4-[(1E)-3-(2,6-Dichloro-3-fluoro-phen-yl)-3-oxoprop-1-en-1-yl]benzonitrile.

In the title mol-ecule, C(16)H(8)Cl(2)FNO, the benzene rings form a dihedral angle of 78.69 (8)°. The F atom is disordered over two positions in a 0.530 (3):0.470 (3) ratio. The crystal packing exhibits π-π inter-actions between dichloro-substituted rings [centroid-centroid distance = 3.6671 (10) Å] and weak inter-molecular C-H⋯F contacts.

Related literature

For the biological activity of chalcones, see: Rajendra Prasad et al. (2008 ▶); Shivakumar et al. (2005 ▶); Churkin et al. (1982 ▶); Herencia et al. (1998 ▶). For a related structure, see: Betz et al. (2012 ▶). For the graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H8Cl2FNO

M = 320.13

Monoclinic,

a = 13.2751 (3) Å

b = 8.5002 (2) Å

c = 13.9854 (3) Å

β = 116.773 (1)°

V = 1408.95 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.47 mm−1

T = 200 K

0.55 × 0.32 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.783, T max = 0.913

12885 measured reflections

3480 independent reflections

2904 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.05

3480 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.43 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/S1600536812015589/cv5282sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812015589/cv5282Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015589/cv5282Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812015589/cv5282Isup4.cml

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

C16H8Cl2FNO	F(000) = 648
Mr = 320.13	Dx = 1.509 Mg m−3
Monoclinic, P21/c	Melting point = 414–417 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.2751 (3) Å	Cell parameters from 7660 reflections
b = 8.5002 (2) Å	θ = 2.9–28.3°
c = 13.9854 (3) Å	µ = 0.47 mm−1
β = 116.773 (1)°	T = 200 K
V = 1408.95 (6) Å3	Platelet, green
Z = 4	0.55 × 0.32 × 0.20 mm

Bruker APEXII CCD diffractometer	3480 independent reflections
Radiation source: fine-focus sealed tube	2904 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
φ and ω scans	θmax = 28.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −17→17
Tmin = 0.783, Tmax = 0.913	k = −8→11
12885 measured reflections	l = −18→18

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0358P)2 + 0.6287P] where P = (Fo2 + 2Fc2)/3
3480 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.32198 (4)	0.25664 (5)	0.03764 (4)	0.05826 (14)
Cl2	0.43426 (5)	0.87196 (6)	0.08058 (4)	0.06998 (17)
O1	0.23229 (11)	0.62352 (16)	−0.09939 (9)	0.0582 (3)
N1	−0.11644 (13)	0.5937 (3)	0.40221 (14)	0.0785 (6)
C1	0.21695 (12)	0.57997 (17)	0.14653 (12)	0.0392 (3)
H1	0.2927	0.5473	0.1891	0.047*
C2	0.18838 (14)	0.6169 (2)	0.04481 (13)	0.0460 (4)
H2	0.1140	0.6544	0.0017	0.055*
C3	0.26474 (14)	0.60326 (19)	−0.00432 (12)	0.0435 (3)
C4	−0.06074 (13)	0.5902 (2)	0.35969 (14)	0.0525 (4)
C11	0.14352 (12)	0.58457 (17)	0.19935 (11)	0.0370 (3)
C12	0.03215 (13)	0.6397 (2)	0.14813 (13)	0.0487 (4)
H12	0.0022	0.6771	0.0765	0.058*
C13	−0.03410 (13)	0.6403 (2)	0.20037 (13)	0.0489 (4)
H13	−0.1097	0.6771	0.1647	0.059*
C14	0.00933 (12)	0.58722 (18)	0.30543 (12)	0.0408 (3)
C15	0.11978 (12)	0.5340 (2)	0.35809 (12)	0.0440 (3)
H15	0.1498	0.4984	0.4301	0.053*
C16	0.18571 (12)	0.53320 (19)	0.30467 (12)	0.0407 (3)
H16	0.2614	0.4968	0.3407	0.049*
C21	0.38739 (13)	0.56076 (18)	0.06658 (11)	0.0394 (3)
C22	0.42114 (12)	0.40474 (19)	0.08897 (11)	0.0404 (3)
C24	0.61343 (14)	0.4808 (3)	0.19589 (13)	0.0538 (4)
H24	0.6899	0.4539	0.2409	0.065*
C26	0.47029 (15)	0.6754 (2)	0.10883 (13)	0.0467 (4)
C23	0.53293 (14)	0.3657 (2)	0.15222 (13)	0.0474 (4)
H23	0.5542	0.2582	0.1656	0.057*	0.470 (3)
F1B	0.6550 (2)	0.7502 (4)	0.2076 (2)	0.0847 (11)	0.470 (3)
C25	0.58158 (15)	0.6354 (2)	0.17347 (14)	0.0545 (4)
H25	0.6367	0.7160	0.2027	0.065*	0.530 (3)
F1A	0.56085 (16)	0.2148 (3)	0.16948 (16)	0.0610 (7)	0.530 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.0520 (2)	0.0417 (2)	0.0616 (3)	−0.00337 (17)	0.00832 (19)	0.00136 (18)
Cl2	0.1033 (4)	0.0436 (2)	0.0648 (3)	−0.0126 (2)	0.0394 (3)	−0.0003 (2)
O1	0.0635 (7)	0.0718 (9)	0.0403 (6)	0.0168 (6)	0.0242 (6)	0.0145 (6)
N1	0.0455 (8)	0.1321 (18)	0.0629 (10)	0.0129 (10)	0.0288 (8)	−0.0008 (11)
C1	0.0376 (7)	0.0386 (7)	0.0407 (7)	0.0002 (6)	0.0171 (6)	0.0005 (6)
C2	0.0444 (8)	0.0502 (9)	0.0432 (8)	0.0089 (7)	0.0195 (7)	0.0076 (7)
C3	0.0508 (8)	0.0405 (8)	0.0406 (8)	0.0047 (7)	0.0217 (7)	0.0052 (6)
C4	0.0361 (7)	0.0725 (12)	0.0473 (9)	0.0051 (8)	0.0172 (7)	−0.0027 (8)
C11	0.0355 (7)	0.0349 (7)	0.0389 (7)	−0.0007 (6)	0.0153 (6)	−0.0010 (6)
C12	0.0397 (8)	0.0596 (10)	0.0418 (8)	0.0076 (7)	0.0139 (6)	0.0099 (7)
C13	0.0336 (7)	0.0586 (10)	0.0497 (9)	0.0088 (7)	0.0146 (6)	0.0058 (7)
C14	0.0346 (7)	0.0428 (8)	0.0451 (8)	−0.0006 (6)	0.0182 (6)	−0.0052 (6)
C15	0.0392 (7)	0.0525 (9)	0.0404 (7)	0.0054 (6)	0.0179 (6)	0.0025 (7)
C16	0.0332 (7)	0.0465 (8)	0.0401 (7)	0.0059 (6)	0.0147 (6)	0.0024 (6)
C21	0.0461 (8)	0.0440 (8)	0.0327 (7)	0.0000 (6)	0.0219 (6)	0.0015 (6)
C22	0.0405 (7)	0.0443 (8)	0.0348 (7)	−0.0011 (6)	0.0155 (6)	−0.0012 (6)
C24	0.0390 (8)	0.0831 (13)	0.0393 (8)	−0.0030 (8)	0.0176 (7)	−0.0014 (8)
C26	0.0603 (9)	0.0472 (9)	0.0411 (8)	−0.0065 (7)	0.0303 (7)	−0.0005 (7)
C23	0.0464 (8)	0.0571 (10)	0.0389 (7)	0.0080 (7)	0.0193 (7)	0.0015 (7)
F1B	0.0738 (17)	0.107 (2)	0.0622 (16)	−0.0519 (16)	0.0211 (13)	−0.0060 (14)
C25	0.0535 (9)	0.0717 (12)	0.0433 (8)	−0.0211 (9)	0.0260 (8)	−0.0071 (8)
F1A	0.0529 (11)	0.0588 (13)	0.0594 (12)	0.0184 (9)	0.0147 (9)	0.0096 (9)

Cl1—C22	1.7267 (16)	C13—H13	0.9500
Cl2—C26	1.7338 (18)	C14—C15	1.387 (2)
O1—C3	1.2112 (18)	C15—C16	1.383 (2)
N1—C4	1.139 (2)	C15—H15	0.9500
C1—C2	1.334 (2)	C16—H16	0.9500
C1—C11	1.465 (2)	C21—C26	1.387 (2)
C1—H1	0.9500	C21—C22	1.390 (2)
C2—C3	1.463 (2)	C22—C23	1.383 (2)
C2—H2	0.9500	C24—C23	1.373 (3)
C3—C21	1.520 (2)	C24—C25	1.373 (3)
C4—C14	1.441 (2)	C24—H24	0.9500
C11—C16	1.390 (2)	C26—C25	1.383 (3)
C11—C12	1.402 (2)	C23—F1A	1.327 (3)
C12—C13	1.373 (2)	C23—H23	0.9500
C12—H12	0.9500	F1B—C25	1.308 (3)
C13—C14	1.390 (2)	C25—H25	0.9500
C2—C1—C11	126.67 (14)	C15—C16—H16	119.3
C2—C1—H1	116.7	C11—C16—H16	119.3
C11—C1—H1	116.7	C26—C21—C22	117.46 (14)
C1—C2—C3	123.90 (14)	C26—C21—C3	121.47 (15)
C1—C2—H2	118.1	C22—C21—C3	121.05 (14)
C3—C2—H2	118.1	C23—C22—C21	121.15 (15)
O1—C3—C2	121.68 (15)	C23—C22—Cl1	119.24 (13)
O1—C3—C21	119.79 (14)	C21—C22—Cl1	119.61 (11)
C2—C3—C21	118.53 (13)	C23—C24—C25	118.87 (16)
N1—C4—C14	179.4 (2)	C23—C24—H24	120.6
C16—C11—C12	118.39 (14)	C25—C24—H24	120.6
C16—C11—C1	118.96 (13)	C25—C26—C21	120.98 (17)
C12—C11—C1	122.65 (13)	C25—C26—Cl2	119.32 (14)
C13—C12—C11	120.68 (15)	C21—C26—Cl2	119.70 (13)
C13—C12—H12	119.7	F1A—C23—C24	120.69 (17)
C11—C12—H12	119.7	F1A—C23—C22	118.67 (17)
C12—C13—C14	120.06 (14)	C24—C23—C22	120.64 (17)
C12—C13—H13	120.0	F1A—C23—H23	1.0
C14—C13—H13	120.0	C24—C23—H23	119.7
C15—C14—C13	120.21 (14)	C22—C23—H23	119.7
C15—C14—C4	120.30 (14)	F1B—C25—C24	121.9 (2)
C13—C14—C4	119.48 (14)	F1B—C25—C26	117.1 (2)
C16—C15—C14	119.30 (14)	C24—C25—C26	120.87 (16)
C16—C15—H15	120.4	F1B—C25—H25	3.7
C14—C15—H15	120.4	C24—C25—H25	119.6
C15—C16—C11	121.34 (13)	C26—C25—H25	119.6
C11—C1—C2—C3	−177.25 (15)	C26—C21—C22—C23	0.9 (2)
C1—C2—C3—O1	172.76 (17)	C3—C21—C22—C23	179.07 (13)
C1—C2—C3—C21	−6.6 (2)	C26—C21—C22—Cl1	−179.43 (11)
C2—C1—C11—C16	176.31 (16)	C3—C21—C22—Cl1	−1.24 (19)
C2—C1—C11—C12	−4.1 (3)	C22—C21—C26—C25	−2.0 (2)
C16—C11—C12—C13	−1.1 (2)	C3—C21—C26—C25	179.84 (14)
C1—C11—C12—C13	179.29 (16)	C22—C21—C26—Cl2	178.12 (11)
C11—C12—C13—C14	0.6 (3)	C3—C21—C26—Cl2	−0.07 (19)
C12—C13—C14—C15	0.2 (3)	C25—C24—C23—F1A	178.08 (18)
C12—C13—C14—C4	179.32 (17)	C25—C24—C23—C22	−1.7 (2)
N1—C4—C14—C15	136 (21)	C21—C22—C23—F1A	−178.81 (16)
N1—C4—C14—C13	−43 (21)	Cl1—C22—C23—F1A	1.5 (2)
C13—C14—C15—C16	−0.5 (2)	C21—C22—C23—C24	0.9 (2)
C4—C14—C15—C16	−179.57 (16)	Cl1—C22—C23—C24	−178.75 (12)
C14—C15—C16—C11	0.0 (2)	C23—C24—C25—F1B	−176.2 (2)
C12—C11—C16—C15	0.8 (2)	C23—C24—C25—C26	0.6 (2)
C1—C11—C16—C15	−179.54 (14)	C21—C26—C25—F1B	178.18 (19)
O1—C3—C21—C26	84.6 (2)	Cl2—C26—C25—F1B	−1.9 (2)
C2—C3—C21—C26	−96.08 (18)	C21—C26—C25—C24	1.3 (2)
O1—C3—C21—C22	−93.55 (19)	Cl2—C26—C25—C24	−178.81 (13)
C2—C3—C21—C22	85.81 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···F1Ai	0.95	2.50	3.130 (2)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯F1Ai	0.95	2.50	3.130 (2)	124

Symmetry code: (i) .