(E)-3-(2-Hy­droxy-5-methyl­phenyl­imino)­indolin-2-one

Peng-Fei Zhang; Cai-Feng Bi; Qiang Wang; Jian Zuo; Nan Zhang

doi:10.1107/S1600536811034015

. 2011 Aug 27;67(Pt 9):o2493. doi: 10.1107/S1600536811034015

(E)-3-(2-Hydroxy-5-methylphenylimino)indolin-2-one

Peng-Fei Zhang ^a, Cai-Feng Bi ^a,^*, Qiang Wang ^a, Jian Zuo ^a, Nan Zhang ^a

PMCID: PMC3200761 PMID: 22059043

Abstract

In the title compound, C₁₅H₁₂N₂O₂, the dihedral angle between the two benzene rings is 83.55 (11)° In the crystal, the molecules are linked by O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For general background on Schiff base ligands, see: Guo et al. (2011 ▶); Drozdzak et al. (2005 ▶); Weber et al. (2007 ▶); Liu et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶)

Experimental

Crystal data

C₁₅H₁₂N₂O₂
M _r = 252.27
Monoclinic,
a = 12.6211 (11) Å
b = 8.7100 (7) Å
c = 11.2835 (10) Å
β = 90.780 (1)°
V = 1240.28 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.50 × 0.47 × 0.17 mm

Data collection

CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.956, T _max = 0.985
5982 measured reflections
2182 independent reflections
1449 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.114
S = 1.02
2182 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SMART; data reduction: SAINT (Siemens, 1996 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811034015/ru2008sup1.cif

e-67-o2493-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034015/ru2008Isup2.hkl

e-67-o2493-Isup2.hkl^{(107.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811034015/ru2008Isup3.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
O2—H2⋯O1ⁱ	0.82	1.86	2.6729 (19)	169
N1—H1⋯O2ⁱⁱ	0.86	2.06	2.842 (2)	151

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

Acknowledgments

The authors acknowledge the National Science Foundation of China for its financial support of this project (project No. 21071134).

supplementary crystallographic information

Comment

Being one of the most prevalent sustems in coordination chemistry, Schiff base ligands have received much attention in recent years (Guo et al., 2011), primarily due to their importance in metal complexes with catalytic activities (Drozdzak et al., 2005), special magnetism (Weber et al., 2007) and biological properties, for example, anticancer activities (Liu et al., 2010). In the present paper, the synthesis and structure of a new Schiff base ligand is reported.

The crystal structure of the new ligand is given in Fig.1. The molecular structure of the compound is not coplanar, the dihedral angle between the two benzene rings is 83.55 °, it is almost perpendicular. The bond lengths and angles (Table 1) are within normal values (Allen et al.,1987). In the crystal structure, the adjacent molecules are linked through 0—H···0 and N—H···O hydrogen bonding (Table 2), to generate one-dimensional chain in direction (Fig.2).

Experimental

2,3-indolinedione (5 mmol, 0.736 g) was dissolved in anhydrous ethanol (20 ml), then an anhydrous ethanol solution (10 ml) of 2-amino-4-methylphenol (5 mmol, 0.612 g) was slowly added. The mixture was refluxed for 4 h at 333k,and then cooled down to room temperature. A dark brown solid separated out. The solid was filtered off, washed several times with anhydrous ethanol and dried in vacuum drier. The dark brown single-crystal of the title ligand suitable for X-ray diffraction was trained in anhydrous ethanol at room temperature.