1-Benzoyl-3-methyl-2,6-diphenyl-4-piperidone

P Nithya; Venkatesha R Hathwar; Sriramakrishnaswamy Kone; N Malathi; F Nawaz Khan

doi:10.1107/S1600536809023848

. 2009 Jun 27;65(Pt 7):o1692–o1693. doi: 10.1107/S1600536809023848

1-Benzoyl-3-methyl-2,6-diphenyl-4-piperidone

P Nithya ^a, Venkatesha R Hathwar ^b, Sriramakrishnaswamy Kone ^a, N Malathi ^a, F Nawaz Khan ^a,^*

PMCID: PMC2969294 PMID: 21582948

Abstract

In the title moleclue, C₂₅H₂₃NO₂, the 4-piperidone ring adopts a boat conformation. The molecular conformation is stabilized by an intramolecular C—H⋯O hydrogen bond. In the crystal, molecules are connected through weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For general background, see: Grishina et al. (1994 ▶); Nalanishi et al. (1974 ▶); Perumal et al. (2001 ▶); Ponnuswamy et al. (2002 ▶). For related structures, see: Gayathri et al. (2008 ▶); Nithya et al. (2009 ▶). For details of the synthesis, see: Noller & Baliah (1948 ▶).

Experimental

Crystal data

C₂₅H₂₃NO₂
M _r = 369.44
Monoclinic,
a = 11.7602 (6) Å
b = 9.2404 (3) Å
c = 19.1722 (9) Å
β = 98.797 (4)°
V = 2058.93 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 290 K
0.36 × 0.24 × 0.18 mm

Data collection

Oxford Xcalibur Eos(Nova) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.942, T _max = 0.987
22931 measured reflections
3831 independent reflections
2515 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.105
S = 1.00
3831 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023848/bt2975sup1.cif

e-65-o1692-sup1.cif^{(22.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023848/bt2975Isup2.hkl

e-65-o1692-Isup2.hkl^{(184KB, 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
C8—H8⋯O1	0.98	2.26	2.7235 (17)	108
C9—H9A⋯O1ⁱ	0.97	2.56	3.4446 (19)	152

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Department of Science and Technology, India for the use of the CCD facility setup under the FIST–DST program at SSCU, IISc. We thank Prof T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding.

supplementary crystallographic information

Comment

4-piperidones and their derivatives present potential medical applications (Grishina et al., 1994, Ponnuswamy et al., 2002, Nalanishi et al., 1974). Piperidones are also reported to possess analgesic,anti-inflammatory, central nervous system (CNS), local anaesthetic, anticancer and antimicrobial activity (Perumal et al., 2001). In continouus of our interest in piperidones (Nithya et al., 2009), the crystal structure of title compound is discussed in this paper.

In the title molecule, C₂₅H₂₃NO₂ (Fig. 1), the piperidine ring adopts a boat conformation. In the related crystal structure, the piperidine ring also adopts a chair conformation (Gayathri et al., 2008) but the three substituents on the C atoms of the ring are in axial orientations. In the crystal, the molecules are connected through weak intermolecular C—H···O hydrogen bonds. (Fig. 2).

Experimental

To a well stirred solution of 3 methyl-2,6-bis(phenyl)piperidin-4-one (1 equiv.) and triethylamine (1 equiv.) in freshly distilled benzene, benzoyl chloride (1 equiv.) in benzene was added dropwise. Stirring was continued until the completion of reaction. Later, it was poured into water and extracted with DCM, washed well with sodium bicarbonate solution and dried over anhydrous sodium sulfate. This upon evaporation and subsequent recrystallization in distilled ethanol furnished the diffraction-quality crystals of the title compound.