1-(2-Fluoro­phen­yl)-3-(2,4,6-trimeth­oxy­phen­yl)prop-2-en-1-one

M Prabuswamy; S Madan Kumar; D Bhuvaneshwar; Ch S S S Murthy; N K Lokanath

doi:10.1107/S1600536812043139

. 2012 Oct 20;68(Pt 11):o3190. doi: 10.1107/S1600536812043139

1-(2-Fluorophenyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one

M Prabuswamy ^a, S Madan Kumar ^a, D Bhuvaneshwar ^b, Ch S S S Murthy ^b, N K Lokanath ^a,^*

PMCID: PMC3515281 PMID: 23284501

Abstract

In the title compound, C₁₈H₁₇FO₄, the dihedral angle between the aromatic rings is 32.29 (8)°. The C atoms of the methoxy groups deviate from their attached ring plane by 0.018 (2), −0.006 (2) and −0.094 (2) Å. In the crystal, C—H⋯O hydrogen bonds link the molecules into C(6) [001] chains.

Related literature

For the synthesis and properties of the title compound, see: Rimal et al. (2012 ▶). For a related structure, see: Jasinski et al. (2009 ▶).

Experimental

Crystal data

C₁₈H₁₇FO₄
M _r = 316.32
Monoclinic,
a = 7.0927 (3) Å
b = 25.9711 (11) Å
c = 8.7487 (4) Å
β = 91.584 (4)°
V = 1610.94 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.22 × 0.22 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos CCD diffractometer
16217 measured reflections
3057 independent reflections
1946 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.100
S = 1.00
3057 reflections
212 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and Mercury.

Supplementary Material

Click here for additional data file.^{(25.6KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043139/hb6965sup1.cif

e-68-o3190-sup1.cif^{(25.6KB, cif)}

Click here for additional data file.^{(150KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043139/hb6965Isup2.hkl

e-68-o3190-Isup2.hkl^{(150KB, hkl)}

Click here for additional data file.^{(6.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812043139/hb6965Isup3.cml

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	0.93	2.44	3.338 (2)	162

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

SMK thanks the UGC–BRS and the University of Mysore for the award of a fellowship.

supplementary crystallographic information

Comment

As part of our ongoing studies of chalcones with possible biological activity (Rimal et al., 2012), we now describe the crystal structure of 1-(2-fluorophenyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one, (I).

The ORTEP drawing of the title molecule is as shown in Fig. 1. The dihedral angle between the aromatic rings of 2-flurophenyl and trimethoxy phenyl group is 32.29 (8)°. Mean plane of prop-2-ene-1 one moiety makes an angle of 37.65 (9)° with 2-flurophenyl and 11.64 (9)° with trimethoxyphenyl moiety. The overall geometry of the title compound is similar to that of (2E)-1-(4-fluorophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (Jasinski et al., 2009).

The molecules are connected by C—H···O interactions (Fig. 2).

Experimental

The title compound was synthesized as per the procedure reported in the literature (Rimal et al., 2012). The final product was obtained by recrystallization using aqueous ethyl acetate: methanol as a solvent. Slow evaporation method yielded brown blocks.