1-(Morpholino­meth­yl)indoline-2,3-dione

Ying Tang; Jie Zhang; Yanqing Miao; Gang Chen

doi:10.1107/S1600536810023160

. 2010 Jun 23;66(Pt 7):o1748. doi: 10.1107/S1600536810023160

1-(Morpholinomethyl)indoline-2,3-dione

Ying Tang ^a, Jie Zhang ^a, Yanqing Miao ^b, Gang Chen ^a,^*

PMCID: PMC3006973 PMID: 21587964

Abstract

In the title compound, C₁₃H₁₄N₂O₃, the morpholine ring displays a chair conformation, with the (2,3-dioxoindolin-1-yl)methyl group in an equatorial position. The crystal structure is stabilized by intermolecular C—H⋯O hydrogen bonds.

Related literature

For the synthesis of isatin-N-Mannich bases, see: Varma & Nobles ((1966 ▶). For the bioactivity of isatin derivatives, see: Glover et al. (1980 ▶, 1988 ▶); Maysinger et al. (1980 ▶).

Experimental

Crystal data

C₁₃H₁₄N₂O₃
M _r = 246.26
Monoclinic,
a = 11.608 (2) Å
b = 8.2818 (17) Å
c = 12.595 (3) Å
β = 100.20 (3)°
V = 1191.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.26 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.979, T _max = 0.984
7614 measured reflections
3556 independent reflections
2275 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.144
S = 0.99
3556 reflections
171 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023160/rz2460sup1.cif

e-66-o1748-sup1.cif^{(16.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023160/rz2460Isup2.hkl

e-66-o1748-Isup2.hkl^{(154.9KB, 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
C6—H6A⋯O1ⁱ	0.93	2.47	3.349 (2)	158
C5—H5A⋯O2ⁱⁱ	0.93	2.52	3.216 (2)	131

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

Acknowledgments

This work was supported financially by two grants from the National Science Foundation of China (No. 50874092) and the Natural Science Research Plan Projects of Shaanxi Science and Technology Department (SJ08B20).

supplementary crystallographic information

Comment

Isatin has draw great attention from being discovered as a component of endogenous monoamine oxidase (MAO) inhibitory activity (tribulin) and subsequently identified as a selective inhibitor of MAO B at low concentrations (Glover et al., 1980, 1988). In the following years, many isatin derivatives, such as isatin hydrazono, isatin Mannich bases and isatin based spiroazetidinones, have also been reported to possess anticonvulsant activity (Maysinger, et al., 1980). Herein we report the synthesis and crystal structure of the title compound.

The X-ray structural analysis confirmed the assignment of the structure from spectroscopic data. The molecular structure of the title compound is depicted in Fig. 1. Geometric parameters of the title compound are in the usual ranges. The morpholin ring displays a typical chair conformation, with the (2,3-dioxoindolin-1-yl)methyl group in equatorial position. In the crystal structure, the molecules are linked into a three-dimensional network by C—H···O hydrogen bonds (Table 1).

Experimental

The title compound was synthesized according the literature method (Varma & Nobles, 1966). Isatin (1 mmol), formaldehyde (1.2 mmol) and morpholin (1.2 mmol) were dissolved in methanol (20 ml). The mixture was refluxed until the disappearance of isatin, as evidenced by thin-layer chromatography. The solvent was removed in vacuo and the residue was separated by column chromatography (silica gel, petroleum ether/ethyl acetate = 1:1 v/v), giving the title compound. ¹H-NMR (D₆—DMSO, 400 MHz): 7.61 (2H, m), 7.15 (1H, t, J = 7.2 Hz), 7.09 (1H, d, J = 8.0 Hz), 4.45 (2H, s), 3.70 (4H, t, J = 4.8 Hz), 2.63 (4H, t, J = 4.8 Hz); MS (EI) m/z: 246 (M⁺). 20 mg of the title compound was dissolved in 50 ml methanol and the solution was kept at room temperature for 4 d. Slow evaporation of the solvent gave orange single crystals of the title compound suitable for X-ray analysis.