(2E)-1-(2,6-Dichloro-3-fluoro-phen-yl)-3-phenyl-prop-2-en-1-one.

In the title compound, C(15)H(9)Cl(2)FO, the F atom shows positional disorder over two positions, with site-occupancy factors of 0.747 (4) and 0.253 (4). The dihedral angle between the rings is 86.37 (10)°. In the crystal, C-H⋯O contacts connect the mol-ecules into chains along the c axis. The shortest inter-centroid distance between two aromatic systems is 3.6686 (12) Å and is apparent between the halogenated rings.

Related literature

For pharmaceutical background to chalcones, see: Lin et al. (2002 ▶); Modzelewska et al. (2006 ▶); Svetaz et al. (2004 ▶). For related structures, see: Betz et al. (2012 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H9Cl2FO

M = 295.12

Monoclinic,

a = 11.3390 (3) Å

b = 10.3896 (3) Å

c = 11.3930 (3) Å

β = 97.078 (1)°

V = 1331.95 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 200 K

0.49 × 0.34 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.798, T max = 0.920

23002 measured reflections

3329 independent reflections

2742 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.04

3329 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.60 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010574/hg5184sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812010574/hg5184Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010574/hg5184Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812010574/hg5184Isup4.cml

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

C15H9Cl2FO	F(000) = 600
Mr = 295.12	Dx = 1.472 Mg m−3
Monoclinic, P21/c	Melting point = 385–388 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.3390 (3) Å	Cell parameters from 9971 reflections
b = 10.3896 (3) Å	θ = 2.7–28.3°
c = 11.3930 (3) Å	µ = 0.49 mm−1
β = 97.078 (1)°	T = 200 K
V = 1331.95 (6) Å3	Block, colourless
Z = 4	0.49 × 0.34 × 0.17 mm

Bruker APEXII CCD diffractometer	3329 independent reflections
Radiation source: fine-focus sealed tube	2742 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 28.4°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
Tmin = 0.798, Tmax = 0.920	k = −13→13
23002 measured reflections	l = −15→15

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.040P)2 + 0.7737P] where P = (Fo2 + 2Fc2)/3
3329 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.60 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.83699 (6)	0.03537 (6)	0.06241 (5)	0.06914 (19)
Cl2	0.43775 (5)	0.32132 (6)	−0.01452 (5)	0.07146 (19)
O1	0.67486 (13)	0.20446 (13)	−0.16536 (10)	0.0526 (3)
C1	0.76748 (14)	0.40662 (15)	0.08071 (14)	0.0373 (3)
H1	0.7325	0.3570	0.1374	0.045*
C2	0.75116 (16)	0.36328 (16)	−0.03056 (14)	0.0410 (4)
H2	0.7832	0.4114	−0.0901	0.049*
C3	0.68640 (16)	0.24564 (16)	−0.06433 (13)	0.0399 (3)
C11	0.83272 (14)	0.52106 (15)	0.12542 (14)	0.0373 (3)
C12	0.89663 (17)	0.59959 (17)	0.05617 (17)	0.0486 (4)
H12	0.8986	0.5798	−0.0250	0.058*
C13	0.95691 (18)	0.70569 (19)	0.1055 (2)	0.0569 (5)
H13	1.0018	0.7574	0.0584	0.068*
C14	0.9526 (2)	0.7373 (2)	0.2222 (2)	0.0622 (6)
H14	0.9937	0.8112	0.2552	0.075*
C15	0.8889 (2)	0.6619 (2)	0.29125 (19)	0.0602 (5)
H15	0.8850	0.6843	0.3715	0.072*
C16	0.83055 (16)	0.55359 (17)	0.24359 (15)	0.0448 (4)
H16	0.7884	0.5007	0.2922	0.054*
C21	0.63217 (16)	0.17125 (15)	0.03024 (13)	0.0407 (4)
C22	0.69437 (18)	0.07128 (16)	0.09046 (15)	0.0467 (4)
C24	0.5310 (2)	0.0283 (2)	0.20019 (19)	0.0693 (7)
H24	0.4966	−0.0210	0.2574	0.083*
C26	0.51877 (18)	0.19772 (19)	0.05775 (16)	0.0492 (4)
C23A	0.6426 (2)	0.00145 (19)	0.17485 (17)	0.0618 (6)	0.747 (4)
C25A	0.4689 (2)	0.1274 (3)	0.14214 (19)	0.0665 (7)	0.747 (4)
H25A	0.3913	0.1478	0.1599	0.080*	0.747 (4)
F1A	0.7017 (2)	−0.09064 (16)	0.23597 (15)	0.0758 (7)	0.747 (4)
C23B	0.6426 (2)	0.00145 (19)	0.17485 (17)	0.0618 (6)	0.25
H23B	0.6862	−0.0665	0.2157	0.074*	0.253 (4)
C25B	0.4689 (2)	0.1274 (3)	0.14214 (19)	0.0665 (7)	0.25
F2B	0.3774 (5)	0.1417 (8)	0.1629 (6)	0.099 (3)	0.253 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0789 (4)	0.0587 (3)	0.0676 (3)	0.0216 (3)	−0.0001 (3)	0.0108 (2)
Cl2	0.0627 (3)	0.0829 (4)	0.0700 (4)	0.0201 (3)	0.0129 (3)	0.0075 (3)
O1	0.0774 (9)	0.0498 (7)	0.0311 (6)	0.0050 (6)	0.0081 (6)	−0.0060 (5)
C1	0.0450 (8)	0.0320 (7)	0.0358 (7)	0.0024 (6)	0.0077 (6)	0.0041 (6)
C2	0.0523 (9)	0.0386 (8)	0.0327 (7)	0.0025 (7)	0.0077 (6)	0.0057 (6)
C3	0.0512 (9)	0.0373 (8)	0.0311 (7)	0.0084 (7)	0.0051 (6)	0.0000 (6)
C11	0.0393 (8)	0.0319 (7)	0.0403 (8)	0.0043 (6)	0.0031 (6)	0.0045 (6)
C12	0.0544 (10)	0.0406 (9)	0.0516 (10)	0.0008 (8)	0.0098 (8)	0.0096 (7)
C13	0.0501 (10)	0.0430 (9)	0.0763 (14)	−0.0047 (8)	0.0025 (9)	0.0187 (9)
C14	0.0637 (12)	0.0423 (10)	0.0743 (14)	−0.0108 (9)	−0.0161 (10)	0.0041 (9)
C15	0.0760 (14)	0.0490 (11)	0.0522 (11)	−0.0091 (10)	−0.0054 (10)	−0.0057 (9)
C16	0.0537 (10)	0.0392 (8)	0.0409 (8)	−0.0021 (7)	0.0027 (7)	0.0004 (7)
C21	0.0568 (10)	0.0352 (8)	0.0291 (7)	−0.0053 (7)	0.0009 (6)	−0.0041 (6)
C22	0.0665 (11)	0.0360 (8)	0.0354 (8)	−0.0068 (8)	−0.0030 (7)	−0.0018 (6)
C24	0.0934 (17)	0.0662 (14)	0.0480 (11)	−0.0410 (13)	0.0068 (11)	0.0041 (10)
C26	0.0567 (10)	0.0520 (10)	0.0385 (8)	−0.0074 (8)	0.0036 (7)	−0.0054 (7)
C23A	0.0988 (18)	0.0423 (10)	0.0404 (10)	−0.0211 (10)	−0.0078 (10)	0.0058 (8)
C25A	0.0706 (15)	0.0780 (15)	0.0518 (11)	−0.0294 (12)	0.0114 (10)	−0.0063 (11)
F1A	0.1208 (17)	0.0477 (9)	0.0571 (10)	0.0024 (9)	0.0037 (10)	0.0182 (7)
C23B	0.0988 (18)	0.0423 (10)	0.0404 (10)	−0.0211 (10)	−0.0078 (10)	0.0058 (8)
C25B	0.0706 (15)	0.0780 (15)	0.0518 (11)	−0.0294 (12)	0.0114 (10)	−0.0063 (11)
F2B	0.066 (4)	0.136 (6)	0.103 (5)	−0.033 (4)	0.045 (3)	−0.012 (4)

Cl1—C22	1.727 (2)	C14—C15	1.376 (3)
Cl2—C26	1.728 (2)	C14—H14	0.9500
O1—C3	1.2198 (19)	C15—C16	1.382 (3)
C1—C2	1.337 (2)	C15—H15	0.9500
C1—C11	1.459 (2)	C16—H16	0.9500
C1—H1	0.9500	C21—C26	1.388 (3)
C2—C3	1.453 (2)	C21—C22	1.388 (2)
C2—H2	0.9500	C22—C23A	1.391 (3)
C3—C21	1.516 (2)	C24—C23A	1.362 (4)
C11—C16	1.391 (2)	C24—C25A	1.370 (4)
C11—C12	1.398 (2)	C24—H24	0.9500
C12—C13	1.380 (3)	C26—C25A	1.383 (3)
C12—H12	0.9500	C23A—F1A	1.317 (3)
C13—C14	1.377 (3)	C25A—H25A	0.9500
C13—H13	0.9500
C2—C1—C11	127.65 (15)	C16—C15—H15	120.0
C2—C1—H1	116.2	C15—C16—C11	120.87 (18)
C11—C1—H1	116.2	C15—C16—H16	119.6
C1—C2—C3	122.74 (15)	C11—C16—H16	119.6
C1—C2—H2	118.6	C26—C21—C22	117.70 (16)
C3—C2—H2	118.6	C26—C21—C3	121.83 (15)
O1—C3—C2	122.47 (16)	C22—C21—C3	120.45 (16)
O1—C3—C21	119.07 (15)	C21—C22—C23A	120.0 (2)
C2—C3—C21	118.46 (13)	C21—C22—Cl1	120.01 (14)
C16—C11—C12	118.46 (16)	C23A—C22—Cl1	119.97 (16)
C16—C11—C1	117.86 (15)	C23A—C24—C25A	119.2 (2)
C12—C11—C1	123.68 (15)	C23A—C24—H24	120.4
C13—C12—C11	120.13 (18)	C25A—C24—H24	120.4
C13—C12—H12	119.9	C25A—C26—C21	121.5 (2)
C11—C12—H12	119.9	C25A—C26—Cl2	119.02 (18)
C14—C13—C12	120.62 (19)	C21—C26—Cl2	119.52 (14)
C14—C13—H13	119.7	F1A—C23A—C24	117.6 (2)
C12—C13—H13	119.7	F1A—C23A—C22	120.9 (2)
C15—C14—C13	119.97 (19)	C24—C23A—C22	121.5 (2)
C15—C14—H14	120.0	C24—C25A—C26	120.2 (2)
C13—C14—H14	120.0	C24—C25A—H25A	119.9
C14—C15—C16	119.9 (2)	C26—C25A—H25A	119.9
C14—C15—H15	120.0
C11—C1—C2—C3	178.53 (15)	C26—C21—C22—C23A	0.1 (2)
C1—C2—C3—O1	−177.72 (17)	C3—C21—C22—C23A	−178.32 (15)
C1—C2—C3—C21	1.8 (2)	C26—C21—C22—Cl1	−178.77 (13)
C2—C1—C11—C16	175.07 (17)	C3—C21—C22—Cl1	2.8 (2)
C2—C1—C11—C12	−4.7 (3)	C22—C21—C26—C25A	0.0 (3)
C16—C11—C12—C13	0.8 (3)	C3—C21—C26—C25A	178.42 (17)
C1—C11—C12—C13	−179.44 (16)	C22—C21—C26—Cl2	179.90 (12)
C11—C12—C13—C14	−1.6 (3)	C3—C21—C26—Cl2	−1.7 (2)
C12—C13—C14—C15	0.8 (3)	C25A—C24—C23A—F1A	177.08 (19)
C13—C14—C15—C16	0.8 (3)	C25A—C24—C23A—C22	−0.8 (3)
C14—C15—C16—C11	−1.6 (3)	C21—C22—C23A—F1A	−177.52 (17)
C12—C11—C16—C15	0.8 (3)	Cl1—C22—C23A—F1A	1.4 (3)
C1—C11—C16—C15	−178.99 (17)	C21—C22—C23A—C24	0.3 (3)
O1—C3—C21—C26	−92.4 (2)	Cl1—C22—C23A—C24	179.16 (16)
C2—C3—C21—C26	88.0 (2)	C23A—C24—C25A—C26	0.9 (3)
O1—C3—C21—C22	85.9 (2)	C21—C26—C25A—C24	−0.5 (3)
C2—C3—C21—C22	−93.60 (19)	Cl2—C26—C25A—C24	179.59 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1i	0.95	2.50	3.399 (2)	158
C16—H16···O1i	0.95	2.57	3.440 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1i	0.95	2.50	3.399 (2)	158
C16—H16⋯O1i	0.95	2.57	3.440 (2)	153

Symmetry code: (i) .