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

The title mol-ecule, C(9)H(6)ClNO(2), is essentially planar; the maximum deviation of the indoline ring system is 0.027 (3) Å and the substituents do not deviate by more than 0.075 (2) Å from this plane. Inter-molecular C-H⋯O hydrogen bonds consolidate the crystal structure.

Related literature

For the preparation of the title compound, see: Bouhfid et al. (2005 ▶). For a related crystal structure and background to isatin derivatives, see: Liu et al. (2011 ▶).

Experimental

Crystal data

C9H6ClNO2

M = 195.60

Monoclinic,

a = 7.4890 (15) Å

b = 14.825 (3) Å

c = 7.3140 (15) Å

β = 90.27 (3)°

V = 812.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.919, T max = 0.958

1607 measured reflections

1485 independent reflections

965 reflections with I > 2σ(I)

R int = 0.042

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.155

S = 1.00

1485 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.28 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/S1600536811054171/pv2493sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054171/pv2493Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054171/pv2493Isup3.cml

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

C9H6ClNO2	F(000) = 400
Mr = 195.60	Dx = 1.600 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.4890 (15) Å	θ = 9–12°
b = 14.825 (3) Å	µ = 0.43 mm−1
c = 7.3140 (15) Å	T = 293 K
β = 90.27 (3)°	Block, yellow
V = 812.0 (3) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	965 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
graphite	θmax = 25.5°, θmin = 2.7°
ω/2θ scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→17
Tmin = 0.919, Tmax = 0.958	l = 0→8
1607 measured reflections	3 standard reflections every 200 reflections
1485 independent reflections	intensity decay: 1%

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)] = 0.060	H-atom parameters constrained
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.075P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1485 reflections	Δρmax = 0.28 e Å−3
119 parameters	Δρmin = −0.28 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (4)

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	0.19910 (14)	0.55890 (7)	0.16100 (16)	0.0561 (4)
N	0.3254 (4)	0.88873 (19)	0.2061 (4)	0.0430 (8)
O1	0.6058 (4)	0.87503 (19)	0.3282 (5)	0.0676 (10)
C1	0.1324 (5)	0.6685 (2)	0.1324 (5)	0.0425 (9)
O2	0.5204 (4)	0.68317 (18)	0.3142 (4)	0.0606 (9)
C2	−0.0323 (5)	0.6886 (3)	0.0589 (5)	0.0490 (11)
H2A	−0.1085	0.6423	0.0230	0.059*
C3	−0.0848 (5)	0.7773 (3)	0.0381 (6)	0.0540 (12)
H3A	−0.1982	0.7897	−0.0078	0.065*
C4	0.0265 (5)	0.8479 (3)	0.0835 (6)	0.0484 (10)
H4A	−0.0097	0.9074	0.0677	0.058*
C5	0.1921 (5)	0.8279 (2)	0.1525 (5)	0.0375 (9)
C6	0.4690 (5)	0.8435 (3)	0.2721 (6)	0.0470 (10)
C7	0.4229 (5)	0.7422 (2)	0.2603 (5)	0.0412 (9)
C8	0.2447 (4)	0.7390 (2)	0.1784 (5)	0.0370 (9)
C9	0.3123 (5)	0.9847 (3)	0.1887 (7)	0.0587 (12)
H9A	0.4200	1.0121	0.2338	0.088*
H9B	0.2126	1.0060	0.2584	0.088*
H9C	0.2957	1.0003	0.0624	0.088*

	U11	U22	U33	U12	U13	U23
Cl	0.0597 (7)	0.0389 (6)	0.0696 (8)	−0.0050 (5)	−0.0120 (5)	−0.0014 (5)
N	0.0351 (18)	0.0338 (17)	0.060 (2)	0.0011 (14)	−0.0083 (15)	−0.0031 (16)
O1	0.0420 (17)	0.0512 (18)	0.109 (3)	−0.0072 (14)	−0.0290 (17)	−0.0120 (18)
C1	0.043 (2)	0.042 (2)	0.043 (2)	−0.0048 (17)	−0.0040 (18)	−0.0005 (18)
O2	0.0446 (17)	0.0455 (17)	0.092 (2)	0.0107 (13)	−0.0241 (16)	−0.0012 (16)
C2	0.036 (2)	0.063 (3)	0.048 (2)	−0.016 (2)	−0.0084 (19)	−0.003 (2)
C3	0.034 (2)	0.077 (3)	0.051 (2)	0.000 (2)	−0.0105 (19)	0.006 (2)
C4	0.036 (2)	0.056 (2)	0.052 (2)	0.0071 (19)	−0.0058 (18)	0.006 (2)
C5	0.033 (2)	0.039 (2)	0.041 (2)	0.0036 (16)	−0.0057 (16)	−0.0009 (17)
C6	0.033 (2)	0.043 (2)	0.065 (3)	0.0051 (18)	−0.0069 (19)	−0.005 (2)
C7	0.034 (2)	0.037 (2)	0.052 (2)	0.0065 (17)	−0.0039 (18)	−0.0021 (19)
C8	0.0305 (19)	0.035 (2)	0.045 (2)	0.0036 (15)	−0.0068 (17)	−0.0031 (17)
C9	0.057 (3)	0.035 (2)	0.083 (3)	0.002 (2)	−0.006 (2)	0.001 (2)

Cl—C1	1.712 (4)	C3—C4	1.378 (6)
N—C6	1.354 (5)	C3—H3A	0.9300
N—C5	1.400 (4)	C4—C5	1.369 (5)
N—C9	1.431 (5)	C4—H4A	0.9300
O1—C6	1.197 (4)	C5—C8	1.389 (5)
C1—C2	1.376 (5)	C6—C7	1.544 (5)
C1—C8	1.382 (5)	C7—C8	1.461 (5)
O2—C7	1.204 (4)	C9—H9A	0.9600
C2—C3	1.381 (6)	C9—H9B	0.9600
C2—H2A	0.9300	C9—H9C	0.9600
C6—N—C5	110.2 (3)	C8—C5—N	111.8 (3)
C6—N—C9	125.2 (3)	O1—C6—N	127.3 (4)
C5—N—C9	124.6 (3)	O1—C6—C7	126.1 (4)
C2—C1—C8	118.3 (4)	N—C6—C7	106.6 (3)
C2—C1—Cl	120.9 (3)	O2—C7—C8	131.4 (4)
C8—C1—Cl	120.7 (3)	O2—C7—C6	123.6 (3)
C1—C2—C3	120.2 (4)	C8—C7—C6	104.9 (3)
C1—C2—H2A	119.9	C1—C8—C5	120.8 (3)
C3—C2—H2A	119.9	C1—C8—C7	132.7 (3)
C4—C3—C2	121.7 (4)	C5—C8—C7	106.5 (3)
C4—C3—H3A	119.2	N—C9—H9A	109.5
C2—C3—H3A	119.2	N—C9—H9B	109.5
C5—C4—C3	118.0 (4)	H9A—C9—H9B	109.5
C5—C4—H4A	121.0	N—C9—H9C	109.5
C3—C4—H4A	121.0	H9A—C9—H9C	109.5
C4—C5—C8	120.8 (4)	H9B—C9—H9C	109.5
C4—C5—N	127.4 (4)
C8—C1—C2—C3	−2.2 (6)	N—C6—C7—O2	−177.4 (4)
Cl—C1—C2—C3	179.5 (3)	O1—C6—C7—C8	−178.4 (4)
C1—C2—C3—C4	2.3 (6)	N—C6—C7—C8	1.3 (4)
C2—C3—C4—C5	−0.7 (6)	C2—C1—C8—C5	0.6 (6)
C3—C4—C5—C8	−1.0 (6)	Cl—C1—C8—C5	178.9 (3)
C3—C4—C5—N	179.6 (4)	C2—C1—C8—C7	178.7 (4)
C6—N—C5—C4	178.3 (4)	Cl—C1—C8—C7	−3.0 (6)
C9—N—C5—C4	−3.1 (6)	C4—C5—C8—C1	1.0 (6)
C6—N—C5—C8	−1.1 (5)	N—C5—C8—C1	−179.5 (3)
C9—N—C5—C8	177.4 (4)	C4—C5—C8—C7	−177.5 (4)
C5—N—C6—O1	179.5 (4)	N—C5—C8—C7	1.9 (4)
C9—N—C6—O1	0.9 (7)	O2—C7—C8—C1	−1.7 (8)
C5—N—C6—C7	−0.2 (4)	C6—C7—C8—C1	179.8 (4)
C9—N—C6—C7	−178.7 (4)	O2—C7—C8—C5	176.6 (4)
O1—C6—C7—O2	3.0 (7)	C6—C7—C8—C5	−1.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1i	0.93	2.58	3.323 (5)	137
C3—H3A···O2i	0.93	2.50	3.424 (5)	170
C9—H9A···O1	0.96	2.56	2.915 (5)	102
C9—H9A···O2ii	0.96	2.60	3.198 (5)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1i	0.93	2.58	3.323 (5)	137
C3—H3A⋯O2i	0.93	2.50	3.424 (5)	170
C9—H9A⋯O2ii	0.96	2.60	3.198 (5)	121

Symmetry codes: (i) ; (ii) .