c-3,t-3-Dimethyl-r-2,c-6-diphenyl­piperidin-4-one

M Thenmozhi; S Ponnuswamy; J Umamaheshwari; M Jamesh; M N Ponnuswamy

doi:10.1107/S1600536809041580

. 2009 Oct 17;65(Pt 11):o2794. doi: 10.1107/S1600536809041580

c-3,t-3-Dimethyl-r-2,c-6-diphenylpiperidin-4-one

M Thenmozhi ^a, S Ponnuswamy ^b, J Umamaheshwari ^b, M Jamesh ^b, M N Ponnuswamy ^a,^*

PMCID: PMC2971408 PMID: 21578386

Abstract

In the title compound, C₁₉H₂₁NO, the piperidine ring adopts a chair conformation. The two phenyl rings attached to the piperidine ring at 2 and 6 positions occupy equatorial orientations and the dihedral angle between them is 57.53 (11)°. In the crystal, the molecules are connected via weak intermolecular C—H⋯π interactions, leading to a zigzag chains.

Related literature

For general background to piperidine derivatives, see: Badorrey et al. (1999 ▶); Nalanishi et al. (1974 ▶); Elena et al. (2002 ▶). For hybridization, see: Beddoes et al. (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶). For the synthesis of the title compound, see Noller & Baliah (1948 ▶).

Experimental

Crystal data

C₁₉H₂₁NO
M _r = 279.37
Triclinic,
a = 6.0293 (4) Å
b = 10.8198 (6) Å
c = 12.1649 (6) Å
α = 98.559 (2)°
β = 92.836 (3)°
γ = 96.677 (3)°
V = 777.62 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.986, T _max = 0.987
15310 measured reflections
3556 independent reflections
1930 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.168
S = 1.06
3556 reflections
197 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041580/bt5058sup1.cif

e-65-o2794-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041580/bt5058Isup2.hkl

e-65-o2794-Isup2.hkl^{(170.8KB, hkl)}

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
C10—H10⋯Cg3ⁱ	0.93	2.95	3.648	133

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Symmetry codes: (i) Inline graphic . Cg3 is the centroid of the C15–C20 ring.

Acknowledgments

MT thanks Dr Babu Varghese, SAIF, IIT-Madras, Chennai, India, for his help with the data collection. SP thanks the UGC, India, for financial support.

supplementary crystallographic information

Comment

Various piperidine derivatives are present in numerous alkaloids (Badorrey et al., 1999). Piperidines have been found to exhibit blood cholesterol-lowering activities (Nalanishi et al., 1974). Trans-platinum piperidine derivatives deserve evaluation of their efficacy in tumor-bearing animals (Elena et al., 2002). In view of these importance, the crystal structure of the title compound has been carrried out.

The ORTEP plot of the molecule is shown in Fig. 1. The piperidine ring adopts chair conformation and the ring-puckering parameters (Cremer & Pople, 1975) are: q₂ = 0.1578 (20)Å, q₃ = -0.5364 (21)Å, and φ = 176.7 (8)°, and the smallest asymmetry parameter Δ_s(N1)=Δ_s(C4) = 1.97 (16)° (Nardelli, 1983). The two phenyl rings attached to the piperidine ring at 2,6- positions occupy equatorial orientation [C7-C2-C3-C4 = -174.77 (16)°; C4-C5-C6-C15 = 175.09 (16)°], respectively and the dihedral angle between them is 57.52 (11)°. The methyl groups attached at position 3 of the piperidine ring takes up syn-periplanar [C13-C3-C4-O1 = -22.3 (3)°] and anti-clinical [C14-C3-C4-O1 = 97.1 (2)°] orientations. The sum of the bond angles at N1[329.62 (5)°] of the piperidine ring is in accordance with sp³ hybridization (Beddoes et al., 1986).

The molecules are connected via intermolecular C–H···π interactions (Table 1) which lead to a zig–zag chain running along b – axis in addition to van der Waals forces (Fig. 2).

Experimental

The procedure reported by Noller and Baliah was followed for the preparation of this compound (Noller & Baliah, 1948). Benzaldehyde (21ml), 3-methyl-2-butanone (10ml) and ammonium acetate (8gm) were dissolved in distilled ethanol (50ml) and heated over boiling water bath with shaking, until an yellow colour developed and changed into orange. The solution was left undisturbed for 14 hours. The solid thrown out was filtered, purified and recrystallized from ethanol.