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

The title compound, C(15)H(8)BrCl(2)NO, crystallizes with two independent mol-ecules in the asymmetric unit. The dihedral angles between the two aromatic rings are 62.74 (9) and 63.50 (6)° in the two independent molecules. In the crystal, the mol-ecules are connected by N-H⋯O hydrogen bonds, forming two centrosymmetric dimers.

Related literature

For the pharmacological properties of 3-substituted indoline-2-ones, see: Andreani et al. (2006 ▶); Johnson et al. (2005 ▶); Sun et al. (2003 ▶). a series of 3-substituted indoline-2-one derivatives have been synthesized in our laboratory and their neuroprotective activities have been tested, see: Ankati et al., (2009 ▶); Balderamos et al. (2008 ▶). For the structures of some of the derivatives, see: Zhang et al. (2008 ▶, 2009a ▶,b ▶).

Experimental

Crystal data

C15H8BrCl2NO

M = 369.03

Triclinic,

a = 8.1018 (4) Å

b = 13.5726 (7) Å

c = 14.4904 (7) Å

α = 63.575 (1)°

β = 82.956 (1)°

γ = 80.139 (1)°

V = 1403.89 (12) Å3

Z = 4

Mo Kα radiation

μ = 3.30 mm−1

T = 296 K

0.32 × 0.21 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.416, T max = 0.636

17925 measured reflections

6832 independent reflections

5263 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.100

S = 1.05

6832 reflections

361 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.76 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/S160053680903270X/bt5036sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903270X/bt5036Isup2.hkl

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

C15H8BrCl2NO	Z = 4
Mr = 369.03	F(000) = 728
Triclinic, P1	Dx = 1.746 Mg m−3
a = 8.1018 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.5726 (7) Å	Cell parameters from 8432 reflections
c = 14.4904 (7) Å	θ = 2.6–28.2°
α = 63.575 (1)°	µ = 3.30 mm−1
β = 82.956 (1)°	T = 296 K
γ = 80.139 (1)°	Rods, yellow
V = 1403.89 (12) Å3	0.32 × 0.21 × 0.15 mm

Bruker SMART APEX diffractometer	6832 independent reflections
Radiation source: fine-focus sealed tube	5263 reflections with I > 2σ(I)
graphite	Rint = 0.017
Detector resolution: 83.33 pixels mm-1	θmax = 28.3°, θmin = 1.7°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→17
Tmin = 0.416, Tmax = 0.636	l = −19→19
17925 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0447P)2 + 0.697P] where P = (Fo2 + 2Fc2)/3
6832 reflections	(Δ/σ)max = 0.001
361 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −0.76 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	0.6336 (3)	0.42436 (16)	0.61350 (15)	0.0430 (5)
H1	0.6158	0.4089	0.5644	0.052*
C2	0.5806 (3)	0.5237 (2)	0.61601 (18)	0.0405 (5)
O2	0.4970 (3)	0.60288 (15)	0.55199 (14)	0.0556 (5)
C3	0.6430 (3)	0.51560 (18)	0.71349 (17)	0.0360 (5)
C4	0.8056 (3)	0.34403 (19)	0.85758 (18)	0.0385 (5)
H4	0.8125	0.3773	0.9007	0.046*
Br5	0.96940 (5)	0.15148 (2)	1.01371 (3)	0.07361 (13)
C5	0.8708 (3)	0.2340 (2)	0.88452 (19)	0.0426 (5)
C6	0.8650 (4)	0.1838 (2)	0.8206 (2)	0.0500 (6)
H6	0.9128	0.1104	0.8402	0.060*
C7	0.7889 (3)	0.2417 (2)	0.7280 (2)	0.0479 (6)
H7	0.7835	0.2082	0.6849	0.057*
C8	0.7211 (3)	0.35044 (19)	0.70100 (18)	0.0376 (5)
C9	0.7300 (3)	0.40275 (18)	0.76408 (17)	0.0349 (5)
C10	0.6107 (3)	0.60116 (19)	0.73755 (18)	0.0395 (5)
H10	0.5468	0.6637	0.6914	0.047*
C11	0.6620 (3)	0.61086 (17)	0.82716 (17)	0.0353 (5)
C12	0.8280 (3)	0.60502 (19)	0.84706 (18)	0.0397 (5)
Cl12	0.98958 (9)	0.57914 (6)	0.76720 (6)	0.05545 (17)
C13	0.8707 (4)	0.6252 (2)	0.9265 (2)	0.0536 (7)
H13	0.9828	0.6214	0.9374	0.064*
C14	0.7468 (4)	0.6506 (3)	0.9884 (2)	0.0607 (8)
H14	0.7750	0.6635	1.0420	0.073*
C15	0.5811 (4)	0.6572 (2)	0.9723 (2)	0.0543 (7)
H15	0.4968	0.6744	1.0145	0.065*
C16	0.5418 (3)	0.6379 (2)	0.89234 (19)	0.0428 (5)
Cl16	0.33175 (9)	0.64656 (8)	0.87280 (6)	0.0684 (2)
N21	0.8680 (3)	0.62560 (16)	0.40279 (16)	0.0434 (5)
H21	0.8925	0.5598	0.4065	0.052*
C22	0.9185 (3)	0.65805 (19)	0.46956 (18)	0.0419 (5)
O22	1.0070 (3)	0.60169 (14)	0.54175 (14)	0.0579 (5)
C23	0.8454 (3)	0.77842 (18)	0.43524 (18)	0.0390 (5)
C24	0.6607 (3)	0.9048 (2)	0.27961 (19)	0.0430 (5)
H24	0.6485	0.9686	0.2900	0.052*
Br25	0.44460 (5)	1.03332 (3)	0.11691 (2)	0.07282 (12)
C25	0.5849 (3)	0.9036 (2)	0.19976 (19)	0.0474 (6)
C26	0.6033 (4)	0.8103 (2)	0.1816 (2)	0.0521 (6)
H26	0.5526	0.8127	0.1263	0.063*
C27	0.6976 (3)	0.7130 (2)	0.2461 (2)	0.0479 (6)
H27	0.7107	0.6497	0.2349	0.058*
C28	0.7708 (3)	0.71278 (19)	0.32688 (18)	0.0395 (5)
C29	0.7555 (3)	0.80790 (19)	0.34385 (18)	0.0384 (5)
C30	0.8691 (3)	0.83197 (19)	0.48988 (19)	0.0422 (5)
H30	0.9233	0.7892	0.5510	0.051*
C31	0.8202 (3)	0.95013 (19)	0.46537 (18)	0.0400 (5)
C32	0.8786 (3)	1.0363 (2)	0.37702 (19)	0.0431 (6)
Cl32	1.01330 (10)	1.00841 (6)	0.28626 (5)	0.05811 (18)
C33	0.8399 (4)	1.1464 (2)	0.3591 (2)	0.0504 (6)
H33	0.8807	1.2019	0.2991	0.060*
C34	0.7402 (4)	1.1731 (2)	0.4310 (3)	0.0565 (7)
H34	0.7134	1.2470	0.4193	0.068*
C35	0.6804 (4)	1.0910 (2)	0.5199 (2)	0.0547 (7)
H35	0.6124	1.1090	0.5682	0.066*
C36	0.7223 (3)	0.9814 (2)	0.5366 (2)	0.0448 (6)
Cl36	0.65098 (11)	0.87932 (6)	0.65137 (6)	0.0638 (2)

	U11	U22	U33	U12	U13	U23
N1	0.0579 (13)	0.0407 (11)	0.0374 (10)	0.0041 (9)	−0.0129 (9)	−0.0243 (9)
C2	0.0470 (13)	0.0406 (12)	0.0382 (12)	0.0014 (10)	−0.0097 (10)	−0.0217 (10)
O2	0.0774 (13)	0.0466 (10)	0.0478 (10)	0.0152 (9)	−0.0307 (9)	−0.0262 (9)
C3	0.0416 (12)	0.0362 (11)	0.0320 (11)	−0.0009 (9)	−0.0080 (9)	−0.0162 (9)
C4	0.0453 (13)	0.0368 (12)	0.0361 (12)	−0.0017 (10)	−0.0087 (10)	−0.0179 (10)
Br5	0.1111 (3)	0.04428 (16)	0.0599 (2)	0.01126 (16)	−0.04425 (19)	−0.01523 (14)
C5	0.0495 (14)	0.0363 (12)	0.0382 (12)	0.0011 (10)	−0.0125 (10)	−0.0125 (10)
C6	0.0612 (16)	0.0339 (12)	0.0545 (15)	0.0061 (11)	−0.0119 (13)	−0.0208 (11)
C7	0.0598 (16)	0.0417 (13)	0.0503 (15)	0.0029 (11)	−0.0093 (12)	−0.0290 (12)
C8	0.0423 (12)	0.0374 (11)	0.0356 (11)	−0.0015 (9)	−0.0047 (9)	−0.0188 (10)
C9	0.0381 (12)	0.0322 (11)	0.0364 (11)	−0.0014 (9)	−0.0050 (9)	−0.0170 (9)
C10	0.0478 (13)	0.0337 (11)	0.0379 (12)	0.0021 (10)	−0.0131 (10)	−0.0161 (10)
C11	0.0459 (13)	0.0264 (10)	0.0342 (11)	−0.0025 (9)	−0.0085 (9)	−0.0130 (9)
C12	0.0464 (13)	0.0366 (12)	0.0374 (12)	−0.0046 (10)	−0.0031 (10)	−0.0171 (10)
Cl12	0.0489 (4)	0.0663 (4)	0.0600 (4)	−0.0104 (3)	0.0043 (3)	−0.0361 (4)
C13	0.0518 (15)	0.0670 (18)	0.0520 (15)	−0.0146 (13)	−0.0099 (12)	−0.0306 (14)
C14	0.074 (2)	0.076 (2)	0.0509 (16)	−0.0181 (16)	−0.0059 (14)	−0.0415 (16)
C15	0.0632 (18)	0.0613 (17)	0.0472 (15)	−0.0045 (14)	0.0003 (13)	−0.0334 (14)
C16	0.0465 (13)	0.0397 (12)	0.0430 (13)	−0.0008 (10)	−0.0082 (10)	−0.0188 (11)
Cl16	0.0448 (4)	0.0928 (6)	0.0682 (5)	0.0046 (4)	−0.0105 (3)	−0.0384 (4)
N21	0.0603 (13)	0.0286 (9)	0.0432 (11)	0.0016 (9)	−0.0053 (9)	−0.0194 (8)
C22	0.0593 (15)	0.0288 (11)	0.0356 (12)	0.0029 (10)	−0.0043 (11)	−0.0149 (9)
O22	0.0911 (15)	0.0341 (9)	0.0474 (10)	0.0165 (9)	−0.0246 (10)	−0.0201 (8)
C23	0.0516 (14)	0.0281 (10)	0.0367 (12)	0.0038 (10)	−0.0070 (10)	−0.0155 (9)
C24	0.0531 (14)	0.0336 (12)	0.0420 (13)	0.0012 (10)	−0.0065 (11)	−0.0176 (10)
Br25	0.0913 (3)	0.0635 (2)	0.05517 (19)	0.02261 (17)	−0.03042 (17)	−0.02304 (15)
C25	0.0557 (15)	0.0437 (13)	0.0381 (13)	0.0037 (11)	−0.0087 (11)	−0.0156 (11)
C26	0.0622 (17)	0.0571 (16)	0.0437 (14)	−0.0032 (13)	−0.0117 (12)	−0.0272 (13)
C27	0.0614 (16)	0.0445 (14)	0.0469 (14)	−0.0043 (12)	−0.0048 (12)	−0.0283 (12)
C28	0.0472 (13)	0.0340 (11)	0.0376 (12)	−0.0019 (10)	0.0003 (10)	−0.0177 (10)
C29	0.0479 (13)	0.0328 (11)	0.0353 (11)	−0.0007 (10)	−0.0034 (10)	−0.0170 (9)
C30	0.0563 (15)	0.0310 (11)	0.0379 (12)	0.0046 (10)	−0.0117 (11)	−0.0150 (10)
C31	0.0514 (14)	0.0311 (11)	0.0407 (12)	0.0032 (10)	−0.0158 (10)	−0.0182 (10)
C32	0.0559 (15)	0.0360 (12)	0.0414 (13)	0.0028 (11)	−0.0169 (11)	−0.0198 (10)
Cl32	0.0826 (5)	0.0496 (4)	0.0426 (3)	−0.0062 (3)	−0.0018 (3)	−0.0216 (3)
C33	0.0662 (17)	0.0316 (12)	0.0511 (15)	0.0004 (11)	−0.0242 (13)	−0.0129 (11)
C34	0.0621 (17)	0.0323 (12)	0.080 (2)	0.0102 (12)	−0.0234 (15)	−0.0300 (14)
C35	0.0555 (16)	0.0471 (15)	0.0724 (19)	0.0055 (12)	−0.0095 (14)	−0.0382 (15)
C36	0.0538 (15)	0.0372 (12)	0.0480 (14)	−0.0016 (11)	−0.0095 (11)	−0.0226 (11)
Cl36	0.0846 (5)	0.0547 (4)	0.0569 (4)	−0.0150 (4)	0.0079 (4)	−0.0293 (3)

N1—C2	1.358 (3)	N21—C22	1.355 (3)
N1—C8	1.400 (3)	N21—C28	1.402 (3)
N1—H1	0.8600	N21—H21	0.8600
C2—O2	1.222 (3)	C22—O22	1.216 (3)
C2—C3	1.511 (3)	C22—C23	1.512 (3)
C3—C10	1.331 (3)	C23—C30	1.338 (3)
C3—C9	1.462 (3)	C23—C29	1.452 (3)
C4—C9	1.386 (3)	C24—C25	1.382 (4)
C4—C5	1.387 (3)	C24—C29	1.387 (3)
C4—H4	0.9300	C24—H24	0.9300
Br5—C5	1.895 (2)	Br25—C25	1.898 (3)
C5—C6	1.381 (4)	C25—C26	1.384 (4)
C6—C7	1.377 (4)	C26—C27	1.390 (4)
C6—H6	0.9300	C26—H26	0.9300
C7—C8	1.376 (3)	C27—C28	1.374 (3)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.399 (3)	C28—C29	1.401 (3)
C10—C11	1.476 (3)	C30—C31	1.471 (3)
C10—H10	0.9300	C30—H30	0.9300
C11—C16	1.392 (3)	C31—C32	1.392 (4)
C11—C12	1.392 (3)	C31—C36	1.396 (3)
C12—C13	1.389 (3)	C32—C33	1.383 (3)
C12—Cl12	1.734 (2)	C32—Cl32	1.736 (3)
C13—C14	1.367 (4)	C33—C34	1.377 (4)
C13—H13	0.9300	C33—H33	0.9300
C14—C15	1.372 (4)	C34—C35	1.375 (4)
C14—H14	0.9300	C34—H34	0.9300
C15—C16	1.378 (4)	C35—C36	1.383 (4)
C15—H15	0.9300	C35—H35	0.9300
C16—Cl16	1.735 (3)	C36—Cl36	1.734 (3)
C2—N1—C8	111.37 (19)	C22—N21—C28	111.50 (19)
C2—N1—H1	124.3	C22—N21—H21	124.2
C8—N1—H1	124.3	C28—N21—H21	124.2
O2—C2—N1	126.1 (2)	O22—C22—N21	126.6 (2)
O2—C2—C3	127.3 (2)	O22—C22—C23	127.0 (2)
N1—C2—C3	106.56 (19)	N21—C22—C23	106.4 (2)
C10—C3—C9	134.0 (2)	C30—C23—C29	134.6 (2)
C10—C3—C2	120.7 (2)	C30—C23—C22	119.8 (2)
C9—C3—C2	105.30 (18)	C29—C23—C22	105.55 (19)
C9—C4—C5	117.6 (2)	C25—C24—C29	118.0 (2)
C9—C4—H4	121.2	C25—C24—H24	121.0
C5—C4—H4	121.2	C29—C24—H24	121.0
C6—C5—C4	122.1 (2)	C24—C25—C26	122.2 (2)
C6—C5—Br5	119.79 (18)	C24—C25—Br25	117.97 (19)
C4—C5—Br5	118.14 (18)	C26—C25—Br25	119.8 (2)
C7—C6—C5	120.4 (2)	C25—C26—C27	119.9 (2)
C7—C6—H6	119.8	C25—C26—H26	120.0
C5—C6—H6	119.8	C27—C26—H26	120.0
C8—C7—C6	118.2 (2)	C28—C27—C26	118.3 (2)
C8—C7—H7	120.9	C28—C27—H27	120.8
C6—C7—H7	120.9	C26—C27—H27	120.8
C7—C8—C9	121.8 (2)	C27—C28—C29	121.8 (2)
C7—C8—N1	128.7 (2)	C27—C28—N21	129.0 (2)
C9—C8—N1	109.52 (19)	C29—C28—N21	109.2 (2)
C4—C9—C8	119.9 (2)	C24—C29—C28	119.8 (2)
C4—C9—C3	132.8 (2)	C24—C29—C23	132.8 (2)
C8—C9—C3	107.23 (19)	C28—C29—C23	107.3 (2)
C3—C10—C11	129.2 (2)	C23—C30—C31	128.1 (2)
C3—C10—H10	115.4	C23—C30—H30	115.9
C11—C10—H10	115.4	C31—C30—H30	115.9
C16—C11—C12	115.5 (2)	C32—C31—C36	115.8 (2)
C16—C11—C10	120.2 (2)	C32—C31—C30	123.7 (2)
C12—C11—C10	124.0 (2)	C36—C31—C30	120.3 (2)
C13—C12—C11	122.2 (2)	C33—C32—C31	122.6 (2)
C13—C12—Cl12	117.7 (2)	C33—C32—Cl32	116.8 (2)
C11—C12—Cl12	120.01 (18)	C31—C32—Cl32	120.54 (18)
C14—C13—C12	119.5 (3)	C34—C33—C32	119.4 (3)
C14—C13—H13	120.2	C34—C33—H33	120.3
C12—C13—H13	120.2	C32—C33—H33	120.3
C13—C14—C15	120.6 (3)	C35—C34—C33	120.3 (2)
C13—C14—H14	119.7	C35—C34—H34	119.9
C15—C14—H14	119.7	C33—C34—H34	119.9
C14—C15—C16	118.8 (3)	C34—C35—C36	119.3 (3)
C14—C15—H15	120.6	C34—C35—H35	120.4
C16—C15—H15	120.6	C36—C35—H35	120.4
C15—C16—C11	123.3 (2)	C35—C36—C31	122.6 (3)
C15—C16—Cl16	118.3 (2)	C35—C36—Cl36	118.3 (2)
C11—C16—Cl16	118.34 (18)	C31—C36—Cl36	119.07 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O22i	0.86	2.03	2.848 (3)	160
N1—H1···O2ii	0.86	2.09	2.924 (3)	163

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	2.848 (3)	160
N1—H1⋯O2ii	0.86	2.09	2.924 (3)	163

Symmetry codes: (i) ; (ii) .