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

The title compound, C(16)H(13)FO, adopts an E configuration with respect to the C=C bond of the propenone unit. The dihedral angle between the two benzene rings is 47.0 (5)°. Intra-molecular C-H⋯O hydrogen bonds generate an S(5) ring motif. In the crystal structure, mol-ecules are packed into columns along the c axis and the structure is stabilized by weak intra-molecular C-H⋯O hydrogen bonds and inter-molecular C-H⋯π inter-actions involving both aromatic rings.

Related literature

For applications of chalcones in non-linear optics, see, for example, Agrinskaya et al. (1999 ▶); Gu et al. (2008 ▶); Patil et al. (2007a ▶,b ▶,c ▶). For related structures see: Patil et al. (2007a ▶,b ▶,c ▶). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H13FO

M = 240.93

Monoclinic,

a = 14.505 (2) Å

b = 14.0523 (18) Å

c = 5.8382 (8) Å

β = 92.042 (10)°

V = 1189.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100.0 (1) K

0.47 × 0.15 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.913, T max = 0.993

14807 measured reflections

3442 independent reflections

2256 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.141

S = 1.07

3442 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011483/sj2485sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011483/sj2485Isup2.hkl

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

C16H13FO	F000 = 504
Mr = 240.93	Dx = 1.342 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1943 reflections
a = 14.505 (2) Å	θ = 2.8–34.6º
b = 14.0523 (18) Å	µ = 0.09 mm−1
c = 5.8382 (8) Å	T = 100.0 (1) K
β = 92.042 (10)º	Plate, colourless
V = 1189.3 (3) Å3	0.47 × 0.15 × 0.07 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3442 independent reflections
Radiation source: fine-focus sealed tube	2256 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.050
T = 100.0(1) K	θmax = 30.0º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −20→16
Tmin = 0.913, Tmax = 0.993	k = −19→15
14807 measured reflections	l = −8→8

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)] = 0.055	H-atom parameters constrained
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.0591P)2 + 0.1964P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3442 reflections	Δρmax = 0.36 e Å−3
164 parameters	Δρmin = −0.26 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.13263 (6)	0.62202 (8)	0.22333 (18)	0.0335 (3)
O1	0.52448 (8)	0.62178 (9)	−0.19348 (19)	0.0299 (3)
C1	0.37893 (11)	0.59097 (11)	0.2869 (3)	0.0223 (3)
H1A	0.4227	0.5697	0.3955	0.027*
C2	0.28643 (11)	0.58906 (11)	0.3360 (3)	0.0226 (4)
H2A	0.2671	0.5657	0.4754	0.027*
C3	0.22364 (11)	0.62262 (11)	0.1734 (3)	0.0225 (4)
C4	0.24829 (11)	0.65754 (11)	−0.0361 (3)	0.0235 (4)
H4A	0.2041	0.6804	−0.1415	0.028*
C5	0.34102 (11)	0.65749 (11)	−0.0847 (3)	0.0211 (3)
H5A	0.3594	0.6797	−0.2260	0.025*
C6	0.40712 (10)	0.62458 (11)	0.0752 (3)	0.0193 (3)
C7	0.50568 (11)	0.62320 (11)	0.0105 (3)	0.0220 (3)
C8	0.57812 (11)	0.62535 (11)	0.1937 (3)	0.0229 (3)
H8A	0.5628	0.6413	0.3423	0.027*
C9	0.66551 (11)	0.60475 (11)	0.1492 (3)	0.0203 (3)
H9A	0.6764	0.5840	0.0014	0.024*
C10	0.74563 (10)	0.61113 (10)	0.3059 (3)	0.0192 (3)
C11	0.83138 (10)	0.57998 (11)	0.2337 (3)	0.0202 (3)
H11A	0.8354	0.5513	0.0908	0.024*
C12	0.91061 (11)	0.59096 (11)	0.3709 (3)	0.0216 (3)
H12A	0.9668	0.5695	0.3189	0.026*
C13	0.90722 (11)	0.63365 (11)	0.5856 (3)	0.0211 (3)
C14	0.82142 (11)	0.66329 (11)	0.6599 (3)	0.0210 (3)
H14A	0.8176	0.6913	0.8037	0.025*
C15	0.74201 (11)	0.65200 (11)	0.5248 (3)	0.0207 (3)
H15A	0.6856	0.6717	0.5795	0.025*
C16	0.99320 (12)	0.64989 (13)	0.7314 (3)	0.0290 (4)
H16A	1.0451	0.6225	0.6577	0.044*
H16B	0.9866	0.6205	0.8784	0.044*
H16C	1.0029	0.7170	0.7512	0.044*

	U11	U22	U33	U12	U13	U23
F1	0.0209 (5)	0.0457 (7)	0.0340 (6)	−0.0022 (4)	0.0031 (4)	0.0022 (5)
O1	0.0265 (6)	0.0434 (8)	0.0196 (6)	0.0016 (5)	0.0013 (5)	−0.0004 (5)
C1	0.0258 (8)	0.0201 (8)	0.0207 (8)	0.0015 (6)	−0.0029 (6)	−0.0004 (6)
C2	0.0279 (8)	0.0209 (8)	0.0192 (8)	−0.0029 (6)	0.0017 (6)	0.0011 (6)
C3	0.0198 (8)	0.0213 (8)	0.0264 (9)	−0.0011 (6)	0.0016 (6)	−0.0017 (7)
C4	0.0240 (8)	0.0235 (8)	0.0226 (8)	−0.0001 (6)	−0.0044 (6)	0.0007 (7)
C5	0.0256 (8)	0.0215 (8)	0.0160 (8)	−0.0026 (6)	−0.0013 (6)	0.0001 (6)
C6	0.0216 (8)	0.0178 (8)	0.0184 (8)	0.0012 (6)	−0.0011 (6)	−0.0024 (6)
C7	0.0243 (8)	0.0213 (8)	0.0203 (8)	−0.0003 (6)	0.0006 (6)	−0.0005 (7)
C8	0.0241 (8)	0.0259 (9)	0.0185 (8)	0.0001 (6)	−0.0007 (6)	−0.0017 (7)
C9	0.0241 (8)	0.0189 (8)	0.0180 (8)	−0.0015 (6)	0.0007 (6)	0.0005 (6)
C10	0.0218 (8)	0.0171 (8)	0.0185 (8)	−0.0016 (6)	0.0005 (6)	0.0023 (6)
C11	0.0246 (8)	0.0199 (8)	0.0160 (8)	−0.0009 (6)	0.0012 (6)	−0.0002 (6)
C12	0.0204 (8)	0.0211 (8)	0.0235 (8)	0.0026 (6)	0.0017 (6)	0.0003 (6)
C13	0.0233 (8)	0.0195 (8)	0.0203 (8)	−0.0006 (6)	−0.0017 (6)	0.0020 (6)
C14	0.0274 (8)	0.0192 (8)	0.0163 (8)	0.0002 (6)	−0.0001 (6)	0.0000 (6)
C15	0.0217 (8)	0.0204 (8)	0.0202 (8)	0.0009 (6)	0.0029 (6)	0.0013 (6)
C16	0.0277 (9)	0.0317 (10)	0.0273 (9)	0.0009 (7)	−0.0041 (7)	−0.0021 (7)

F1—C3	1.3621 (17)	C9—C10	1.456 (2)
O1—C7	1.2315 (18)	C9—H9A	0.9300
C1—C2	1.382 (2)	C10—C11	1.398 (2)
C1—C6	1.398 (2)	C10—C15	1.404 (2)
C1—H1A	0.9300	C11—C12	1.386 (2)
C2—C3	1.375 (2)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.392 (2)
C3—C4	1.377 (2)	C12—H12A	0.9300
C4—C5	1.385 (2)	C13—C14	1.396 (2)
C4—H4A	0.9300	C13—C16	1.502 (2)
C5—C6	1.393 (2)	C14—C15	1.382 (2)
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.492 (2)	C15—H15A	0.9300
C7—C8	1.473 (2)	C16—H16A	0.9600
C8—C9	1.335 (2)	C16—H16B	0.9600
C8—H8A	0.9300	C16—H16C	0.9600
C2—C1—C6	120.43 (15)	C10—C9—H9A	116.3
C2—C1—H1A	119.8	C11—C10—C15	117.72 (14)
C6—C1—H1A	119.8	C11—C10—C9	119.37 (14)
C3—C2—C1	118.31 (14)	C15—C10—C9	122.83 (14)
C3—C2—H2A	120.8	C12—C11—C10	121.27 (14)
C1—C2—H2A	120.8	C12—C11—H11A	119.4
F1—C3—C2	118.24 (14)	C10—C11—H11A	119.4
F1—C3—C4	118.47 (14)	C11—C12—C13	120.90 (14)
C2—C3—C4	123.28 (15)	C11—C12—H12A	119.6
C3—C4—C5	117.83 (15)	C13—C12—H12A	119.6
C3—C4—H4A	121.1	C12—C13—C14	117.96 (15)
C5—C4—H4A	121.1	C12—C13—C16	121.36 (14)
C4—C5—C6	120.87 (14)	C14—C13—C16	120.66 (14)
C4—C5—H5A	119.6	C15—C14—C13	121.50 (15)
C6—C5—H5A	119.6	C15—C14—H14A	119.2
C5—C6—C1	119.26 (14)	C13—C14—H14A	119.2
C5—C6—C7	118.51 (13)	C14—C15—C10	120.61 (14)
C1—C6—C7	122.19 (14)	C14—C15—H15A	119.7
O1—C7—C8	121.73 (14)	C10—C15—H15A	119.7
O1—C7—C6	119.49 (15)	C13—C16—H16A	109.5
C8—C7—C6	118.77 (14)	C13—C16—H16B	109.5
C9—C8—C7	120.80 (15)	H16A—C16—H16B	109.5
C9—C8—H8A	119.6	C13—C16—H16C	109.5
C7—C8—H8A	119.6	H16A—C16—H16C	109.5
C8—C9—C10	127.36 (15)	H16B—C16—H16C	109.5
C8—C9—H9A	116.3
C6—C1—C2—C3	−1.2 (2)	C6—C7—C8—C9	166.14 (15)
C1—C2—C3—F1	−179.03 (13)	C7—C8—C9—C10	174.61 (15)
C1—C2—C3—C4	0.3 (2)	C8—C9—C10—C11	175.44 (15)
F1—C3—C4—C5	−179.85 (13)	C8—C9—C10—C15	−7.9 (3)
C2—C3—C4—C5	0.8 (3)	C15—C10—C11—C12	−1.5 (2)
C3—C4—C5—C6	−1.0 (2)	C9—C10—C11—C12	175.34 (14)
C4—C5—C6—C1	0.2 (2)	C10—C11—C12—C13	−0.1 (2)
C4—C5—C6—C7	178.00 (14)	C11—C12—C13—C14	1.2 (2)
C2—C1—C6—C5	0.9 (2)	C11—C12—C13—C16	−177.22 (15)
C2—C1—C6—C7	−176.76 (15)	C12—C13—C14—C15	−0.8 (2)
C5—C6—C7—O1	−22.4 (2)	C16—C13—C14—C15	177.69 (14)
C1—C6—C7—O1	155.31 (16)	C13—C14—C15—C10	−0.8 (2)
C5—C6—C7—C8	156.49 (15)	C11—C10—C15—C14	1.9 (2)
C1—C6—C7—C8	−25.8 (2)	C9—C10—C15—C14	−174.78 (14)
O1—C7—C8—C9	−15.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.93	2.50	2.820 (2)	100
C5—H5A···Cg1i	0.93	2.96	3.525	120
C9—H9A···Cg1ii	0.93	3.02	3.604	123
C2—H2A···Cg2iii	0.93	3.01	3.635	126
C14—H14A···Cg2iv	0.93	2.76	3.452	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1	0.93	2.50	2.820 (2)	100
C5—H5A⋯Cg1i	0.93	2.96	3.525	120
C9—H9A⋯Cg1ii	0.93	3.02	3.604	123
C2—H2A⋯Cg2iii	0.93	3.01	3.635	126
C14—H14A⋯Cg2iv	0.93	2.76	3.452	132

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the ring C1–C6 and Cg2 is the centroid of the ring C10–C15.