(E)-5-Chloro-3-(2,6-dichloro-benzyl-idene)-indolin-2-one.

There are two independent mol-ecules of the title compound, C(15)H(8)Cl(3)NO, in the asymmetric unit. Both form inversion dimers via pairs of hydrazide-carbonyl N-H⋯O hydrogen bonds.

Related literature

For background information on the pharmacological activities of 3-substituted indoline-2-ones, see: Andreani et al. (2006 ▶); Sun et al. (2003 ▶); Johnson et al. (2005 ▶). For related structures, see: Gayathri et al. (2008 ▶); Ali et al. (2008 ▶); De (2008 ▶).

Experimental

Crystal data

C15H8Cl3NO

M = 324.57

Triclinic,

a = 8.0809 (6) Å

b = 13.4944 (11) Å

c = 14.3698 (16) Å

α = 63.116 (1)°

β = 82.973 (2)°

γ = 80.162 (1)°

V = 1375.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.66 mm−1

T = 296 (2) K

0.39 × 0.28 × 0.21 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.785, T max = 0.874

16659 measured reflections

6438 independent reflections

5292 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.158

S = 1.08

6438 reflections

361 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.39 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, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031930/jh2068sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031930/jh2068Isup2.hkl

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

C15H8Cl3NO	Z = 4
Mr = 324.57	F(000) = 656
Triclinic, P1	Dx = 1.568 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0809 (6) Å	Cell parameters from 9259 reflections
b = 13.4944 (11) Å	θ = 2.6–28.2°
c = 14.3698 (16) Å	µ = 0.66 mm−1
α = 63.116 (1)°	T = 296 K
β = 82.973 (2)°	Rod, orange
γ = 80.162 (1)°	0.39 × 0.28 × 0.21 mm
V = 1375.3 (2) Å3

Bruker APEX CCD area-detector diffractometer	6438 independent reflections
Radiation source: fine-focus sealed tube	5292 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 83.33 pixels mm-1	θmax = 28.2°, θmin = 1.6°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→17
Tmin = 0.785, Tmax = 0.874	l = −18→18
16659 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0786P)2 + 0.7214P] where P = (Fo2 + 2Fc2)/3
6438 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Experimental. 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.

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	0.8654 (3)	0.07885 (18)	0.38440 (16)	0.0441 (5)
H1	0.8834	0.0942	0.4340	0.053*
C2	0.9186 (3)	−0.0212 (2)	0.38197 (19)	0.0419 (5)
O2	1.0019 (3)	−0.10122 (17)	0.44698 (16)	0.0564 (5)
C3	0.8546 (3)	−0.0123 (2)	0.28386 (18)	0.0366 (5)
C4	0.6911 (3)	0.1609 (2)	0.13832 (19)	0.0407 (5)
H4	0.6838	0.1275	0.0950	0.049*
C5	0.6255 (4)	0.2711 (2)	0.1105 (2)	0.0465 (6)
Cl5	0.53114 (14)	0.34756 (7)	−0.00817 (7)	0.0780 (3)
C6	0.6336 (4)	0.3220 (2)	0.1745 (2)	0.0532 (7)
H6	0.5871	0.3964	0.1540	0.064*
C7	0.7100 (4)	0.2633 (2)	0.2680 (2)	0.0497 (6)
H7	0.7157	0.2968	0.3114	0.060*
C8	0.7778 (3)	0.1536 (2)	0.29584 (19)	0.0399 (5)
C9	0.7679 (3)	0.10133 (19)	0.23239 (18)	0.0355 (5)
C10	0.8876 (3)	−0.0984 (2)	0.26019 (19)	0.0396 (5)
H10	0.9537	−0.1608	0.3067	0.047*
C11	0.8348 (3)	−0.10953 (18)	0.17102 (18)	0.0358 (5)
C12	0.6685 (3)	−0.1043 (2)	0.15124 (19)	0.0405 (5)
Cl12	0.50744 (9)	−0.07520 (7)	0.23006 (6)	0.0552 (2)
C13	0.6254 (4)	−0.1275 (3)	0.0740 (2)	0.0534 (7)
H13	0.5128	−0.1237	0.0632	0.064*
C14	0.7491 (4)	−0.1563 (3)	0.0131 (2)	0.0614 (8)
H14	0.7202	−0.1718	−0.0393	0.074*
C15	0.9149 (4)	−0.1623 (3)	0.0288 (2)	0.0559 (7)
H15	0.9991	−0.1817	−0.0124	0.067*
C16	0.9551 (3)	−0.1393 (2)	0.1065 (2)	0.0426 (5)
Cl16	1.16558 (10)	−0.14706 (9)	0.12559 (7)	0.0693 (3)
N21	0.3669 (3)	0.12638 (17)	0.40122 (17)	0.0442 (5)
H21	0.3913	0.0600	0.4054	0.053*
C22	0.4168 (4)	0.1590 (2)	0.4684 (2)	0.0441 (6)
O22	0.5053 (3)	0.10166 (16)	0.54222 (16)	0.0602 (6)
C23	0.3436 (3)	0.28014 (19)	0.43404 (19)	0.0411 (5)
C24	0.1590 (4)	0.4078 (2)	0.2758 (2)	0.0457 (6)
H24	0.1457	0.4719	0.2863	0.055*
C25	0.0844 (4)	0.4072 (2)	0.1947 (2)	0.0522 (7)
Cl25	−0.04299 (14)	0.52723 (8)	0.11626 (7)	0.0819 (3)
C26	0.1041 (4)	0.3135 (3)	0.1766 (2)	0.0560 (7)
H26	0.0546	0.3164	0.1201	0.067*
C27	0.1976 (4)	0.2155 (2)	0.2423 (2)	0.0517 (7)
H27	0.2107	0.1517	0.2313	0.062*
C28	0.2706 (3)	0.2145 (2)	0.32410 (19)	0.0412 (5)
C29	0.2540 (3)	0.3105 (2)	0.34098 (19)	0.0399 (5)
C30	0.3666 (3)	0.3334 (2)	0.48909 (19)	0.0433 (6)
H30	0.4207	0.2894	0.5511	0.052*
C31	0.3183 (3)	0.4519 (2)	0.46532 (19)	0.0414 (6)
C32	0.3765 (4)	0.5398 (2)	0.3753 (2)	0.0451 (6)
Cl32	0.50911 (12)	0.51303 (6)	0.28279 (6)	0.0612 (2)
C33	0.3398 (4)	0.6498 (2)	0.3583 (2)	0.0524 (7)
H33	0.3818	0.7061	0.2979	0.063*
C34	0.2410 (4)	0.6762 (2)	0.4306 (3)	0.0569 (8)
H34	0.2143	0.7507	0.4185	0.068*
C35	0.1809 (4)	0.5927 (2)	0.5213 (3)	0.0562 (7)
H35	0.1142	0.6102	0.5707	0.067*
C36	0.2217 (4)	0.4827 (2)	0.5371 (2)	0.0459 (6)
Cl36	0.14997 (12)	0.37906 (7)	0.65309 (6)	0.0650 (2)

	U11	U22	U33	U12	U13	U23
N1	0.0581 (13)	0.0448 (12)	0.0374 (11)	0.0013 (10)	−0.0110 (9)	−0.0257 (9)
C2	0.0491 (14)	0.0430 (13)	0.0377 (12)	0.0000 (11)	−0.0068 (10)	−0.0222 (11)
O2	0.0766 (14)	0.0497 (11)	0.0483 (11)	0.0148 (10)	−0.0283 (10)	−0.0281 (9)
C3	0.0419 (12)	0.0388 (12)	0.0302 (11)	−0.0033 (10)	−0.0057 (9)	−0.0157 (10)
C4	0.0504 (14)	0.0393 (13)	0.0345 (12)	−0.0049 (10)	−0.0047 (10)	−0.0177 (10)
C5	0.0551 (15)	0.0406 (13)	0.0372 (13)	−0.0008 (11)	−0.0103 (11)	−0.0113 (11)
Cl5	0.1182 (8)	0.0484 (4)	0.0584 (5)	0.0115 (4)	−0.0432 (5)	−0.0139 (4)
C6	0.0665 (18)	0.0371 (13)	0.0557 (16)	0.0052 (12)	−0.0096 (14)	−0.0228 (12)
C7	0.0644 (17)	0.0419 (14)	0.0500 (15)	0.0009 (12)	−0.0068 (13)	−0.0284 (12)
C8	0.0436 (13)	0.0435 (13)	0.0361 (12)	−0.0038 (10)	−0.0026 (10)	−0.0212 (11)
C9	0.0399 (12)	0.0341 (11)	0.0340 (11)	−0.0038 (9)	−0.0019 (9)	−0.0166 (9)
C10	0.0469 (13)	0.0360 (12)	0.0351 (12)	0.0021 (10)	−0.0104 (10)	−0.0156 (10)
C11	0.0456 (13)	0.0287 (11)	0.0329 (11)	−0.0020 (9)	−0.0061 (9)	−0.0133 (9)
C12	0.0447 (13)	0.0397 (12)	0.0381 (12)	−0.0058 (10)	−0.0012 (10)	−0.0182 (10)
Cl12	0.0485 (4)	0.0678 (5)	0.0578 (4)	−0.0124 (3)	0.0077 (3)	−0.0361 (4)
C13	0.0503 (15)	0.0683 (19)	0.0521 (16)	−0.0161 (14)	−0.0043 (13)	−0.0325 (15)
C14	0.071 (2)	0.082 (2)	0.0520 (17)	−0.0184 (17)	−0.0036 (14)	−0.0451 (17)
C15	0.0613 (18)	0.0677 (19)	0.0483 (15)	−0.0050 (14)	0.0028 (13)	−0.0364 (15)
C16	0.0408 (13)	0.0451 (14)	0.0415 (13)	−0.0020 (10)	−0.0053 (10)	−0.0193 (11)
Cl16	0.0433 (4)	0.1032 (7)	0.0631 (5)	0.0028 (4)	−0.0077 (3)	−0.0411 (5)
N21	0.0630 (14)	0.0297 (10)	0.0405 (11)	−0.0003 (9)	−0.0007 (10)	−0.0185 (9)
C22	0.0616 (16)	0.0313 (12)	0.0376 (13)	−0.0003 (11)	0.0006 (11)	−0.0164 (10)
O22	0.0968 (16)	0.0346 (9)	0.0476 (11)	0.0152 (10)	−0.0217 (11)	−0.0203 (9)
C23	0.0538 (14)	0.0291 (11)	0.0378 (12)	0.0022 (10)	−0.0015 (11)	−0.0153 (10)
C24	0.0586 (16)	0.0361 (13)	0.0421 (13)	0.0010 (11)	−0.0035 (12)	−0.0192 (11)
C25	0.0617 (17)	0.0485 (15)	0.0395 (14)	0.0050 (13)	−0.0093 (12)	−0.0160 (12)
Cl25	0.1096 (8)	0.0673 (5)	0.0607 (5)	0.0255 (5)	−0.0378 (5)	−0.0257 (4)
C26	0.0694 (19)	0.0619 (18)	0.0438 (15)	−0.0053 (15)	−0.0094 (13)	−0.0290 (14)
C27	0.0702 (19)	0.0472 (15)	0.0478 (15)	−0.0081 (13)	−0.0006 (13)	−0.0303 (13)
C28	0.0498 (14)	0.0355 (12)	0.0387 (12)	−0.0042 (10)	0.0040 (10)	−0.0185 (10)
C29	0.0515 (14)	0.0366 (12)	0.0337 (12)	−0.0051 (10)	−0.0003 (10)	−0.0178 (10)
C30	0.0601 (16)	0.0306 (12)	0.0365 (12)	0.0034 (10)	−0.0111 (11)	−0.0137 (10)
C31	0.0559 (15)	0.0325 (12)	0.0390 (12)	0.0039 (10)	−0.0152 (11)	−0.0187 (10)
C32	0.0595 (16)	0.0380 (13)	0.0397 (13)	0.0004 (11)	−0.0133 (11)	−0.0184 (11)
Cl32	0.0888 (6)	0.0524 (4)	0.0433 (4)	−0.0095 (4)	0.0018 (3)	−0.0231 (3)
C33	0.0693 (18)	0.0329 (13)	0.0535 (16)	−0.0012 (12)	−0.0223 (14)	−0.0148 (12)
C34	0.0660 (19)	0.0317 (13)	0.077 (2)	0.0092 (12)	−0.0240 (16)	−0.0275 (14)
C35	0.0593 (17)	0.0475 (15)	0.071 (2)	0.0038 (13)	−0.0068 (15)	−0.0374 (15)
C36	0.0572 (16)	0.0380 (13)	0.0453 (14)	−0.0020 (11)	−0.0082 (12)	−0.0210 (11)
Cl36	0.0868 (6)	0.0549 (4)	0.0561 (4)	−0.0154 (4)	0.0106 (4)	−0.0283 (4)

N1—C2	1.360 (3)	N21—C22	1.352 (3)
N1—C8	1.398 (3)	N21—C28	1.397 (3)
N1—H1	0.8600	N21—H21	0.8600
C2—O2	1.219 (3)	C22—O22	1.220 (3)
C2—C3	1.508 (3)	C22—C23	1.509 (3)
C3—C10	1.329 (3)	C23—C30	1.331 (3)
C3—C9	1.457 (3)	C23—C29	1.456 (4)
C4—C5	1.378 (4)	C24—C25	1.378 (4)
C4—C9	1.383 (3)	C24—C29	1.382 (4)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.387 (4)	C25—C26	1.383 (4)
C5—Cl5	1.736 (3)	C25—Cl25	1.737 (3)
C6—C7	1.373 (4)	C26—C27	1.385 (4)
C6—H6	0.9300	C26—H26	0.9300
C7—C8	1.375 (4)	C27—C28	1.372 (4)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.397 (3)	C28—C29	1.404 (3)
C10—C11	1.475 (3)	C30—C31	1.467 (3)
C10—H10	0.9300	C30—H30	0.9300
C11—C12	1.391 (4)	C31—C36	1.388 (4)
C11—C16	1.395 (3)	C31—C32	1.398 (4)
C12—C13	1.378 (4)	C32—C33	1.374 (4)
C12—Cl12	1.732 (3)	C32—Cl32	1.733 (3)
C13—C14	1.370 (4)	C33—C34	1.370 (4)
C13—H13	0.9300	C33—H33	0.9300
C14—C15	1.369 (5)	C34—C35	1.381 (5)
C14—H14	0.9300	C34—H34	0.9300
C15—C16	1.373 (4)	C35—C36	1.382 (4)
C15—H15	0.9300	C35—H35	0.9300
C16—Cl16	1.734 (3)	C36—Cl36	1.733 (3)
C2—N1—C8	111.2 (2)	C22—N21—C28	111.3 (2)
C2—N1—H1	124.4	C22—N21—H21	124.4
C8—N1—H1	124.4	C28—N21—H21	124.4
O2—C2—N1	125.9 (2)	O22—C22—N21	126.6 (2)
O2—C2—C3	127.6 (2)	O22—C22—C23	126.5 (2)
N1—C2—C3	106.4 (2)	N21—C22—C23	106.9 (2)
C10—C3—C9	134.2 (2)	C30—C23—C29	134.6 (2)
C10—C3—C2	120.2 (2)	C30—C23—C22	120.1 (2)
C9—C3—C2	105.53 (19)	C29—C23—C22	105.2 (2)
C5—C4—C9	118.1 (2)	C25—C24—C29	118.2 (2)
C5—C4—H4	120.9	C25—C24—H24	120.9
C9—C4—H4	120.9	C29—C24—H24	120.9
C4—C5—C6	121.8 (2)	C24—C25—C26	122.0 (3)
C4—C5—Cl5	118.7 (2)	C24—C25—Cl25	118.4 (2)
C6—C5—Cl5	119.6 (2)	C26—C25—Cl25	119.6 (2)
C7—C6—C5	120.3 (2)	C25—C26—C27	120.0 (3)
C7—C6—H6	119.8	C25—C26—H26	120.0
C5—C6—H6	119.8	C27—C26—H26	120.0
C6—C7—C8	118.4 (2)	C28—C27—C26	118.5 (2)
C6—C7—H7	120.8	C28—C27—H27	120.8
C8—C7—H7	120.8	C26—C27—H27	120.8
C7—C8—C9	121.6 (2)	C27—C28—N21	129.1 (2)
C7—C8—N1	128.7 (2)	C27—C28—C29	121.5 (2)
C9—C8—N1	109.7 (2)	N21—C28—C29	109.5 (2)
C4—C9—C8	119.8 (2)	C24—C29—C28	119.8 (2)
C4—C9—C3	133.0 (2)	C24—C29—C23	133.0 (2)
C8—C9—C3	107.1 (2)	C28—C29—C23	107.2 (2)
C3—C10—C11	129.5 (2)	C23—C30—C31	128.8 (2)
C3—C10—H10	115.3	C23—C30—H30	115.6
C11—C10—H10	115.3	C31—C30—H30	115.6
C12—C11—C16	115.2 (2)	C36—C31—C32	115.6 (2)
C12—C11—C10	124.4 (2)	C36—C31—C30	120.8 (2)
C16—C11—C10	120.0 (2)	C32—C31—C30	123.4 (2)
C13—C12—C11	122.5 (2)	C33—C32—C31	122.4 (3)
C13—C12—Cl12	117.7 (2)	C33—C32—Cl32	116.8 (2)
C11—C12—Cl12	119.70 (19)	C31—C32—Cl32	120.63 (19)
C14—C13—C12	119.7 (3)	C34—C33—C32	119.7 (3)
C14—C13—H13	120.1	C34—C33—H33	120.1
C12—C13—H13	120.1	C32—C33—H33	120.1
C15—C14—C13	120.3 (3)	C33—C34—C35	120.4 (2)
C15—C14—H14	119.9	C33—C34—H34	119.8
C13—C14—H14	119.9	C35—C34—H34	119.8
C14—C15—C16	119.0 (3)	C34—C35—C36	118.7 (3)
C14—C15—H15	120.5	C34—C35—H35	120.7
C16—C15—H15	120.5	C36—C35—H35	120.7
C15—C16—C11	123.3 (2)	C35—C36—C31	123.2 (3)
C15—C16—Cl16	118.6 (2)	C35—C36—Cl36	117.9 (2)
C11—C16—Cl16	118.14 (19)	C31—C36—Cl36	118.92 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.09	2.919 (3)	162
N21—H21···O22ii	0.86	2.02	2.838 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.09	2.919 (3)	162
N21—H21⋯O22ii	0.86	2.02	2.838 (3)	159

Symmetry codes: (i) ; (ii) .