring, and the mixture solution was kept at about 333 K for 0.5 h. When the solution had cooled to room temperature, yellow microcrystals appeared. They were separated and washed with cold water three times to get the product 0.40 g. Single crystals of the title compound were obtained by recrystallization from an absolute ethanol solution.