1-Benzyl-3,5-bis­(4-methyl­benzyl­idene)-4-oxopiperidin-1-ium chloride acetic acid monosolvate

Ju-feng Sun; Juan Xing; Jing-tian Han

doi:10.1107/S1600536811016138

. 2011 May 7;67(Pt 6):o1350. doi: 10.1107/S1600536811016138

1-Benzyl-3,5-bis(4-methylbenzylidene)-4-oxopiperidin-1-ium chloride acetic acid monosolvate

Ju-feng Sun ^a,^*, Juan Xing ^a, Jing-tian Han ^a

PMCID: PMC3120477 PMID: 21754744

Abstract

In the title solvated molecular salt, C₂₈H₂₈NO⁺·Cl⁻·C₂H₄O₂, the central piperidinium ring of the cation adopts an envelope conformation with the N atom displaced by 0.798 (2) Å from the mean plane of the five C atoms. In the crystal, the components are linked by N—H⋯Cl and O—H⋯Cl hydrogen bonds into trimeric assemblies. C—H⋯Cl and C—H⋯π interactions further consolidate the packing.

Related literature

For background to the use of piperidone derivatives in medicine, see: Dimmock et al. (2003 ▶); El-Subbagh et al. (2000 ▶); Pati et al. (2009 ▶); Das et al. (2009 ▶, 2010 ▶). For the synthesis, see: Pati et al. (2009 ▶).

Experimental

Crystal data

C₂₈H₂₈NO⁺·Cl⁻·C₂H₄O₂
M _r = 490.02
Triclinic,
a = 7.1488 (5) Å
b = 11.2799 (7) Å
c = 17.6271 (11) Å
α = 103.181 (6)°
β = 98.087 (6)°
γ = 92.407 (6)°
V = 1366.16 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 288 K
0.61 × 0.54 × 0.52 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.804, T _max = 1.000
16829 measured reflections
5549 independent reflections
3895 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.158
S = 1.03
5549 reflections
320 parameters
39 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016138/hb5860sup1.cif

e-67-o1350-sup1.cif^{(23.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016138/hb5860Isup2.hkl

e-67-o1350-Isup2.hkl^{(271.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811016138/hb5860Isup3.cml

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

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

Cg3 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1	0.91	2.15	3.0490 (17)	171
O3—H3⋯Cl1	0.82	2.26	3.053 (2)	162
C11—H11A⋯Cl1ⁱ	0.97	2.72	3.602 (2)	151
C25—H25⋯Cg3ⁱⁱ	0.93	2.85	3.582 (4)	137
C30—H30C⋯Cg3ⁱⁱⁱ	0.97	2.96	3.675 (4)	133

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

Acknowledgments

The authors are grateful to Binzhou Medical College for financial support.

supplementary crystallographic information

Comment

At present, a series of N-substituted-3,5-bis(arylidene)-4-piperidone derivatives have been synthesized and proved to be a kind of lead tumor-specific cytotoxin which induces apoptosis and autophagy with multidrug-resistance reverting properties (Pati et al. 2009; Das et al. 2009; Das et al. 2010). These compounds have a marked affinity for thiols in contrast to amino and hydroxyl groups found in nucleic acids (Dimmock et al. 2003). Thus development of these compounds as candidate cytotoxics may lead to drugs which are lack of the genotoxic properties present in various antineoplastic agents (El-Subbagh et al. 2000). Here, we report the title compound (I), whose IC₅₀ (µM) to HL-60 and HSC-2 cells are 59.80 and 105.09 could be used as a basic unit to prepare antineoplastic compounds.

The molecular structure of the title compound (I) is shown in Fig. 1. The hydrogen proton of hydrogen chloride have completely transferred to N1, resulting in the formation of ammonium salt, in which the hydrogen-bonding donors and acceptors reside separately on the cations and anions. In the crystal, weak intermolecular N—H···Cl hydrogen bonds, C—H···Cl hydrogen bonds, O—H···Cl hydrogen bonds and C—H···π stacking interactions contribute to the crystal packing arrangement (Table 1).

Experimental

The title compound was synthesized according to the literature (Pati et al. 2009). Dry hydrogen chloride was continuously bubbled into a solution of N-benzyl-4-piperidone (0.005 mol) and p-tolualdehyde (0.01 mol) in acetic acid (15 ml) at room temperature. And then the mixture was stirred at room temperature for 12 h. When the produced precipitate was collected, they were added to a solution of aqueous potassium carbonate solution (25%, w/v). The desired product was obtained after the solid was crystallized by the mixed solvents of ethanol and chloroform (5:1, v/v) in a yield of 74.8%. Yellow blocks of (I) were obtained by slow evaporation of the reacting solution of the title compound in acetic acid.