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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o454.
Published online 2010 January 27. doi:  10.1107/S1600536810002576
PMCID: PMC2979849

3-[2-(2,3-Dioxoindolin-1-yl)eth­yl]-1,3-oxazolidin-2-one

Abstract

In the title compound, C13H12N2O4, the almost planar (r.m.s. deviation = 0.012 Å) dioxoindolinyl unit and the envelope-shaped oxazolidine ring (with the methyl­ene C atom bonded to the N atom as the flap) are linked by a —CH2—CH2— bridge, in which the N—C—C—N unit adopts a gauche conformation [torsion angle = 62.7 (2)°].

Related literature

For the synthesis of compounds with dioxoindolinyl and oxazolidinyl units, see: Alsubari et al. (2009 [triangle]); Bouhfid et al. (2008 [triangle]).

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Object name is e-66-0o454-scheme1.jpg

Experimental

Crystal data

  • C13H12N2O4
  • M r = 260.25
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o454-efi1.jpg
  • a = 7.1198 (2) Å
  • b = 7.4694 (2) Å
  • c = 12.0319 (3) Å
  • α = 83.338 (2)°
  • β = 79.084 (2)°
  • γ = 81.372 (2)°
  • V = 618.64 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 293 K
  • 0.3 × 0.3 × 0.3 mm

Data collection

  • Bruker APEXII diffractometer
  • 16105 measured reflections
  • 2856 independent reflections
  • 2105 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.129
  • S = 1.07
  • 2856 reflections
  • 172 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [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/S1600536810002576/bt5178sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002576/bt5178Isup2.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

Experimental

Indoline-2, 3-dione (1 g, 6.8 mmol), bis(chloroethyl)amine (0.96 g, 6.8 mmol) and potassium carbonate (1 g, 7.2 mmol) along with catalytic amount of tetra-n-butylammonium bromide were stirred in DMF (30 ml) for 72 h. After the completion of the reaction (as monitored by TLC) , the solid material was removed by filtration and the solvent evaporated under vacuum. Dichloromethane (20 ml) was added and the solution filtered. The solvent was removed and the product purified byrecrystallization from ethanol to afford red crystals in 60% yield . The formulation of the product was established by proton and carbon-13 NMR spectroscopy.

Refinement

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 1.2–1.5U(C).

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C13H12N2O4 at the 50% probability level; hydrogen atoms are drawn as spheres of an arbitrary radius.

Crystal data

C13H12N2O4Z = 2
Mr = 260.25F(000) = 272
Triclinic, P1Dx = 1.397 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1198 (2) ÅCell parameters from 4652 reflections
b = 7.4694 (2) Åθ = 2.7–25.5°
c = 12.0319 (3) ŵ = 0.11 mm1
α = 83.338 (2)°T = 293 K
β = 79.084 (2)°Block, red
γ = 81.372 (2)°0.3 × 0.3 × 0.3 mm
V = 618.64 (3) Å3

Data collection

Bruker APEXII diffractometer2105 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
graphiteθmax = 27.5°, θmin = 1.7°
[var phi] and ω scansh = −9→9
16105 measured reflectionsk = −9→9
2856 independent reflectionsl = −15→15

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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0678P)2 + 0.0776P] where P = (Fo2 + 2Fc2)/3
2856 reflections(Δ/σ)max = 0.001
172 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = −0.21 e Å3

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

xyzUiso*/Ueq
O10.52252 (19)0.72705 (19)0.96655 (11)0.0698 (4)
O20.62176 (17)0.59350 (18)0.80356 (10)0.0650 (4)
O30.0398 (2)1.06952 (18)0.81418 (11)0.0710 (4)
O40.1729 (2)1.32239 (15)0.61954 (12)0.0735 (4)
N10.30085 (18)0.66870 (17)0.87600 (10)0.0465 (3)
N20.13257 (17)0.86176 (15)0.67978 (10)0.0409 (3)
C10.4910 (2)0.6559 (2)0.87395 (13)0.0485 (4)
C20.3389 (3)0.8000 (3)1.02957 (17)0.0723 (5)
H2A0.31860.93161.01670.087*
H2B0.33250.76621.11040.087*
C30.1916 (3)0.7179 (3)0.98519 (14)0.0599 (4)
H3A0.15230.61211.03370.072*
H3B0.07880.80530.97660.072*
C40.2235 (2)0.5789 (2)0.79784 (13)0.0472 (4)
H4A0.17250.47110.83740.057*
H4B0.32670.54050.73690.057*
C50.0649 (2)0.7017 (2)0.74742 (13)0.0470 (4)
H5A0.01160.63300.70000.056*
H5B−0.03780.74040.80850.056*
C60.1067 (2)1.0296 (2)0.71898 (13)0.0477 (4)
C70.1775 (2)1.16148 (19)0.61515 (14)0.0482 (4)
C80.2403 (2)1.04883 (18)0.52062 (12)0.0408 (3)
C90.3139 (2)1.0915 (2)0.40725 (14)0.0520 (4)
H90.33301.21010.37970.062*
C100.3580 (3)0.9532 (3)0.33635 (14)0.0588 (4)
H100.40780.97830.25980.071*
C110.3288 (2)0.7779 (2)0.37813 (14)0.0563 (4)
H110.35890.68700.32850.068*
C120.2556 (2)0.7318 (2)0.49236 (13)0.0464 (4)
H120.23770.61280.51980.056*
C130.21104 (18)0.87131 (18)0.56258 (11)0.0368 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0697 (8)0.0806 (9)0.0668 (8)−0.0181 (7)−0.0215 (6)−0.0121 (7)
O20.0485 (7)0.0773 (8)0.0623 (8)−0.0093 (6)0.0045 (6)0.0006 (6)
O30.0900 (9)0.0660 (8)0.0544 (7)0.0057 (7)−0.0051 (6)−0.0280 (6)
O40.0969 (10)0.0341 (6)0.0964 (10)−0.0070 (6)−0.0291 (8)−0.0164 (6)
N10.0461 (7)0.0516 (7)0.0404 (7)−0.0029 (5)−0.0048 (5)−0.0079 (5)
N20.0463 (7)0.0356 (6)0.0416 (6)−0.0052 (5)−0.0067 (5)−0.0086 (5)
C10.0532 (9)0.0461 (8)0.0448 (8)−0.0110 (7)−0.0066 (7)0.0045 (6)
C20.0919 (15)0.0705 (12)0.0573 (11)−0.0044 (10)−0.0156 (10)−0.0205 (9)
C30.0624 (11)0.0717 (11)0.0414 (9)−0.0004 (8)−0.0018 (7)−0.0108 (8)
C40.0548 (9)0.0405 (7)0.0456 (8)−0.0087 (6)−0.0054 (7)−0.0041 (6)
C50.0440 (8)0.0493 (8)0.0484 (8)−0.0124 (6)−0.0045 (6)−0.0052 (7)
C60.0503 (8)0.0427 (8)0.0515 (9)0.0020 (6)−0.0125 (7)−0.0152 (6)
C70.0504 (8)0.0358 (7)0.0633 (10)−0.0014 (6)−0.0220 (7)−0.0107 (6)
C80.0405 (7)0.0354 (7)0.0496 (8)−0.0031 (5)−0.0170 (6)−0.0048 (6)
C90.0538 (9)0.0514 (9)0.0524 (9)−0.0100 (7)−0.0186 (7)0.0082 (7)
C100.0612 (10)0.0749 (12)0.0403 (9)−0.0089 (8)−0.0113 (7)−0.0011 (8)
C110.0608 (10)0.0628 (10)0.0471 (9)0.0019 (8)−0.0124 (7)−0.0205 (8)
C120.0531 (9)0.0374 (7)0.0505 (9)−0.0023 (6)−0.0118 (7)−0.0123 (6)
C130.0354 (7)0.0358 (7)0.0413 (7)−0.0026 (5)−0.0119 (5)−0.0070 (5)

Geometric parameters (Å, °)

O1—C11.357 (2)C4—H4A0.9700
O1—C21.445 (2)C4—H4B0.9700
O2—C11.2099 (19)C5—H5A0.9700
O3—C61.2072 (18)C5—H5B0.9700
O4—C71.2043 (18)C6—C71.552 (2)
N1—C11.339 (2)C7—C81.455 (2)
N1—C41.4458 (19)C8—C91.384 (2)
N1—C31.4509 (19)C8—C131.394 (2)
N2—C61.3652 (18)C9—C101.378 (2)
N2—C131.4127 (17)C9—H90.9300
N2—C51.4570 (19)C10—C111.378 (3)
C2—C31.497 (3)C10—H100.9300
C2—H2A0.9700C11—C121.397 (2)
C2—H2B0.9700C11—H110.9300
C3—H3A0.9700C12—C131.3799 (19)
C3—H3B0.9700C12—H120.9300
C4—C51.518 (2)
C1—O1—C2108.70 (14)N2—C5—H5A109.0
C1—N1—C4121.55 (12)C4—C5—H5A109.0
C1—N1—C3111.44 (13)N2—C5—H5B109.0
C4—N1—C3123.13 (13)C4—C5—H5B109.0
C6—N2—C13110.57 (12)H5A—C5—H5B107.8
C6—N2—C5123.66 (13)O3—C6—N2127.54 (16)
C13—N2—C5125.33 (11)O3—C6—C7126.54 (14)
O2—C1—N1128.43 (15)N2—C6—C7105.91 (12)
O2—C1—O1122.25 (16)O4—C7—C8131.16 (17)
N1—C1—O1109.31 (14)O4—C7—C6123.49 (15)
O1—C2—C3105.01 (14)C8—C7—C6105.34 (12)
O1—C2—H2A110.7C9—C8—C13121.28 (13)
C3—C2—H2A110.7C9—C8—C7131.54 (14)
O1—C2—H2B110.7C13—C8—C7107.17 (13)
C3—C2—H2B110.7C10—C9—C8118.13 (15)
H2A—C2—H2B108.8C10—C9—H9120.9
N1—C3—C2100.50 (14)C8—C9—H9120.9
N1—C3—H3A111.7C11—C10—C9120.42 (15)
C2—C3—H3A111.7C11—C10—H10119.8
N1—C3—H3B111.7C9—C10—H10119.8
C2—C3—H3B111.7C10—C11—C12122.36 (15)
H3A—C3—H3B109.4C10—C11—H11118.8
N1—C4—C5112.13 (12)C12—C11—H11118.8
N1—C4—H4A109.2C13—C12—C11116.79 (14)
C5—C4—H4A109.2C13—C12—H12121.6
N1—C4—H4B109.2C11—C12—H12121.6
C5—C4—H4B109.2C12—C13—C8121.01 (13)
H4A—C4—H4B107.9C12—C13—N2127.98 (13)
N2—C5—C4112.80 (12)C8—C13—N2111.01 (11)
C4—N1—C1—O210.0 (2)O3—C6—C7—C8−178.75 (15)
C3—N1—C1—O2168.48 (16)N2—C6—C7—C80.25 (15)
C4—N1—C1—O1−170.25 (13)O4—C7—C8—C90.1 (3)
C3—N1—C1—O1−11.80 (18)C6—C7—C8—C9178.84 (14)
C2—O1—C1—O2176.40 (16)O4—C7—C8—C13−178.82 (17)
C2—O1—C1—N1−3.34 (19)C6—C7—C8—C13−0.11 (15)
C1—O1—C2—C316.2 (2)C13—C8—C9—C10−0.1 (2)
C1—N1—C3—C220.76 (19)C7—C8—C9—C10−178.89 (15)
C4—N1—C3—C2178.81 (14)C8—C9—C10—C110.1 (2)
O1—C2—C3—N1−21.31 (19)C9—C10—C11—C12−0.4 (3)
C1—N1—C4—C5−135.55 (14)C10—C11—C12—C130.7 (2)
C3—N1—C4—C568.55 (18)C11—C12—C13—C8−0.6 (2)
C6—N2—C5—C4−99.82 (16)C11—C12—C13—N2178.77 (13)
C13—N2—C5—C488.45 (16)C9—C8—C13—C120.3 (2)
N1—C4—C5—N262.71 (16)C7—C8—C13—C12179.42 (13)
C13—N2—C6—O3178.69 (15)C9—C8—C13—N2−179.15 (12)
C5—N2—C6—O35.9 (2)C7—C8—C13—N2−0.07 (15)
C13—N2—C6—C7−0.30 (15)C6—N2—C13—C12−179.21 (14)
C5—N2—C6—C7−173.10 (12)C5—N2—C13—C12−6.6 (2)
O3—C6—C7—O40.1 (3)C6—N2—C13—C80.24 (16)
N2—C6—C7—O4179.09 (15)C5—N2—C13—C8172.90 (12)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5178).

References

  • Alsubari, A., Bouhfid, R. & Essassi, E. M. (2009). ARKIVOC, xii, 337–346.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bouhfid, R., Joly, N., Ohmani, F., Essassi, E. M., Lequart, V., Banoub, J., Kheddid, K., Charof, R., Massoui, M. & Martin, P. (2008). Lett. Org. Chem pp. 3–7.
  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography