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

Al Subari, A.; Bouhfid, R.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810002576

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o454

https://doi.org/10.1107/S1600536810002576

Open

access

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

Abdusalam Al Subari,^a Rachid Bouhfid,^b Hafid Zouihri,^c El Mokhtar Essassi ^a and Seik Weng Ng ^d ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bInstitute of Nanomaterials and Nanotechnology, Avenue de l'Armée Royale, Madinat El Irfane, 10100 Rabat, Morocco, ^cCNRST Division of UATRS Angle Allal Fassi/FAR, BP 8027 Hay Riad, 10000 Rabat, Morocco, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 20 January 2010; accepted 20 January 2010; online 27 January 2010)

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 ); Bouhfid et al. (2008 ).

Experimental

Crystal data

C₁₃H₁₂N₂O₄
M_r = 260.25
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.129
S = 1.07
2856 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); 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: https://doi.org/10.1107/S1600536810002576/bt5178sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002576/bt5178Isup2.hkl

checkCIF report

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₃H₁₂N₂O₄ at the 50% probability level; hydrogen atoms are drawn as spheres of an arbitrary radius.

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

Crystal data top

C₁₃H₁₂N₂O₄	Z = 2
M_r = 260.25	F(000) = 272
Triclinic, P1	D_x = 1.397 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1198 (2) Å	Cell parameters from 4652 reflections
b = 7.4694 (2) Å	θ = 2.7–25.5°
c = 12.0319 (3) Å	µ = 0.11 mm⁻¹
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 top

Bruker APEXII diffractometer	2105 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 27.5°, θ_min = 1.7°
φ and ω scans	h = −9→9
16105 measured reflections	k = −9→9
2856 independent reflections	l = −15→15

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0678P)² + 0.0776P] where P = (F_o² + 2F_c²)/3
2856 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₃H₁₂N₂O₄	γ = 81.372 (2)°
M_r = 260.25	V = 618.64 (3) Å³
Triclinic, P1	Z = 2
a = 7.1198 (2) Å	Mo Kα radiation
b = 7.4694 (2) Å	µ = 0.11 mm⁻¹
c = 12.0319 (3) Å	T = 293 K
α = 83.338 (2)°	0.3 × 0.3 × 0.3 mm
β = 79.084 (2)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.07	Δρ_max = 0.15 e Å⁻³
2856 reflections	Δρ_min = −0.22 e Å⁻³
172 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.52252 (19)	0.72705 (19)	0.96655 (11)	0.0698 (4)
O2	0.62176 (17)	0.59350 (18)	0.80356 (10)	0.0650 (4)
O3	0.0398 (2)	1.06952 (18)	0.81418 (11)	0.0710 (4)
O4	0.1729 (2)	1.32239 (15)	0.61954 (12)	0.0735 (4)
N1	0.30085 (18)	0.66870 (17)	0.87600 (10)	0.0465 (3)
N2	0.13257 (17)	0.86176 (15)	0.67978 (10)	0.0409 (3)
C1	0.4910 (2)	0.6559 (2)	0.87395 (13)	0.0485 (4)
C2	0.3389 (3)	0.8000 (3)	1.02957 (17)	0.0723 (5)
H2A	0.3186	0.9316	1.0167	0.087*
H2B	0.3325	0.7662	1.1104	0.087*
C3	0.1916 (3)	0.7179 (3)	0.98519 (14)	0.0599 (4)
H3A	0.1523	0.6121	1.0337	0.072*
H3B	0.0788	0.8053	0.9766	0.072*
C4	0.2235 (2)	0.5789 (2)	0.79784 (13)	0.0472 (4)
H4A	0.1725	0.4711	0.8374	0.057*
H4B	0.3267	0.5405	0.7369	0.057*
C5	0.0649 (2)	0.7017 (2)	0.74742 (13)	0.0470 (4)
H5A	0.0116	0.6330	0.7000	0.056*
H5B	−0.0378	0.7404	0.8085	0.056*
C6	0.1067 (2)	1.0296 (2)	0.71898 (13)	0.0477 (4)
C7	0.1775 (2)	1.16148 (19)	0.61515 (14)	0.0482 (4)
C8	0.2403 (2)	1.04883 (18)	0.52062 (12)	0.0408 (3)
C9	0.3139 (2)	1.0915 (2)	0.40725 (14)	0.0520 (4)
H9	0.3330	1.2101	0.3797	0.062*
C10	0.3580 (3)	0.9532 (3)	0.33635 (14)	0.0588 (4)
H10	0.4078	0.9783	0.2598	0.071*
C11	0.3288 (2)	0.7779 (2)	0.37813 (14)	0.0563 (4)
H11	0.3589	0.6870	0.3285	0.068*
C12	0.2556 (2)	0.7318 (2)	0.49236 (13)	0.0464 (4)
H12	0.2377	0.6128	0.5198	0.056*
C13	0.21104 (18)	0.87131 (18)	0.56258 (11)	0.0368 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0697 (8)	0.0806 (9)	0.0668 (8)	−0.0181 (7)	−0.0215 (6)	−0.0121 (7)
O2	0.0485 (7)	0.0773 (8)	0.0623 (8)	−0.0093 (6)	0.0045 (6)	0.0006 (6)
O3	0.0900 (9)	0.0660 (8)	0.0544 (7)	0.0057 (7)	−0.0051 (6)	−0.0280 (6)
O4	0.0969 (10)	0.0341 (6)	0.0964 (10)	−0.0070 (6)	−0.0291 (8)	−0.0164 (6)
N1	0.0461 (7)	0.0516 (7)	0.0404 (7)	−0.0029 (5)	−0.0048 (5)	−0.0079 (5)
N2	0.0463 (7)	0.0356 (6)	0.0416 (6)	−0.0052 (5)	−0.0067 (5)	−0.0086 (5)
C1	0.0532 (9)	0.0461 (8)	0.0448 (8)	−0.0110 (7)	−0.0066 (7)	0.0045 (6)
C2	0.0919 (15)	0.0705 (12)	0.0573 (11)	−0.0044 (10)	−0.0156 (10)	−0.0205 (9)
C3	0.0624 (11)	0.0717 (11)	0.0414 (9)	−0.0004 (8)	−0.0018 (7)	−0.0108 (8)
C4	0.0548 (9)	0.0405 (7)	0.0456 (8)	−0.0087 (6)	−0.0054 (7)	−0.0041 (6)
C5	0.0440 (8)	0.0493 (8)	0.0484 (8)	−0.0124 (6)	−0.0045 (6)	−0.0052 (7)
C6	0.0503 (8)	0.0427 (8)	0.0515 (9)	0.0020 (6)	−0.0125 (7)	−0.0152 (6)
C7	0.0504 (8)	0.0358 (7)	0.0633 (10)	−0.0014 (6)	−0.0220 (7)	−0.0107 (6)
C8	0.0405 (7)	0.0354 (7)	0.0496 (8)	−0.0031 (5)	−0.0170 (6)	−0.0048 (6)
C9	0.0538 (9)	0.0514 (9)	0.0524 (9)	−0.0100 (7)	−0.0186 (7)	0.0082 (7)
C10	0.0612 (10)	0.0749 (12)	0.0403 (9)	−0.0089 (8)	−0.0113 (7)	−0.0011 (8)
C11	0.0608 (10)	0.0628 (10)	0.0471 (9)	0.0019 (8)	−0.0124 (7)	−0.0205 (8)
C12	0.0531 (9)	0.0374 (7)	0.0505 (9)	−0.0023 (6)	−0.0118 (7)	−0.0123 (6)
C13	0.0354 (7)	0.0358 (7)	0.0413 (7)	−0.0026 (5)	−0.0119 (5)	−0.0070 (5)

Geometric parameters (Å, º) top

O1—C1	1.357 (2)	C4—H4A	0.9700
O1—C2	1.445 (2)	C4—H4B	0.9700
O2—C1	1.2099 (19)	C5—H5A	0.9700
O3—C6	1.2072 (18)	C5—H5B	0.9700
O4—C7	1.2043 (18)	C6—C7	1.552 (2)
N1—C1	1.339 (2)	C7—C8	1.455 (2)
N1—C4	1.4458 (19)	C8—C9	1.384 (2)
N1—C3	1.4509 (19)	C8—C13	1.394 (2)
N2—C6	1.3652 (18)	C9—C10	1.378 (2)
N2—C13	1.4127 (17)	C9—H9	0.9300
N2—C5	1.4570 (19)	C10—C11	1.378 (3)
C2—C3	1.497 (3)	C10—H10	0.9300
C2—H2A	0.9700	C11—C12	1.397 (2)
C2—H2B	0.9700	C11—H11	0.9300
C3—H3A	0.9700	C12—C13	1.3799 (19)
C3—H3B	0.9700	C12—H12	0.9300
C4—C5	1.518 (2)

C1—O1—C2	108.70 (14)	N2—C5—H5A	109.0
C1—N1—C4	121.55 (12)	C4—C5—H5A	109.0
C1—N1—C3	111.44 (13)	N2—C5—H5B	109.0
C4—N1—C3	123.13 (13)	C4—C5—H5B	109.0
C6—N2—C13	110.57 (12)	H5A—C5—H5B	107.8
C6—N2—C5	123.66 (13)	O3—C6—N2	127.54 (16)
C13—N2—C5	125.33 (11)	O3—C6—C7	126.54 (14)
O2—C1—N1	128.43 (15)	N2—C6—C7	105.91 (12)
O2—C1—O1	122.25 (16)	O4—C7—C8	131.16 (17)
N1—C1—O1	109.31 (14)	O4—C7—C6	123.49 (15)
O1—C2—C3	105.01 (14)	C8—C7—C6	105.34 (12)
O1—C2—H2A	110.7	C9—C8—C13	121.28 (13)
C3—C2—H2A	110.7	C9—C8—C7	131.54 (14)
O1—C2—H2B	110.7	C13—C8—C7	107.17 (13)
C3—C2—H2B	110.7	C10—C9—C8	118.13 (15)
H2A—C2—H2B	108.8	C10—C9—H9	120.9
N1—C3—C2	100.50 (14)	C8—C9—H9	120.9
N1—C3—H3A	111.7	C11—C10—C9	120.42 (15)
C2—C3—H3A	111.7	C11—C10—H10	119.8
N1—C3—H3B	111.7	C9—C10—H10	119.8
C2—C3—H3B	111.7	C10—C11—C12	122.36 (15)
H3A—C3—H3B	109.4	C10—C11—H11	118.8
N1—C4—C5	112.13 (12)	C12—C11—H11	118.8
N1—C4—H4A	109.2	C13—C12—C11	116.79 (14)
C5—C4—H4A	109.2	C13—C12—H12	121.6
N1—C4—H4B	109.2	C11—C12—H12	121.6
C5—C4—H4B	109.2	C12—C13—C8	121.01 (13)
H4A—C4—H4B	107.9	C12—C13—N2	127.98 (13)
N2—C5—C4	112.80 (12)	C8—C13—N2	111.01 (11)

C4—N1—C1—O2	10.0 (2)	O3—C6—C7—C8	−178.75 (15)
C3—N1—C1—O2	168.48 (16)	N2—C6—C7—C8	0.25 (15)
C4—N1—C1—O1	−170.25 (13)	O4—C7—C8—C9	0.1 (3)
C3—N1—C1—O1	−11.80 (18)	C6—C7—C8—C9	178.84 (14)
C2—O1—C1—O2	176.40 (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—C3	16.2 (2)	C13—C8—C9—C10	−0.1 (2)
C1—N1—C3—C2	20.76 (19)	C7—C8—C9—C10	−178.89 (15)
C4—N1—C3—C2	178.81 (14)	C8—C9—C10—C11	0.1 (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—C13	0.7 (2)
C3—N1—C4—C5	68.55 (18)	C11—C12—C13—C8	−0.6 (2)
C6—N2—C5—C4	−99.82 (16)	C11—C12—C13—N2	178.77 (13)
C13—N2—C5—C4	88.45 (16)	C9—C8—C13—C12	0.3 (2)
N1—C4—C5—N2	62.71 (16)	C7—C8—C13—C12	179.42 (13)
C13—N2—C6—O3	178.69 (15)	C9—C8—C13—N2	−179.15 (12)
C5—N2—C6—O3	5.9 (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—O4	0.1 (3)	C6—N2—C13—C8	0.24 (16)
N2—C6—C7—O4	179.09 (15)	C5—N2—C13—C8	172.90 (12)

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₂O₄
M_r	260.25
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.1198 (2), 7.4694 (2), 12.0319 (3)
α, β, γ (°)	83.338 (2), 79.084 (2), 81.372 (2)
V (Å³)	618.64 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.3 × 0.3 × 0.3

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16105, 2856, 2105
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.129, 1.07
No. of reflections	2856
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.22

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

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

References

Alsubari, A., Bouhfid, R. & Essassi, E. M. (2009). ARKIVOC, xii, 337–346. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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. Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar