1-(Prop-2-yn-yl)indoline-2,3-dione.

The structure of the title compound, C11H7NO2, is isotypic to that of its homologue, 1-octylindoline-2,3-dione [Qachchachi et al. (2013 ▶). Acta Cryst. E69, o1801]. The indoline ring and the two carbonyl O atoms are approximately coplanar, the largest deviation from the mean plane being 0.021 (1) Å for one of the O atoms. The mean plane through the fused ring system is nearly perpendicular to the propynyl group, as indicated by the N-C-C-C torsion angle of 77.9 (1)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds and π-π inter-actions between benzene rings [inter-centroid distance = 3.5630 (10) Å], forming a three-dimensional structure.

Related literature

For the biological activity of indoline derivatives, see: Malhotra et al. (2011 ▶); Ramachandran (2011 ▶); Smitha et al. (2008 ▶). For the structure of 1-octylindoline-2,3-dione, see: Qachchachi et al. (2013 ▶).

Experimental

Crystal data

C11H7NO2

M = 185.18

Triclinic,

a = 7.0939 (7) Å

b = 7.9452 (7) Å

c = 8.5658 (6) Å

α = 80.464 (7)°

β = 85.760 (7)°

γ = 63.881 (9)°

V = 427.50 (6) Å3

Z = 2

Cu Kα radiation

μ = 0.83 mm−1

T = 123 K

0.15 × 0.13 × 0.02 mm

Data collection

Agilent SuperNova (Single source at offset, Atlas) diffractometer

Absorption correction: analytical (Clark & Reid, 1995 ▶) T min = 0.910, T max = 0.981

3081 measured reflections

1627 independent reflections

1438 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.094

S = 1.07

1627 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.22 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/S1600536814003973/tk5296sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003973/tk5296Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003973/tk5296Isup3.cml

CCDC reference:

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

C11H7NO2	Z = 2
Mr = 185.18	F(000) = 192
Triclinic, P1	Dx = 1.439 Mg m−3
Hall symbol: -P 1	Melting point: 423 K
a = 7.0939 (7) Å	Cu Kα radiation, λ = 1.54184 Å
b = 7.9452 (7) Å	Cell parameters from 1851 reflections
c = 8.5658 (6) Å	θ = 5.2–73.3°
α = 80.464 (7)°	µ = 0.83 mm−1
β = 85.760 (7)°	T = 123 K
γ = 63.881 (9)°	Plate, red
V = 427.50 (6) Å3	0.15 × 0.13 × 0.02 mm

Agilent SuperNova (Single source at offset, Atlas) diffractometer	1627 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1438 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 10.3546 pixels mm-1	θmax = 73.5°, θmin = 5.2°
ω scans	h = −8→8
Absorption correction: analytical (Clark & Reid, 1995)	k = −9→9
Tmin = 0.910, Tmax = 0.981	l = −7→10
3081 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0429P)2 + 0.0993P] where P = (Fo2 + 2Fc2)/3
1627 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.22 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 > 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	0.25017 (19)	0.06257 (19)	0.05480 (16)	0.0180 (3)
C2	0.1753 (2)	0.2210 (2)	−0.05932 (17)	0.0211 (3)
H2	0.1510	0.3421	−0.0368	0.025*
C3	0.1367 (2)	0.1959 (2)	−0.20994 (16)	0.0225 (3)
H3	0.0847	0.3028	−0.2906	0.027*
C4	0.1719 (2)	0.0202 (2)	−0.24516 (16)	0.0224 (3)
H4	0.1440	0.0084	−0.3486	0.027*
C5	0.2481 (2)	−0.1391 (2)	−0.12896 (16)	0.0204 (3)
H5	0.2729	−0.2602	−0.1517	0.025*
C6	0.2867 (2)	−0.11607 (19)	0.02066 (16)	0.0186 (3)
C7	0.3621 (2)	−0.25174 (19)	0.16566 (16)	0.0201 (3)
C8	0.3703 (2)	−0.1326 (2)	0.29023 (16)	0.0204 (3)
C9	0.2676 (2)	0.2094 (2)	0.29379 (16)	0.0222 (3)
H9A	0.2986	0.3039	0.2198	0.027*
H9B	0.3644	0.1648	0.3849	0.027*
C10	0.0499 (2)	0.29983 (19)	0.34996 (16)	0.0210 (3)
C11	−0.1255 (2)	0.3711 (2)	0.39699 (17)	0.0249 (3)
H11	−0.2657	0.4280	0.4346	0.030*
N1	0.30354 (18)	0.04896 (16)	0.21361 (13)	0.0203 (3)
O1	0.40885 (16)	−0.41925 (14)	0.19499 (12)	0.0263 (3)
O2	0.42444 (16)	−0.19092 (15)	0.42712 (12)	0.0262 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0119 (6)	0.0223 (6)	0.0210 (6)	−0.0082 (5)	0.0020 (5)	−0.0050 (5)
C2	0.0172 (6)	0.0193 (6)	0.0270 (7)	−0.0082 (5)	0.0014 (5)	−0.0040 (5)
C3	0.0177 (6)	0.0251 (7)	0.0230 (7)	−0.0093 (5)	0.0003 (5)	0.0010 (5)
C4	0.0196 (7)	0.0296 (7)	0.0192 (6)	−0.0116 (6)	0.0015 (5)	−0.0050 (5)
C5	0.0161 (6)	0.0230 (7)	0.0230 (6)	−0.0085 (5)	0.0023 (5)	−0.0066 (5)
C6	0.0143 (6)	0.0196 (6)	0.0218 (6)	−0.0073 (5)	0.0015 (5)	−0.0039 (5)
C7	0.0142 (6)	0.0222 (7)	0.0229 (6)	−0.0073 (5)	0.0008 (5)	−0.0033 (5)
C8	0.0150 (6)	0.0247 (7)	0.0223 (7)	−0.0096 (5)	0.0014 (5)	−0.0031 (5)
C9	0.0219 (7)	0.0248 (7)	0.0240 (7)	−0.0120 (6)	−0.0005 (5)	−0.0089 (5)
C10	0.0260 (7)	0.0204 (6)	0.0193 (6)	−0.0117 (6)	−0.0025 (5)	−0.0042 (5)
C11	0.0240 (7)	0.0240 (7)	0.0271 (7)	−0.0103 (6)	0.0003 (6)	−0.0057 (5)
N1	0.0196 (6)	0.0213 (6)	0.0204 (6)	−0.0085 (5)	−0.0003 (4)	−0.0051 (4)
O1	0.0261 (5)	0.0193 (5)	0.0307 (5)	−0.0079 (4)	−0.0018 (4)	−0.0012 (4)
O2	0.0266 (5)	0.0343 (6)	0.0197 (5)	−0.0153 (5)	−0.0027 (4)	−0.0016 (4)

C1—C2	1.379 (2)	C6—C7	1.4622 (18)
C1—C6	1.4034 (18)	C7—O1	1.2072 (17)
C1—N1	1.4131 (17)	C7—C8	1.5589 (18)
C2—C3	1.402 (2)	C8—O2	1.2111 (18)
C2—H2	0.9500	C8—N1	1.3663 (18)
C3—C4	1.387 (2)	C9—N1	1.4631 (17)
C3—H3	0.9500	C9—C10	1.470 (2)
C4—C5	1.394 (2)	C9—H9A	0.9900
C4—H4	0.9500	C9—H9B	0.9900
C5—C6	1.3872 (19)	C10—C11	1.188 (2)
C5—H5	0.9500	C11—H11	0.9500
C2—C1—C6	121.15 (12)	O1—C7—C6	131.72 (13)
C2—C1—N1	128.42 (13)	O1—C7—C8	123.44 (12)
C6—C1—N1	110.42 (12)	C6—C7—C8	104.83 (11)
C1—C2—C3	117.21 (13)	O2—C8—N1	127.55 (13)
C1—C2—H2	121.4	O2—C8—C7	126.40 (13)
C3—C2—H2	121.4	N1—C8—C7	106.05 (11)
C4—C3—C2	122.21 (13)	N1—C9—C10	111.50 (11)
C4—C3—H3	118.9	N1—C9—H9A	109.3
C2—C3—H3	118.9	C10—C9—H9A	109.3
C3—C4—C5	120.08 (12)	N1—C9—H9B	109.3
C3—C4—H4	120.0	C10—C9—H9B	109.3
C5—C4—H4	120.0	H9A—C9—H9B	108.0
C6—C5—C4	118.27 (13)	C11—C10—C9	179.14 (16)
C6—C5—H5	120.9	C10—C11—H11	180.0
C4—C5—H5	120.9	C8—N1—C1	111.08 (11)
C5—C6—C1	121.08 (13)	C8—N1—C9	123.22 (12)
C5—C6—C7	131.32 (13)	C1—N1—C9	125.25 (12)
C1—C6—C7	107.60 (11)
C6—C1—C2—C3	0.27 (19)	O1—C7—C8—O2	0.7 (2)
N1—C1—C2—C3	179.20 (13)	C6—C7—C8—O2	179.86 (13)
C1—C2—C3—C4	−0.2 (2)	O1—C7—C8—N1	−179.02 (13)
C2—C3—C4—C5	0.0 (2)	C6—C7—C8—N1	0.16 (14)
C3—C4—C5—C6	0.04 (19)	O2—C8—N1—C1	−178.89 (13)
C4—C5—C6—C1	0.04 (19)	C7—C8—N1—C1	0.81 (14)
C4—C5—C6—C7	178.89 (13)	O2—C8—N1—C9	−6.2 (2)
C2—C1—C6—C5	−0.20 (19)	C7—C8—N1—C9	173.50 (11)
N1—C1—C6—C5	−179.30 (12)	C2—C1—N1—C8	179.43 (13)
C2—C1—C6—C7	−179.30 (12)	C6—C1—N1—C8	−1.55 (16)
N1—C1—C6—C7	1.60 (15)	C2—C1—N1—C9	6.9 (2)
C5—C6—C7—O1	−0.9 (3)	C6—C1—N1—C9	−174.06 (12)
C1—C6—C7—O1	178.03 (14)	C10—C9—N1—C8	−90.49 (15)
C5—C6—C7—C8	179.97 (14)	C10—C9—N1—C1	81.16 (16)
C1—C6—C7—C8	−1.05 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1i	0.95	2.62	3.3901 (17)	139
C9—H9A···O1ii	0.99	2.61	3.4747 (18)	146
C9—H9B···O2iii	0.99	2.37	3.2987 (17)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.95	2.62	3.3901 (17)	139
C9—H9A⋯O1ii	0.99	2.61	3.4747 (18)	146
C9—H9B⋯O2iii	0.99	2.37	3.2987 (17)	156

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