6-Hydr­oxy-3-(hydroxy­imino)indolin-2-one

Yu, H.

doi:10.1107/S1600536809034321

organic compounds

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Volume 65| Part 10| October 2009| Page o2328

doi:10.1107/S1600536809034321

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6-Hydroxy-3-(hydroxyimino)indolin-2-one

Hui-ling Yu ^a ^*

^aYibin Vocational & Technical College, Si chuan, People's Republic of China
^*Correspondence e-mail: cnyhl@tom.com

(Received 20 August 2009; accepted 27 August 2009; online 5 September 2009)

In the title compound, C₈H₆N₂O₃, the indol-2-one system is almost planar [maximum deviation = 0.010 (3) Å]. In the crystal structure, intermolecular N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds link the molecules into a three-dimensional network. π–π contacts between the indole ring systems [centroid–centroid distances = 3.494 (1), 3.731 (1) and 3.736 (1) Å] may further stabilize the structure.

Related literature

For the biological and pharmacological properties of isatin-3-oxime derivatives, see: Pinto et al. (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₈H₆N₂O₃
M_r = 178.15
Monoclinic, P 2₁ /c
a = 7.4160 (15) Å
b = 7.1240 (14) Å
c = 14.111 (3) Å
β = 95.21 (3)°
V = 742.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 294 K
0.30 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.963, T_max = 0.988
2787 measured reflections
1350 independent reflections
994 reflections with I > 2σ(I)
R_int = 0.068
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.172
S = 1.00
1350 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.86	2.05	2.854 (4)	156
O1—H1C⋯N1ⁱⁱ	0.96	2.52	3.466 (4)	168
O3—H3A⋯O2ⁱⁱⁱ	0.82	2.00	2.753 (3)	152
Symmetry codes: (i) -x+1, -y-1, -z+1; (ii) x, y+1, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034321/hk2760sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809034321/hk2760Isup2.hkl

checkCIF report

Comment top

The title compound is one kind of important isatin-3-oxime derivatives, which displays diverse biological and pharmacological properties (Pinto et al., 2008). We report herein its crystal structure.

In the molecule of the title compound, (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The indole ring system is planar with a maximum deviation of -0.010 (3) Å for atom C2. Atoms O1, O2, O3 and N2 are 0.005 (3), -0.059 (3), -0.184 (3) and -0.085 (3) Å away from the plane of the indole ring system, respectively.

In the crystal structure, intermolecular N-H···O, O-H···N and O-H···O hydrogen bonds (Table 1) link the molecules into a three-dimensional network, in which they may be effective in the stabilization of the structure. The π–π contacts between the indole rings, Cg1—Cg1ⁱ, Cg2—Cg2ⁱⁱ and Cg1—Cg2ⁱ [symmetry codes: (i) 1 - x, 1 - y, -z, (ii) 2 - x, 1 - y, -z, where Cg1 and Cg2 are centroids of the rings (N1/C4/C5/C7/C8) and (C1-C6), respectively] may further stabilize the structure, with centroid-centroid distances of 3.494 (1), 3.731 (1) and 3.736 (1) Å, respectively.

Related literature top

For the biological and pharmacological properties of isatin-3-oxime derivatives, see: Pinto et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, 2-(hydroxyimino)-N-(3-hydroxyphenyl)- acetamide (1 mmol), 1-n-butyl-3-methylimidazolium chloride (0.5 mmol) and 2,2,2-trifluoroacetic acid (0.05 mmol) were added into a sealed flask. The mixture was stirred for 90 min and the temperature maintained at 408 K. After the completion of reaction, ether was used to extract organic compounds from the ionic liquid phase, and the combined organic layers were concentrated under reduced pressure. Product purification was performed by column chromatography. Crystals suitable for X-ray analysis were obtained by dissolving the title compound (0.1 g) in ethyl acetate (10 ml) and evaporating the solvent slowly at room temperature for 2 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

6-Hydroxy-3-(hydroxyimino)indolin-2-one top

Crystal data top

C₈H₆N₂O₃	F(000) = 368
M_r = 178.15	D_x = 1.594 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.4160 (15) Å	θ = 9–13°
b = 7.1240 (14) Å	µ = 0.13 mm⁻¹
c = 14.111 (3) Å	T = 294 K
β = 95.21 (3)°	Block, yellow
V = 742.4 (3) Å³	0.30 × 0.30 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	994 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.068
Graphite monochromator	θ_max = 25.3°, θ_min = 2.8°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −8→8
T_min = 0.963, T_max = 0.988	l = −16→16
2787 measured reflections	3 standard reflections every 120 min
1350 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.172	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.08P)² + 0.6P] where P = (F_o² + 2F_c²)/3
1350 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₈H₆N₂O₃	V = 742.4 (3) Å³
M_r = 178.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4160 (15) Å	µ = 0.13 mm⁻¹
b = 7.1240 (14) Å	T = 294 K
c = 14.111 (3) Å	0.30 × 0.30 × 0.10 mm
β = 95.21 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	994 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.068
T_min = 0.963, T_max = 0.988	3 standard reflections every 120 min
2787 measured reflections	intensity decay: 1%
1350 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.172	H-atom parameters constrained
S = 1.00	Δρ_max = 0.44 e Å⁻³
1350 reflections	Δρ_min = −0.50 e Å⁻³
118 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.9722 (3)	0.3850 (3)	0.61373 (16)	0.0540 (7)
H1C	0.8846	0.4824	0.5992	0.081*
O2	0.5104 (3)	−0.3981 (3)	0.38450 (15)	0.0518 (6)
O3	0.6534 (3)	0.1382 (3)	0.29758 (15)	0.0573 (7)
H3A	0.6170	0.1652	0.2427	0.086*
N1	0.6497 (4)	−0.2911 (4)	0.52693 (17)	0.0446 (7)
H1A	0.6331	−0.3880	0.5615	0.054*
N2	0.6071 (3)	−0.0423 (4)	0.31580 (17)	0.0443 (7)
C1	0.8929 (4)	0.2147 (5)	0.5948 (2)	0.0489 (8)
C2	0.8858 (4)	0.0912 (5)	0.6684 (2)	0.0504 (9)
H2B	0.9338	0.1245	0.7292	0.060*
C3	0.8071 (4)	−0.0837 (5)	0.6524 (2)	0.0458 (8)
H3B	0.8021	−0.1699	0.7015	0.055*
C4	0.7367 (4)	−0.1255 (4)	0.5612 (2)	0.0381 (7)
C5	0.7418 (4)	0.0035 (4)	0.48642 (18)	0.0369 (7)
C6	0.8213 (4)	0.1782 (4)	0.5024 (2)	0.0424 (7)
H6A	0.8263	0.2660	0.4539	0.051*
C7	0.5958 (4)	−0.2790 (4)	0.4338 (2)	0.0387 (7)
C8	0.6537 (4)	−0.0880 (4)	0.40277 (19)	0.0352 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0682 (15)	0.0357 (12)	0.0553 (14)	−0.0148 (11)	−0.0103 (11)	−0.0125 (10)
O2	0.0762 (15)	0.0374 (13)	0.0403 (12)	−0.0061 (11)	−0.0038 (11)	−0.0018 (10)
O3	0.0793 (16)	0.0455 (14)	0.0451 (13)	−0.0082 (12)	−0.0054 (11)	0.0099 (10)
N1	0.0608 (16)	0.0344 (14)	0.0371 (13)	0.0006 (12)	−0.0042 (11)	0.0031 (11)
N2	0.0558 (16)	0.0358 (14)	0.0411 (14)	0.0023 (12)	0.0034 (12)	0.0048 (11)
C1	0.0478 (18)	0.0425 (18)	0.0549 (19)	0.0001 (15)	−0.0036 (15)	−0.0128 (15)
C2	0.0521 (18)	0.058 (2)	0.0383 (16)	0.0025 (16)	−0.0081 (13)	−0.0096 (16)
C3	0.0490 (18)	0.051 (2)	0.0354 (16)	0.0054 (15)	−0.0063 (13)	0.0016 (14)
C4	0.0381 (15)	0.0380 (16)	0.0370 (15)	0.0066 (13)	−0.0027 (12)	−0.0006 (12)
C5	0.0402 (15)	0.0362 (16)	0.0335 (15)	0.0065 (13)	0.0001 (11)	−0.0005 (12)
C6	0.0487 (17)	0.0354 (16)	0.0428 (16)	0.0011 (14)	0.0022 (13)	−0.0016 (13)
C7	0.0478 (16)	0.0317 (15)	0.0353 (15)	0.0039 (13)	−0.0028 (12)	−0.0034 (12)
C8	0.0395 (15)	0.0333 (15)	0.0321 (14)	0.0050 (12)	0.0000 (11)	0.0010 (12)

Geometric parameters (Å, º) top

O1—C1	1.364 (4)	C1—C6	1.387 (4)
O1—H1C	0.9600	C2—C3	1.386 (5)
O2—C7	1.234 (3)	C2—H2B	0.9300
O3—H3A	0.8200	C3—C4	1.376 (4)
N1—C4	1.409 (4)	C3—H3B	0.9300
N1—C7	1.342 (4)	C4—C5	1.402 (4)
N1—H1A	0.8600	C5—C6	1.387 (4)
N2—O3	1.361 (3)	C5—C8	1.451 (4)
N2—C8	1.286 (4)	C6—H6A	0.9300
C1—C2	1.365 (5)	C7—C8	1.504 (4)

C1—O1—H1C	109.2	C3—C4—C5	121.9 (3)
N2—O3—H3A	109.5	C3—C4—N1	128.7 (3)
C4—N1—H1A	124.2	C5—C4—N1	109.4 (2)
C7—N1—C4	111.6 (2)	C6—C5—C4	120.4 (3)
C7—N1—H1A	124.2	C6—C5—C8	133.5 (3)
C8—N2—O3	111.6 (3)	C4—C5—C8	106.1 (3)
O1—C1—C2	118.0 (3)	C5—C6—C1	116.2 (3)
O1—C1—C6	118.2 (3)	C5—C6—H6A	121.9
C2—C1—C6	123.8 (3)	C1—C6—H6A	121.9
C1—C2—C3	120.0 (3)	O2—C7—N1	126.8 (3)
C1—C2—H2B	120.0	O2—C7—C8	127.1 (3)
C3—C2—H2B	120.0	N1—C7—C8	106.0 (2)
C4—C3—C2	117.7 (3)	N2—C8—C5	136.4 (3)
C4—C3—H3B	121.1	N2—C8—C7	116.6 (3)
C2—C3—H3B	121.1	C5—C8—C7	106.8 (2)

O1—C1—C2—C3	−179.7 (3)	C2—C1—C6—C5	−1.1 (5)
C6—C1—C2—C3	1.4 (5)	C4—N1—C7—O2	−177.1 (3)
C1—C2—C3—C4	−0.5 (5)	C4—N1—C7—C8	0.5 (3)
C2—C3—C4—C5	−0.6 (4)	O3—N2—C8—C5	0.5 (5)
C2—C3—C4—N1	−179.6 (3)	O3—N2—C8—C7	175.0 (2)
C7—N1—C4—C3	178.8 (3)	C6—C5—C8—N2	−4.9 (6)
C7—N1—C4—C5	−0.3 (3)	C4—C5—C8—N2	175.2 (3)
C3—C4—C5—C6	0.9 (4)	C6—C5—C8—C7	−179.7 (3)
N1—C4—C5—C6	−180.0 (3)	C4—C5—C8—C7	0.3 (3)
C3—C4—C5—C8	−179.2 (3)	O2—C7—C8—N2	1.1 (5)
N1—C4—C5—C8	0.0 (3)	N1—C7—C8—N2	−176.6 (3)
C4—C5—C6—C1	0.0 (4)	O2—C7—C8—C5	177.2 (3)
C8—C5—C6—C1	−180.0 (3)	N1—C7—C8—C5	−0.5 (3)
O1—C1—C6—C5	−180.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.05	2.854 (4)	156
O1—H1C···N1ⁱⁱ	0.96	2.52	3.466 (4)	168
O3—H3A···O2ⁱⁱⁱ	0.82	2.00	2.753 (3)	152

Symmetry codes: (i) −x+1, −y−1, −z+1; (ii) x, y+1, z; (iii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₈H₆N₂O₃
M_r	178.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	7.4160 (15), 7.1240 (14), 14.111 (3)
β (°)	95.21 (3)
V (Å³)	742.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.30 × 0.30 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.963, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	2787, 1350, 994
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.172, 1.00
No. of reflections	1350
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.50

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.05	2.854 (4)	156
O1—H1C···N1ⁱⁱ	0.96	2.52	3.466 (4)	168
O3—H3A···O2ⁱⁱⁱ	0.82	2.00	2.753 (3)	152

Symmetry codes: (i) −x+1, −y−1, −z+1; (ii) x, y+1, z; (iii) −x+1, y+1/2, −z+1/2.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Pinto, A. C., Lapis, A. A. M., da Silva, B. V., Bastos, R. S., Dupont, J. & Neto, B. A. D. (2008). Tetrahedron Lett. 49, 5639–5641. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2328

doi:10.1107/S1600536809034321

Open

access