1-Methyl-5-(4-methyl­phen­yl)-3-oxo­cyclo­hexane-1-carbonitrile

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

doi:10.1107/S1600536808009070

. 2008 Apr 10;64(Pt 5):o818. doi: 10.1107/S1600536808009070

1-Methyl-5-(4-methylphenyl)-3-oxocyclohexane-1-carbonitrile

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

PMCID: PMC2961276 PMID: 21202308

Abstract

In the title molecule, C₁₅H₁₇NO, the cyclohexane ring adopts a chair conformation. The cyano and methyl groups at position 1 have axial and equatorial orientations, respectively. The benzene ring has an equatorial orientation. A C—H⋯π interaction involving the benzene ring is found in the crystal structure.

Related literature

Subramanyam et al. (2007 ▶) have reported the crystal structure of 3-cyano-3-methyl-5-phenylcyclohexane, in which the cyclohexane ring adopts a chair conformation.

Experimental

Crystal data

C₁₅H₁₇NO
M _r = 227.30
Monoclinic,
a = 23.4475 (5) Å
b = 6.0370 (1) Å
c = 21.0740 (5) Å
β = 123.267 (1)°
V = 2494.22 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 160 (1) K
0.25 × 0.20 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: none
37687 measured reflections
3640 independent reflections
2682 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.170
S = 1.08
3640 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.27 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/S1600536808009070/wn2249sup1.cif

e-64-0o818-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009070/wn2249Isup2.hkl

e-64-0o818-Isup2.hkl^{(175KB, 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
C4—H4A⋯Cgⁱ	0.99	2.61	3.5425 (15)	157

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Symmetry code: (i) Inline graphic . Cg is the centroid of the benzene 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 cyclohexanes (Subramanyam et al., 2007). Its molecular structure, with atomic numbering scheme, is shown in Fig. 1. The cyclohexane ring adopts a chair conformation. The cyano group and the methyl group at position 1 have axial and equatorial orientations respectively. The benzene ring at position 5 has an equatorial orientation. A C4—H4A···π(-x, y, 1/2 - z) interaction involving the benzene ring is found in the structure. No classical hydrogen bonds are found in the crystal structure.

Experimental

A mixture of 5-4'-methylphenyl-3-methylcyclohex-2-enone (4.00 g, 0.02 mol), potassium cyanide (2.60 g, 0.04 mol), ammonium chloride (1.59 g, 0.03 mol), dimethylformamide (50 ml) and water (2 ml) was heated with stirring for 16-18 h at 353 K. The reaction mixture was cooled to room temperature and poured into water. The product was extracted with CH₂Cl₂ (3x10 ml) and the organic layer was dried, evaporated and purified by column chromatography (hexane-EtOAc, 4.5:1 v/v). The yield of the isolated product was 3.40 g (75%).