(3E,5E)-3,5-Dibenzyl­idene-1-phenethyl­piperidin-4-one

Mohamed Ashraf Ali; Tan Soo Choon; Abdulrahman I Almansour; Tara Shahani; Hoong-Kun Fun

doi:10.1107/S1600536811035744

. 2011 Sep 14;67(Pt 10):o2605. doi: 10.1107/S1600536811035744

(3E,5E)-3,5-Dibenzylidene-1-phenethylpiperidin-4-one

Mohamed Ashraf Ali ^a, Tan Soo Choon ^b, Abdulrahman I Almansour ^c, Tara Shahani ^d, Hoong-Kun Fun ^d,^*,^‡

PMCID: PMC3201386 PMID: 22058753

Abstract

In the title compound, C₂₇H₂₅NO, the piperidine ring adopts an envelope conformation with the N atom at the flap position. The two benzylidene-benzene rings are oriented at a dihedral angle of 8.5 (1)°. In the crystal, the molecules are linked into centrosymmetric dimers by pairs of intermolecular C—H⋯O hydrogen bonds. The dimers are connected via C—H⋯π interactions involving the phenyl rings.

Related literature

For the biological activity of piperidine compounds, see: Asano et al. (2000 ▶); Scriabine (1980 ▶); Watson et al. (2000 ▶); Risi (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₇H₂₅NO
M _r = 379.48
Monoclinic,
a = 11.4785 (2) Å
b = 5.8396 (1) Å
c = 30.9591 (5) Å
β = 106.412 (1)°
V = 1990.63 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.36 × 0.30 × 0.11 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.973, T _max = 0.992
21942 measured reflections
5877 independent reflections
4370 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.070
wR(F ²) = 0.173
S = 1.08
5877 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035744/ci5200sup1.cif

e-67-o2605-sup1.cif^{(22.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035744/ci5200Isup2.hkl

e-67-o2605-Isup2.hkl^{(287.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811035744/ci5200Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1, Cg2 and Cg3 are centroids of the C1–C6, C14–C19 and C22–C27 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1ⁱ	0.95	2.54	3.425 (3)	155
C15—H15A⋯O1ⁱ	0.95	2.49	3.345 (3)	150
C2—H2A⋯Cg3ⁱⁱ	0.95	2.88	3.579 (2)	131
C23—H23A⋯Cg1ⁱⁱⁱ	0.95	2.99	3.640 (2)	127
C26—H26A⋯Cg2^iv	0.95	2.89	3.556 (2)	128

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

Acknowledgments

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSH also thanks USM for the award of a research fellowship.

supplementary crystallographic information

Comment

Piperidines are very important compounds because of their presence in numerous alkaloids, pharmaceuticals, agrochemical and as synthetic intermediates. Biologically active alkaloids of the substituted piperidine ring system have been targeted for their total or partial synthesis. During a fairly recent 10-year period, several thousand piperidine compounds have been mentioned in clinical and preclinical studies (Watson et al., 2000). Selective inhibition of a number of enzymes involved in the binding and processing of glycoproteins has rendered piperidine alkaloids as important tools in the study of biochemical pathways (Asano et al., 2000). Piperidine derivatives are found to possess pharmacological activity and form an essential part of the molecular structures of important drugs such as raloxifene and minoxidil (Risi, 2008). A new neuroleptics has found that the piperidine derivatives have high affinity for CNS (Scriabine, 1980).

In the title compound (Fig. 1), the piperidine (N1/C8–C12) ring is attached to three benzene (C1–C6), (C14–C19) and (C22–C27) rings via butane (C6–C8) and prop-1-ene (C20–C22) groups. The piperidine ring adopts an envelope conformation (Cremer & Pople, 1975) with puckering parameters of Q = 0.556 (2) Å, Θ = 60.3 (2)° and φ = 357.5 (2)°. Atom N1 deviates from the C8-C12 plane by 0.738 (2) Å. The two benzyl phenyl rings are oriented at a dihedral angle of 8.5 (1)°. The bond lengths (Allen et al.,1987) and angles are within normal ranges.

In the crystal structure (Fig. 2), intermolecular C15—H15A···O1 and C13—H13A···O1 hydrogen bonds link the molecules into centrosymmetric dimers each containing two R¹₂(6) ring motifs. In addition, the crystal structure is stabilized by C—H···π interactions (Table 1).

Experimental

A mixture of 1-phenethyl-4-piperonidone (0.001 mmol) and benzaldehyde (0.002 mmol) were dissolved in methanol (10 ml) and 30% sodium hydroxide solution (5 ml) was added. The mixture was stirred for 5 h. After completion of the reaction as evident from TLC, the mixture was poured into crushed ice and then was neutralized with conentrated HCl. The precipitated solid was filtered, washed with water and recrystallized from ethanol to obtain the title compound as light yellow crystals.