1'-Methyl-2,2''-dioxoindoline-3-spiro-2'-pyrrolidine-3'-spiro-3''-indoline-4',4'-di-carbonitrile.

In the title compound, C(21)H(15)N(5)O(2), the pyrrolidine ring adopts a twist conformation. Both the oxindole rings are planar [maximum deviations of 0.076 (1) and 0.029 (1) Å in the two rings] and are oriented at a dihedral angle of 72.7 (1)°. The crystal structure is stabilized by C-H⋯O, N-H⋯O, N-H⋯N and C-H⋯π inter-actions.

Related literature

For the use of indole derivatives as bioactive drugs, see: Stevenson et al. (2000 ▶). They exibit anti-allergic, central nervous system depressant and muscle-relaxant properties, see: Harris & Uhle (1960 ▶); Ho et al. (1986 ▶). Indoles also exhibit high aldose reductase inhibitory activity, see: Rajeswaran et al. (1999 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C21H15N5O2

M = 369.38

Monoclinic,

a = 13.3173 (3) Å

b = 9.9480 (2) Å

c = 13.3950 (3) Å

β = 91.827 (1)°

V = 1773.67 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.972, T max = 0.982

26314 measured reflections

6939 independent reflections

4820 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.142

S = 1.02

6939 reflections

263 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028025/bt2998sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028025/bt2998Isup2.hkl

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

C21H15N5O2	F(000) = 768
Mr = 369.38	Dx = 1.383 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3546 reflections
a = 13.3173 (3) Å	θ = 2.1–33.5°
b = 9.9480 (2) Å	µ = 0.09 mm−1
c = 13.3950 (3) Å	T = 293 K
β = 91.827 (1)°	Block, colourless
V = 1773.67 (7) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII area-detector diffractometer	6939 independent reflections
Radiation source: fine-focus sealed tube	4820 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω and φ scans	θmax = 33.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −18→20
Tmin = 0.972, Tmax = 0.982	k = −15→14
26314 measured reflections	l = −20→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0723P)2 + 0.242P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.012
6939 reflections	Δρmax = 0.38 e Å−3
263 parameters	Δρmin = −0.21 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0042 (12)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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
O1	0.62030 (6)	0.88197 (10)	0.24064 (7)	0.0387 (2)
O2	0.24158 (6)	0.73812 (9)	0.25781 (7)	0.03117 (19)
N1	0.59318 (8)	0.75699 (11)	0.09828 (8)	0.0329 (2)
H1	0.6578 (14)	0.7468 (18)	0.0787 (14)	0.058 (5)*
C2	0.56573 (8)	0.82292 (11)	0.18087 (8)	0.0270 (2)
C3	0.44951 (7)	0.81058 (11)	0.18735 (7)	0.02235 (19)
C4	0.42192 (8)	0.73937 (11)	0.09067 (8)	0.0254 (2)
C5	0.33077 (10)	0.71016 (14)	0.04484 (9)	0.0352 (3)
H5	0.2712	0.7316	0.0755	0.042*
C6	0.32903 (11)	0.64796 (15)	−0.04818 (10)	0.0417 (3)
H6	0.2679	0.6272	−0.0799	0.050*
C7	0.41773 (12)	0.61699 (14)	−0.09353 (10)	0.0417 (3)
H7	0.4153	0.5740	−0.1552	0.050*
C8	0.50971 (11)	0.64808 (13)	−0.04977 (9)	0.0362 (3)
H8	0.5692	0.6283	−0.0811	0.043*
C9	0.51005 (9)	0.70967 (11)	0.04223 (8)	0.0281 (2)
C10	0.42527 (7)	0.73565 (10)	0.28602 (7)	0.02080 (18)
C11	0.31810 (8)	0.67524 (11)	0.27584 (8)	0.0236 (2)
N12	0.32571 (7)	0.54152 (10)	0.29159 (8)	0.0301 (2)
H12	0.2748 (13)	0.4894 (17)	0.2909 (12)	0.045 (4)*
C13	0.42464 (8)	0.50270 (11)	0.31500 (8)	0.0273 (2)
C14	0.45870 (11)	0.37590 (13)	0.33844 (11)	0.0386 (3)
H14	0.4152	0.3028	0.3391	0.046*
C15	0.55997 (12)	0.36121 (14)	0.36089 (11)	0.0436 (3)
H15	0.5852	0.2764	0.3767	0.052*
C16	0.62440 (10)	0.46957 (14)	0.36045 (11)	0.0405 (3)
H16	0.6923	0.4570	0.3762	0.049*
C17	0.58894 (8)	0.59738 (13)	0.33672 (9)	0.0316 (2)
H17	0.6325	0.6705	0.3365	0.038*
C18	0.48791 (8)	0.61382 (11)	0.31355 (8)	0.0236 (2)
N19	0.39864 (7)	0.93947 (9)	0.19956 (6)	0.02403 (18)
C20	0.41979 (9)	0.98552 (11)	0.30134 (8)	0.0266 (2)
H20A	0.3668	1.0442	0.3236	0.032*
H20B	0.4831	1.0336	0.3059	0.032*
C21	0.42485 (8)	0.85489 (11)	0.36474 (8)	0.02283 (19)
C22	0.42339 (11)	1.04057 (13)	0.12517 (10)	0.0376 (3)
H22A	0.4939	1.0603	0.1303	0.056*
H22B	0.3857	1.1210	0.1368	0.056*
H22C	0.4068	1.0068	0.0596	0.056*
C23	0.33963 (8)	0.84184 (12)	0.43191 (8)	0.0281 (2)
N24	0.27708 (9)	0.82688 (14)	0.48603 (9)	0.0446 (3)
C25	0.51485 (8)	0.85674 (11)	0.43181 (8)	0.0268 (2)
N26	0.57990 (8)	0.86218 (12)	0.48812 (8)	0.0392 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0260 (4)	0.0448 (5)	0.0452 (5)	−0.0086 (4)	0.0027 (4)	−0.0073 (4)
O2	0.0199 (3)	0.0330 (4)	0.0406 (5)	0.0004 (3)	0.0001 (3)	0.0051 (3)
N1	0.0244 (5)	0.0381 (6)	0.0370 (5)	−0.0003 (4)	0.0122 (4)	−0.0043 (4)
C2	0.0234 (5)	0.0257 (5)	0.0323 (5)	−0.0019 (4)	0.0072 (4)	0.0021 (4)
C3	0.0203 (4)	0.0223 (5)	0.0247 (4)	−0.0001 (4)	0.0050 (3)	0.0000 (4)
C4	0.0275 (5)	0.0251 (5)	0.0240 (5)	0.0005 (4)	0.0052 (4)	0.0001 (4)
C5	0.0318 (6)	0.0435 (7)	0.0303 (5)	−0.0005 (5)	0.0015 (5)	−0.0043 (5)
C6	0.0428 (7)	0.0509 (8)	0.0311 (6)	−0.0057 (6)	−0.0035 (5)	−0.0051 (5)
C7	0.0594 (9)	0.0378 (7)	0.0283 (6)	−0.0034 (6)	0.0073 (6)	−0.0066 (5)
C8	0.0450 (7)	0.0327 (6)	0.0318 (6)	0.0024 (5)	0.0144 (5)	−0.0035 (5)
C9	0.0316 (5)	0.0250 (5)	0.0281 (5)	0.0010 (4)	0.0092 (4)	0.0008 (4)
C10	0.0175 (4)	0.0207 (4)	0.0242 (4)	−0.0003 (3)	0.0021 (3)	0.0001 (3)
C11	0.0212 (4)	0.0254 (5)	0.0243 (4)	−0.0031 (4)	0.0011 (4)	0.0022 (4)
N12	0.0246 (4)	0.0247 (5)	0.0408 (5)	−0.0067 (4)	−0.0023 (4)	0.0056 (4)
C13	0.0278 (5)	0.0239 (5)	0.0301 (5)	−0.0005 (4)	−0.0021 (4)	0.0036 (4)
C14	0.0427 (7)	0.0243 (5)	0.0485 (7)	−0.0005 (5)	−0.0063 (6)	0.0087 (5)
C15	0.0482 (8)	0.0310 (6)	0.0509 (8)	0.0102 (6)	−0.0085 (6)	0.0090 (6)
C16	0.0329 (6)	0.0388 (7)	0.0490 (7)	0.0105 (5)	−0.0097 (5)	0.0019 (6)
C17	0.0245 (5)	0.0308 (6)	0.0394 (6)	0.0025 (4)	−0.0022 (4)	−0.0011 (5)
C18	0.0222 (4)	0.0225 (5)	0.0261 (5)	0.0011 (4)	−0.0002 (4)	0.0007 (4)
N19	0.0274 (4)	0.0206 (4)	0.0243 (4)	0.0015 (3)	0.0058 (3)	0.0027 (3)
C20	0.0305 (5)	0.0207 (5)	0.0286 (5)	−0.0005 (4)	0.0027 (4)	−0.0004 (4)
C21	0.0204 (4)	0.0247 (5)	0.0236 (4)	−0.0003 (4)	0.0035 (3)	−0.0013 (4)
C22	0.0465 (7)	0.0291 (6)	0.0381 (6)	0.0048 (5)	0.0153 (5)	0.0108 (5)
C23	0.0242 (5)	0.0324 (6)	0.0279 (5)	0.0002 (4)	0.0044 (4)	−0.0010 (4)
N24	0.0340 (6)	0.0591 (8)	0.0414 (6)	−0.0017 (5)	0.0139 (5)	−0.0006 (5)
C25	0.0247 (5)	0.0283 (5)	0.0275 (5)	−0.0002 (4)	0.0025 (4)	−0.0031 (4)
N26	0.0328 (5)	0.0475 (7)	0.0370 (5)	0.0005 (5)	−0.0050 (4)	−0.0064 (5)

O1—C2	1.2154 (14)	N12—H12	0.853 (17)
O2—C11	1.2134 (13)	C13—C14	1.3735 (16)
N1—C2	1.3467 (15)	C13—C18	1.3904 (15)
N1—C9	1.3993 (16)	C14—C15	1.380 (2)
N1—H1	0.913 (18)	C14—H14	0.9300
C2—C3	1.5578 (15)	C15—C16	1.378 (2)
C3—N19	1.4618 (13)	C15—H15	0.9300
C3—C4	1.5111 (15)	C16—C17	1.3896 (18)
C3—C10	1.5601 (14)	C16—H16	0.9300
C4—C5	1.3738 (17)	C17—C18	1.3809 (15)
C4—C9	1.3908 (15)	C17—H17	0.9300
C5—C6	1.3908 (18)	N19—C20	1.4572 (14)
C5—H5	0.9300	N19—C22	1.4607 (14)
C6—C7	1.380 (2)	C20—C21	1.5527 (15)
C6—H6	0.9300	C20—H20A	0.9700
C7—C8	1.376 (2)	C20—H20B	0.9700
C7—H7	0.9300	C21—C25	1.4749 (15)
C8—C9	1.3760 (16)	C21—C23	1.4763 (15)
C8—H8	0.9300	C22—H22A	0.9600
C10—C18	1.5103 (14)	C22—H22B	0.9600
C10—C11	1.5505 (14)	C22—H22C	0.9600
C10—C21	1.5871 (14)	C23—N24	1.1314 (14)
C11—N12	1.3502 (14)	C25—N26	1.1317 (15)
N12—C13	1.3989 (15)
C2—N1—C9	111.95 (10)	C14—C13—C18	122.51 (11)
C2—N1—H1	125.0 (12)	C14—C13—N12	127.35 (11)
C9—N1—H1	123.0 (12)	C18—C13—N12	110.14 (9)
O1—C2—N1	127.18 (11)	C13—C14—C15	117.41 (12)
O1—C2—C3	125.15 (10)	C13—C14—H14	121.3
N1—C2—C3	107.67 (10)	C15—C14—H14	121.3
N19—C3—C4	113.97 (9)	C16—C15—C14	121.37 (12)
N19—C3—C2	113.70 (9)	C16—C15—H15	119.3
C4—C3—C2	101.77 (8)	C14—C15—H15	119.3
N19—C3—C10	102.43 (7)	C15—C16—C17	120.64 (12)
C4—C3—C10	116.80 (9)	C15—C16—H16	119.7
C2—C3—C10	108.52 (8)	C17—C16—H16	119.7
C5—C4—C9	119.56 (10)	C18—C17—C16	118.77 (11)
C5—C4—C3	132.01 (10)	C18—C17—H17	120.6
C9—C4—C3	108.28 (10)	C16—C17—H17	120.6
C4—C5—C6	118.92 (11)	C17—C18—C13	119.29 (10)
C4—C5—H5	120.5	C17—C18—C10	132.57 (10)
C6—C5—H5	120.5	C13—C18—C10	108.13 (9)
C7—C6—C5	120.24 (13)	C20—N19—C22	112.38 (9)
C7—C6—H6	119.9	C20—N19—C3	107.70 (8)
C5—C6—H6	119.9	C22—N19—C3	114.34 (9)
C8—C7—C6	121.67 (12)	N19—C20—C21	104.61 (8)
C8—C7—H7	119.2	N19—C20—H20A	110.8
C6—C7—H7	119.2	C21—C20—H20A	110.8
C9—C8—C7	117.32 (12)	N19—C20—H20B	110.8
C9—C8—H8	121.3	C21—C20—H20B	110.8
C7—C8—H8	121.3	H20A—C20—H20B	108.9
C8—C9—C4	122.26 (12)	C25—C21—C23	104.79 (9)
C8—C9—N1	127.61 (11)	C25—C21—C20	110.06 (9)
C4—C9—N1	110.06 (10)	C23—C21—C20	112.71 (9)
C18—C10—C11	102.13 (8)	C25—C21—C10	113.20 (8)
C18—C10—C3	117.56 (8)	C23—C21—C10	111.00 (9)
C11—C10—C3	108.98 (8)	C20—C21—C10	105.26 (8)
C18—C10—C21	116.82 (8)	N19—C22—H22A	109.5
C11—C10—C21	108.99 (8)	N19—C22—H22B	109.5
C3—C10—C21	102.18 (8)	H22A—C22—H22B	109.5
O2—C11—N12	126.68 (10)	N19—C22—H22C	109.5
O2—C11—C10	125.63 (10)	H22A—C22—H22C	109.5
N12—C11—C10	107.69 (9)	H22B—C22—H22C	109.5
C11—N12—C13	111.86 (9)	N24—C23—C21	176.43 (13)
C11—N12—H12	122.8 (11)	N26—C25—C21	175.22 (12)
C13—N12—H12	125.2 (11)
C9—N1—C2—O1	−175.23 (12)	C11—N12—C13—C18	−1.10 (14)
C9—N1—C2—C3	4.82 (13)	C18—C13—C14—C15	−0.1 (2)
O1—C2—C3—N19	52.14 (15)	N12—C13—C14—C15	−178.85 (13)
N1—C2—C3—N19	−127.91 (10)	C13—C14—C15—C16	0.4 (2)
O1—C2—C3—C4	175.14 (12)	C14—C15—C16—C17	−0.3 (2)
N1—C2—C3—C4	−4.91 (11)	C15—C16—C17—C18	0.0 (2)
O1—C2—C3—C10	−61.12 (14)	C16—C17—C18—C13	0.28 (18)
N1—C2—C3—C10	118.84 (10)	C16—C17—C18—C10	179.26 (12)
N19—C3—C4—C5	−49.34 (16)	C14—C13—C18—C17	−0.21 (18)
C2—C3—C4—C5	−172.16 (13)	N12—C13—C18—C17	178.72 (10)
C10—C3—C4—C5	69.89 (16)	C14—C13—C18—C10	−179.42 (11)
N19—C3—C4—C9	126.17 (10)	N12—C13—C18—C10	−0.49 (13)
C2—C3—C4—C9	3.36 (11)	C11—C10—C18—C17	−177.43 (12)
C10—C3—C4—C9	−114.60 (10)	C3—C10—C18—C17	63.40 (16)
C9—C4—C5—C6	1.73 (19)	C21—C10—C18—C17	−58.64 (16)
C3—C4—C5—C6	176.83 (12)	C11—C10—C18—C13	1.63 (11)
C4—C5—C6—C7	−0.3 (2)	C3—C10—C18—C13	−117.54 (10)
C5—C6—C7—C8	−1.1 (2)	C21—C10—C18—C13	120.42 (10)
C6—C7—C8—C9	1.0 (2)	C4—C3—N19—C20	171.14 (9)
C7—C8—C9—C4	0.43 (19)	C2—C3—N19—C20	−72.83 (10)
C7—C8—C9—N1	−176.24 (12)	C10—C3—N19—C20	44.04 (10)
C5—C4—C9—C8	−1.83 (18)	C4—C3—N19—C22	−63.21 (12)
C3—C4—C9—C8	−177.99 (11)	C2—C3—N19—C22	52.83 (13)
C5—C4—C9—N1	175.36 (11)	C10—C3—N19—C22	169.69 (9)
C3—C4—C9—N1	−0.80 (13)	C22—N19—C20—C21	−161.08 (9)
C2—N1—C9—C8	174.33 (12)	C3—N19—C20—C21	−34.26 (10)
C2—N1—C9—C4	−2.67 (14)	N19—C20—C21—C25	132.70 (9)
N19—C3—C10—C18	−163.79 (9)	N19—C20—C21—C23	−110.72 (10)
C4—C3—C10—C18	70.95 (12)	N19—C20—C21—C10	10.40 (10)
C2—C3—C10—C18	−43.27 (12)	C18—C10—C21—C25	24.19 (12)
N19—C3—C10—C11	80.73 (10)	C11—C10—C21—C25	139.22 (9)
C4—C3—C10—C11	−44.53 (12)	C3—C10—C21—C25	−105.56 (9)
C2—C3—C10—C11	−158.75 (8)	C18—C10—C21—C23	−93.33 (11)
N19—C3—C10—C21	−34.50 (9)	C11—C10—C21—C23	21.70 (12)
C4—C3—C10—C21	−159.76 (8)	C3—C10—C21—C23	136.92 (9)
C2—C3—C10—C21	86.02 (9)	C18—C10—C21—C20	144.44 (9)
C18—C10—C11—O2	177.12 (10)	C11—C10—C21—C20	−100.54 (9)
C3—C10—C11—O2	−57.82 (14)	C3—C10—C21—C20	14.69 (10)
C21—C10—C11—O2	52.93 (14)	C25—C21—C23—N24	−44 (2)
C18—C10—C11—N12	−2.28 (11)	C20—C21—C23—N24	−164 (2)
C3—C10—C11—N12	122.78 (9)	C10—C21—C23—N24	78 (2)
C21—C10—C11—N12	−126.47 (9)	C23—C21—C25—N26	−30.2 (16)
O2—C11—N12—C13	−177.24 (11)	C20—C21—C25—N26	91.2 (16)
C10—C11—N12—C13	2.15 (13)	C10—C21—C25—N26	−151.3 (15)
C11—N12—C13—C14	177.75 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2	0.93	2.49	3.1371 (15)	127
C17—H17···O1	0.93	2.47	3.1433 (16)	130
C20—H20B···O1	0.97	2.54	2.9986 (14)	109
C22—H22B···O2i	0.96	2.53	3.3713 (15)	147
N12—H12···O2ii	0.853 (17)	2.591 (17)	3.2114 (13)	130.5 (14)
N12—H12···N19ii	0.853 (17)	2.371 (17)	3.1613 (13)	154.4 (15)
C14—H14···O2ii	0.93	2.51	3.2305 (16)	135
N1—H1···N24iii	0.913 (18)	2.174 (18)	3.0315 (15)	156.1 (16)
C7—H7···Cg5iv	0.93	2.84	3.5366 (15)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2	0.93	2.49	3.1371 (15)	127
C17—H17⋯O1	0.93	2.47	3.1433 (16)	130
C20—H20B⋯O1	0.97	2.54	2.9986 (14)	109
C22—H22B⋯O2i	0.96	2.53	3.3713 (15)	147
N12—H12⋯O2ii	0.853 (17)	2.591 (17)	3.2114 (13)	130.5 (14)
N12—H12⋯N19ii	0.853 (17)	2.371 (17)	3.1613 (13)	154.4 (15)
C14—H14⋯O2ii	0.93	2.51	3.2305 (16)	135
N1—H1⋯N24iii	0.913 (18)	2.174 (18)	3.0315 (15)	156.1 (16)
C7—H7⋯Cg5iv	0.93	2.84	3.5366 (15)	156

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg5 is the centroid of the C13–C18 ring.