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

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

doi:10.1107/S1600536812005417

. 2012 Mar 3;68(Pt 4):o955–o956. doi: 10.1107/S1600536812005417

(Z)-N-Methyl-2-(5-methyl-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: PMC3343935 PMID: 22590016

Abstract

In the title compound, C₁₁H₁₂N₄OS, an intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the molecules form a helical chain along the a axis through an N—H⋯O hydrogen bond. These chains are extended by an N—H⋯S hydrogen bond and a C—H⋯π interaction into a three-dimensional network.

Related literature

For related structures, see: Ali et al. (2012 ▶); Qasem Ali et al. (2012 ▶, 2011a ▶,b ▶). 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 cytotoxic and anticancer activities of isatin and its derivatives, see: Vine et al. (2009 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₁H₁₂N₄OS
M _r = 248.31
Orthorhombic,
a = 6.2826 (2) Å
b = 10.0341 (3) Å
c = 19.1315 (5) Å
V = 1206.05 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 100 K
0.51 × 0.18 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.879, T _max = 0.967
13743 measured reflections
3780 independent reflections
3463 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.097
S = 1.07
3780 reflections
168 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ▶), with 1584 Friedel pairs
Flack parameter: −0.08 (7)

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/S1600536812005417/is5066sup1.cif

e-68-0o955-sup1.cif^{(22.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005417/is5066Isup2.hkl

e-68-0o955-Isup2.hkl^{(185.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812005417/is5066Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.81 (2)	2.03 (2)	2.8319 (17)	171 (2)
N3—H1N3⋯O1	0.84 (2)	2.079 (19)	2.7525 (17)	136.9 (17)
N4—H1N4⋯S1ⁱⁱ	0.80 (2)	2.85 (2)	3.5538 (13)	148.5 (19)
C3—H3A⋯Cg2ⁱⁱⁱ	0.95	2.62	3.4165 (16)	142

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

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia for an RU research grant (No. 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 fungal 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)-N-methyl-2-(5-nitro-2-oxoindolin-3-ylidene) hydrazinecarbothioamide (Ali et al., 2012). In the present paper we describe the single-crystal X-ray diffraction study of title compound.

In this compound (Fig. 1), the chain N2/N3/C9/S1/N4/C10 connects to the nine-membered 5-methylindolin-2-one ring system at C7. In this chain, C7/N2/N3/C9 and C10/N4/C9/S1 have torsion angles -176.69 (13) and -1.4 (2)°, respectively. The essentially planar conformation of the molecule is maintained by the cyclic intramolecular N3—H1N3···O1 hydrogen-bond (Table 1) [graph set S(6); Bernstein et al., 1995)]. In the crystal, the molecules form a helical chain through an intermolecular N1—H1N1···O1 hydrogen bond and are extended by an N4—H1N4···S1 hydrogen bond and a weak C3—H3A···Cg2 interaction into a three-dimensional network (Table 1, Fig. 2). Cg2 is the centroid of the C1–C6 ring.

Experimental

The Schiff base has 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-methylisatin (0.01 mol) for 2 h. The precipitate formed during reflux was filtered, washed with cold EtOH and recrystallized from hot EtOH (yield 94%, m.p. 551.7–552.2 K). The yellow crystals were grown in acetone–DMF (3:1) by slow evaporation at room temperature.