(Z)-N-Methyl-2-(5-nitro-2-oxoindolin-3-yl­idene)hydrazinecarbothio­amide

Amna Qasem Ali; Naser Eltaher Eltayeb; Siang Guan Teoh; Abdussalam Salhin; Hoong-Kun Fun

doi:10.1107/S1600536812001183

. 2012 Mar 3;68(Pt 4):o953–o954. doi: 10.1107/S1600536812001183

(Z)-N-Methyl-2-(5-nitro-2-oxoindolin-3-ylidene)hydrazinecarbothioamide

Amna Qasem Ali ^a,^b, Naser Eltaher Eltayeb ^c,^‡, Siang Guan Teoh ^a,^*, Abdussalam Salhin ^a, Hoong-Kun Fun ^d,^§

PMCID: PMC3343934 PMID: 22590015

Abstract

In the title compound, C₁₀H₉N₅O₃S, an intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked via N—H⋯S hydrogen bonds into a zigzag chain along the b axis. C—H⋯O interactions are observed between the chains.

Related literature

For related structures, see: Qasem Ali et al. (2011a ▶,b ▶); Ferrari et al. (2002 ▶); Pervez et al. (2010 ▶); Ramzan et al. (2010 ▶). For various biological activities of Schiff bases, see: Bhandari et al. (2008 ▶); Bhardwaj et al. (2010 ▶); Pandeya et al. (1999 ▶); Sridhar et al. (2002 ▶); Suryavanshi & Pai (2006 ▶). For the cytotoxic and anticancer activity of isatin and its derivatives, see: Vine et al. (2009 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₀H₉N₅O₃S
M _r = 279.28
Monoclinic,
a = 4.6316 (4) Å
b = 9.3157 (8) Å
c = 26.458 (2) Å
β = 94.485 (2)°
V = 1138.09 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 100 K
0.36 × 0.12 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.900, T _max = 0.979
10734 measured reflections
2710 independent reflections
2177 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.102
S = 1.10
2710 reflections
185 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812001183/is5048sup1.cif

e-68-0o953-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001183/is5048Isup2.hkl

e-68-0o953-Isup2.hkl^{(133.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812001183/is5048Isup3.cml

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—H1N3⋯O1	0.84 (3)	2.02 (3)	2.697 (2)	137 (3)
N1—H1N1⋯S1ⁱ	0.81 (3)	2.52 (3)	3.320 (2)	171 (3)
C2—H2A⋯O1ⁱⁱ	0.95	2.39	3.317 (3)	165
C10—H10A⋯O2ⁱⁱⁱ	0.98	2.56	3.079 (3)	113

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

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia for the RU research grant (1001/PKIMIA/815067). AQA thanks the Ministry of Higher Education and the University of Sabha (Libya) for a scholarship.

supplementary crystallographic information

Comment

Isatin (2,3-dioxindole) is an endogenous compound identified in humans, and its effect has been studied in a variety of systems. Biological properties of isatin and its derivatives include a range of actions in the brain, offer protection against bacterial (Suryavanshi & Pai, 2006) and antifungal infections and possess anticonvulsant, anti-HIV (Pandeya et al., 1999), anti-depressant and anti-inflammatory activities (Bhandari et al., 2008). Recently, we reported the crystal structure of (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide (Qasem Ali et al., 2011a). In the present paper we describe the single-crystal X-ray diffraction study of title compound, Fig. 1.

In this compound (Fig. 1), the chain N2/N3//C9/S1/N4/C10 connected to the nine-membered 5-nitroindolin-2-one ring system in C7. In this chain, C7—N2—N3—C9 and C10—N4—C9—S1 have torsion angles 177.82 (19) and -0.9 (3)°, respectively. The essentially planar conformation of the molecule is maintained by an intramolecular N3—H1N3···O1 hydrogen bond (Table 1) with a graph-set S(6) (Bernstein et al., 1995) In the crystal, molecules are linked via an intermolecular N1—H1N1···S1ⁱ hydrogen bond into an infinite one-dimensional chain along the b axis (Table 1 and Fig. 2). C2—H2A···O1ⁱⁱ and C10—H10A···O2ⁱⁱⁱ hydrogen bonds (Table 1) are also observed between the chains.

Experimental

The Schiff base have been synthesized by refluxing the reaction mixture of hot ethanolic solution (30 ml) of 5-methyl-3-thiosemicarbazide (0.01 mol) and hot ethanolic solution (30 ml) of 5-nitroisatin (0.01 mol) for 2 hrs. The precipitate formed during reflux was filtered, washed with cold EtOH and recrystallized from hot EtOH (yield 80%, m.p. 579.8–580.3 K). The orange crystals were grown in an acetone-DMF (3:1) solution by slow evaporation at room temperature.