2-Oxoindolin-3-yl acetate

Deng, Q.

doi:10.1107/S1600536811009093

organic compounds

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Volume 67| Part 4| April 2011| Page o897

doi:10.1107/S1600536811009093

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2-Oxoindolin-3-yl acetate

Qiang Deng ^a ^*

^aXi'an Shiyou University, College of Chemistry and Chemical Engineering, Second Dianzi Road No.18, Xi'an 710065, Xi'an, People's Republic of China
^*Correspondence e-mail: tougao88@163.com

(Received 10 February 2011; accepted 9 March 2011; online 15 March 2011)

In the title compound, C₁₀H₉NO₃, the mean plane through the acetate group forms a dihedral angle of 83.39 (5)° with the plane of the indole ring system. In the crystal, pairs of centrosymmetrically related molecules are linked into dimers by N—H⋯O hydrogen bonds. The dimers are further connected into layers parallel to the bc plane by C—H⋯O hydrogen bonds.

Related literature

For the synthesis and applications of indole-2,3-dione derivatives, see: Chen, He et al. (2009 ); Chen, Wang et al. (2009 ); Chen, Hao et al. (2010 ); Chen, Tang et al. (2010 ).

Experimental

Crystal data

C₁₀H₉NO₃
M_r = 191.18
Monoclinic, P 2₁ /c
a = 10.617 (2) Å
b = 12.256 (2) Å
c = 7.4453 (14) Å
β = 106.347 (2)°
V = 929.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.35 × 0.30 × 0.30 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.977, T_max = 0.989
4286 measured reflections
1648 independent reflections
1348 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.129
S = 1.01
1648 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.03	2.8819 (19)	169
C2—H2A⋯O1ⁱⁱ	0.98	2.44	3.394 (2)	164
C4—H4A⋯O3ⁱⁱⁱ	0.93	2.56	3.328 (3)	141
Symmetry codes: (i) -x+2, -y, -z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x, y, z+1.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009093/rz2559sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009093/rz2559Isup2.hkl

checkCIF report

Comment top

Indole-2,3-dione derivatives have driven much attention for their anti-bacterial, anti-virus and neuroprotective activities (Chen, He et al., 2009; Chen, Wang et al., 2009; Chen, Hao et al., 2010; Chen, Tang et al., 2010). The title compound, whose structure is reported herein, has been synthesized by reduction of isatin with sodium borohydride followed by acylation. The X-ray structural analysis of the title compound revealed the molecular structure as depicted in Fig. 1. Geometric parameters are in the usual ranges. In the molecule, the mean plane through the ester group (O2/O3/C9/C10) is almost perpendicular to the plane of the indole ring system, forming a dihedral angle of 83.39 (5)°. In the crystal structure, centrosymmetrically related molecules are linked into dimers by N—H···O hydrogen bonds (Fig. 2; Table 1). The dimers are further connected into a layers parallel to the bc plane by weak C—H···O hydrogen bonds.

Related literature top

For the synthesis and applications of indole-2,3-dione derivatives, see: Chen, He et al. (2009); Chen, Wang et al. (2009); Chen, Hao et al. (2010); Chen, Tang et al. (2010).

Experimental top

To a solution of isatin (1.0 mmol) in methanol (20 ml), sodium borohydride (1.0 mmol) in methanol (10 ml) was added dropwise until the disappearance of isatin, as evidenced by thin-layer chromatography, then diluted hydrochloric acid (0.1 M) was added dropwise to eliminate the excess sodium borohydride. The solvent was removed in vacuo, and the residue was dissolved in 10 ml pyridine. Acetic anhydride (1.0 mmol) was then added, and the mixture was refluxed for 1 h. On completion of the reaction, the solvent was removed in vacuo, and the residue was separated by column chromatography (silica gel; petroleum ether/ethyl acetate 5:1 v/v), 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 7 d, to give colourless single crystals suitable for X-ray analysis on slow evaporation of the solvent.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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).

Figures top

	Fig. 1. The molecular structure of the title compound, with 30% probability displacement ellipsoids.
	Fig. 2. A dimer of the title compound. Intermolecular hydrogen bonds are drawn as dashed lines. Displacement ellipsoids are drawn at he 30% probability level.

2-Oxoindolin-3-yl acetate top

Crystal data top

C₁₀H₉NO₃	F(000) = 400
M_r = 191.18	D_x = 1.360 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7180 reflections
a = 10.617 (2) Å	θ = 1.6–25.0°
b = 12.256 (2) Å	µ = 0.10 mm⁻¹
c = 7.4453 (14) Å	T = 296 K
β = 106.347 (2)°	Block, colourless
V = 929.6 (3) Å³	0.35 × 0.30 × 0.30 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	1648 independent reflections
Radiation source: fine-focus sealed tube	1348 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→10
T_min = 0.977, T_max = 0.989	k = −14→14
4286 measured reflections	l = −8→8

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.095P)²] where P = (F_o² + 2F_c²)/3
1648 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₀H₉NO₃	V = 929.6 (3) Å³
M_r = 191.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.617 (2) Å	µ = 0.10 mm⁻¹
b = 12.256 (2) Å	T = 296 K
c = 7.4453 (14) Å	0.35 × 0.30 × 0.30 mm
β = 106.347 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	1648 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1348 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.989	R_int = 0.018
4286 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.01	Δρ_max = 0.24 e Å⁻³
1648 reflections	Δρ_min = −0.17 e Å⁻³
127 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
O2	0.67729 (11)	0.18607 (9)	0.11848 (15)	0.0419 (3)
O1	0.91573 (12)	0.13689 (9)	−0.01094 (17)	0.0479 (4)
O3	0.63567 (12)	0.03276 (10)	−0.05054 (17)	0.0509 (4)
N1	0.92299 (13)	−0.00916 (10)	0.18474 (19)	0.0386 (4)
H1A	0.9772	−0.0495	0.1478	0.046*
C7	0.86451 (16)	−0.03943 (12)	0.3255 (2)	0.0351 (4)
C2	0.79735 (15)	0.13809 (12)	0.2308 (2)	0.0373 (4)
H2A	0.8479	0.1957	0.3107	0.045*
C8	0.78545 (16)	0.04492 (13)	0.3545 (2)	0.0370 (4)
C1	0.88381 (15)	0.09027 (13)	0.1153 (2)	0.0371 (4)
C6	0.87970 (17)	−0.13532 (13)	0.4245 (2)	0.0414 (4)
H6A	0.9337	−0.1909	0.4041	0.050*
C9	0.60217 (16)	0.12244 (13)	−0.0200 (2)	0.0402 (4)
C5	0.81038 (19)	−0.14553 (15)	0.5569 (2)	0.0522 (5)
H5A	0.8167	−0.2102	0.6244	0.063*
C3	0.72078 (19)	0.03455 (15)	0.4902 (3)	0.0494 (5)
H3A	0.6700	0.0916	0.5141	0.059*
C10	0.47947 (19)	0.17936 (17)	−0.1220 (3)	0.0600 (6)
H10A	0.4289	0.1330	−0.2199	0.090*
H10B	0.5009	0.2457	−0.1755	0.090*
H10C	0.4293	0.1962	−0.0366	0.090*
C4	0.7324 (2)	−0.06214 (17)	0.5909 (3)	0.0561 (5)
H4A	0.6877	−0.0708	0.6810	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0401 (7)	0.0339 (6)	0.0487 (7)	0.0061 (5)	0.0075 (5)	−0.0026 (5)
O1	0.0483 (8)	0.0417 (7)	0.0596 (8)	0.0022 (5)	0.0247 (6)	0.0110 (6)
O3	0.0482 (8)	0.0489 (8)	0.0540 (8)	−0.0011 (6)	0.0120 (6)	−0.0137 (6)
N1	0.0360 (7)	0.0337 (7)	0.0471 (8)	0.0039 (6)	0.0133 (6)	−0.0002 (6)
C7	0.0332 (8)	0.0352 (9)	0.0335 (8)	−0.0036 (6)	0.0035 (7)	−0.0055 (6)
C2	0.0359 (9)	0.0322 (8)	0.0412 (9)	−0.0002 (7)	0.0067 (7)	−0.0054 (6)
C8	0.0379 (9)	0.0347 (9)	0.0358 (8)	−0.0019 (6)	0.0061 (7)	−0.0067 (6)
C1	0.0315 (8)	0.0319 (8)	0.0456 (9)	−0.0015 (6)	0.0070 (7)	−0.0017 (7)
C6	0.0448 (10)	0.0341 (9)	0.0385 (9)	−0.0010 (7)	0.0005 (7)	−0.0008 (7)
C9	0.0389 (9)	0.0408 (10)	0.0428 (9)	−0.0021 (7)	0.0148 (8)	0.0005 (7)
C5	0.0627 (12)	0.0488 (11)	0.0376 (9)	−0.0080 (9)	0.0020 (9)	0.0066 (8)
C3	0.0559 (11)	0.0500 (11)	0.0449 (10)	0.0008 (8)	0.0181 (9)	−0.0090 (8)
C10	0.0486 (11)	0.0603 (12)	0.0637 (12)	0.0017 (9)	0.0037 (10)	0.0078 (10)
C4	0.0689 (14)	0.0615 (12)	0.0418 (10)	−0.0084 (10)	0.0221 (10)	−0.0012 (8)

Geometric parameters (Å, º) top

O2—C9	1.3582 (19)	C8—C3	1.378 (2)
O2—C2	1.4385 (18)	C6—C5	1.392 (3)
O1—C1	1.2263 (19)	C6—H6A	0.9300
O3—C9	1.1965 (19)	C9—C10	1.484 (2)
N1—C1	1.343 (2)	C5—C4	1.383 (3)
N1—C7	1.410 (2)	C5—H5A	0.9300
N1—H1A	0.8600	C3—C4	1.389 (3)
C7—C6	1.372 (2)	C3—H3A	0.9300
C7—C8	1.386 (2)	C10—H10A	0.9600
C2—C8	1.495 (2)	C10—H10B	0.9600
C2—C1	1.539 (2)	C10—H10C	0.9600
C2—H2A	0.9800	C4—H4A	0.9300

C9—O2—C2	116.20 (12)	C7—C6—H6A	121.6
C1—N1—C7	111.81 (13)	C5—C6—H6A	121.6
C1—N1—H1A	124.1	O3—C9—O2	121.95 (15)
C7—N1—H1A	124.1	O3—C9—C10	126.84 (16)
C6—C7—C8	122.64 (16)	O2—C9—C10	111.21 (15)
C6—C7—N1	127.95 (15)	C4—C5—C6	121.75 (17)
C8—C7—N1	109.41 (14)	C4—C5—H5A	119.1
O2—C2—C8	117.11 (13)	C6—C5—H5A	119.1
O2—C2—C1	113.65 (12)	C8—C3—C4	119.17 (17)
C8—C2—C1	102.74 (12)	C8—C3—H3A	120.4
O2—C2—H2A	107.6	C4—C3—H3A	120.4
C8—C2—H2A	107.6	C9—C10—H10A	109.5
C1—C2—H2A	107.6	C9—C10—H10B	109.5
C3—C8—C7	119.61 (15)	H10A—C10—H10B	109.5
C3—C8—C2	131.95 (15)	C9—C10—H10C	109.5
C7—C8—C2	108.27 (14)	H10A—C10—H10C	109.5
O1—C1—N1	126.53 (15)	H10B—C10—H10C	109.5
O1—C1—C2	125.98 (15)	C5—C4—C3	119.92 (18)
N1—C1—C2	107.41 (13)	C5—C4—H4A	120.0
C7—C6—C5	116.86 (16)	C3—C4—H4A	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.03	2.8819 (19)	169
C2—H2A···O1ⁱⁱ	0.98	2.44	3.394 (2)	164
C4—H4A···O3ⁱⁱⁱ	0.93	2.56	3.328 (3)	141

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

Experimental details

Crystal data
Chemical formula	C₁₀H₉NO₃
M_r	191.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.617 (2), 12.256 (2), 7.4453 (14)
β (°)	106.347 (2)
V (Å³)	929.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.30 × 0.30

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.977, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	4286, 1648, 1348
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.129, 1.01
No. of reflections	1648
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.17

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.03	2.8819 (19)	169
C2—H2A···O1ⁱⁱ	0.98	2.44	3.394 (2)	164
C4—H4A···O3ⁱⁱⁱ	0.93	2.56	3.328 (3)	141

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

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o897

doi:10.1107/S1600536811009093

Open

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