3-Methyl-5-(4-methyl­phen­yl)cyclo­hex-2-enone

R T Sabapathy Mohan; S Kamatchi; M Subramanyam; A Thiruvalluvar; A Linden

doi:10.1107/S1600536808013822

. 2008 May 14;64(Pt 6):o1066. doi: 10.1107/S1600536808013822

3-Methyl-5-(4-methylphenyl)cyclohex-2-enone

R T Sabapathy Mohan ^a, S Kamatchi ^a, M Subramanyam ^b, A Thiruvalluvar ^b,^*, A Linden ^c

PMCID: PMC2961522 PMID: 21202585

Abstract

In the title molecule, C₁₄H₁₆O, the cyclohexene ring adopts an envelope conformation, with all substituents equatorial. Molecules are linked by C—H⋯O hydrogen bonds. A C—H⋯π interaction involving the benzene ring is also found in the crystal structure. The H atoms of both methyl groups are disordered equally over two positions.

Related literature

For related literature, see: Padmavathi et al. (2000 ▶).

Experimental

Crystal data

C₁₄H₁₆O
M _r = 200.27
Monoclinic,
a = 5.2623 (3) Å
b = 11.1583 (7) Å
c = 19.3341 (11) Å
β = 94.994 (4)°
V = 1130.96 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 160 (1) K
0.25 × 0.18 × 0.18 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: none
16716 measured reflections
2002 independent reflections
1316 reflections with I > 2σ(I)
R _int = 0.085

Refinement

R[F ² > 2σ(F ²)] = 0.072
wR(F ²) = 0.231
S = 1.09
2002 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013822/wn2260sup1.cif

e-64-o1066-sup1.cif^{(21.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013822/wn2260Isup2.hkl

e-64-o1066-Isup2.hkl^{(96.5KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.95	2.48	3.425 (3)	173
C5—H5⋯Cgⁱⁱ	1.00	2.94	3.818 (3)	147

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) . Cg is the centroid of the bezene ring.

Acknowledgments

AT thanks the UGC, India, for the award of a Minor Research Project [File No. MRP-2355/06(UGC-SERO), Link No. 2355, 10/01/2007].

supplementary crystallographic information

Comment

The title compound, has been analysed as part of our crystallographic studies on substituted cyclohexenes. The molecular structure of the title compound, with atomic numbering scheme, is shown in Fig. 1. The cyclohexene ring adopts an envelope conformation, with all substituents equatorial. Molecules are linked by C2—H2···O1(2 - x, 1 - y, 1 - z) hydrogen bonds (Fig. 2). A C—H···π interaction involving the benzene ring is also found in the crystal structure.

Experimental

The title compound was prepared according to the general procedure reported by Padmavathi et al. (2000). A mixture of 2,4-bis(ethoxycarbonyl)-5-hydroxy-5-methyl-3,4'-methylphenylcyclohexanone (3.62 g, 0.01 mol) in glacial acetic acid (25 ml) and concentrated hydrochloric acid (50 ml) was refluxed for 12 h. After completion of the reaction, the reaction mixture was neutralized with aqueous ammonia and separated using chloroform. The product was purified by column chromatography (benzene-EtOAc, 9.5:0.5 v/v). The yield of the isolated product was 1.07 g (87%).