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

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.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.133
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

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Alert level G
PLAT793_ALERT_2_G Check the Absolute Configuration of C2     .....          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
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   0 ALERT type 5 Informative message, check

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S1. Comment

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

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

S2. Experimental

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).

S3. Refinement

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

Computing details

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

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

Crystal data

C11H14N2O	F(000) = 408
Mr = 190.24	Dx = 1.161 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 798 reflections
a = 18.261 (3) Å	θ = 2.9–23.6°
b = 7.8182 (10) Å	µ = 0.08 mm^−1
c = 8.1943 (11) Å	T = 294 K
β = 111.510 (9)°	Block, colorless
V = 1088.4 (3) Å^3	0.24 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	1114 independent reflections
Radiation source: fine-focus sealed tube	644 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
ω scans	θmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −22→14
Tmin = 0.971, Tmax = 0.992	k = −9→9
3003 measured reflections	l = −10→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0588P)^2 + 0.1398P] where P = (Fo^2 + 2Fc^2)/3
1114 reflections	(Δ/σ)max = 0.002
65 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	1.0000	1.0500 (2)	0.2500	0.0639 (6)
N1	0.69534 (13)	0.8243 (3)	−0.3591 (3)	0.0968 (8)
C1	1.0000	0.8948 (3)	0.2500	0.0495 (7)
C2	0.95717 (10)	0.7841 (2)	0.0927 (2)	0.0491 (5)
H2	0.9889	0.7818	0.0189	0.059*
C3	0.96129 (10)	0.6064 (2)	0.1722 (2)	0.0555 (5)
H3A	0.9174	0.5874	0.2097	0.067*
H3B	0.9609	0.5184	0.0884	0.067*
C4	0.87656 (11)	0.8505 (2)	−0.0189 (2)	0.0579 (6)
H4A	0.8805	0.9706	−0.0443	0.069*
H4B	0.8417	0.8409	0.0461	0.069*
C5	0.84170 (11)	0.7522 (3)	−0.1902 (3)	0.0627 (6)
H5A	0.8720	0.7769	−0.2630	0.075*
H5B	0.8460	0.6305	−0.1651	0.075*
C6	0.75994 (14)	0.7945 (3)	−0.2864 (3)	0.0672 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0821 (14)	0.0465 (12)	0.0598 (12)	0.000	0.0223 (10)	0.000
N1	0.0764 (15)	0.1164 (18)	0.0812 (15)	0.0217 (12)	0.0096 (11)	−0.0174 (13)
C1	0.0539 (15)	0.0485 (17)	0.0538 (16)	0.000	0.0286 (13)	0.000
C2	0.0550 (11)	0.0493 (11)	0.0462 (11)	0.0005 (8)	0.0222 (9)	−0.0018 (8)
C3	0.0605 (11)	0.0496 (11)	0.0569 (11)	−0.0020 (9)	0.0221 (9)	−0.0027 (9)
C4	0.0598 (12)	0.0566 (12)	0.0554 (12)	0.0026 (9)	0.0191 (10)	−0.0027 (10)
C5	0.0624 (14)	0.0638 (12)	0.0570 (13)	0.0006 (10)	0.0159 (11)	−0.0072 (10)
C6	0.0680 (14)	0.0697 (15)	0.0570 (13)	0.0067 (12)	0.0147 (11)	−0.0095 (11)

Geometric parameters (Å, º)

O1—C1	1.213 (3)	C3—H3A	0.9700
N1—C6	1.134 (3)	C3—H3B	0.9700
C1—C2	1.511 (2)	C4—C5	1.521 (2)
C1—C2^i	1.511 (2)	C4—H4A	0.9700
C2—C4	1.512 (2)	C4—H4B	0.9700
C2—C3	1.525 (2)	C5—C6	1.448 (3)
C2—H2	0.9800	C5—H5A	0.9700
C3—C3^i	1.518 (3)	C5—H5B	0.9700
O1—C1—C2	124.94 (10)	H3A—C3—H3B	109.0
O1—C1—C2^i	124.95 (10)	C2—C4—C5	111.70 (15)
C2—C1—C2^i	110.1 (2)	C2—C4—H4A	109.3
C1—C2—C4	113.82 (14)	C5—C4—H4A	109.3
C1—C2—C3	103.22 (15)	C2—C4—H4B	109.3
C4—C2—C3	117.13 (15)	C5—C4—H4B	109.3
C1—C2—H2	107.4	H4A—C4—H4B	107.9
C4—C2—H2	107.4	C6—C5—C4	112.71 (17)
C3—C2—H2	107.4	C6—C5—H5A	109.1
C3^i—C3—C2	104.12 (10)	C4—C5—H5A	109.1
C3^i—C3—H3A	110.9	C6—C5—H5B	109.1
C2—C3—H3A	110.9	C4—C5—H5B	109.1
C3^i—C3—H3B	110.9	H5A—C5—H5B	107.8
C2—C3—H3B	110.9	N1—C6—C5	178.1 (3)
O1—C1—C2—C4	−39.96 (17)	C4—C2—C3—C3^i	−157.50 (18)
C2^i—C1—C2—C4	140.04 (17)	C1—C2—C4—C5	170.57 (15)
O1—C1—C2—C3	−167.96 (8)	C3—C2—C4—C5	−69.0 (2)
C2^i—C1—C2—C3	12.04 (8)	C2—C4—C5—C6	170.72 (17)
C1—C2—C3—C3^i	−31.6 (2)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···N1^ii	0.97	2.54	3.466 (3)	160

Symmetry code: (ii) −x+3/2, y−1/2, −z−1/2.