5-(4-Methyl­phen­yl)-3-phenyl­cyclo­hex-2-en-1-one

Shaaban K Mohamed; Mehmet Akkurt; Antar A Abdelhamid; Kuldip Singh; Omyma A A Abd Allah

doi:10.1107/S1600536812027031

. 2012 Jun 20;68(Pt 7):o2157. doi: 10.1107/S1600536812027031

5-(4-Methylphenyl)-3-phenylcyclohex-2-en-1-one

Shaaban K Mohamed ^a, Mehmet Akkurt ^b,^*, Antar A Abdelhamid ^a, Kuldip Singh ^c, Omyma A A Abd Allah ^d

PMCID: PMC3393964 PMID: 22798829

Abstract

In the title compound, C₁₉H₁₈O, the cyclohexene ring has an envelope conformation with the methine C atom on the flap. The phenyl and methylphenyl rings form a dihedral angle of 85.93 (11)°. The crystal packing is consolidated by van der Waals forces and weak C—H⋯π interactions.

Related literature

For the biological activity of α,β-unsaturated carbonyl compounds, see: Podraze (1991 ▶); Suksamrarn et al. (2003 ▶); Modzelewska et al. (2006 ▶); Shettigar et al. (2006 ▶); Ferrer et al. (2009 ▶); Asiri (2003 ▶); Forestier et al. (1989 ▶); Kumar et al. (2003 ▶). For the synthesis of cyclohexenones, see: Diao & Stahl (2011 ▶); González et al. (2009 ▶); Zhang et al. (2008 ▶). For geometric analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₉H₁₈O
M _r = 262.33
Monoclinic,
a = 17.085 (4) Å
b = 5.6807 (11) Å
c = 15.689 (3) Å
β = 113.152 (4)°
V = 1400.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 150 K
0.42 × 0.24 × 0.12 mm

Data collection

Bruker APEX 2000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.979, T _max = 0.991
9636 measured reflections
2473 independent reflections
1497 reflections with I > 2σ(I)
R _int = 0.106

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.114
S = 0.90
2473 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027031/xu5565sup1.cif

e-68-o2157-sup1.cif^{(23.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027031/xu5565Isup2.hkl

e-68-o2157-Isup2.hkl^{(121.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812027031/xu5565Isup3.cml

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

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

Cg is the centroid of the C13–C18 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cg ⁱ	0.95	2.77	3.601 (3)	147

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the Higher Education Ministry of Egypt for financial support and also thank Manchester Metropolitan University, Erciyes University and the University of Leicester for supporting this study.

supplementary crystallographic information

Comment

α,β-Unsaturated carbonyl compounds have shown various biological activities such as antioxidant (Suksamrarn et al., 2003), antitumor (Kumar et al., 2003), anticancer (Modzelewska et al., 2006) and antimalarial (Ferrer et al., 2009). In addition, chalcones also were widely used in cosmetic compositions (Forestier et al., 1989; Podraze, 1991) and applications of dyes (Asiri, 2003). Apart from being biologically important compounds, chalcone derivatives show non-linear optical (NLO) properties with excellent blue light transmittance and good crystallizability (Shettigar et al., 2006). In this context, herein we report the synthesis and crystal structure of the title compound (I).

As seen in Fig. 1, the title compound is not planar. The C1–C6 cyclohexene ring in (I) has a nearly envelope conformation [puckering parameters (Cremer & Pople, 1975) Q_T = 0.511 (3) Å, θ = 53.4 (3) ° and φ = 247.6 (4) °]. The C7–C12 phenyl ring makes a dihedral angle of 85.93 (11)° with the methyl-substituted C13 C18 benzene ring.

The crystal packing of (I) is stabilized by van der Waals forces and weak C—H···π interactions (Table 1, Fig. 2).

Experimental

To a solution of 222 mg (1 mmol) (2E)-3-(4-methylphenyl)-1-phenylprop-2-en-1-one in 40 ml e thanol, 100 mg of acetyl acetone was added in presence of 60 mg MeONa. The reaction mixture was refluxed for 7 h then cooled to room temperature (Diao & Stahl, 2011; González et al., 2009; Zhang et al., 2008). The excess solvent was removed under vacuum to afford the solid product which was filltered off and recrystallized from ethanol. The obtained crystals were in good quality (m.p. 343 K) for X-ray diffraction without further crystallization.