5-Bromo-1-(prop-2-en-1-yl)-2,3-dihydro-1H-indole-2,3-dione

Abstract

In the title compound, C₁₁H₈BrNO₂, the nine-membered fused-ring is nearly planar [maximum deviation = 0.022 (2) Å] and the allyl group is arched over the nine-membered fused-ring at a dihedral angle of 89.2 (1)°. Weak inter­molecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For a related mol­ecule, see: Abdel-Hamid et al. (2009 ▶).

Experimental

Crystal data

• C₁₁H₈BrNO₂

• M _r = 266.09

• Orthorhombic,

• a = 31.3411 (5) Å

• b = 7.8995 (1) Å

• c = 8.2716 (1) Å

• V = 2047.87 (5) ų

• Z = 8

• Mo Kα radiation

• μ = 3.99 mm⁻¹

• T = 293 K

• 0.17 × 0.14 × 0.13 mm

Data collection

• Bruker APEX DUO diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.550, T _max = 0.625

• 50850 measured reflections

• 2983 independent reflections

• 2345 reflections with I > 2σ(I)

• R _int = 0.035

Refinement

• R[F ² > 2σ(F ²)] = 0.029

• wR(F ²) = 0.091

• S = 1.06

• 2983 reflections

• 136 parameters

• H-atom parameters constrained

• Δρ_max = 0.43 e Å⁻³

• Δρ_min = −0.63 e Å⁻³

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Supplementary material file. DOI: 10.1107/S160053681105447X/xu5413Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.41	3.273 (2)	154
C11—H11A⋯O2ii	0.93	2.46	3.358 (3)	163

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

Comment

We are interested in the pharmaceutical properites of isatin derivatives; the allyl group 1-(prop-2-en-1-yl)-2,3-dihydro-1H-indole-2,3-dione, whose crystal structure was recently reported (Abdel-Hamid et al., 2009), is a substituent that can undergo a variety of chemical transformation. The bromo-substituted title compound (Scheme I) features a planar fused-ring; the allyl group is arched over the five-membered ring (dihedral angle between allyl plane and nine-membered fused-ring 89.2 (1)°) (Fig. 1).

Experimental

To a solution of 5-bromo-isatin (1g, 4.4 mmole) in N,N-dimethylformamide (50 ml) was added allyl bromide (1.50 g, 12.5 mmol) potassium carbonate (1 g, 7.4 mmol) along with a catalytic quantity of tetra-n-butylammonium bromide. The mixture was stirred for 48 h. The reaction was monitored by thin layer chromatography. The mixture was filtered and the solution evaporated under vacuum. The solid residue was recrystallized from ethanol to afford the title compound as red crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

Omitted was the 2 0 0 reflection.

Figures

Fig. 1.

Thermal ellipsoid plot (Barbour, 2001) of C11H8BrNO2 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C11H8BrNO2	F(000) = 1056
Mr = 266.09	Dx = 1.726 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 9894 reflections
a = 31.3411 (5) Å	θ = 2.6–31.7°
b = 7.8995 (1) Å	µ = 3.99 mm−1
c = 8.2716 (1) Å	T = 293 K
V = 2047.87 (5) Å3	Prism, red
Z = 8	0.17 × 0.14 × 0.13 mm

Data collection

Bruker APEX DUO diffractometer	2983 independent reflections
Radiation source: fine-focus sealed tube	2345 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω scans	θmax = 30.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −44→44
Tmin = 0.550, Tmax = 0.625	k = −6→11
50850 measured reflections	l = −11→11

Refinement

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0456P)2 + 1.4798P] where P = (Fo2 + 2Fc2)/3
2983 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.63 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.241206 (6)	0.49599 (3)	0.59089 (3)	0.03615 (9)
O1	0.12709 (5)	0.94850 (17)	0.22127 (18)	0.0334 (3)
O2	0.06568 (4)	0.77943 (19)	0.00288 (18)	0.0360 (3)
N1	0.09810 (5)	0.5408 (2)	0.10576 (18)	0.0237 (3)
C1	0.13156 (5)	0.5079 (2)	0.2140 (2)	0.0204 (3)
C2	0.14721 (6)	0.3526 (2)	0.2635 (2)	0.0253 (3)
H2	0.1358	0.2520	0.2242	0.030*
C3	0.18068 (6)	0.3522 (2)	0.3744 (2)	0.0270 (4)
H3	0.1919	0.2497	0.4098	0.032*
C4	0.19752 (6)	0.5033 (2)	0.4327 (2)	0.0250 (3)
C5	0.18246 (5)	0.6597 (2)	0.3816 (2)	0.0229 (3)
H5	0.1943	0.7602	0.4192	0.027*
C6	0.14914 (5)	0.6589 (2)	0.2724 (2)	0.0200 (3)
C7	0.12453 (5)	0.7978 (2)	0.2011 (2)	0.0229 (3)
C8	0.09146 (5)	0.7101 (2)	0.0887 (2)	0.0256 (4)
C9	0.07183 (6)	0.4118 (2)	0.0275 (2)	0.0295 (4)
H9A	0.0894	0.3138	0.0044	0.035*
H9B	0.0615	0.4560	−0.0748	0.035*
C10	0.03449 (6)	0.3572 (3)	0.1269 (3)	0.0342 (4)
H10	0.0177	0.2706	0.0850	0.041*
C11	0.02314 (7)	0.4189 (3)	0.2666 (3)	0.0379 (5)
H11A	0.0389	0.5057	0.3135	0.046*
H11B	−0.0008	0.3762	0.3193	0.046*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Br1	0.02822 (13)	0.04590 (15)	0.03435 (13)	0.00097 (8)	−0.00721 (7)	0.00370 (8)
O1	0.0391 (8)	0.0187 (6)	0.0424 (8)	0.0006 (6)	0.0109 (6)	0.0018 (6)
O2	0.0273 (6)	0.0407 (8)	0.0400 (8)	0.0049 (6)	−0.0013 (6)	0.0119 (6)
N1	0.0215 (7)	0.0233 (7)	0.0264 (7)	−0.0038 (6)	−0.0012 (6)	−0.0004 (6)
C1	0.0190 (7)	0.0200 (7)	0.0223 (7)	−0.0026 (6)	0.0031 (6)	−0.0009 (6)
C2	0.0287 (9)	0.0173 (7)	0.0300 (9)	−0.0020 (6)	0.0035 (7)	−0.0015 (6)
C3	0.0280 (8)	0.0237 (8)	0.0292 (8)	0.0033 (7)	0.0042 (7)	0.0033 (7)
C4	0.0205 (7)	0.0303 (9)	0.0240 (8)	−0.0001 (6)	0.0014 (6)	0.0017 (7)
C5	0.0215 (7)	0.0233 (8)	0.0238 (8)	−0.0034 (6)	0.0037 (6)	−0.0021 (6)
C6	0.0191 (7)	0.0167 (7)	0.0241 (8)	−0.0021 (6)	0.0054 (6)	−0.0009 (6)
C7	0.0233 (8)	0.0193 (7)	0.0261 (8)	−0.0006 (6)	0.0087 (6)	0.0013 (6)
C8	0.0203 (7)	0.0282 (8)	0.0283 (9)	−0.0002 (6)	0.0059 (6)	0.0041 (7)
C9	0.0274 (9)	0.0330 (9)	0.0280 (9)	−0.0077 (7)	−0.0016 (7)	−0.0066 (7)
C10	0.0303 (9)	0.0370 (10)	0.0353 (10)	−0.0142 (8)	−0.0030 (8)	−0.0007 (8)
C11	0.0307 (10)	0.0483 (13)	0.0348 (10)	−0.0133 (9)	0.0031 (8)	0.0024 (9)

Geometric parameters (Å, °)

Br1—C4	1.8950 (19)	C4—C5	1.388 (2)
O1—C7	1.205 (2)	C5—C6	1.381 (2)
O2—C8	1.207 (2)	C5—H5	0.9300
N1—C8	1.361 (2)	C6—C7	1.465 (2)
N1—C1	1.403 (2)	C7—C8	1.555 (3)
N1—C9	1.461 (2)	C9—C10	1.494 (3)
C1—C2	1.383 (2)	C9—H9A	0.9700
C1—C6	1.400 (2)	C9—H9B	0.9700
C2—C3	1.393 (3)	C10—C11	1.304 (3)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.392 (3)	C11—H11A	0.9300
C3—H3	0.9300	C11—H11B	0.9300
C8—N1—C1	111.23 (14)	C1—C6—C7	107.00 (15)
C8—N1—C9	123.58 (16)	O1—C7—C6	130.50 (18)
C1—N1—C9	125.10 (15)	O1—C7—C8	124.55 (17)
C2—C1—C6	120.94 (16)	C6—C7—C8	104.94 (14)
C2—C1—N1	128.18 (15)	O2—C8—N1	127.52 (18)
C6—C1—N1	110.88 (14)	O2—C8—C7	126.57 (17)
C1—C2—C3	117.64 (16)	N1—C8—C7	105.90 (15)
C1—C2—H2	121.2	N1—C9—C10	113.51 (16)
C3—C2—H2	121.2	N1—C9—H9A	108.9
C2—C3—C4	120.78 (17)	C10—C9—H9A	108.9
C2—C3—H3	119.6	N1—C9—H9B	108.9
C4—C3—H3	119.6	C10—C9—H9B	108.9
C5—C4—C3	121.93 (17)	H9A—C9—H9B	107.7
C5—C4—Br1	118.89 (13)	C11—C10—C9	126.42 (19)
C3—C4—Br1	119.16 (13)	C11—C10—H10	116.8
C6—C5—C4	116.90 (16)	C9—C10—H10	116.8
C6—C5—H5	121.5	C10—C11—H11A	120.0
C4—C5—H5	121.5	C10—C11—H11B	120.0
C5—C6—C1	121.79 (15)	H11A—C11—H11B	120.0
C5—C6—C7	131.16 (15)
C8—N1—C1—C2	179.10 (18)	N1—C1—C6—C7	1.88 (19)
C9—N1—C1—C2	2.4 (3)	C5—C6—C7—O1	−0.6 (3)
C8—N1—C1—C6	−0.8 (2)	C1—C6—C7—O1	176.84 (19)
C9—N1—C1—C6	−177.57 (16)	C5—C6—C7—C8	−179.54 (17)
C6—C1—C2—C3	0.6 (3)	C1—C6—C7—C8	−2.06 (17)
N1—C1—C2—C3	−179.32 (17)	C1—N1—C8—O2	178.62 (17)
C1—C2—C3—C4	0.1 (3)	C9—N1—C8—O2	−4.6 (3)
C2—C3—C4—C5	−1.1 (3)	C1—N1—C8—C7	−0.51 (19)
C2—C3—C4—Br1	177.05 (14)	C9—N1—C8—C7	176.28 (15)
C3—C4—C5—C6	1.4 (3)	O1—C7—C8—O2	3.5 (3)
Br1—C4—C5—C6	−176.78 (12)	C6—C7—C8—O2	−177.56 (17)
C4—C5—C6—C1	−0.7 (2)	O1—C7—C8—N1	−177.40 (17)
C4—C5—C6—C7	176.46 (17)	C6—C7—C8—N1	1.59 (18)
C2—C1—C6—C5	−0.3 (3)	C8—N1—C9—C10	−90.0 (2)
N1—C1—C6—C5	179.64 (15)	C1—N1—C9—C10	86.3 (2)
C2—C1—C6—C7	−178.08 (16)	N1—C9—C10—C11	3.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.41	3.273 (2)	154
C11—H11A···O2ii	0.93	2.46	3.358 (3)	163

Symmetry codes: (i) x, y−1, z; (ii) x, −y+3/2, z+1/2.