1-(2,6-Dichloro­phen­yl)indolin-2-one

Muhammad Hanif; Muhammad Rafiq; Muhammad Saleem; Ghulam Qadeer; Wai-Yeung Wong

doi:10.1107/S1600536809005807

. 2009 Feb 25;65(Pt 3):o583. doi: 10.1107/S1600536809005807

1-(2,6-Dichlorophenyl)indolin-2-one

Muhammad Hanif ^a, Muhammad Rafiq ^a, Muhammad Saleem ^b, Ghulam Qadeer ^a,^*, Wai-Yeung Wong ^c,^‡

PMCID: PMC2968669 PMID: 21582238

Abstract

In the molecule of the title compound, C₁₄H₉Cl₂NO, the planar indole ring system [with a maximum deviation of 0.020 (2) Å for the N atom] is oriented at a dihedral angle of 72.17 (3)° with respect to the phenyl ring. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link the molecules. A weak C—H⋯π interaction may further stabilize the structure.

Related literature

For general background, see: Hibino & Choshi (2002 ▶); Somei & Yamada (2003 ▶); Popp (1977 ▶, 1984 ▶). For related structures, see: Chakraborty & Talapatra (1985 ▶); Chakraborty et al. (1985 ▶); De (1992 ▶); De & Kitagawa (1991a ▶,b ▶); Itai et al. (1978 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₉Cl₂NO
M _r = 278.12
Monoclinic,
a = 7.1412 (8) Å
b = 8.0241 (9) Å
c = 11.0510 (13) Å
β = 105.789 (2)°
V = 609.35 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 173 K
0.30 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.755, T _max = 0.902
3710 measured reflections
2328 independent reflections
2295 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.021
wR(F ²) = 0.060
S = 1.06
2328 reflections
163 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ▶), 705 Friedel pairs
Flack parameter: −0.02 (4)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005807/hk2625sup1.cif

e-65-0o583-sup1.cif^{(15.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005807/hk2625Isup2.hkl

e-65-0o583-Isup2.hkl^{(114.4KB, 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
C4—H4A⋯O1ⁱ	0.95	2.55	3.2267 (19)	128
C8—H8A⋯Cg1ⁱⁱ	0.99	2.74	3.6125 (23)	147

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the centroid of the C9–C14 ring.

Acknowledgments

The authors gratefully acknowledge the financial support of the Higher Education Commission, Islamabad, Pakistan.

supplementary crystallographic information

Comment

Indolinones are a class of heterocyclic compounds found in many natural products and in a number of marketed drugs (Hibino & Choshi, 2002; Somei & Yamada, 2003). They have diverse chemical structures and complex physiological and pharmacological actions. The search for potential drugs and their mechanism of action has been difficult because of their complexity. These compounds contain both oxoindole and dioxolane moieties which have independently been seen in other anticonvulsants (Popp, 1977, 1984). The title compound, a chloro analogue, was found to be most potent in the MES test. Since no common target site has yet been established, X-ray analysis was undertaken to search its crystal structure, which may help to understand the mechanism of action at the molecular level.

In the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6), B (N1/C7-C10) and C (C9-C14) are, of course, planar and the dihedral angles between them are A/B = 71.73 (3)°, A/C = 72.43 (3)° and B/C = 1.07 (3)°. So, rings B and C are nearly coplanar. Ring A is oriented with respect to the planar indole ring system at a dihedral angle of 72.17 (3)°. The C8-C9 [1.4955 (19) Å] bond length may be compared with the corresponding values in other indoline nuclei (Itai et al., 1978; Chakraborty & Talapatra, 1985; Chakraborty et al., 1985; De & Kitagawa, 1991a,b; De, 1992).

In the crystal structure, weak intermolecular C-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. The weak C—H···π interaction (Table 1) may further stabilize the structure.

Experimental

For the preparation of the title compound, sodium salt of 2-(2-(2,6-dichloro- phenylamino)phenyl)acetate (3.18 g, 10 mmol) was dissolved in distilled water (50 ml) and heated on a hot plate, until a homogeneous solution obtained, and then filtered to remove the undissolved product. It was poured into concentrated hydrochloric acid (5 ml) diluted with ice water (25 ml) in an Erlenmeyer flask to obtain 2-(2-(2,6-dichlorophenylamino)phenyl)acetic acid. Then, it was stand for 15 min in an ice bath. The crude product was separated and recrystallized in ethanol. 2-(2-(2,6-dichlorophenylamino)phenyl)acetic acid (2.96 g, 10 mmol) was refluxed in methanol (50 ml) in catalytic amount of sulfuric acid. As soon as a methyl ester is formed, it is cyclized to form the title compound, which was recrystallized in ethanol (yield; 79%; m.p. 420-421 K).