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

Maamri, K.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S160053681105447X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o240

doi:10.1107/S160053681105447X

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

Khalil Maamri,^a Hafid Zouihri,^b El Mokhtar Essassi ^a and Seik Weng Ng ^c,^d ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, Rabat, Morocco, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 17 December 2011; accepted 18 December 2011; online 23 December 2011)

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, P c c n
a = 31.3411 (5) Å
b = 7.8995 (1) Å
c = 8.2716 (1) Å
V = 2047.87 (5) Å³
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[F² > 2σ(F²)] = 0.029
wR(F²) = 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

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) x, y-1, z; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681105447X/xu5413sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681105447X/xu5413Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681105447X/xu5413Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₁H₈BrNO₂ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

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

Crystal data top

C₁₁H₈BrNO₂	F(000) = 1056
M_r = 266.09	D_x = 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 top

Bruker APEX DUO diffractometer	2983 independent reflections
Radiation source: fine-focus sealed tube	2345 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω scans	θ_max = 30.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −44→44
T_min = 0.550, T_max = 0.625	k = −6→11
50850 measured reflections	l = −11→11

Refinement top

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(F_o²) + (0.0456P)² + 1.4798P] where P = (F_o² + 2F_c²)/3
2983 reflections	(Δ/σ)_max = 0.001
136 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₁₁H₈BrNO₂	V = 2047.87 (5) Å³
M_r = 266.09	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 31.3411 (5) Å	µ = 3.99 mm⁻¹
b = 7.8995 (1) Å	T = 293 K
c = 8.2716 (1) Å	0.17 × 0.14 × 0.13 mm

Data collection top

Bruker APEX DUO diffractometer	2983 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2345 reflections with I > 2σ(I)
T_min = 0.550, T_max = 0.625	R_int = 0.035
50850 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.06	Δρ_max = 0.43 e Å⁻³
2983 reflections	Δρ_min = −0.63 e Å⁻³
136 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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.

Experimental details

Crystal data
Chemical formula	C₁₁H₈BrNO₂
M_r	266.09
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	293
a, b, c (Å)	31.3411 (5), 7.8995 (1), 8.2716 (1)
V (Å³)	2047.87 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.99
Crystal size (mm)	0.17 × 0.14 × 0.13

Data collection
Diffractometer	Bruker APEX DUO diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.550, 0.625
No. of measured, independent and observed [I > 2σ(I)] reflections	50850, 2983, 2345
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.091, 1.06
No. of reflections	2983
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.63

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Abdel-Hamid, M. K., Bremner, J. B., Coates, J., Keller, P. A., Miländer, C., Torkamani, Y. S., Skelton, B. W., White, A. H. & Willis, A. C. (2009). Tetrahedron Lett. 50, 6947–6950. CAS Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar