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

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

doi:10.1107/S1600536807068535

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o391

doi:10.1107/S1600536807068535

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

Yi Deng,^a ^* Yan-Xue Chen,^b Zhi-Lei Gao,^b Jin-Hui Yang ^c and Wei Wang ^b

^aCollege of Pharmaceuticals & Biotechnology, Tianjin University, Tianjin 300072, People's Republic of China, ^bSchool of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, People's Republic of China, and ^cSchool of Materials Science and Engineering, Shijizhuang Railway Institute, Shijiazhuang 050043, People's Republic of China
^*Correspondence e-mail: dengyicoo@yahoo.com.cn

(Received 26 December 2007; accepted 27 December 2007; online 9 January 2008)

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.

Related literature

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

Experimental

Crystal data

C₁₁H₁₄N₂O
M_r = 190.24
Monoclinic, C 2/c
a = 18.261 (3) Å
b = 7.8182 (10) Å
c = 8.1943 (11) Å
β = 111.510 (9)°
V = 1088.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 (2) K
0.24 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.971, T_max = 0.992
3003 measured reflections
1114 independent reflections
644 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.133
S = 1.03
1114 reflections
65 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯N1ⁱ	0.97	2.54	3.466 (3)	160
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068535/hb2685sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068535/hb2685Isup2.hkl

checkCIF report

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).

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

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

C₁₁H₁₄N₂O	F(000) = 408
M_r = 190.24	D_x = 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) Å³	0.24 × 0.20 × 0.10 mm
Z = 4

Data collection top

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

Refinement top

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0588P)² + 0.1398P] where P = (F_o² + 2F_c²)/3
1114 reflections	(Δ/σ)_max = 0.002
65 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₁H₁₄N₂O	V = 1088.4 (3) Å³
M_r = 190.24	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.261 (3) Å	µ = 0.08 mm⁻¹
b = 7.8182 (10) Å	T = 294 K
c = 8.1943 (11) Å	0.24 × 0.20 × 0.10 mm
β = 111.510 (9)°

Data collection top

Bruker SMART CCD diffractometer	1114 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	644 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.992	R_int = 0.045
3003 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.03	Δρ_max = 0.15 e Å⁻³
1114 reflections	Δρ_min = −0.13 e Å⁻³
65 parameters

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

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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—C2ⁱ	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—C3ⁱ	1.518 (3)	C5—H5B	0.9700

O1—C1—C2	124.94 (10)	H3A—C3—H3B	109.0
O1—C1—C2ⁱ	124.95 (10)	C2—C4—C5	111.70 (15)
C2—C1—C2ⁱ	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
C3ⁱ—C3—C2	104.12 (10)	C4—C5—H5A	109.1
C3ⁱ—C3—H3A	110.9	C6—C5—H5B	109.1
C2—C3—H3A	110.9	C4—C5—H5B	109.1
C3ⁱ—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—C3ⁱ	−157.50 (18)
C2ⁱ—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)
C2ⁱ—C1—C2—C3	12.04 (8)	C2—C4—C5—C6	170.72 (17)
C1—C2—C3—C3ⁱ	−31.6 (2)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···N1ⁱⁱ	0.97	2.54	3.466 (3)	160

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₄N₂O
M_r	190.24
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	18.261 (3), 7.8182 (10), 8.1943 (11)
β (°)	111.510 (9)
V (Å³)	1088.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.24 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.971, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	3003, 1114, 644
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.133, 1.03
No. of reflections	1114
No. of parameters	65
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.13

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···N1ⁱ	0.97	2.54	3.466 (3)	160

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

References

Bruker (1997). SMART, SAINT, SADABS and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Y., Yang, J., Deng, Y., Li, G. & Wang, W. (2007). Acta Cryst. E63, o4054. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westman, T. L. & Kober, A. E. (1964). J. Org. Chem. 29, 2448–2450. CrossRef CAS Web of Science Google Scholar