4-Methyl-1-(3-pyridyl­methyl­idene)thio­semicarbazide

Rongchun Li

doi:10.1107/S1600536810048853

. 2010 Nov 27;66(Pt 12):o3324. doi: 10.1107/S1600536810048853

4-Methyl-1-(3-pyridylmethylidene)thiosemicarbazide

Rongchun Li ^a,^*

PMCID: PMC3011564 PMID: 21589600

Abstract

All the non-H atoms of the title compound, C₈H₁₀N₄S, lie on a crystallographic mirror plane and an intramolecular N—H⋯N hydrogen bond helps to stabilize the molecular conformation. In the crystal, molecules are linked through intermolecular N—H⋯N hydrogen bonds, forming zigzag C(7) chains along the a axis.

Related literature

For background to Schiff bases derived from thiosemicarbazone and its derivatives, see: Casas et al. (2001 ▶); Beraldo et al. (2001 ▶); Jouad et al. (2002 ▶); Swearingen et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶). For similar structures, see: Selvanayagam et al. (2002 ▶); Karakurt et al. (2003 ▶); Bernhardt et al. (2003 ▶); Sampath et al. (2003 ▶).

Experimental

Crystal data

C₈H₁₀N₄S
M _r = 194.26
Monoclinic,
a = 7.276 (3) Å
b = 6.581 (2) Å
c = 10.297 (3) Å
β = 92.997 (2)°
V = 492.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.953, T _max = 0.958
3208 measured reflections
1106 independent reflections
640 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.118
S = 1.02
1106 reflections
84 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048853/hb5755sup1.cif

e-66-o3324-sup1.cif^{(13.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048853/hb5755Isup2.hkl

e-66-o3324-Isup2.hkl^{(54.8KB, 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
N4—H4⋯N2	0.90 (2)	2.14 (3)	2.585 (4)	109 (2)
N3—H3⋯N1ⁱ	0.90 (1)	2.09 (1)	2.989 (3)	176 (3)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Thiosemicarbazone and its derivatives are important materials for the preparation of Schiff bases (Casas et al., 2001; Beraldo et al., 2001; Jouad et al., 2002; Swearingen et al., 2002). In this paper, the title new Schiff base compound derived from the condensation of 3-formylpyridine with 4-methylthiosemicarbazone is reported.

The molecule of the title compound, Fig. 1, possess a crystallographic mirror plane symmetry. The bond lengths have normal values (Allen et al., 1987), and are comparable to those observed in similar compounds (Selvanayagam et al., 2002; Karakurt et al., 2003; Bernhardt et al., 2003; Sampath et al., 2003).

In the crystal, molecules are linked through intermolecular N—H···N hydrogen bonds (Table 1), to form zigzag chains along the a axis (Fig. 2).

Experimental

The title compound was prepared by the Schiff base condensation of equimolar quantities of 3-formylpyridine (0.107 g, 1 mmol) with 4-methylthiosemicarbazone (0.105 g, 1 mmol) in methanol. The excess methanol was removed by distillation. Colourless blocks were obtained by slow evaporation of an ethanol solution of the product in air.