3-(2-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 2-fluoro-benzophenone by a Claisen-Schmidt condensation reaction. The dihedral angle between the two benzene rings is 31.99 (2)°. In the crystal structure, mol-ecules are linked by weak inter-molecular 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 = 256.26

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.05

3162 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.19 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/S1600536809045759/lh2941sup1.cif

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

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

C16H13FO2	F(000) = 1072
Mr = 256.26	Dx = 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

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

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(Fo2) + (0.0479P)2 + 0.3713P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3162 reflections	Δρmax = 0.16 e Å−3
173 parameters	Δρmin = −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)

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
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*

	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)

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

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

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) .