2,2-Bis(1H-indol-3-yl)indolin-3-one

Zhao-Hao Li; Jing Xu; Wen-Liang Wu; Wei-Ping Su

doi:10.1107/S1600536809017553

. 2009 May 20;65(Pt 6):o1353. doi: 10.1107/S1600536809017553

2,2-Bis(1H-indol-3-yl)indolin-3-one

Zhao-Hao Li ^a,^b, Jing Xu ^a,^b, Wen-Liang Wu ^a,^b, Wei-Ping Su ^b,^*

PMCID: PMC2969773 PMID: 21583204

Abstract

In the title molecule, C₂₄H₁₇N₃O, the mean plane of the indolone ring forms dihedral angles of 112.0 (1) and 103.1 (1)° with the planes of the two indole rings. The dihedral angle between the mean planes of the two indole rings is 63.5 (1)°. In the crystal structure, molecules are linked via intermolecular N—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the ab plane.

Related literature

For the applications of indole derivatives, see: Ramesh et al. (2009 ▶). For the isolation of the title compound as a natural product, see: Ganachaud et al. (2008 ▶); Stull et al. (1995 ▶).

Experimental

Crystal data

C₂₄H₁₇N₃O
M _r = 363.41
Monoclinic,
a = 10.559 (4) Å
b = 8.931 (3) Å
c = 19.899 (7) Å
β = 98.480 (6)°
V = 1856.1 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.40 × 0.35 × 0.15 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.968, T _max = 0.988
14004 measured reflections
4245 independent reflections
3606 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.118
S = 1.06
4245 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017553/lh2811sup1.cif

e-65-o1353-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017553/lh2811Isup2.hkl

e-65-o1353-Isup2.hkl^{(208KB, 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
N2—H2B⋯O1ⁱ	0.86	2.12	2.9412 (17)	159
N3—H3B⋯O1ⁱⁱ	0.86	2.18	2.9830 (16)	156

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

Acknowledgments

This work was supported by the Natural Science Foundation of Fujian province (grant No. 2006 J0273) and the ‘One Hundred Talent’ Projects from the Chinese Academy of Sciences.

supplementary crystallographic information

Comment

Indole derivatives are used as bioactive drugs and they exibit anti-allergic, central nervous system depressant and muscle relaxant properties (Ramesh et al., 2009). The title compound is a natural product that has been isolated from bacterial sources (Stull et al.., 1995; Ganachaud et al.., 2008). Recently, we found different indole derivatives could be formed by oxidation solely on the basis of the reaction solvent and temperature. As part of our studies, we report herein the synthesis and crystal structure of the title compound (I) (Fig. 1).

The title compound is a trimeric condensation product of indole through the formation of a quaternary carbon (C8) centre. The indolone ring forms dihedral angle of 112.0 (1)° and 103.1 (1)°, respectively, with the two indole rings (C9/C10/C11/C12/C13/C14/C15/C16/N2) and (C17/C18/C19/C20/C21/C22/C23/C24/N3). The mean planes of the two indole form a dihedral angle of 63.5 (1)°. In the crystal structure, the carbonyl atom O1 acts as a bifurcated acceptor for the N-H groups of atoms N2 and N3 to form a two-dimensional network parallel to the ab plane (Table 1, Fig. 2).

Experimental

The title compound was obtained from a mixture of 1H-indole (78 mg) with ^tBuCOOH (0.18 ml) and H₃PMo₁₂O₁₄ (9 mg) in toluene (1 ml) and CH₃COOH (1 ml) under a nitrogen atmosphere at room temperature for 24 h. The crude product was isolated and purified by silica gel columnchromatography. Yellow prism-shaped crystals of (I) suitable for X-ray diffraction were grown by slow evaporation of a dichloromethane solution at room temperature.