(3E,5E)-3,5-Bis(4-methyl­benzyl­idene)-1-[3-(piperidin-1-yl)propano­yl]piperidin-4-one

Yalda Kia; Hasnah Osman; Vikneswaran Murugaiyah; Suhana Arshad; Ibrahim Abdul Razak

doi:10.1107/S1600536812031820

. 2012 Jul 18;68(Pt 8):o2493–o2494. doi: 10.1107/S1600536812031820

(3E,5E)-3,5-Bis(4-methylbenzylidene)-1-[3-(piperidin-1-yl)propanoyl]piperidin-4-one

Yalda Kia ^a, Hasnah Osman ^a,^‡, Vikneswaran Murugaiyah ^b, Suhana Arshad ^c, Ibrahim Abdul Razak ^c,^*,^§

PMCID: PMC3414948 PMID: 22904935

Abstract

In the title compound, C₂₉H₃₄N₂O₂, the central piperidine ring adopts a half-chair conformation, whereas the terminal one adopts a chair conformation. The mean plane of the central piperidine ring [maximum deviation = 0.384 (2) Å] makes dihedral angles of 64.82 (13) and 17.55 (13)° with the benzene rings. In the crystal, molecules are linked into a tape along the b axis via C—H⋯O interactions, generating R ₂ ²(20) and R ₂ ¹(6) graph-set motifs. C—H⋯π interactions are observed between the tapes.

Related literature

For biological activities of α,β-unsaturated ketones, see: Tanaka et al. (2003 ▶); Nakayachi et al. (2004 ▶); Lee et al. (2004 ▶); Hertzberg et al. (1989 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For related structures, see: Aridoss et al. (2010 ▶); Kia et al. (2011 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶). For the preparation of 1-acryloyl-3,5-dibenzylidenepiperidin-4-one, see: Dimmock et al. (2001 ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₉H₃₄N₂O₂
M _r = 442.58
Monoclinic,
a = 12.2913 (8) Å
b = 9.9753 (8) Å
c = 19.9993 (14) Å
β = 100.884 (4)°
V = 2408.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.46 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.966, T _max = 0.985
18968 measured reflections
6852 independent reflections
3483 reflections with I > I > 2σ(I)
R _int = 0.075

Refinement

R[F ² > 2σ(F ²)] = 0.078
wR(F ²) = 0.228
S = 1.04
6852 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.37 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/S1600536812031820/is5165sup1.cif

e-68-o2493-sup1.cif^{(33.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031820/is5165Isup2.hkl

e-68-o2493-Isup2.hkl^{(335.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812031820/is5165Isup3.cml

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

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

Cg1 is the centroid of the benzene C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O2ⁱ	0.95	2.51	3.346 (3)	147
C21—H21A⋯O2ⁱ	0.98	2.44	3.371 (4)	160
C21—H21C⋯O1ⁱⁱ	0.98	2.52	3.446 (3)	157
C4—H4A⋯Cg1ⁱⁱⁱ	0.95	2.69	3.526 (3)	148
C27—H27A⋯Cg1^iv	0.99	2.74	3.719 (3)	168

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

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for an FRGS grant (No. 203/PKIMIA/6711179) and an RU grant (No. 1001/PFIZIK/811151) to conduct this work. YK thanks USM for providing research facility. SA thanks the Malaysian Government and USM for an Academic Staff Training Scheme Fellowship.

supplementary crystallographic information

Comment

Claisen-Schmidt condensation reaction between aldehyde and ketone, leads to biological active class of compound, namely α,β-unsaturated ketones. These compounds show a wide range of biological activities such as enzyme inhibitory (Tanaka et al., 2003), cytotoxic and antitumor (Nakayachi et al., 2004). This conjugated system, O═CH—CH═CH₂ is the key moiety which promotes the bioactivities in the title compound (Lee et al., 2004). α, β-unsaturated ketones can be considered as a Michael acceptor which is an active moiety showing enzyme inhibitory activity (Hertzberg et al., 1989). Due to these reasons, the crystal structure determination of the title compound was carried out and the results are presented in this paper.

The molecular structure is shown in Fig. 1. The bond lengths and angles are within normal ranges and comparable to the related structures (Aridoss et al., 2010; Kia et al., 2011). The piperidine rings (N1/C8–C12 and N2/C25–C29) adopt different conformations (Cremer & Pople, 1975). N1/C8–C12 adopts a half-chair conformation [puckering parameters, Q= 0.556 (3) Å, Θ= 117.4 (3)° and Φ= 157.4 (3)°], whereas, N2/C25–C29 adopts a chair conformation [puckering parameters, Q= 0.573 (3) Å, Θ= 3.3 (3)° and Φ= 329 (5)°]. The least square plane through both rings form a dihedral angle of 18.29 (13)° between them. The least-square plane of the central piperidine ring [N1/C8–C12, maximum deviation of 0.384 (2) Å at atom N1] forms dihedral angles of 64.82 (13) and 17.55 (13)°, respectively, with the pendant benzene rings (C1–C6 and C14–C19).

In the crystal packing (Fig. 2), molecules are linked into a tape along the b axis via intermolecular C16—H16A···O2, C21—H21A···O2 and C21—H21C···O1 interactions (Table 1), generating R²₂(20) and R¹₂(6) graph-set motifs (Bernstein et al., 1995). The crystal structure is further stabilized by the intermolecular C4—H4A···Cg1 and C27—H27A···Cg1 (Table 1) interactions (Cg1 is the centroid of the benzene ring, C14–C19).

Experimental

1-Acryloyl-3,5-dibenzylidenepiperidin-4-one was synthesized as reported in the literature (Dimmock et al., 2001). The title compound was prepared by refluxing 1-acryloyl-3,5-dibenzylidenepiperidin-4-one (0.6 mmol) with piperidine (0.6 mmol) in ethanol. After completion of the reaction as evident from TLC, the mixture was poured into ice. The precipitated solid was filtered and washed with water. The pure solid was then recrystallized from ethanol to afford the title compound as yellow crystals.