2-Oxoindolin-3-yl acetate.

In the title compound, C(10)H(9)NO(3), 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 mol-ecules 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 = 191.18

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.129

S = 1.01

1648 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.17 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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H9NO3	F(000) = 400
Mr = 191.18	Dx = 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

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

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(Fo2) + (0.095P)2] where P = (Fo2 + 2Fc2)/3
1648 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) ; (ii) ; (iii) .