(2E)-3-[4-(Dimethyl-amino)-phen-yl]-1-(4-fluoro-phen-yl)prop-2-en-1-one.

The mean planes of the two benzene rings in the title compound, C(17)H(16)FNO, are twisted slightly, making a dihedral angle of 7.8 (1)°. The prop-2-en-1-one group is also twisted slightly with a C-C-C-O torsion angle of -11.6 (3)°. In the crystal, weak inter-molecular C-H⋯O inter-actions link pairs of mol-ecules, forming centrosymmetric dimers.

Related literature

Chalcones are precursors of all flavonoid-type natural products in biosynthesis, see: Marais et al. (2005 ▶). For their pharmacological activity, see: Di Carlo et al. (1999 ▶) and for their anti­malarial activity, see: Ram et al. (2000 ▶); Troeberg et al. (2000 ▶). For the synthesis and biological activity of some fluorinated chalcone derivatives, see: Nakamura et al. (2002 ▶). For a review of anti-infective and anti-inflammatory chalcones, see: Nowakowska (2007 ▶) and for recent advances in therapeutic chalcones, see: Ni et al. (2004 ▶). For related structures, see: Butcher et al. (2006 ▶, 2007a ▶,b ▶); Harrison et al. (2006 ▶); Jasinski et al. (2009 ▶); Jing (2009 ▶); Sarojini et al. (2007 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H16FNO

M = 269.31

Monoclinic,

a = 12.8334 (3) Å

b = 12.3560 (2) Å

c = 9.3922 (2) Å

β = 105.965 (2)°

V = 1431.87 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.56 × 0.47 × 0.22 mm

Data collection

Oxford Diffraction Gemini R diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.675, T max = 1.000

6644 measured reflections

2929 independent reflections

2098 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.197

S = 1.10

2929 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000377/xu5139sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000377/xu5139Isup2.hkl

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

C17H16FNO	F(000) = 568
Mr = 269.31	Dx = 1.249 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3513 reflections
a = 12.8334 (3) Å	θ = 2.4–38.6°
b = 12.3560 (2) Å	µ = 0.09 mm−1
c = 9.3922 (2) Å	T = 295 K
β = 105.965 (2)°	Irregular triangular plate, yellow
V = 1431.87 (5) Å3	0.56 × 0.47 × 0.22 mm
Z = 4

Oxford Diffraction Gemini R diffractometer	2929 independent reflections
Radiation source: fine-focus sealed tube	2098 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 10.5081 pixels mm-1	θmax = 26.7°, θmin = 2.3°
φ and ω scans	h = −16→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −15→15
Tmin = 0.675, Tmax = 1.000	l = −11→11
6644 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.1067P)2 + 0.0852P] where P = (Fo2 + 2Fc2)/3
2929 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.13 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	1.15377 (18)	0.10045 (18)	1.0627 (2)	0.1881 (10)
O1	0.83748 (14)	0.47322 (14)	0.78907 (19)	0.1242 (6)
C1	0.92349 (14)	0.30455 (16)	0.8178 (2)	0.0850 (5)
C2	1.0044 (2)	0.3397 (2)	0.9375 (3)	0.1251 (9)
H2A	1.0064	0.4124	0.9635	0.150*
C3	1.0820 (3)	0.2720 (3)	1.0198 (4)	0.1402 (11)
H3A	1.1363	0.2978	1.0999	0.168*
C4	1.0777 (2)	0.1681 (3)	0.9820 (3)	0.1281 (9)
C5	0.9972 (3)	0.1257 (3)	0.8685 (4)	0.1464 (12)
H5A	0.9942	0.0519	0.8480	0.176*
C6	0.9209 (2)	0.1953 (2)	0.7859 (3)	0.1187 (8)
H6A	0.8665	0.1684	0.7068	0.142*
N1	0.36368 (14)	0.37392 (15)	−0.0182 (2)	0.0984 (5)
C7	0.84180 (15)	0.38300 (17)	0.7354 (2)	0.0894 (5)
C8	0.76857 (15)	0.35318 (16)	0.5923 (2)	0.0853 (5)
H8A	0.7756	0.2857	0.5520	0.102*
C9	0.69177 (16)	0.42082 (15)	0.5183 (2)	0.0861 (5)
H9A	0.6893	0.4870	0.5645	0.103*
C10	0.61231 (15)	0.40735 (14)	0.3784 (2)	0.0810 (5)
C11	0.60600 (15)	0.31682 (14)	0.2863 (2)	0.0831 (5)
H11A	0.6573	0.2621	0.3149	0.100*
C12	0.52677 (16)	0.30671 (15)	0.1558 (2)	0.0856 (5)
H12A	0.5265	0.2460	0.0972	0.103*
C13	0.44563 (15)	0.38556 (15)	0.1076 (2)	0.0828 (5)
C14	0.45373 (18)	0.47770 (16)	0.1973 (2)	0.0968 (6)
H14A	0.4037	0.5334	0.1684	0.116*
C15	0.53447 (19)	0.48642 (15)	0.3267 (2)	0.0963 (6)
H15A	0.5373	0.5488	0.3831	0.116*
C16	0.3540 (2)	0.2790 (2)	−0.1099 (3)	0.1289 (9)
H16A	0.4204	0.2681	−0.1364	0.193*
H16B	0.2955	0.2886	−0.1980	0.193*
H16C	0.3398	0.2171	−0.0563	0.193*
C17	0.2862 (2)	0.4610 (2)	−0.0696 (3)	0.1149 (7)
H17A	0.2522	0.4790	0.0065	0.172*
H17B	0.2321	0.4381	−0.1569	0.172*
H17C	0.3233	0.5234	−0.0922	0.172*

	U11	U22	U33	U12	U13	U23
F1	0.1983 (18)	0.1869 (19)	0.1399 (14)	0.0835 (16)	−0.0196 (14)	0.0050 (13)
O1	0.1291 (12)	0.1024 (11)	0.1227 (12)	0.0113 (9)	0.0033 (10)	−0.0346 (9)
C1	0.0812 (10)	0.0904 (12)	0.0836 (10)	−0.0030 (9)	0.0229 (8)	−0.0078 (9)
C2	0.1233 (17)	0.1070 (17)	0.1222 (18)	0.0007 (14)	−0.0045 (15)	−0.0236 (14)
C3	0.1254 (19)	0.138 (2)	0.125 (2)	0.0128 (18)	−0.0198 (16)	−0.0143 (18)
C4	0.1270 (18)	0.141 (2)	0.1022 (16)	0.0355 (17)	0.0072 (14)	0.0023 (16)
C5	0.176 (3)	0.1129 (19)	0.124 (2)	0.0376 (19)	−0.002 (2)	−0.0146 (16)
C6	0.1273 (17)	0.1016 (16)	0.1074 (15)	0.0120 (14)	−0.0010 (14)	−0.0146 (13)
N1	0.1038 (11)	0.0985 (12)	0.0866 (10)	0.0089 (9)	0.0158 (9)	0.0029 (8)
C7	0.0883 (11)	0.0872 (12)	0.0932 (11)	−0.0069 (9)	0.0257 (9)	−0.0135 (9)
C8	0.0905 (11)	0.0770 (10)	0.0880 (11)	−0.0035 (8)	0.0238 (9)	−0.0064 (8)
C9	0.0930 (11)	0.0749 (10)	0.0916 (11)	−0.0034 (8)	0.0275 (9)	−0.0068 (9)
C10	0.0902 (10)	0.0682 (9)	0.0866 (10)	−0.0003 (8)	0.0277 (9)	0.0002 (8)
C11	0.0892 (10)	0.0692 (9)	0.0913 (11)	0.0045 (8)	0.0253 (9)	0.0009 (8)
C12	0.0975 (11)	0.0703 (10)	0.0900 (11)	0.0007 (8)	0.0275 (9)	−0.0055 (8)
C13	0.0908 (10)	0.0794 (10)	0.0786 (10)	0.0002 (8)	0.0241 (8)	0.0067 (8)
C14	0.1093 (13)	0.0786 (11)	0.0981 (13)	0.0192 (10)	0.0211 (11)	0.0053 (10)
C15	0.1172 (14)	0.0709 (10)	0.0957 (12)	0.0115 (10)	0.0205 (11)	−0.0066 (9)
C16	0.1193 (17)	0.138 (2)	0.1126 (17)	0.0095 (16)	0.0036 (14)	−0.0324 (16)
C17	0.1095 (15)	0.1255 (19)	0.1013 (14)	0.0171 (14)	0.0150 (12)	0.0159 (13)

F1—C4	1.349 (3)	C9—C10	1.434 (3)
O1—C7	1.231 (2)	C9—H9A	0.9300
C1—C2	1.374 (3)	C10—C15	1.386 (3)
C1—C6	1.381 (3)	C10—C11	1.403 (2)
C1—C7	1.481 (3)	C11—C12	1.366 (3)
C2—C3	1.366 (4)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.407 (3)
C3—C4	1.330 (4)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.403 (3)
C4—C5	1.368 (4)	C14—C15	1.368 (3)
C5—C6	1.371 (4)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15A	0.9300
C6—H6A	0.9300	C16—H16A	0.9600
N1—C13	1.356 (3)	C16—H16B	0.9600
N1—C16	1.440 (3)	C16—H16C	0.9600
N1—C17	1.454 (3)	C17—H17A	0.9600
C7—C8	1.460 (3)	C17—H17B	0.9600
C8—C9	1.333 (3)	C17—H17C	0.9600
C8—H8A	0.9300
C2—C1—C6	117.0 (2)	C15—C10—C11	115.62 (17)
C2—C1—C7	119.2 (2)	C15—C10—C9	120.08 (17)
C6—C1—C7	123.72 (19)	C11—C10—C9	124.30 (17)
C3—C2—C1	122.6 (3)	C12—C11—C10	121.92 (17)
C3—C2—H2A	118.7	C12—C11—H11A	119.0
C1—C2—H2A	118.7	C10—C11—H11A	119.0
C4—C3—C2	118.0 (3)	C11—C12—C13	121.86 (17)
C4—C3—H3A	121.0	C11—C12—H12A	119.1
C2—C3—H3A	121.0	C13—C12—H12A	119.1
C3—C4—F1	118.5 (3)	N1—C13—C14	121.39 (17)
C3—C4—C5	123.0 (3)	N1—C13—C12	122.34 (18)
F1—C4—C5	118.4 (3)	C14—C13—C12	116.27 (17)
C4—C5—C6	118.0 (3)	C15—C14—C13	120.71 (18)
C4—C5—H5A	121.0	C15—C14—H14A	119.6
C6—C5—H5A	121.0	C13—C14—H14A	119.6
C5—C6—C1	121.3 (2)	C14—C15—C10	123.54 (18)
C5—C6—H6A	119.3	C14—C15—H15A	118.2
C1—C6—H6A	119.3	C10—C15—H15A	118.2
C13—N1—C16	121.72 (19)	N1—C16—H16A	109.5
C13—N1—C17	120.40 (18)	N1—C16—H16B	109.5
C16—N1—C17	117.76 (19)	H16A—C16—H16B	109.5
O1—C7—C8	121.0 (2)	N1—C16—H16C	109.5
O1—C7—C1	118.93 (18)	H16A—C16—H16C	109.5
C8—C7—C1	120.03 (17)	H16B—C16—H16C	109.5
C9—C8—C7	121.22 (18)	N1—C17—H17A	109.5
C9—C8—H8A	119.4	N1—C17—H17B	109.5
C7—C8—H8A	119.4	H17A—C17—H17B	109.5
C8—C9—C10	129.98 (18)	N1—C17—H17C	109.5
C8—C9—H9A	115.0	H17A—C17—H17C	109.5
C10—C9—H9A	115.0	H17B—C17—H17C	109.5
C6—C1—C2—C3	2.2 (4)	C8—C9—C10—C15	175.4 (2)
C7—C1—C2—C3	179.4 (3)	C8—C9—C10—C11	−4.1 (3)
C1—C2—C3—C4	−0.5 (5)	C15—C10—C11—C12	−1.3 (3)
C2—C3—C4—F1	−179.8 (3)	C9—C10—C11—C12	178.19 (17)
C2—C3—C4—C5	−2.5 (6)	C10—C11—C12—C13	−1.2 (3)
C3—C4—C5—C6	3.4 (5)	C16—N1—C13—C14	−179.2 (2)
F1—C4—C5—C6	−179.2 (3)	C17—N1—C13—C14	4.7 (3)
C4—C5—C6—C1	−1.5 (5)	C16—N1—C13—C12	0.7 (3)
C2—C1—C6—C5	−1.2 (4)	C17—N1—C13—C12	−175.38 (19)
C7—C1—C6—C5	−178.2 (2)	C11—C12—C13—N1	−176.80 (18)
C2—C1—C7—O1	−11.6 (3)	C11—C12—C13—C14	3.1 (3)
C6—C1—C7—O1	165.4 (2)	N1—C13—C14—C15	177.5 (2)
C2—C1—C7—C8	167.9 (2)	C12—C13—C14—C15	−2.4 (3)
C6—C1—C7—C8	−15.1 (3)	C13—C14—C15—C10	−0.1 (3)
O1—C7—C8—C9	−2.9 (3)	C11—C10—C15—C14	2.0 (3)
C1—C7—C8—C9	177.56 (17)	C9—C10—C15—C14	−177.53 (19)
C7—C8—C9—C10	−179.71 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O1i	0.96	2.56	3.525 (3)	180

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O1i	0.96	2.56	3.525 (3)	180

Symmetry code: (i) .