organic compounds
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
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
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Data collection
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell 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.
Supporting information
10.1107/S1600536812043139/hb6965sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812043139/hb6965Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812043139/hb6965Isup3.cml
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.
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.
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell
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).C18H17FO4 | F(000) = 664 |
Mr = 316.32 | Dx = 1.304 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3057 reflections |
a = 7.0927 (3) Å | θ = 2.5–25.7° |
b = 25.9711 (11) Å | µ = 0.10 mm−1 |
c = 8.7487 (4) Å | T = 296 K |
β = 91.584 (4)° | Block, brown |
V = 1610.94 (12) Å3 | 0.22 × 0.22 × 0.20 mm |
Z = 4 |
Oxford Diffraction Xcalibur Eos CCD diffractometer | 1946 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.037 |
Graphite monochromator | θmax = 25.7°, θmin = 2.5° |
Detector resolution: 16.0839 pixels mm-1 | h = −8→8 |
ω scans | k = −31→30 |
16217 measured reflections | l = −10→10 |
3057 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-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 reflections | Δρmax = 0.17 e Å−3 |
212 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.023 (2) |
C18H17FO4 | V = 1610.94 (12) Å3 |
Mr = 316.32 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.0927 (3) Å | µ = 0.10 mm−1 |
b = 25.9711 (11) Å | T = 296 K |
c = 8.7487 (4) Å | 0.22 × 0.22 × 0.20 mm |
β = 91.584 (4)° |
Oxford Diffraction Xcalibur Eos CCD diffractometer | 1946 reflections with I > 2σ(I) |
16217 measured reflections | Rint = 0.037 |
3057 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.17 e Å−3 |
3057 reflections | Δρmin = −0.14 e Å−3 |
212 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
F1 | 0.47580 (14) | 0.21236 (4) | 0.09672 (13) | 0.0862 (5) | |
O1 | 0.05893 (17) | 0.14446 (4) | 0.32501 (13) | 0.0687 (4) | |
O2 | 0.65872 (14) | 0.07225 (4) | 0.09354 (13) | 0.0565 (4) | |
O3 | 0.81263 (17) | −0.10017 (4) | 0.20765 (13) | 0.0681 (5) | |
O4 | 0.24772 (16) | −0.02139 (4) | 0.39762 (13) | 0.0641 (4) | |
C1 | 0.2939 (2) | 0.22710 (6) | 0.06805 (19) | 0.0569 (7) | |
C2 | 0.2679 (3) | 0.27123 (7) | −0.0164 (2) | 0.0709 (8) | |
C3 | 0.0855 (4) | 0.28686 (7) | −0.0490 (2) | 0.0775 (9) | |
C4 | −0.0645 (3) | 0.25900 (7) | 0.0031 (2) | 0.0724 (8) | |
C5 | −0.0318 (2) | 0.21601 (6) | 0.09185 (19) | 0.0583 (6) | |
C6 | 0.1499 (2) | 0.19858 (6) | 0.12600 (17) | 0.0463 (5) | |
C7 | 0.1721 (2) | 0.15104 (6) | 0.22354 (17) | 0.0464 (5) | |
C8 | 0.3191 (2) | 0.11421 (6) | 0.19021 (17) | 0.0471 (5) | |
C9 | 0.3266 (2) | 0.06858 (5) | 0.26294 (17) | 0.0444 (5) | |
C10 | 0.4532 (2) | 0.02558 (5) | 0.24723 (16) | 0.0422 (5) | |
C11 | 0.6197 (2) | 0.02680 (6) | 0.16292 (16) | 0.0448 (5) | |
C12 | 0.7362 (2) | −0.01548 (6) | 0.15323 (17) | 0.0516 (6) | |
C13 | 0.6887 (2) | −0.06078 (6) | 0.22712 (18) | 0.0510 (6) | |
C14 | 0.5274 (2) | −0.06425 (6) | 0.31166 (18) | 0.0519 (6) | |
C15 | 0.4117 (2) | −0.02141 (6) | 0.32072 (16) | 0.0463 (6) | |
C16 | 0.8256 (2) | 0.07605 (6) | 0.00797 (19) | 0.0596 (7) | |
C17 | 0.7766 (3) | −0.14799 (6) | 0.2812 (2) | 0.0782 (8) | |
C18 | 0.1869 (3) | −0.06735 (6) | 0.4707 (2) | 0.0699 (7) | |
H2 | 0.37020 | 0.29000 | −0.05050 | 0.0850* | |
H3 | 0.06380 | 0.31650 | −0.10660 | 0.0930* | |
H4 | −0.18730 | 0.26920 | −0.02150 | 0.0870* | |
H5 | −0.13400 | 0.19810 | 0.13000 | 0.0700* | |
H8 | 0.40860 | 0.12220 | 0.11820 | 0.0570* | |
H9 | 0.23470 | 0.06400 | 0.33550 | 0.0530* | |
H12 | 0.84580 | −0.01370 | 0.09760 | 0.0620* | |
H14 | 0.49710 | −0.09470 | 0.36140 | 0.0620* | |
H16A | 0.93360 | 0.07030 | 0.07430 | 0.0890* | |
H16B | 0.83310 | 0.10980 | −0.03650 | 0.0890* | |
H16C | 0.82270 | 0.05060 | −0.07170 | 0.0890* | |
H17A | 0.77770 | −0.14300 | 0.39000 | 0.1170* | |
H17B | 0.87250 | −0.17240 | 0.25570 | 0.1170* | |
H17C | 0.65550 | −0.16080 | 0.24760 | 0.1170* | |
H18A | 0.16980 | −0.09410 | 0.39580 | 0.1050* | |
H18B | 0.06970 | −0.06100 | 0.51960 | 0.1050* | |
H18C | 0.28040 | −0.07790 | 0.54580 | 0.1050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0529 (7) | 0.1002 (8) | 0.1054 (9) | −0.0147 (6) | 0.0030 (6) | 0.0333 (7) |
O1 | 0.0699 (8) | 0.0614 (7) | 0.0766 (8) | 0.0155 (6) | 0.0370 (7) | 0.0142 (6) |
O2 | 0.0464 (7) | 0.0508 (7) | 0.0734 (8) | 0.0010 (5) | 0.0218 (6) | 0.0077 (6) |
O3 | 0.0714 (9) | 0.0548 (7) | 0.0788 (8) | 0.0200 (6) | 0.0136 (7) | 0.0074 (6) |
O4 | 0.0553 (8) | 0.0594 (7) | 0.0789 (8) | −0.0048 (6) | 0.0233 (6) | 0.0108 (6) |
C1 | 0.0501 (12) | 0.0633 (11) | 0.0573 (11) | −0.0054 (9) | 0.0000 (9) | 0.0046 (9) |
C2 | 0.0886 (16) | 0.0605 (12) | 0.0639 (12) | −0.0176 (11) | 0.0057 (11) | 0.0126 (10) |
C3 | 0.1100 (19) | 0.0544 (12) | 0.0676 (13) | 0.0113 (13) | −0.0069 (13) | 0.0107 (10) |
C4 | 0.0753 (15) | 0.0611 (12) | 0.0803 (14) | 0.0190 (11) | −0.0039 (11) | 0.0038 (10) |
C5 | 0.0552 (12) | 0.0542 (10) | 0.0659 (11) | 0.0074 (9) | 0.0078 (9) | −0.0036 (9) |
C6 | 0.0465 (10) | 0.0444 (9) | 0.0482 (9) | −0.0005 (8) | 0.0055 (8) | −0.0024 (7) |
C7 | 0.0435 (9) | 0.0471 (9) | 0.0490 (9) | −0.0032 (8) | 0.0067 (8) | −0.0024 (7) |
C8 | 0.0405 (9) | 0.0525 (10) | 0.0488 (9) | 0.0013 (8) | 0.0083 (7) | 0.0004 (8) |
C9 | 0.0383 (9) | 0.0505 (9) | 0.0447 (9) | −0.0028 (7) | 0.0059 (7) | −0.0032 (7) |
C10 | 0.0369 (9) | 0.0464 (9) | 0.0435 (8) | −0.0006 (7) | 0.0024 (7) | −0.0016 (7) |
C11 | 0.0427 (9) | 0.0456 (9) | 0.0462 (9) | −0.0009 (8) | 0.0021 (7) | −0.0007 (7) |
C12 | 0.0444 (10) | 0.0573 (10) | 0.0536 (10) | 0.0035 (8) | 0.0095 (8) | −0.0001 (8) |
C13 | 0.0515 (11) | 0.0504 (10) | 0.0510 (10) | 0.0083 (8) | −0.0013 (8) | −0.0044 (8) |
C14 | 0.0576 (11) | 0.0445 (9) | 0.0535 (10) | −0.0025 (8) | 0.0013 (9) | 0.0026 (8) |
C15 | 0.0419 (10) | 0.0514 (10) | 0.0457 (9) | −0.0057 (8) | 0.0045 (8) | −0.0005 (7) |
C16 | 0.0488 (11) | 0.0609 (11) | 0.0700 (12) | −0.0068 (8) | 0.0182 (9) | −0.0010 (9) |
C17 | 0.0957 (16) | 0.0518 (11) | 0.0871 (14) | 0.0165 (11) | 0.0049 (12) | 0.0052 (10) |
C18 | 0.0680 (13) | 0.0693 (12) | 0.0732 (13) | −0.0206 (10) | 0.0182 (10) | 0.0127 (10) |
F1—C1 | 1.3624 (18) | C12—C13 | 1.388 (2) |
O1—C7 | 1.2251 (19) | C13—C14 | 1.382 (2) |
O2—C11 | 1.3593 (19) | C14—C15 | 1.386 (2) |
O2—C16 | 1.4213 (18) | C2—H2 | 0.9300 |
O3—C13 | 1.3625 (19) | C3—H3 | 0.9300 |
O3—C17 | 1.4251 (19) | C4—H4 | 0.9300 |
O4—C15 | 1.3596 (18) | C5—H5 | 0.9300 |
O4—C18 | 1.427 (2) | C8—H8 | 0.9300 |
C1—C2 | 1.373 (2) | C9—H9 | 0.9300 |
C1—C6 | 1.370 (2) | C12—H12 | 0.9300 |
C2—C3 | 1.378 (3) | C14—H14 | 0.9300 |
C3—C4 | 1.375 (3) | C16—H16A | 0.9600 |
C4—C5 | 1.376 (2) | C16—H16B | 0.9600 |
C5—C6 | 1.391 (2) | C16—H16C | 0.9600 |
C6—C7 | 1.507 (2) | C17—H17A | 0.9600 |
C7—C8 | 1.451 (2) | C17—H17B | 0.9600 |
C8—C9 | 1.345 (2) | C17—H17C | 0.9600 |
C9—C10 | 1.4419 (19) | C18—H18A | 0.9600 |
C10—C11 | 1.410 (2) | C18—H18B | 0.9600 |
C10—C15 | 1.414 (2) | C18—H18C | 0.9600 |
C11—C12 | 1.378 (2) | ||
C11—O2—C16 | 118.58 (11) | C3—C2—H2 | 121.00 |
C13—O3—C17 | 118.26 (13) | C2—C3—H3 | 120.00 |
C15—O4—C18 | 119.66 (13) | C4—C3—H3 | 120.00 |
F1—C1—C2 | 116.49 (15) | C3—C4—H4 | 120.00 |
F1—C1—C6 | 119.46 (14) | C5—C4—H4 | 120.00 |
C2—C1—C6 | 124.04 (15) | C4—C5—H5 | 119.00 |
C1—C2—C3 | 117.94 (18) | C6—C5—H5 | 119.00 |
C2—C3—C4 | 120.46 (17) | C7—C8—H8 | 120.00 |
C3—C4—C5 | 119.62 (19) | C9—C8—H8 | 120.00 |
C4—C5—C6 | 121.75 (15) | C8—C9—H9 | 115.00 |
C1—C6—C5 | 116.13 (14) | C10—C9—H9 | 115.00 |
C1—C6—C7 | 125.82 (13) | C11—C12—H12 | 120.00 |
C5—C6—C7 | 118.05 (13) | C13—C12—H12 | 120.00 |
O1—C7—C6 | 117.67 (13) | C13—C14—H14 | 121.00 |
O1—C7—C8 | 122.87 (14) | C15—C14—H14 | 121.00 |
C6—C7—C8 | 119.41 (13) | O2—C16—H16A | 109.00 |
C7—C8—C9 | 120.33 (13) | O2—C16—H16B | 109.00 |
C8—C9—C10 | 130.82 (14) | O2—C16—H16C | 109.00 |
C9—C10—C11 | 124.42 (13) | H16A—C16—H16B | 110.00 |
C9—C10—C15 | 119.15 (13) | H16A—C16—H16C | 109.00 |
C11—C10—C15 | 116.43 (13) | H16B—C16—H16C | 110.00 |
O2—C11—C10 | 115.91 (13) | O3—C17—H17A | 109.00 |
O2—C11—C12 | 122.32 (13) | O3—C17—H17B | 109.00 |
C10—C11—C12 | 121.77 (14) | O3—C17—H17C | 110.00 |
C11—C12—C13 | 119.53 (13) | H17A—C17—H17B | 109.00 |
O3—C13—C12 | 114.35 (13) | H17A—C17—H17C | 109.00 |
O3—C13—C14 | 124.35 (14) | H17B—C17—H17C | 109.00 |
C12—C13—C14 | 121.30 (14) | O4—C18—H18A | 109.00 |
C13—C14—C15 | 118.58 (14) | O4—C18—H18B | 109.00 |
O4—C15—C10 | 114.60 (13) | O4—C18—H18C | 109.00 |
O4—C15—C14 | 122.99 (13) | H18A—C18—H18B | 110.00 |
C10—C15—C14 | 122.39 (13) | H18A—C18—H18C | 109.00 |
C1—C2—H2 | 121.00 | H18B—C18—H18C | 110.00 |
C16—O2—C11—C10 | 179.43 (13) | O1—C7—C8—C9 | 5.6 (2) |
C16—O2—C11—C12 | 0.1 (2) | C6—C7—C8—C9 | −171.60 (14) |
C17—O3—C13—C12 | 179.14 (14) | C7—C8—C9—C10 | 178.00 (14) |
C17—O3—C13—C14 | −1.2 (2) | C8—C9—C10—C11 | 10.4 (3) |
C18—O4—C15—C10 | 177.28 (13) | C8—C9—C10—C15 | −169.93 (15) |
C18—O4—C15—C14 | −1.3 (2) | C9—C10—C11—O2 | 0.1 (2) |
F1—C1—C2—C3 | 179.23 (15) | C9—C10—C11—C12 | 179.39 (14) |
C6—C1—C2—C3 | −2.2 (3) | C15—C10—C11—O2 | −179.62 (12) |
F1—C1—C6—C5 | −179.97 (13) | C15—C10—C11—C12 | −0.3 (2) |
F1—C1—C6—C7 | 0.8 (2) | C9—C10—C15—O4 | 1.86 (19) |
C2—C1—C6—C5 | 1.5 (2) | C9—C10—C15—C14 | −179.54 (14) |
C2—C1—C6—C7 | −177.78 (16) | C11—C10—C15—O4 | −178.45 (12) |
C1—C2—C3—C4 | 0.5 (3) | C11—C10—C15—C14 | 0.2 (2) |
C2—C3—C4—C5 | 1.8 (3) | O2—C11—C12—C13 | 179.81 (13) |
C3—C4—C5—C6 | −2.5 (3) | C10—C11—C12—C13 | 0.5 (2) |
C4—C5—C6—C1 | 0.9 (2) | C11—C12—C13—O3 | 179.05 (13) |
C4—C5—C6—C7 | −179.77 (15) | C11—C12—C13—C14 | −0.6 (2) |
C1—C6—C7—O1 | 144.10 (16) | O3—C13—C14—C15 | −179.15 (14) |
C1—C6—C7—C8 | −38.5 (2) | C12—C13—C14—C15 | 0.5 (2) |
C5—C6—C7—O1 | −35.2 (2) | C13—C14—C15—O4 | 178.24 (14) |
C5—C6—C7—C8 | 142.22 (15) | C13—C14—C15—C10 | −0.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.93 | 2.44 | 3.338 (2) | 162 |
Symmetry code: (i) x+1/2, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H17FO4 |
Mr | 316.32 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 7.0927 (3), 25.9711 (11), 8.7487 (4) |
β (°) | 91.584 (4) |
V (Å3) | 1610.94 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.22 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Eos CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16217, 3057, 1946 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.610 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.100, 1.00 |
No. of reflections | 3057 |
No. of parameters | 212 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.14 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and Mercury (Macrae et al., 2006).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.9300 | 2.4400 | 3.338 (2) | 162.00 |
Symmetry code: (i) x+1/2, −y+1/2, z−1/2. |
Acknowledgements
SMK thanks the UGC–BRS and the University of Mysore for the award of a fellowship.
References
Jasinski, 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 Google Scholar
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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
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. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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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).