4,4-Diacetyl-hepta-nedinitrile.

The asymmetric unit of the title compound, C(11)H(14)N(2)O(2), contains one half-mol-ecule as the central C atom of the mol-ecule lies on a twofold rotation axis. In the crystal structure, weak inter-molecular C-H⋯N hydrogen bonds link the mol-ecules into zigzag chains along c.

Related literature

For details of the biological activity of amino­thia­zoles, see: Kabalka & Mereddy (2006 ▶). For their use in organic synthesis, see: Kim et al. (2001 ▶); Ranu & Banerjee (2005 ▶); Ranu et al. (2006 ▶); Wang et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H14N2O2

M = 206.24

Monoclinic,

a = 12.562 (3) Å

b = 7.8700 (16) Å

c = 10.941 (2) Å

β = 84.91 (3)°

V = 1077.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.961, T max = 0.991

1009 measured reflections

974 independent reflections

758 reflections with I > 2σ(I)

R int = 0.024

3 standard reflections every 200 reflections intensity decay: 9%

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.152

S = 1.00

974 reflections

70 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039962/sj2557sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039962/sj2557Isup2.hkl

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

C11H14N2O2	F(000) = 440
Mr = 206.24	Dx = 1.271 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 12.562 (3) Å	θ = 10–13°
b = 7.8700 (16) Å	µ = 0.09 mm−1
c = 10.941 (2) Å	T = 293 K
β = 84.91 (3)°	Block, colourless
V = 1077.4 (4) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	758 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 25.3°, θmin = 3.1°
ω/2θ scans	h = −14→15
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
Tmin = 0.961, Tmax = 0.991	l = 0→13
1009 measured reflections	3 standard reflections every 200 reflections
974 independent reflections	intensity decay: 9%

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0339P)2 + 4.1549P] where P = (Fo2 + 2Fc2)/3
974 reflections	(Δ/σ)max < 0.001
70 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. 1H NMR (DMSO, δ, p.p.m.) 2.15 (s, 6H), 2.23 (t, 4H), 2.31(t, 4H).

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
O	0.65270 (17)	−0.0258 (3)	0.3475 (2)	0.0523 (7)
N	0.3630 (3)	0.4652 (4)	0.5714 (3)	0.0646 (9)
C1	0.6246 (3)	−0.1760 (4)	0.1653 (3)	0.0495 (9)
H1A	0.6530	−0.1210	0.0912	0.074*
H1B	0.5608	−0.2368	0.1503	0.074*
H1C	0.6765	−0.2541	0.1920	0.074*
C2	0.5988 (2)	−0.0454 (4)	0.2629 (3)	0.0369 (7)
C3	0.5000	0.0686 (5)	0.2500	0.0288 (8)
C4	0.3719 (2)	0.3939 (4)	0.4802 (3)	0.0442 (8)
C5	0.3865 (3)	0.3008 (4)	0.3639 (3)	0.0440 (8)
H5A	0.4002	0.3802	0.2966	0.053*
H5B	0.3218	0.2383	0.3511	0.053*
C6	0.4802 (2)	0.1776 (4)	0.3665 (2)	0.0341 (7)
H6A	0.4670	0.1029	0.4367	0.041*
H6B	0.5445	0.2421	0.3777	0.041*

	U11	U22	U33	U12	U13	U23
O	0.0447 (12)	0.0599 (15)	0.0551 (13)	0.0160 (11)	−0.0197 (10)	−0.0091 (12)
N	0.072 (2)	0.0551 (19)	0.0633 (19)	0.0016 (17)	0.0109 (15)	−0.0178 (17)
C1	0.0502 (19)	0.0408 (19)	0.057 (2)	0.0116 (15)	−0.0038 (15)	−0.0075 (16)
C2	0.0355 (15)	0.0341 (16)	0.0418 (16)	0.0002 (13)	−0.0073 (12)	0.0048 (13)
C3	0.0305 (18)	0.0244 (19)	0.0319 (19)	0.000	−0.0057 (15)	0.000
C4	0.0466 (17)	0.0325 (16)	0.0519 (19)	0.0021 (14)	0.0048 (14)	−0.0001 (15)
C5	0.0497 (18)	0.0375 (17)	0.0440 (17)	0.0072 (14)	−0.0005 (13)	−0.0057 (14)
C6	0.0423 (15)	0.0281 (15)	0.0324 (14)	0.0013 (12)	−0.0058 (11)	0.0006 (12)

O—C2	1.205 (3)	C3—C6	1.538 (3)
N—C4	1.142 (4)	C4—C5	1.466 (4)
C1—C2	1.497 (4)	C5—C6	1.528 (4)
C1—H1A	0.9600	C5—H5A	0.9700
C1—H1B	0.9600	C5—H5B	0.9700
C1—H1C	0.9600	C6—H6A	0.9700
C2—C3	1.547 (3)	C6—H6B	0.9700
C2—C1—H1A	109.5	N—C4—C5	178.3 (4)
C2—C1—H1B	109.5	C4—C5—C6	109.8 (3)
H1A—C1—H1B	109.5	C4—C5—H5A	109.7
C2—C1—H1C	109.5	C6—C5—H5A	109.7
H1A—C1—H1C	109.5	C4—C5—H5B	109.7
H1B—C1—H1C	109.5	C6—C5—H5B	109.7
O—C2—C1	122.3 (3)	H5A—C5—H5B	108.2
O—C2—C3	120.4 (3)	C5—C6—C3	114.0 (2)
C1—C2—C3	117.2 (2)	C5—C6—H6A	108.8
C6—C3—C6i	112.2 (3)	C3—C6—H6A	108.8
C6—C3—C2i	109.09 (15)	C5—C6—H6B	108.8
C6—C3—C2	108.63 (15)	C3—C6—H6B	108.8
C2i—C3—C2	109.2 (3)	H6A—C6—H6B	107.6
O—C2—C3—C6	−7.9 (4)	C1—C2—C3—C2i	54.4 (2)
C1—C2—C3—C6	173.3 (3)	C4—C5—C6—C3	178.0 (2)
O—C2—C3—C6i	114.6 (3)	C6i—C3—C6—C5	57.5 (2)
C1—C2—C3—C6i	−64.2 (3)	C2i—C3—C6—C5	−62.9 (3)
O—C2—C3—C2i	−126.8 (3)	C2—C3—C6—C5	178.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···Nii	0.97	2.66	3.533 (5)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6B⋯Ni	0.97	2.66	3.533 (5)	150

Symmetry code: (i) .