3-(1,3-Dioxoisoindolin-2-yl)propane­nitrile

In the title compound, C₁₁H₈N₂O₂, the packing is consolidated by C—H...N and C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.030
• wR factor = 0.124
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

S1. Comment

Isoindoline-1,3-dione derivatives exhibit a high level of biological activity (Wingrove & Caret, 1981). As a part of our studies in this area, we have isolated the title compound, (I), (Fig. 1).

As expected, the six-membered and five-membered rings are almost co-planar [dihedral angle = 0.67 (6)°]. In the crystal of (I), C—H···O and C—H···N interactions (Table 1) help to establish the packing (Fig. 2).

Related literature

For related literature, see: Wingrove & Caret (1981).

S2. Experimental

Tht title compound was synthesized from a mixture of isoindoline-1,3-dione (5 mmol, 0.736 g) and 3-chloropropanenitrile (5 mmol, 0.448 g) and triethylamine (8 mmol, 0.505 g) and 30 ml N,N-dimethylformamide. The components were dissolved in 20 ml e thanol and 2 ml water, then heated to boiling and stirred for ten minutes. The system was cooled to the room temperature and colourless blocks of (I) were collected after six days.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures

	Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids for the non-hydrogen atoms.
	Fig. 2. Part of the crystal structure of (I), with hydrogen bonds shown as thin lines.

3-(1,3-Dioxoisoindolin-2-yl)propanenitrile

Crystal data

C11H8N2O2	F(000) = 416
Mr = 200.19	Dx = 1.404 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2936 reflections
a = 9.1368 (17) Å	θ = 2.5–28.2°
b = 8.2543 (16) Å	µ = 0.10 mm^−1
c = 12.646 (2) Å	T = 273 K
β = 96.909 (3)°	Block, colorless
V = 946.8 (3) Å^3	0.17 × 0.15 × 0.12 mm
Z = 4

Data collection

Siemens SMART CCD diffractometer	1494 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.018
Graphite monochromator	θmax = 25.0°, θmin = 3.0°
ω scans	h = −10→7
4828 measured reflections	k = −9→9
1674 independent reflections	l = −15→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.04P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.002
1674 reflections	Δρmax = 0.13 e Å^−3
137 parameters	Δρmin = −0.12 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.104 (13)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.31079 (12)	0.24260 (12)	0.97960 (8)	0.0663 (4)
O2	0.56771 (10)	−0.04615 (12)	0.75807 (8)	0.0611 (3)
N1	0.05883 (14)	0.35783 (16)	0.75444 (12)	0.0732 (4)
N2	0.40733 (11)	0.08414 (11)	0.85568 (8)	0.0448 (3)
C1	0.12620 (14)	0.24940 (15)	0.73348 (11)	0.0510 (4)
C2	0.20664 (13)	0.10716 (16)	0.70665 (10)	0.0499 (4)
H2A	0.2848	0.1402	0.6658	0.060*
H2B	0.1405	0.0368	0.6619	0.060*
C3	0.27357 (14)	0.01227 (15)	0.80366 (10)	0.0496 (4)
H3A	0.2020	0.0053	0.8542	0.060*
H3B	0.2947	−0.0971	0.7819	0.060*
C4	0.41465 (14)	0.19575 (15)	0.93856 (9)	0.0469 (4)
C5	0.54539 (14)	0.04830 (14)	0.82728 (9)	0.0450 (3)
C6	0.65174 (14)	0.14708 (13)	0.89805 (9)	0.0456 (3)
C7	0.57276 (14)	0.23633 (14)	0.96403 (9)	0.0464 (4)
C8	0.64206 (17)	0.34173 (15)	1.03802 (10)	0.0586 (4)
H8	0.5890	0.4026	1.0822	0.070*
C9	0.79450 (19)	0.35366 (16)	1.04404 (11)	0.0659 (4)
H9	0.8443	0.4242	1.0932	0.079*
C10	0.87332 (18)	0.26370 (17)	0.97915 (12)	0.0649 (4)
H10	0.9754	0.2735	0.9855	0.078*
C11	0.80229 (15)	0.15797 (16)	0.90385 (11)	0.0573 (4)
H11	0.8549	0.0972	0.8593	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0719 (7)	0.0692 (7)	0.0603 (7)	0.0093 (5)	0.0179 (5)	−0.0101 (5)
O2	0.0645 (6)	0.0646 (6)	0.0544 (6)	0.0029 (4)	0.0073 (5)	−0.0196 (5)
N1	0.0610 (8)	0.0670 (8)	0.0897 (10)	0.0111 (6)	0.0017 (7)	−0.0017 (7)
N2	0.0512 (6)	0.0400 (5)	0.0433 (6)	−0.0014 (4)	0.0058 (4)	−0.0009 (4)
C1	0.0417 (7)	0.0532 (8)	0.0566 (8)	−0.0056 (5)	0.0001 (6)	0.0029 (5)
C2	0.0500 (7)	0.0527 (7)	0.0472 (7)	−0.0050 (5)	0.0060 (5)	−0.0037 (5)
C3	0.0528 (7)	0.0415 (6)	0.0547 (7)	−0.0060 (5)	0.0067 (6)	0.0008 (5)
C4	0.0619 (8)	0.0396 (6)	0.0401 (6)	0.0054 (5)	0.0097 (5)	0.0029 (5)
C5	0.0543 (7)	0.0414 (6)	0.0392 (6)	0.0015 (5)	0.0049 (5)	0.0013 (5)
C6	0.0576 (7)	0.0392 (6)	0.0391 (6)	−0.0003 (5)	0.0017 (5)	0.0047 (5)
C7	0.0635 (8)	0.0375 (6)	0.0366 (6)	0.0025 (5)	−0.0004 (5)	0.0046 (4)
C8	0.0843 (10)	0.0435 (7)	0.0449 (7)	0.0032 (6)	−0.0047 (6)	−0.0015 (5)
C9	0.0839 (10)	0.0508 (8)	0.0565 (8)	−0.0097 (7)	−0.0190 (7)	0.0016 (6)
C10	0.0660 (9)	0.0639 (9)	0.0610 (9)	−0.0114 (6)	−0.0083 (7)	0.0074 (7)
C11	0.0577 (8)	0.0581 (8)	0.0551 (8)	−0.0033 (6)	0.0030 (6)	0.0029 (6)

Geometric parameters (Å, º)

O1—C4	1.1992 (15)	C4—C7	1.4801 (18)
O2—C5	1.2076 (14)	C5—C6	1.4835 (17)
N1—C1	1.1356 (17)	C6—C11	1.3717 (18)
N2—C5	1.3845 (16)	C6—C7	1.3801 (17)
N2—C4	1.3910 (16)	C7—C8	1.3751 (17)
N2—C3	1.4440 (15)	C8—C9	1.389 (2)
C1—C2	1.4469 (18)	C8—H8	0.9300
C2—C3	1.5206 (18)	C9—C10	1.373 (2)
C2—H2A	0.9700	C9—H9	0.9300
C2—H2B	0.9700	C10—C11	1.3932 (19)
C3—H3A	0.9700	C10—H10	0.9300
C3—H3B	0.9700	C11—H11	0.9300
C5—N2—C4	111.98 (10)	O2—C5—C6	129.54 (11)
C5—N2—C3	122.80 (10)	N2—C5—C6	106.09 (10)
C4—N2—C3	125.22 (10)	C11—C6—C7	121.78 (12)
N1—C1—C2	177.64 (14)	C11—C6—C5	130.40 (11)
C1—C2—C3	113.27 (11)	C7—C6—C5	107.82 (11)
C1—C2—H2A	108.9	C8—C7—C6	121.18 (13)
C3—C2—H2A	108.9	C8—C7—C4	130.45 (12)
C1—C2—H2B	108.9	C6—C7—C4	108.37 (11)
C3—C2—H2B	108.9	C7—C8—C9	117.30 (13)
H2A—C2—H2B	107.7	C7—C8—H8	121.3
N2—C3—C2	113.09 (9)	C9—C8—H8	121.3
N2—C3—H3A	109.0	C10—C9—C8	121.56 (13)
C2—C3—H3A	109.0	C10—C9—H9	119.2
N2—C3—H3B	109.0	C8—C9—H9	119.2
C2—C3—H3B	109.0	C9—C10—C11	120.83 (15)
H3A—C3—H3B	107.8	C9—C10—H10	119.6
O1—C4—N2	124.81 (12)	C11—C10—H10	119.6
O1—C4—C7	129.44 (12)	C6—C11—C10	117.34 (13)
N2—C4—C7	105.73 (10)	C6—C11—H11	121.3
O2—C5—N2	124.37 (11)	C10—C11—H11	121.3
C5—N2—C3—C2	−88.43 (14)	C11—C6—C7—C8	0.69 (17)
C4—N2—C3—C2	91.44 (14)	C5—C6—C7—C8	−179.16 (10)
C1—C2—C3—N2	−78.45 (14)	C11—C6—C7—C4	−179.38 (10)
C5—N2—C4—O1	−177.63 (11)	C5—C6—C7—C4	0.77 (12)
C3—N2—C4—O1	2.48 (19)	O1—C4—C7—C8	−2.7 (2)
C5—N2—C4—C7	0.90 (13)	N2—C4—C7—C8	178.90 (11)
C3—N2—C4—C7	−178.99 (10)	O1—C4—C7—C6	177.41 (12)
C4—N2—C5—O2	179.38 (11)	N2—C4—C7—C6	−1.02 (13)
C3—N2—C5—O2	−0.73 (18)	C6—C7—C8—C9	−0.46 (17)
C4—N2—C5—C6	−0.44 (13)	C4—C7—C8—C9	179.63 (12)
C3—N2—C5—C6	179.44 (10)	C7—C8—C9—C10	−0.21 (19)
O2—C5—C6—C11	0.1 (2)	C8—C9—C10—C11	0.7 (2)
N2—C5—C6—C11	179.93 (12)	C7—C6—C11—C10	−0.23 (18)
O2—C5—C6—C7	179.96 (12)	C5—C6—C11—C10	179.59 (12)
N2—C5—C6—C7	−0.23 (12)	C9—C10—C11—C6	−0.43 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···N1^i	0.93	2.62	3.517 (2)	162
C8—H8···O2^ii	0.93	2.55	3.3922 (17)	151
C2—H2A···O1^iii	0.97	2.58	3.3682 (17)	138

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+1/2, z+1/2; (iii) x, −y+1/2, z−1/2.