3-(4-Fluoro-phen-yl)-1-(4-methoxy-phen-yl)prop-2-en-1-one.

The title compound, C(16)H(13)FO(2), was prepared from 4-methoxy-hypnone and 4-fluoro-benzophenone 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 inter-molecular C-H⋯O hydrogen-bonding inter-actions.

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 = 256.26

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.116

S = 1.01

3050 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.12 e Å−3

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.

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

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

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

C16H13FO2	F(000) = 1072
Mr = 256.26	Dx = 1.327 Mg m−3Dm = 1.327 Mg m−3Dm 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

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

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(Fo2) + (0.0529P)2 + 0.3952P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
3050 reflections	Δρmax = 0.17 e Å−3
173 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) .