2-Acetyl­pyrazine 4-methyl­thio­semi­carbazone

Jing Zhou; Yu-Xia Wang; Chun-Ling Chen; Ming-Xue Li

doi:10.1107/S160053680706285X

. 2007 Dec 6;64(Pt 1):o94. doi: 10.1107/S160053680706285X

2-Acetylpyrazine 4-methylthiosemicarbazone

Jing Zhou ^a, Yu-Xia Wang ^a, Chun-Ling Chen ^a, Ming-Xue Li ^a,^*

PMCID: PMC2915049 PMID: 21200971

Abstract

The title compound, C₈H₁₁N₅S, has been prepared by the reaction of 2-acetylpyrazine with 4-methyl-3-thiosemicarbazide. It exists in the thione form and adopts the E configuration. The molecules are connected by the intermolecular N—H⋯N and N—H⋯S interactions.

Related literature

For related literature, see: Hong et al. (2004 ▶); Latheef et al. (2006 ▶); Liberta & West (1992 ▶); Mendes et al. (2001 ▶); Padhye & Kauffman (1985 ▶).

Experimental

Crystal data

C₈H₁₁N₅S
M _r = 209.28
Monoclinic,
a = 9.870 (8) Å
b = 5.976 (5) Å
c = 17.517 (14) Å
β = 91.251 (9)°
V = 1032.8 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 (2) K
0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: none
9944 measured reflections
1919 independent reflections
1595 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.100
S = 1.05
1919 reflections
129 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706285X/at2513sup1.cif

e-64-00o94-sup1.cif^{(14.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706285X/at2513Isup2.hkl

e-64-00o94-Isup2.hkl^{(94.5KB, 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
N1—H1D⋯N4ⁱ	0.86	2.42	3.137 (3)	141
N2—H2A⋯S1ⁱⁱ	0.86	2.77	3.588 (3)	161

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

Acknowledgments

This work was financially supported by the Foundation of the Education Department of Henan Province (No. 2007150012)

supplementary crystallographic information

Comment

Thiosemicarbazone and its derivatives have attracted interest in recent years due to their beneficial biological applications (Padhye & Kauffman, 1985). The presence of alkyl groups at the terminal N(4) position can increase the biological activity (Liberta & West, 1992). So we report here the crystal structure of N(4)-methyl thiosemicarbazones derived from 2-acetylpyrazine.

The geometry of the title compound (I) is well planar (Fig. 1). The molecular exists in the E conformation about the C3—N3 bond as confirmed by the C5—C3—N3—N2 torsion angle of 179.6 °. The C—S bond distance of 1.679 (2) Å, which is much short than C—S single bond (Latheef et al., 2006), shows that the title compound adopts the thione form. The bond length of C3—N3 is 1.283 (2) Å, which is within the range of typical bond length of C?N double bond. The bond length of N2—N3 is 1.368 (2) Å, accepted as typical for a single N—N bond, and in accordance with those of other thiosemicarbazone (Mendes et al., 2001; Hong et al., 2004).

In the crystal packing, the molecules are connected through an extended network of intermolecular hydrogen bonds involving the nitrogen atoms N1, N2, N4 and sulfur atom S1.

Experimental

All reagents were commercially available and of analytical grade. 2-Acetylpyrazine (0.24 g, 2 mmol) and 4-methyl-3-thiosemicarbazide (0.21 g, 2 mmol) were mixed in ethanol (30 ml). Eight drops of acetic acid were added and the solution was refluxed for 4 h. Crystals of (I) suitable for X-ray diffraction analysis were obtained from the filtrate by slow evaporation at room temperature.