3-[(1-Bromo­naphthalen-2-yl)meth­oxy]-5,5-di­methyl­cyclo­hex-2-enone

Liang-Liang Fang; Nan Liu; Xin-Ying Zhang

doi:10.1107/S160053681301026X

. 2013 Apr 20;69(Pt 5):o758. doi: 10.1107/S160053681301026X

3-[(1-Bromonaphthalen-2-yl)methoxy]-5,5-dimethylcyclohex-2-enone

Liang-Liang Fang ^a, Nan Liu ^a, Xin-Ying Zhang ^a,^*

PMCID: PMC3648284 PMID: 23723904

Abstract

In the title compound, C₁₉H₁₉BrO₂, the cyclohexenone ring adopts an envelope conformation with the C atom bearing the methyl substituents as the flap. In the crystal, weak π–π stacking is observed between parallel aromatic rings of adjacent molecules, the centroid–centroid distance being 3.694 (6) Å. The entire bromonaphthylmethyl unit is disordered over two orientations, with a site-occupancy ratio of 0.5214 (19):0.4786 (19).

Related literature

For the biological activity and applications of cyclohex-2-enone derivatives, see: Aghil et al. (1992 ▶); Correcia et al. (2001 ▶); Ghorab et al. (2011 ▶). graphic file with name e-69-0o758-scheme1.jpg

Experimental

Crystal data

C₁₉H₁₉BrO₂
M _r = 359.25
Monoclinic,
a = 13.986 (3) Å
b = 9.9970 (18) Å
c = 11.859 (2) Å
β = 91.169 (2)°
V = 1657.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.48 mm⁻¹
T = 296 K
0.32 × 0.29 × 0.27 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.504, T _max = 0.554
11934 measured reflections
3075 independent reflections
1931 reflections with I > 2σ(I)
R _int = 0.074

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.199
S = 1.07
3075 reflections
222 parameters
72 restraints
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Click here for additional data file.^{(24KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681301026X/xu5694sup1.cif

e-69-0o758-sup1.cif^{(24KB, cif)}

Click here for additional data file.^{(150.9KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301026X/xu5694Isup2.hkl

e-69-0o758-Isup2.hkl^{(150.9KB, hkl)}

Click here for additional data file.^{(2.8KB, cdx)}

Supplementary material file. DOI: 10.1107/S160053681301026X/xu5694Isup3.cdx

Click here for additional data file.^{(6.2KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681301026X/xu5694Isup4.cml

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 21172057).

supplementary crystallographic information

Comment

Cyclohex-2-enone derivatives display a wide range of biological activities (Aghil et al., 1992; Correcia et al., 2001). Moreover, they have been frequently used as precursors in the synthesis of heterocyclic compounds (Ghorab, et al., 2011). The title compound is the derivative of cyclohex-2-enones, and we report its crystal structure here.

In the title compound, C₁₉H₁₉BrO₂, all the bond lengths and bond angles are within normal ranges. The cyclohexenone ring adopts an envelope conformation with the C atom bearing two methyl groups as the flap atom. All the atoms in the o-bromonaphthylmethyl group are disordered over two positions with site occupancy factors of 0.521 (2) and 0.479 (2).

In the crystal structure, weak π-π stacking is observed between parallel aromatic rings of adjacent molecules, the centrods distance being 3.694 (6) Å.

Experimental

To a solution of 1-bromo-2-(bromomethyl)naphthalene (0.15 g, 0.5 mmol) and 5,5-dimethylcyclohexane-1,3-dione (0.14 g, 1.0 mmol) in DMF (3 ml) were added K₂CO₃ (0.21 g, 1.5 mmol) and CuI (0.01 g, 0.05 mmol). The mixture was stirred at 373 K until a complete conversion. It was cooled to room temperature and added with water, then extracted with ethyl ether (5 ml × 3). The combined organic phases were concentrated under vacuum. The crude product was purified by column chromatography eluting with ethyl acetate/hexane (10–20%) to give the title compound with the yield of 32% (0.057 g, 0.16 mmol). Single crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of the solvents from a chloroform-ethyl acetate (1:1 v/v) solution of the title compound.