1-Benzoyl-c-3,t-3-dimethyl-r-2,c-6-diphenyl­piperidin-4-one

S Aravindhan; S Ponnuswamy; J Umamaheswari; P Ramesh; M N Ponnuswamy

doi:10.1107/S1600536809028037

. 2009 Jul 25;65(Pt 8):o1975. doi: 10.1107/S1600536809028037

1-Benzoyl-c-3,t-3-dimethyl-r-2,c-6-diphenylpiperidin-4-one

S Aravindhan ^a, S Ponnuswamy ^b, J Umamaheswari ^b, P Ramesh ^c, M N Ponnuswamy ^c,^*

PMCID: PMC2977502 PMID: 21583651

Abstract

In the title compound, C₂₆H₂₅NO₂, the piperidine ring adopts a distorted boat conformation. The three phenyl rings form dihedral angles of 67.58 (8), 59.82 (8) and 86.41 (8)° with the best plane through the piperidine ring. The crystal packing is governed by intermolecular C—H⋯O interactions.

Related literature

For the biological activity of piperidine derivatives, see: Dimmock et al. (2001 ▶); Perumal et al. (2001 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C₂₆H₂₅NO₂
M _r = 383.47
Monoclinic,
a = 10.8540 (9) Å
b = 17.8050 (17) Å
c = 10.8853 (10) Å
β = 94.987 (3)°
V = 2095.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.977, T _max = 0.985
27356 measured reflections
6189 independent reflections
3897 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.152
S = 0.98
6189 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.17 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/S1600536809028037/bt2990sup1.cif

e-65-o1975-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028037/bt2990Isup2.hkl

e-65-o1975-Isup2.hkl^{(296.8KB, 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
C6—H6⋯O1	0.98	2.29	2.7346 (17)	106
C2—H2⋯O1ⁱ	0.98	2.56	3.3784 (17)	141
C20—H20A⋯O1ⁱ	0.96	2.47	3.1885 (19)	132
C20—H20B⋯O2ⁱⁱ	0.96	2.52	3.470 (2)	170

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

SA thanks Dr Babu Varghese, SAIF, IIT–Madras, India, for his help with the data collection.

supplementary crystallographic information

Comment

Piperidones are the important group of heterocyclic compounds in the field of medicinal chemistry due to their biological activities, including cytotoxic and anticancer properties (Dimmock et al., 2001). They were also reported to possess analgesic, anti-inflammatory, central nervous system (CNS), local anaesthetic, anticancer and antimicrobial activities (Perumal et al., 2001). In view of these importance and to ascertain the molecular conformation, crystallographic study of the title compound has been carried out.

The ORTEP diagram of the title compound is shown in Fig.1. The piperidine ring adopts distorted boat conformation. The puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) for this ring are q₂ = 0.636 (2) Å, q₃ = 0.104 (2) Å, π = 282.8 (1)° and Δs(C3) =Δs(C6)= 18.6 (1)°. The sum of the angles at N1 (359.7°) is in accrdance with sp² hybridization. The three phenyl rings are twisted away from the best plane of the pyridine ring by 67.58 (8)°, 59.82 (8)° and 86.41 (8)° respectively.

The crystal packing is controlled by C—H···O types of intra and intermolecular interactions in addition to van der Waals forces. Atom C2 at (x, y, z) donates a proton to O1 x, -y + 1/2, z + 1/2, which forms a C(5) (Bernstein, et al., 1995) zigzag chain running along c axis. The combination of C20—H20A···O1 and C20—H20B···O2 intermolecular interactions forms a dimer chain running along c axis shown in Fig. 2.

Experimental

A mixture of c-3,t-3-dimethyl-r-2,c-6-diphenylpiperidin-4-one (1.4 g, 5 mmol), benzoyl chloride (1.2 ml, 10 mmol) and triethylamine (2 ml, 14.4 mmol) in anhydrous benzene (20 ml) was stirred at room temperature for 7 h. The precipitated ammonium salt was washed with water (4x10ml). The resulting pasty mass was purified and crystallized from benzene and pet-ether (60–80°C) in the ratio of 95: 5.