2-Acetyl-phenyl (2E)-3-(4-fluoro-phen-yl)acrylate.

In the title compound, C(17)H(13)FO(3), the dihedral angle between the benzene rings is 70.34 (5)°. In the crystal, molecules are linked via pairs of bifurcated C-H⋯(O,O) hydrogen bonds, forming inversion dimers. These dimers are linked via C-H⋯O and C-H⋯F inter-actions, forming a three-dimensional structure.

Related literature

For the preparation, see: Pinto et al. (2000 ▶). For related structures, see: Santos et al. (2009 ▶); Ren, Li et al. (2006 ▶); Ren, Zhang et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). The title compound is a core structure in various natural and pharmaceutically active compounds, displaying a broad spectrum of activity, see: Gomes et al. (2010 ▶).

Experimental

Crystal data

C17H13FO3

M = 284.27

Monoclinic,

a = 26.574 (1) Å

b = 6.3883 (3) Å

c = 19.3304 (6) Å

β = 123.037 (2)°

V = 2751.01 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.26 × 0.23 × 0.09 mm

Data collection

Nonius Kappa CCD diffractometer

6005 measured reflections

3150 independent reflections

2201 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 1.05

3150 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT program (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812040536/fj2596sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040536/fj2596Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812040536/fj2596Isup3.cml

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

C17H13FO3	F(000) = 1184
Mr = 284.27	Dx = 1.373 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6005 reflections
a = 26.574 (1) Å	θ = 3.1–27.5°
b = 6.3883 (3) Å	µ = 0.10 mm−1
c = 19.3304 (6) Å	T = 173 K
β = 123.037 (2)°	Plate, colourless
V = 2751.01 (19) Å3	0.26 × 0.23 × 0.09 mm
Z = 8

Nonius Kappa CCD diffractometer	2201 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 27.5°, θmin = 3.1°
1.2° φ scans and ω scans	h = −33→34
6005 measured reflections	k = −8→8
3150 independent reflections	l = −25→24

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0612P)2 + 0.6743P] where P = (Fo2 + 2Fc2)/3
3150 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.20 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	0.04188 (4)	1.49324 (13)	0.22111 (6)	0.0580 (3)
O1	0.26072 (5)	−0.02536 (18)	0.16114 (6)	0.0556 (3)
O2	0.16132 (4)	0.49823 (13)	0.02908 (6)	0.0379 (2)
O3	0.06857 (4)	0.41188 (17)	−0.00442 (7)	0.0522 (3)
C1	0.25590 (7)	0.3344 (3)	0.18081 (9)	0.0512 (4)
H1A	0.2225	0.3695	0.1867	0.077*
H1B	0.2633	0.4515	0.1548	0.077*
H1C	0.2921	0.3074	0.2354	0.077*
C2	0.24038 (6)	0.1439 (2)	0.12848 (8)	0.0377 (3)
C3	0.19990 (5)	0.1519 (2)	0.03588 (7)	0.0315 (3)
C4	0.19941 (6)	−0.0253 (2)	−0.00725 (8)	0.0369 (3)
H4	0.2241	−0.1415	0.0228	0.044*
C5	0.16398 (6)	−0.0351 (2)	−0.09234 (9)	0.0430 (4)
H5	0.1643	−0.1569	−0.1203	0.052*
C6	0.12814 (7)	0.1330 (2)	−0.13652 (8)	0.0447 (4)
H6	0.1039	0.1274	−0.1951	0.054*
C7	0.12732 (6)	0.3091 (2)	−0.09597 (8)	0.0418 (3)
H7	0.1026	0.4247	−0.1265	0.050*
C8	0.16273 (6)	0.3169 (2)	−0.01042 (8)	0.0327 (3)
C9	0.11003 (6)	0.5312 (2)	0.02865 (8)	0.0337 (3)
C10	0.11450 (6)	0.72268 (19)	0.07306 (8)	0.0339 (3)
H10	0.1496	0.8069	0.0972	0.041*
C11	0.06885 (6)	0.7778 (2)	0.07935 (8)	0.0346 (3)
H11	0.0355	0.6853	0.0548	0.042*
C12	0.06392 (6)	0.96377 (19)	0.11951 (7)	0.0321 (3)
C13	0.01102 (6)	0.9974 (2)	0.11673 (8)	0.0379 (3)
H13	−0.0204	0.8971	0.0906	0.045*
C14	0.00350 (6)	1.1745 (2)	0.15135 (8)	0.0418 (3)
H14	−0.0326	1.1971	0.1493	0.050*
C15	0.04946 (6)	1.3164 (2)	0.18860 (8)	0.0388 (3)
C16	0.10298 (6)	1.2888 (2)	0.19487 (8)	0.0385 (3)
H16	0.1344	1.3885	0.2226	0.046*
C17	0.10980 (6)	1.1118 (2)	0.15972 (8)	0.0360 (3)
H17	0.1464	1.0903	0.1629	0.043*

	U11	U22	U33	U12	U13	U23
F1	0.0663 (6)	0.0476 (5)	0.0611 (6)	−0.0033 (4)	0.0354 (5)	−0.0236 (4)
O1	0.0560 (7)	0.0582 (7)	0.0411 (6)	0.0116 (5)	0.0191 (5)	0.0104 (5)
O2	0.0366 (5)	0.0330 (5)	0.0456 (5)	−0.0029 (4)	0.0234 (4)	−0.0093 (4)
O3	0.0453 (6)	0.0485 (6)	0.0693 (7)	−0.0152 (5)	0.0354 (6)	−0.0258 (5)
C1	0.0492 (9)	0.0627 (10)	0.0346 (8)	−0.0076 (7)	0.0183 (7)	−0.0089 (7)
C2	0.0314 (7)	0.0486 (8)	0.0358 (7)	−0.0011 (6)	0.0201 (6)	−0.0001 (6)
C3	0.0303 (6)	0.0351 (7)	0.0331 (7)	−0.0026 (5)	0.0200 (5)	−0.0011 (5)
C4	0.0397 (7)	0.0348 (7)	0.0413 (8)	0.0037 (6)	0.0254 (6)	0.0013 (6)
C5	0.0512 (9)	0.0416 (8)	0.0440 (8)	−0.0030 (7)	0.0311 (7)	−0.0103 (7)
C6	0.0468 (8)	0.0541 (9)	0.0317 (7)	−0.0014 (7)	0.0205 (6)	−0.0045 (7)
C7	0.0437 (8)	0.0426 (8)	0.0361 (7)	0.0060 (6)	0.0199 (6)	0.0037 (6)
C8	0.0346 (7)	0.0305 (7)	0.0366 (7)	−0.0031 (5)	0.0217 (6)	−0.0039 (5)
C9	0.0348 (7)	0.0327 (7)	0.0334 (7)	0.0005 (6)	0.0183 (6)	0.0001 (5)
C10	0.0355 (7)	0.0296 (7)	0.0341 (7)	−0.0025 (5)	0.0174 (6)	−0.0019 (5)
C11	0.0352 (7)	0.0305 (7)	0.0344 (7)	−0.0032 (5)	0.0165 (6)	−0.0030 (5)
C12	0.0352 (7)	0.0295 (7)	0.0283 (6)	0.0002 (5)	0.0151 (5)	−0.0001 (5)
C13	0.0340 (7)	0.0377 (7)	0.0372 (7)	−0.0044 (6)	0.0164 (6)	−0.0086 (6)
C14	0.0366 (7)	0.0463 (8)	0.0408 (8)	0.0010 (6)	0.0199 (6)	−0.0080 (6)
C15	0.0492 (8)	0.0322 (7)	0.0313 (7)	0.0017 (6)	0.0196 (6)	−0.0063 (6)
C16	0.0424 (8)	0.0332 (7)	0.0343 (7)	−0.0080 (6)	0.0172 (6)	−0.0048 (6)
C17	0.0377 (7)	0.0338 (7)	0.0364 (7)	−0.0026 (6)	0.0201 (6)	−0.0015 (6)

F1—C15	1.3600 (15)	C7—C8	1.3878 (18)
O1—C2	1.2195 (17)	C7—H7	0.9500
O2—C9	1.3748 (16)	C9—C10	1.4614 (17)
O2—C8	1.3993 (15)	C10—C11	1.3310 (19)
O3—C9	1.1982 (16)	C10—H10	0.9500
C1—C2	1.490 (2)	C11—C12	1.4636 (17)
C1—H1A	0.9800	C11—H11	0.9500
C1—H1B	0.9800	C12—C13	1.3937 (18)
C1—H1C	0.9800	C12—C17	1.3972 (18)
C2—C3	1.5048 (19)	C13—C14	1.3835 (18)
C3—C8	1.3869 (18)	C13—H13	0.9500
C3—C4	1.4014 (18)	C14—C15	1.369 (2)
C4—C5	1.381 (2)	C14—H14	0.9500
C4—H4	0.9500	C15—C16	1.371 (2)
C5—C6	1.379 (2)	C16—C17	1.3814 (19)
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.378 (2)	C17—H17	0.9500
C6—H6	0.9500
C9—O2—C8	116.42 (9)	O3—C9—O2	121.72 (12)
C2—C1—H1A	109.5	O3—C9—C10	127.06 (12)
C2—C1—H1B	109.5	O2—C9—C10	111.22 (11)
H1A—C1—H1B	109.5	C11—C10—C9	119.26 (12)
C2—C1—H1C	109.5	C11—C10—H10	120.4
H1A—C1—H1C	109.5	C9—C10—H10	120.4
H1B—C1—H1C	109.5	C10—C11—C12	127.80 (12)
O1—C2—C1	119.47 (12)	C10—C11—H11	116.1
O1—C2—C3	118.28 (12)	C12—C11—H11	116.1
C1—C2—C3	122.25 (12)	C13—C12—C17	118.24 (12)
C8—C3—C4	117.21 (11)	C13—C12—C11	119.00 (11)
C8—C3—C2	126.11 (11)	C17—C12—C11	122.76 (12)
C4—C3—C2	116.67 (11)	C14—C13—C12	121.07 (12)
C5—C4—C3	121.63 (13)	C14—C13—H13	119.5
C5—C4—H4	119.2	C12—C13—H13	119.5
C3—C4—H4	119.2	C15—C14—C13	118.25 (13)
C6—C5—C4	119.62 (13)	C15—C14—H14	120.9
C6—C5—H5	120.2	C13—C14—H14	120.9
C4—C5—H5	120.2	F1—C15—C14	118.60 (13)
C7—C6—C5	120.20 (12)	F1—C15—C16	118.28 (12)
C7—C6—H6	119.9	C14—C15—C16	123.12 (12)
C5—C6—H6	119.9	C15—C16—C17	118.02 (12)
C6—C7—C8	119.76 (13)	C15—C16—H16	121.0
C6—C7—H7	120.1	C17—C16—H16	121.0
C8—C7—H7	120.1	C16—C17—C12	121.26 (12)
C3—C8—C7	121.56 (12)	C16—C17—H17	119.4
C3—C8—O2	119.91 (11)	C12—C17—H17	119.4
C7—C8—O2	118.51 (11)
O1—C2—C3—C8	164.97 (13)	C8—O2—C9—O3	−0.64 (18)
C1—C2—C3—C8	−14.7 (2)	C8—O2—C9—C10	178.87 (10)
O1—C2—C3—C4	−14.28 (18)	O3—C9—C10—C11	0.0 (2)
C1—C2—C3—C4	166.04 (12)	O2—C9—C10—C11	−179.43 (12)
C8—C3—C4—C5	0.71 (19)	C9—C10—C11—C12	−178.78 (11)
C2—C3—C4—C5	−179.97 (12)	C10—C11—C12—C13	177.62 (13)
C3—C4—C5—C6	0.1 (2)	C10—C11—C12—C17	−1.4 (2)
C4—C5—C6—C7	−0.5 (2)	C17—C12—C13—C14	1.26 (19)
C5—C6—C7—C8	0.0 (2)	C11—C12—C13—C14	−177.78 (12)
C4—C3—C8—C7	−1.21 (18)	C12—C13—C14—C15	0.0 (2)
C2—C3—C8—C7	179.54 (12)	C13—C14—C15—F1	178.52 (11)
C4—C3—C8—O2	−179.87 (11)	C13—C14—C15—C16	−1.6 (2)
C2—C3—C8—O2	0.88 (19)	F1—C15—C16—C17	−178.23 (11)
C6—C7—C8—C3	0.9 (2)	C14—C15—C16—C17	1.9 (2)
C6—C7—C8—O2	179.56 (12)	C15—C16—C17—C12	−0.56 (19)
C9—O2—C8—C3	−109.06 (13)	C13—C12—C17—C16	−0.95 (19)
C9—O2—C8—C7	72.24 (15)	C11—C12—C17—C16	178.05 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O2	0.98	2.48	2.8245 (18)	100
C7—H7···F1i	0.95	2.52	3.2402 (16)	132
C11—H11···O3	0.95	2.50	2.8415 (16)	101
C11—H11···O3ii	0.95	2.46	3.3369 (16)	154
C13—H13···O3ii	0.95	2.45	3.3191 (16)	153
C16—H16···O1iii	0.95	2.51	3.3590 (17)	149
C6—H6···Cg1iv	0.95	2.99	3.818 (1)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯F1i	0.95	2.52	3.2402 (16)	132
C11—H11⋯O3ii	0.95	2.46	3.3369 (16)	154
C13—H13⋯O3ii	0.95	2.45	3.3191 (16)	153
C16—H16⋯O1iii	0.95	2.51	3.3590 (17)	149
C6—H6⋯Cg1iv	0.95	2.99	3.818 (1)	146

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .