Spiro­[1,3-dioxolane-2,3′-indolin]-2′-one

Meng, Y.; Miao, Y.

doi:10.1107/S1600536810016132

organic compounds

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Volume 66| Part 6| June 2010| Page o1305

https://doi.org/10.1107/S1600536810016132

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Spiro[1,3-dioxolane-2,3′-indolin]-2′-one

Yan Meng ^a ^* and Yanqing Miao ^b

^aSchool of Environmental Engineering, Chang'an University, South Second Cycle Road 368#, Xi'an 710054, Shannxi, People's Republic of China, and ^bDepartment of Pharmacy, Xi'an Medical University, Hanguang Round No. 137, Xi'an 710021, Xi'an, People's Republic of China
^*Correspondence e-mail: cg1014@126.com

(Received 28 March 2010; accepted 2 May 2010; online 12 May 2010)

The title compound, C₁₀H₉NO₃, was synthesized by the condensation reaction of isatin (systematic name 1H-indole-2,3-dione) with glycol in presence of p-toluenesulfonic 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 intermolecular 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_r = 191.18
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.137
S = 1.09
1534 reflections
131 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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) -x+1, -y, -z+1.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016132/lx2143Isup2.hkl

checkCIF report

Comment top

Isatin derivatives, has caught great attention of many researchers as a versatile lead molecule for designing of potential drugs for the variety of biological activities, such as anti-bacteria, anti-virus, anti-tumor and neuroprotection. Among these compounds, spiro-oxindol analogues have received considerable attention as potential anti-bacteria and neuroprotection agents(Demosthenes et al. 1998; Rajopadhye et al. 1988; Santos et al. 2008).

The X-ray structural analysis confirmed the assignment of its structure from spectroscopic data. The molecular structure is depicted in Fig. 1, and a diagram of interactions between the title compounds is depicted in Fig. 2. Geometric parameters of the title compound are in the usual ranges. The crystal packing (Fig. 2) is stabilized by intermolecular N—H···O hydrogen bonds between the indoline H atom and the oxygen of the C═O unit, with a N1—H1···O1ⁱ (Table 1).

Related literature top

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 et al. (1988).

Experimental top

Isatin (1 mmol) and glycol (1 mmol) was dissolved in cyclohexane (20 ml), and 0.01 mmol TsOH was added. The mixture was stirred under reflux. After completion of the reaction, it was evaporated to dryness, followed by chromatography to the pure title compound. ¹H-NMR (D₆-Acetone, 400 MHz) delta: 10.44 (1H, s), 7.33 (2H, m), 7.00 (1H, td, J = 7.2, 0.8 Hz), 6.82 (1H, d, J = 7.6 Hz), 4.33 (2H, m), 4.23 (2H, m); EI–MS, m/z (%): 233 (M⁺)

Structure description top

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 et al. (1988).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2002); data reduction: SAINT-Plus (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small cycles of arbitrary radius.
	Fig. 2. N–H···O interactions (dotted lines) in the crystal structure of the title compound.

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

Crystal data top

C₁₀H₉NO₃	F(000) = 400
M_r = 191.18	D_x = 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

Data collection top

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

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)] = 0.048	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(F_o²) + (0.0648P)² + 0.151P] where P = (F_o² + 2F_c²)/3
1534 reflections	(Δ/σ)_max < 0.001
131 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₀H₉NO₃	V = 877.1 (4) Å³
M_r = 191.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.484 (2) Å	µ = 0.11 mm⁻¹
b = 5.650 (1) Å	T = 273 K
c = 20.942 (5) Å	0.36 × 0.27 × 0.21 mm
β = 97.889 (8)°

Data collection top

Bruker SMART CCD diffractometer	1534 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1093 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.989	R_int = 0.070
4056 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.23 e Å⁻³
1534 reflections	Δρ_min = −0.20 e Å⁻³
131 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	0.6983 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₉NO₃
M_r	191.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	7.484 (2), 5.650 (1), 20.942 (5)
β (°)	97.889 (8)
V (Å³)	877.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.36 × 0.27 × 0.21

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.963, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	4056, 1534, 1093
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.137, 1.09
No. of reflections	1534
No. of parameters	131
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.20

Computer programs: SMART (Bruker, 2002), SAINT-Plus (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1.

References

Bruker (2002). SMART, SAINT-Plus and SADABS. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Demosthenes, F., William, J. R., David, S. C. & David, L. C. (1998). Tetrahedron Lett. 39, 2235–2238. Google Scholar
Rajopadhye, M. & Popp, F. D. (1988). J. Med. Chem. 31, 1001–1005. CrossRef CAS PubMed Web of Science Google Scholar
Santos, E. L., Gomes, W. A. Jr, Ribeiro, N. M. & Andrade, H. M. C. (2008). J. Mol. Catal. A, 295, 18–23. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1305

https://doi.org/10.1107/S1600536810016132

Open

access