(Z)-3-[(E)-3-Phenyl­allyl­idene]indolin-2-one

Hongming Zhang; Shashidhar Kumar Akubathini; Haribabu Ankati; Ed Biehl

doi:10.1107/S1600536809002037

. 2009 Jan 23;65(Pt 2):o363. doi: 10.1107/S1600536809002037

(Z)-3-[(E)-3-Phenylallylidene]indolin-2-one

Hongming Zhang ^a,^*, Shashidhar Kumar Akubathini ^a, Haribabu Ankati ^a, Ed Biehl ^a

PMCID: PMC2968140 PMID: 21581961

Abstract

The title compound, C₁₇H₁₃NO, synthesized to be tested for neuroprotective activities, consists of an indoline and a phenylallylidene unit with a dihedral angle of 9.0 (1)° between the two ring systems. There are two independent molecules in the asymmetric unit which are connected into a dimer by intermolecular N—H⋯O hydrogen bonds.

Related literature

For the pharmacological properties of 3-substituted indoline-2-ones, see: Sun et al. (2003 ▶); Andreani et al. (2006 ▶); Johnson et al. (2005 ▶). For the synthesis and neuroprotective activities of a series of 3-substituted indoline-2-one derivatives, see: Balderamos et al. (2008 ▶). For the original synthesis of the title compound, see: Elliott & Rivers (1964 ▶). For modified synthetic methods, see: Tacconi & Marinone (1968 ▶); Villemin & Martin (1998 ▶). For the crystal structures of related compounds, see: Zhang et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C₁₇H₁₃NO
M _r = 247.28
Monoclinic,
a = 5.8373 (4) Å
b = 15.3294 (11) Å
c = 14.6516 (10) Å
β = 94.312 (1)°
V = 1307.35 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 (2) K
0.38 × 0.21 × 0.08 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.971, T _max = 0.994
12503 measured reflections
3282 independent reflections
2386 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.132
S = 1.11
3282 reflections
343 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 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 and publCIF (Westrip, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002037/bt2843sup1.cif

e-65-0o363-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002037/bt2843Isup2.hkl

e-65-0o363-Isup2.hkl^{(161KB, 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
N21—H21⋯O2ⁱ	0.86	2.03	2.852 (3)	159
N1—H1⋯O22ⁱⁱ	0.86	2.07	2.893 (3)	161

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

Acknowledgments

The authors are grateful for the grants from the Welch Foundation (N-118) and the DARPA (HR0011–06–1–0032).

supplementary crystallographic information

Comment

It is known that some 3-substituted indoline-2-ones compounds exhibit a variety of pharmacologically important properties such as protein kinase inhibitors (Sun et al., 2003), anti-tumor agents (Andreani et al., 2006) and neuroprotecting agents (Johnson et al., 2005). For studying the biological properties, a series of 3-substituted indoline-2-one derivatives have been synthesized in our lab and their neuroprotective activities have been tested (Balderamos et al., 2008). The results are very promising. To expand our research, a few known compounds were made for test purpose. The title compound was first made by Elliott & Rivers (1964), and modified synthetic methods were reported later (Tacconi & Marinone, 1968; Villemin & Martin, 1998). As a part of our studies on the relationship between the biological activities and solid structures a couple of crystal structures of the derivatives have been carried out (Zhang, et al., 2008, 2009). The title compound consists an indoline and a phenylallylidene unit. The two aromatic rings are slightly twisted with a dihedral angle of 9.0 (1)° (Fig 1). In the crystal the molecules are connected by intermolecular H-bonds between the two independent molecules to form a dimer (Table 1, Fig. 2).

Experimental

The title compound was synthesized by the condensation of trans- cinnamaldehyde (1 mmol) with 2-oxindole (1 mmol) in ethanol (10 ml) in the presence of catalytic amount of piperidine (0.1 mmol). After refluxing for 3 h, the reaction mixture was left to stand for overnight. The resulting crude solid was filtered, washed with cold ethanol (10 ml) and dried. Orange colored single crystals of the compound suitable for x-ray structure determination were recrystallized from ethanol.