6-Chloro-1-methyl-indoline-2,3-dione.

The title mol-ecule, C(9)H(6)ClNO(2), is essentially planar: the maximum deviation from the mean plane of the indoline ring is 0.020 (2) Å and the substituents do not deviate by more than 0.053 (2) Å from this plane. C-H⋯O hydrogen bonds help to consolidate the crystal structure.

Related literature

The title compound is a halogenated derivative of isatin. For the cytotoxic and anti­neoplastic activity of halogenated isatin deriv­atives, see: Vine et al. (2007 ▶); Matesic et al. (2008 ▶). For the preparation of the title compound, see: Bouhfid et al. (2005 ▶). For a related structure, see: Wu et al. (2011 ▶).

Experimental

Crystal data

C9H6ClNO2

M = 195.60

Monoclinic,

a = 13.077 (3) Å

b = 7.9390 (16) Å

c = 16.673 (3) Å

β = 101.95 (3)°

V = 1693.5 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.41 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.887, T max = 0.960

3124 measured reflections

1557 independent reflections

1250 reflections with I > 2σ(I)

R int = 0.031

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.118

S = 1.00

1557 reflections

119 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811051294/pv2487sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051294/pv2487Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051294/pv2487Isup3.cml

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

C9H6ClNO2	F(000) = 800
Mr = 195.60	Dx = 1.534 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 13.077 (3) Å	θ = 9–13°
b = 7.9390 (16) Å	µ = 0.41 mm−1
c = 16.673 (3) Å	T = 293 K
β = 101.95 (3)°	Block, yellow
V = 1693.5 (6) Å3	0.30 × 0.20 × 0.10 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	1250 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 25.4°, θmin = 2.5°
ω/2θ scans	h = 0→15
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
Tmin = 0.887, Tmax = 0.960	l = −20→20
3124 measured reflections	3 standard reflections every 200 reflections
1557 independent reflections	intensity decay: 1%

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.080P)2] where P = (Fo2 + 2Fc2)/3
1557 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.27 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
Cl	0.44670 (4)	0.16058 (8)	0.34958 (3)	0.0700 (3)
N	0.64277 (11)	0.39456 (19)	0.62790 (9)	0.0490 (4)
C1	0.62506 (13)	0.3717 (2)	0.54308 (11)	0.0427 (4)
O1	0.84333 (11)	0.63253 (19)	0.57603 (13)	0.0790 (5)
C2	0.54622 (13)	0.2784 (2)	0.49497 (11)	0.0441 (4)
H2A	0.4961	0.2225	0.5172	0.053*
O2	0.76431 (12)	0.5344 (2)	0.72436 (10)	0.0801 (5)
C3	0.54593 (14)	0.2728 (2)	0.41247 (12)	0.0492 (5)
C4	0.62028 (16)	0.3525 (2)	0.37645 (13)	0.0552 (5)
H4A	0.6180	0.3424	0.3205	0.066*
C5	0.69747 (15)	0.4469 (2)	0.42582 (13)	0.0554 (5)
H5A	0.7472	0.5033	0.4033	0.067*
C6	0.69983 (13)	0.4564 (2)	0.50844 (12)	0.0484 (5)
C7	0.76899 (14)	0.5415 (2)	0.57711 (15)	0.0579 (5)
C8	0.72891 (14)	0.4939 (2)	0.65333 (14)	0.0579 (5)
C9	0.58013 (17)	0.3220 (3)	0.68150 (14)	0.0608 (5)
H9A	0.6096	0.3521	0.7373	0.091*
H9B	0.5794	0.2016	0.6761	0.091*
H9C	0.5100	0.3643	0.6666	0.091*

	U11	U22	U33	U12	U13	U23
Cl	0.0696 (4)	0.0753 (4)	0.0577 (4)	−0.0114 (3)	−0.0042 (3)	−0.0050 (2)
N	0.0434 (9)	0.0508 (9)	0.0522 (9)	−0.0023 (7)	0.0088 (7)	−0.0046 (7)
C1	0.0372 (9)	0.0385 (8)	0.0526 (10)	0.0041 (7)	0.0095 (7)	0.0015 (7)
O1	0.0522 (9)	0.0643 (9)	0.1197 (15)	−0.0190 (8)	0.0158 (9)	−0.0066 (9)
C2	0.0394 (9)	0.0423 (9)	0.0509 (10)	−0.0021 (7)	0.0100 (7)	0.0035 (7)
O2	0.0701 (10)	0.0856 (11)	0.0755 (12)	−0.0061 (8)	−0.0060 (8)	−0.0214 (9)
C3	0.0455 (10)	0.0446 (10)	0.0544 (11)	0.0033 (8)	0.0031 (8)	0.0022 (8)
C4	0.0631 (12)	0.0558 (12)	0.0481 (11)	0.0060 (9)	0.0143 (9)	0.0089 (8)
C5	0.0535 (11)	0.0511 (11)	0.0673 (13)	0.0018 (9)	0.0253 (9)	0.0131 (9)
C6	0.0384 (9)	0.0385 (9)	0.0690 (13)	0.0007 (7)	0.0126 (8)	0.0029 (8)
C7	0.0377 (10)	0.0444 (10)	0.0900 (16)	−0.0023 (8)	0.0098 (9)	−0.0042 (9)
C8	0.0433 (10)	0.0534 (11)	0.0715 (14)	0.0020 (8)	−0.0009 (9)	−0.0132 (9)
C9	0.0596 (12)	0.0710 (14)	0.0530 (12)	0.0004 (10)	0.0141 (9)	0.0037 (10)

Cl—C3	1.7361 (19)	C3—C4	1.396 (3)
N—C8	1.369 (2)	C4—C5	1.383 (3)
N—C1	1.397 (2)	C4—H4A	0.9300
N—C9	1.451 (3)	C5—C6	1.373 (3)
C1—C2	1.383 (2)	C5—H5A	0.9300
C1—C6	1.406 (2)	C6—C7	1.468 (3)
O1—C7	1.215 (2)	C7—C8	1.519 (3)
C2—C3	1.376 (3)	C9—H9A	0.9600
C2—H2A	0.9300	C9—H9B	0.9600
O2—C8	1.222 (3)	C9—H9C	0.9600
C8—N—C1	109.98 (16)	C4—C5—H5A	120.4
C8—N—C9	124.86 (18)	C5—C6—C1	120.85 (18)
C1—N—C9	125.16 (15)	C5—C6—C7	133.59 (17)
C2—C1—N	127.17 (16)	C1—C6—C7	105.55 (17)
C2—C1—C6	121.09 (17)	O1—C7—C6	128.9 (2)
N—C1—C6	111.74 (16)	O1—C7—C8	125.2 (2)
C3—C2—C1	116.40 (16)	C6—C7—C8	105.93 (16)
C3—C2—H2A	121.8	O2—C8—N	125.0 (2)
C1—C2—H2A	121.8	O2—C8—C7	128.2 (2)
C2—C3—C4	123.89 (18)	N—C8—C7	106.77 (17)
C2—C3—Cl	117.88 (14)	N—C9—H9A	109.5
C4—C3—Cl	118.23 (15)	N—C9—H9B	109.5
C5—C4—C3	118.50 (19)	H9A—C9—H9B	109.5
C5—C4—H4A	120.8	N—C9—H9C	109.5
C3—C4—H4A	120.8	H9A—C9—H9C	109.5
C6—C5—C4	119.24 (17)	H9B—C9—H9C	109.5
C6—C5—H5A	120.4
C8—N—C1—C2	179.45 (16)	C2—C1—C6—C7	179.49 (15)
C9—N—C1—C2	0.2 (3)	N—C1—C6—C7	−0.97 (19)
C8—N—C1—C6	0.0 (2)	C5—C6—C7—O1	2.2 (4)
C9—N—C1—C6	−179.27 (17)	C1—C6—C7—O1	−178.19 (19)
N—C1—C2—C3	−179.06 (16)	C5—C6—C7—C8	−178.04 (19)
C6—C1—C2—C3	0.4 (2)	C1—C6—C7—C8	1.52 (19)
C1—C2—C3—C4	1.0 (3)	C1—N—C8—O2	−179.21 (19)
C1—C2—C3—Cl	−178.72 (13)	C9—N—C8—O2	0.0 (3)
C2—C3—C4—C5	−1.9 (3)	C1—N—C8—C7	1.0 (2)
Cl—C3—C4—C5	177.82 (14)	C9—N—C8—C7	−179.76 (16)
C3—C4—C5—C6	1.3 (3)	O1—C7—C8—O2	−1.6 (3)
C4—C5—C6—C1	0.0 (3)	C6—C7—C8—O2	178.7 (2)
C4—C5—C6—C7	179.48 (19)	O1—C7—C8—N	178.14 (18)
C2—C1—C6—C5	−0.9 (3)	C6—C7—C8—N	−1.6 (2)
N—C1—C6—C5	178.65 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1i	0.93	2.50	3.419 (2)	168
C9—H9A···O2	0.96	2.53	2.906 (3)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1i	0.93	2.50	3.419 (2)	168

Symmetry code: (i) .