5-Fluoro-1-(4-meth­oxy­benz­yl)indoline-2,3-dione

Weiyao Wu; Huihui Lin; Chong-Qing Wan; Sheng-Li Cao

doi:10.1107/S1600536811023488

. 2011 Jun 30;67(Pt 7):o1834. doi: 10.1107/S1600536811023488

5-Fluoro-1-(4-methoxybenzyl)indoline-2,3-dione

Weiyao Wu ^a, Huihui Lin ^a, Chong-Qing Wan ^a, Sheng-Li Cao ^a,^*

PMCID: PMC3151828 PMID: 21837201

Abstract

In the title compound, C₁₆H₁₂FNO₃, the dihedral angle between the benzene ring and the plane of the indole ring system is 71.60 (6)°. In the crystal, molecules stack along the b axis through π–π interactions between the adjacent indole-2,3-dione units with a centroid–centroid distance of 3.649 (3) Å. Intermolecular C—H⋯O=C and C—H⋯π interactions further stabilize the structure, forming a three-dimensional framework.

Related literature

For background to the use of 5-fluoroindoline-2,3-dione and its analogues as anti-tumour agents, see: Uddin et al. (2007 ▶); Penthala et al. (2010 ▶). For a related structure, see: Wu et al. (2011 ▶).

Experimental

Crystal data

C₁₆H₁₂FNO₃
M _r = 285.27
Orthorhombic,
a = 17.779 (4) Å
b = 7.1575 (14) Å
c = 21.306 (4) Å
V = 2711.3 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.641, T _max = 0.746
25325 measured reflections
3202 independent reflections
1604 reflections with I > 2σ(I)
R _int = 0.100

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.136
S = 1.01
3202 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2 and SAINT (Bruker, 2007 ▶); 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 PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023488/sj5156sup1.cif

e-67-o1834-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023488/sj5156Isup2.hkl

e-67-o1834-Isup2.hkl^{(157.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811023488/sj5156Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯Cg1ⁱ	0.93	3.03	3.812 (2)	142
C14—H14A⋯O2ⁱⁱ	0.93	2.49	3.345 (2)	153

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

Acknowledgments

The authors are grateful to the National Science Foundation Committee (project No. 20972099) for financial support.

supplementary crystallographic information

Comment

The derivatives of 5-fluoroindoline-2,3-dione and its analogues are widely used as anti-tumor compounds (Uddin et al., 2007; Penthala et al., 2010). Herein, we report the crystal structure of one new derivative of 5-fluoroindoline-2,3-dione.

In the title compound C₁₆H₁₂FNO₃, the indoline moiety links to the 4-methoxybenzene through methylene group with a C5-C7(methylene)-N1 angle of 113.29 (2)° (Fig. 1). The benzene ring and the plane of the indole-2,3-dione exhibit a dihedral angle of 71.60 (6)°. The C5-C7(methylene)-N1 angle and the dihedral angle are comparable to these in the chloro-substituted compound, 5-chloro-1- (4-methoxybenzyl)indoline-2,3-dione, where the corresponding values are 113.86 (2)° and 88.44 (8)° (Wu et al. 2011). Molecules stack along the b axis through π–π stacking interactions between adjacent indole-2,3-dione units with a Cg···Cg distance of 3.649 (3)Å and C15-H15A···Cg contacts, Table 1, form a chain structure, as shown in Fig. 2. The almost parallel chains are further interconnected through C14-H14A···O2═C9 interactions, Table 1, generating a three-dimensional framework, Fig. 2.

Experimental

To an ice-bath cooled solution of 5-fluoroindoline-2,3-dione (0.33 g, 2 mmol) in N,N-dimethylformamide (20 ml) was added potassium carbonate (0.33 g, 2.4 mmol) and potassium iodide (0.07 g, 0.4 mmol) followed by 4-methoxybenzyl chloride (0.32 ml, 2.2 mmol). The reaction mixture was stirred at 110 °C for 3 h. After cooling to room temperature, the reaction mixture was poured into ice water (80 ml). The resulting precipitate was filtered and subsequently purified by column chromatography on silica gel with dichloromethane as an eluent to give the title compound (Rf = 0.81, dichloromethane; m.p. 138-139 °C; yield 78%). Yellow crystals of the title compound were obtained by slow evaporation from the solution of dichloromethane/ethanol 8:2 (v/v) at room temperature after a week.