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

Abstract

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,

• a = 18.261 (3) Å

• b = 7.8182 (10) Å

• c = 8.1943 (11) Å

• β = 111.510 (9)°

• V = 1088.4 (3) ų

• 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[F ² > 2σ(F ²)] = 0.048

• wR(F ²) = 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

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).

Supplementary Material

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

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) .

supplementary crystallographic information

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.

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).

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).

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.

Crystal data

C11H14N2O	F000 = 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 = 2.9–23.6º
b = 7.8182 (10) Å	µ = 0.08 mm−1
c = 8.1943 (11) Å	T = 294 (2) K
β = 111.510 (9)º	Block, colorless
V = 1088.4 (3) Å3	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)
Monochromator: graphite	Rint = 0.045
T = 294(2) K	θmax = 26.4º
ω scans	θmin = 2.4º
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 F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-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 reflections	Δρmax = 0.15 e Å−3
65 parameters	Δρmin = −0.13 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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)

	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, °)

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 codes: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, °)

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

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