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

Prabuswamy, M.; Madan Kumar, S.; Bhuvaneshwar, D.; Murthy, C.S.S.S.; Lokanath, N.K.

doi:10.1107/S1600536812043139

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3190

doi:10.1107/S1600536812043139

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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 and N. K. Lokanath ^a ^*

^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 ). For a related structure, see: Jasinski et al. (2009 ).

Experimental

Crystal data

C₁₈H₁₇FO₄
M_r = 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)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 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

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
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 ); 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812043139/hb6965sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812043139/hb6965Isup3.cml

checkCIF report

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.

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

	Fig. 1. ORTEP diagram of the title compound with 50% probability ellipsoids.
	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

C₁₈H₁₇FO₄	F(000) = 664
M_r = 316.32	D_x = 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

Data collection top

Oxford Diffraction Xcalibur Eos CCD diffractometer	1946 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 25.7°, θ_min = 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 top

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(F_o²) + (0.0497P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3057 reflections	Δρ_max = 0.17 e Å⁻³
212 parameters	Δρ_min = −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)

Crystal data top

C₁₈H₁₇FO₄	V = 1610.94 (12) Å³
M_r = 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)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.00	Δρ_max = 0.17 e Å⁻³
3057 reflections	Δρ_min = −0.14 e Å⁻³
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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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

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