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Acta Cryst. (2010). E66, o170    [ doi:10.1107/S1600536809052908 ]

1,1'-(p-Phenylenedimethylene)dipiperidin-4-one

V. Vijayakumar, K. Rajesh, J. Suresh, T. Narasimhamurthy and P. L. N. Lakshman

Abstract top

In the molecule of the title compound, C18H24N2O2, the piperidine rings are in chair conformations. The crystal structure is stabilized by intermolecular C-H...O hydrogen bonding. There are neither C-H...[pi] nor [pi]-[pi] interactions in the structure.

Comment top

The configuration and conformation of the title compound, (I) and the atom numbering scheme are shown in the ORTEP drawing (Fig. 1). The piperidone ring exibits chair conformation as evident from the puckering parameters (Q)=0.549 (1) Å, θ = 173.4 (2) °, ψ = 181.9 (1) ° (Cremer & Pople, 1975).

In the crystal structure, an intermolecular C—H···O bond is found generating R22(24) motif (Bernstein et al., 1995).

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring puckering parameters, see Cremer & Pople (1975).

Experimental top

A mixture of 4-piperidone monohydrate hydrochloride (2 mol), 1,4-bis(bromomethyl)benzene (1 mol) and potassium carbonate (6 mol) in anhydrous benzene was refluxed for 7 h. The completion of reaction was monitored by TLC. Potassium carbonate was filtered off and the excess solvent was removed under reduced pressure. The solid obtained was purified over a column of silica gel (60–120 mesh size) using benzene-ethyl acetate (60–80 °C) in the ratio of 20:80. Yield: 40% m.p. 289°C.

Refinement top

The H atoms were placed in calculated positions and allowed to ride on their carrier atoms with C—H = 0.93–0.97 Å.Uiso = 1.2Ueq(C) for CH and CH2 groups.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of title compound with atom numbering scheme and 50% probability displacement ellipsoids.
1,1'-(p-Phenylenedimethylene)dipiperidin-4-one top
Crystal data top
C18H24N2O2F(000) = 324
Mr = 300.39Dx = 1.249 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2500 reflections
a = 6.2701 (5) Åθ = 2–30°
b = 8.0990 (6) ŵ = 0.08 mm−1
c = 15.8978 (13) ÅT = 293 K
β = 98.275 (2)°Block, colourless
V = 798.91 (11) Å30.19 × 0.17 × 0.15 mm
Z = 2
Data collection top
Bruker SMART APEX CCD
diffractometer		1826 independent reflections
Radiation source: fine-focus sealed tube1424 reflections with I > 2σ(I)
graphiteRint = 0.014
ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		h = −8→4
Tmin = 0.984, Tmax = 0.987k = −10→10
4782 measured reflectionsl = −20→19
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0639P)2 + 0.1074P]
where P = (Fo2 + 2Fc2)/3
1826 reflections(Δ/σ)max < 0.001
100 parametersΔρmax = 0.20 e Å−3
0 restraintsΔρmin = −0.14 e Å−3
Crystal data top
C18H24N2O2V = 798.91 (11) Å3
Mr = 300.39Z = 2
Monoclinic, P21/nMo Kα radiation
a = 6.2701 (5) ŵ = 0.08 mm−1
b = 8.0990 (6) ÅT = 293 K
c = 15.8978 (13) Å0.19 × 0.17 × 0.15 mm
β = 98.275 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer		1826 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		1424 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.987Rint = 0.014
4782 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.123Δρmax = 0.20 e Å−3
S = 1.05Δρmin = −0.14 e Å−3
1826 reflectionsAbsolute structure: ?
100 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
C20.2931 (2)0.43945 (15)0.38729 (9)0.0451 (3)
H2A0.32780.43300.32990.054*
H2B0.41960.40600.42600.054*
C30.2358 (2)0.61783 (16)0.40660 (10)0.0544 (4)
H3A0.21910.62760.46610.065*
H3B0.35190.69050.39590.065*
C40.0312 (2)0.66908 (16)0.35253 (8)0.0440 (3)
C5−0.1488 (2)0.54905 (18)0.35354 (11)0.0584 (4)
H5A−0.26800.57960.31050.070*
H5B−0.19910.55280.40840.070*
C6−0.0757 (2)0.37490 (18)0.33662 (10)0.0544 (4)
H6A−0.19180.29820.34190.065*
H6B−0.04340.36820.27890.065*
C70.1742 (2)0.15730 (16)0.37561 (9)0.0493 (4)
H7A0.22500.15750.32080.059*
H7B0.04580.08910.37050.059*
C80.3452 (2)0.07991 (14)0.44028 (8)0.0405 (3)
C90.3083 (2)0.05404 (16)0.52331 (8)0.0450 (3)
H90.17990.09000.54000.054*
C100.5395 (2)0.02482 (16)0.41824 (8)0.0444 (3)
H100.56820.04110.36310.053*
N10.11571 (16)0.32682 (12)0.39582 (7)0.0395 (3)
O10.01374 (19)0.79483 (13)0.31091 (7)0.0657 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0372 (6)0.0349 (7)0.0605 (8)−0.0033 (5)−0.0021 (5)0.0041 (6)
C30.0595 (8)0.0329 (7)0.0659 (9)−0.0062 (6)−0.0079 (7)0.0018 (6)
C40.0549 (8)0.0322 (6)0.0448 (7)0.0048 (5)0.0072 (6)0.0015 (5)
C50.0415 (7)0.0509 (9)0.0821 (10)0.0057 (6)0.0064 (7)0.0227 (7)
C60.0423 (7)0.0422 (8)0.0731 (10)−0.0085 (6)−0.0107 (7)0.0130 (7)
C70.0586 (8)0.0308 (7)0.0540 (8)−0.0024 (6)−0.0075 (6)−0.0006 (6)
C80.0502 (7)0.0233 (5)0.0464 (7)−0.0019 (5)0.0015 (5)−0.0002 (5)
C90.0462 (7)0.0374 (7)0.0528 (8)0.0024 (5)0.0113 (6)−0.0021 (5)
C100.0573 (8)0.0368 (7)0.0401 (6)−0.0039 (6)0.0106 (6)0.0016 (5)
N10.0389 (5)0.0288 (5)0.0484 (6)−0.0026 (4)−0.0022 (4)0.0059 (4)
O10.0827 (8)0.0385 (6)0.0723 (7)−0.0004 (5)−0.0012 (6)0.0175 (5)
Geometric parameters (Å, °) top
C2—N11.4598 (16)C6—H6A0.9700
C2—C31.5304 (18)C6—H6B0.9700
C2—H2A0.9700C7—N11.4685 (17)
C2—H2B0.9700C7—C81.5104 (18)
C3—C41.4964 (19)C7—H7A0.9700
C3—H3A0.9700C7—H7B0.9700
C3—H3B0.9700C8—C91.3884 (18)
C4—O11.2109 (16)C8—C101.3888 (19)
C4—C51.492 (2)C9—C10i1.3882 (18)
C5—C61.519 (2)C9—H90.9300
C5—H5A0.9700C10—C9i1.3882 (18)
C5—H5B0.9700C10—H100.9300
C6—N11.4670 (16)
N1—C2—C3111.55 (11)C5—C6—H6A109.2
N1—C2—H2A109.3N1—C6—H6B109.2
C3—C2—H2A109.3C5—C6—H6B109.2
N1—C2—H2B109.3H6A—C6—H6B107.9
C3—C2—H2B109.3N1—C7—C8114.47 (10)
H2A—C2—H2B108.0N1—C7—H7A108.6
C4—C3—C2110.67 (11)C8—C7—H7A108.6
C4—C3—H3A109.5N1—C7—H7B108.6
C2—C3—H3A109.5C8—C7—H7B108.6
C4—C3—H3B109.5H7A—C7—H7B107.6
C2—C3—H3B109.5C9—C8—C10117.61 (11)
H3A—C3—H3B108.1C9—C8—C7120.72 (12)
O1—C4—C5123.01 (13)C10—C8—C7121.59 (12)
O1—C4—C3123.37 (13)C10i—C9—C8120.89 (12)
C5—C4—C3113.62 (11)C10i—C9—H9119.6
C4—C5—C6110.77 (12)C8—C9—H9119.6
C4—C5—H5A109.5C9i—C10—C8121.50 (12)
C6—C5—H5A109.5C9i—C10—H10119.3
C4—C5—H5B109.5C8—C10—H10119.3
C6—C5—H5B109.5C2—N1—C6109.77 (10)
H5A—C5—H5B108.1C2—N1—C7110.25 (11)
N1—C6—C5111.90 (12)C6—N1—C7108.36 (10)
N1—C6—H6A109.2
N1—C2—C3—C4−54.57 (16)C7—C8—C9—C10i176.62 (11)
C2—C3—C4—O1−129.37 (15)C9—C8—C10—C9i0.3 (2)
C2—C3—C4—C549.69 (17)C7—C8—C10—C9i−176.59 (12)
O1—C4—C5—C6129.33 (15)C3—C2—N1—C659.82 (15)
C3—C4—C5—C6−49.73 (18)C3—C2—N1—C7179.12 (11)
C4—C5—C6—N154.57 (17)C5—C6—N1—C2−60.02 (16)
N1—C7—C8—C962.64 (17)C5—C6—N1—C7179.53 (12)
N1—C7—C8—C10−120.58 (14)C8—C7—N1—C269.70 (15)
C10—C8—C9—C10i−0.3 (2)C8—C7—N1—C6−170.15 (12)
Symmetry codes: (i) −x+1, −y, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C7—H7B···O1ii0.972.563.2235 (17)126
Symmetry codes: (ii) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C7—H7B···O1i0.972.563.2235 (17)126
Symmetry codes: (i) x, y−1, z.
Acknowledgements top

VV thanks the DST-India for funding through Young Scientist-Fast Track Proposal.

references
References top

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.

Bruker (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.

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

Spek, A. L. (2009). Acta Cryst. D65, 148–155.