1-(2,6-Dichloro-phen-yl)indolin-2-one.

In the mol-ecule of the title compound, C(14)H(9)Cl(2)NO, the planar indole ring system [with a maximum deviation of 0.020 (2) Å for the N atom] is oriented at a dihedral angle of 72.17 (3)° with respect to the phenyl ring. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules. A weak C-H⋯π inter-action may further stabilize the structure.

Related literature

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

Experimental

Crystal data

C14H9Cl2NO

M = 278.12

Monoclinic,

a = 7.1412 (8) Å

b = 8.0241 (9) Å

c = 11.0510 (13) Å

β = 105.789 (2)°

V = 609.35 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.52 mm−1

T = 173 K

0.30 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.755, T max = 0.902

3710 measured reflections

2328 independent reflections

2295 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.060

S = 1.06

2328 reflections

163 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), 705 Friedel pairs

Flack parameter: −0.02 (4)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005807/hk2625sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005807/hk2625Isup2.hkl

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

C14H9Cl2NO	F(000) = 284
Mr = 278.12	Dx = 1.516 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2148 reflections
a = 7.1412 (8) Å	θ = 5.2–24.3°
b = 8.0241 (9) Å	µ = 0.52 mm−1
c = 11.0510 (13) Å	T = 173 K
β = 105.789 (2)°	Block, yellow
V = 609.35 (12) Å3	0.30 × 0.24 × 0.20 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2328 independent reflections
Radiation source: fine-focus sealed tube	2295 reflections with I > 2σ(I)
graphite	Rint = 0.014
ω and φ scans	θmax = 28.3°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.755, Tmax = 0.902	k = −9→10
3710 measured reflections	l = −14→11

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)] = 0.021	H-atom parameters constrained
wR(F2) = 0.060	w = 1/[σ2(Fo2) + (0.0379P)2 + 0.0681P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2328 reflections	Δρmax = 0.19 e Å−3
163 parameters	Δρmin = −0.16 e Å−3
1 restraint	Absolute structure: Flack (1983), 705 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (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
Cl1	0.57381 (5)	0.76042 (5)	0.02255 (3)	0.03458 (10)
Cl2	0.05095 (6)	0.97960 (6)	0.25885 (3)	0.03843 (11)
O1	0.41005 (16)	0.54202 (14)	0.22865 (9)	0.0304 (2)
N1	0.43177 (17)	0.82839 (15)	0.24614 (10)	0.0230 (2)
C1	0.2984 (2)	0.86900 (18)	0.12903 (12)	0.0224 (2)
C2	0.3471 (2)	0.83882 (17)	0.01693 (12)	0.0243 (3)
C3	0.2172 (2)	0.8739 (2)	−0.09901 (13)	0.0302 (3)
H3A	0.2512	0.8509	−0.1747	0.036*
C4	0.0386 (2)	0.9425 (2)	−0.10285 (13)	0.0330 (3)
H4A	−0.0507	0.9663	−0.1819	0.040*
C5	−0.0126 (2)	0.9774 (2)	0.00703 (14)	0.0304 (3)
H5A	−0.1350	1.0266	0.0036	0.036*
C6	0.1176 (2)	0.93932 (19)	0.12198 (12)	0.0266 (3)
C7	0.48390 (19)	0.66561 (18)	0.28346 (12)	0.0233 (3)
C8	0.6499 (2)	0.67599 (18)	0.40391 (12)	0.0249 (3)
H8A	0.6135	0.6223	0.4749	0.030*
H8B	0.7688	0.6219	0.3929	0.030*
C9	0.6805 (2)	0.85913 (18)	0.42570 (12)	0.0234 (3)
C10	0.54970 (19)	0.94523 (17)	0.32861 (11)	0.0219 (2)
C11	0.5448 (2)	1.11669 (19)	0.32044 (13)	0.0286 (3)
H11A	0.4558	1.1731	0.2533	0.034*
C12	0.6774 (2)	1.2032 (2)	0.41607 (14)	0.0335 (3)
H12A	0.6783	1.3216	0.4138	0.040*
C13	0.8073 (2)	1.1219 (2)	0.51397 (15)	0.0357 (3)
H13A	0.8950	1.1846	0.5778	0.043*
C14	0.8101 (2)	0.9477 (2)	0.51951 (13)	0.0310 (3)
H14A	0.8994	0.8912	0.5865	0.037*

	U11	U22	U33	U12	U13	U23
Cl1	0.03021 (17)	0.0422 (2)	0.03333 (16)	0.00882 (15)	0.01213 (12)	−0.00025 (14)
Cl2	0.04088 (19)	0.0480 (2)	0.03094 (16)	0.01679 (17)	0.01741 (14)	0.00795 (15)
O1	0.0330 (5)	0.0230 (5)	0.0309 (5)	−0.0025 (4)	0.0011 (4)	−0.0026 (4)
N1	0.0249 (5)	0.0208 (5)	0.0204 (5)	0.0012 (4)	0.0010 (4)	−0.0009 (4)
C1	0.0235 (6)	0.0220 (6)	0.0197 (5)	0.0010 (5)	0.0025 (5)	0.0010 (4)
C2	0.0245 (6)	0.0223 (6)	0.0256 (6)	0.0011 (5)	0.0063 (5)	−0.0021 (5)
C3	0.0358 (8)	0.0322 (8)	0.0206 (6)	0.0009 (6)	0.0043 (5)	−0.0003 (5)
C4	0.0320 (7)	0.0379 (8)	0.0240 (6)	0.0021 (6)	−0.0012 (5)	0.0041 (6)
C5	0.0242 (6)	0.0343 (8)	0.0303 (6)	0.0058 (6)	0.0035 (5)	0.0062 (6)
C6	0.0274 (7)	0.0276 (7)	0.0251 (6)	0.0031 (6)	0.0077 (5)	0.0034 (5)
C7	0.0216 (6)	0.0239 (6)	0.0229 (5)	0.0004 (5)	0.0037 (5)	0.0007 (4)
C8	0.0235 (6)	0.0236 (6)	0.0241 (6)	0.0037 (5)	0.0006 (5)	0.0007 (5)
C9	0.0224 (6)	0.0244 (7)	0.0226 (5)	0.0010 (5)	0.0049 (5)	−0.0020 (5)
C10	0.0236 (6)	0.0225 (6)	0.0194 (5)	−0.0006 (5)	0.0055 (4)	−0.0032 (4)
C11	0.0352 (8)	0.0236 (7)	0.0290 (6)	0.0008 (6)	0.0122 (6)	0.0003 (5)
C12	0.0397 (8)	0.0230 (7)	0.0414 (7)	−0.0057 (6)	0.0173 (7)	−0.0081 (6)
C13	0.0303 (8)	0.0373 (8)	0.0389 (8)	−0.0068 (7)	0.0085 (6)	−0.0162 (6)
C14	0.0259 (7)	0.0371 (8)	0.0272 (6)	−0.0002 (6)	0.0023 (5)	−0.0080 (5)

C1—C6	1.392 (2)	C8—C9	1.4955 (19)
C1—C2	1.3958 (18)	C8—H8A	0.9900
C1—N1	1.4203 (15)	C8—H8B	0.9900
C2—C3	1.3908 (19)	C9—C14	1.3834 (19)
C2—Cl1	1.7223 (14)	C9—C10	1.3984 (18)
C3—C4	1.379 (2)	C10—C11	1.379 (2)
C3—H3A	0.9500	C10—N1	1.4146 (16)
C4—C5	1.389 (2)	C11—C12	1.397 (2)
C4—H4A	0.9500	C11—H11A	0.9500
C5—C6	1.3890 (19)	C12—C13	1.382 (2)
C5—H5A	0.9500	C12—H12A	0.9500
C6—Cl2	1.7353 (14)	C13—C14	1.399 (2)
C7—O1	1.2061 (17)	C13—H13A	0.9500
C7—N1	1.3896 (18)	C14—H14A	0.9500
C7—C8	1.5250 (17)
C6—C1—C2	118.16 (12)	C9—C8—H8B	111.0
C6—C1—N1	121.73 (12)	C7—C8—H8B	111.0
C2—C1—N1	120.12 (12)	H8A—C8—H8B	109.0
C3—C2—C1	121.19 (13)	C14—C9—C10	119.49 (14)
C3—C2—Cl1	119.46 (11)	C14—C9—C8	131.59 (14)
C1—C2—Cl1	119.34 (10)	C10—C9—C8	108.91 (12)
C4—C3—C2	119.23 (13)	C11—C10—C9	122.89 (13)
C4—C3—H3A	120.4	C11—C10—N1	128.25 (13)
C2—C3—H3A	120.4	C9—C10—N1	108.86 (12)
C3—C4—C5	121.01 (13)	C10—C11—C12	116.53 (14)
C3—C4—H4A	119.5	C10—C11—H11A	121.7
C5—C4—H4A	119.5	C12—C11—H11A	121.7
C4—C5—C6	119.01 (14)	C13—C12—C11	121.99 (15)
C4—C5—H5A	120.5	C13—C12—H12A	119.0
C6—C5—H5A	120.5	C11—C12—H12A	119.0
C5—C6—C1	121.38 (12)	C12—C13—C14	120.31 (14)
C5—C6—Cl2	118.81 (11)	C12—C13—H13A	119.8
C1—C6—Cl2	119.81 (10)	C14—C13—H13A	119.8
O1—C7—N1	125.35 (11)	C9—C14—C13	118.77 (14)
O1—C7—C8	127.81 (13)	C9—C14—H14A	120.6
N1—C7—C8	106.83 (11)	C13—C14—H14A	120.6
C9—C8—C7	103.83 (11)	C7—N1—C10	111.54 (10)
C9—C8—H8A	111.0	C7—N1—C1	123.04 (11)
C7—C8—H8A	111.0	C10—N1—C1	124.68 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1i	0.95	2.55	3.2267 (19)	128
C8—H8A···Cg1ii	0.99	2.74	3.6125 (23)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O1i	0.95	2.55	3.2267 (19)	128
C8—H8A⋯Cg1ii	0.99	2.74	3.6125 (23)	147

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C9–C14 ring.