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

In the title compound, C(13)H(12)N(2)O(4), the almost planar (r.m.s. deviation = 0.012 Å) dioxoindolinyl unit and the envelope-shaped oxazolidine ring (with the methyl-ene C atom bonded to the N atom as the flap) are linked by a -CH(2)-CH(2)- 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 = 260.25

Triclinic,

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 ▶); 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 ▶).

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

C13H12N2O4	Z = 2
Mr = 260.25	F(000) = 272
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0678P)2 + 0.0776P] where P = (Fo2 + 2Fc2)/3
2856 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

	x	y	z	Uiso*/Ueq
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)

	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)

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)