Tris(3-hy­droxy­imino-1-methyl­indolin-2-one) monohydrate

Yanqing Miao; Xiaoqing Zhang; Chunye Liu; Jing You

doi:10.1107/S1600536811015418

. 2011 May 7;67(Pt 6):o1291. doi: 10.1107/S1600536811015418

Tris(3-hydroxyimino-1-methylindolin-2-one) monohydrate

Yanqing Miao ^a,^*, Xiaoqing Zhang ^a, Chunye Liu ^a, Jing You ^a

PMCID: PMC3120467 PMID: 21754698

Abstract

There are three independent 3-hydroxyimino-1-methylindolin-2-one molecules and a water molecule in the asymmetric unit of the title compound, 3C₉H₈N₂O₂·H₂O. The crystal packing is stablized by O—H⋯O and O—H⋯Nhydrogen bonds between 3-hydroxyimino-1-methylindolin-2-one molecules and the water molecule and weak π–π stacking interactions [centroid–centroid distances in the range 3.446 (2)–3.983 (2) Å], forming a two-dimensional network.

Related literature

For the anti-bacterial, anti-virus and neuroprotective activity of indolin-2-one derivatives, see: Chen et al. (2009a ▶,b ▶, 2010a ▶,b ▶). For standard bond lengths, see Allen et al. (1987 ▶).

Experimental

Crystal data

3C₉H₈N₂O₂·H₂O
M _r = 546.54
Triclinic,
a = 8.920 (3) Å
b = 10.811 (4) Å
c = 14.915 (5) Å
α = 91.335 (3)°
β = 101.013 (3)°
γ = 112.784 (3)°
V = 1294.1 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.36 × 0.28 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2005 ▶) T _min = 0.944, T _max = 0.986
7872 measured reflections
4512 independent reflections
3154 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.140
S = 1.05
4512 reflections
362 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015418/jj2082sup1.cif

e-67-o1291-sup1.cif^{(22.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015418/jj2082Isup2.hkl

e-67-o1291-Isup2.hkl^{(221KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811015418/jj2082Isup3.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
O7W—H7WA⋯O6ⁱ	0.96	1.82	2.752 (3)	164
O1—H1B⋯N1ⁱⁱ	0.82	2.11	2.780 (3)	139
O7W—H7WB⋯O6ⁱⁱⁱ	0.96	2.02	2.958 (3)	165
O7W—H7WB⋯N5ⁱⁱⁱ	0.96	2.59	3.181 (3)	120
O3—H3C⋯O7W	0.82	1.78	2.579 (3)	165
O5—H5C⋯O4	0.82	2.05	2.753 (3)	144

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

Acknowledgments

This work was supported financially by grants from the Scientific Research Plan Projects of Shaanxi Province Department of Health (2010D54), the Natural Science Research Plan Projects of Shaanxi Science and Technology Department (SJ08B19) and the Scientific Research Plan Projects of Shaanxi Education Department (09 J K709).

supplementary crystallographic information

Comment

Isatin derivatives attracted much attention related to their anti-bacterial, anti-virus and neuroprotection properties (Chen et al., 2009a; Chen et al., 2009b; Chen et al., 2010a; Chen et al.,2010b). 3-(Hydroxyimino)-1-methylindolin-2-one, a related structure, has been synthesized by a condensation reaction of N-methyl isatin and hydroxylamine. In this paper we report the X-ray crystal structure of the title compound, a related derivative of these bioactive compounds.

In the title compound, 3(C₉H₈N₂O₂), H₂O, there are three independent 3-(hydroxyimino)-1-methylindolin-2-one planar molecules and a water molecule in the asymmetric unit (Fig. 1). Bond lengthas and angles are in normal ranges (Allen et al., 1087). Crystal packing is stablized by O—H···O hydrogen bonds between 3-(hydroxyimino)-1-methylindolin-2-one molecules and the water molecule and weak π—π stacking interactions (Table 2) forming a two-dimensional network (Fig. 2).

Experimental

N-methyl isatin (1 mmol) was dissolved in methanol (20 ml), 10 ml me thanol solution of 1.2 mmol hydroxylamine was added dropwise, 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), giving the title compound. 30 mg of the title compound was dissolved in 30 ml me thanol and the solution was kept at room temperature for 4 d, natural evaporation gave yellow single crystals suitable for X-ray analysis.