1-[1-(4-Nitro­phen­yl)ethyl­idene]thio­semicarbazide

Jian-Gang Wang; Fang-Fang Jian; Yu-Feng Ding

doi:10.1107/S1600536808025105

. 2008 Aug 9;64(Pt 9):o1730. doi: 10.1107/S1600536808025105

1-[1-(4-Nitrophenyl)ethylidene]thiosemicarbazide

Jian-Gang Wang ^a, Fang-Fang Jian ^b,^*, Yu-Feng Ding ^c

PMCID: PMC2960583 PMID: 21201713

Abstract

The title compound, C₉H₁₀N₄O₂S, was prepared by the reaction of 1-(4-nitrophenyl)ethanone and thiosemicarbazide in ethanol at 367 K. There are weak intermolecular N—H⋯S and N—H⋯O hydrogen-bonding interactions in the crystal structure involving the amine and nitrile groups, respectively, as donors.

Related literature

For related literature, see: Jian et al. (2006 ▶); Qin et al. (2006 ▶); Rozwadowski et al. (1999 ▶).

Experimental

Crystal data

C₉H₁₀N₄O₂S
M _r = 238.27
Triclinic,
a = 7.4450 (15) Å
b = 9.3180 (19) Å
c = 9.4050 (19) Å
α = 62.08 (3)°
β = 76.41 (3)°
γ = 69.02 (3)°
V = 536.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 293 (2) K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
2493 measured reflections
2307 independent reflections
1776 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.140
S = 1.08
2307 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 I, global. DOI: 10.1107/S1600536808025105/at2598sup1.cif

e-64-o1730-sup1.cif^{(14.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025105/at2598Isup2.hkl

e-64-o1730-Isup2.hkl^{(113.4KB, 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
N3—H3A⋯S1ⁱ	0.86	2.74	3.581 (2)	166
N4—H4A⋯O1ⁱⁱ	0.86	2.35	3.101 (3)	146
N4—H4B⋯O2ⁱⁱⁱ	0.86	2.29	3.133 (3)	166

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

supplementary crystallographic information

Comment

Schiff bases have been used extensively as ligands in the field of coordination chemistry (Jian et al., 2006). Schiff bases show biochemical and pharmacological applications. The growing interest in Schiff bases lately is also due to their ability to form intramolecular hydrogen bonds by electron coupling between acid-base centers (Rozwadowski et al.,1999). The title compound (I), was synthesized and we report here its crystal structure

In the crystal structure of (I) (Fig. 1). The C6–C9/N2/N3/S1 plane makes a dihedral angle of 19.78 (127)° with the benzene ring (C1—C6). The C═N bond length [1.281 (3) Å] and C═S bond length [1.685 (2) Å] are in agreement with those observed before (Jian et al., 2006; Qin et al., 2006). There are intermolecular N–H···S and N–H···O hydrogen-bond interactions to stabilize the crystal structure (Table 1).

Experimental

A mixture of hydrochloric acid 0.6 mL (0.02 mol) and thiosemicarbazide 1.8 g (0.02 mol) was stirred with ethanol (50 mL) at 293 K for 2 h, then add 1-(4-nitrophenyl)ethanone 3.3 g (0.02 mol), then afford the title compound [4.17 g, yield: 87.6%]. Single crystals suitable for X-ray measurements were obtained by recrystallization from acetone and ethanol(1:1) at room temperature.