3,3-Dichloro-1-(chloro-meth-yl)indolin-2-one.

In the title compound, C(9)H(6)Cl(3)NO, the pyrrole ring is almost coplanar with the benzene ring [dihedral angle = 1.90 (9)°], while the Cl-C-N-C torsion angle is 98.78 (17)°. In the crystal, pairs of mol-ecules are inter-connected by pairs of Cl⋯Cl inter-actions [3.564 (5) Å], forming dimers, which are further peripherally connected through inter-molecular C-H⋯O=C and π-π inter-actions [centroid-centroid distances = 4.134 (7), 4.134 (6) and 4.238 (7) Å], forming a two-dimensional network.

Related literature

For the synthesis of the title compound, see: Höhme & Schwartz, (1974 ▶). For the synthesis of 1-(chloro­meth­yl) indoline-2,3-dione, see: Höhme & Schwartz, (1973 ▶). For Cl⋯Cl inter­actions, see: Reddy et al. (2006 ▶).

Experimental

Crystal data

C9H6Cl3NO

M = 250.50

Monoclinic,

a = 8.6102 (1) Å

b = 14.5573 (2) Å

c = 8.2461 (1) Å

β = 93.381 (1)°

V = 1031.78 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.85 mm−1

T = 296 K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

13146 measured reflections

2450 independent reflections

2156 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.094

S = 1.06

2450 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2 and SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810040717/kj2158sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040717/kj2158Isup2.hkl

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

C9H6Cl3NO	F(000) = 504
Mr = 250.50	Dx = 1.613 Mg m−3Dm = 1.613 Mg m−3Dm measured by not measured
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.6102 (1) Å	Cell parameters from 7007 reflections
b = 14.5573 (2) Å	θ = 2.5–27.8°
c = 8.2461 (1) Å	µ = 0.85 mm−1
β = 93.381 (1)°	T = 296 K
V = 1031.78 (2) Å3	Block, yellow
Z = 4	0.16 × 0.12 × 0.10 mm

Bruker APEXII CCD area-detector diffractometer	2156 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
graphite	θmax = 27.9°, θmin = 2.4°
phi and ω scans	h = −11→11
13146 measured reflections	k = −19→19
2450 independent reflections	l = −10→10

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0433P)2 + 0.4377P] where P = (Fo2 + 2Fc2)/3
2450 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.49 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
C9	0.4139 (2)	0.66723 (13)	0.5958 (2)	0.0448 (4)
H9A	0.3747	0.6171	0.5275	0.054*
H9B	0.4404	0.7176	0.5255	0.054*
Cl1	0.72991 (7)	0.48322 (4)	0.99637 (6)	0.06304 (17)
Cl3	0.87749 (7)	0.48989 (4)	0.69017 (7)	0.06607 (17)
Cl2	0.26419 (5)	0.70402 (4)	0.72483 (7)	0.06448 (17)
C1	0.9042 (2)	0.68812 (13)	0.9240 (2)	0.0478 (4)
H1	0.9838	0.6541	0.9762	0.057*
C2	0.9062 (2)	0.78348 (14)	0.9279 (3)	0.0533 (4)
H2	0.9882	0.8138	0.9836	0.064*
C3	0.7883 (2)	0.83366 (12)	0.8503 (2)	0.0497 (4)
H3	0.7922	0.8975	0.8545	0.060*
C4	0.66346 (19)	0.79124 (11)	0.7659 (2)	0.0415 (4)
H4	0.5837	0.8252	0.7139	0.050*
C5	0.66323 (17)	0.69655 (10)	0.76292 (19)	0.0345 (3)
C6	0.78112 (18)	0.64512 (11)	0.84075 (19)	0.0373 (3)
C7	0.74369 (19)	0.54609 (11)	0.8146 (2)	0.0410 (3)
C8	0.58313 (19)	0.54734 (11)	0.7189 (2)	0.0402 (3)
N1	0.54994 (15)	0.63781 (9)	0.68728 (17)	0.0385 (3)
O1	0.50408 (18)	0.48209 (9)	0.68047 (17)	0.0562 (3)

	U11	U22	U33	U12	U13	U23
C9	0.0434 (8)	0.0522 (9)	0.0379 (8)	0.0048 (7)	−0.0044 (7)	−0.0021 (7)
Cl1	0.0768 (3)	0.0574 (3)	0.0547 (3)	0.0061 (2)	0.0024 (2)	0.0214 (2)
Cl3	0.0658 (3)	0.0575 (3)	0.0769 (4)	0.0237 (2)	0.0207 (3)	−0.0084 (2)
Cl2	0.0411 (2)	0.0907 (4)	0.0615 (3)	0.0133 (2)	0.0021 (2)	−0.0031 (3)
C1	0.0344 (8)	0.0575 (10)	0.0512 (10)	0.0034 (7)	−0.0008 (7)	0.0031 (8)
C2	0.0421 (9)	0.0578 (11)	0.0595 (11)	−0.0122 (8)	−0.0006 (8)	−0.0053 (9)
C3	0.0509 (10)	0.0381 (8)	0.0609 (11)	−0.0072 (7)	0.0093 (8)	−0.0033 (8)
C4	0.0415 (8)	0.0350 (7)	0.0482 (9)	0.0034 (6)	0.0053 (7)	0.0020 (6)
C5	0.0332 (7)	0.0345 (7)	0.0361 (7)	0.0023 (5)	0.0045 (6)	−0.0008 (6)
C6	0.0358 (7)	0.0380 (8)	0.0386 (8)	0.0064 (6)	0.0062 (6)	0.0018 (6)
C7	0.0452 (8)	0.0369 (8)	0.0416 (8)	0.0106 (6)	0.0072 (7)	0.0039 (6)
C8	0.0473 (8)	0.0355 (7)	0.0383 (8)	0.0015 (6)	0.0075 (7)	−0.0014 (6)
N1	0.0379 (6)	0.0344 (6)	0.0428 (7)	0.0032 (5)	−0.0013 (5)	−0.0021 (5)
O1	0.0701 (9)	0.0399 (6)	0.0583 (8)	−0.0114 (6)	0.0012 (7)	−0.0040 (6)

C9—N1	1.422 (2)	C3—C4	1.390 (2)
C9—Cl2	1.8009 (18)	C3—H3	0.9300
C9—H9A	0.9700	C4—C5	1.379 (2)
C9—H9B	0.9700	C4—H4	0.9300
Cl1—C7	1.7664 (17)	C5—C6	1.388 (2)
Cl3—C7	1.7856 (16)	C5—N1	1.414 (2)
C1—C6	1.378 (2)	C6—C7	1.490 (2)
C1—C2	1.389 (3)	C7—C8	1.551 (2)
C1—H1	0.9300	C8—O1	1.200 (2)
C2—C3	1.378 (3)	C8—N1	1.369 (2)
C2—H2	0.9300
N1—C9—Cl2	111.84 (12)	C4—C5—C6	122.06 (15)
N1—C9—H9A	109.2	C4—C5—N1	127.79 (14)
Cl2—C9—H9A	109.2	C6—C5—N1	110.15 (13)
N1—C9—H9B	109.2	C1—C6—C5	120.33 (15)
Cl2—C9—H9B	109.2	C1—C6—C7	131.67 (15)
H9A—C9—H9B	107.9	C5—C6—C7	107.99 (14)
C6—C1—C2	118.30 (16)	C6—C7—C8	103.95 (12)
C6—C1—H1	120.9	C6—C7—Cl1	113.78 (12)
C2—C1—H1	120.9	C8—C7—Cl1	109.59 (12)
C3—C2—C1	120.73 (17)	C6—C7—Cl3	112.65 (12)
C3—C2—H2	119.6	C8—C7—Cl3	107.40 (11)
C1—C2—H2	119.6	Cl1—C7—Cl3	109.15 (8)
C2—C3—C4	121.61 (16)	O1—C8—N1	127.02 (16)
C2—C3—H3	119.2	O1—C8—C7	126.84 (15)
C4—C3—H3	119.2	N1—C8—C7	106.13 (13)
C5—C4—C3	116.96 (16)	C8—N1—C5	111.52 (13)
C5—C4—H4	121.5	C8—N1—C9	123.16 (14)
C3—C4—H4	121.5	C5—N1—C9	125.26 (13)
C6—C1—C2—C3	−0.1 (3)	C6—C7—C8—O1	−175.08 (17)
C1—C2—C3—C4	0.1 (3)	Cl1—C7—C8—O1	−53.1 (2)
C2—C3—C4—C5	−0.2 (3)	Cl3—C7—C8—O1	65.3 (2)
C3—C4—C5—C6	0.3 (2)	C6—C7—C8—N1	4.91 (17)
C3—C4—C5—N1	179.42 (16)	Cl1—C7—C8—N1	126.87 (12)
C2—C1—C6—C5	0.2 (3)	Cl3—C7—C8—N1	−114.67 (12)
C2—C1—C6—C7	−179.47 (18)	O1—C8—N1—C5	174.89 (17)
C4—C5—C6—C1	−0.3 (2)	C7—C8—N1—C5	−5.10 (18)
N1—C5—C6—C1	−179.56 (15)	O1—C8—N1—C9	−2.4 (3)
C4—C5—C6—C7	179.42 (15)	C7—C8—N1—C9	177.62 (14)
N1—C5—C6—C7	0.16 (18)	C4—C5—N1—C8	−175.89 (16)
C1—C6—C7—C8	176.63 (17)	C6—C5—N1—C8	3.31 (19)
C5—C6—C7—C8	−3.04 (17)	C4—C5—N1—C9	1.3 (3)
C1—C6—C7—Cl1	57.5 (2)	C6—C5—N1—C9	−179.48 (15)
C5—C6—C7—Cl1	−122.18 (13)	Cl2—C9—N1—C8	98.78 (17)
C1—C6—C7—Cl3	−67.4 (2)	Cl2—C9—N1—C5	−78.12 (19)
C5—C6—C7—Cl3	112.91 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1i	0.93	2.57	3.173 (2)	123
C9—H9A···O1	0.97	2.56	2.879 (2)	100
C9—H9A···O1ii	0.97	2.52	3.256 (2)	133

Cg(A)	Cg(B)	Cg(A)···Cg(B) (Å)	sym. code Cg(B)
Cg1	Cg1	4.134 (7)	x, -y +3/2, z-1/2
Cg1	Cg1	4.134 (6)	x, -y +3/2, z+1/2
Cg1	Cg2	4.238 (7)	x, -y +3/2, z-1/2

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.93	2.57	3.173 (2)	123

Symmetry code: (i) .