1,3,3-Tribenzyl­indolin-2-one

Yufang Liu; Bo Liu; Zhenming Dong; Shuo Jin

doi:10.1107/S1600536811042425

. 2011 Oct 22;67(Pt 11):o2998. doi: 10.1107/S1600536811042425

1,3,3-Tribenzylindolin-2-one

Yufang Liu ^a, Bo Liu ^b,^*, Zhenming Dong ^a, Shuo Jin ^a

PMCID: PMC3247398 PMID: 22220016

Abstract

In the title compound, C₂₉H₂₅NO, the dihedral angles between the indolin-2-one ring system and the three benzene rings are 62.78 (9), 31.69 (9) and 80.94 (9)°.

Related literature

For general background to the use of indoline-2-one compounds as precursors for the synthesis of antitumor agents, see: Wang et al. (2011 ▶). For a related structure, see: Katritzky et al. (1997 ▶).

Experimental

Crystal data

C₂₉H₂₅NO
M _r = 403.50
Monoclinic,
a = 8.3387 (9) Å
b = 9.6266 (10) Å
c = 13.9398 (14) Å
β = 99.442 (2)°
V = 1103.8 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.979, T _max = 0.986
4797 measured reflections
2073 independent reflections
1731 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.076
S = 1.05
2073 reflections
281 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811042425/hg5107sup1.cif

e-67-o2998-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042425/hg5107Isup2.hkl

e-67-o2998-Isup2.hkl^{(101.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811042425/hg5107Isup3.cml

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

Acknowledgments

The authors are grateful to the National Science Foundation (BL, No. 21072019) for support of this work and Dr Maosen Yuan of Northwest A & F University for the data collection and structure determination.

supplementary crystallographic information

Comment

Indoline-2-one compounds have been widely explored as precursors for the synthesis of antitumor agent (Wang et al., 2011). In the course of exploring new antitumor medicine, we obtained a intermediate compound C₂₉H₂₅NO (I), the synthesis and structure of which are reported here.

The title compound contain four ring planes, three benzene rings and one indoline-2-one ring. The interplanar dihedral angle between the indolin-2-one ring plane and the three benzene ring planes are 62.78 (9)°, 31.69 (9)° and 80.94 (9)\ respectively.

The molecules of (I) crystallize in the space group P2₁ which is different from that of 3-(1,2-diphenylethylidene)indolin-2-one (P-1) (Katritzky et al. 1997).

Experimental

Indolin-2-one (0.50 g, 3.76 mmol) was dissolved in THF (20 mL) and KOH (0.80 g, 14.3 mmol) was slowly added. After heating the stirred mixture at reflux temperature for 30 min, a solution of 1-(chloromethyl)benzene (2.00 g, 15.9 mmol) in THF was slowly added and the refluxing continued for 2 h. The mixture was then cooled to 333 K and poured into water (200 mL) and was extracted with chloroform and dried over Na₂SO₄. After removing the solvent, the crude product was purified by column chromatography on silica gel, affording the title compound (yield: 0.23 g, 15%). The compound was then dissolved in THF, and colorless crystals were formed on slow evaporation at room temperature over one week.