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

Li, X.-J.; Xiong, M.-H.; Xia, C.-C.

doi:10.1107/S1600536807064185

organic compounds

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Volume 64| Part 1| January 2008| Page o182

https://doi.org/10.1107/S1600536807064185

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

Xiao-Jun Li,^a Ming-Hui Xiong ^a and Cheng-Cai Xia ^b ^*

^aXinyu College, Xinyu 338000, People's Republic of China, and ^bDepartment of Pharmaceutical Science, Taishan Medical College, Taian, 271000, People's Republic of China
^*Correspondence e-mail: xiachc@163.com

(Received 27 November 2007; accepted 28 November 2007; online 6 December 2007)

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

Related literature

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

Experimental

Crystal data

C₁₁H₈N₂O₂
M_r = 200.19
Monoclinic, P 2₁ /c
a = 9.1368 (17) Å
b = 8.2543 (16) Å
c = 12.646 (2) Å
β = 96.909 (3)°
V = 946.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 (2) K
0.17 × 0.15 × 0.12 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: none
4828 measured reflections
1674 independent reflections
1494 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.124
S = 1.00
1674 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯N1ⁱ	0.93	2.62	3.517 (2)	162
C8—H8⋯O2ⁱⁱ	0.93	2.55	3.3922 (17)	151
C2—H2A⋯O1ⁱⁱⁱ	0.97	2.58	3.3682 (17)	138
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807064185/hb2669sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064185/hb2669Isup2.hkl

checkCIF report

Comment top

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 top

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

Experimental top

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.

Structure description top

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).

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

Computing details top

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 top

	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 top

Crystal data top

C₁₁H₈N₂O₂	F(000) = 416
M_r = 200.19	D_x = 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) Å³	0.17 × 0.15 × 0.12 mm
Z = 4

Data collection top

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

Refinement top

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)] = 0.030	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.1P)² + 0.04P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.002
1674 reflections	Δρ_max = 0.13 e Å⁻³
137 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.104 (13)

Crystal data top

C₁₁H₈N₂O₂	V = 946.8 (3) Å³
M_r = 200.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.1368 (17) Å	µ = 0.10 mm⁻¹
b = 8.2543 (16) Å	T = 273 K
c = 12.646 (2) Å	0.17 × 0.15 × 0.12 mm
β = 96.909 (3)°

Data collection top

Siemens SMART CCD diffractometer	1494 reflections with I > 2σ(I)
4828 measured reflections	R_int = 0.018
1674 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.00	Δρ_max = 0.13 e Å⁻³
1674 reflections	Δρ_min = −0.13 e Å⁻³
137 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···N1ⁱ	0.93	2.62	3.517 (2)	162
C8—H8···O2ⁱⁱ	0.93	2.55	3.3922 (17)	151
C2—H2A···O1ⁱⁱⁱ	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.

Experimental details

Crystal data
Chemical formula	C₁₁H₈N₂O₂
M_r	200.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	9.1368 (17), 8.2543 (16), 12.646 (2)
β (°)	96.909 (3)
V (Å³)	946.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.17 × 0.15 × 0.12

Data collection
Diffractometer	Siemens SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4828, 1674, 1494
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.124, 1.00
No. of reflections	1674
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···N1ⁱ	0.93	2.62	3.517 (2)	162
C8—H8···O2ⁱⁱ	0.93	2.55	3.3922 (17)	151
C2—H2A···O1ⁱⁱⁱ	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.

References

Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Wingrove, A. S. & Caret, R. L. (1981). Org. Chem. pp. 11–26. Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o182

https://doi.org/10.1107/S1600536807064185

Open

access