1-(3-Chloro-benz-yl)-5-iodo-indoline-2,3-dione.

In the title compound, C(15)H(9)ClINO(2), which possesses anticonvulsant activity, the iodo-indoline ring system is essentially planar (maximum deviation 1.245 Å) and is oriented with respect to the 3-chloro-benzyl ring at a dihedral angle of 76.59 (3)°. In the crystal, there is a π-π contact between iodo-indoline ring systems [centroid-centroid distance = 3.8188 (4) Å].

Related literature

For general background, see: Hibino & Choshi (2002 ▶); Somei & Yamada (2003 ▶); Popp (1977 ▶); Popp (1984 ▶). For related structures, see: Chakraborty & Talapatra (1985 ▶); Chakraborty et al. (1985 ▶); Codding et al. (1984 ▶); De (1992 ▶); De & Kitagawa (1991a ▶,b ▶); Itai et al. (1978 ▶). For bond-length data, see: Allen et al. (1987 ▶);

Experimental

Crystal data

C15H9ClINO2

M = 397.58

Monoclinic,

a = 8.1241 (6) Å

b = 11.7930 (8) Å

c = 14.7001 (2) Å

β = 90.751 (3)°

V = 1408.23 (14) Å3

Z = 4

Mo Kα radiation

μ = 2.46 mm−1

T = 150 (1) K

0.37 × 0.30 × 0.06 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer

Absorption correction: integration (Coppens, 1970 ▶) T min = 0.473, T max = 0.837

12236 measured reflections

3203 independent reflections

2570 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.104

S = 1.11

3203 reflections

181 parameters

H-atom parameters constrained

Δρmax = 1.43 e Å−3

Δρmin = −0.79 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: COLLECT and DENZO (Otwinowski & Minor, 1997 ▶); data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034727/hk2560sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034727/hk2560Isup2.hkl

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

C15H9ClINO2	F(000) = 768
Mr = 397.58	Dx = 1.875 Mg m−3
Monoclinic, P21/c	Melting point: 411(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.1241 (6) Å	Cell parameters from 12323 reflections
b = 11.7930 (8) Å	θ = 1–27.5°
c = 14.7001 (2) Å	µ = 2.46 mm−1
β = 90.751 (3)°	T = 150 K
V = 1408.23 (14) Å3	Plate, colorless
Z = 4	0.37 × 0.30 × 0.06 mm

Bruker–Nonius KappaCCD area-detector diffractometer	3203 independent reflections
Radiation source: fine-focus sealed tube	2570 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 2.2°
φ and ω scans	h = −10→9
Absorption correction: integration (Coppens, 1970)	k = −15→14
Tmin = 0.473, Tmax = 0.837	l = −17→19
12236 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0373P)2 + 3.1264P] where P = (Fo2 + 2Fc2)/3
3203 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 1.43 e Å−3
0 restraints	Δρmin = −0.79 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
I1	0.21126 (4)	−0.00688 (3)	−0.168370 (19)	0.04622 (13)
Cl1	0.0801 (2)	0.12211 (13)	0.61991 (8)	0.0713 (5)
N1	0.3994 (4)	0.1400 (3)	0.2264 (2)	0.0304 (7)
O1	0.5622 (4)	0.2894 (3)	0.2730 (2)	0.0454 (8)
O2	0.5749 (4)	0.3308 (3)	0.0755 (2)	0.0472 (8)
C1	0.4945 (5)	0.2340 (3)	0.2144 (3)	0.0331 (8)
C2	0.5037 (5)	0.2528 (3)	0.1103 (3)	0.0330 (8)
C3	0.4080 (5)	0.1602 (3)	0.0698 (3)	0.0286 (8)
C4	0.3728 (5)	0.1328 (3)	−0.0195 (3)	0.0305 (8)
H4	0.4138	0.1759	−0.0670	0.037*
C5	0.2736 (5)	0.0393 (3)	−0.0354 (3)	0.0311 (8)
C6	0.2127 (5)	−0.0241 (3)	0.0360 (3)	0.0360 (9)
H6	0.1452	−0.0860	0.0235	0.043*
C7	0.2493 (5)	0.0025 (3)	0.1261 (3)	0.0333 (8)
H7	0.2090	−0.0406	0.1739	0.040*
C8	0.3475 (4)	0.0955 (3)	0.1419 (2)	0.0261 (7)
C9	0.3778 (5)	0.0850 (4)	0.3135 (3)	0.0354 (9)
H9A	0.4725	0.1016	0.3521	0.043*
H9B	0.3743	0.0036	0.3042	0.043*
C10	0.2237 (5)	0.1204 (3)	0.3623 (3)	0.0339 (8)
C11	0.2173 (6)	0.1038 (4)	0.4557 (3)	0.0385 (9)
H11	0.3057	0.0708	0.4866	0.046*
C12	0.0790 (7)	0.1355 (4)	0.5020 (3)	0.0434 (11)
C13	−0.0563 (7)	0.1805 (4)	0.4584 (4)	0.0528 (13)
H13	−0.1491	0.2010	0.4910	0.063*
C14	−0.0506 (6)	0.1953 (4)	0.3650 (3)	0.0449 (11)
H14	−0.1422	0.2232	0.3337	0.054*
C15	0.0905 (5)	0.1688 (3)	0.3183 (3)	0.0363 (9)
H15	0.0956	0.1836	0.2563	0.044*

	U11	U22	U33	U12	U13	U23
I1	0.03707 (18)	0.0640 (2)	0.03741 (18)	0.01182 (13)	−0.00630 (12)	−0.01648 (13)
Cl1	0.1128 (13)	0.0684 (9)	0.0331 (6)	−0.0229 (8)	0.0206 (7)	−0.0073 (6)
N1	0.0271 (17)	0.0358 (17)	0.0284 (16)	−0.0010 (13)	0.0047 (12)	−0.0009 (13)
O1	0.0425 (18)	0.0493 (18)	0.0443 (17)	−0.0059 (14)	−0.0025 (14)	−0.0135 (14)
O2	0.0465 (19)	0.0435 (17)	0.0519 (19)	−0.0149 (14)	0.0100 (15)	0.0029 (14)
C1	0.029 (2)	0.035 (2)	0.0356 (19)	0.0031 (16)	0.0049 (15)	−0.0059 (16)
C2	0.027 (2)	0.0309 (19)	0.041 (2)	−0.0003 (15)	0.0081 (16)	−0.0015 (16)
C3	0.0227 (18)	0.0307 (18)	0.0325 (19)	0.0017 (14)	0.0062 (14)	0.0007 (15)
C4	0.027 (2)	0.0349 (19)	0.0302 (18)	0.0065 (15)	0.0041 (15)	−0.0003 (15)
C5	0.027 (2)	0.0361 (19)	0.0299 (18)	0.0080 (16)	0.0000 (15)	−0.0064 (16)
C6	0.030 (2)	0.033 (2)	0.045 (2)	−0.0015 (16)	−0.0017 (17)	−0.0033 (17)
C7	0.029 (2)	0.0333 (19)	0.038 (2)	−0.0004 (16)	0.0059 (16)	0.0052 (16)
C8	0.0222 (18)	0.0304 (17)	0.0260 (16)	0.0047 (14)	0.0038 (13)	0.0000 (14)
C9	0.034 (2)	0.045 (2)	0.0275 (18)	0.0062 (18)	0.0030 (16)	0.0041 (17)
C10	0.038 (2)	0.0315 (19)	0.0318 (19)	−0.0012 (16)	0.0048 (16)	0.0026 (15)
C11	0.048 (3)	0.037 (2)	0.031 (2)	−0.0049 (19)	0.0024 (18)	−0.0002 (17)
C12	0.065 (3)	0.037 (2)	0.029 (2)	−0.013 (2)	0.0120 (19)	−0.0039 (17)
C13	0.054 (3)	0.042 (2)	0.063 (3)	−0.009 (2)	0.026 (2)	−0.013 (2)
C14	0.038 (2)	0.046 (2)	0.051 (3)	0.0084 (19)	0.009 (2)	0.002 (2)
C15	0.038 (2)	0.040 (2)	0.0306 (19)	0.0019 (18)	0.0019 (16)	0.0027 (17)

I1—C5	2.086 (4)	C7—C8	1.374 (5)
Cl1—C12	1.740 (4)	C7—H7	0.9301
N1—C1	1.364 (5)	C9—C10	1.510 (6)
N1—C8	1.407 (5)	C9—H9A	0.9700
N1—C9	1.448 (5)	C9—H9B	0.9701
O1—C1	1.208 (5)	C11—C10	1.388 (6)
O2—C2	1.204 (5)	C11—H11	0.9300
C1—C2	1.550 (6)	C12—C13	1.372 (8)
C2—C3	1.463 (5)	C12—C11	1.373 (7)
C3—C8	1.401 (5)	C13—C14	1.386 (7)
C4—C3	1.378 (5)	C13—H13	0.9299
C4—H4	0.9299	C14—H14	0.9300
C5—C4	1.384 (6)	C15—C10	1.377 (6)
C5—C6	1.384 (6)	C15—C14	1.379 (6)
C6—H6	0.9300	C15—H15	0.9299
C7—C6	1.390 (6)
C1—N1—C8	110.7 (3)	C3—C8—N1	111.1 (3)
C1—N1—C9	123.6 (3)	N1—C9—C10	114.0 (3)
C8—N1—C9	125.1 (3)	N1—C9—H9A	108.8
O1—C1—N1	126.9 (4)	C10—C9—H9A	108.8
O1—C1—C2	126.8 (4)	N1—C9—H9B	108.8
N1—C1—C2	106.2 (3)	C10—C9—H9B	108.5
O2—C2—C3	130.8 (4)	H9A—C9—H9B	107.6
O2—C2—C1	124.0 (4)	C15—C10—C11	118.9 (4)
C3—C2—C1	105.2 (3)	C15—C10—C9	122.9 (4)
C4—C3—C8	121.5 (4)	C11—C10—C9	118.2 (4)
C4—C3—C2	131.7 (4)	C12—C11—C10	119.5 (4)
C8—C3—C2	106.8 (3)	C12—C11—H11	120.2
C3—C4—C5	117.4 (4)	C10—C11—H11	120.3
C3—C4—H4	121.1	C13—C12—C11	122.0 (4)
C5—C4—H4	121.5	C13—C12—Cl1	119.6 (4)
C4—C5—C6	121.0 (4)	C11—C12—Cl1	118.4 (4)
C4—C5—I1	120.0 (3)	C12—C13—C14	118.3 (4)
C6—C5—I1	119.0 (3)	C12—C13—H13	120.7
C5—C6—C7	121.7 (4)	C14—C13—H13	121.0
C5—C6—H6	119.3	C15—C14—C13	120.2 (5)
C7—C6—H6	119.0	C15—C14—H14	119.9
C8—C7—C6	117.3 (4)	C13—C14—H14	119.9
C8—C7—H7	121.2	C10—C15—C14	120.9 (4)
C6—C7—H7	121.5	C10—C15—H15	119.5
C7—C8—C3	121.0 (3)	C14—C15—H15	119.6
C7—C8—N1	127.9 (3)