Methyl 2-(5-chloro-1-methyl-2-oxo-2,3-di-hydro-1H-indol-3-ylidene)acetate.

The title compound, C12H10ClNO3, the indoline ring system is essentially planar, with a maximum deviation of 0.009 Å for the N atom. The indoline ring and acetate group are essentially coplanar, with a maximum deviation of 0.086 Å for the O atom. The mean plane through the methoxy-carbonyl-methyl group forms a dihedral angle of 3.68 (5)° with the plane of the indoline ring system. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O hydrogen-bond inter-action. In the crystal, π-π stacking inter-actions [centroid-centroid distance = 3.7677 (8) Å] occur between benzene rings, forming a chain running along the c-axis direction.

Related literature

For the biological activity of indole derivatives, see: Chai et al. (2006 ▶); Nieto et al. (2005 ▶); Singh et al. (2000 ▶); Andreani et al. (2001 ▶); Quetin-Leclercq (1994 ▶); Mukhopadhyay et al. (1981 ▶); Taylor et al. (1999 ▶). For closely related structures, see: Hu et al. (2011 ▶); Han & Luo (2012 ▶); Deng (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C12H10ClNO3

M = 251.66

Monoclinic,

a = 8.4709 (7) Å

b = 17.1658 (13) Å

c = 7.9481 (6) Å

β = 107.228 (4)°

V = 1103.88 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.903, T max = 0.934

10447 measured reflections

2815 independent reflections

2410 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.138

S = 1.13

2815 reflections

157 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813011768/bx2438sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011768/bx2438Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011768/bx2438Isup3.cml

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

C12H10ClNO3	F(000) = 520
Mr = 251.66	Dx = 1.514 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2857 reflections
a = 8.4709 (7) Å	θ = 2.4–28.6°
b = 17.1658 (13) Å	µ = 0.34 mm−1
c = 7.9481 (6) Å	T = 293 K
β = 107.228 (4)°	Block, colourless
V = 1103.88 (15) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	2815 independent reflections
Radiation source: fine-focus sealed tube	2410 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scans	θmax = 28.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.903, Tmax = 0.934	k = −23→23
10447 measured reflections	l = −10→10

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
2815 reflections	Δρmax = 0.34 e Å−3
157 parameters	Δρmin = −0.21 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: 0.008 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.18640 (15)	0.52152 (8)	0.41988 (16)	0.0337 (3)
C2	0.22645 (18)	0.44379 (9)	0.44263 (18)	0.0400 (3)
H2	0.3224	0.4283	0.5281	0.048*
C3	0.12324 (18)	0.38846 (8)	0.33765 (19)	0.0396 (3)
H3	0.1487	0.3357	0.3514	0.047*
C4	−0.01720 (16)	0.41357 (7)	0.21330 (17)	0.0321 (3)
C5	−0.05973 (15)	0.49301 (7)	0.18943 (15)	0.0287 (3)
C6	0.04383 (15)	0.54819 (7)	0.29523 (15)	0.0317 (3)
H6	0.0187	0.6010	0.2831	0.038*
C7	−0.21570 (16)	0.49743 (7)	0.04971 (15)	0.0306 (3)
C8	−0.25984 (18)	0.41402 (7)	−0.00755 (18)	0.0344 (3)
C9	−0.1339 (2)	0.28462 (9)	0.0829 (2)	0.0509 (4)
H9A	−0.2332	0.2668	−0.0022	0.076*
H9B	−0.1267	0.2625	0.1960	0.076*
H9C	−0.0398	0.2687	0.0476	0.076*
C10	−0.31915 (15)	0.55312 (8)	−0.03603 (16)	0.0349 (3)
H10	−0.4126	0.5363	−0.1232	0.042*
C11	−0.30207 (15)	0.63753 (7)	−0.00835 (16)	0.0341 (3)
C12	−0.4227 (2)	0.75770 (8)	−0.1167 (2)	0.0499 (4)
H12A	−0.4311	0.7724	−0.0031	0.075*
H12B	−0.5155	0.7782	−0.2068	0.075*
H12C	−0.3222	0.7783	−0.1314	0.075*
N1	−0.13690 (14)	0.36835 (6)	0.09414 (14)	0.0370 (3)
O1	−0.38178 (14)	0.39168 (7)	−0.12194 (15)	0.0484 (3)
O2	−0.19597 (13)	0.67151 (6)	0.10265 (16)	0.0503 (3)
O3	−0.42172 (12)	0.67452 (6)	−0.12966 (13)	0.0426 (3)
Cl1	0.31706 (4)	0.58922 (2)	0.55565 (4)	0.04557 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0283 (6)	0.0363 (7)	0.0319 (6)	−0.0017 (5)	0.0015 (5)	0.0008 (4)
C2	0.0347 (7)	0.0386 (7)	0.0406 (6)	0.0058 (6)	0.0016 (5)	0.0059 (5)
C3	0.0409 (7)	0.0302 (6)	0.0437 (7)	0.0054 (5)	0.0065 (6)	0.0047 (5)
C4	0.0331 (7)	0.0284 (6)	0.0340 (6)	−0.0013 (4)	0.0084 (5)	−0.0007 (4)
C5	0.0277 (6)	0.0265 (6)	0.0306 (5)	0.0001 (4)	0.0065 (4)	−0.0003 (4)
C6	0.0285 (6)	0.0303 (6)	0.0324 (6)	−0.0003 (5)	0.0031 (4)	−0.0001 (4)
C7	0.0289 (6)	0.0299 (6)	0.0307 (6)	−0.0030 (4)	0.0052 (4)	−0.0027 (4)
C8	0.0372 (7)	0.0298 (6)	0.0346 (6)	−0.0055 (5)	0.0084 (5)	−0.0045 (4)
C9	0.0618 (10)	0.0273 (7)	0.0595 (9)	−0.0019 (6)	0.0116 (7)	−0.0034 (6)
C10	0.0298 (6)	0.0344 (7)	0.0346 (6)	−0.0026 (5)	0.0003 (5)	−0.0025 (5)
C11	0.0298 (6)	0.0345 (7)	0.0332 (6)	0.0040 (5)	0.0021 (4)	0.0012 (5)
C12	0.0546 (9)	0.0351 (8)	0.0501 (8)	0.0081 (6)	0.0003 (7)	0.0075 (6)
N1	0.0406 (6)	0.0272 (6)	0.0399 (6)	−0.0034 (4)	0.0068 (5)	−0.0045 (4)
O1	0.0443 (6)	0.0404 (5)	0.0503 (6)	−0.0094 (4)	−0.0018 (5)	−0.0099 (4)
O2	0.0423 (6)	0.0347 (5)	0.0547 (6)	0.0022 (4)	−0.0151 (4)	−0.0065 (4)
O3	0.0408 (6)	0.0336 (5)	0.0406 (5)	0.0029 (4)	−0.0074 (4)	0.0021 (4)
Cl1	0.0370 (2)	0.0450 (3)	0.0434 (2)	−0.00716 (13)	−0.00546 (16)	−0.00314 (13)

C1—C2	1.3753 (19)	C8—O1	1.2183 (18)
C1—C6	1.3932 (16)	C8—N1	1.3615 (18)
C1—Cl1	1.7415 (13)	C9—N1	1.4408 (18)
C2—C3	1.389 (2)	C9—H9A	0.9600
C2—H2	0.9300	C9—H9B	0.9600
C3—C4	1.3717 (18)	C9—H9C	0.9600
C3—H3	0.9300	C10—C11	1.4661 (19)
C4—N1	1.3995 (16)	C10—H10	0.9300
C4—C5	1.4089 (17)	C11—O2	1.2070 (16)
C5—C6	1.3917 (16)	C11—O3	1.3346 (15)
C5—C7	1.4545 (17)	C12—O3	1.4320 (16)
C6—H6	0.9300	C12—H12A	0.9600
C7—C10	1.3389 (19)	C12—H12B	0.9600
C7—C8	1.5153 (17)	C12—H12C	0.9600
C2—C1—C6	122.71 (12)	N1—C8—C7	106.77 (11)
C2—C1—Cl1	118.64 (10)	N1—C9—H9A	109.5
C6—C1—Cl1	118.64 (10)	N1—C9—H9B	109.5
C1—C2—C3	119.83 (13)	H9A—C9—H9B	109.5
C1—C2—H2	120.1	N1—C9—H9C	109.5
C3—C2—H2	120.1	H9A—C9—H9C	109.5
C4—C3—C2	118.36 (12)	H9B—C9—H9C	109.5
C4—C3—H3	120.8	C7—C10—C11	127.50 (11)
C2—C3—H3	120.8	C7—C10—H10	116.3
C3—C4—N1	127.82 (11)	C11—C10—H10	116.3
C3—C4—C5	122.27 (12)	O2—C11—O3	122.67 (12)
N1—C4—C5	109.92 (11)	O2—C11—C10	127.33 (11)
C6—C5—C4	119.15 (11)	O3—C11—C10	109.98 (11)
C6—C5—C7	133.90 (11)	O3—C12—H12A	109.5
C4—C5—C7	106.94 (11)	O3—C12—H12B	109.5
C5—C6—C1	117.68 (11)	H12A—C12—H12B	109.5
C5—C6—H6	121.2	O3—C12—H12C	109.5
C1—C6—H6	121.2	H12A—C12—H12C	109.5
C10—C7—C5	137.34 (12)	H12B—C12—H12C	109.5
C10—C7—C8	117.12 (12)	C8—N1—C4	110.84 (10)
C5—C7—C8	105.52 (11)	C8—N1—C9	124.20 (12)
O1—C8—N1	126.31 (12)	C4—N1—C9	124.94 (12)
O1—C8—C7	126.92 (13)	C11—O3—C12	116.21 (11)
C6—C1—C2—C3	0.6 (2)	C5—C7—C8—O1	179.90 (14)
Cl1—C1—C2—C3	179.16 (10)	C10—C7—C8—N1	178.76 (11)
C1—C2—C3—C4	−0.1 (2)	C5—C7—C8—N1	0.12 (13)
C2—C3—C4—N1	179.68 (12)	C5—C7—C10—C11	−0.4 (2)
C2—C3—C4—C5	−0.2 (2)	C8—C7—C10—C11	−178.48 (12)
C3—C4—C5—C6	0.01 (19)	C7—C10—C11—O2	−4.1 (2)
N1—C4—C5—C6	−179.87 (10)	C7—C10—C11—O3	174.29 (13)
C3—C4—C5—C7	−179.19 (12)	O1—C8—N1—C4	−179.33 (13)
N1—C4—C5—C7	0.93 (13)	C7—C8—N1—C4	0.45 (14)
C4—C5—C6—C1	0.42 (17)	O1—C8—N1—C9	−0.9 (2)
C7—C5—C6—C1	179.36 (11)	C7—C8—N1—C9	178.84 (12)
C2—C1—C6—C5	−0.71 (19)	C3—C4—N1—C8	179.24 (13)
Cl1—C1—C6—C5	−179.32 (9)	C5—C4—N1—C8	−0.88 (14)
C6—C5—C7—C10	2.1 (2)	C3—C4—N1—C9	0.9 (2)
C4—C5—C7—C10	−178.84 (15)	C5—C4—N1—C9	−179.26 (13)
C6—C5—C7—C8	−179.66 (13)	O2—C11—O3—C12	−2.8 (2)
C4—C5—C7—C8	−0.63 (12)	C10—C11—O3—C12	178.73 (12)
C10—C7—C8—O1	−1.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.93	2.30	3.0181 (17)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2	0.93	2.30	3.0181 (17)	134