(E)-3-(4-Chloro-phen-yl)-1-(2,4-dichloro-5-fluoro-phen-yl)prop-2-en-1-one.

In the title chalcone derivative, C(15)H(8)Cl(3)FO, the dihedral angle between the two benzene rings is 43.35 (8)°. Weak C-H⋯O and C-H⋯Cl intra-molecular inter-actions involving the enone group generate S(5) and S(6) ring motifs, respectively. In the crystal structure, mol-ecules are linked into anti-parallel chains along the a axis. These chains are stacked along the b axis and short Cl⋯F contacts of 3.100 (1) Å link adjacent mol-ecules of the anti-parallel chains into dimers.

Related literature

For hydrogen bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see, for example: Fun et al. (2007 ▶); Patil et al. (2007a ▶,b). For background to the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999 ▶); Patil et al. (2006 ▶); Shivarama Holla et al. (2004 ▶). For related literature, see: Gu et al. (2008 ▶).

Experimental

Crystal data

C15H8Cl3FO

M = 329.56

Monoclinic,

a = 6.8271 (1) Å

b = 3.7832 (1) Å

c = 52.0206 (10) Å

β = 96.100 (1)°

V = 1336.00 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.69 mm−1

T = 100.0 (1) K

0.35 × 0.29 × 0.18 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.794, T max = 0.889

42462 measured reflections

5852 independent reflections

5257 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.113

S = 1.28

5852 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.31 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; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012178/sj2488sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012178/sj2488Isup2.hkl

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

C15H8Cl3FO	F000 = 664
Mr = 329.56	Dx = 1.638 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5852 reflections
a = 6.8271 (1) Å	θ = 0.8–35.0º
b = 3.7832 (1) Å	µ = 0.69 mm−1
c = 52.0206 (10) Å	T = 100.0 (1) K
β = 96.100 (1)º	Block, colorless
V = 1336.00 (5) Å3	0.35 × 0.29 × 0.18 mm
Z = 4

Bruker SMART APEX2 CCD area-detector diffractometer	5852 independent reflections
Radiation source: fine-focus sealed tube	5257 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.036
Detector resolution: 8.33 pixels mm-1	θmax = 35.0º
T = 100.0(1) K	θmin = 0.8º
ω scans	h = −11→11
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −6→6
Tmin = 0.794, Tmax = 0.889	l = −83→72
42462 measured reflections

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)] = 0.051	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0246P)2 + 1.777P] where P = (Fo2 + 2Fc2)/3
S = 1.29	(Δ/σ)max = 0.001
5852 reflections	Δρmax = 0.47 e Å−3
181 parameters	Δρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature 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
Cl1	0.75834 (7)	0.29526 (14)	0.494133 (8)	0.02272 (10)
Cl2	0.27758 (6)	−0.21297 (12)	0.414214 (9)	0.01926 (9)
Cl3	−0.33602 (6)	0.43796 (13)	0.273464 (9)	0.02136 (9)
F1	1.03386 (16)	0.3790 (4)	0.45548 (2)	0.0240 (2)
O1	0.75361 (19)	−0.1864 (4)	0.37069 (3)	0.0211 (3)
C1	0.8267 (2)	0.1756 (5)	0.41951 (3)	0.0159 (3)
H1	0.9260	0.2170	0.4090	0.019*
C2	0.8591 (2)	0.2477 (5)	0.44562 (3)	0.0164 (3)
C3	0.7139 (3)	0.1882 (5)	0.46193 (3)	0.0163 (3)
C4	0.5343 (2)	0.0489 (5)	0.45181 (3)	0.0169 (3)
H4	0.4363	0.0044	0.4625	0.020*
C5	0.5022 (2)	−0.0237 (4)	0.42545 (3)	0.0147 (3)
C6	0.6458 (2)	0.0408 (4)	0.40887 (3)	0.0144 (3)
C7	0.6216 (2)	−0.0317 (5)	0.38025 (3)	0.0153 (3)
C8	0.4414 (2)	0.0999 (5)	0.36537 (3)	0.0163 (3)
H8	0.3552	0.2390	0.3737	0.020*
C9	0.3966 (2)	0.0265 (5)	0.34022 (3)	0.0160 (3)
H9	0.4878	−0.1048	0.3322	0.019*
C10	0.2173 (2)	0.1348 (4)	0.32437 (3)	0.0142 (3)
C11	0.1999 (2)	0.0697 (5)	0.29770 (3)	0.0160 (3)
H11	0.3036	−0.0370	0.2904	0.019*
C12	0.0306 (3)	0.1616 (5)	0.28197 (3)	0.0163 (3)
H12	0.0205	0.1187	0.2643	0.020*
C13	−0.1239 (2)	0.3191 (5)	0.29314 (3)	0.0161 (3)
C14	−0.1123 (2)	0.3856 (5)	0.31941 (3)	0.0166 (3)
H14	−0.2171	0.4903	0.3266	0.020*
C15	0.0583 (2)	0.2938 (5)	0.33493 (3)	0.0167 (3)
H15	0.0672	0.3383	0.3526	0.020*

	U11	U22	U33	U12	U13	U23
Cl1	0.0267 (2)	0.0276 (2)	0.01395 (17)	−0.00233 (17)	0.00251 (14)	−0.00137 (16)
Cl2	0.01366 (16)	0.02036 (19)	0.02387 (19)	−0.00204 (14)	0.00256 (13)	−0.00089 (15)
Cl3	0.01787 (17)	0.0229 (2)	0.0221 (2)	0.00123 (15)	−0.00347 (14)	0.00159 (16)
F1	0.0177 (5)	0.0353 (7)	0.0186 (5)	−0.0072 (5)	0.0003 (4)	−0.0023 (5)
O1	0.0187 (6)	0.0267 (7)	0.0183 (6)	0.0044 (5)	0.0036 (4)	−0.0029 (5)
C1	0.0135 (6)	0.0179 (7)	0.0163 (7)	0.0005 (5)	0.0023 (5)	0.0005 (6)
C2	0.0139 (6)	0.0184 (7)	0.0167 (7)	−0.0008 (5)	0.0008 (5)	0.0006 (6)
C3	0.0187 (7)	0.0173 (7)	0.0132 (6)	0.0012 (6)	0.0027 (5)	0.0010 (6)
C4	0.0160 (7)	0.0190 (7)	0.0163 (7)	0.0008 (6)	0.0046 (5)	0.0022 (6)
C5	0.0123 (6)	0.0139 (7)	0.0178 (7)	0.0008 (5)	0.0015 (5)	0.0007 (5)
C6	0.0139 (6)	0.0142 (7)	0.0149 (7)	0.0022 (5)	0.0013 (5)	0.0012 (5)
C7	0.0160 (6)	0.0151 (7)	0.0148 (7)	0.0002 (5)	0.0015 (5)	−0.0004 (5)
C8	0.0160 (7)	0.0159 (7)	0.0167 (7)	0.0022 (6)	0.0006 (5)	−0.0008 (6)
C9	0.0156 (6)	0.0156 (7)	0.0166 (7)	−0.0001 (5)	0.0014 (5)	0.0001 (6)
C10	0.0152 (6)	0.0126 (6)	0.0148 (6)	−0.0005 (5)	0.0017 (5)	−0.0001 (5)
C11	0.0177 (7)	0.0158 (7)	0.0148 (7)	0.0004 (6)	0.0036 (5)	−0.0008 (6)
C12	0.0201 (7)	0.0145 (7)	0.0141 (7)	0.0005 (6)	0.0010 (5)	0.0001 (5)
C13	0.0156 (6)	0.0154 (7)	0.0166 (7)	−0.0013 (6)	−0.0009 (5)	0.0016 (6)
C14	0.0157 (6)	0.0168 (7)	0.0175 (7)	0.0017 (6)	0.0028 (5)	−0.0003 (6)
C15	0.0169 (7)	0.0190 (7)	0.0143 (6)	0.0007 (6)	0.0023 (5)	−0.0006 (6)

Cl1—C3	1.7190 (17)	C8—C9	1.341 (2)
Cl2—C5	1.7366 (17)	C8—H8	0.9300
Cl3—C13	1.7412 (17)	C9—C10	1.460 (2)
F1—C2	1.343 (2)	C9—H9	0.9300
O1—C7	1.224 (2)	C10—C11	1.402 (2)
C1—C2	1.380 (2)	C10—C15	1.403 (2)
C1—C6	1.395 (2)	C11—C12	1.388 (2)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.390 (2)	C12—C13	1.391 (2)
C3—C4	1.386 (2)	C12—H12	0.9300
C4—C5	1.392 (2)	C13—C14	1.383 (2)
C4—H4	0.9300	C14—C15	1.389 (2)
C5—C6	1.394 (2)	C14—H14	0.9300
C6—C7	1.505 (2)	C15—H15	0.9300
C7—C8	1.469 (2)
C2—C1—C6	120.37 (15)	C7—C8—H8	118.8
C2—C1—H1	119.8	C8—C9—C10	125.68 (16)
C6—C1—H1	119.8	C8—C9—H9	117.2
F1—C2—C1	119.49 (15)	C10—C9—H9	117.2
F1—C2—C3	119.28 (15)	C11—C10—C15	118.36 (15)
C1—C2—C3	121.23 (16)	C11—C10—C9	119.16 (15)
C4—C3—C2	119.29 (15)	C15—C10—C9	122.45 (15)
C4—C3—Cl1	121.14 (13)	C12—C11—C10	121.15 (16)
C2—C3—Cl1	119.55 (13)	C12—C11—H11	119.4
C3—C4—C5	119.29 (15)	C10—C11—H11	119.4
C3—C4—H4	120.4	C11—C12—C13	118.82 (15)
C5—C4—H4	120.4	C11—C12—H12	120.6
C4—C5—C6	121.82 (15)	C13—C12—H12	120.6
C4—C5—Cl2	116.97 (13)	C14—C13—C12	121.60 (15)
C6—C5—Cl2	121.17 (13)	C14—C13—Cl3	119.38 (13)
C5—C6—C1	117.98 (15)	C12—C13—Cl3	119.02 (13)
C5—C6—C7	124.71 (15)	C13—C14—C15	119.06 (16)
C1—C6—C7	117.29 (15)	C13—C14—H14	120.5
O1—C7—C8	124.03 (16)	C15—C14—H14	120.5
O1—C7—C6	118.75 (15)	C14—C15—C10	121.01 (16)
C8—C7—C6	117.19 (14)	C14—C15—H15	119.5
C9—C8—C7	122.36 (16)	C10—C15—H15	119.5
C9—C8—H8	118.8
C6—C1—C2—F1	−179.66 (16)	C5—C6—C7—C8	49.0 (2)
C6—C1—C2—C3	0.1 (3)	C1—C6—C7—C8	−132.33 (17)
F1—C2—C3—C4	−179.28 (16)	O1—C7—C8—C9	7.5 (3)
C1—C2—C3—C4	0.9 (3)	C6—C7—C8—C9	−174.50 (16)
F1—C2—C3—Cl1	1.8 (2)	C7—C8—C9—C10	177.37 (16)
C1—C2—C3—Cl1	−177.94 (14)	C8—C9—C10—C11	173.51 (18)
C2—C3—C4—C5	−0.9 (3)	C8—C9—C10—C15	−8.3 (3)
Cl1—C3—C4—C5	177.97 (14)	C15—C10—C11—C12	0.4 (3)
C3—C4—C5—C6	−0.2 (3)	C9—C10—C11—C12	178.70 (16)
C3—C4—C5—Cl2	177.69 (14)	C10—C11—C12—C13	−0.4 (3)
C4—C5—C6—C1	1.2 (3)	C11—C12—C13—C14	0.0 (3)
Cl2—C5—C6—C1	−176.57 (13)	C11—C12—C13—Cl3	179.54 (14)
C4—C5—C6—C7	179.86 (16)	C12—C13—C14—C15	0.2 (3)
Cl2—C5—C6—C7	2.1 (2)	Cl3—C13—C14—C15	−179.27 (14)
C2—C1—C6—C5	−1.2 (3)	C13—C14—C15—C10	−0.2 (3)
C2—C1—C6—C7	−179.91 (16)	C11—C10—C15—C14	−0.2 (3)
C5—C6—C7—O1	−132.87 (19)	C9—C10—C15—C14	−178.37 (17)
C1—C6—C7—O1	45.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cl2	0.93	2.81	3.1164 (16)	101
C9—H9···O1	0.93	2.57	2.878 (2)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cl2	0.93	2.81	3.1164 (16)	101
C9—H9⋯O1	0.93	2.57	2.878 (2)	100