2-(1,3-Dioxoisoindolin-2-yl)acetonitrile.

The asymmetric unit of the title compound, C(10)H(6)N(2)O(2), contains two independent mol-ecules. The dihedral angles between the acetonitrile and the 1H-isoindole-1,3(2H)-dione units are 69.0 (7)° and 77.0 (5)° in the two mol-ecules. One of the two terminal N atoms is disordered over two positions in a 0.66 (8):0,34 (8) ratio. In the crystal structure, the mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds.

Related literature

The title compound was prepared as a key intermediate for the synthesis of a new new tetrazolic derivative. For the use of tetra­zoles as pesticides, see: Schocken et al. (1989 ▶); Yanagi et al. (2001 ▶); Lim et al. (2007 ▶) and as anti­hypertensive, anti­alergic, anti­biotic and anti­convulsant agents, see: Hashimoto et al. (1998 ▶); Berghmans et al. (2007 ▶). For their use in cancer, AIDS and obesity treatments, see: Tamura et al. (1998 ▶); Shih et al. (1999 ▶); Muraglia et al. (2006 ▶). A major advantage of tetra­zoles over carb­oxy­lic acids is that they are resistant to many biological metabolic degradation pathways, see: Singh et al. (1980 ▶).

Experimental

Crystal data

C10H6N2O2

M = 186.17

Triclinic,

a = 8.0960 (2) Å

b = 8.4371 (2) Å

c = 14.3118 (3) Å

α = 85.072 (1)°

β = 79.272 (1)°

γ = 68.421 (1)°

V = 893.02 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.25 × 0.24 × 0.16 mm

Data collection

Bruker APEXII CCD detector diffractometer

18332 measured reflections

3906 independent reflections

2885 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.128

S = 1.05

3906 reflections

267 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810037335/jh2206sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037335/jh2206Isup2.hkl

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

Enhanced figure: interactive version of Fig. 3

C10H6N2O2	Z = 4
Mr = 186.17	F(000) = 384
Triclinic, P1	Dx = 1.385 Mg m−3
Hall symbol: -P 1	Melting point: 395 K
a = 8.0960 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4371 (2) Å	Cell parameters from 2714 reflections
c = 14.3118 (3) Å	θ = 2.7–25.3°
α = 85.072 (1)°	µ = 0.10 mm−1
β = 79.272 (1)°	T = 296 K
γ = 68.421 (1)°	Block, colourless
V = 893.02 (4) Å3	0.25 × 0.24 × 0.16 mm

Bruker APEXII CCD detector diffractometer	2885 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
graphite	θmax = 27.0°, θmin = 1.5°
ω and φ scans	h = −10→10
18332 measured reflections	k = −10→10
3906 independent reflections	l = −17→18

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0697P)2 + 0.070P] where P = (Fo2 + 2Fc2)/3
3906 reflections	(Δ/σ)max = 0.005
267 parameters	Δρmax = 0.19 e Å−3
6 restraints	Δρmin = −0.19 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	Occ. (<1)
C11	0.73565 (18)	0.39842 (17)	0.04371 (10)	0.0471 (3)
C16	0.75085 (18)	0.49910 (17)	−0.03635 (10)	0.0461 (3)
C10	0.7395 (2)	0.48752 (18)	0.12747 (11)	0.0497 (3)
C17	0.7711 (2)	0.65409 (18)	−0.00671 (11)	0.0527 (4)
C18	0.7772 (2)	0.76260 (19)	0.15037 (12)	0.0582 (4)
H18A	0.8360	0.8327	0.1112	0.070*
H18B	0.8503	0.7049	0.1984	0.070*
C15	0.7474 (2)	0.4505 (2)	−0.12523 (12)	0.0612 (4)
H15	0.7559	0.5195	−0.1788	0.073*
C14	0.7309 (2)	0.2948 (2)	−0.13128 (13)	0.0685 (5)
H14	0.7291	0.2577	−0.1903	0.082*
C19	0.5995 (3)	0.8711 (2)	0.19668 (15)	0.0745 (5)
C12	0.7182 (3)	0.2438 (2)	0.03696 (14)	0.0670 (5)
H12	0.7075	0.1754	0.0906	0.080*
C13	0.7170 (3)	0.1937 (2)	−0.05234 (15)	0.0750 (5)
H13	0.7065	0.0893	−0.0589	0.090*
C20	0.91639 (18)	0.46404 (18)	0.38170 (10)	0.0462 (3)
C26	0.72827 (18)	0.4498 (2)	0.52338 (10)	0.0495 (3)
C21	0.78905 (18)	0.56105 (19)	0.46334 (10)	0.0472 (3)
C27	0.81143 (19)	0.2782 (2)	0.48113 (11)	0.0512 (4)
C28	1.0390 (2)	0.1584 (2)	0.33559 (12)	0.0598 (4)
H28A	1.1202	0.0741	0.3727	0.072*
H28B	1.1114	0.2015	0.2857	0.072*
C22	0.7336 (2)	0.7317 (2)	0.48390 (12)	0.0600 (4)
H22	0.7740	0.8068	0.4433	0.072*
C29	0.9423 (2)	0.0764 (2)	0.29222 (14)	0.0661 (5)
C23	0.6146 (2)	0.7856 (2)	0.56814 (14)	0.0715 (5)
H23	0.5744	0.8996	0.5843	0.086*
C25	0.6098 (2)	0.5045 (3)	0.60702 (12)	0.0640 (4)
H25	0.5686	0.4297	0.6475	0.077*
C24	0.5549 (2)	0.6749 (3)	0.62815 (13)	0.0725 (5)
H24	0.4758	0.7154	0.6842	0.087*
O11	0.72249 (19)	0.44907 (16)	0.21083 (8)	0.0739 (4)
O12	0.7926 (2)	0.77161 (16)	−0.05386 (10)	0.0863 (4)
O20	1.00395 (15)	0.51155 (14)	0.31593 (8)	0.0613 (3)
O21	0.79522 (16)	0.14499 (15)	0.50949 (9)	0.0727 (4)
N11	0.76467 (16)	0.63694 (14)	0.09160 (9)	0.0497 (3)
N21	0.92041 (16)	0.29721 (15)	0.39635 (8)	0.0494 (3)
N22	0.8731 (3)	0.0080 (2)	0.25846 (16)	0.1020 (7)
N12A	0.4599 (15)	0.972 (4)	0.222 (2)	0.100 (4)	0.66 (8)
N12B	0.466 (4)	0.916 (6)	0.252 (3)	0.085 (6)	0.34 (8)

	U11	U22	U33	U12	U13	U23
C11	0.0471 (8)	0.0391 (7)	0.0555 (8)	−0.0166 (6)	−0.0054 (6)	−0.0037 (6)
C16	0.0411 (7)	0.0434 (7)	0.0506 (8)	−0.0148 (6)	0.0017 (6)	−0.0064 (6)
C10	0.0539 (8)	0.0439 (8)	0.0529 (9)	−0.0215 (6)	−0.0049 (6)	−0.0009 (6)
C17	0.0550 (8)	0.0447 (8)	0.0597 (9)	−0.0227 (7)	−0.0037 (7)	0.0018 (7)
C18	0.0611 (9)	0.0469 (8)	0.0728 (10)	−0.0233 (7)	−0.0141 (8)	−0.0108 (7)
C15	0.0567 (9)	0.0693 (10)	0.0519 (9)	−0.0200 (8)	0.0035 (7)	−0.0102 (8)
C14	0.0631 (10)	0.0669 (11)	0.0705 (11)	−0.0135 (8)	−0.0062 (8)	−0.0307 (9)
C19	0.0700 (12)	0.0728 (12)	0.0872 (14)	−0.0258 (10)	−0.0134 (10)	−0.0353 (10)
C12	0.0875 (12)	0.0422 (8)	0.0784 (12)	−0.0294 (8)	−0.0189 (9)	0.0008 (8)
C13	0.0835 (12)	0.0453 (9)	0.1006 (15)	−0.0209 (9)	−0.0214 (11)	−0.0213 (9)
C20	0.0446 (7)	0.0517 (8)	0.0462 (8)	−0.0201 (6)	−0.0124 (6)	0.0007 (6)
C26	0.0418 (7)	0.0632 (9)	0.0449 (8)	−0.0185 (7)	−0.0123 (6)	0.0011 (7)
C21	0.0432 (7)	0.0540 (8)	0.0462 (8)	−0.0167 (6)	−0.0127 (6)	−0.0035 (6)
C27	0.0455 (8)	0.0578 (9)	0.0532 (8)	−0.0209 (7)	−0.0143 (6)	0.0073 (7)
C28	0.0518 (9)	0.0554 (9)	0.0701 (10)	−0.0151 (7)	−0.0088 (8)	−0.0125 (8)
C22	0.0573 (9)	0.0558 (9)	0.0674 (10)	−0.0164 (7)	−0.0166 (8)	−0.0072 (8)
C29	0.0628 (10)	0.0485 (9)	0.0830 (12)	−0.0116 (8)	−0.0123 (9)	−0.0185 (8)
C23	0.0590 (10)	0.0699 (11)	0.0766 (12)	−0.0041 (8)	−0.0181 (9)	−0.0257 (10)
C25	0.0492 (9)	0.0898 (13)	0.0496 (9)	−0.0219 (8)	−0.0069 (7)	−0.0001 (8)
C24	0.0517 (9)	0.0973 (15)	0.0572 (10)	−0.0114 (9)	−0.0049 (8)	−0.0202 (10)
O11	0.1064 (10)	0.0764 (8)	0.0524 (7)	−0.0494 (8)	−0.0150 (6)	0.0068 (6)
O12	0.1289 (12)	0.0668 (8)	0.0810 (9)	−0.0601 (8)	−0.0181 (8)	0.0195 (7)
O20	0.0651 (7)	0.0686 (7)	0.0530 (6)	−0.0320 (6)	−0.0011 (5)	0.0014 (5)
O21	0.0695 (7)	0.0627 (7)	0.0869 (9)	−0.0291 (6)	−0.0133 (6)	0.0184 (6)
N11	0.0584 (7)	0.0396 (6)	0.0556 (7)	−0.0229 (5)	−0.0072 (6)	−0.0052 (5)
N21	0.0499 (7)	0.0496 (7)	0.0498 (7)	−0.0186 (5)	−0.0072 (5)	−0.0065 (5)
N22	0.0928 (13)	0.0766 (11)	0.1438 (18)	−0.0253 (10)	−0.0265 (12)	−0.0498 (12)
N12A	0.078 (2)	0.098 (7)	0.114 (8)	−0.013 (4)	−0.013 (4)	−0.048 (7)
N12B	0.079 (5)	0.081 (10)	0.088 (10)	−0.020 (6)	0.005 (5)	−0.040 (7)

C11—C12	1.376 (2)	C20—N21	1.3944 (18)
C11—C16	1.381 (2)	C20—C21	1.481 (2)
C11—C10	1.480 (2)	C26—C21	1.380 (2)
C16—C15	1.378 (2)	C26—C25	1.381 (2)
C16—C17	1.482 (2)	C26—C27	1.482 (2)
C10—O11	1.2052 (18)	C21—C22	1.382 (2)
C10—N11	1.3903 (18)	C27—O21	1.2066 (17)
C17—O12	1.1989 (18)	C27—N21	1.3958 (19)
C17—N11	1.395 (2)	C28—N21	1.4445 (19)
C18—N11	1.4511 (18)	C28—C29	1.460 (2)
C18—C19	1.458 (2)	C28—H28A	0.9700
C18—H18A	0.9700	C28—H28B	0.9700
C18—H18B	0.9700	C22—C23	1.388 (2)
C15—C14	1.380 (2)	C22—H22	0.9300
C15—H15	0.9300	C29—N22	1.125 (2)
C14—C13	1.369 (3)	C23—C24	1.372 (3)
C14—H14	0.9300	C23—H23	0.9300
C12—C13	1.383 (3)	C25—C24	1.383 (3)
C12—H12	0.9300	C25—H25	0.9300
C13—H13	0.9300	C24—H24	0.9300
C20—O20	1.2021 (17)
C12—C11—C16	120.65 (14)	C21—C26—C27	108.31 (13)
C12—C11—C10	130.71 (15)	C25—C26—C27	130.42 (15)
C16—C11—C10	108.64 (12)	C26—C21—C22	121.60 (14)
C15—C16—C11	121.80 (13)	C26—C21—C20	108.40 (13)
C15—C16—C17	130.20 (14)	C22—C21—C20	129.99 (14)
C11—C16—C17	108.00 (13)	O21—C27—N21	124.00 (15)
O11—C10—N11	123.96 (14)	O21—C27—C26	130.39 (15)
O11—C10—C11	130.57 (14)	N21—C27—C26	105.61 (12)
N11—C10—C11	105.46 (12)	N21—C28—C29	112.91 (13)
O12—C17—N11	124.60 (15)	N21—C28—H28A	109.0
O12—C17—C16	129.75 (15)	C29—C28—H28A	109.0
N11—C17—C16	105.63 (12)	N21—C28—H28B	109.0
N11—C18—C19	111.30 (13)	C29—C28—H28B	109.0
N11—C18—H18A	109.4	H28A—C28—H28B	107.8
C19—C18—H18A	109.4	C21—C22—C23	116.75 (17)
N11—C18—H18B	109.4	C21—C22—H22	121.6
C19—C18—H18B	109.4	C23—C22—H22	121.6
H18A—C18—H18B	108.0	N22—C29—C28	177.51 (18)
C16—C15—C14	117.07 (16)	C24—C23—C22	121.71 (17)
C16—C15—H15	121.5	C24—C23—H23	119.1
C14—C15—H15	121.5	C22—C23—H23	119.1
C13—C14—C15	121.47 (16)	C26—C25—C24	117.30 (17)
C13—C14—H14	119.3	C26—C25—H25	121.4
C15—C14—H14	119.3	C24—C25—H25	121.4
C11—C12—C13	117.66 (16)	C23—C24—C25	121.36 (16)
C11—C12—H12	121.2	C23—C24—H24	119.3
C13—C12—H12	121.2	C25—C24—H24	119.3
C14—C13—C12	121.34 (16)	C10—N11—C17	112.21 (12)
C14—C13—H13	119.3	C10—N11—C18	123.66 (13)
C12—C13—H13	119.3	C17—N11—C18	124.11 (12)
O20—C20—N21	124.84 (14)	C20—N21—C27	112.00 (12)
O20—C20—C21	129.50 (14)	C20—N21—C28	123.18 (12)
N21—C20—C21	105.65 (12)	C27—N21—C28	124.49 (13)
C21—C26—C25	121.28 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O12i	0.93	2.51	3.386 (2)	158
C15—H15···O20ii	0.93	2.45	3.144 (2)	132
C18—H18B···O20	0.97	2.42	3.372 (2)	167
C28—H28A···O21iii	0.97	2.39	3.298 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O12i	0.93	2.51	3.386 (2)	158
C15—H15⋯O20ii	0.93	2.45	3.144 (2)	132
C18—H18B⋯O20	0.97	2.42	3.372 (2)	167
C28—H28A⋯O21iii	0.97	2.39	3.298 (2)	156

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