organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[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.]).

[Scheme 1]

Experimental

Crystal data
  • C11H8BrNO2

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.550, Tmax = 0.625

  • 50850 measured reflections

  • 2983 independent reflections

  • 2345 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.091

  • S = 1.06

  • 2983 reflections

  • 136 parameters

  • H-atom parameters constrained

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.63 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


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.

Refinement top

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.

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
[Figure 1] 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
C11H8BrNO2F(000) = 1056
Mr = 266.09Dx = 1.726 Mg m3
Orthorhombic, PccnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2acCell parameters from 9894 reflections
a = 31.3411 (5) Åθ = 2.6–31.7°
b = 7.8995 (1) ŵ = 3.99 mm1
c = 8.2716 (1) ÅT = 293 K
V = 2047.87 (5) Å3Prism, red
Z = 80.17 × 0.14 × 0.13 mm
Data collection top
Bruker APEX DUO
diffractometer
2983 independent reflections
Radiation source: fine-focus sealed tube2345 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 30.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 4444
Tmin = 0.550, Tmax = 0.625k = 611
50850 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-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 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.63 e Å3
Crystal data top
C11H8BrNO2V = 2047.87 (5) Å3
Mr = 266.09Z = 8
Orthorhombic, PccnMo Kα radiation
a = 31.3411 (5) ŵ = 3.99 mm1
b = 7.8995 (1) ÅT = 293 K
c = 8.2716 (1) Å0.17 × 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)
Tmin = 0.550, Tmax = 0.625Rint = 0.035
50850 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 1.06Δρmax = 0.43 e Å3
2983 reflectionsΔρmin = 0.63 e Å3
136 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.241206 (6)0.49599 (3)0.59089 (3)0.03615 (9)
O10.12709 (5)0.94850 (17)0.22127 (18)0.0334 (3)
O20.06568 (4)0.77943 (19)0.00288 (18)0.0360 (3)
N10.09810 (5)0.5408 (2)0.10576 (18)0.0237 (3)
C10.13156 (5)0.5079 (2)0.2140 (2)0.0204 (3)
C20.14721 (6)0.3526 (2)0.2635 (2)0.0253 (3)
H20.13580.25200.22420.030*
C30.18068 (6)0.3522 (2)0.3744 (2)0.0270 (4)
H30.19190.24970.40980.032*
C40.19752 (6)0.5033 (2)0.4327 (2)0.0250 (3)
C50.18246 (5)0.6597 (2)0.3816 (2)0.0229 (3)
H50.19430.76020.41920.027*
C60.14914 (5)0.6589 (2)0.2724 (2)0.0200 (3)
C70.12453 (5)0.7978 (2)0.2011 (2)0.0229 (3)
C80.09146 (5)0.7101 (2)0.0887 (2)0.0256 (4)
C90.07183 (6)0.4118 (2)0.0275 (2)0.0295 (4)
H9A0.08940.31380.00440.035*
H9B0.06150.45600.07480.035*
C100.03449 (6)0.3572 (3)0.1269 (3)0.0342 (4)
H100.01770.27060.08500.041*
C110.02314 (7)0.4189 (3)0.2666 (3)0.0379 (5)
H11A0.03890.50570.31350.046*
H11B0.00080.37620.31930.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02822 (13)0.04590 (15)0.03435 (13)0.00097 (8)0.00721 (7)0.00370 (8)
O10.0391 (8)0.0187 (6)0.0424 (8)0.0006 (6)0.0109 (6)0.0018 (6)
O20.0273 (6)0.0407 (8)0.0400 (8)0.0049 (6)0.0013 (6)0.0119 (6)
N10.0215 (7)0.0233 (7)0.0264 (7)0.0038 (6)0.0012 (6)0.0004 (6)
C10.0190 (7)0.0200 (7)0.0223 (7)0.0026 (6)0.0031 (6)0.0009 (6)
C20.0287 (9)0.0173 (7)0.0300 (9)0.0020 (6)0.0035 (7)0.0015 (6)
C30.0280 (8)0.0237 (8)0.0292 (8)0.0033 (7)0.0042 (7)0.0033 (7)
C40.0205 (7)0.0303 (9)0.0240 (8)0.0001 (6)0.0014 (6)0.0017 (7)
C50.0215 (7)0.0233 (8)0.0238 (8)0.0034 (6)0.0037 (6)0.0021 (6)
C60.0191 (7)0.0167 (7)0.0241 (8)0.0021 (6)0.0054 (6)0.0009 (6)
C70.0233 (8)0.0193 (7)0.0261 (8)0.0006 (6)0.0087 (6)0.0013 (6)
C80.0203 (7)0.0282 (8)0.0283 (9)0.0002 (6)0.0059 (6)0.0041 (7)
C90.0274 (9)0.0330 (9)0.0280 (9)0.0077 (7)0.0016 (7)0.0066 (7)
C100.0303 (9)0.0370 (10)0.0353 (10)0.0142 (8)0.0030 (8)0.0007 (8)
C110.0307 (10)0.0483 (13)0.0348 (10)0.0133 (9)0.0031 (8)0.0024 (9)
Geometric parameters (Å, º) top
Br1—C41.8950 (19)C4—C51.388 (2)
O1—C71.205 (2)C5—C61.381 (2)
O2—C81.207 (2)C5—H50.9300
N1—C81.361 (2)C6—C71.465 (2)
N1—C11.403 (2)C7—C81.555 (3)
N1—C91.461 (2)C9—C101.494 (3)
C1—C21.383 (2)C9—H9A0.9700
C1—C61.400 (2)C9—H9B0.9700
C2—C31.393 (3)C10—C111.304 (3)
C2—H20.9300C10—H100.9300
C3—C41.392 (3)C11—H11A0.9300
C3—H30.9300C11—H11B0.9300
C8—N1—C1111.23 (14)C1—C6—C7107.00 (15)
C8—N1—C9123.58 (16)O1—C7—C6130.50 (18)
C1—N1—C9125.10 (15)O1—C7—C8124.55 (17)
C2—C1—C6120.94 (16)C6—C7—C8104.94 (14)
C2—C1—N1128.18 (15)O2—C8—N1127.52 (18)
C6—C1—N1110.88 (14)O2—C8—C7126.57 (17)
C1—C2—C3117.64 (16)N1—C8—C7105.90 (15)
C1—C2—H2121.2N1—C9—C10113.51 (16)
C3—C2—H2121.2N1—C9—H9A108.9
C2—C3—C4120.78 (17)C10—C9—H9A108.9
C2—C3—H3119.6N1—C9—H9B108.9
C4—C3—H3119.6C10—C9—H9B108.9
C5—C4—C3121.93 (17)H9A—C9—H9B107.7
C5—C4—Br1118.89 (13)C11—C10—C9126.42 (19)
C3—C4—Br1119.16 (13)C11—C10—H10116.8
C6—C5—C4116.90 (16)C9—C10—H10116.8
C6—C5—H5121.5C10—C11—H11A120.0
C4—C5—H5121.5C10—C11—H11B120.0
C5—C6—C1121.79 (15)H11A—C11—H11B120.0
C5—C6—C7131.16 (15)
C8—N1—C1—C2179.10 (18)N1—C1—C6—C71.88 (19)
C9—N1—C1—C22.4 (3)C5—C6—C7—O10.6 (3)
C8—N1—C1—C60.8 (2)C1—C6—C7—O1176.84 (19)
C9—N1—C1—C6177.57 (16)C5—C6—C7—C8179.54 (17)
C6—C1—C2—C30.6 (3)C1—C6—C7—C82.06 (17)
N1—C1—C2—C3179.32 (17)C1—N1—C8—O2178.62 (17)
C1—C2—C3—C40.1 (3)C9—N1—C8—O24.6 (3)
C2—C3—C4—C51.1 (3)C1—N1—C8—C70.51 (19)
C2—C3—C4—Br1177.05 (14)C9—N1—C8—C7176.28 (15)
C3—C4—C5—C61.4 (3)O1—C7—C8—O23.5 (3)
Br1—C4—C5—C6176.78 (12)C6—C7—C8—O2177.56 (17)
C4—C5—C6—C10.7 (2)O1—C7—C8—N1177.40 (17)
C4—C5—C6—C7176.46 (17)C6—C7—C8—N11.59 (18)
C2—C1—C6—C50.3 (3)C8—N1—C9—C1090.0 (2)
N1—C1—C6—C5179.64 (15)C1—N1—C9—C1086.3 (2)
C2—C1—C6—C7178.08 (16)N1—C9—C10—C113.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.932.413.273 (2)154
C11—H11A···O2ii0.932.463.358 (3)163
Symmetry codes: (i) x, y1, z; (ii) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC11H8BrNO2
Mr266.09
Crystal system, space groupOrthorhombic, Pccn
Temperature (K)293
a, b, c (Å)31.3411 (5), 7.8995 (1), 8.2716 (1)
V3)2047.87 (5)
Z8
Radiation typeMo Kα
µ (mm1)3.99
Crystal size (mm)0.17 × 0.14 × 0.13
Data collection
DiffractometerBruker APEX DUO
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.550, 0.625
No. of measured, independent and
observed [I > 2σ(I)] reflections
50850, 2983, 2345
Rint0.035
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.091, 1.06
No. of reflections2983
No. of parameters136
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C2—H2···O1i0.932.413.273 (2)154
C11—H11A···O2ii0.932.463.358 (3)163
Symmetry codes: (i) x, y1, 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

First citationAbdel-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
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

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ISSN: 2056-9890
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