1-Chloro­acetyl-3-isopropyl-r-2,c-6-diphenyl­piperidin-4-one

K Ravichandran; P Ramesh; P Jeganathan; S Ponnuswamy; M N Ponnuswamy

doi:10.1107/S160053680905497X

. 2010 Jan 9;66(Pt 2):o276–o277. doi: 10.1107/S160053680905497X

1-Chloroacetyl-3-isopropyl-r-2,c-6-diphenylpiperidin-4-one

K Ravichandran ^a, P Ramesh ^a, P Jeganathan ^b, S Ponnuswamy ^b, M N Ponnuswamy ^a,^*

PMCID: PMC2979709 PMID: 21579713

Abstract

In the title compound, C₂₂H₂₄ClNO₂, the piperidine ring adopts a distorted boat conformation. The dihedral angle between the two phenyl rings is 83.2 (1)°. In the crystal, the molecules are linked into chains running along the b axis by C—H⋯O hydrogen bonds. The Cl atom of the chloroacetyl group is disordered over two positions with occupancies of 0.66 (2) and 0.34 (2).

Related literature

For general background to piperidine derivatives, see: El-Subbagh et al. (2000 ▶); Jerom & Spencer (1988 ▶); Perumal et al. (2001 ▶); Hagenbach & Gysin (1952 ▶); Mobio et al. (1989 ▶); Katritzky & Fan (1990 ▶); Ganellin & Spickett (1965 ▶). For asymmetry and puckering parameters, see: Nardelli (1983 ▶); Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the synthesis, see: Venkatraj et al. (2008 ▶).

Experimental

Crystal data

C₂₂H₂₄ClNO₂
M _r = 369.87
Monoclinic,
a = 10.3415 (12) Å
b = 9.0243 (9) Å
c = 21.438 (2) Å
β = 90.894 (3)°
V = 2000.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.23 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.954, T _max = 0.960
19037 measured reflections
4965 independent reflections
3634 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.152
S = 1.05
4965 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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/S160053680905497X/ci2993sup1.cif

e-66-0o276-sup1.cif^{(22.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905497X/ci2993Isup2.hkl

e-66-0o276-Isup2.hkl^{(238.3KB, 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⋯O1ⁱ	0.98	2.57	3.504 (2)	160
C8—H8C⋯O1ⁱ	0.96	2.25	3.203 (2)	174

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Symmetry code: (i) Inline graphic .

Acknowledgments

KR thanks the GNR X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the management of Kandaswami Kandar’s College, Velur, Namakkal, Tamil Nadu, India, for the encouragement to pursue the programme.

supplementary crystallographic information

Comment

Piperidine derivatives gained considerable importance owing to their varied biological properties such as antiviral, antitumour (El-Subbagh et al., 2000), analgesic (Jerom & Spencer, 1988), local anaesthetic (Perumal et al., 2001; Hagenbach & Gysin, 1952), antimicrobial, bactericidal, fungicidal, herbicidal, insecticidal, antihistaminic, anti-inflammatory, anticancer, CNS stimulant and depressant activities (Mobio et al., 1989; Katritzky & Fan, 1990; Ganellin & Spickett, 1965). In view of these importance and to ascertain the molecular conformation, crystallographic study of the title compound has been carried out.

The ORTEP plot of the title molecule is shown in Fig.1. The piperidine ring adopts a distorted boat conformation with the puckering parameters (Cremer & Pople, 1975) and asymmetry parameters (Nardelli, 1983) of q₂ = 0.661 (2) Å, q₃ = -0.057 (2) Å, φ₂ = 257.1 (1)° and Δ_s(C2 and C5)= 20.2 (2)°. The sum of the bond angles around the atom N1 (358.8°) of the piperidine ring is in accordance with the sp² hybridization.

The crystal packing is stabilized by C—H···O intermolecular interactions which link the molecules into chains running along the b axis. These hydrogen bonds form R¹₂(7) ring motifs (Bernstein et al., 1995).

Experimental

To a solution of r-2,c-6-diphenyl-3-isopropylpiperidin-4-one (2.93 g) in anhydrous benzene (60 ml) was added triethylamine (5.57 ml) and chloroacetylchloride (3.18 ml). The reaction mixture was allowed to stirr at room temperature for 2 h. The resulting solution was washed with sodium bicarbonate solution (10%) and water. Then the organic layer was dried over anhydrous sodium sulfate, evaporated and crystallized from benzene-petroleum ether (60–80°C) in the ratio of 9:1 (Venkatraj et al., 2008).