(E)-3-(4-Fluoro-phen-yl)-1-phenyl-2-propen-1-one.

In the title compound, C(15)H(11)FO, the configuration of the keto group with respect to the olefinic double bond is s-cis. The dihedral angle between the planes of the two benzene rings is 10.61 (10)°. The crystal packing is stabilized by C-H⋯π inter-actions involving both benzene rings.

Related literature

For the synthesis, see: Chimenti et al. (2008 ▶). For the biological activity of chalcone derivatives, see: Dimmock et al. (1999 ▶).

Experimental

Crystal data

C15H11FO

M = 226.24

Monoclinic,

a = 24.926 (9) Å

b = 5.6940 (19) Å

c = 7.749 (3) Å

β = 94.747 (5)°

V = 1096.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 93 K

0.40 × 0.33 × 0.30 mm

Data collection

Rigaku SPIDER diffractometer

Absorption correction: none

4214 measured reflections

1256 independent reflections

1174 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.066

S = 1.05

1256 reflections

154 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.14 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037635/ci2914sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037635/ci2914Isup2.hkl

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

C15H11FO	F(000) = 472
Mr = 226.24	Dx = 1.371 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1803 reflections
a = 24.926 (9) Å	θ = 3.2–27.5°
b = 5.6940 (19) Å	µ = 0.10 mm−1
c = 7.749 (3) Å	T = 93 K
β = 94.747 (5)°	Block, colourless
V = 1096.0 (6) Å3	0.40 × 0.33 × 0.30 mm
Z = 4

Rigaku SPIDER diffractometer	1174 reflections with I > 2σ(I)
Radiation source: Rotating anode	Rint = 0.027
graphite	θmax = 27.5°, θmin = 3.3°
ω scans	h = −32→32
4214 measured reflections	k = −7→6
1256 independent reflections	l = −10→9

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.02P)2 + 0.6P] where P = (Fo2 + 2Fc2)/3
1256 reflections	(Δ/σ)max = 0.010
154 parameters	Δρmax = 0.20 e Å−3
2 restraints	Δρmin = −0.14 e Å−3

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
F1	0.78252 (5)	−0.0769 (2)	0.41272 (15)	0.0283 (3)
O1	0.54146 (6)	0.8936 (3)	0.5750 (2)	0.0298 (4)
C1	0.43870 (9)	0.9349 (4)	0.4181 (3)	0.0201 (5)
H1	0.4526	1.0584	0.4912	0.024*
C2	0.38614 (9)	0.9458 (4)	0.3436 (3)	0.0224 (5)
H2	0.3642	1.0767	0.3660	0.027*
C3	0.36564 (8)	0.7667 (4)	0.2369 (3)	0.0220 (5)
H3	0.3296	0.7749	0.1868	0.026*
C4	0.39742 (9)	0.5758 (4)	0.2026 (3)	0.0222 (5)
H4	0.3834	0.4539	0.1282	0.027*
C5	0.45022 (9)	0.5632 (4)	0.2780 (3)	0.0205 (5)
H5	0.4720	0.4315	0.2555	0.025*
C6	0.47111 (8)	0.7420 (4)	0.3855 (3)	0.0180 (4)
C7	0.52705 (8)	0.7380 (4)	0.4726 (3)	0.0205 (4)
C8	0.56390 (9)	0.5435 (4)	0.4363 (3)	0.0217 (5)
H8	0.5512	0.4142	0.3669	0.026*
C9	0.61504 (8)	0.5513 (4)	0.5016 (3)	0.0199 (4)
H9	0.6250	0.6836	0.5718	0.024*
C10	0.65773 (9)	0.3806 (4)	0.4783 (3)	0.0185 (4)
C11	0.64836 (9)	0.1657 (4)	0.3938 (3)	0.0214 (5)
H11	0.6127	0.1239	0.3526	0.026*
C12	0.69023 (9)	0.0130 (4)	0.3692 (3)	0.0225 (5)
H12	0.6838	−0.1310	0.3091	0.027*
C13	0.74170 (9)	0.0754 (4)	0.4343 (3)	0.0211 (5)
C14	0.75290 (8)	0.2834 (4)	0.5203 (3)	0.0212 (4)
H14	0.7886	0.3216	0.5635	0.025*
C15	0.71063 (9)	0.4355 (4)	0.5420 (3)	0.0207 (4)
H15	0.7176	0.5799	0.6012	0.025*

	U11	U22	U33	U12	U13	U23
F1	0.0222 (7)	0.0284 (7)	0.0342 (8)	0.0079 (6)	0.0022 (5)	0.0009 (6)
O1	0.0228 (8)	0.0330 (9)	0.0326 (9)	0.0047 (7)	−0.0034 (7)	−0.0121 (8)
C1	0.0228 (11)	0.0192 (11)	0.0185 (11)	−0.0002 (9)	0.0021 (8)	−0.0011 (9)
C2	0.0221 (11)	0.0227 (11)	0.0227 (11)	0.0043 (9)	0.0032 (9)	0.0017 (9)
C3	0.0177 (10)	0.0265 (11)	0.0218 (11)	0.0006 (9)	0.0017 (9)	0.0031 (9)
C4	0.0218 (11)	0.0232 (11)	0.0215 (11)	−0.0036 (9)	0.0012 (8)	−0.0011 (9)
C5	0.0218 (11)	0.0205 (11)	0.0196 (10)	0.0027 (9)	0.0046 (9)	0.0002 (9)
C6	0.0177 (10)	0.0206 (11)	0.0161 (10)	0.0007 (8)	0.0031 (8)	0.0028 (8)
C7	0.0187 (10)	0.0230 (11)	0.0199 (10)	0.0001 (9)	0.0026 (8)	0.0005 (9)
C8	0.0228 (10)	0.0215 (11)	0.0206 (10)	0.0014 (9)	0.0012 (8)	−0.0019 (9)
C9	0.0209 (10)	0.0209 (11)	0.0178 (10)	0.0023 (9)	0.0012 (8)	−0.0003 (9)
C10	0.0179 (10)	0.0210 (10)	0.0163 (10)	0.0021 (9)	0.0004 (8)	0.0033 (9)
C11	0.0177 (10)	0.0249 (11)	0.0211 (11)	−0.0018 (9)	−0.0013 (8)	0.0021 (9)
C12	0.0247 (11)	0.0222 (11)	0.0206 (11)	0.0014 (9)	0.0012 (9)	0.0005 (9)
C13	0.0191 (11)	0.0229 (11)	0.0217 (12)	0.0047 (9)	0.0040 (8)	0.0042 (9)
C14	0.0155 (10)	0.0259 (11)	0.0218 (10)	−0.0017 (9)	−0.0005 (8)	0.0030 (10)
C15	0.0214 (11)	0.0204 (10)	0.0199 (11)	−0.0005 (9)	−0.0009 (8)	0.0004 (9)

F1—C13	1.358 (2)	C8—C9	1.333 (3)
O1—C7	1.223 (3)	C8—H8	0.95
C1—C2	1.389 (3)	C9—C10	1.463 (3)
C1—C6	1.399 (3)	C9—H9	0.95
C1—H1	0.95	C10—C11	1.398 (3)
C2—C3	1.384 (3)	C10—C15	1.404 (3)
C2—H2	0.95	C11—C12	1.383 (3)
C3—C4	1.384 (3)	C11—H11	0.95
C3—H3	0.95	C12—C13	1.386 (3)
C4—C5	1.397 (3)	C12—H12	0.95
C4—H4	0.95	C13—C14	1.376 (3)
C5—C6	1.389 (3)	C14—C15	1.385 (3)
C5—H5	0.95	C14—H14	0.95
C6—C7	1.498 (3)	C15—H15	0.95
C7—C8	1.481 (3)
C2—C1—C6	119.9 (2)	C7—C8—H8	120.3
C2—C1—H1	120.0	C8—C9—C10	127.8 (2)
C6—C1—H1	120.0	C8—C9—H9	116.1
C3—C2—C1	120.3 (2)	C10—C9—H9	116.1
C3—C2—H2	119.8	C11—C10—C15	118.37 (19)
C1—C2—H2	119.8	C11—C10—C9	122.95 (19)
C2—C3—C4	120.3 (2)	C15—C10—C9	118.68 (19)
C2—C3—H3	119.8	C12—C11—C10	121.0 (2)
C4—C3—H3	119.8	C12—C11—H11	119.5
C3—C4—C5	119.6 (2)	C10—C11—H11	119.5
C3—C4—H4	120.2	C11—C12—C13	118.4 (2)
C5—C4—H4	120.2	C11—C12—H12	120.8
C6—C5—C4	120.43 (19)	C13—C12—H12	120.8
C6—C5—H5	119.8	F1—C13—C14	119.03 (19)
C4—C5—H5	119.8	F1—C13—C12	118.19 (19)
C5—C6—C1	119.37 (19)	C14—C13—C12	122.8 (2)
C5—C6—C7	123.20 (18)	C13—C14—C15	118.11 (19)
C1—C6—C7	117.42 (18)	C13—C14—H14	120.9
O1—C7—C8	120.79 (19)	C15—C14—H14	120.9
O1—C7—C6	119.56 (19)	C14—C15—C10	121.3 (2)
C8—C7—C6	119.64 (18)	C14—C15—H15	119.3
C9—C8—C7	119.4 (2)	C10—C15—H15	119.3
C9—C8—H8	120.3
C6—C1—C2—C3	−0.1 (3)	C7—C8—C9—C10	−178.7 (2)
C1—C2—C3—C4	−0.3 (3)	C8—C9—C10—C11	−6.7 (3)
C2—C3—C4—C5	0.7 (3)	C8—C9—C10—C15	172.6 (2)
C3—C4—C5—C6	−0.6 (3)	C15—C10—C11—C12	−1.7 (3)
C4—C5—C6—C1	0.2 (3)	C9—C10—C11—C12	177.7 (2)
C4—C5—C6—C7	179.0 (2)	C10—C11—C12—C13	1.6 (3)
C2—C1—C6—C5	0.2 (3)	C11—C12—C13—F1	178.78 (19)
C2—C1—C6—C7	−178.7 (2)	C11—C12—C13—C14	−0.8 (3)
C5—C6—C7—O1	−175.0 (2)	F1—C13—C14—C15	−179.54 (18)
C1—C6—C7—O1	3.9 (3)	C12—C13—C14—C15	0.0 (3)
C5—C6—C7—C8	4.0 (3)	C13—C14—C15—C10	−0.1 (3)
C1—C6—C7—C8	−177.2 (2)	C11—C10—C15—C14	0.9 (3)
O1—C7—C8—C9	−7.1 (3)	C9—C10—C15—C14	−178.5 (2)
C6—C7—C8—C9	174.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cg1i	0.95	2.89	3.592 (3)	132
C4—H4···Cg1ii	0.95	2.93	3.646 (6)	133
C12—H12···Cg2iii	0.95	2.85	3.505 (8)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cg1i	0.95	2.89	3.592 (3)	132
C4—H4⋯Cg1ii	0.95	2.93	3.646 (6)	133
C12—H12⋯Cg2iii	0.95	2.85	3.505 (8)	127

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.