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Acta Cryst. (2008). E64, o391    [ doi:10.1107/S1600536807068535 ]

3,3'-(2-Oxocyclopentane-1,3-diyl)dipropanenitrile

Y. Deng, Y.-X. Chen, Z.-L. Gao, J.-H. Yang and W. Wang

Abstract top

The complete molecule of the title compound, C11H14N2O, is generated by crystallographic twofold symmetry, with the C=O group lying on the rotation axis. In the crystal structure, weak C-H...N interactions form zigzag chains of molecules.

Comment top

The title compound, (I), which was first prepared by Westman & Kober (1964), is as a intermediate in the synthesis of 6,7-dihydro-5H-cyclopenta[b]pyridine ramification. We report here its structure (Fig. 1). For a related structure, see Chen et al. (2007).

The complete molecule of (I) is generated by crystallographic 2-fold symmetry, with the C=O group lying on the rotation axis. In the crystal, weak C—H···N interactions (Table 1) lead to zigzag chains of molecules.

Related literature top

For the synthesis, see: Westman & Kober (1964). For a similar compound, see: Chen et al. (2007).

Experimental top

The title compound was prepared according to the method of Westman & Kober (1964). Colourless blocks of (I) were obtained by slow evaporation of a methanol solution (m.p. 335–336 K).

Refinement top

All the H atoms were positioned geometrically (C—H = 0.97–0.98 Å), and refined as riding with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I). Displacement ellopsoids are drawn at the 40% probability level and H atoms are shown as small spheres of arbitrary radius. Symmetry code: (i) 2 - x, y, 1/2 - z.
3,3'-(2-Oxocyclopentane-1,3-diyl)dipropanenitrile top
Crystal data top
C11H14N2OF000 = 408
Mr = 190.24Dx = 1.161 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 798 reflections
a = 18.261 (3) Åθ = 2.9–23.6º
b = 7.8182 (10) ŵ = 0.08 mm−1
c = 8.1943 (11) ÅT = 294 (2) K
β = 111.510 (9)ºBlock, colorless
V = 1088.4 (3) Å30.24 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer		1114 independent reflections
Radiation source: fine-focus sealed tube644 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.045
T = 294(2) Kθmax = 26.4º
ω scansθmin = 2.4º
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		h = −22→14
Tmin = 0.971, Tmax = 0.992k = −9→9
3003 measured reflectionsl = −10→9
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.133  w = 1/[σ2(Fo2) + (0.0588P)2 + 0.1398P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.002
1114 reflectionsΔρmax = 0.15 e Å−3
65 parametersΔρmin = −0.13 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C11H14N2OV = 1088.4 (3) Å3
Mr = 190.24Z = 4
Monoclinic, C2/cMo Kα
a = 18.261 (3) ŵ = 0.08 mm−1
b = 7.8182 (10) ÅT = 294 (2) K
c = 8.1943 (11) Å0.24 × 0.20 × 0.10 mm
β = 111.510 (9)º
Data collection top
Bruker SMART CCD
diffractometer		1114 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		644 reflections with I > 2σ(I)
Tmin = 0.971, Tmax = 0.992Rint = 0.045
3003 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04865 parameters
wR(F2) = 0.133H-atom parameters constrained
S = 1.03Δρmax = 0.15 e Å−3
1114 reflectionsΔρmin = −0.13 e Å−3
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
xyzUiso*/Ueq
O11.00001.0500 (2)0.25000.0639 (6)
N10.69534 (13)0.8243 (3)−0.3591 (3)0.0968 (8)
C11.00000.8948 (3)0.25000.0495 (7)
C20.95717 (10)0.7841 (2)0.0927 (2)0.0491 (5)
H20.98890.78180.01890.059*
C30.96129 (10)0.6064 (2)0.1722 (2)0.0555 (5)
H3A0.91740.58740.20970.067*
H3B0.96090.51840.08840.067*
C40.87656 (11)0.8505 (2)−0.0189 (2)0.0579 (6)
H4A0.88050.9706−0.04430.069*
H4B0.84170.84090.04610.069*
C50.84170 (11)0.7522 (3)−0.1902 (3)0.0627 (6)
H5A0.87200.7769−0.26300.075*
H5B0.84600.6305−0.16510.075*
C60.75994 (14)0.7945 (3)−0.2864 (3)0.0672 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0821 (14)0.0465 (12)0.0598 (12)0.0000.0223 (10)0.000
N10.0764 (15)0.1164 (18)0.0812 (15)0.0217 (12)0.0096 (11)−0.0174 (13)
C10.0539 (15)0.0485 (17)0.0538 (16)0.0000.0286 (13)0.000
C20.0550 (11)0.0493 (11)0.0462 (11)0.0005 (8)0.0222 (9)−0.0018 (8)
C30.0605 (11)0.0496 (11)0.0569 (11)−0.0020 (9)0.0221 (9)−0.0027 (9)
C40.0598 (12)0.0566 (12)0.0554 (12)0.0026 (9)0.0191 (10)−0.0027 (10)
C50.0624 (14)0.0638 (12)0.0570 (13)0.0006 (10)0.0159 (11)−0.0072 (10)
C60.0680 (14)0.0697 (15)0.0570 (13)0.0067 (12)0.0147 (11)−0.0095 (11)
Geometric parameters (Å, °) top
O1—C11.213 (3)C3—H3A0.9700
N1—C61.134 (3)C3—H3B0.9700
C1—C21.511 (2)C4—C51.521 (2)
C1—C2i1.511 (2)C4—H4A0.9700
C2—C41.512 (2)C4—H4B0.9700
C2—C31.525 (2)C5—C61.448 (3)
C2—H20.9800C5—H5A0.9700
C3—C3i1.518 (3)C5—H5B0.9700
O1—C1—C2124.94 (10)H3A—C3—H3B109.0
O1—C1—C2i124.95 (10)C2—C4—C5111.70 (15)
C2—C1—C2i110.1 (2)C2—C4—H4A109.3
C1—C2—C4113.82 (14)C5—C4—H4A109.3
C1—C2—C3103.22 (15)C2—C4—H4B109.3
C4—C2—C3117.13 (15)C5—C4—H4B109.3
C1—C2—H2107.4H4A—C4—H4B107.9
C4—C2—H2107.4C6—C5—C4112.71 (17)
C3—C2—H2107.4C6—C5—H5A109.1
C3i—C3—C2104.12 (10)C4—C5—H5A109.1
C3i—C3—H3A110.9C6—C5—H5B109.1
C2—C3—H3A110.9C4—C5—H5B109.1
C3i—C3—H3B110.9H5A—C5—H5B107.8
C2—C3—H3B110.9N1—C6—C5178.1 (3)
O1—C1—C2—C4−39.96 (17)C4—C2—C3—C3i−157.50 (18)
C2i—C1—C2—C4140.04 (17)C1—C2—C4—C5170.57 (15)
O1—C1—C2—C3−167.96 (8)C3—C2—C4—C5−69.0 (2)
C2i—C1—C2—C312.04 (8)C2—C4—C5—C6170.72 (17)
C1—C2—C3—C3i−31.6 (2)
Symmetry codes: (i) −x+2, y, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5B···N1ii0.972.543.466 (3)160
Symmetry codes: (ii) −x+3/2, y−1/2, −z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5B···N1i0.972.543.466 (3)160
Symmetry codes: (i) −x+3/2, y−1/2, −z−1/2.
references
References top

Bruker (1997). SMART, SAINT, SADABS and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Chen, Y., Yang, J., Deng, Y., Li, G. & Wang, W. (2007). Acta Cryst. E63, o4054–?.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westman, T. L. & Kober, A. E. (1964). J. Org. Chem. 29, 2448–2450.