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

Guo, H.-M.

doi:10.1107/S1600536809045759

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3013

doi:10.1107/S1600536809045759

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

Huan-Mei Guo ^a ^*

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 27 October 2009; accepted 31 October 2009; online 7 November 2009)

The title compound, C₁₆H₁₃FO₂, was prepared from 4-methoxyhypnone and 2-fluorobenzophenone by a Claisen–Schmidt condensation reaction. The dihedral angle between the two benzene rings is 31.99 (2)°. In the crystal structure, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds along [010].

Related literature

For the biological activity of chalcones, see: Hsieh et al. (1998 ); Anto et al. (1994 ); De Vincenzo et al. (2000 ); Dimmock et al. (1998 ). For related structures, see: Fun et al. (2008 ); Zhao et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₃FO₂
M_r = 256.26
Orthorhombic, P b c a
a = 7.4511 (6) Å
b = 11.0541 (8) Å
c = 31.031 (3) Å
V = 2555.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
15509 measured reflections
3162 independent reflections
2162 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.117
S = 1.05
3162 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.19 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	2.51	3.3679 (18)	153
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/S1600536809045759/lh2941sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045759/lh2941Isup2.hkl

checkCIF report

Comment top

Chalcones have been identified as interesting compounds having multiple biological activities which include antiinflammatory (Hsieh et al.,1998) and antioxidant (Anto et al.,1994). The effectiveness of chalcone compounds against 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 herein.

The molecular structure of (I) is shown in Fig.1. The dihedral angle between the two benzene rings (C1—C6 and C7—C12) is 31.99 (2)°. The bond lengths and bond angles are within normal ranges and comparable to those in a related structures (Fun et al., 2008; Zhao et al., 2009). In the crystal structure, molecules are linked by weak intermolecular C-H···O hydrogen bonds into one-dimensional chains along [010] (Fig. 2).

Related literature top

For the biological activity of chalcones, see: Hsieh et al. (1998); Anto et al. (1994); De Vincenzo et al. (2000); Dimmock et al. (1998). For related structures, see: Fun et al. (2008); Zhao et al. (2009).

Experimental top

A mixture of 4-methoxyhypnone (0.02 mol) and 2-fluorobenzophenone (0.02 mol) and 10% NaOH (10ml) was stirred in ethanol (30 ml) for 2 h to afford the title compound (yield 85%). Single crystals suitable for X-ray measurements were obtailed by recrystallization of an ethyl acetate solution of the title compound 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 30% probability level.

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

Crystal data top

C₁₆H₁₃FO₂	F(000) = 1072
M_r = 256.26	D_x = 1.332 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2162 reflections
a = 7.4511 (6) Å	θ = 2.6–28.4°
b = 11.0541 (8) Å	µ = 0.10 mm⁻¹
c = 31.031 (3) Å	T = 298 K
V = 2555.9 (3) Å³	Bar, yellow
Z = 8	0.30 × 0.20 × 0.15 mm

Data collection top

Bruker SMART CCD diffractometer	2162 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 28.4°, θ_min = 2.6°
ϕ and ω scans	h = −8→9
15509 measured reflections	k = −13→14
3162 independent reflections	l = −39→36

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0479P)² + 0.3713P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3162 reflections	Δρ_max = 0.16 e Å⁻³
173 parameters	Δρ_min = −0.19 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: 0.0083 (9)

Crystal data top

C₁₆H₁₃FO₂	V = 2555.9 (3) Å³
M_r = 256.26	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.4511 (6) Å	µ = 0.10 mm⁻¹
b = 11.0541 (8) Å	T = 298 K
c = 31.031 (3) Å	0.30 × 0.20 × 0.15 mm

Data collection top

Bruker SMART CCD diffractometer	2162 reflections with I > 2σ(I)
15509 measured reflections	R_int = 0.026
3162 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.05	Δρ_max = 0.16 e Å⁻³
3162 reflections	Δρ_min = −0.19 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
C9	0.14251 (16)	0.07378 (11)	0.24089 (4)	0.0474 (3)
C16	0.16025 (17)	0.04544 (11)	0.19449 (5)	0.0530 (3)
O2	0.20708 (16)	−0.05586 (9)	0.18272 (3)	0.0723 (3)
C11	0.06705 (19)	0.20676 (12)	0.30007 (4)	0.0539 (3)
H11A	0.0271	0.2817	0.3097	0.065*
C10	0.08333 (18)	0.18431 (11)	0.25647 (4)	0.0507 (3)
H10A	0.0537	0.2451	0.2370	0.061*
C12	0.11063 (18)	0.11693 (12)	0.32916 (4)	0.0548 (3)
C15	0.0866 (2)	0.11137 (13)	0.12171 (5)	0.0598 (4)
H15A	0.1029	0.0307	0.1142	0.072*
C14	0.11574 (19)	0.13923 (12)	0.16225 (5)	0.0565 (4)
H14A	0.1082	0.2197	0.1709	0.068*
O1	0.09938 (16)	0.12870 (10)	0.37267 (3)	0.0747 (3)
C4	0.03134 (19)	0.19281 (13)	0.08723 (4)	0.0567 (4)
C8	0.1842 (2)	−0.01562 (12)	0.27107 (5)	0.0597 (4)
H8A	0.2232	−0.0909	0.2616	0.072*
F	−0.04947 (18)	0.02464 (10)	0.04543 (3)	0.1056 (4)
C7	0.1688 (2)	0.00549 (13)	0.31425 (5)	0.0656 (4)
H7A	0.1975	−0.0553	0.3338	0.079*
C5	0.0374 (2)	0.31898 (13)	0.09031 (5)	0.0638 (4)
H5A	0.0862	0.3546	0.1148	0.077*
C3	−0.0402 (2)	0.14689 (15)	0.04940 (5)	0.0698 (4)
C6	−0.0271 (3)	0.39113 (16)	0.05794 (5)	0.0783 (5)
H6A	−0.0227	0.4748	0.0608	0.094*
C13	0.0495 (2)	0.24277 (16)	0.39010 (5)	0.0743 (5)
H13A	0.0465	0.2376	0.4210	0.112*
H13B	−0.0671	0.2649	0.3796	0.112*
H13C	0.1354	0.3028	0.3815	0.112*
C2	−0.1052 (3)	0.21693 (19)	0.01653 (5)	0.0822 (5)
H2A	−0.1525	0.1818	−0.0082	0.099*
C1	−0.0987 (3)	0.3404 (2)	0.02105 (5)	0.0849 (5)
H1A	−0.1426	0.3900	−0.0008	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C9	0.0380 (6)	0.0385 (6)	0.0657 (8)	−0.0049 (5)	−0.0016 (5)	0.0041 (5)
C16	0.0447 (7)	0.0411 (7)	0.0731 (9)	−0.0071 (5)	0.0028 (6)	−0.0035 (6)
O2	0.0834 (8)	0.0458 (6)	0.0876 (8)	0.0051 (5)	0.0089 (6)	−0.0080 (5)
C11	0.0565 (8)	0.0436 (7)	0.0616 (8)	−0.0001 (6)	−0.0029 (6)	0.0026 (6)
C10	0.0531 (8)	0.0393 (6)	0.0597 (8)	−0.0011 (6)	−0.0050 (6)	0.0066 (5)
C12	0.0481 (7)	0.0579 (8)	0.0585 (8)	−0.0039 (6)	−0.0017 (6)	0.0110 (6)
C15	0.0627 (9)	0.0495 (7)	0.0672 (9)	−0.0063 (7)	0.0071 (7)	−0.0087 (6)
C14	0.0617 (9)	0.0461 (7)	0.0616 (8)	−0.0032 (6)	0.0036 (6)	−0.0055 (6)
O1	0.0864 (8)	0.0769 (7)	0.0608 (7)	0.0062 (6)	−0.0007 (5)	0.0141 (5)
C4	0.0545 (8)	0.0621 (8)	0.0535 (8)	−0.0062 (7)	0.0087 (6)	−0.0085 (6)
C8	0.0562 (8)	0.0419 (7)	0.0809 (10)	0.0065 (6)	0.0026 (7)	0.0073 (6)
F	0.1581 (12)	0.0820 (7)	0.0768 (7)	−0.0307 (7)	−0.0027 (6)	−0.0256 (5)
C7	0.0654 (9)	0.0541 (8)	0.0773 (10)	0.0088 (7)	−0.0005 (8)	0.0223 (7)
C5	0.0702 (10)	0.0624 (9)	0.0587 (8)	−0.0028 (8)	0.0039 (7)	−0.0065 (7)
C3	0.0782 (11)	0.0721 (10)	0.0592 (9)	−0.0144 (8)	0.0106 (8)	−0.0159 (8)
C6	0.0958 (13)	0.0692 (10)	0.0698 (10)	0.0077 (9)	0.0080 (9)	0.0008 (8)
C13	0.0755 (11)	0.0871 (12)	0.0604 (9)	−0.0049 (9)	−0.0012 (8)	0.0005 (8)
C2	0.0839 (12)	0.1103 (15)	0.0525 (9)	−0.0108 (11)	0.0016 (8)	−0.0104 (9)
C1	0.0877 (13)	0.1064 (15)	0.0607 (10)	0.0128 (11)	0.0051 (9)	0.0075 (10)

Geometric parameters (Å, º) top

C9—C10	1.3859 (18)	C4—C5	1.399 (2)
C9—C8	1.3964 (18)	C8—C7	1.365 (2)
C9—C16	1.4794 (19)	C8—H8A	0.9300
C16—O2	1.2285 (15)	F—C3	1.3587 (19)
C16—C14	1.478 (2)	C7—H7A	0.9300
C11—C12	1.3807 (18)	C5—C6	1.370 (2)
C11—C10	1.3808 (19)	C5—H5A	0.9300
C11—H11A	0.9300	C3—C2	1.369 (2)
C10—H10A	0.9300	C6—C1	1.382 (2)
C12—O1	1.3591 (17)	C6—H6A	0.9300
C12—C7	1.385 (2)	C13—H13A	0.9600
C15—C14	1.3134 (19)	C13—H13B	0.9600
C15—C4	1.457 (2)	C13—H13C	0.9600
C15—H15A	0.9300	C2—C1	1.373 (3)
C14—H14A	0.9300	C2—H2A	0.9300
O1—C13	1.421 (2)	C1—H1A	0.9300
C4—C3	1.386 (2)

C10—C9—C8	117.44 (13)	C7—C8—H8A	119.4
C10—C9—C16	123.68 (12)	C9—C8—H8A	119.4
C8—C9—C16	118.87 (12)	C8—C7—C12	120.40 (13)
O2—C16—C14	120.11 (13)	C8—C7—H7A	119.8
O2—C16—C9	120.52 (13)	C12—C7—H7A	119.8
C14—C16—C9	119.34 (11)	C6—C5—C4	121.29 (15)
C12—C11—C10	119.38 (13)	C6—C5—H5A	119.4
C12—C11—H11A	120.3	C4—C5—H5A	119.4
C10—C11—H11A	120.3	F—C3—C2	118.48 (15)
C11—C10—C9	121.88 (12)	F—C3—C4	117.44 (15)
C11—C10—H10A	119.1	C2—C3—C4	124.06 (16)
C9—C10—H10A	119.1	C5—C6—C1	120.44 (17)
O1—C12—C11	124.49 (13)	C5—C6—H6A	119.8
O1—C12—C7	115.86 (12)	C1—C6—H6A	119.8
C11—C12—C7	119.65 (13)	O1—C13—H13A	109.5
C14—C15—C4	127.23 (13)	O1—C13—H13B	109.5
C14—C15—H15A	116.4	H13A—C13—H13B	109.5
C4—C15—H15A	116.4	O1—C13—H13C	109.5
C15—C14—C16	121.39 (13)	H13A—C13—H13C	109.5
C15—C14—H14A	119.3	H13B—C13—H13C	109.5
C16—C14—H14A	119.3	C3—C2—C1	118.28 (16)
C12—O1—C13	118.62 (12)	C3—C2—H2A	120.9
C3—C4—C5	115.82 (14)	C1—C2—H2A	120.9
C3—C4—C15	120.28 (14)	C2—C1—C6	120.11 (17)
C5—C4—C15	123.83 (13)	C2—C1—H1A	119.9
C7—C8—C9	121.24 (13)	C6—C1—H1A	119.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2ⁱ	0.93	2.51	3.3679 (18)	153

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)	298
a, b, c (Å)	7.4511 (6), 11.0541 (8), 31.031 (3)
V (Å³)	2555.9 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15509, 3162, 2162
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.117, 1.05
No. of reflections	3162
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.19

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	2.51	3.3679 (18)	152.6

Symmetry code: (i) −x, y+1/2, −z+1/2.

Acknowledgements

The author would like to thank the Natural Science Foundation of Shandong Province (Y2008B29) and the Yuan-Du Scholar Fund of Weifang City.

References

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