Crystal structure of 5-(4-methyl­phen­yl)-3-[(E)-2-(4-methyl­phen­yl)ethen­yl]cyclo­hex-2-en-1-one

Joel T Mague; Shaaban K Mohamed; Mehmet Akkurt; Antar A Abdelhamid; Mustafa R Albayati

doi:10.1107/S2056989015008324

. 2015 May 7;71(Pt 6):o436–o437. doi: 10.1107/S2056989015008324

Crystal structure of 5-(4-methylphenyl)-3-[(E)-2-(4-methylphenyl)ethenyl]cyclohex-2-en-1-one

Joel T Mague ^a, Shaaban K Mohamed ^b,^c, Mehmet Akkurt ^d, Antar A Abdelhamid ^e, Mustafa R Albayati ^f,^*

PMCID: PMC4459340 PMID: 26090214

Abstract

In the title compound, C₂₂H₂₂O, the dihedral angle between the planes of the benzene rings is 53.55 (7)°. Weak C—H⋯O interactions help to direct the packing, forming sheets lying parallel to (020).

Keywords: crystal structure; cyclohexenenones; α,β-unsaturated ketones; C—H⋯O interactions

Related literature

For the synthesis of cyclohexenones and their use as synthons, see: Mayekar et al. (2010 ▸); Suwito et al. (2014 ▸); Tabba et al. (1995 ▸); Bella et al. (2012 ▸); Xing et al. (2010 ▸); Martin & Prasad (2006 ▸). For various biological activities of cyclohexenone derivatives, see: Prasad et al. (2006 ▸); Kumar et al. (2003 ▸); Tatsuzaki et al. (2006); Yun et al. (2006 ▸); Kim et al. (2008 ▸); Yoon et al. (2007 ▸); Tanaka et al. (1997 ▸); Vyas et al. (2009 ▸). For the use of cyclohexenones as intermediates in synthesis, see: Mayekar et al. (2010 ▸); Bella et al. (2012 ▸); Xing et al. (2010); Martin & Prasad (2006 ▸). For the bioactivity of dehydrozingerone, chalcone and isoeugenol derivatives, see: Tatsuzaki et al. (2006 ▸).

Experimental

Crystal data

C₂₂H₂₂O
M _r = 302.39
Monoclinic,
a = 4.9614 (1) Å
b = 30.7302 (6) Å
c = 11.0726 (2) Å
β = 93.268 (1)°
V = 1685.44 (6) Å³
Z = 4
Cu Kα radiation
μ = 0.55 mm⁻¹
T = 150 K
0.31 × 0.11 × 0.08 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T _min = 0.84, T _max = 0.96
12558 measured reflections
3247 independent reflections
2529 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.131
S = 1.05
3247 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015008324/lr2135sup1.cif

e-71-0o436-sup1.cif^{(386KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015008324/lr2135Isup2.hkl

e-71-0o436-Isup2.hkl^{(178.3KB, hkl)}

Click here for additional data file.^{(6.6KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015008324/lr2135Isup3.cml

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S2056989015008324/lr2135fig1.tif

The title molecule with labeling scheme and 50% probability ellipsoids.

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989015008324/lr2135fig2.tif

Packing viewed towards the (10 Inline graphic )plane. Weak C—H⋯O interactions are shown as dotted lines.

CCDC reference: 1062089

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

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
C6H6AO1ⁱ	0.99	2.60	3.515(2)	154
C8H8O1ⁱⁱ	0.95	2.47	3.353(2)	155
C14H14O1ⁱⁱ	0.95	2.55	3.410(2)	151

Open in a new tab

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

Acknowledgments

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

supplementary crystallographic information

S1. Structural commentary

From a chemical point of view, the most commonly used method for preparation of polyfunctionalized cyclohexenones is the Michael addition of carbanions to α,β-unsaturated ketones in presence of basic catalysts (Mayekar et al., 2010; Suwito et al., 2014; Tabba et al., 1995). Cyclohexenones have been considered as efficient synthons in building spiranic compounds (Mayekar et al., 2010) or intermediates in the synthesis of fused heterocycles such as benzoselenadiazoles and benzothiazoles (Bella et al., 2012), benzopyrazoles (Xing et al., 2010) or carbazole derivatives (Martin & Prasad, 2006). The existence of the α,β-unsaturated ketone moiety is a common feature of a large number of biologically active compounds which exhibit diverse pharmacological effects such as anti-microbial (Prasad et al., 2006), anti-tumor (Kumar et al., 2003), anti-cancer (Tatsuzaki et al., 2006; Yun et al., 2006) and radical scavenger activities (Kim et al., 2008) as well as being inhibitors of topoisomerase I (Yoon et al., 2007). Cyclohexenone derivatives, in particular, are well known lead molecules for the treatment of inflammation and autoimmune diseases (Tanaka et al., 1997). Several reports have pointed out the importance of cyclohexenones for anti-microbial and anti-tubercular activity (Vyas et al., 2009).

In the title compound (Fig. 1), the dihedral angle between the phenyl rings is 53.55 (7)°. Weak C6—H6A···O1ⁱ (i: x + 1, y, z) interactions help to direct the packing (Fig. 2 and Table 1).

S2. Synthesis and crystallization

In 30 ml of methanol, a mixture of 1 mmol (262 mg) of (1Z,4E)-1,5-bis(4-methylphenyl)penta-1,4-dien-3-one and 1 mmol (100 mg) of acetylacetone was refluxed for 5 h in the presence of 10 mg of sodium methoxide. The resulting solid product was collected, filtered under vacuum, washed with cold ethanol and recrystallized from ethanol to afford colourless columns which were suitable for X-ray diffraction. Mp. 371 K.

S3. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. H-atoms were placed in calculated positions (C—H = 0.95 - 0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms. The 020 reflection was omitted from the final refinement as it was partially obscured by the beamstop.