3-(2-Ethyl-2-phenyl­hydrazin-1-yl­idene)indolin-2-one

Uzma Ashiq; Rifat Ara Jamal; Hina Ismail; Khalid Mohammed Khan; Sammer Yousuf

doi:10.1107/S1600536812047988

. 2012 Nov 28;68(Pt 12):o3473. doi: 10.1107/S1600536812047988

3-(2-Ethyl-2-phenylhydrazin-1-ylidene)indolin-2-one

Uzma Ashiq ^a,^*, Rifat Ara Jamal ^a, Hina Ismail ^a, Khalid Mohammed Khan ^b, Sammer Yousuf ^b,^*

PMCID: PMC3589046 PMID: 23476282

Abstract

In the title compound, C₁₆H₁₅N₃O, the dihedral angle between the indole ring system (r.m.s. deviation = 0.020 Å) and the phenyl ring is 14.49 (9)°. The molecular conformation is supported by an intramolecular C—H⋯O interaction, which closes an S(7) ring. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R ₂ ²(8) loops.

Related literature

For a related structure, see: Jamal et al. (2011 ▶). For background to Schiff bases, see: Chaluvaraju & Zaranappa (2011 ▶); Khan et al. (2009 ▶).

Experimental

Crystal data

C₁₆H₁₅N₃O
M _r = 265.31
Monoclinic,
a = 9.463 (2) Å
b = 17.303 (4) Å
c = 8.5403 (18) Å
β = 104.427 (5)°
V = 1354.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 273 K
0.35 × 0.18 × 0.06 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.971, T _max = 0.995
7875 measured reflections
2448 independent reflections
1783 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.116
S = 1.08
2448 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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

Click here for additional data file.^{(18.4KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047988/hb6996sup1.cif

e-68-o3473-sup1.cif^{(18.4KB, cif)}

Click here for additional data file.^{(120.3KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047988/hb6996Isup2.hkl

e-68-o3473-Isup2.hkl^{(120.3KB, hkl)}

Click here for additional data file.^{(5.4KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812047988/hb6996Isup3.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
C15—H15A⋯O1	0.97	2.21	2.916 (2)	128
N1—H1A⋯O1ⁱ	0.86	1.99	2.844 (2)	172

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are thankful to the Higher Education Commission (HEC) Pakistan for financial support under the National Research Grants Program for Universities (grant No. 20–1862/R&D/10).

supplementary crystallographic information

Comment

Isatin and its Schiff bases form an important class of organic compounds with a variety of biological activities. Many studies have reported regarding the biological activities of Schiff bases, including their antifungal, antibacterial, anticancer and antiglycation (Khan et al., 2009; Chaluvaraju & Zaranappa. 2011). In order to study the biological activity of title compound, we undertook the synthesis of title compound and report its crystal structure in this paper (Fig. 1). The title compound I was found a potent DPPH radical scavenger.

The title compound, C₁₆H₁₅N₃O is an structural analogue of our previously published compound 3-amino-N'-(2-oxoindolin-3-ylidene)- benzohydrazide (Jamal et al., 2011) with the difference that the keto amine phenyl moiety is replaced by phenyl ring (C9–C14) and N3 is substituted with ethyl group (C15–C16). The phenyl and indole rings are each planar with the dihedral angle of 14.49 (9)° between them. The geometry of molecule is stabilized by an intramolecular C15—H15A···O1 hydrogen bond. In the crystal molecules are consolidated by intermolecular N1—H1A···O1 hydrogen bond (Fig. 2. symmetry codes as in Table 2).

Experimental

To a solution of 2,3-Indolinedione (10 mmol, 1.47 g) in 15 ml of ethanol with few drops of glacial acetic acid and 1-ethyl-1-phenylhydrazine (10 mmol,1.36 g) in 15 ml e thanol were added. The mixture was refluxed for 24 h and a solid was obtained upon removal of the solvent by rotary evaporation.The resulting solid was washed with hexane to afford the title compound. Yellow plates were grown from a mixture of ethanol and methanol (1:1) solvents by slow evaporation at room temperature.