3-(4-Fluoro­phen­yl)-1-(4-methoxy­phen­yl)prop-2-en-1-one

Zhao, P.-S.; Wang, X.; Guo, H.-M.; Jian, F.-F.

doi:10.1107/S1600536809018121

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1402

doi:10.1107/S1600536809018121

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3-(4-Fluorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one

Pu-Su Zhao,^a Xian Wang,^a Huan-Mei Guo ^b and Fang-Fang Jian ^b ^*

^aNew Materials and Function Coordination Chemistry Laboratory, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China, and ^bMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 26 April 2009; accepted 13 May 2009; online 29 May 2009)

The title compound, C₁₆H₁₃FO₂, was prepared from 4-methoxyhypnone and 4-fluorobenzophenone by Claisen–Schmidt condensation. All the bond lengths and bond angles are in normal ranges. The dihedral angle formed by the two benzene rings is 33.49 (2)°. The crystal packing is stabilized by intermolecular C—H⋯O hydrogen-bonding interactions.

Related literature

For the biological activity of chalcones, see: Hsieh et al. (1998 ); Anto et al. (1994 ). For the effectiveness of chalcones against cancer, see: De Vincenzo et al. (2000 ); Dimmock et al. (1998 ). For a related structure, see: Guo et al. (2008 ).

Experimental

Crystal data

C₁₆H₁₃FO₂
M_r = 256.26
Orthorhombic, P b c a
a = 7.457 (4) Å
b = 11.072 (6) Å
c = 31.063 (18) Å
V = 2565 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 K
0.13 × 0.12 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
14904 measured reflections
3050 independent reflections
2203 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.116
S = 1.01
3050 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O2ⁱ	0.93	2.50	3.376 (2)	158
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018121/at2773sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809018121/at2773Isup2.hkl

checkCIF report

Comment top

Among flavonoids, chalcones have been identified as interesting compounds having multiple biological actions which include antiinflammatory (Hsieh et al., 1998) and antioxidant (Anto et al., 1994). Of particular interest, the effectiveness of chalcones againist cancer has been investigated (De Vincenzo et al., 2000; Dimmock et al., 1998). As part of our search for new biologically active compounds we synthesized the title compound (I) and report its crystal structure here.

In the crystal structure of compound (I) (Fig. 1), the dihedral angle formed by the benzene rings (C1–C6) and (C7–C12) is 33.49 (2)°. All the bond lengths and bond angles are in normal ranges. (Guo et al., 2008). There are intra- and intermolecular C—H···O hydrogen-bond interactions to stabilize the crystal structure (Table 1, Fig. 2).

Related literature top

For the biological activity of chalcones, see: Hsieh et al. (1998); Anto et al. (1994). For the effectiveness of chalcones against cancer, see: De Vincenzo et al. (2000); Dimmock et al. (1998). For a related structure, see: Guo et al. (2008).

Experimental top

A mixture of the 4-methoxyhypnone (0.02 mol), 4-fluorobenzophenone (0.02 mol) and 10% NaOH (10 ml) was stirred in ethanol (30 ml) for 3 h to afford the title compound (yield 83%). Single crystals suitable for X-ray measurements were obtailed by recrystallization from ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The packing and the hydrogen bonding interactions of (I),viewed down a axis.

3-(4-Fluorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₃FO₂	F(000) = 1072
M_r = 256.26	D_x = 1.327 Mg m⁻³ D_m = 1.327 Mg m⁻³ D_m measured by not measured
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4576 reflections
a = 7.457 (4) Å	θ = 2.6–27.2°
b = 11.072 (6) Å	µ = 0.10 mm⁻¹
c = 31.063 (18) Å	T = 273 K
V = 2565 (3) Å³	Bar, yellow
Z = 8	0.13 × 0.12 × 0.09 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2203 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 28.1°, θ_min = 2.6°
ϕ and ω scans	h = −8→9
14904 measured reflections	k = −14→14
3050 independent reflections	l = −31→40

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) = 0.116	w = 1/[σ²(F_o²) + (0.0529P)² + 0.3952P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
3050 reflections	Δρ_max = 0.17 e Å⁻³
173 parameters	Δρ_min = −0.12 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: 0.0151 (14)

Crystal data top

C₁₆H₁₃FO₂	V = 2565 (3) Å³
M_r = 256.26	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.457 (4) Å	µ = 0.10 mm⁻¹
b = 11.072 (6) Å	T = 273 K
c = 31.063 (18) Å	0.13 × 0.12 × 0.09 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2203 reflections with I > 2σ(I)
14904 measured reflections	R_int = 0.039
3050 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.01	Δρ_max = 0.17 e Å⁻³
3050 reflections	Δρ_min = −0.12 e Å⁻³
173 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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
O2	0.19197 (16)	0.39463 (9)	0.32285 (3)	0.0679 (3)
O1	0.09858 (15)	0.57395 (10)	0.13185 (3)	0.0674 (3)
C16	0.15026 (17)	0.49647 (12)	0.31027 (4)	0.0497 (3)
C9	0.13654 (16)	0.52293 (11)	0.26375 (4)	0.0447 (3)
C15	0.06589 (19)	0.56911 (13)	0.38189 (5)	0.0567 (4)
H15A	0.0689	0.4883	0.3900	0.068*
C10	0.07845 (18)	0.63325 (11)	0.24765 (4)	0.0484 (3)
H10A	0.0485	0.6945	0.2668	0.058*
C12	0.10839 (18)	0.56345 (12)	0.17528 (4)	0.0504 (3)
F	−0.15021 (16)	0.89082 (12)	0.50973 (3)	0.1015 (4)
C14	0.10856 (19)	0.59300 (12)	0.34157 (4)	0.0535 (3)
H14A	0.1125	0.6731	0.3326	0.064*
C11	0.06382 (18)	0.65460 (12)	0.20395 (4)	0.0498 (3)
H11A	0.0246	0.7292	0.1939	0.060*
C4	0.0339 (2)	0.77956 (13)	0.41030 (4)	0.0578 (4)
H4A	0.0854	0.8098	0.3852	0.069*
C8	0.17978 (19)	0.43239 (12)	0.23404 (5)	0.0550 (4)
H8A	0.2185	0.3575	0.2439	0.066*
C7	0.1660 (2)	0.45230 (13)	0.19088 (5)	0.0600 (4)
H7A	0.1953	0.3910	0.1717	0.072*
C3	0.01471 (18)	0.65509 (13)	0.41510 (4)	0.0533 (3)
C5	−0.0214 (2)	0.85891 (16)	0.44174 (5)	0.0668 (4)
H5A	−0.0084	0.9418	0.4381	0.080*
C6	−0.0961 (2)	0.81261 (18)	0.47852 (5)	0.0702 (4)
C2	−0.0617 (2)	0.61339 (16)	0.45340 (5)	0.0682 (4)
H2A	−0.0753	0.5307	0.4576	0.082*
C13	0.0497 (2)	0.68788 (15)	0.11415 (5)	0.0679 (4)
H13A	0.0469	0.6822	0.0833	0.102*
H13B	0.1360	0.7477	0.1226	0.102*
H13C	−0.0667	0.7106	0.1246	0.102*
C1	−0.1175 (2)	0.69190 (19)	0.48511 (5)	0.0755 (5)
H1A	−0.1686	0.6631	0.5104	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0827 (8)	0.0466 (6)	0.0744 (7)	0.0011 (5)	−0.0083 (6)	0.0087 (5)
O1	0.0825 (8)	0.0703 (7)	0.0494 (6)	0.0061 (6)	−0.0002 (5)	−0.0128 (5)
C16	0.0457 (7)	0.0435 (7)	0.0600 (8)	−0.0068 (5)	−0.0021 (6)	0.0038 (6)
C9	0.0386 (6)	0.0389 (6)	0.0567 (7)	−0.0051 (5)	0.0001 (5)	−0.0038 (5)
C15	0.0590 (8)	0.0532 (8)	0.0578 (8)	−0.0064 (6)	−0.0015 (6)	0.0086 (6)
C10	0.0546 (7)	0.0400 (6)	0.0504 (7)	−0.0005 (5)	0.0041 (6)	−0.0071 (5)
C12	0.0474 (7)	0.0532 (8)	0.0508 (7)	−0.0031 (6)	0.0009 (6)	−0.0102 (6)
F	0.1113 (9)	0.1308 (10)	0.0624 (6)	0.0123 (7)	0.0144 (6)	−0.0209 (6)
C14	0.0613 (8)	0.0466 (7)	0.0525 (8)	−0.0033 (6)	−0.0038 (6)	0.0037 (6)
C11	0.0551 (8)	0.0425 (7)	0.0516 (7)	0.0011 (6)	0.0011 (6)	−0.0035 (5)
C4	0.0687 (9)	0.0642 (9)	0.0407 (7)	−0.0032 (7)	−0.0014 (6)	0.0075 (6)
C8	0.0549 (8)	0.0407 (7)	0.0693 (9)	0.0032 (6)	−0.0018 (6)	−0.0069 (6)
C7	0.0638 (9)	0.0497 (8)	0.0665 (9)	0.0064 (6)	0.0020 (7)	−0.0202 (7)
C3	0.0531 (7)	0.0624 (9)	0.0443 (7)	−0.0044 (6)	−0.0045 (6)	0.0098 (6)
C5	0.0815 (11)	0.0689 (10)	0.0501 (8)	0.0018 (8)	−0.0055 (7)	0.0013 (7)
C6	0.0671 (10)	0.0968 (13)	0.0467 (8)	0.0076 (9)	−0.0016 (7)	−0.0049 (8)
C2	0.0699 (10)	0.0777 (10)	0.0571 (9)	−0.0075 (8)	0.0018 (7)	0.0184 (8)
C13	0.0723 (10)	0.0804 (11)	0.0508 (8)	−0.0039 (8)	0.0007 (7)	−0.0011 (7)
C1	0.0704 (10)	0.1107 (15)	0.0454 (8)	−0.0035 (10)	0.0081 (7)	0.0135 (9)

Geometric parameters (Å, º) top

O2—C16	1.2334 (17)	C4—C5	1.377 (2)
O1—C12	1.3561 (18)	C4—C3	1.394 (2)
O1—C13	1.424 (2)	C4—H4A	0.9300
C16—C9	1.478 (2)	C8—C7	1.363 (2)
C16—C14	1.478 (2)	C8—H8A	0.9300
C9—C10	1.3892 (19)	C7—H7A	0.9300
C9—C8	1.4002 (19)	C3—C2	1.398 (2)
C15—C14	1.319 (2)	C5—C6	1.371 (2)
C15—C3	1.455 (2)	C5—H5A	0.9300
C15—H15A	0.9300	C6—C1	1.362 (3)
C10—C11	1.382 (2)	C2—C1	1.378 (3)
C10—H10A	0.9300	C2—H2A	0.9300
C12—C11	1.3864 (19)	C13—H13A	0.9600
C12—C7	1.391 (2)	C13—H13B	0.9600
F—C6	1.361 (2)	C13—H13C	0.9600
C14—H14A	0.9300	C1—H1A	0.9300
C11—H11A	0.9300

C12—O1—C13	118.30 (11)	C7—C8—H8A	119.5
O2—C16—C9	120.57 (12)	C9—C8—H8A	119.5
O2—C16—C14	120.38 (13)	C8—C7—C12	120.62 (12)
C9—C16—C14	119.03 (12)	C8—C7—H7A	119.7
C10—C9—C8	117.65 (13)	C12—C7—H7A	119.7
C10—C9—C16	123.23 (12)	C4—C3—C2	117.37 (14)
C8—C9—C16	119.11 (12)	C4—C3—C15	122.98 (12)
C14—C15—C3	127.26 (14)	C2—C3—C15	119.63 (14)
C14—C15—H15A	116.4	C6—C5—C4	118.32 (16)
C3—C15—H15A	116.4	C6—C5—H5A	120.8
C11—C10—C9	121.91 (12)	C4—C5—H5A	120.8
C11—C10—H10A	119.0	F—C6—C1	118.87 (15)
C9—C10—H10A	119.0	F—C6—C5	118.44 (18)
O1—C12—C11	124.31 (13)	C1—C6—C5	122.70 (16)
O1—C12—C7	116.05 (12)	C1—C2—C3	121.55 (16)
C11—C12—C7	119.64 (13)	C1—C2—H2A	119.2
C15—C14—C16	122.03 (13)	C3—C2—H2A	119.2
C15—C14—H14A	119.0	O1—C13—H13A	109.5
C16—C14—H14A	119.0	O1—C13—H13B	109.5
C10—C11—C12	119.17 (13)	H13A—C13—H13B	109.5
C10—C11—H11A	120.4	O1—C13—H13C	109.5
C12—C11—H11A	120.4	H13A—C13—H13C	109.5
C5—C4—C3	121.62 (14)	H13B—C13—H13C	109.5
C5—C4—H4A	119.2	C6—C1—C2	118.45 (15)
C3—C4—H4A	119.2	C6—C1—H1A	120.8
C7—C8—C9	121.01 (13)	C2—C1—H1A	120.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2ⁱ	0.93	2.50	3.376 (2)	158
C15—H15A···O2	0.93	2.50	2.825 (2)	101

Symmetry code: (i) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃FO₂
M_r	256.26
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	273
a, b, c (Å)	7.457 (4), 11.072 (6), 31.063 (18)
V (Å³)	2565 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.13 × 0.12 × 0.09

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14904, 3050, 2203
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.116, 1.01
No. of reflections	3050
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.12

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2ⁱ	0.93	2.50	3.376 (2)	157.7
C15—H15A···O2	0.93	2.50	2.825 (2)	100.5

Symmetry code: (i) −x, y+1/2, −z+1/2.

Acknowledgements

The authors thank the National Natural Science Foundation of Shandong (Y2007B14; Y2008B29) and Weifang University for research grants.

References

Anto, R. J., Kuttan, G., Kuttan, R., Sathyanarayana, K. & Rao, M. N. A. (1994). J. Clin. Biochem. Nutr. 17, 73–80. CrossRef CAS Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
De Vincenzo, R., Ferlini, C., Distefano, M., Gaggini, C., Riva, A., Bombardelli, E., Morazzoni, P., Valenti, P., Belluti, F., Ranelletti, F. O., Mancuso, S. & Scambia, G. (2000). Cancer Chemother. Pharmacol. 46, 305–312. Web of Science CrossRef PubMed CAS Google Scholar
Dimmock, J. R., Kandepu, N. M., Hetherington, M., Quail, J. W., Pugazhenthi, U., Sudom, A. M., Chamankhah, M., Rose, P., Pass, E., Allen, T. M., Halleran, S., Szydlowski, J., Mutus, B., Tannous, M., Manavathu, E. K., Myers, T. G., De Clercq, E. & Balzarini, J. (1998). J. Med. Chem. 41, 1014–1026. Web of Science CSD CrossRef CAS PubMed Google Scholar
Guo, H.-M., Liu, L. & Jian, F.-F. (2008). Acta Cryst. E64, o1626. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hsieh, H. K., Lee, T. H., Wang, J. P., Wang, J. J. & Lin, C. N. (1998). Pharm. Res. 15, 39–46. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar