2,2'-o-Phenyl-enediacetonitrile.

In the title compound, NCCH(2)C(6)H(4)CH(2)CN, the bond lengths and angles are within normal ranges. The benzene ring makes dihedral angles of 4.94 (8) and 77.04 (8)° with the C-C-C-N mean planes. Weak non-conventional C-H⋯N hydrogen bonds are effective in the stabilization of the crystal structure. The weak C-H⋯N contacts form anti-parallel chains running in the a + c direction, and ring systems with two N-atom acceptors and four H-atom donors.

Related literature

For reactions of Woollins’ Reagent see: Gray et al. (2005 ▶); Hua et al. (2006 ▶, 2009 ▶); Hua & Woollins (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H8N2

M = 156.18

Monoclinic,

a = 8.3882 (18) Å

b = 8.1605 (15) Å

c = 11.993 (2) Å

β = 101.890 (6)°

V = 803.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 93 K

0.30 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2004 ▶) T min = 0.977, T max = 0.988

5271 measured reflections

1660 independent reflections

1330 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.133

S = 1.09

1660 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku, 2004 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809041506/si2203sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041506/si2203Isup2.hkl

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

C10H8N2	F(000) = 328
Mr = 156.18	Dx = 1.291 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.3882 (18) Å	Cell parameters from 2633 reflections
b = 8.1605 (15) Å	θ = 2.7–28.3°
c = 11.993 (2) Å	µ = 0.08 mm−1
β = 101.890 (6)°	T = 93 K
V = 803.4 (3) Å3	Block, colorless
Z = 4	0.30 × 0.25 × 0.15 mm

Rigaku Mercury CCD diffractometer	1660 independent reflections
Radiation source: rotating anode	1330 reflections with I > 2σ(I)
confocal	Rint = 0.031
Detector resolution: 0.83 pixels mm-1	θmax = 28.7°, θmin = 2.7°
ω scans	h = −11→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2004)	k = −9→10
Tmin = 0.977, Tmax = 0.988	l = −13→15
5271 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0698P)2 + 0.0077P] where P = (Fo2 + 2Fc2)/3
1660 reflections	(Δ/σ)max = 0.001
109 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.21 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	0.77845 (13)	0.05887 (16)	0.95174 (10)	0.0215 (3)
C2	0.72184 (13)	0.13136 (16)	1.04228 (10)	0.0218 (3)
C7	0.83384 (14)	0.16768 (16)	0.86390 (10)	0.0257 (3)
H7A	0.7404	0.2350	0.8253	0.031*
H7B	0.9191	0.2433	0.9038	0.031*
C3	0.66532 (15)	0.03264 (16)	1.12009 (11)	0.0250 (3)
H3	0.6273	0.0817	1.1816	0.030*
C8	0.89813 (14)	0.07728 (16)	0.77779 (10)	0.0252 (3)
N1	0.94789 (13)	0.00673 (14)	0.70957 (10)	0.0313 (3)
C10	0.88145 (15)	0.38338 (15)	1.10361 (10)	0.0248 (4)
C9	0.71906 (14)	0.31597 (16)	1.05579 (11)	0.0249 (3)
H9A	0.6768	0.3666	0.9805	0.030*
H9B	0.6438	0.3448	1.1064	0.030*
C5	0.71958 (14)	−0.20835 (16)	1.02028 (11)	0.0278 (4)
H5	0.7192	−0.3242	1.0126	0.033*
C6	0.77646 (14)	−0.11076 (16)	0.94203 (11)	0.0248 (4)
H6	0.8146	−0.1607	0.8809	0.030*
N2	1.00792 (13)	0.43446 (14)	1.14226 (9)	0.0318 (3)
C4	0.66348 (14)	−0.13701 (17)	1.10929 (11)	0.0271 (3)
H4	0.6239	−0.2034	1.1628	0.033*

	U11	U22	U33	U12	U13	U23
C1	0.0169 (6)	0.0226 (7)	0.0238 (7)	0.0002 (4)	0.0009 (5)	0.0007 (5)
C2	0.0176 (6)	0.0247 (7)	0.0221 (7)	0.0023 (5)	0.0013 (5)	−0.0002 (5)
C7	0.0267 (7)	0.0232 (7)	0.0274 (7)	0.0013 (5)	0.0062 (5)	0.0001 (6)
C3	0.0207 (7)	0.0311 (8)	0.0220 (7)	−0.0002 (5)	0.0019 (5)	−0.0002 (6)
C8	0.0217 (7)	0.0285 (7)	0.0252 (7)	−0.0031 (5)	0.0043 (5)	0.0008 (6)
N1	0.0292 (7)	0.0337 (8)	0.0319 (7)	−0.0012 (5)	0.0085 (5)	−0.0019 (5)
C10	0.0321 (7)	0.0198 (7)	0.0243 (7)	0.0044 (5)	0.0097 (6)	−0.0012 (5)
C9	0.0256 (7)	0.0240 (8)	0.0250 (7)	0.0021 (5)	0.0049 (5)	−0.0018 (6)
C5	0.0257 (7)	0.0210 (7)	0.0342 (8)	−0.0006 (5)	0.0007 (6)	0.0018 (6)
C6	0.0241 (7)	0.0235 (8)	0.0263 (7)	0.0027 (5)	0.0040 (5)	−0.0023 (6)
N2	0.0325 (7)	0.0272 (7)	0.0359 (7)	−0.0019 (5)	0.0071 (5)	−0.0044 (5)
C4	0.0234 (7)	0.0314 (8)	0.0253 (7)	−0.0034 (5)	0.0022 (5)	0.0054 (6)

C1—C6	1.3890 (19)	C8—N1	1.1471 (15)
C1—C2	1.4025 (16)	C10—N2	1.1452 (15)
C1—C7	1.5218 (18)	C10—C9	1.4714 (17)
C2—C3	1.3882 (18)	C9—H9A	0.9900
C2—C9	1.5159 (18)	C9—H9B	0.9900
C7—C8	1.4599 (17)	C5—C4	1.3809 (18)
C7—H7A	0.9900	C5—C6	1.3882 (17)
C7—H7B	0.9900	C5—H5	0.9500
C3—C4	1.390 (2)	C6—H6	0.9500
C3—H3	0.9500	C4—H4	0.9500
C6—C1—C2	119.02 (11)	N2—C10—C9	178.97 (14)
C6—C1—C7	121.58 (11)	C10—C9—C2	112.32 (10)
C2—C1—C7	119.36 (12)	C10—C9—H9A	109.1
C3—C2—C1	119.52 (13)	C2—C9—H9A	109.1
C3—C2—C9	119.34 (11)	C10—C9—H9B	109.1
C1—C2—C9	121.14 (11)	C2—C9—H9B	109.1
C8—C7—C1	113.88 (11)	H9A—C9—H9B	107.9
C8—C7—H7A	108.8	C4—C5—C6	120.00 (12)
C1—C7—H7A	108.8	C4—C5—H5	120.0
C8—C7—H7B	108.8	C6—C5—H5	120.0
C1—C7—H7B	108.8	C1—C6—C5	121.00 (11)
H7A—C7—H7B	107.7	C1—C6—H6	119.5
C2—C3—C4	120.94 (12)	C5—C6—H6	119.5
C2—C3—H3	119.5	C5—C4—C3	119.53 (12)
C4—C3—H3	119.5	C5—C4—H4	120.2
N1—C8—C7	179.54 (14)	C3—C4—H4	120.2
C6—C1—C2—C3	0.04 (16)	C3—C2—C9—C10	103.33 (13)
C7—C1—C2—C3	177.52 (11)	C1—C2—C9—C10	−77.54 (13)
C6—C1—C2—C9	−179.09 (11)	C2—C1—C6—C5	0.00 (17)
C7—C1—C2—C9	−1.61 (15)	C7—C1—C6—C5	−177.43 (10)
C6—C1—C7—C8	−5.75 (16)	C4—C5—C6—C1	0.15 (18)
C2—C1—C7—C8	176.84 (10)	C6—C5—C4—C3	−0.34 (18)
C1—C2—C3—C4	−0.23 (17)	C2—C3—C4—C5	0.38 (18)
C9—C2—C3—C4	178.91 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···N1i	0.99	2.57	3.5605 (18)	176
C9—H9B···N1ii	0.99	2.56	3.5210 (17)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯N1i	0.99	2.57	3.5605 (18)	176
C9—H9B⋯N1ii	0.99	2.56	3.5210 (17)	165

Symmetry codes: (i) ; (ii) .