3-(2,3-Dioxoindolin-1-yl)propane-nitrile.

The asymmetric unit of the title compound, C11H8N2O2, contains two independent mol-ecules (A and B). Each mol-ecule is build up from fused five- and six-membered rings with the former linked to a cyano-ethyl group. The indoline ring and two carbonyl O atoms of each mol-ecule are nearly coplanar, with the largest deviations from the mean planes being 0.0198 (9) (mol-ecule A) and 0.0902 (9) Å (mol-ecule B), each by a carbonyl O atom. The fused ring system is nearly perpendicular to the mean plane passing through the cyano-ethyl chains, as indicated by the dihedral angles between them of 69.72 (9) (mol-ecule A) and 69.15 (9)° (mol-ecule B). In the crystal, mol-ecules are linked by C-H⋯O and π-π [inter-centroid distance between inversion-related indoline (A) rings = 3.6804 (7) Å] inter-actions into a double layer that stacks along the a-axis direction.

Related literature

For biological activity of indoline derivatives, see: Bhrigu et al. (2010 ▶); Ramachandran (2011 ▶); Smitha et al. (2008 ▶). For similar structures, see: Qachchachi et al. (2013 ▶, 2014 ▶).

Experimental

Crystal data

C11H8N2O2

M = 200.19

Triclinic,

a = 7.1967 (2) Å

b = 9.9909 (3) Å

c = 13.5534 (5) Å

α = 77.508 (3)°

β = 81.551 (3)°

γ = 77.717 (3)°

V = 924.44 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.84 mm−1

T = 123 K

0.26 × 0.17 × 0.12 mm

Data collection

Agilent SuperNova (Single source at offset, Atlas) diffractometer

Absorption correction: analytical (Clark & Reid, 1995 ▶) T min = 0.827, T max = 0.917

5751 measured reflections

3546 independent reflections

3292 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.086

S = 1.07

3546 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814003985/tk5297sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003985/tk5297Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003985/tk5297Isup3.cml

CCDC reference: 988036

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H8N2O2	Z = 4
Mr = 200.19	F(000) = 416
Triclinic, P1	Dx = 1.438 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 7.1967 (2) Å	Cell parameters from 4004 reflections
b = 9.9909 (3) Å	θ = 4.6–73.3°
c = 13.5534 (5) Å	µ = 0.84 mm−1
α = 77.508 (3)°	T = 123 K
β = 81.551 (3)°	Plate, orange
γ = 77.717 (3)°	0.26 × 0.17 × 0.12 mm
V = 924.44 (5) Å3

Agilent SuperNova (Single source at offset, Atlas) diffractometer	3546 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3292 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.013
Detector resolution: 10.3546 pixels mm-1	θmax = 73.7°, θmin = 4.6°
ω scans	h = −8→8
Absorption correction: analytical (Clark & Reid, 1995)	k = −12→9
Tmin = 0.827, Tmax = 0.917	l = −16→16
5751 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0448P)2 + 0.2333P] where P = (Fo2 + 2Fc2)/3
3546 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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 > 2σ(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	0.35182 (15)	0.75842 (11)	1.04434 (8)	0.0189 (2)
C2	0.27845 (15)	0.61738 (11)	1.07606 (8)	0.0193 (2)
C3	0.27526 (15)	0.57304 (11)	0.98035 (8)	0.0181 (2)
C4	0.33583 (14)	0.67561 (11)	0.90158 (8)	0.0171 (2)
C5	0.34919 (16)	0.66466 (11)	0.80081 (8)	0.0196 (2)
H5	0.3914	0.7340	0.7475	0.023*
C6	0.29746 (16)	0.54636 (11)	0.78129 (9)	0.0213 (2)
H6	0.3044	0.5357	0.7128	0.026*
C7	0.23621 (16)	0.44382 (11)	0.85865 (9)	0.0218 (2)
H7	0.2015	0.3652	0.8423	0.026*
C8	0.22547 (15)	0.45570 (11)	0.95987 (9)	0.0201 (2)
H8	0.1853	0.3857	1.0133	0.024*
C9	0.44795 (16)	0.90577 (11)	0.87921 (8)	0.0210 (2)
H9A	0.5298	0.8784	0.8187	0.025*
H9B	0.5278	0.9390	0.9189	0.025*
C10	0.28577 (18)	1.02563 (12)	0.84414 (9)	0.0253 (2)
H10A	0.3403	1.0976	0.7927	0.030*
H10B	0.1974	0.9897	0.8113	0.030*
C11	0.17723 (17)	1.09045 (11)	0.92779 (9)	0.0241 (2)
C12	0.35805 (16)	0.79086 (12)	1.50595 (9)	0.0231 (2)
C13	0.30355 (17)	0.93949 (12)	1.53235 (9)	0.0232 (2)
C14	0.22133 (16)	1.02896 (12)	1.44313 (9)	0.0220 (2)
C15	0.22224 (15)	0.94421 (12)	1.37283 (8)	0.0204 (2)
C16	0.15683 (16)	1.00021 (12)	1.27902 (9)	0.0232 (2)
H16	0.1550	0.9430	1.2317	0.028*
C17	0.09340 (17)	1.14485 (13)	1.25670 (9)	0.0265 (3)
H17	0.0477	1.1861	1.1927	0.032*
C18	0.09507 (18)	1.23038 (13)	1.32516 (10)	0.0285 (3)
H18	0.0522	1.3283	1.3072	0.034*
C19	0.15933 (17)	1.17260 (13)	1.41961 (9)	0.0262 (3)
H19	0.1609	1.2298	1.4670	0.031*
C20	0.35533 (17)	0.68910 (12)	1.35580 (9)	0.0233 (2)
H20A	0.4907	0.6454	1.3637	0.028*
H20B	0.3452	0.7277	1.2827	0.028*
C21	0.23180 (18)	0.57728 (12)	1.39112 (9)	0.0264 (3)
H21A	0.2874	0.4972	1.3572	0.032*
H21B	0.2345	0.5436	1.4653	0.032*
C22	0.03284 (19)	0.62732 (13)	1.36936 (9)	0.0283 (3)
N1	0.38031 (13)	0.78390 (9)	0.94098 (7)	0.01830 (19)
N2	0.09333 (16)	1.14251 (11)	0.99259 (9)	0.0312 (2)
N3	0.30023 (14)	0.80320 (10)	1.41232 (7)	0.0216 (2)
N4	−0.12343 (17)	0.66540 (14)	1.35365 (10)	0.0410 (3)
O1	0.37857 (12)	0.82987 (8)	1.10106 (6)	0.02410 (18)
O2	0.23689 (12)	0.56414 (9)	1.16318 (6)	0.02605 (19)
O3	0.33463 (13)	0.96621 (9)	1.61077 (6)	0.0300 (2)
O4	0.43958 (13)	0.68559 (9)	1.55714 (6)	0.0300 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0187 (5)	0.0186 (5)	0.0195 (5)	−0.0013 (4)	−0.0037 (4)	−0.0046 (4)
C2	0.0190 (5)	0.0186 (5)	0.0202 (5)	−0.0023 (4)	−0.0033 (4)	−0.0042 (4)
C3	0.0168 (5)	0.0180 (5)	0.0191 (5)	−0.0017 (4)	−0.0027 (4)	−0.0038 (4)
C4	0.0159 (5)	0.0152 (5)	0.0207 (5)	−0.0010 (4)	−0.0035 (4)	−0.0052 (4)
C5	0.0221 (5)	0.0176 (5)	0.0187 (5)	−0.0024 (4)	−0.0028 (4)	−0.0037 (4)
C6	0.0239 (5)	0.0209 (5)	0.0202 (5)	−0.0003 (4)	−0.0054 (4)	−0.0079 (4)
C7	0.0230 (5)	0.0171 (5)	0.0278 (6)	−0.0029 (4)	−0.0061 (4)	−0.0081 (4)
C8	0.0194 (5)	0.0167 (5)	0.0238 (5)	−0.0030 (4)	−0.0027 (4)	−0.0033 (4)
C9	0.0238 (5)	0.0188 (5)	0.0221 (5)	−0.0083 (4)	0.0004 (4)	−0.0052 (4)
C10	0.0350 (6)	0.0189 (5)	0.0230 (6)	−0.0065 (5)	−0.0061 (5)	−0.0029 (4)
C11	0.0257 (6)	0.0150 (5)	0.0318 (6)	−0.0062 (4)	−0.0057 (5)	−0.0011 (5)
C12	0.0247 (6)	0.0265 (6)	0.0187 (5)	−0.0073 (4)	0.0000 (4)	−0.0044 (4)
C13	0.0240 (6)	0.0278 (6)	0.0195 (5)	−0.0086 (4)	0.0007 (4)	−0.0064 (4)
C14	0.0207 (5)	0.0262 (6)	0.0205 (5)	−0.0072 (4)	0.0005 (4)	−0.0065 (4)
C15	0.0173 (5)	0.0233 (5)	0.0210 (5)	−0.0057 (4)	0.0011 (4)	−0.0053 (4)
C16	0.0199 (5)	0.0300 (6)	0.0204 (5)	−0.0040 (4)	−0.0014 (4)	−0.0072 (4)
C17	0.0213 (6)	0.0315 (6)	0.0242 (6)	−0.0020 (5)	−0.0034 (4)	−0.0024 (5)
C18	0.0253 (6)	0.0238 (6)	0.0347 (7)	−0.0011 (5)	−0.0042 (5)	−0.0049 (5)
C19	0.0247 (6)	0.0264 (6)	0.0293 (6)	−0.0054 (4)	−0.0007 (5)	−0.0103 (5)
C20	0.0259 (6)	0.0241 (6)	0.0208 (5)	−0.0034 (4)	−0.0011 (4)	−0.0083 (4)
C21	0.0359 (7)	0.0226 (6)	0.0217 (6)	−0.0065 (5)	−0.0048 (5)	−0.0042 (4)
C22	0.0360 (7)	0.0307 (6)	0.0232 (6)	−0.0137 (5)	0.0018 (5)	−0.0117 (5)
N1	0.0218 (4)	0.0158 (4)	0.0187 (4)	−0.0050 (3)	−0.0024 (3)	−0.0048 (3)
N2	0.0303 (5)	0.0220 (5)	0.0406 (6)	−0.0057 (4)	0.0009 (5)	−0.0070 (5)
N3	0.0259 (5)	0.0222 (5)	0.0178 (4)	−0.0052 (4)	−0.0020 (4)	−0.0056 (4)
N4	0.0322 (7)	0.0549 (8)	0.0445 (7)	−0.0133 (5)	−0.0001 (5)	−0.0254 (6)
O1	0.0306 (4)	0.0231 (4)	0.0219 (4)	−0.0061 (3)	−0.0050 (3)	−0.0089 (3)
O2	0.0318 (4)	0.0277 (4)	0.0181 (4)	−0.0077 (3)	−0.0017 (3)	−0.0019 (3)
O3	0.0380 (5)	0.0351 (5)	0.0205 (4)	−0.0101 (4)	−0.0033 (4)	−0.0095 (4)
O4	0.0379 (5)	0.0287 (4)	0.0216 (4)	−0.0030 (4)	−0.0056 (4)	−0.0026 (3)

C1—O1	1.2153 (14)	C12—O4	1.2137 (15)
C1—N1	1.3612 (14)	C12—N3	1.3655 (15)
C1—C2	1.5610 (15)	C12—C13	1.5581 (16)
C2—O2	1.2079 (14)	C13—O3	1.2120 (15)
C2—C3	1.4633 (15)	C13—C14	1.4591 (17)
C3—C8	1.3886 (15)	C14—C19	1.3898 (17)
C3—C4	1.4000 (15)	C14—C15	1.4035 (16)
C4—C5	1.3812 (15)	C15—C16	1.3811 (16)
C4—N1	1.4163 (13)	C15—N3	1.4184 (15)
C5—C6	1.3990 (15)	C16—C17	1.3997 (17)
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.3910 (16)	C17—C18	1.3935 (18)
C6—H6	0.9500	C17—H17	0.9500
C7—C8	1.3919 (16)	C18—C19	1.3880 (18)
C7—H7	0.9500	C18—H18	0.9500
C8—H8	0.9500	C19—H19	0.9500
C9—N1	1.4533 (14)	C20—N3	1.4627 (14)
C9—C10	1.5311 (16)	C20—C21	1.5277 (16)
C9—H9A	0.9900	C20—H20A	0.9900
C9—H9B	0.9900	C20—H20B	0.9900
C10—C11	1.4686 (17)	C21—C22	1.4638 (19)
C10—H10A	0.9900	C21—H21A	0.9900
C10—H10B	0.9900	C21—H21B	0.9900
C11—N2	1.1465 (17)	C22—N4	1.1437 (18)
O1—C1—N1	127.39 (10)	O3—C13—C14	131.27 (11)
O1—C1—C2	126.58 (10)	O3—C13—C12	123.77 (11)
N1—C1—C2	106.03 (9)	C14—C13—C12	104.90 (9)
O2—C2—C3	131.42 (10)	C19—C14—C15	121.09 (11)
O2—C2—C1	123.65 (10)	C19—C14—C13	131.24 (11)
C3—C2—C1	104.94 (9)	C15—C14—C13	107.57 (10)
C8—C3—C4	120.97 (10)	C16—C15—C14	121.14 (11)
C8—C3—C2	131.70 (10)	C16—C15—N3	128.32 (10)
C4—C3—C2	107.33 (9)	C14—C15—N3	110.52 (10)
C5—C4—C3	121.79 (10)	C15—C16—C17	117.12 (11)
C5—C4—N1	127.51 (10)	C15—C16—H16	121.4
C3—C4—N1	110.69 (9)	C17—C16—H16	121.4
C4—C5—C6	116.62 (10)	C18—C17—C16	122.25 (11)
C4—C5—H5	121.7	C18—C17—H17	118.9
C6—C5—H5	121.7	C16—C17—H17	118.9
C7—C6—C5	122.30 (10)	C19—C18—C17	120.05 (11)
C7—C6—H6	118.9	C19—C18—H18	120.0
C5—C6—H6	118.9	C17—C18—H18	120.0
C6—C7—C8	120.37 (10)	C18—C19—C14	118.32 (11)
C6—C7—H7	119.8	C18—C19—H19	120.8
C8—C7—H7	119.8	C14—C19—H19	120.8
C3—C8—C7	117.95 (10)	N3—C20—C21	112.93 (9)
C3—C8—H8	121.0	N3—C20—H20A	109.0
C7—C8—H8	121.0	C21—C20—H20A	109.0
N1—C9—C10	113.21 (9)	N3—C20—H20B	109.0
N1—C9—H9A	108.9	C21—C20—H20B	109.0
C10—C9—H9A	108.9	H20A—C20—H20B	107.8
N1—C9—H9B	108.9	C22—C21—C20	113.17 (10)
C10—C9—H9B	108.9	C22—C21—H21A	108.9
H9A—C9—H9B	107.7	C20—C21—H21A	108.9
C11—C10—C9	112.92 (10)	C22—C21—H21B	108.9
C11—C10—H10A	109.0	C20—C21—H21B	108.9
C9—C10—H10A	109.0	H21A—C21—H21B	107.8
C11—C10—H10B	109.0	N4—C22—C21	179.04 (15)
C9—C10—H10B	109.0	C1—N1—C4	111.00 (9)
H10A—C10—H10B	107.8	C1—N1—C9	124.54 (9)
N2—C11—C10	179.16 (13)	C4—N1—C9	124.46 (9)
O4—C12—N3	126.70 (11)	C12—N3—C15	110.66 (9)
O4—C12—C13	127.01 (10)	C12—N3—C20	121.49 (10)
N3—C12—C13	106.28 (10)	C15—N3—C20	126.46 (9)
O1—C1—C2—O2	1.10 (18)	C19—C14—C15—N3	177.06 (10)
N1—C1—C2—O2	−179.24 (10)	C13—C14—C15—N3	0.37 (13)
O1—C1—C2—C3	−178.80 (11)	C14—C15—C16—C17	1.18 (16)
N1—C1—C2—C3	0.85 (11)	N3—C15—C16—C17	−177.39 (11)
O2—C2—C3—C8	−0.7 (2)	C15—C16—C17—C18	0.00 (17)
C1—C2—C3—C8	179.16 (11)	C16—C17—C18—C19	−0.66 (19)
O2—C2—C3—C4	179.23 (12)	C17—C18—C19—C14	0.14 (18)
C1—C2—C3—C4	−0.87 (11)	C15—C14—C19—C18	1.04 (18)
C8—C3—C4—C5	−0.18 (16)	C13—C14—C19—C18	176.84 (12)
C2—C3—C4—C5	179.85 (10)	N3—C20—C21—C22	66.72 (13)
C8—C3—C4—N1	−179.42 (9)	O1—C1—N1—C4	179.14 (11)
C2—C3—C4—N1	0.61 (12)	C2—C1—N1—C4	−0.51 (11)
C3—C4—C5—C6	0.55 (16)	O1—C1—N1—C9	−0.68 (18)
N1—C4—C5—C6	179.66 (10)	C2—C1—N1—C9	179.67 (9)
C4—C5—C6—C7	−0.27 (16)	C5—C4—N1—C1	−179.22 (10)
C5—C6—C7—C8	−0.40 (17)	C3—C4—N1—C1	−0.04 (12)
C4—C3—C8—C7	−0.50 (16)	C5—C4—N1—C9	0.60 (17)
C2—C3—C8—C7	179.47 (11)	C3—C4—N1—C9	179.78 (9)
C6—C7—C8—C3	0.77 (16)	C10—C9—N1—C1	−93.32 (12)
N1—C9—C10—C11	69.07 (12)	C10—C9—N1—C4	86.88 (12)
O4—C12—C13—O3	−1.59 (19)	O4—C12—N3—C15	−175.78 (11)
N3—C12—C13—O3	179.97 (11)	C13—C12—N3—C15	2.67 (12)
O4—C12—C13—C14	176.08 (12)	O4—C12—N3—C20	−8.40 (18)
N3—C12—C13—C14	−2.37 (12)	C13—C12—N3—C20	170.05 (9)
O3—C13—C14—C19	2.4 (2)	C16—C15—N3—C12	176.66 (11)
C12—C13—C14—C19	−175.05 (12)	C14—C15—N3—C12	−2.04 (13)
O3—C13—C14—C15	178.60 (12)	C16—C15—N3—C20	10.05 (19)
C12—C13—C14—C15	1.18 (12)	C14—C15—N3—C20	−168.64 (10)
C19—C14—C15—C16	−1.74 (17)	C21—C20—N3—C12	80.57 (13)
C13—C14—C15—C16	−178.43 (10)	C21—C20—N3—C15	−114.16 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1	0.95	2.50	3.2787 (14)	139
C20—H20B···O1	0.99	2.45	3.4287 (14)	170
C6—H6···O4i	0.95	2.51	3.1740 (14)	127
C5—H5···O3i	0.95	2.63	3.5085 (14)	153
C9—H9B···O1ii	0.99	2.49	3.2269 (13)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O1	0.95	2.50	3.2787 (14)	139
C20—H20B⋯O1	0.99	2.45	3.4287 (14)	170
C6—H6⋯O4i	0.95	2.51	3.1740 (14)	127
C5—H5⋯O3i	0.95	2.63	3.5085 (14)	153
C9—H9B⋯O1ii	0.99	2.49	3.2269 (13)	131

Symmetry codes: (i) ; (ii) .