2,4-Dichloro­benzaldehyde 4-methyl­thio­semicarbazone

Rongchun Li

doi:10.1107/S1600536810049743

. 2010 Dec 4;67(Pt 1):o20. doi: 10.1107/S1600536810049743

2,4-Dichlorobenzaldehyde 4-methylthiosemicarbazone

Rongchun Li ^a,^*

PMCID: PMC3050402 PMID: 21522701

Abstract

The molecule of the title compound, C₉H₉Cl₂N₃S, has an E configuration about the C=N bond. In the crystal, molecules are linked through intermolecular N—H⋯S hydrogen bonds, forming zigzag 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 a similar structure reported recently by the author, see: Li (2010 ▶). 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

C₉H₉Cl₂N₃S
M _r = 262.15
Monoclinic,
a = 13.444 (3) Å
b = 9.3299 (19) Å
c = 18.499 (4) Å
β = 92.160 (2)°
V = 2318.7 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.71 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.883, T _max = 0.913
7167 measured reflections
2518 independent reflections
1956 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.092
S = 1.05
2518 reflections
143 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.35 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/S1600536810049743/hg2763sup1.cif

e-67-00o20-sup1.cif^{(14.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049743/hg2763Isup2.hkl

e-67-00o20-Isup2.hkl^{(123.8KB, 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
N2—H2⋯S1ⁱ	0.90 (1)	2.54 (1)	3.4169 (18)	167 (2)
N3—H3⋯S1ⁱⁱ	0.89 (1)	2.77 (2)	3.491 (2)	139 (2)

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

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). As a continuation of the work on the structures of such compounds (Li, 2010), in this paper, the title new Schiff base compound derived from the condensation of 2,4-dichlorobenzaldehyde with 4-methylthiosemicarbazone is reported.

The molecule of the title compound, Fig. 1, possesses an E configuration about the C7═N1 bond. 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···S 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 2,4-dichlorobenzaldehyde (0.174 g, 1 mmol) with 4-methylthiosemicarbazone (0.105 g, 1 mmol) in methanol. The excess methanol was removed by distillation. Colourless block shaped single crystals were obatined by slow evaporation of an ethanol solution of the product in air.