1-(2-Fluoro-phen-yl)-3-(2,4,6-trimeth-oxy-phen-yl)prop-2-en-1-one.

In the title compound, C(18)H(17)FO(4), the dihedral angle between the aromatic rings is 32.29 (8)°. The C atoms of the meth-oxy 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 mol-ecules 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 = 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

Δρmax = 0.17 e Å−3

Δρmin = −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.

Click here for additional data file.

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

Click here for additional data file.

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

Click here for additional data file.

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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)

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

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) .