Spiro-[1,3-dioxolane-2,3'-indolin]-2'-one.

The title compound, C(10)H(9)NO(3), was synthesized by the condensation reaction of isatin (systematic name 1H-indole-2,3-dione) with glycol in presence of p-toluene-sulfonic acid. The indol-2-one ring system is essentially planar [N-C-C-C torsion angle = 3.1 (2)°], and the 1,3-dioxolane ring is slightly distorted. The crystal structure exhibits inter-molecular N-H⋯O hydrogen bonds.

Related literature

For the synthesis of the title compound, see: Santos et al. (2008 ▶). For the bioactivity of the title compound, see: Demosthenes et al. (1998 ▶); Rajopadhye & Popp (1988 ▶).

Experimental

Crystal data

C10H9NO3

M = 191.18

Monoclinic,

a = 7.484 (2) Å

b = 5.650 (1) Å

c = 20.942 (5) Å

β = 97.889 (8)°

V = 877.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 273 K

0.36 × 0.27 × 0.21 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.963, T max = 0.989

4056 measured reflections

1534 independent reflections

1093 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.137

S = 1.09

1534 reflections

131 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810016132/lx2143sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016132/lx2143Isup2.hkl

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

C10H9NO3	F(000) = 400
Mr = 191.18	Dx = 1.448 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7304 reflections
a = 7.484 (2) Å	θ = 1.5–25.0°
b = 5.650 (1) Å	µ = 0.11 mm−1
c = 20.942 (5) Å	T = 273 K
β = 97.889 (8)°	Block, colourless
V = 877.1 (4) Å3	0.36 × 0.27 × 0.21 mm
Z = 4

Bruker SMART CCD diffractometer	1534 independent reflections
Radiation source: fine-focus sealed tube	1093 reflections with I > 2σ(I)
graphite	Rint = 0.070
phi and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→8
Tmin = 0.963, Tmax = 0.989	k = −6→6
4056 measured reflections	l = −21→24

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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0648P)2 + 0.151P] where P = (Fo2 + 2Fc2)/3
1534 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.6983 (2)	0.2241 (3)	0.50491 (8)	0.0600 (5)
O3	0.6788 (2)	0.6884 (3)	0.43906 (8)	0.0551 (5)
O2	0.8104 (2)	0.4151 (3)	0.38133 (8)	0.0560 (5)
N1	0.4575 (3)	0.1613 (4)	0.42609 (9)	0.0469 (6)
H1	0.407 (4)	0.044 (5)	0.4439 (13)	0.070 (9)*
C7	0.3813 (3)	0.2722 (4)	0.36864 (10)	0.0400 (6)
C2	0.6494 (3)	0.4723 (4)	0.40675 (10)	0.0417 (6)
C8	0.4869 (3)	0.4639 (4)	0.35588 (10)	0.0402 (6)
C3	0.4343 (3)	0.6053 (4)	0.30311 (11)	0.0506 (6)
H3A	0.5032	0.7355	0.2945	0.061*
C6	0.2254 (3)	0.2139 (4)	0.32859 (11)	0.0512 (6)
H6A	0.1566	0.0834	0.3370	0.061*
C1	0.6076 (3)	0.2731 (4)	0.45352 (10)	0.0447 (6)
C5	0.1752 (3)	0.3571 (5)	0.27544 (11)	0.0550 (7)
H5A	0.0707	0.3216	0.2477	0.066*
C4	0.2758 (3)	0.5498 (5)	0.26285 (11)	0.0542 (7)
H4A	0.2381	0.6443	0.2272	0.065*
C10	0.8530 (4)	0.7641 (6)	0.4348 (2)	0.0911 (11)
H10A	0.9164	0.7972	0.4774	0.109*
H10B	0.8504	0.9075	0.4092	0.109*
C9	0.9435 (4)	0.5760 (6)	0.40444 (16)	0.0809 (10)
H9B	1.0019	0.6383	0.3694	0.097*
H9C	1.0340	0.5011	0.4355	0.097*

	U11	U22	U33	U12	U13	U23
O1	0.0568 (12)	0.0592 (12)	0.0595 (10)	−0.0091 (9)	−0.0079 (9)	0.0079 (8)
O3	0.0577 (11)	0.0369 (9)	0.0735 (11)	−0.0087 (8)	0.0196 (9)	−0.0187 (8)
O2	0.0441 (10)	0.0489 (10)	0.0777 (11)	−0.0054 (8)	0.0176 (8)	−0.0210 (8)
N1	0.0488 (13)	0.0362 (11)	0.0535 (11)	−0.0084 (10)	−0.0008 (9)	0.0106 (9)
C7	0.0435 (14)	0.0317 (12)	0.0452 (12)	0.0029 (10)	0.0081 (10)	0.0008 (9)
C2	0.0424 (13)	0.0305 (12)	0.0538 (12)	−0.0037 (10)	0.0127 (10)	−0.0069 (10)
C8	0.0435 (13)	0.0297 (12)	0.0490 (12)	0.0015 (10)	0.0122 (10)	−0.0006 (9)
C3	0.0542 (15)	0.0397 (13)	0.0605 (14)	0.0000 (11)	0.0174 (12)	0.0095 (11)
C6	0.0495 (16)	0.0433 (14)	0.0596 (14)	−0.0058 (11)	0.0032 (11)	0.0019 (11)
C1	0.0464 (14)	0.0368 (13)	0.0497 (12)	0.0005 (11)	0.0022 (11)	−0.0019 (10)
C5	0.0483 (15)	0.0612 (17)	0.0540 (13)	0.0034 (13)	0.0014 (11)	0.0042 (12)
C4	0.0558 (16)	0.0569 (16)	0.0505 (13)	0.0139 (14)	0.0095 (11)	0.0114 (11)
C10	0.059 (2)	0.0579 (19)	0.160 (3)	−0.0178 (16)	0.028 (2)	−0.043 (2)
C9	0.0602 (18)	0.084 (2)	0.102 (2)	−0.0233 (17)	0.0217 (16)	−0.0377 (19)

O1—C1	1.223 (2)	C3—C4	1.393 (3)
O3—C10	1.387 (4)	C3—H3A	0.9300
O3—C2	1.399 (3)	C6—C5	1.386 (3)
O2—C9	1.386 (3)	C6—H6A	0.9300
O2—C2	1.420 (3)	C5—C4	1.370 (3)
N1—C1	1.347 (3)	C5—H5A	0.9300
N1—C7	1.406 (3)	C4—H4A	0.9300
N1—H1	0.87 (3)	C10—C9	1.452 (4)
C7—C6	1.380 (3)	C10—H10A	0.9700
C7—C8	1.388 (3)	C10—H10B	0.9700
C2—C8	1.503 (3)	C9—H9B	0.9700
C2—C1	1.552 (3)	C9—H9C	0.9700
C8—C3	1.377 (3)
C10—O3—C2	108.95 (19)	C5—C6—H6A	121.2
C9—O2—C2	109.03 (19)	O1—C1—N1	126.8 (2)
C1—N1—C7	111.8 (2)	O1—C1—C2	125.8 (2)
C1—N1—H1	124.0 (17)	N1—C1—C2	107.44 (18)
C7—N1—H1	123.8 (17)	C4—C5—C6	121.5 (2)
C6—C7—C8	121.7 (2)	C4—C5—H5A	119.2
C6—C7—N1	128.6 (2)	C6—C5—H5A	119.2
C8—C7—N1	109.75 (19)	C5—C4—C3	120.5 (2)
O3—C2—O2	107.13 (17)	C5—C4—H4A	119.8
O3—C2—C8	115.39 (18)	C3—C4—H4A	119.8
O2—C2—C8	111.88 (17)	O3—C10—C9	107.6 (2)
O3—C2—C1	111.09 (17)	O3—C10—H10A	110.2
O2—C2—C1	109.05 (18)	C9—C10—H10A	110.2
C8—C2—C1	102.17 (17)	O3—C10—H10B	110.2
C3—C8—C7	120.0 (2)	C9—C10—H10B	110.2
C3—C8—C2	131.7 (2)	H10A—C10—H10B	108.5
C7—C8—C2	108.34 (17)	O2—C9—C10	106.1 (2)
C8—C3—C4	118.7 (2)	O2—C9—H9B	110.5
C8—C3—H3A	120.6	C10—C9—H9B	110.5
C4—C3—H3A	120.6	O2—C9—H9C	110.5
C7—C6—C5	117.6 (2)	C10—C9—H9C	110.5
C7—C6—H6A	121.2	H9B—C9—H9C	108.7
C1—N1—C7—C6	−177.7 (2)	C7—C8—C3—C4	−0.9 (3)
C1—N1—C7—C8	1.5 (3)	C2—C8—C3—C4	178.4 (2)
C10—O3—C2—O2	−0.6 (3)	C8—C7—C6—C5	−1.3 (4)
C10—O3—C2—C8	−125.9 (3)	N1—C7—C6—C5	177.8 (2)
C10—O3—C2—C1	118.4 (3)	C7—N1—C1—O1	176.7 (2)
C9—O2—C2—O3	7.5 (3)	C7—N1—C1—C2	−5.3 (3)
C9—O2—C2—C8	134.9 (2)	O3—C2—C1—O1	−51.7 (3)
C9—O2—C2—C1	−112.8 (2)	O2—C2—C1—O1	66.2 (3)
C6—C7—C8—C3	1.8 (3)	C8—C2—C1—O1	−175.3 (2)
N1—C7—C8—C3	−177.5 (2)	O3—C2—C1—N1	130.3 (2)
C6—C7—C8—C2	−177.7 (2)	O2—C2—C1—N1	−111.9 (2)
N1—C7—C8—C2	3.1 (2)	C8—C2—C1—N1	6.7 (2)
O3—C2—C8—C3	54.2 (3)	C7—C6—C5—C4	−0.1 (4)
O2—C2—C8—C3	−68.6 (3)	C6—C5—C4—C3	0.9 (4)
C1—C2—C8—C3	174.9 (2)	C8—C3—C4—C5	−0.4 (4)
O3—C2—C8—C7	−126.4 (2)	C2—O3—C10—C9	−6.2 (4)
O2—C2—C8—C7	110.7 (2)	C2—O2—C9—C10	−11.1 (4)
C1—C2—C8—C7	−5.8 (2)	O3—C10—C9—O2	10.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.87 (3)	2.07 (3)	2.941 (3)	174 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.87 (3)	2.07 (3)	2.941 (3)	174 (2)

Symmetry code: (i) .