1-Benzyl-6-chloro­indoline-2,3-dione

Hua-quan Liu; Dong-mei Fan; De-cai Wang; Ping-Kai Ou-yang

doi:10.1107/S1600536811048665

. 2011 Nov 25;67(Pt 12):o3427. doi: 10.1107/S1600536811048665

1-Benzyl-6-chloroindoline-2,3-dione

Hua-quan Liu ^a, Dong-mei Fan ^a, De-cai Wang ^a,^*, Ping-Kai Ou-yang ^a

PMCID: PMC3239061 PMID: 22199909

Abstract

In the title compound, C₁₅H₁₀ClNO₂,the dihedral angle between the mean planes of the benzene and 6-chloroindoline-2,3-dione ring systems, linked through a methylene group, is 81.68 (10)°. In the crystal, molecules are connected by C—H⋯O hydrogen bonds, generating C(6) chains propagating in [010].

Related literature

For general background to isatin derivatives, see: Vine et al. (2007 ▶); Matesic et al. (2008 ▶). For further synthetic details, see: Bouhfid et al. (2005 ▶).

Experimental

Crystal data

C₁₅H₁₀ClNO₂
M _r = 271.69
Triclinic,
a = 7.1870 (14) Å
b = 7.5800 (15) Å
c = 12.012 (2) Å
α = 80.24 (3)°
β = 84.90 (3)°
γ = 79.74 (3)°
V = 633.4 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.916, T _max = 0.971
2520 measured reflections
2322 independent reflections
1837 reflections with I > 2σ(I)
R _int = 0.015
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.155
S = 1.00
2322 reflections
172 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048665/hb6512sup1.cif

e-67-o3427-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048665/hb6512Isup2.hkl

e-67-o3427-Isup2.hkl^{(114.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811048665/hb6512Isup3.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
C9—H9A⋯O1ⁱ	0.93	2.58	3.431 (3)	152

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

Halogenated derivatives of isatin have been found to exhibit cytotoxic and antineoplastic activity(Vine et al., 2007; Matesic et al., 2008). As a part of our studies into the synthesis of isatin derivatives, the title compound (I) 1-benzyl-6-chloroindoline-2,3-dione was synthesized (Bouhfid et al. (2005)). We report herein its crystal structure.

In the title compound, C₁₅H₁₀ClNO₂, the indoline and benzene moieties are linked by a methylene group with a C6—C7(methylene)-N angle of 112.49 (2)° (Fig. 1). The dihedral angle between the mean planes of the benzene and 6-chloroindoline-2,3-dione is 81.68 (10) °. In the crystal structure, C—H···O hydrogen bonds link the molecules (Fig. 2 and Table 1).

Experimental

Isatin(1.47 g, 0.01 mol) was reacted with benzyl bromide (0.02 mol) in the presence of K₂CO₃ (2.76 g, 0.02 mol) and tetrabutylammonium bromide (0.32 g, 0.001 mol) in DMF (60 ml). After 12 h stirring at rt, the precipitate was removed by filtration and purified by recrystallization from ethanol(m.p. 175.2–176.1 °C; yield 70%). The yellow blocks of the title compound were obtained by slow evaporation from ethanol at room temperature.