organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and bDepartment of Nanotechnology, School of Interdisciplinary Courses, Noorul Islam Centre for Higher Education, Kumarcoil, Kanyakumari 629 180, India
*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

(Received 28 September 2012; accepted 16 October 2012; online 20 October 2012)

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[Rimal, I., SriBindu, M. C., Sudhakar, P. R., JosephJoly, V. L., Wu, R. J. & ChMurthy, S. S. S. (2012). Adv. Sci. Eng. Med. 4, 1-7.]). For a related structure, see: Jasinski et al. (2009[Jasinski, J. P., Butcher, R. J., Veena, K., Narayana, B. & Yathirajan, H. S. (2009). Acta Cryst. E65, o1965-o1966.]).

[Scheme 1]

Experimental

Crystal data
  • C18H17FO4

  • Mr = 316.32

  • Monoclinic, P 21 /n

  • 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)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.100

  • S = 1.00

  • 3057 reflections

  • 212 parameters

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.14 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯O1i 0.93 2.44 3.338 (2) 162
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97 and Mercury.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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.

Refinement top

All the hydrogen atoms of the compound are fixed geometrically (C—H= 0.93–0.97 Å) and allowed to ride on their parent atoms.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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 (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Figures top
[Figure 1] Fig. 1. ORTEP diagram of the title compound with 50% probability ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound, viewed along the crystallographic a axis. C—H···O hydrogen bonds are indicated by dashed lines.
1-(2-Fluorophenyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one top
Crystal data top
C18H17FO4F(000) = 664
Mr = 316.32Dx = 1.304 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3057 reflections
a = 7.0927 (3) Åθ = 2.5–25.7°
b = 25.9711 (11) ŵ = 0.10 mm1
c = 8.7487 (4) ÅT = 296 K
β = 91.584 (4)°Block, brown
V = 1610.94 (12) Å30.22 × 0.22 × 0.20 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur Eos CCD
diffractometer
1946 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 25.7°, θmin = 2.5°
Detector resolution: 16.0839 pixels mm-1h = 88
ω scansk = 3130
16217 measured reflectionsl = 1010
3057 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.100 w = 1/[σ2(Fo2) + (0.0497P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3057 reflectionsΔρmax = 0.17 e Å3
212 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.023 (2)
Crystal data top
C18H17FO4V = 1610.94 (12) Å3
Mr = 316.32Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.0927 (3) ŵ = 0.10 mm1
b = 25.9711 (11) ÅT = 296 K
c = 8.7487 (4) Å0.22 × 0.22 × 0.20 mm
β = 91.584 (4)°
Data collection top
Oxford Diffraction Xcalibur Eos CCD
diffractometer
1946 reflections with I > 2σ(I)
16217 measured reflectionsRint = 0.037
3057 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 1.00Δρmax = 0.17 e Å3
3057 reflectionsΔρmin = 0.14 e Å3
212 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.47580 (14)0.21236 (4)0.09672 (13)0.0862 (5)
O10.05893 (17)0.14446 (4)0.32501 (13)0.0687 (4)
O20.65872 (14)0.07225 (4)0.09354 (13)0.0565 (4)
O30.81263 (17)0.10017 (4)0.20765 (13)0.0681 (5)
O40.24772 (16)0.02139 (4)0.39762 (13)0.0641 (4)
C10.2939 (2)0.22710 (6)0.06805 (19)0.0569 (7)
C20.2679 (3)0.27123 (7)0.0164 (2)0.0709 (8)
C30.0855 (4)0.28686 (7)0.0490 (2)0.0775 (9)
C40.0645 (3)0.25900 (7)0.0031 (2)0.0724 (8)
C50.0318 (2)0.21601 (6)0.09185 (19)0.0583 (6)
C60.1499 (2)0.19858 (6)0.12600 (17)0.0463 (5)
C70.1721 (2)0.15104 (6)0.22354 (17)0.0464 (5)
C80.3191 (2)0.11421 (6)0.19021 (17)0.0471 (5)
C90.3266 (2)0.06858 (5)0.26294 (17)0.0444 (5)
C100.4532 (2)0.02558 (5)0.24723 (16)0.0422 (5)
C110.6197 (2)0.02680 (6)0.16292 (16)0.0448 (5)
C120.7362 (2)0.01548 (6)0.15323 (17)0.0516 (6)
C130.6887 (2)0.06078 (6)0.22712 (18)0.0510 (6)
C140.5274 (2)0.06425 (6)0.31166 (18)0.0519 (6)
C150.4117 (2)0.02141 (6)0.32072 (16)0.0463 (6)
C160.8256 (2)0.07605 (6)0.00797 (19)0.0596 (7)
C170.7766 (3)0.14799 (6)0.2812 (2)0.0782 (8)
C180.1869 (3)0.06735 (6)0.4707 (2)0.0699 (7)
H20.370200.290000.050500.0850*
H30.063800.316500.106600.0930*
H40.187300.269200.021500.0870*
H50.134000.198100.130000.0700*
H80.408600.122200.118200.0570*
H90.234700.064000.335500.0530*
H120.845800.013700.097600.0620*
H140.497100.094700.361400.0620*
H16A0.933600.070300.074300.0890*
H16B0.833100.109800.036500.0890*
H16C0.822700.050600.071700.0890*
H17A0.777700.143000.390000.1170*
H17B0.872500.172400.255700.1170*
H17C0.655500.160800.247600.1170*
H18A0.169800.094100.395800.1050*
H18B0.069700.061000.519600.1050*
H18C0.280400.077900.545800.1050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0529 (7)0.1002 (8)0.1054 (9)0.0147 (6)0.0030 (6)0.0333 (7)
O10.0699 (8)0.0614 (7)0.0766 (8)0.0155 (6)0.0370 (7)0.0142 (6)
O20.0464 (7)0.0508 (7)0.0734 (8)0.0010 (5)0.0218 (6)0.0077 (6)
O30.0714 (9)0.0548 (7)0.0788 (8)0.0200 (6)0.0136 (7)0.0074 (6)
O40.0553 (8)0.0594 (7)0.0789 (8)0.0048 (6)0.0233 (6)0.0108 (6)
C10.0501 (12)0.0633 (11)0.0573 (11)0.0054 (9)0.0000 (9)0.0046 (9)
C20.0886 (16)0.0605 (12)0.0639 (12)0.0176 (11)0.0057 (11)0.0126 (10)
C30.1100 (19)0.0544 (12)0.0676 (13)0.0113 (13)0.0069 (13)0.0107 (10)
C40.0753 (15)0.0611 (12)0.0803 (14)0.0190 (11)0.0039 (11)0.0038 (10)
C50.0552 (12)0.0542 (10)0.0659 (11)0.0074 (9)0.0078 (9)0.0036 (9)
C60.0465 (10)0.0444 (9)0.0482 (9)0.0005 (8)0.0055 (8)0.0024 (7)
C70.0435 (9)0.0471 (9)0.0490 (9)0.0032 (8)0.0067 (8)0.0024 (7)
C80.0405 (9)0.0525 (10)0.0488 (9)0.0013 (8)0.0083 (7)0.0004 (8)
C90.0383 (9)0.0505 (9)0.0447 (9)0.0028 (7)0.0059 (7)0.0032 (7)
C100.0369 (9)0.0464 (9)0.0435 (8)0.0006 (7)0.0024 (7)0.0016 (7)
C110.0427 (9)0.0456 (9)0.0462 (9)0.0009 (8)0.0021 (7)0.0007 (7)
C120.0444 (10)0.0573 (10)0.0536 (10)0.0035 (8)0.0095 (8)0.0001 (8)
C130.0515 (11)0.0504 (10)0.0510 (10)0.0083 (8)0.0013 (8)0.0044 (8)
C140.0576 (11)0.0445 (9)0.0535 (10)0.0025 (8)0.0013 (9)0.0026 (8)
C150.0419 (10)0.0514 (10)0.0457 (9)0.0057 (8)0.0045 (8)0.0005 (7)
C160.0488 (11)0.0609 (11)0.0700 (12)0.0068 (8)0.0182 (9)0.0010 (9)
C170.0957 (16)0.0518 (11)0.0871 (14)0.0165 (11)0.0049 (12)0.0052 (10)
C180.0680 (13)0.0693 (12)0.0732 (13)0.0206 (10)0.0182 (10)0.0127 (10)
Geometric parameters (Å, º) top
F1—C11.3624 (18)C12—C131.388 (2)
O1—C71.2251 (19)C13—C141.382 (2)
O2—C111.3593 (19)C14—C151.386 (2)
O2—C161.4213 (18)C2—H20.9300
O3—C131.3625 (19)C3—H30.9300
O3—C171.4251 (19)C4—H40.9300
O4—C151.3596 (18)C5—H50.9300
O4—C181.427 (2)C8—H80.9300
C1—C21.373 (2)C9—H90.9300
C1—C61.370 (2)C12—H120.9300
C2—C31.378 (3)C14—H140.9300
C3—C41.375 (3)C16—H16A0.9600
C4—C51.376 (2)C16—H16B0.9600
C5—C61.391 (2)C16—H16C0.9600
C6—C71.507 (2)C17—H17A0.9600
C7—C81.451 (2)C17—H17B0.9600
C8—C91.345 (2)C17—H17C0.9600
C9—C101.4419 (19)C18—H18A0.9600
C10—C111.410 (2)C18—H18B0.9600
C10—C151.414 (2)C18—H18C0.9600
C11—C121.378 (2)
C11—O2—C16118.58 (11)C3—C2—H2121.00
C13—O3—C17118.26 (13)C2—C3—H3120.00
C15—O4—C18119.66 (13)C4—C3—H3120.00
F1—C1—C2116.49 (15)C3—C4—H4120.00
F1—C1—C6119.46 (14)C5—C4—H4120.00
C2—C1—C6124.04 (15)C4—C5—H5119.00
C1—C2—C3117.94 (18)C6—C5—H5119.00
C2—C3—C4120.46 (17)C7—C8—H8120.00
C3—C4—C5119.62 (19)C9—C8—H8120.00
C4—C5—C6121.75 (15)C8—C9—H9115.00
C1—C6—C5116.13 (14)C10—C9—H9115.00
C1—C6—C7125.82 (13)C11—C12—H12120.00
C5—C6—C7118.05 (13)C13—C12—H12120.00
O1—C7—C6117.67 (13)C13—C14—H14121.00
O1—C7—C8122.87 (14)C15—C14—H14121.00
C6—C7—C8119.41 (13)O2—C16—H16A109.00
C7—C8—C9120.33 (13)O2—C16—H16B109.00
C8—C9—C10130.82 (14)O2—C16—H16C109.00
C9—C10—C11124.42 (13)H16A—C16—H16B110.00
C9—C10—C15119.15 (13)H16A—C16—H16C109.00
C11—C10—C15116.43 (13)H16B—C16—H16C110.00
O2—C11—C10115.91 (13)O3—C17—H17A109.00
O2—C11—C12122.32 (13)O3—C17—H17B109.00
C10—C11—C12121.77 (14)O3—C17—H17C110.00
C11—C12—C13119.53 (13)H17A—C17—H17B109.00
O3—C13—C12114.35 (13)H17A—C17—H17C109.00
O3—C13—C14124.35 (14)H17B—C17—H17C109.00
C12—C13—C14121.30 (14)O4—C18—H18A109.00
C13—C14—C15118.58 (14)O4—C18—H18B109.00
O4—C15—C10114.60 (13)O4—C18—H18C109.00
O4—C15—C14122.99 (13)H18A—C18—H18B110.00
C10—C15—C14122.39 (13)H18A—C18—H18C109.00
C1—C2—H2121.00H18B—C18—H18C110.00
C16—O2—C11—C10179.43 (13)O1—C7—C8—C95.6 (2)
C16—O2—C11—C120.1 (2)C6—C7—C8—C9171.60 (14)
C17—O3—C13—C12179.14 (14)C7—C8—C9—C10178.00 (14)
C17—O3—C13—C141.2 (2)C8—C9—C10—C1110.4 (3)
C18—O4—C15—C10177.28 (13)C8—C9—C10—C15169.93 (15)
C18—O4—C15—C141.3 (2)C9—C10—C11—O20.1 (2)
F1—C1—C2—C3179.23 (15)C9—C10—C11—C12179.39 (14)
C6—C1—C2—C32.2 (3)C15—C10—C11—O2179.62 (12)
F1—C1—C6—C5179.97 (13)C15—C10—C11—C120.3 (2)
F1—C1—C6—C70.8 (2)C9—C10—C15—O41.86 (19)
C2—C1—C6—C51.5 (2)C9—C10—C15—C14179.54 (14)
C2—C1—C6—C7177.78 (16)C11—C10—C15—O4178.45 (12)
C1—C2—C3—C40.5 (3)C11—C10—C15—C140.2 (2)
C2—C3—C4—C51.8 (3)O2—C11—C12—C13179.81 (13)
C3—C4—C5—C62.5 (3)C10—C11—C12—C130.5 (2)
C4—C5—C6—C10.9 (2)C11—C12—C13—O3179.05 (13)
C4—C5—C6—C7179.77 (15)C11—C12—C13—C140.6 (2)
C1—C6—C7—O1144.10 (16)O3—C13—C14—C15179.15 (14)
C1—C6—C7—C838.5 (2)C12—C13—C14—C150.5 (2)
C5—C6—C7—O135.2 (2)C13—C14—C15—O4178.24 (14)
C5—C6—C7—C8142.22 (15)C13—C14—C15—C100.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.932.443.338 (2)162
Symmetry code: (i) x+1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC18H17FO4
Mr316.32
Crystal system, space groupMonoclinic, P21/n
Temperature (K)296
a, b, c (Å)7.0927 (3), 25.9711 (11), 8.7487 (4)
β (°) 91.584 (4)
V3)1610.94 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.22 × 0.22 × 0.20
Data collection
DiffractometerOxford Diffraction Xcalibur Eos CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
16217, 3057, 1946
Rint0.037
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.100, 1.00
No. of reflections3057
No. of parameters212
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.14

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.93002.44003.338 (2)162.00
Symmetry code: (i) x+1/2, y+1/2, z1/2.
 

Acknowledgements

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

References

First citationJasinski, J. P., Butcher, R. J., Veena, K., Narayana, B. & Yathirajan, H. S. (2009). Acta Cryst. E65, o1965–o1966.  Web of Science CSD CrossRef CAS IUCr Journals
First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals
First citationOxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
First citationRimal, I., SriBindu, M. C., Sudhakar, P. R., JosephJoly, V. L., Wu, R. J. & ChMurthy, S. S. S. (2012). Adv. Sci. Eng. Med. 4, 1–7.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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