5-(4-Chloro­phen­yl)-1-methyl-3-oxocyclo­hexa­necarbonitrile

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

doi:10.1107/S1600536808012816

. 2008 May 7;64(Pt 6):o1006. doi: 10.1107/S1600536808012816

5-(4-Chlorophenyl)-1-methyl-3-oxocyclohexanecarbonitrile

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

PMCID: PMC2961578 PMID: 21202532

Abstract

In the title molecule, C₁₄H₁₄ClNO, the cyclohexane ring adopts a chair conformation. The cyano group and the methyl group 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. (2007a ▶,b ▶) and Thiruvalluvar et al. (2007 ▶) have reported the crystal structures of substituted cyclohexane derivatives, in which the cyclohexane rings are in a chair conformation.

Experimental

Crystal data

C₁₄H₁₄ClNO
M _r = 247.71
Monoclinic,
a = 23.3358 (6) Å
b = 6.0031 (2) Å
c = 20.8948 (6) Å
β = 122.386 (2)°
V = 2471.81 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 160 (1) K
0.28 × 0.20 × 0.18 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (Blessing, 1995 ▶) T _min = 0.877, T _max = 0.956
28232 measured reflections
2822 independent reflections
2211 reflections with I > 2σ(I)
R _int = 0.058

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.107
S = 1.05
2822 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.32 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/S1600536808012816/ww2118sup1.cif

e-64-o1006-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012816/ww2118Isup2.hkl

e-64-o1006-Isup2.hkl^{(135.8KB, 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—H4B⋯Cgⁱ	0.99	2.60	3.5333 (18)	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

Subramanyam et al. (2007a,b) and Thiruvalluvar et al. (2007) have reported the crystal structures of substituted cyclohexane derivatives, in which the cyclohexane rings are in chair conformation. The molecular structure of the title compound, 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—H4B···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'-chlorophenyl-3-methylcyclohex-2-enone (6.40 g, 0.02 mol), potassium cyanide (2.60 g, 0.04 mol), ammonium chloride (1.59 g, 0.03 mol), dimethyl formamide (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 4.30 g (87%).