Methyl 4-anilino-2',5-dioxo-1',2'-di-hydro-5H-spiro-[furan-2,3'-indole]-3-carboxyl-ate.

In the title compound, C19H14N2O5, the spiro junction links an oxindole moeity and a furan ring, which subtend a dihedral angle of 83.49 (6)°. The mol-ecular structure features an N-H⋯O hydrogen bond, which generates an S(6) ring motif. The crystal packing is governed by two N-H⋯O inter-actions, one of which generates a centrosymmetric R 2 (2)(14) dimer. The other N-H⋯O inter-action along with a C-H⋯O hydrogen bond contributes to the formation of a C 2 (2)[R 2 (2)(9)] dimeric chain running along the b-axis direction.

Related literature

For applications of spiro oxindoles, see: Kornet & Thio (1976 ▶); Kobayashi et al. (1991 ▶). For applications of furans, see: Schoop et al. (2000 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶). For a related structure, see: Gayathri et al. (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H14N2O5

M = 350.32

Monoclinic,

a = 12.1713 (6) Å

b = 13.6144 (7) Å

c = 10.9602 (6) Å

β = 114.813 (2)°

V = 1648.50 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.969, T max = 0.979

20901 measured reflections

5167 independent reflections

3502 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.132

S = 1.00

5167 reflections

242 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.16 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014967/rk2403sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014967/rk2403Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014967/rk2403Isup3.cml

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

C19H14N2O5	F(000) = 728
Mr = 350.32	Dx = 1.411 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3502 reflections
a = 12.1713 (6) Å	θ = 2.4–31.0°
b = 13.6144 (7) Å	µ = 0.10 mm−1
c = 10.9602 (6) Å	T = 296 K
β = 114.813 (2)°	Block, yellow
V = 1648.50 (15) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	5167 independent reflections
Radiation source: fine–focus sealed tube	3502 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω– and φ–scans	θmax = 31.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −17→17
Tmin = 0.969, Tmax = 0.979	k = −19→19
20901 measured 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0665P)2 + 0.2325P] where P = (Fo2 + 2Fc2)/3
5167 reflections	(Δ/σ)max = 0.001
242 parameters	Δρmax = 0.26 e Å−3
2 restraints	Δρmin = −0.16 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R–factor wR and goodness of fit S are based on F2, conventional R–factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R–factors(gt) etc. and is not relevant to the choice of reflections for refinement. R–factors based on F2 are statistically about twice as large as those based on F, and R–factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.20517 (13)	0.35795 (13)	0.37822 (16)	0.0565 (4)
H1	0.2233	0.3054	0.3355	0.068*
C2	0.13329 (14)	0.43504 (14)	0.30526 (17)	0.0602 (4)
H2	0.1041	0.4347	0.2121	0.072*
C3	0.10387 (14)	0.51262 (13)	0.36769 (17)	0.0573 (4)
H3	0.0555	0.5635	0.3164	0.069*
C4	0.14643 (12)	0.51452 (11)	0.50668 (16)	0.0494 (3)
H4	0.1265	0.5660	0.5494	0.059*
C5	0.21853 (11)	0.43880 (9)	0.57979 (14)	0.0401 (3)
C6	0.24886 (11)	0.36182 (10)	0.51613 (15)	0.0444 (3)
C7	0.35751 (11)	0.32910 (9)	0.73933 (15)	0.0440 (3)
C8	0.28153 (11)	0.42334 (9)	0.72866 (14)	0.0383 (3)
C9	0.21736 (12)	0.45201 (9)	0.89615 (14)	0.0416 (3)
C10	0.30798 (11)	0.53001 (8)	0.90518 (13)	0.0355 (3)
C11	0.35077 (10)	0.50798 (8)	0.81357 (13)	0.0346 (3)
C12	0.45130 (11)	0.55592 (8)	0.79841 (13)	0.0347 (3)
C13	0.57815 (14)	0.55042 (11)	0.68384 (18)	0.0541 (4)
H13A	0.5593	0.6150	0.6455	0.081*
H13B	0.5951	0.5079	0.6240	0.081*
H13C	0.6477	0.5537	0.7686	0.081*
C14	0.26345 (11)	0.64409 (9)	1.05174 (13)	0.0383 (3)
C15	0.30989 (14)	0.68008 (11)	1.18109 (15)	0.0512 (3)
H15	0.3924	0.6758	1.2355	0.061*
C16	0.23301 (17)	0.72265 (13)	1.22943 (18)	0.0649 (5)
H16	0.2643	0.7472	1.3167	0.078*
C17	0.11072 (16)	0.72924 (13)	1.1501 (2)	0.0646 (5)
H17	0.0594	0.7565	1.1844	0.077*
C18	0.06501 (14)	0.69548 (12)	1.02087 (18)	0.0592 (4)
H18	−0.0174	0.7007	0.9665	0.071*
C19	0.14097 (12)	0.65364 (11)	0.97084 (15)	0.0482 (3)
H19	0.1097	0.6318	0.8823	0.058*
N1	0.32908 (11)	0.29741 (8)	0.61328 (14)	0.0520 (3)
H1A	0.3634 (15)	0.2457 (10)	0.5943 (17)	0.062*
N2	0.34264 (10)	0.60019 (8)	1.00166 (11)	0.0393 (2)
H2A	0.4110 (10)	0.6321 (10)	1.0165 (15)	0.047*
O1	0.42614 (9)	0.29188 (7)	0.84405 (12)	0.0569 (3)
O2	0.19725 (8)	0.39643 (6)	0.78561 (10)	0.0445 (2)
O3	0.17129 (11)	0.43426 (8)	0.96977 (12)	0.0624 (3)
O4	0.47595 (8)	0.51218 (7)	0.70423 (10)	0.0448 (2)
O5	0.50692 (8)	0.62507 (6)	0.86606 (9)	0.0437 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0449 (8)	0.0651 (9)	0.0649 (10)	−0.0106 (7)	0.0283 (8)	−0.0261 (8)
C2	0.0438 (8)	0.0854 (12)	0.0511 (8)	−0.0129 (8)	0.0197 (7)	−0.0146 (8)
C3	0.0410 (7)	0.0686 (10)	0.0575 (9)	0.0008 (7)	0.0160 (7)	0.0021 (8)
C4	0.0405 (7)	0.0483 (7)	0.0580 (9)	0.0048 (6)	0.0193 (7)	−0.0054 (6)
C5	0.0299 (6)	0.0394 (6)	0.0516 (7)	−0.0037 (5)	0.0176 (5)	−0.0109 (5)
C6	0.0326 (6)	0.0419 (6)	0.0606 (8)	−0.0062 (5)	0.0214 (6)	−0.0156 (6)
C7	0.0325 (6)	0.0304 (6)	0.0668 (9)	−0.0038 (5)	0.0186 (6)	−0.0062 (6)
C8	0.0319 (6)	0.0315 (5)	0.0542 (8)	−0.0026 (4)	0.0206 (6)	−0.0058 (5)
C9	0.0381 (6)	0.0368 (6)	0.0533 (8)	−0.0040 (5)	0.0224 (6)	0.0004 (5)
C10	0.0325 (5)	0.0308 (5)	0.0442 (7)	−0.0012 (4)	0.0172 (5)	0.0022 (5)
C11	0.0321 (5)	0.0280 (5)	0.0444 (7)	−0.0020 (4)	0.0167 (5)	−0.0012 (5)
C12	0.0330 (5)	0.0303 (5)	0.0428 (6)	−0.0001 (4)	0.0180 (5)	0.0019 (5)
C13	0.0546 (8)	0.0540 (8)	0.0706 (10)	−0.0117 (7)	0.0429 (8)	−0.0084 (7)
C14	0.0401 (6)	0.0340 (6)	0.0454 (7)	−0.0037 (5)	0.0224 (6)	−0.0024 (5)
C15	0.0463 (7)	0.0529 (8)	0.0534 (8)	−0.0050 (6)	0.0199 (7)	−0.0145 (7)
C16	0.0698 (11)	0.0678 (10)	0.0635 (10)	−0.0082 (8)	0.0344 (9)	−0.0273 (8)
C17	0.0623 (10)	0.0629 (10)	0.0865 (12)	−0.0056 (8)	0.0489 (10)	−0.0207 (9)
C18	0.0431 (8)	0.0626 (9)	0.0763 (11)	−0.0004 (7)	0.0293 (8)	−0.0091 (8)
C19	0.0426 (7)	0.0546 (8)	0.0484 (8)	−0.0004 (6)	0.0200 (6)	−0.0041 (6)
N1	0.0444 (6)	0.0364 (6)	0.0737 (8)	0.0024 (5)	0.0234 (6)	−0.0171 (5)
N2	0.0356 (5)	0.0399 (5)	0.0455 (6)	−0.0056 (4)	0.0200 (5)	−0.0062 (4)
O1	0.0459 (5)	0.0375 (5)	0.0743 (7)	0.0017 (4)	0.0126 (5)	−0.0019 (5)
O2	0.0383 (5)	0.0376 (4)	0.0634 (6)	−0.0096 (4)	0.0268 (5)	−0.0070 (4)
O3	0.0679 (7)	0.0621 (7)	0.0739 (7)	−0.0214 (5)	0.0460 (6)	−0.0051 (6)
O4	0.0443 (5)	0.0417 (5)	0.0575 (6)	−0.0095 (4)	0.0304 (5)	−0.0116 (4)
O5	0.0456 (5)	0.0371 (4)	0.0523 (5)	−0.0115 (4)	0.0245 (4)	−0.0072 (4)

C1—C6	1.377 (2)	C11—C12	1.4564 (16)
C1—C2	1.385 (2)	C12—O5	1.2137 (14)
C1—H1	0.9300	C12—O4	1.3304 (15)
C2—C3	1.385 (2)	C13—O4	1.4498 (16)
C2—H2	0.9300	C13—H13A	0.9600
C3—C4	1.388 (2)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.3729 (19)	C14—C15	1.3773 (19)
C4—H4	0.9300	C14—C19	1.3842 (19)
C5—C6	1.3920 (17)	C14—N2	1.4253 (16)
C5—C8	1.4981 (19)	C15—C16	1.381 (2)
C6—N1	1.4083 (19)	C15—H15	0.9300
C7—O1	1.2112 (17)	C16—C17	1.376 (3)
C7—N1	1.3466 (19)	C16—H16	0.9300
C7—C8	1.5571 (17)	C17—C18	1.366 (2)
C8—O2	1.4537 (15)	C17—H17	0.9300
C8—C11	1.4986 (16)	C18—C19	1.380 (2)
C9—O3	1.1847 (16)	C18—H18	0.9300
C9—O2	1.3607 (17)	C19—H19	0.9300
C9—C10	1.5041 (17)	N1—H1A	0.887 (9)
C10—C11	1.3448 (17)	N2—H2A	0.890 (9)
C10—N2	1.3545 (16)
C6—C1—C2	117.66 (14)	O5—C12—O4	124.86 (11)
C6—C1—H1	121.2	O5—C12—C11	123.91 (11)
C2—C1—H1	121.2	O4—C12—C11	111.20 (10)
C3—C2—C1	121.61 (15)	O4—C13—H13A	109.5
C3—C2—H2	119.2	O4—C13—H13B	109.5
C1—C2—H2	119.2	H13A—C13—H13B	109.5
C2—C3—C4	120.11 (16)	O4—C13—H13C	109.5
C2—C3—H3	119.9	H13A—C13—H13C	109.5
C4—C3—H3	119.9	H13B—C13—H13C	109.5
C5—C4—C3	118.64 (14)	C15—C14—C19	119.50 (12)
C5—C4—H4	120.7	C15—C14—N2	119.60 (12)
C3—C4—H4	120.7	C19—C14—N2	120.88 (12)
C4—C5—C6	120.78 (13)	C14—C15—C16	119.51 (14)
C4—C5—C8	130.60 (12)	C14—C15—H15	120.2
C6—C5—C8	108.54 (11)	C16—C15—H15	120.2
C1—C6—C5	121.17 (14)	C17—C16—C15	120.83 (15)
C1—C6—N1	129.20 (13)	C17—C16—H16	119.6
C5—C6—N1	109.60 (12)	C15—C16—H16	119.6
O1—C7—N1	128.04 (12)	C18—C17—C16	119.66 (14)
O1—C7—C8	124.58 (13)	C18—C17—H17	120.2
N1—C7—C8	107.35 (12)	C16—C17—H17	120.2
O2—C8—C11	103.98 (10)	C17—C18—C19	120.11 (15)
O2—C8—C5	111.85 (10)	C17—C18—H18	119.9
C11—C8—C5	117.76 (11)	C19—C18—H18	119.9
O2—C8—C7	105.30 (10)	C18—C19—C14	120.34 (14)
C11—C8—C7	115.18 (10)	C18—C19—H19	119.8
C5—C8—C7	102.35 (10)	C14—C19—H19	119.8
O3—C9—O2	122.23 (12)	C7—N1—C6	111.98 (11)
O3—C9—C10	130.00 (13)	C7—N1—H1A	123.5 (11)
O2—C9—C10	107.70 (11)	C6—N1—H1A	124.2 (11)
C11—C10—N2	130.46 (11)	C10—N2—C14	123.85 (10)
C11—C10—C9	107.25 (11)	C10—N2—H2A	116.6 (10)
N2—C10—C9	121.93 (11)	C14—N2—H2A	117.1 (10)
C10—C11—C12	126.32 (11)	C9—O2—C8	110.27 (9)
C10—C11—C8	110.00 (10)	C12—O4—C13	116.51 (10)
C12—C11—C8	123.66 (11)
C6—C1—C2—C3	−1.3 (2)	C5—C8—C11—C10	122.03 (12)
C1—C2—C3—C4	−0.1 (2)	C7—C8—C11—C10	−117.01 (12)
C2—C3—C4—C5	0.6 (2)	O2—C8—C11—C12	176.23 (10)
C3—C4—C5—C6	0.3 (2)	C5—C8—C11—C12	−59.41 (15)
C3—C4—C5—C8	176.78 (13)	C7—C8—C11—C12	61.55 (16)
C2—C1—C6—C5	2.1 (2)	C10—C11—C12—O5	−2.4 (2)
C2—C1—C6—N1	−175.49 (13)	C8—C11—C12—O5	179.27 (12)
C4—C5—C6—C1	−1.7 (2)	C10—C11—C12—O4	175.70 (12)
C8—C5—C6—C1	−178.88 (12)	C8—C11—C12—O4	−2.62 (16)
C4—C5—C6—N1	176.37 (12)	C19—C14—C15—C16	1.8 (2)
C8—C5—C6—N1	−0.85 (14)	N2—C14—C15—C16	179.97 (14)
C4—C5—C8—O2	73.88 (17)	C14—C15—C16—C17	0.2 (3)
C6—C5—C8—O2	−109.27 (11)	C15—C16—C17—C18	−1.6 (3)
C4—C5—C8—C11	−46.46 (18)	C16—C17—C18—C19	1.0 (3)
C6—C5—C8—C11	130.39 (11)	C17—C18—C19—C14	1.1 (2)
C4—C5—C8—C7	−173.86 (13)	C15—C14—C19—C18	−2.5 (2)
C6—C5—C8—C7	2.99 (12)	N2—C14—C19—C18	179.41 (13)
O1—C7—C8—O2	−65.30 (15)	O1—C7—N1—C6	−177.92 (13)
N1—C7—C8—O2	112.83 (12)	C8—C7—N1—C6	4.03 (15)
O1—C7—C8—C11	48.61 (18)	C1—C6—N1—C7	175.69 (14)
N1—C7—C8—C11	−133.26 (12)	C5—C6—N1—C7	−2.14 (15)
O1—C7—C8—C5	177.64 (12)	C11—C10—N2—C14	151.63 (13)
N1—C7—C8—C5	−4.23 (13)	C9—C10—N2—C14	−36.17 (18)
O3—C9—C10—C11	167.68 (15)	C15—C14—N2—C10	152.11 (13)
O2—C9—C10—C11	−9.33 (14)	C19—C14—N2—C10	−29.79 (18)
O3—C9—C10—N2	−6.1 (2)	O3—C9—O2—C8	−169.38 (13)
O2—C9—C10—N2	176.87 (11)	C10—C9—O2—C8	7.91 (14)
N2—C10—C11—C12	1.5 (2)	C11—C8—O2—C9	−3.79 (13)
C9—C10—C11—C12	−171.60 (11)	C5—C8—O2—C9	−131.88 (11)
N2—C10—C11—C8	179.99 (12)	C7—C8—O2—C9	117.71 (11)
C9—C10—C11—C8	6.91 (14)	O5—C12—O4—C13	0.81 (19)
O2—C8—C11—C10	−2.33 (13)	C11—C12—O4—C13	−177.27 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5i	0.89 (2)	2.19 (2)	3.0268 (16)	157 (2)
N2—H2A···O1ii	0.89 (1)	2.19 (1)	2.9907 (17)	149 (1)
N2—H2A···O5	0.89 (1)	2.39 (2)	2.9691 (16)	123 (1)
C13—H13A···O1iii	0.96	2.41	3.2999 (18)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5i	0.89 (2)	2.19 (2)	3.0268 (16)	157 (2)
N2—H2A⋯O1ii	0.89 (1)	2.19 (1)	2.9907 (17)	149 (1)
N2—H2A⋯O5	0.89 (1)	2.39 (2)	2.9691 (16)	123 (1)
C13—H13A⋯O1iii	0.96	2.41	3.2999 (18)	153

Symmetry codes: (i) ; (ii) ; (iii) .