5'-Chloro-spiro-[1,3-dioxolane-2,3'-indolin]-2'-one: a potential anti-convulsant.

The title compound, C(10)H(8)ClNO(3), is a significant anti-convulsant agent. The indolinone system is essentially planar, the dihedral angle between the rings being 2.24 (8)°. The dioxolane ring adopts an envelope conformation; the dihedral angle between the plane through its four coplanar atoms and the indolinone system is 89.8 (1)°. The crystal structure is stabilized by a three-dimensional network of inter-molecular N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Codding et al. (1984 ▶); De (1990 ▶, 1992 ▶); De & Kitagawa (1991a ▶,b ▶); De & Kusunoki (1991 ▶); Dickerson & Geis (1969 ▶); Itai et al. (1978 ▶); James & Williams (1972 ▶); Popp (1977 ▶, 1984 ▶); Rajopadhye & Popp (1988 ▶); Chakraborty & Talapatra (1985 ▶); Chakraborty et al. (1985 ▶).

Experimental

Crystal data

C10H8ClNO3

M = 225.62

Monoclinic,

a = 18.266 (2) Å

b = 7.360 (1) Å

c = 14.821 (1) Å

β = 92.855 (7)°

V = 1990.0 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.37 mm−1

T = 298 (2) K

0.50 × 0.30 × 0.30 mm

Data collection

Rigaku AFC-4 diffractometer

Absorption correction: none

2479 measured reflections

2297 independent reflections

1591 reflections with I > 2σ(I)

R int = 0.042

3 standard reflections every 100 reflections intensity decay: 0.2%

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.189

S = 0.83

2297 reflections

160 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.52 e Å−3

Data collection: AFC-4 Diffractometer Control Software (Rigaku, 1997 ▶); cell refinement: AFC-4 Diffractometer Control Software; data reduction: AFC-4 Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP (Johnson, 1965 ▶); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800336X/er2049sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800336X/er2049Isup2.hkl

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

C10H8ClNO3	F000 = 928
Mr = 225.62	Dx = 1.506 Mg m−3Dm = 1.498 Mg m−3Dm measured by flotation
Monoclinic, I2/c	Melting point: 460 K
Hall symbol: -I 2yc	Mo Kα radiation λ = 0.71073 Å
a = 18.266 (2) Å	Cell parameters from 25 reflections
b = 7.360 (1) Å	θ = 2.2–27.5º
c = 14.821 (1) Å	µ = 0.37 mm−1
β = 92.855 (7)º	T = 298 (2) K
V = 1990.0 (4) Å3	Needle, colourless
Z = 8	0.50 × 0.30 × 0.30 mm

Rigaku AFC-4 diffractometer	Rint = 0.042
Radiation source: fine-focus sealed tube	θmax = 27.5º
Monochromator: graphite	θmin = 2.2º
T = 298(2) K	h = −23→23
ω scans	k = 0→9
Absorption correction: none	l = 0→19
2479 measured reflections	3 standard reflections
2297 independent reflections	every 100 reflections
1591 reflections with I > 2σ(I)	intensity decay: 0.2%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.189	w = 1/[σ2(Fo2) + (0.1365P)2 + 2.6179P] where P = (Fo2 + 2Fc2)/3
S = 0.83	(Δ/σ)max = 0.006
2297 reflections	Δρmax = 0.34 e Å−3
160 parameters	Δρmin = −0.52 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
Cl1	0.40898 (6)	−0.00775 (11)	0.43060 (5)	0.0825 (4)
O1	0.3184 (2)	0.5049 (4)	0.0001 (2)	0.0931 (9)
O2	0.37608 (10)	0.5934 (2)	0.18885 (12)	0.0534 (5)
O3	0.45532 (9)	0.4244 (2)	0.11210 (12)	0.0494 (4)
N1	0.28723 (12)	0.2542 (4)	0.0815 (2)	0.0612 (6)
C1	0.3263 (2)	0.4038 (4)	0.0651 (2)	0.0596 (7)
C2	0.38452 (12)	0.4261 (3)	0.1450 (2)	0.0442 (5)
C3	0.36853 (11)	0.2671 (3)	0.20354 (15)	0.0418 (5)
C4	0.40017 (12)	0.2147 (3)	0.2858 (2)	0.0446 (5)
C5	0.3712 (2)	0.0628 (3)	0.3264 (2)	0.0516 (6)
C6	0.3125 (2)	−0.0317 (4)	0.2873 (2)	0.0634 (8)
C7	0.2809 (2)	0.0217 (4)	0.2041 (2)	0.0606 (7)
C8	0.31030 (12)	0.1704 (3)	0.1639 (2)	0.0484 (5)
C9	0.4219 (2)	0.7216 (4)	0.1450 (2)	0.0678 (8)
C10	0.4787 (2)	0.6085 (4)	0.1035 (3)	0.0759 (9)
H4	0.4389 (16)	0.275 (4)	0.3142 (18)	0.051 (7)*
H6	0.2955 (19)	−0.126 (5)	0.316 (2)	0.069 (9)*
H7	0.234 (2)	−0.037 (5)	0.181 (2)	0.077 (10)*
H1	0.2565 (18)	0.206 (5)	0.047 (2)	0.062 (9)*
H91	0.393 (2)	0.792 (6)	0.102 (3)	0.110 (14)*
H92	0.441 (2)	0.808 (7)	0.189 (3)	0.086 (11)*
H101	0.5260	0.6263	0.1351	0.08*
H102	0.4822	0.6401	0.0403	0.08*

	U11	U22	U33	U12	U13	U23
Cl1	0.1293 (9)	0.0619 (5)	0.0567 (5)	0.0119 (4)	0.0092 (5)	0.0165 (3)
O1	0.099 (2)	0.100 (2)	0.077 (2)	0.0173 (14)	−0.0313 (13)	0.0273 (14)
O2	0.0595 (10)	0.0389 (9)	0.0630 (10)	0.0018 (7)	0.0167 (8)	−0.0016 (7)
O3	0.0459 (8)	0.0434 (9)	0.0594 (10)	0.0071 (7)	0.0089 (7)	0.0065 (7)
N1	0.0475 (11)	0.0723 (15)	0.0617 (13)	0.0053 (11)	−0.0181 (10)	−0.0182 (12)
C1	0.0552 (13)	0.065 (2)	0.0573 (14)	0.0149 (12)	−0.0140 (11)	0.0000 (12)
C2	0.0427 (10)	0.0426 (11)	0.0467 (11)	0.0043 (8)	−0.0024 (8)	0.0014 (9)
C3	0.0367 (9)	0.0384 (10)	0.0500 (11)	0.0013 (8)	−0.0004 (8)	−0.0026 (9)
C4	0.0426 (11)	0.0400 (11)	0.0509 (12)	−0.0019 (9)	−0.0016 (9)	−0.0015 (9)
C5	0.0677 (14)	0.0371 (11)	0.0514 (12)	0.0043 (10)	0.0157 (11)	0.0016 (9)
C6	0.077 (2)	0.0349 (11)	0.081 (2)	−0.0119 (12)	0.031 (2)	−0.0082 (12)
C7	0.0508 (13)	0.0505 (14)	0.081 (2)	−0.0119 (11)	0.0094 (12)	−0.0206 (13)
C8	0.0393 (10)	0.0447 (11)	0.0608 (13)	0.0020 (9)	0.0001 (9)	−0.0156 (10)
C9	0.083 (2)	0.0459 (14)	0.076 (2)	−0.0025 (13)	0.022 (2)	0.0066 (14)
C10	0.086 (2)	0.051 (2)	0.095 (2)	−0.0020 (15)	0.041 (2)	0.005 (2)

Cl1—C5	1.740 (3)	C4—C5	1.386 (3)
O1—C1	1.220 (4)	C4—H4	0.92 (3)
O2—C2	1.404 (3)	C5—C6	1.381 (4)
O2—C9	1.438 (3)	C6—C7	1.392 (5)
O3—C2	1.405 (3)	C6—H6	0.88 (4)
O3—C10	1.429 (4)	C7—C8	1.369 (4)
N1—C1	1.341 (4)	C7—H7	1.01 (4)
N1—C8	1.412 (4)	C9—C10	1.487 (4)
N1—H1	0.82 (3)	C9—H91	0.96 (4)
C1—C2	1.560 (3)	C9—H92	0.96 (4)
C2—C3	1.494 (3)	C10—H101	0.97
C3—C4	1.378 (3)	C10—H102	0.97
C3—C8	1.386 (3)
C2—O2—C9	106.6 (2)	C4—C5—Cl1	118.8 (2)
C2—O3—C10	107.9 (2)	C5—C6—C7	120.6 (2)
C1—N1—C8	112.1 (2)	C5—C6—H6	118.9 (23)
C1—N1—H1	126.8 (23)	C7—C6—H6	120.5 (23)
C8—N1—H1	120.7 (23)	C8—C7—C6	117.2 (2)
O1—C1—N1	127.0 (3)	C8—C7—H7	123.0 (21)
O1—C1—C2	125.8 (3)	C6—C7—H7	119.1 (21)
N1—C1—C2	107.3 (2)	C7—C8—C3	122.4 (2)
O3—C2—O2	107.0 (2)	C7—C8—N1	128.2 (2)
O3—C2—C3	113.9 (2)	C3—C8—N1	109.4 (2)
O2—C2—C3	112.9 (2)	O2—C9—C10	104.7 (2)
O3—C2—C1	109.8 (2)	O2—C9—H91	109.6 (26)
O2—C2—C1	110.9 (2)	C10—C9—H91	113.8 (26)
C3—C2—C1	102.3 (2)	O2—C9—H92	109.0 (23)
C4—C3—C8	120.7 (2)	C10—C9—H92	114.7 (24)
C4—C3—C2	130.3 (2)	H91—C9—H92	105.0 (36)
C8—C3—C2	108.9 (2)	O3—C10—C9	106.0 (2)
C3—C4—C5	117.2 (2)	O3—C10—H101	110.3
C3—C4—H4	123.2 (17)	C9—C10—H101	111.0
C5—C4—H4	119.6 (17)	O3—C10—H102	110.3
C6—C5—C4	122.0 (3)	C9—C10—H102	110.3
C6—C5—Cl1	119.2 (2)	H101—C10—H102	110.0
C9—O2—C2—O3	28.9 (2)	O2—C2—C3—C8	118.8 (2)
C9—O2—C2—C1	−90.9 (2)	O3—C2—C3—C4	63.6 (3)
C9—O2—C2—C3	155.0 (2)	O3—C2—C3—C8	−118.9 (2)
C2—O2—C9—C10	−23.5 (3)	C1—C2—C3—C4	−177.9 (2)
C10—O3—C2—O2	−22.6 (3)	C1—C2—C3—C8	−0.4 (2)
C10—O3—C2—C1	97.9 (2)	C2—C3—C4—C5	177.2 (2)
C10—O3—C2—C3	−148.1 (2)	C2—C3—C8—N1	0.9 (3)
C2—O3—C10—C9	7.5 (3)	C2—C3—C8—C7	−176.9 (2)
C8—N1—C1—O1	−179.1 (3)	C4—C3—C8—N1	178.7 (2)
C8—N1—C1—C2	0.8 (3)	C4—C3—C8—C7	0.9 (4)
C1—N1—C8—C3	−1.1 (3)	C3—C4—C5—Cl1	−179.6 (2)
C1—N1—C8—C7	176.6 (3)	C3—C4—C5—C6	−0.9 (4)
O1—C1—C2—O2	59.0 (4)	Cl1—C5—C6—C7	179.8 (2)
O1—C1—C2—O3	−59.1 (4)	C4—C5—C6—C7	1.0 (4)
O1—C1—C2—C3	179.7 (3)	C5—C6—C7—C8	−0.2 (4)
N1—C1—C2—O2	−120.9 (2)	C6—C7—C8—N1	−178.1 (3)
N1—C1—C2—O3	121.0 (2)	C6—C7—C8—C3	−0.7 (4)
N1—C1—C2—C3	−0.2 (3)	O2—C9—C10—O3	9.7 (3)
O2—C2—C3—C4	−58.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.82 (3)	2.11 (3)	2.885 (4)	157.4 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.82 (3)	2.11 (3)	2.885 (4)	157.4 (3)

Symmetry code: (i) .