3-[(E)-2-(2-Meth­oxy­phen­yl)vin­yl]-5,5-di­methyl­cyclo­hex-2-enone

Zeenat Fatima; Govindaraj Senthilkumar; A Vadivel; Haridoss Manikandan; Devadasan Velmurugan

doi:10.1107/S1600536814006527

. 2014 Apr 2;70(Pt 5):o509. doi: 10.1107/S1600536814006527

3-[(E)-2-(2-Methoxyphenyl)vinyl]-5,5-dimethylcyclohex-2-enone

Zeenat Fatima ^a, Govindaraj Senthilkumar ^b, A Vadivel ^b, Haridoss Manikandan ^b, Devadasan Velmurugan ^a,^*

PMCID: PMC4011279 PMID: 24860325

Abstract

The title compound, C₁₇H₂₀O₂, has an E conformation about the bridging C=C bond. The cyclohexene ring adopts an envelope conformation with the dimethyl-substituted C atom as the flap. Its mean plane makes a dihedral angle of 7.20 (12)° with the benzene ring. In the crystal, neighbouring molecules are connected via C—H⋯O hydrogen bonds, forming chains running along the a-axis direction.

Related literature

For the pharmacological activity of cyclohexanone derivatives, see: Puetz et al. (2003 ▶); Rajveer et al. (2010 ▶). For related structures, see: Fatima et al. (2013 ▶); Hema et al. (2006 ▶). For ring puckering parametes, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₇H₂₀O₂
M _r = 256.33
Monoclinic,
a = 7.208 (4) Å
b = 13.824 (7) Å
c = 15.022 (8) Å
β = 92.13 (2)°
V = 1495.8 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.978, T _max = 0.986
10491 measured reflections
3517 independent reflections
2489 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.085
wR(F ²) = 0.283
S = 1.06
3517 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814006527/su2717sup1.cif

e-70-0o509-sup1.cif^{(24.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006527/su2717Isup2.hkl

e-70-0o509-Isup2.hkl^{(169KB, hkl)}

Click here for additional data file.^{(5.8KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814006527/su2717Isup3.cml

CCDC reference: 993438

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O1ⁱ	0.97	2.62	3.554 (4)	161

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and ZF thanks the UGC for a meritorious fellowship.

supplementary crystallographic information

1. Comment

Cyclohexanone is an aliphatic cyclic ketone. Cyclohexanone derivatives have potent pharmacological activity in the treatment of a broad spectrum of medical conditions (Puetz et al., 2003). The cyclohexanone moiety constitutes an important structural feature in several anti-inflammatory, analgesic, local anesthetic and antihistaminic drugs (Rajveer et al., 2010). As part of our studies in this area (Fatima et al., 2013; Hema et al., 2006), we have undertaken a single-crystal structure determination of the title compound.

In the title compound, Fig. 1, the cyclohexene ring (C9—C14) adopts an envelope conformation with atom C13 as the flap: puckering parameters (Cremer & Pople, 1975) are Q = 0.464 (3) Å, θ = 52.3 (4) °, and φ = 232.2 (4) °. Its mean plane makes a dihedral angle of 7.20 (12)° with the benzene ring (C1—C6).

In the crystal, hydrogen bonded chains running along the a-axis direction are generated by connecting neighbouring molecules via C—H···O hydrogen bonds (Table 1 and Fig. 2).

2. Experimental

A mixture of isophorone (0.01 mol), 2-methoxybezaldehyde (0.01 mol) and sodium hydroxide solution (10 ml, 10%) in ethanol (25 ml) was stirred at room temperature until the starting material disappeared. The resulting mixture was poured into crushed ice and the precipitate was filtered off, dried and recrystallized from ethanol giving p. colourless block-like crystals [Yield = 93%; M.p. = 373-375 K].