Crystal structure of 2-chloro-1-(3-ethyl-2,6-di­phenyl­piperidin-1-yl)ethanone

V Shreevidhyaa Suressh; B K Revathi; S Abdul Basheer; S Ponnuswamy; G Usha

doi:10.1107/S2056989015000444

. 2015 Jan 21;71(Pt 2):o122. doi: 10.1107/S2056989015000444

Crystal structure of 2-chloro-1-(3-ethyl-2,6-diphenylpiperidin-1-yl)ethanone

V Shreevidhyaa Suressh ^a, B K Revathi ^b, S Abdul Basheer ^c, S Ponnuswamy ^c, G Usha ^b,^*

PMCID: PMC4384592 PMID: 25878863

Abstract

In the racemic title compound, C₂₁H₂₄ClNO, the dihedral angle between the planes of the benzene rings is 86.52 (14)° and those between the benzene rings and the piperidine ring are 61.66 (14) and 86.39 (14)°. The piperidine ring adopts a twisted boat conformation. No directional interactions could be detected in the crystal.

Keywords: crystal structure; 2-chloro-1-(3-ethyl-2,6-diphenylpiperidin-1-yl)ethanone; biological activity; piperidine derivative

Related literature

For the biological activity of piperidine derivatives, see: Nalanishi et al. (1974 ▸); Robinson (1973 ▸); Mobio et al. (1989 ▸); Parthiban et al. (2009 ▸).

Experimental

Crystal data

C₂₁H₂₄ClNO
M _r = 341.86
Monoclinic,
a = 8.5971 (9) Å
b = 12.9080 (13) Å
c = 17.1114 (16) Å
β = 100.501 (5)°
V = 1867.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.25 × 0.23 × 0.23 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T _min = 0.949, T _max = 0.953
17549 measured reflections
4639 independent reflections
2930 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.226
S = 1.01
4639 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.43 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 ▸, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015000444/zs2323sup1.cif

e-71-0o122-sup1.cif^{(26.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015000444/zs2323Isup2.hkl

e-71-0o122-Isup2.hkl^{(219.3KB, hkl)}

Click here for additional data file.^{(6.8KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015000444/zs2323Isup3.cml

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S2056989015000444/zs2323fig1.tif

The molecular structure of the title compound showing atom numbering, with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.^{(1.8MB, tif)}

. DOI: 10.1107/S2056989015000444/zs2323fig2.tif

The packing of the molecules in the unit cell.

CCDC reference: 1042840

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection facilities.

supplementary crystallographic information

S1. Comment

Piperidine derivatives have immense biological significance and show blood cholesterol lowering activity (Nalanishi et al., 1974; Parthiban et al., 2009). The piperidine moiety is the basic unit commonly found in natural alkaloids. These compounds are observed to exhibit antihistamine, anaesthetic and tranquilizer activities (Robinson, 1973). They also exhibit antifungal and antibacterial activities (Mobio et al., 1989).

In the stucture of the racemic title compound, C₂₁H₂₄ClNO (Fig. 1) the C—C bond lengths and bond angles are in the normal range and comparable with the literature values. The sum of the bond angles around the nitrogen atom N1 is 359.54 (1)° which indicates sp² hybridization. The benzene ring C4/C5/C6/C7/C8/C9 is bisectionally [59.92 (2)°] attached to the piperidine ring and the benzene ring C14/C15/C16/C17/C18/C19 is axiallly [9.27 (2)°] attached to the piperidine ring. The dihedral angle between the benzene rings is 86.52 (14)° and those between the benzene rings and the piperidine ring are 61.66 (14) and 86.39 (14)°, respectively. The symmetric bond angles [C11—C12—C20 = 107.4 (3) Å and C20—C12—C13 = 110.3 (2) Å] indicate that the ethyl group is coplanar with the piperidine ring. The piperidine ring adopts a twisted boat conformation with puckering parameters of q2 = 0.691 (3) Å, θ2 = 94.4 (2)°, q3 = -0.053 (3) Å, QT = 0.693 (3) Å and smallest asymmetry parameter D2(C3) (Nardelli, 1983) is 0.1078 (1) Å. In the crystal there are no formal hydrogen bonds or inter-ring π–π interactions present (Fig. 2).

S2. Experimental

A mixture of t-3-methyl-r-2,c-6-diphenylpiperidine (5 mmol), chloroacetyl chloride (20 mmol) and triethylamine (20 mmol) in anhydrous benzene (20 ml) was stirred at room temperature. The precipitated ammonium salt was filtered and the resulting solution was washed with water and bicarbonate solution (4x10 ml). Finally, the benzene solution was dried over anhydrous sodium sulphate and concentrated. The pasty mass was purified by crystallization from a mixture of petroleum ether (60–80 °C) and ethyl acetate in the ratio of 95:5.