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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2461.
Published online 2010 August 28. doi:  10.1107/S1600536810033222
PMCID: PMC3008062

3-[2-(5H-Indolo[2,3-b]quinoxalin-5-yl)eth­yl]-1,3-oxazolidin-2-one

Abstract

The title compound, C19H16N4O2, has an almost planar fused N-heterocyclic system (r.m.s. deviation = 0.031 Å) and an almost planar five-membered 1,3-oxazolidine ring (r.m.s. deviation = 0.015 Å) at the ends of an ethyl­ene chain [N—C—C—N torsion angle = −65.6 (2)°]. The ring systems are inclined at 38.1 (1)° to one another.

Related literature

For background to this class of oxindole derivatives, see: Alsubari et al. (2009 [triangle]). For a related structure, see: Alsubari et al. (2010 [triangle])

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Object name is e-66-o2461-scheme1.jpg

Experimental

Crystal data

  • C19H16N4O2
  • M r = 332.36
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2461-efi1.jpg
  • a = 14.5565 (4) Å
  • b = 5.8993 (2) Å
  • c = 18.6434 (6) Å
  • β = 92.393 (2)°
  • V = 1599.57 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.37 × 0.18 × 0.17 mm

Data collection

  • Bruker X8 APEXII diffractometer
  • 19296 measured reflections
  • 3216 independent reflections
  • 1897 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.152
  • S = 0.95
  • 3216 reflections
  • 226 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.15 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/S1600536810033222/fl2310sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033222/fl2310Isup2.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

The synthesis of new oxindole derivatives having an oxazolindin-2-one unit has been detailed in a recent report (Alsubari et al., 2009). Among related compounds whose structures have been determined is 3-[2-(2,3-dioxoindolin-1-yl)ethyl]-1,3-oxazolidin-2-one (Alsubari et al., 2010) in which the oxazolidinyl ring has an envelope conformation with the methylene C atom bonded to the N atom as the flap. The –CH2–CH2– connecting this ring to the other fused-ring system has its substituents in a gauche conformation [torsion angle = 62.7 (2)°]. In the tite compound (Scheme I, Fig. 1), the oxazolidinyl ring is planar (rms 0.015 Å), and there is no indication of any disorder in the ethylene portion of the ring. The fused N-heterocyclic system (rms 0.031 Å) is also planar and the two ring systems are inclined at 38.1 (1)° to one another. . The fused-rings are not stacked directly over one another, however, the distance between two inversion-related fused ring systems is only 3.4 Å (Fig. 2).

Experimental

1-(2-(2-Oxoxazolidin-3-yl)ethyl)indoline-2,3-dione (0.5 g, 3.84 mmole) and o-phenylenediamine (0.41 g, 3.84 mmole) were heated in xylene (30 ml) and refluxed for twelve hours. The solvent was then removed under reduced pressure and the residue recrystallized from ethanol to afford the title compound as yellow 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 1.2Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid plot of the title compound at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Two molecules disposed about a center-of-inversion.

Crystal data

C19H16N4O2F(000) = 696
Mr = 332.36Dx = 1.380 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2575 reflections
a = 14.5565 (4) Åθ = 2.8–21.3°
b = 5.8993 (2) ŵ = 0.09 mm1
c = 18.6434 (6) ÅT = 293 K
β = 92.393 (2)°Prism, yellow
V = 1599.57 (9) Å30.37 × 0.18 × 0.17 mm
Z = 4

Data collection

Bruker X8 APEXII diffractometer1897 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
graphiteθmax = 26.3°, θmin = 2.8°
[var phi] and ω scansh = −18→18
19296 measured reflectionsk = −7→7
3216 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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 0.95w = 1/[σ2(Fo2) + (0.0947P)2] where P = (Fo2 + 2Fc2)/3
3216 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = −0.15 e Å3

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

xyzUiso*/Ueq
O10.14976 (14)0.4457 (3)0.30554 (10)0.0756 (6)
O20.09479 (13)0.3291 (3)0.41022 (10)0.0765 (6)
N10.38685 (12)0.2701 (3)0.50246 (9)0.0499 (5)
N20.32451 (12)0.6823 (3)0.43058 (9)0.0493 (5)
N30.21587 (12)0.6899 (3)0.52289 (9)0.0491 (5)
N40.10754 (12)0.7065 (3)0.38211 (9)0.0449 (4)
C10.42821 (14)0.3536 (4)0.44272 (11)0.0455 (5)
C20.50363 (16)0.2364 (4)0.41630 (12)0.0536 (6)
H20.52350.10270.43830.064*
C30.54794 (16)0.3169 (4)0.35861 (12)0.0571 (6)
H30.59800.23820.34180.069*
C40.51867 (16)0.5176 (4)0.32443 (12)0.0573 (6)
H40.54960.57130.28520.069*
C50.44540 (15)0.6342 (4)0.34824 (12)0.0519 (6)
H50.42620.76640.32490.062*
C60.39828 (14)0.5568 (4)0.40790 (10)0.0434 (5)
C70.28851 (14)0.5993 (4)0.48773 (11)0.0448 (5)
C80.31888 (14)0.3950 (4)0.52400 (11)0.0446 (5)
C90.26054 (15)0.3687 (4)0.58425 (11)0.0477 (5)
C100.25656 (16)0.2117 (4)0.64019 (12)0.0593 (6)
H100.29850.09280.64370.071*
C110.19041 (17)0.2347 (5)0.68979 (14)0.0693 (7)
H110.18740.13090.72720.083*
C120.12790 (18)0.4118 (5)0.68458 (13)0.0713 (8)
H120.08290.42290.71840.086*
C130.13042 (17)0.5719 (5)0.63082 (12)0.0624 (7)
H130.08840.69070.62820.075*
C140.19776 (15)0.5498 (4)0.58088 (11)0.0480 (6)
C150.15862 (15)0.8786 (4)0.49739 (11)0.0505 (6)
H15A0.19610.98390.47140.061*
H15B0.13530.95820.53840.061*
C160.07797 (15)0.8028 (4)0.44871 (12)0.0483 (6)
H16A0.04240.69080.47370.058*
H16B0.03840.93170.43810.058*
C170.11498 (16)0.4834 (4)0.37101 (13)0.0539 (6)
C180.1696 (2)0.6593 (5)0.27265 (14)0.0742 (8)
H18A0.13410.67630.22780.089*
H18B0.23440.66990.26300.089*
C190.14339 (19)0.8400 (4)0.32542 (12)0.0616 (7)
H19A0.19650.92760.34210.074*
H19B0.09710.94160.30460.074*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.1126 (15)0.0451 (11)0.0699 (11)0.0048 (9)0.0125 (11)−0.0150 (8)
O20.0993 (14)0.0362 (10)0.0947 (14)−0.0026 (9)0.0106 (11)0.0101 (9)
N10.0567 (11)0.0489 (11)0.0437 (10)0.0008 (9)−0.0010 (9)0.0018 (8)
N20.0515 (11)0.0515 (11)0.0446 (10)0.0010 (9)0.0001 (9)0.0027 (8)
N30.0496 (11)0.0537 (12)0.0442 (10)0.0081 (9)0.0031 (9)0.0015 (8)
N40.0569 (11)0.0318 (10)0.0459 (10)0.0031 (8)−0.0002 (8)−0.0013 (8)
C10.0486 (12)0.0489 (13)0.0387 (11)−0.0020 (10)−0.0038 (10)−0.0051 (9)
C20.0602 (14)0.0534 (14)0.0467 (13)0.0070 (11)−0.0034 (11)−0.0031 (11)
C30.0562 (14)0.0647 (16)0.0507 (14)0.0115 (12)0.0040 (11)−0.0073 (12)
C40.0571 (15)0.0726 (17)0.0426 (12)−0.0010 (13)0.0062 (11)−0.0009 (12)
C50.0539 (13)0.0558 (15)0.0460 (12)0.0022 (11)0.0012 (11)0.0057 (11)
C60.0434 (12)0.0499 (13)0.0366 (11)0.0014 (10)−0.0034 (9)−0.0038 (9)
C70.0471 (12)0.0466 (13)0.0401 (11)−0.0011 (10)−0.0041 (10)−0.0004 (10)
C80.0462 (12)0.0438 (13)0.0430 (11)−0.0005 (10)−0.0072 (10)−0.0009 (10)
C90.0466 (12)0.0526 (14)0.0436 (12)−0.0055 (10)−0.0022 (10)0.0002 (10)
C100.0585 (14)0.0619 (16)0.0573 (15)−0.0005 (12)−0.0025 (12)0.0096 (12)
C110.0661 (16)0.083 (2)0.0587 (16)−0.0056 (15)0.0070 (13)0.0199 (14)
C120.0602 (16)0.102 (2)0.0523 (14)−0.0002 (16)0.0111 (12)0.0145 (15)
C130.0573 (15)0.0779 (18)0.0524 (14)0.0068 (13)0.0057 (12)0.0027 (13)
C140.0483 (13)0.0553 (14)0.0401 (11)−0.0023 (10)−0.0031 (10)0.0013 (10)
C150.0596 (14)0.0442 (13)0.0479 (13)0.0055 (10)0.0024 (11)−0.0064 (10)
C160.0494 (12)0.0401 (13)0.0558 (13)0.0085 (10)0.0059 (10)0.0024 (10)
C170.0604 (15)0.0371 (13)0.0639 (15)0.0037 (10)−0.0018 (12)−0.0045 (11)
C180.104 (2)0.0604 (18)0.0588 (16)−0.0010 (14)0.0136 (15)−0.0080 (12)
C190.0917 (18)0.0481 (15)0.0453 (13)0.0035 (13)0.0039 (12)0.0037 (10)

Geometric parameters (Å, °)

O1—C171.359 (3)C7—C81.442 (3)
O1—C181.436 (3)C8—C91.445 (3)
O2—C171.211 (3)C9—C101.398 (3)
N1—C81.310 (3)C9—C141.406 (3)
N1—C11.379 (3)C10—C111.369 (3)
N2—C71.302 (3)C10—H100.9300
N2—C61.385 (3)C11—C121.386 (4)
N3—C71.375 (3)C11—H110.9300
N3—C141.395 (3)C12—C131.379 (3)
N3—C151.458 (3)C12—H120.9300
N4—C171.338 (3)C13—C141.386 (3)
N4—C191.434 (3)C13—H130.9300
N4—C161.447 (3)C15—C161.521 (3)
C1—C21.404 (3)C15—H15A0.9700
C1—C61.423 (3)C15—H15B0.9700
C2—C31.362 (3)C16—H16A0.9700
C2—H20.9300C16—H16B0.9700
C3—C41.402 (3)C18—C191.510 (3)
C3—H30.9300C18—H18A0.9700
C4—C51.359 (3)C18—H18B0.9700
C4—H40.9300C19—H19A0.9700
C5—C61.407 (3)C19—H19B0.9700
C5—H50.9300
C17—O1—C18109.19 (18)C10—C11—C12120.3 (2)
C8—N1—C1114.03 (19)C10—C11—H11119.8
C7—N2—C6113.11 (18)C12—C11—H11119.8
C7—N3—C14108.24 (18)C13—C12—C11122.0 (2)
C7—N3—C15125.57 (18)C13—C12—H12119.0
C14—N3—C15125.53 (18)C11—C12—H12119.0
C17—N4—C19113.09 (19)C12—C13—C14117.7 (2)
C17—N4—C16123.23 (19)C12—C13—H13121.1
C19—N4—C16123.19 (18)C14—C13—H13121.1
N1—C1—C2118.8 (2)C13—C14—N3128.8 (2)
N1—C1—C6122.26 (19)C13—C14—C9121.2 (2)
C2—C1—C6118.94 (19)N3—C14—C9109.98 (19)
C3—C2—C1120.5 (2)N3—C15—C16112.74 (18)
C3—C2—H2119.7N3—C15—H15A109.0
C1—C2—H2119.7C16—C15—H15A109.0
C2—C3—C4120.5 (2)N3—C15—H15B109.0
C2—C3—H3119.7C16—C15—H15B109.0
C4—C3—H3119.7H15A—C15—H15B107.8
C5—C4—C3120.4 (2)N4—C16—C15112.19 (17)
C5—C4—H4119.8N4—C16—H16A109.2
C3—C4—H4119.8C15—C16—H16A109.2
C4—C5—C6120.6 (2)N4—C16—H16B109.2
C4—C5—H5119.7C15—C16—H16B109.2
C6—C5—H5119.7H16A—C16—H16B107.9
N2—C6—C5118.5 (2)O2—C17—N4128.5 (2)
N2—C6—C1122.53 (18)O2—C17—O1121.9 (2)
C5—C6—C1118.95 (19)N4—C17—O1109.6 (2)
N2—C7—N3126.0 (2)O1—C18—C19106.30 (19)
N2—C7—C8124.87 (19)O1—C18—H18A110.5
N3—C7—C8109.16 (18)C19—C18—H18A110.5
N1—C8—C7123.16 (19)O1—C18—H18B110.5
N1—C8—C9130.8 (2)C19—C18—H18B110.5
C7—C8—C9106.00 (18)H18A—C18—H18B108.7
C10—C9—C14119.3 (2)N4—C19—C18101.7 (2)
C10—C9—C8134.1 (2)N4—C19—H19A111.4
C14—C9—C8106.60 (18)C18—C19—H19A111.4
C11—C10—C9119.4 (2)N4—C19—H19B111.4
C11—C10—H10120.3C18—C19—H19B111.4
C9—C10—H10120.3H19A—C19—H19B109.3
C8—N1—C1—C2178.18 (19)C14—C9—C10—C111.3 (3)
C8—N1—C1—C6−0.5 (3)C8—C9—C10—C11−179.5 (2)
N1—C1—C2—C3−178.2 (2)C9—C10—C11—C120.0 (4)
C6—C1—C2—C30.6 (3)C10—C11—C12—C13−1.0 (4)
C1—C2—C3—C4−0.3 (3)C11—C12—C13—C140.6 (4)
C2—C3—C4—C5−0.2 (4)C12—C13—C14—N3−178.6 (2)
C3—C4—C5—C60.6 (3)C12—C13—C14—C90.9 (3)
C7—N2—C6—C5−177.54 (18)C7—N3—C14—C13−179.2 (2)
C7—N2—C6—C12.3 (3)C15—N3—C14—C13−8.2 (4)
C4—C5—C6—N2179.5 (2)C7—N3—C14—C91.2 (2)
C4—C5—C6—C1−0.4 (3)C15—N3—C14—C9172.27 (19)
N1—C1—C6—N2−1.3 (3)C10—C9—C14—C13−1.8 (3)
C2—C1—C6—N2179.99 (19)C8—C9—C14—C13178.8 (2)
N1—C1—C6—C5178.46 (19)C10—C9—C14—N3177.76 (19)
C2—C1—C6—C5−0.2 (3)C8—C9—C14—N3−1.6 (2)
C6—N2—C7—N3178.79 (19)C7—N3—C15—C1687.4 (3)
C6—N2—C7—C8−1.6 (3)C14—N3—C15—C16−82.2 (2)
C14—N3—C7—N2179.42 (19)C17—N4—C16—C1598.1 (2)
C15—N3—C7—N28.3 (3)C19—N4—C16—C15−73.2 (3)
C14—N3—C7—C8−0.3 (2)N3—C15—C16—N4−65.6 (2)
C15—N3—C7—C8−171.34 (18)C19—N4—C17—O2176.5 (3)
C1—N1—C8—C71.2 (3)C16—N4—C17—O24.4 (4)
C1—N1—C8—C9−178.5 (2)C19—N4—C17—O1−4.0 (3)
N2—C7—C8—N1−0.2 (3)C16—N4—C17—O1−176.09 (18)
N3—C7—C8—N1179.50 (19)C18—O1—C17—O2−178.2 (2)
N2—C7—C8—C9179.6 (2)C18—O1—C17—N42.2 (3)
N3—C7—C8—C9−0.7 (2)C17—O1—C18—C190.2 (3)
N1—C8—C9—C101.9 (4)C17—N4—C19—C183.8 (3)
C7—C8—C9—C10−177.9 (2)C16—N4—C19—C18175.9 (2)
N1—C8—C9—C14−178.8 (2)O1—C18—C19—N4−2.3 (3)
C7—C8—C9—C141.4 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2310).

References

  • Alsubari, A., Bouhfid, R. & Essassi, E. M. (2009). ARKIVOC, xii, 337–346.
  • Alsubari, A., Bouhfid, R., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o454 [PMC free article] [PubMed]
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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