2-Chloro-5-nitro­benzaldehyde thio­semicarbazone

Yu-Mei Hao

doi:10.1107/S1600536810035701

. 2010 Sep 11;66(Pt 10):o2528. doi: 10.1107/S1600536810035701

2-Chloro-5-nitrobenzaldehyde thiosemicarbazone

Yu-Mei Hao ^a,^*

PMCID: PMC2983295 PMID: 21587521

Abstract

The title Schiff base compound, C₈H₇ClN₄O₂S, was prepared by the reaction of equimolar quantities of 2-chloro-5-nitrobenzaldehyde with thiosemicarbazide in methanol. The molecule adopts a trans configuration with respect to the azomethine group and the dihedral angle between the benzene ring and the thiosemicarbazide group is 6.8 (3)°. In the crystal, molecules are linked through intermolecular N—H⋯S hydrogen bonds, forming chains propagating in [010].

Related literature

For the crystal structures of similar Schiff base compounds, see: Ferrari et al. (1999 ▶); Shanmuga Sundara Raj et al. (2000 ▶); Chattopadhyay et al. (1988 ▶). For a similar compound reported by the author, see: Hao (2010 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₈H₇ClN₄O₂S
M _r = 258.69
Monoclinic,
a = 11.611 (2) Å
b = 8.439 (2) Å
c = 12.016 (3) Å
β = 113.909 (2)°
V = 1076.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.54 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.909, T _max = 0.914
6657 measured reflections
2344 independent reflections
1573 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.111
S = 1.02
2344 reflections
154 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035701/hb5633sup1.cif

e-66-o2528-sup1.cif^{(14KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035701/hb5633Isup2.hkl

e-66-o2528-Isup2.hkl^{(115.2KB, 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—H4A⋯S1ⁱ	0.89 (1)	2.53 (1)	3.408 (2)	173 (2)
N3—H3⋯S1ⁱⁱ	0.90 (1)	2.46 (1)	3.3266 (19)	161 (2)

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

supplementary crystallographic information

Comment

Recently, the crystal structures of a number of Schiff base compounds bearing the hydrazone groups derived from the thiosemicarbazide with aldehydes have been reported (Ferrari et al., 1999; Shanmuga Sundara Raj et al., 2000; Chattopadhyay et al., 1988). Recently, the author has reported a Schiff base compound derived from the thiosemicarbazide with 2-hydroxy-4-methoxybenzaldehyde (Hao, 2010), in this paper, the title new Schiff base compound, (I), Fig. 1, is reported.

The molecule of the title compound adopts a trans configuration with respect to the azomethine group. All the bond lengths are within normal values (Allen et al., 1987). The dihedral angle between the C1-C6 benzene ring and the plane defined by N2-N3-C8-S1-N4 is 6.8 (3)°, indicating the planar of the molecule. In the crystal structure, molecules are linked through intermolecular N—H···S hydrogen bonds (Table 1), to form chains (Fig. 2).

Experimental

2-Chloro-5-nitrobenzaldehyde (0.1 mmol, 18.6 mg) and thiosemicarbazide (0.1 mmol, 9.1 mg) were refluxed in methanol (30 ml) for 30 min to give a clear yellow solution. Yellow blocks of (I) were formed by slow evaporation of the solvent over several days at room temperature.