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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1411.
Published online 2010 May 22. doi:  10.1107/S1600536810018271
PMCID: PMC2979628

1-Decyl­indoline-2,3-dione

Abstract

In the title N-alkyl isatin, C18H25NO2, the isatin moiety is almost planar (r.m.s. deviation = 0.03 Å). C—C—C—C torsion angles of the decyl substituent indicate an all-antiperiplanar conformation.

Related literature

For background to N-substituted isatins and their derivatives, see: Bouhfid et al. (2008 [triangle]). For the crystal structures of two N-alkyl isatins, see: see: Miehe et al. (2003 [triangle]); Naumov et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1411-scheme1.jpg

Experimental

Crystal data

  • C18H25NO2
  • M r = 287.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1411-efi1.jpg
  • a = 22.7208 (3) Å
  • b = 4.7189 (1) Å
  • c = 15.8254 (1) Å
  • β = 106.827 (1)°
  • V = 1624.10 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 200 K
  • 0.27 × 0.18 × 0.15 mm

Data collection

  • Bruker X8 APEXII diffractometer
  • 24714 measured reflections
  • 5240 independent reflections
  • 3869 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.154
  • S = 1.03
  • 5240 reflections
  • 190 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.20 e Å−3

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810018271/bt5274sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018271/bt5274Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

N-Substituted isatins (Bouhfid et al., 2008) represent a large family of heterocyclic compounds reported to show a wide range of useful medicinal activities. These are readily synthesized by the reaction of isatin and an alkyl halide in the presence of a catalyst. The title decyl derivative (Scheme I, Fig. 1) has a particarly long hydrocarbon chain; the chain adopts a extended zigzag conformation.

The crystal structures of only few N-substituted isatins have been reported; these have only short hydrocarbon chains, e.g., methyl isatin (Miehe et al., 2003) and ethyl isatin (Naumov et al., 2002).

Experimental

To a solution of isatin (1 g, 6.8 mmol) dissolved in DMF(50 ml) was added 1-bromodecane (1.50 g, 6.8 mmol), potassium carbonate (1 g, 7.4 mmol) and 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 solvent removed under vacuum. The solid that was obtained was recrystallized from ethanol to afford the title compound as orange crystals in 80% yield.

Refinement

H-atoms were placed in calculated positions (C–H 0.95–0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C).

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C18H25NO2F(000) = 624
Mr = 287.39Dx = 1.175 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7695 reflections
a = 22.7208 (3) Åθ = 2.6–30.8°
b = 4.7189 (1) ŵ = 0.08 mm1
c = 15.8254 (1) ÅT = 200 K
β = 106.827 (1)°Prism, orange
V = 1624.10 (4) Å30.27 × 0.18 × 0.15 mm
Z = 4

Data collection

Bruker X8 APEXII diffractometer3869 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
graphiteθmax = 31.2°, θmin = 2.7°
[var phi] and ω scansh = −31→33
24714 measured reflectionsk = −6→6
5240 independent reflectionsl = −23→23

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0928P)2 + 0.1263P] where P = (Fo2 + 2Fc2)/3
5240 reflections(Δ/σ)max = 0.001
190 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = −0.20 e Å3

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

xyzUiso*/Ueq
O10.45133 (4)1.1915 (2)0.42722 (6)0.0500 (2)
O20.35296 (4)0.7723 (2)0.35480 (5)0.0532 (3)
N10.34580 (4)0.78714 (18)0.49718 (5)0.03110 (19)
C10.37349 (4)0.94803 (19)0.57377 (6)0.02594 (19)
C20.36083 (4)0.9424 (2)0.65378 (6)0.0307 (2)
H20.33070.81800.66400.037*
C30.39391 (5)1.1265 (2)0.71908 (7)0.0344 (2)
H30.38591.12750.77480.041*
C40.43815 (5)1.3082 (2)0.70538 (7)0.0361 (2)
H40.45961.43220.75120.043*
C50.45126 (4)1.3101 (2)0.62509 (7)0.0334 (2)
H50.48201.43200.61550.040*
C60.41840 (4)1.1295 (2)0.55931 (6)0.0276 (2)
C70.42008 (4)1.0850 (2)0.46877 (6)0.0337 (2)
C80.36942 (5)0.8606 (2)0.42990 (7)0.0353 (2)
C90.29367 (4)0.5981 (2)0.48624 (8)0.0352 (2)
H9A0.29960.48410.54060.042*
H9B0.29180.46610.43690.042*
C100.23300 (4)0.7587 (2)0.46748 (8)0.0358 (2)
H10A0.23290.87110.52020.043*
H10B0.22990.89260.41820.043*
C110.17722 (5)0.5653 (2)0.44377 (8)0.0357 (2)
H11A0.18060.42940.49260.043*
H11B0.17690.45510.39040.043*
C120.11684 (4)0.7268 (2)0.42654 (8)0.0368 (2)
H12A0.11630.82680.48130.044*
H12B0.11510.87200.38070.044*
C130.05984 (4)0.5417 (2)0.39672 (8)0.0375 (2)
H13A0.06140.39630.44240.045*
H13B0.06010.44210.34180.045*
C140.00008 (4)0.7073 (2)0.38011 (8)0.0385 (2)
H14A−0.00030.80470.43530.046*
H14B−0.00110.85470.33520.046*
C15−0.05752 (5)0.5260 (3)0.34891 (8)0.0387 (2)
H15A−0.05730.42880.29360.046*
H15B−0.05650.37840.39380.046*
C16−0.11691 (5)0.6935 (3)0.33263 (8)0.0395 (3)
H16A−0.11710.78980.38810.047*
H16B−0.11770.84180.28810.047*
C17−0.17475 (5)0.5154 (3)0.30097 (8)0.0447 (3)
H17A−0.17480.42040.24520.054*
H17B−0.17390.36620.34530.054*
C18−0.23353 (5)0.6849 (3)0.28575 (10)0.0566 (4)
H18A−0.26900.55810.26570.085*
H18B−0.23530.82990.24070.085*
H18C−0.23430.77640.34100.085*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0417 (5)0.0751 (6)0.0390 (4)0.0036 (4)0.0209 (4)0.0194 (4)
O20.0543 (5)0.0716 (6)0.0319 (4)0.0113 (5)0.0098 (4)−0.0109 (4)
N10.0264 (4)0.0362 (4)0.0297 (4)0.0000 (3)0.0065 (3)−0.0030 (3)
C10.0214 (4)0.0288 (4)0.0270 (4)0.0035 (3)0.0061 (3)0.0038 (3)
C20.0274 (4)0.0361 (5)0.0309 (5)−0.0008 (4)0.0122 (4)0.0047 (4)
C30.0352 (5)0.0422 (5)0.0269 (5)0.0028 (4)0.0106 (4)0.0015 (4)
C40.0332 (5)0.0385 (5)0.0337 (5)−0.0015 (4)0.0050 (4)−0.0031 (4)
C50.0262 (4)0.0347 (5)0.0378 (5)−0.0025 (4)0.0072 (4)0.0055 (4)
C60.0220 (4)0.0328 (5)0.0290 (4)0.0038 (3)0.0089 (3)0.0071 (3)
C70.0277 (4)0.0452 (6)0.0298 (5)0.0099 (4)0.0107 (4)0.0108 (4)
C80.0312 (5)0.0453 (6)0.0291 (5)0.0121 (4)0.0085 (4)0.0007 (4)
C90.0259 (4)0.0311 (5)0.0447 (6)0.0003 (4)0.0040 (4)−0.0051 (4)
C100.0260 (5)0.0313 (5)0.0464 (6)0.0014 (4)0.0045 (4)−0.0027 (4)
C110.0260 (4)0.0335 (5)0.0442 (6)0.0002 (4)0.0047 (4)−0.0039 (4)
C120.0260 (5)0.0362 (5)0.0454 (6)0.0002 (4)0.0057 (4)−0.0029 (4)
C130.0257 (5)0.0385 (5)0.0457 (6)−0.0002 (4)0.0064 (4)−0.0040 (4)
C140.0253 (5)0.0405 (6)0.0471 (6)0.0003 (4)0.0064 (4)−0.0017 (5)
C150.0264 (5)0.0429 (6)0.0447 (6)−0.0003 (4)0.0068 (4)−0.0052 (5)
C160.0264 (5)0.0451 (6)0.0451 (6)0.0005 (4)0.0072 (4)−0.0012 (5)
C170.0295 (5)0.0528 (7)0.0494 (7)−0.0040 (5)0.0076 (5)−0.0083 (5)
C180.0265 (5)0.0727 (9)0.0673 (9)−0.0007 (6)0.0081 (5)−0.0007 (7)

Geometric parameters (Å, °)

O1—C71.2080 (12)C11—H11A0.9900
O2—C81.2118 (13)C11—H11B0.9900
N1—C81.3684 (13)C12—C131.5196 (15)
N1—C11.4142 (12)C12—H12A0.9900
N1—C91.4525 (13)C12—H12B0.9900
C1—C21.3774 (13)C13—C141.5222 (14)
C1—C61.4007 (13)C13—H13A0.9900
C2—C31.3919 (15)C13—H13B0.9900
C2—H20.9500C14—C151.5213 (14)
C3—C41.3852 (15)C14—H14A0.9900
C3—H30.9500C14—H14B0.9900
C4—C51.3865 (15)C15—C161.5201 (15)
C4—H40.9500C15—H15A0.9900
C5—C61.3846 (14)C15—H15B0.9900
C5—H50.9500C16—C171.5173 (15)
C6—C71.4596 (13)C16—H16A0.9900
C7—C81.5540 (17)C16—H16B0.9900
C9—C101.5248 (14)C17—C181.5151 (17)
C9—H9A0.9900C17—H17A0.9900
C9—H9B0.9900C17—H17B0.9900
C10—C111.5181 (14)C18—H18A0.9800
C10—H10A0.9900C18—H18B0.9800
C10—H10B0.9900C18—H18C0.9800
C11—C121.5233 (14)
C8—N1—C1110.70 (8)H11A—C11—H11B107.8
C8—N1—C9123.56 (9)C13—C12—C11114.23 (9)
C1—N1—C9125.23 (8)C13—C12—H12A108.7
C2—C1—C6121.18 (9)C11—C12—H12A108.7
C2—C1—N1128.18 (9)C13—C12—H12B108.7
C6—C1—N1110.65 (8)C11—C12—H12B108.7
C1—C2—C3117.32 (9)H12A—C12—H12B107.6
C1—C2—H2121.3C12—C13—C14113.32 (9)
C3—C2—H2121.3C12—C13—H13A108.9
C4—C3—C2122.03 (9)C14—C13—H13A108.9
C4—C3—H3119.0C12—C13—H13B108.9
C2—C3—H3119.0C14—C13—H13B108.9
C3—C4—C5120.36 (10)H13A—C13—H13B107.7
C3—C4—H4119.8C15—C14—C13114.06 (9)
C5—C4—H4119.8C15—C14—H14A108.7
C6—C5—C4118.22 (9)C13—C14—H14A108.7
C6—C5—H5120.9C15—C14—H14B108.7
C4—C5—H5120.9C13—C14—H14B108.7
C5—C6—C1120.88 (9)H14A—C14—H14B107.6
C5—C6—C7131.68 (9)C16—C15—C14113.61 (9)
C1—C6—C7107.44 (9)C16—C15—H15A108.8
O1—C7—C6131.37 (11)C14—C15—H15A108.8
O1—C7—C8123.56 (10)C16—C15—H15B108.8
C6—C7—C8105.05 (8)C14—C15—H15B108.8
O2—C8—N1126.65 (11)H15A—C15—H15B107.7
O2—C8—C7127.25 (10)C17—C16—C15114.17 (10)
N1—C8—C7106.08 (8)C17—C16—H16A108.7
N1—C9—C10112.21 (8)C15—C16—H16A108.7
N1—C9—H9A109.2C17—C16—H16B108.7
C10—C9—H9A109.2C15—C16—H16B108.7
N1—C9—H9B109.2H16A—C16—H16B107.6
C10—C9—H9B109.2C18—C17—C16113.55 (11)
H9A—C9—H9B107.9C18—C17—H17A108.9
C11—C10—C9113.10 (8)C16—C17—H17A108.9
C11—C10—H10A109.0C18—C17—H17B108.9
C9—C10—H10A109.0C16—C17—H17B108.9
C11—C10—H10B109.0H17A—C17—H17B107.7
C9—C10—H10B109.0C17—C18—H18A109.5
H10A—C10—H10B107.8C17—C18—H18B109.5
C10—C11—C12112.81 (8)H18A—C18—H18B109.5
C10—C11—H11A109.0C17—C18—H18C109.5
C12—C11—H11A109.0H18A—C18—H18C109.5
C10—C11—H11B109.0H18B—C18—H18C109.5
C12—C11—H11B109.0
C8—N1—C1—C2177.81 (9)C1—N1—C8—O2−175.80 (10)
C9—N1—C1—C25.74 (15)C9—N1—C8—O2−3.58 (17)
C8—N1—C1—C6−1.83 (11)C1—N1—C8—C72.68 (10)
C9—N1—C1—C6−173.90 (9)C9—N1—C8—C7174.90 (8)
C6—C1—C2—C30.75 (14)O1—C7—C8—O2−3.09 (17)
N1—C1—C2—C3−178.85 (9)C6—C7—C8—O2175.90 (10)
C1—C2—C3—C4−0.33 (15)O1—C7—C8—N1178.44 (10)
C2—C3—C4—C5−0.54 (16)C6—C7—C8—N1−2.57 (10)
C3—C4—C5—C60.97 (15)C8—N1—C9—C10−93.70 (12)
C4—C5—C6—C1−0.55 (14)C1—N1—C9—C1077.39 (12)
C4—C5—C6—C7178.57 (10)N1—C9—C10—C11172.33 (9)
C2—C1—C6—C5−0.32 (14)C9—C10—C11—C12179.09 (9)
N1—C1—C6—C5179.35 (8)C10—C11—C12—C13176.17 (10)
C2—C1—C6—C7−179.63 (8)C11—C12—C13—C14179.87 (9)
N1—C1—C6—C70.04 (10)C12—C13—C14—C15179.16 (10)
C5—C6—C7—O11.18 (19)C13—C14—C15—C16179.93 (10)
C1—C6—C7—O1−179.61 (11)C14—C15—C16—C17179.67 (10)
C5—C6—C7—C8−177.70 (10)C15—C16—C17—C18179.53 (11)
C1—C6—C7—C81.50 (10)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5274).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bouhfid, R., Joly, N., Ohmani, F., Essassi, E. M., Massoui, M. & Martin, P. (2008). Lett. Org. Chem. pp. 3–7.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Miehe, G., Süsse, P., Kupcik, V., Egert, E., Nieger, M., Kunz, G., Gerke, R., Knieriem, B., Niemeyer, M. & Lüttke, W. (2003). Angew. Chem. Int. Ed. Engl.30, 964–967.
  • Naumov, P., Anastasova, F., Drew, M. G. B. & Ng, S. W. (2002). Bull. Chem. Technol. Macedon.21, 165–169.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43 Submitted.

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