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

The title compound, C(19)H(16)N(4)O(2), 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 ethyl-ene 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 ▶). For a related structure, see: Alsubari et al. (2010 ▶)

Experimental

Crystal data

C19H16N4O2

M = 332.36

Monoclinic,

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 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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/S1600536810033222/fl2310sup1.cif

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

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

C19H16N4O2	F(000) = 696
Mr = 332.36	Dx = 1.380 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2575 reflections
a = 14.5565 (4) Å	θ = 2.8–21.3°
b = 5.8993 (2) Å	µ = 0.09 mm−1
c = 18.6434 (6) Å	T = 293 K
β = 92.393 (2)°	Prism, yellow
V = 1599.57 (9) Å3	0.37 × 0.18 × 0.17 mm
Z = 4

Bruker X8 APEXII diffractometer	1897 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
graphite	θmax = 26.3°, θmin = 2.8°
φ and ω scans	h = −18→18
19296 measured reflections	k = −7→7
3216 independent reflections	l = −23→23

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0947P)2] where P = (Fo2 + 2Fc2)/3
3216 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.14976 (14)	0.4457 (3)	0.30554 (10)	0.0756 (6)
O2	0.09479 (13)	0.3291 (3)	0.41022 (10)	0.0765 (6)
N1	0.38685 (12)	0.2701 (3)	0.50246 (9)	0.0499 (5)
N2	0.32451 (12)	0.6823 (3)	0.43058 (9)	0.0493 (5)
N3	0.21587 (12)	0.6899 (3)	0.52289 (9)	0.0491 (5)
N4	0.10754 (12)	0.7065 (3)	0.38211 (9)	0.0449 (4)
C1	0.42821 (14)	0.3536 (4)	0.44272 (11)	0.0455 (5)
C2	0.50363 (16)	0.2364 (4)	0.41630 (12)	0.0536 (6)
H2	0.5235	0.1027	0.4383	0.064*
C3	0.54794 (16)	0.3169 (4)	0.35861 (12)	0.0571 (6)
H3	0.5980	0.2382	0.3418	0.069*
C4	0.51867 (16)	0.5176 (4)	0.32443 (12)	0.0573 (6)
H4	0.5496	0.5713	0.2852	0.069*
C5	0.44540 (15)	0.6342 (4)	0.34824 (12)	0.0519 (6)
H5	0.4262	0.7664	0.3249	0.062*
C6	0.39828 (14)	0.5568 (4)	0.40790 (10)	0.0434 (5)
C7	0.28851 (14)	0.5993 (4)	0.48773 (11)	0.0448 (5)
C8	0.31888 (14)	0.3950 (4)	0.52400 (11)	0.0446 (5)
C9	0.26054 (15)	0.3687 (4)	0.58425 (11)	0.0477 (5)
C10	0.25656 (16)	0.2117 (4)	0.64019 (12)	0.0593 (6)
H10	0.2985	0.0928	0.6437	0.071*
C11	0.19041 (17)	0.2347 (5)	0.68979 (14)	0.0693 (7)
H11	0.1874	0.1309	0.7272	0.083*
C12	0.12790 (18)	0.4118 (5)	0.68458 (13)	0.0713 (8)
H12	0.0829	0.4229	0.7184	0.086*
C13	0.13042 (17)	0.5719 (5)	0.63082 (12)	0.0624 (7)
H13	0.0884	0.6907	0.6282	0.075*
C14	0.19776 (15)	0.5498 (4)	0.58088 (11)	0.0480 (6)
C15	0.15862 (15)	0.8786 (4)	0.49739 (11)	0.0505 (6)
H15A	0.1961	0.9839	0.4714	0.061*
H15B	0.1353	0.9582	0.5384	0.061*
C16	0.07797 (15)	0.8028 (4)	0.44871 (12)	0.0483 (6)
H16A	0.0424	0.6908	0.4737	0.058*
H16B	0.0384	0.9317	0.4381	0.058*
C17	0.11498 (16)	0.4834 (4)	0.37101 (13)	0.0539 (6)
C18	0.1696 (2)	0.6593 (5)	0.27265 (14)	0.0742 (8)
H18A	0.1341	0.6763	0.2278	0.089*
H18B	0.2344	0.6699	0.2630	0.089*
C19	0.14339 (19)	0.8400 (4)	0.32542 (12)	0.0616 (7)
H19A	0.1965	0.9276	0.3421	0.074*
H19B	0.0971	0.9416	0.3046	0.074*

	U11	U22	U33	U12	U13	U23
O1	0.1126 (15)	0.0451 (11)	0.0699 (11)	0.0048 (9)	0.0125 (11)	−0.0150 (8)
O2	0.0993 (14)	0.0362 (10)	0.0947 (14)	−0.0026 (9)	0.0106 (11)	0.0101 (9)
N1	0.0567 (11)	0.0489 (11)	0.0437 (10)	0.0008 (9)	−0.0010 (9)	0.0018 (8)
N2	0.0515 (11)	0.0515 (11)	0.0446 (10)	0.0010 (9)	0.0001 (9)	0.0027 (8)
N3	0.0496 (11)	0.0537 (12)	0.0442 (10)	0.0081 (9)	0.0031 (9)	0.0015 (8)
N4	0.0569 (11)	0.0318 (10)	0.0459 (10)	0.0031 (8)	−0.0002 (8)	−0.0013 (8)
C1	0.0486 (12)	0.0489 (13)	0.0387 (11)	−0.0020 (10)	−0.0038 (10)	−0.0051 (9)
C2	0.0602 (14)	0.0534 (14)	0.0467 (13)	0.0070 (11)	−0.0034 (11)	−0.0031 (11)
C3	0.0562 (14)	0.0647 (16)	0.0507 (14)	0.0115 (12)	0.0040 (11)	−0.0073 (12)
C4	0.0571 (15)	0.0726 (17)	0.0426 (12)	−0.0010 (13)	0.0062 (11)	−0.0009 (12)
C5	0.0539 (13)	0.0558 (15)	0.0460 (12)	0.0022 (11)	0.0012 (11)	0.0057 (11)
C6	0.0434 (12)	0.0499 (13)	0.0366 (11)	0.0014 (10)	−0.0034 (9)	−0.0038 (9)
C7	0.0471 (12)	0.0466 (13)	0.0401 (11)	−0.0011 (10)	−0.0041 (10)	−0.0004 (10)
C8	0.0462 (12)	0.0438 (13)	0.0430 (11)	−0.0005 (10)	−0.0072 (10)	−0.0009 (10)
C9	0.0466 (12)	0.0526 (14)	0.0436 (12)	−0.0055 (10)	−0.0022 (10)	0.0002 (10)
C10	0.0585 (14)	0.0619 (16)	0.0573 (15)	−0.0005 (12)	−0.0025 (12)	0.0096 (12)
C11	0.0661 (16)	0.083 (2)	0.0587 (16)	−0.0056 (15)	0.0070 (13)	0.0199 (14)
C12	0.0602 (16)	0.102 (2)	0.0523 (14)	−0.0002 (16)	0.0111 (12)	0.0145 (15)
C13	0.0573 (15)	0.0779 (18)	0.0524 (14)	0.0068 (13)	0.0057 (12)	0.0027 (13)
C14	0.0483 (13)	0.0553 (14)	0.0401 (11)	−0.0023 (10)	−0.0031 (10)	0.0013 (10)
C15	0.0596 (14)	0.0442 (13)	0.0479 (13)	0.0055 (10)	0.0024 (11)	−0.0064 (10)
C16	0.0494 (12)	0.0401 (13)	0.0558 (13)	0.0085 (10)	0.0059 (10)	0.0024 (10)
C17	0.0604 (15)	0.0371 (13)	0.0639 (15)	0.0037 (10)	−0.0018 (12)	−0.0045 (11)
C18	0.104 (2)	0.0604 (18)	0.0588 (16)	−0.0010 (14)	0.0136 (15)	−0.0080 (12)
C19	0.0917 (18)	0.0481 (15)	0.0453 (13)	0.0035 (13)	0.0039 (12)	0.0037 (10)

O1—C17	1.359 (3)	C7—C8	1.442 (3)
O1—C18	1.436 (3)	C8—C9	1.445 (3)
O2—C17	1.211 (3)	C9—C10	1.398 (3)
N1—C8	1.310 (3)	C9—C14	1.406 (3)
N1—C1	1.379 (3)	C10—C11	1.369 (3)
N2—C7	1.302 (3)	C10—H10	0.9300
N2—C6	1.385 (3)	C11—C12	1.386 (4)
N3—C7	1.375 (3)	C11—H11	0.9300
N3—C14	1.395 (3)	C12—C13	1.379 (3)
N3—C15	1.458 (3)	C12—H12	0.9300
N4—C17	1.338 (3)	C13—C14	1.386 (3)
N4—C19	1.434 (3)	C13—H13	0.9300
N4—C16	1.447 (3)	C15—C16	1.521 (3)
C1—C2	1.404 (3)	C15—H15A	0.9700
C1—C6	1.423 (3)	C15—H15B	0.9700
C2—C3	1.362 (3)	C16—H16A	0.9700
C2—H2	0.9300	C16—H16B	0.9700
C3—C4	1.402 (3)	C18—C19	1.510 (3)
C3—H3	0.9300	C18—H18A	0.9700
C4—C5	1.359 (3)	C18—H18B	0.9700
C4—H4	0.9300	C19—H19A	0.9700
C5—C6	1.407 (3)	C19—H19B	0.9700
C5—H5	0.9300
C17—O1—C18	109.19 (18)	C10—C11—C12	120.3 (2)
C8—N1—C1	114.03 (19)	C10—C11—H11	119.8
C7—N2—C6	113.11 (18)	C12—C11—H11	119.8
C7—N3—C14	108.24 (18)	C13—C12—C11	122.0 (2)
C7—N3—C15	125.57 (18)	C13—C12—H12	119.0
C14—N3—C15	125.53 (18)	C11—C12—H12	119.0
C17—N4—C19	113.09 (19)	C12—C13—C14	117.7 (2)
C17—N4—C16	123.23 (19)	C12—C13—H13	121.1
C19—N4—C16	123.19 (18)	C14—C13—H13	121.1
N1—C1—C2	118.8 (2)	C13—C14—N3	128.8 (2)
N1—C1—C6	122.26 (19)	C13—C14—C9	121.2 (2)
C2—C1—C6	118.94 (19)	N3—C14—C9	109.98 (19)
C3—C2—C1	120.5 (2)	N3—C15—C16	112.74 (18)
C3—C2—H2	119.7	N3—C15—H15A	109.0
C1—C2—H2	119.7	C16—C15—H15A	109.0
C2—C3—C4	120.5 (2)	N3—C15—H15B	109.0
C2—C3—H3	119.7	C16—C15—H15B	109.0
C4—C3—H3	119.7	H15A—C15—H15B	107.8
C5—C4—C3	120.4 (2)	N4—C16—C15	112.19 (17)
C5—C4—H4	119.8	N4—C16—H16A	109.2
C3—C4—H4	119.8	C15—C16—H16A	109.2
C4—C5—C6	120.6 (2)	N4—C16—H16B	109.2
C4—C5—H5	119.7	C15—C16—H16B	109.2
C6—C5—H5	119.7	H16A—C16—H16B	107.9
N2—C6—C5	118.5 (2)	O2—C17—N4	128.5 (2)
N2—C6—C1	122.53 (18)	O2—C17—O1	121.9 (2)
C5—C6—C1	118.95 (19)	N4—C17—O1	109.6 (2)
N2—C7—N3	126.0 (2)	O1—C18—C19	106.30 (19)
N2—C7—C8	124.87 (19)	O1—C18—H18A	110.5
N3—C7—C8	109.16 (18)	C19—C18—H18A	110.5
N1—C8—C7	123.16 (19)	O1—C18—H18B	110.5
N1—C8—C9	130.8 (2)	C19—C18—H18B	110.5
C7—C8—C9	106.00 (18)	H18A—C18—H18B	108.7
C10—C9—C14	119.3 (2)	N4—C19—C18	101.7 (2)
C10—C9—C8	134.1 (2)	N4—C19—H19A	111.4
C14—C9—C8	106.60 (18)	C18—C19—H19A	111.4
C11—C10—C9	119.4 (2)	N4—C19—H19B	111.4
C11—C10—H10	120.3	C18—C19—H19B	111.4
C9—C10—H10	120.3	H19A—C19—H19B	109.3
C8—N1—C1—C2	178.18 (19)	C14—C9—C10—C11	1.3 (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—C12	0.0 (4)
C6—C1—C2—C3	0.6 (3)	C10—C11—C12—C13	−1.0 (4)
C1—C2—C3—C4	−0.3 (3)	C11—C12—C13—C14	0.6 (4)
C2—C3—C4—C5	−0.2 (4)	C12—C13—C14—N3	−178.6 (2)
C3—C4—C5—C6	0.6 (3)	C12—C13—C14—C9	0.9 (3)
C7—N2—C6—C5	−177.54 (18)	C7—N3—C14—C13	−179.2 (2)
C7—N2—C6—C1	2.3 (3)	C15—N3—C14—C13	−8.2 (4)
C4—C5—C6—N2	179.5 (2)	C7—N3—C14—C9	1.2 (2)
C4—C5—C6—C1	−0.4 (3)	C15—N3—C14—C9	172.27 (19)
N1—C1—C6—N2	−1.3 (3)	C10—C9—C14—C13	−1.8 (3)
C2—C1—C6—N2	179.99 (19)	C8—C9—C14—C13	178.8 (2)
N1—C1—C6—C5	178.46 (19)	C10—C9—C14—N3	177.76 (19)
C2—C1—C6—C5	−0.2 (3)	C8—C9—C14—N3	−1.6 (2)
C6—N2—C7—N3	178.79 (19)	C7—N3—C15—C16	87.4 (3)
C6—N2—C7—C8	−1.6 (3)	C14—N3—C15—C16	−82.2 (2)
C14—N3—C7—N2	179.42 (19)	C17—N4—C16—C15	98.1 (2)
C15—N3—C7—N2	8.3 (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—O2	176.5 (3)
C1—N1—C8—C7	1.2 (3)	C16—N4—C17—O2	4.4 (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—N1	179.50 (19)	C18—O1—C17—O2	−178.2 (2)
N2—C7—C8—C9	179.6 (2)	C18—O1—C17—N4	2.2 (3)
N3—C7—C8—C9	−0.7 (2)	C17—O1—C18—C19	0.2 (3)
N1—C8—C9—C10	1.9 (4)	C17—N4—C19—C18	3.8 (3)
C7—C8—C9—C10	−177.9 (2)	C16—N4—C19—C18	175.9 (2)
N1—C8—C9—C14	−178.8 (2)	O1—C18—C19—N4	−2.3 (3)
C7—C8—C9—C14	1.4 (2)