1-[(2-Chloro-3-quinol­yl)meth­yl]indoline-2,3-dione

F Nawaz Khan; S Mohana Roopan; Sriramakrishnaswamy Kone; Venkatesha R Hathwar; M Khawar Rauf

doi:10.1107/S1600536810013966

. 2010 Apr 24;66(Pt 5):o1141. doi: 10.1107/S1600536810013966

1-[(2-Chloro-3-quinolyl)methyl]indoline-2,3-dione

F Nawaz Khan ^a, S Mohana Roopan ^a, Sriramakrishnaswamy Kone ^a, Venkatesha R Hathwar ^b, M Khawar Rauf ^c,^*

PMCID: PMC2979291 PMID: 21579189

Abstract

In the title compound, C₁₈H₁₁ClN₂O₂, the isatin and 2-chloro-3-methylquinoline units are both almost planar, with r.m.s. deviations of 0.0075 and 0.0086 Å, respectively, and the dihedral angle between the mean planes of the two units is 83.13 (7)°. In the crystal, a weak intermolecular C—H⋯ O interaction links the molecules into chains along the c axis.

Related literature

For background to the use of N-substituted indole-2,3-diones as intermediates and synthetic precursors for the preparation of heterocyclic compounds, see: Silaicheva et al. (2009 ▶). For the biological activity of N-substituted indole-2,3-diones, see: Vine et al. (2007 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₈H₁₁ClN₂O₂
M _r = 322.74
Monoclinic,
a = 21.4984 (8) Å
b = 5.3061 (2) Å
c = 13.0356 (4) Å
β = 99.718 (3)°
V = 1465.67 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.33 × 0.30 × 0.27 mm

Data collection

Oxford Diffraction Excalibur diffractometer
17920 measured reflections
2724 independent reflections
1731 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.085
S = 0.90
2724 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013966/pv2276sup1.cif

e-66-o1141-sup1.cif^{(19KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013966/pv2276Isup2.hkl

e-66-o1141-Isup2.hkl^{(133.8KB, 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
C17—H17⋯O2ⁱ	0.93	2.48	3.367 (3)	160

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the FIST–DST program at SSCU, IISc. We also thank Professor T. N. Guru Row, IISc, Bangalore, for his help with the data collection. FNK thanks the DST for Fast Track Proposal funding.

supplementary crystallographic information

Comment

N-substituted indole-2,3-diones have been frequently used as intermediates and synthetic precursors for the preparation of a wide variety of heterocyclic compounds (Silaicheva et al., 2009). In addition, they possess different biological activities such as cytotoxicity, antiviral activity and selective caspase inhibitions, etc. (Vine et al., 2007). We have synthesized a novel isatin derivative and determined its crystal structure which is presented in this article.

In the title molecule, the atoms (C11—C18/N2/O1/O2) of the isatin moiety and 2-chloro-3-methylquinoline group (C1—C8/N1/Cl1) are individually planar with maximum r.m.s. deviations of 0.0075 and 0.0086 Å, respectively, from their mean-planes. The dihedral angle between the two ring systems is 83.13 (7)°. The bond distances and angles in the title compound are as expected (Allen et al., 1987). There is a weak intermolecular interaction C17—H17··· O2 linking the molecules into chains along the c-axis.

Experimental

2-Chloro-3-chloromethylquinoline (210 mg, 1 mmol), KO^tBu (112 mg, 1 mmol) and isatin (147 mg, 1 mmol) in tetrahydrofuran (10 ml) were taken in a round bottemed flask and the mixture was refluxed at 70 W for 3 min. Ethylacetate (30 ml) was poured into the reaction mixture and filtered off. The filtrate was subjected to column chromatography packed with silica and ethyl acetate/petroleum ether was used as the eluant (4:1). Crystals of suitable quality were grown by slow evaporation from a solution of the title compound in dichloromethane.