(E)-3-(2,6-Dichloro-benzyl-idene)indolin-2-one.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(15)H(9)Cl(2)NO. The dihedral angles between the oxindolyl and dichloro-phenyl rings are essentially identical for the two independent mol-ecules [63.4 (1) and 63.2 (1)°]. Dimers linked by amide-carbonyl N-H⋯O hydrogen bonds are formed from each symmetry-independent mol-ecule and the respective symmetry equivalent created by inversion.

Related literature

For the syntheses and structures of related compounds, see: Ankati et al. (2009 ▶); Zhang et al. (2008 ▶, 2009a ▶,b ▶,c ▶). For the pharmacological properties of 3-(substituted-benzyl­idene)-1,3-dihydro-indolin derivatives, see: Andreani et al. (2006 ▶); Balderamos et al. (2008 ▶); Johnson et al. (2005 ▶); Olgen et al. (2005 ▶, 2007 ▶); Sun et al. (2003 ▶)

Experimental

Crystal data

C15H9Cl2NO

M = 290.13

Triclinic,

a = 8.3908 (5) Å

b = 12.6079 (7) Å

c = 12.7635 (7) Å

α = 99.334 (1)°

β = 91.188 (1)°

γ = 96.338 (1)°

V = 1323.2 (1) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 296 K

0.35 × 0.17 × 0.08 mm

Data collection

Bruker APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.849, T max = 0.964

16946 measured reflections

6459 independent reflections

4669 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.134

S = 1.03

6459 reflections

343 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043487/im2152sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043487/im2152Isup2.hkl

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

C15H9Cl2NO	Z = 4
Mr = 290.13	F(000) = 592
Triclinic, P1	Dx = 1.456 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3908 (5) Å	Cell parameters from 6257 reflections
b = 12.6079 (7) Å	θ = 2.8–27.9°
c = 12.7635 (7) Å	µ = 0.48 mm−1
α = 99.334 (1)°	T = 296 K
β = 91.188 (1)°	Plates, orange
γ = 96.338 (1)°	0.35 × 0.17 × 0.08 mm
V = 1323.2 (1) Å3

Bruker APEX diffractometer	6459 independent reflections
Radiation source: fine-focus sealed tube	4669 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 83.33 pixels mm-1	θmax = 28.3°, θmin = 1.6°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −16→16
Tmin = 0.849, Tmax = 0.964	l = −16→16
16946 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0619P)2 + 0.2428P] where P = (Fo2 + 2Fc2)/3
6459 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.23 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
N1	0.8867 (2)	0.59180 (14)	0.44745 (13)	0.0561 (4)
H1	0.9144	0.5842	0.5108	0.067*
C2	0.9182 (3)	0.52439 (18)	0.35853 (16)	0.0548 (5)
O2	0.9914 (2)	0.44512 (13)	0.35421 (12)	0.0729 (5)
C3	0.8476 (2)	0.56692 (16)	0.26602 (15)	0.0480 (5)
C4	0.6896 (3)	0.73604 (17)	0.27271 (17)	0.0537 (5)
H4	0.6677	0.7285	0.2000	0.064*
C5	0.6374 (3)	0.82040 (18)	0.3414 (2)	0.0609 (6)
H5	0.5800	0.8698	0.3146	0.073*
C6	0.6698 (3)	0.83215 (18)	0.44947 (19)	0.0613 (6)
H6	0.6343	0.8898	0.4944	0.074*
C7	0.7538 (3)	0.76009 (18)	0.49217 (17)	0.0575 (5)
H7	0.7760	0.7684	0.5649	0.069*
C8	0.8033 (2)	0.67554 (16)	0.42338 (16)	0.0487 (5)
C9	0.7750 (2)	0.66252 (16)	0.31353 (15)	0.0461 (4)
C10	0.8627 (3)	0.51431 (17)	0.16770 (16)	0.0520 (5)
H10	0.9152	0.4526	0.1636	0.062*
C11	0.8090 (2)	0.53923 (16)	0.06520 (15)	0.0478 (5)
C12	0.8584 (2)	0.63401 (17)	0.02580 (16)	0.0511 (5)
Cl12	0.99044 (8)	0.73448 (5)	0.10073 (5)	0.07059 (19)
C13	0.8105 (3)	0.6502 (2)	−0.07446 (18)	0.0665 (6)
H13	0.8441	0.7148	−0.0979	0.080*
C14	0.7137 (3)	0.5705 (3)	−0.13847 (19)	0.0764 (8)
H14	0.6818	0.5810	−0.2059	0.092*
C15	0.6628 (3)	0.4751 (2)	−0.10437 (19)	0.0747 (7)
H15	0.5965	0.4211	−0.1482	0.090*
C16	0.7111 (3)	0.46028 (18)	−0.00474 (17)	0.0570 (5)
Cl16	0.64687 (9)	0.33919 (5)	0.03774 (6)	0.0858 (2)
N21	0.6215 (2)	0.38621 (13)	0.51019 (13)	0.0534 (4)
H21	0.6146	0.4447	0.5543	0.064*
C22	0.5593 (3)	0.36652 (16)	0.40938 (16)	0.0513 (5)
O22	0.4820 (2)	0.42554 (12)	0.36706 (12)	0.0687 (5)
C23	0.6022 (2)	0.25727 (15)	0.36049 (15)	0.0461 (4)
C24	0.7577 (3)	0.12452 (17)	0.44962 (18)	0.0558 (5)
H24	0.7547	0.0704	0.3904	0.067*
C25	0.8278 (3)	0.1109 (2)	0.5444 (2)	0.0666 (6)
H25	0.8720	0.0473	0.5491	0.080*
C26	0.8328 (3)	0.1911 (2)	0.6324 (2)	0.0684 (6)
H26	0.8808	0.1805	0.6957	0.082*
C27	0.7682 (3)	0.28678 (19)	0.62897 (17)	0.0602 (6)
H27	0.7717	0.3405	0.6885	0.072*
C28	0.6985 (2)	0.29923 (16)	0.53382 (16)	0.0491 (5)
C29	0.6920 (2)	0.21915 (15)	0.44319 (15)	0.0461 (4)
C30	0.5491 (2)	0.21366 (15)	0.26238 (15)	0.0481 (5)
H30	0.4870	0.2549	0.2276	0.058*
C31	0.5768 (2)	0.10769 (15)	0.20232 (14)	0.0461 (4)
C32	0.4491 (3)	0.02878 (16)	0.16894 (16)	0.0518 (5)
Cl32	0.25656 (7)	0.05641 (5)	0.20230 (6)	0.0764 (2)
C33	0.4683 (3)	−0.07053 (18)	0.10949 (18)	0.0655 (6)
H33	0.3801	−0.1218	0.0890	0.079*
C34	0.6194 (4)	−0.0920 (2)	0.08132 (18)	0.0710 (7)
H34	0.6337	−0.1587	0.0415	0.085*
C35	0.7498 (3)	−0.0170 (2)	0.11093 (19)	0.0692 (7)
H35	0.8519	−0.0322	0.0910	0.083*
C36	0.7281 (3)	0.08203 (18)	0.17090 (17)	0.0562 (5)
Cl36	0.89345 (8)	0.17731 (6)	0.20621 (6)	0.0860 (2)

	U11	U22	U33	U12	U13	U23
N1	0.0754 (12)	0.0573 (11)	0.0375 (9)	0.0106 (9)	−0.0024 (8)	0.0117 (8)
C2	0.0685 (14)	0.0529 (12)	0.0444 (11)	0.0080 (10)	−0.0019 (10)	0.0122 (9)
O2	0.1095 (14)	0.0638 (10)	0.0513 (9)	0.0352 (10)	−0.0080 (9)	0.0110 (7)
C3	0.0548 (11)	0.0485 (11)	0.0418 (10)	0.0073 (9)	−0.0001 (8)	0.0099 (8)
C4	0.0568 (12)	0.0541 (12)	0.0520 (12)	0.0080 (10)	0.0024 (9)	0.0128 (10)
C5	0.0615 (13)	0.0540 (13)	0.0704 (15)	0.0139 (10)	0.0091 (11)	0.0136 (11)
C6	0.0663 (14)	0.0517 (12)	0.0647 (15)	0.0066 (11)	0.0176 (11)	0.0042 (11)
C7	0.0677 (14)	0.0572 (13)	0.0451 (11)	0.0011 (11)	0.0086 (10)	0.0043 (10)
C8	0.0525 (11)	0.0490 (11)	0.0443 (11)	−0.0009 (9)	0.0015 (8)	0.0116 (9)
C9	0.0490 (11)	0.0462 (11)	0.0434 (10)	0.0035 (8)	0.0030 (8)	0.0095 (8)
C10	0.0614 (13)	0.0488 (11)	0.0481 (11)	0.0164 (10)	−0.0007 (9)	0.0084 (9)
C11	0.0518 (11)	0.0534 (12)	0.0386 (10)	0.0184 (9)	0.0017 (8)	0.0004 (8)
C12	0.0529 (12)	0.0584 (12)	0.0437 (11)	0.0180 (10)	0.0048 (9)	0.0053 (9)
Cl12	0.0724 (4)	0.0672 (4)	0.0680 (4)	−0.0048 (3)	0.0039 (3)	0.0073 (3)
C13	0.0767 (16)	0.0827 (17)	0.0482 (13)	0.0330 (14)	0.0112 (11)	0.0175 (12)
C14	0.0839 (18)	0.109 (2)	0.0389 (12)	0.0392 (17)	−0.0063 (11)	0.0035 (13)
C15	0.0667 (15)	0.097 (2)	0.0513 (14)	0.0177 (14)	−0.0086 (11)	−0.0180 (14)
C16	0.0572 (12)	0.0594 (13)	0.0507 (12)	0.0134 (10)	0.0053 (10)	−0.0062 (10)
Cl16	0.0954 (5)	0.0576 (4)	0.0953 (5)	−0.0016 (3)	0.0205 (4)	−0.0090 (3)
N21	0.0712 (11)	0.0381 (9)	0.0460 (10)	0.0049 (8)	−0.0040 (8)	−0.0062 (7)
C22	0.0656 (13)	0.0391 (10)	0.0470 (11)	0.0052 (9)	0.0022 (9)	0.0009 (8)
O22	0.1060 (13)	0.0475 (8)	0.0536 (9)	0.0290 (9)	−0.0097 (8)	−0.0010 (7)
C23	0.0558 (11)	0.0354 (9)	0.0457 (11)	0.0053 (8)	0.0030 (9)	0.0020 (8)
C24	0.0636 (13)	0.0454 (11)	0.0568 (13)	0.0091 (10)	−0.0043 (10)	0.0029 (9)
C25	0.0698 (15)	0.0580 (14)	0.0739 (16)	0.0116 (11)	−0.0136 (12)	0.0158 (12)
C26	0.0715 (15)	0.0714 (16)	0.0608 (14)	0.0008 (12)	−0.0205 (12)	0.0145 (12)
C27	0.0659 (14)	0.0593 (13)	0.0485 (12)	−0.0037 (11)	−0.0092 (10)	−0.0024 (10)
C28	0.0502 (11)	0.0421 (10)	0.0509 (11)	−0.0026 (8)	−0.0017 (9)	0.0019 (8)
C29	0.0488 (11)	0.0423 (10)	0.0454 (10)	0.0008 (8)	−0.0010 (8)	0.0046 (8)
C30	0.0578 (12)	0.0420 (10)	0.0450 (11)	0.0141 (9)	0.0004 (9)	0.0038 (8)
C31	0.0609 (12)	0.0435 (10)	0.0346 (9)	0.0146 (9)	−0.0012 (8)	0.0030 (8)
C32	0.0658 (13)	0.0482 (11)	0.0414 (10)	0.0149 (10)	−0.0065 (9)	0.0028 (9)
Cl32	0.0616 (4)	0.0763 (4)	0.0860 (5)	0.0078 (3)	−0.0018 (3)	−0.0020 (3)
C33	0.0947 (18)	0.0446 (12)	0.0544 (13)	0.0137 (12)	−0.0129 (12)	−0.0020 (10)
C34	0.115 (2)	0.0513 (13)	0.0489 (13)	0.0359 (15)	−0.0008 (13)	−0.0040 (10)
C35	0.0865 (18)	0.0728 (16)	0.0558 (13)	0.0412 (14)	0.0129 (12)	0.0105 (12)
C36	0.0642 (13)	0.0562 (12)	0.0503 (12)	0.0174 (10)	0.0042 (10)	0.0082 (10)
Cl36	0.0609 (4)	0.0907 (5)	0.1046 (6)	0.0068 (3)	0.0163 (4)	0.0106 (4)

N1—C2	1.353 (3)	N21—C22	1.353 (3)
N1—C8	1.399 (3)	N21—C28	1.403 (3)
N1—H1	0.8600	N21—H21	0.8600
C2—O2	1.224 (2)	C22—O22	1.220 (3)
C2—C3	1.510 (3)	C22—C23	1.502 (3)
C3—C10	1.336 (3)	C23—C30	1.330 (3)
C3—C9	1.460 (3)	C23—C29	1.457 (3)
C4—C5	1.381 (3)	C24—C25	1.378 (3)
C4—C9	1.390 (3)	C24—C29	1.382 (3)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.381 (3)	C25—C26	1.381 (3)
C5—H5	0.9300	C25—H25	0.9300
C6—C7	1.380 (3)	C26—C27	1.383 (3)
C6—H6	0.9300	C26—H26	0.9300
C7—C8	1.375 (3)	C27—C28	1.376 (3)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.397 (3)	C28—C29	1.402 (3)
C10—C11	1.468 (3)	C30—C31	1.473 (3)
C10—H10	0.9300	C30—H30	0.9300
C11—C12	1.395 (3)	C31—C32	1.389 (3)
C11—C16	1.401 (3)	C31—C36	1.395 (3)
C12—C13	1.386 (3)	C32—C33	1.382 (3)
C12—Cl12	1.732 (2)	C32—Cl32	1.737 (2)
C13—C14	1.365 (4)	C33—C34	1.369 (4)
C13—H13	0.9300	C33—H33	0.9300
C14—C15	1.372 (4)	C34—C35	1.369 (4)
C14—H14	0.9300	C34—H34	0.9300
C15—C16	1.374 (3)	C35—C36	1.387 (3)
C15—H15	0.9300	C35—H35	0.9300
C16—Cl16	1.736 (3)	C36—Cl36	1.733 (2)
C2—N1—C8	111.47 (17)	C22—N21—C28	111.48 (16)
C2—N1—H1	124.3	C22—N21—H21	124.3
C8—N1—H1	124.3	C28—N21—H21	124.3
O2—C2—N1	126.48 (19)	O22—C22—N21	126.61 (19)
O2—C2—C3	126.87 (19)	O22—C22—C23	126.87 (19)
N1—C2—C3	106.64 (18)	N21—C22—C23	106.52 (18)
C10—C3—C9	136.10 (19)	C30—C23—C29	133.96 (18)
C10—C3—C2	118.73 (18)	C30—C23—C22	120.05 (18)
C9—C3—C2	105.17 (17)	C29—C23—C22	105.84 (16)
C5—C4—C9	119.3 (2)	C25—C24—C29	119.5 (2)
C5—C4—H4	120.4	C25—C24—H24	120.2
C9—C4—H4	120.4	C29—C24—H24	120.2
C4—C5—C6	120.6 (2)	C24—C25—C26	120.4 (2)
C4—C5—H5	119.7	C24—C25—H25	119.8
C6—C5—H5	119.7	C26—C25—H25	119.8
C7—C6—C5	121.3 (2)	C25—C26—C27	121.7 (2)
C7—C6—H6	119.3	C25—C26—H26	119.2
C5—C6—H6	119.3	C27—C26—H26	119.2
C8—C7—C6	117.7 (2)	C28—C27—C26	117.3 (2)
C8—C7—H7	121.2	C28—C27—H27	121.4
C6—C7—H7	121.2	C26—C27—H27	121.4
C7—C8—C9	122.4 (2)	C27—C28—C29	122.23 (19)
C7—C8—N1	128.23 (19)	C27—C28—N21	128.52 (19)
C9—C8—N1	109.37 (17)	C29—C28—N21	109.23 (17)
C4—C9—C8	118.71 (19)	C24—C29—C28	118.90 (18)
C4—C9—C3	133.96 (19)	C24—C29—C23	134.09 (18)
C8—C9—C3	107.33 (17)	C28—C29—C23	106.90 (17)
C3—C10—C11	129.73 (19)	C23—C30—C31	127.71 (18)
C3—C10—H10	115.1	C23—C30—H30	116.1
C11—C10—H10	115.1	C31—C30—H30	116.1
C12—C11—C16	115.33 (19)	C32—C31—C36	116.07 (18)
C12—C11—C10	125.09 (19)	C32—C31—C30	120.65 (18)
C16—C11—C10	119.4 (2)	C36—C31—C30	123.21 (19)
C13—C12—C11	122.4 (2)	C33—C32—C31	122.9 (2)
C13—C12—Cl12	117.53 (19)	C33—C32—Cl32	118.52 (19)
C11—C12—Cl12	120.03 (16)	C31—C32—Cl32	118.61 (15)
C14—C13—C12	119.5 (2)	C34—C33—C32	118.8 (2)
C14—C13—H13	120.3	C34—C33—H33	120.6
C12—C13—H13	120.3	C32—C33—H33	120.6
C13—C14—C15	120.7 (2)	C33—C34—C35	121.0 (2)
C13—C14—H14	119.7	C33—C34—H34	119.5
C15—C14—H14	119.7	C35—C34—H34	119.5
C14—C15—C16	119.2 (2)	C34—C35—C36	119.3 (2)
C14—C15—H15	120.4	C34—C35—H35	120.3
C16—C15—H15	120.4	C36—C35—H35	120.3
C15—C16—C11	122.9 (2)	C35—C36—C31	122.0 (2)
C15—C16—Cl16	118.9 (2)	C35—C36—Cl36	118.96 (19)
C11—C16—Cl16	118.12 (17)	C31—C36—Cl36	119.08 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O22i	0.86	2.03	2.854 (2)	159
N1—H1···O2ii	0.86	1.99	2.837 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N21—H21⋯O22i	0.86	2.03	2.854 (2)	159
N1—H1⋯O2ii	0.86	1.99	2.837 (2)	171

Symmetry codes: (i) ; (ii) .