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

In the title chalcone derivative, C(15)H(8)Cl(4)O, the C=C double bond exists in an E configuration and the dihedral angle between the two benzene rings is 48.13 (11)°. In the crystal, mol-ecules are arranged into columns and stacked down the a axis featuring possible weak aromatic π-π stacking inter-actions [centroid-centroid separation = 3.888 (2) Å].

Related literature

For general background to and applications of chalcone derivatives, see: Geiger & Conn (1945 ▶); Misra et al. (1971 ▶); Cole & Julian (1954 ▶); Aries (1972 ▶); Levine et al. (1979 ▶); Vranasi et al. (1996 ▶).

Experimental

Crystal data

C15H8Cl4O

M = 346.01

Triclinic,

a = 3.8879 (2) Å

b = 6.7510 (3) Å

c = 13.7788 (5) Å

α = 97.620 (2)°

β = 96.177 (2)°

γ = 92.017 (2)°

V = 355.93 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.82 mm−1

T = 296 K

0.76 × 0.33 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.574, T max = 0.837

7510 measured reflections

3395 independent reflections

3183 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.082

S = 1.06

3395 reflections

181 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1324 Friedel pairs

Flack parameter: −0.02 (5)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810053213/hb5777sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053213/hb5777Isup2.hkl

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

C15H8Cl4O	Z = 1
Mr = 346.01	F(000) = 174
Triclinic, P1	Dx = 1.614 Mg m−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.8879 (2) Å	Cell parameters from 5499 reflections
b = 6.7510 (3) Å	θ = 3.0–30.0°
c = 13.7788 (5) Å	µ = 0.82 mm−1
α = 97.620 (2)°	T = 296 K
β = 96.177 (2)°	Block, yellow
γ = 92.017 (2)°	0.76 × 0.33 × 0.22 mm
V = 355.93 (3) Å3

Bruker SMART APEXII CCD diffractometer	3395 independent reflections
Radiation source: fine-focus sealed tube	3183 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→5
Tmin = 0.574, Tmax = 0.837	k = −8→9
7510 measured reflections	l = −19→19

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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0435P)2 + 0.0513P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3395 reflections	Δρmax = 0.33 e Å−3
181 parameters	Δρmin = −0.18 e Å−3
3 restraints	Absolute structure: Flack (1983), 1324 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (5)

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	0.18842 (18)	1.21292 (10)	−0.08423 (5)	0.05987 (19)
Cl2	1.09977 (14)	0.85687 (8)	0.46292 (4)	0.04498 (14)
Cl3	0.99789 (19)	0.85943 (10)	0.68403 (5)	0.05664 (17)
Cl4	0.67317 (19)	0.47391 (11)	0.75284 (5)	0.0645 (2)
O1	0.9846 (5)	0.3188 (3)	0.28530 (12)	0.0512 (4)
C1	0.5993 (6)	0.7313 (4)	0.00979 (16)	0.0407 (5)
H1A	0.6920	0.6148	−0.0180	0.049*
C2	0.4793 (7)	0.8687 (4)	−0.05019 (16)	0.0445 (5)
H2A	0.4894	0.8451	−0.1178	0.053*
C3	0.3445 (6)	1.0413 (4)	−0.00805 (17)	0.0399 (5)
C4	0.3247 (6)	1.0802 (4)	0.09119 (18)	0.0428 (5)
H4A	0.2311	1.1973	0.1179	0.051*
C5	0.4465 (6)	0.9424 (3)	0.15142 (15)	0.0386 (5)
H5A	0.4366	0.9685	0.2190	0.046*
C6	0.5836 (5)	0.7650 (3)	0.11160 (14)	0.0336 (4)
C7	0.7206 (6)	0.6183 (3)	0.17296 (15)	0.0369 (4)
H7A	0.8342	0.5133	0.1418	0.044*
C8	0.6995 (6)	0.6198 (3)	0.26870 (15)	0.0372 (4)
H8A	0.5872	0.7226	0.3021	0.045*
C9	0.8480 (6)	0.4641 (3)	0.32376 (14)	0.0348 (4)
C10	0.8101 (5)	0.4806 (3)	0.43238 (14)	0.0319 (4)
C11	0.9116 (5)	0.6485 (3)	0.50096 (15)	0.0309 (4)
C12	0.8730 (6)	0.6515 (3)	0.60100 (16)	0.0357 (4)
C13	0.7287 (6)	0.4796 (4)	0.63117 (16)	0.0384 (5)
C14	0.6308 (6)	0.3128 (3)	0.56447 (18)	0.0432 (5)
H14A	0.5364	0.1997	0.5856	0.052*
C15	0.6713 (6)	0.3117 (3)	0.46607 (16)	0.0384 (4)
H15A	0.6054	0.1972	0.4216	0.046*

	U11	U22	U33	U12	U13	U23
Cl1	0.0665 (4)	0.0563 (4)	0.0629 (4)	0.0105 (3)	0.0037 (3)	0.0313 (3)
Cl2	0.0504 (3)	0.0319 (2)	0.0539 (3)	−0.0034 (2)	0.0081 (2)	0.0100 (2)
Cl3	0.0731 (4)	0.0484 (3)	0.0425 (3)	0.0058 (3)	−0.0047 (3)	−0.0069 (2)
Cl4	0.0849 (5)	0.0797 (5)	0.0369 (3)	0.0232 (4)	0.0178 (3)	0.0231 (3)
O1	0.0688 (12)	0.0460 (9)	0.0405 (8)	0.0188 (9)	0.0118 (8)	0.0036 (7)
C1	0.0496 (13)	0.0391 (11)	0.0343 (10)	0.0064 (10)	0.0069 (9)	0.0059 (8)
C2	0.0545 (13)	0.0489 (12)	0.0309 (9)	0.0041 (11)	0.0054 (9)	0.0072 (9)
C3	0.0393 (11)	0.0390 (11)	0.0440 (11)	0.0012 (9)	0.0028 (9)	0.0170 (9)
C4	0.0469 (12)	0.0331 (10)	0.0504 (12)	0.0074 (9)	0.0096 (10)	0.0078 (9)
C5	0.0468 (12)	0.0374 (11)	0.0314 (9)	0.0025 (9)	0.0056 (9)	0.0027 (8)
C6	0.0355 (9)	0.0342 (9)	0.0323 (9)	0.0014 (8)	0.0054 (8)	0.0074 (7)
C7	0.0376 (10)	0.0379 (11)	0.0367 (10)	0.0050 (9)	0.0061 (8)	0.0085 (8)
C8	0.0388 (11)	0.0399 (11)	0.0348 (10)	0.0067 (9)	0.0057 (8)	0.0095 (8)
C9	0.0379 (10)	0.0357 (10)	0.0317 (9)	0.0035 (8)	0.0044 (8)	0.0073 (7)
C10	0.0347 (10)	0.0293 (9)	0.0334 (9)	0.0074 (8)	0.0047 (8)	0.0086 (7)
C11	0.0307 (9)	0.0281 (9)	0.0348 (9)	0.0051 (7)	0.0024 (7)	0.0079 (7)
C12	0.0372 (10)	0.0364 (10)	0.0332 (9)	0.0105 (8)	−0.0003 (8)	0.0045 (7)
C13	0.0409 (11)	0.0460 (12)	0.0318 (9)	0.0127 (9)	0.0046 (8)	0.0146 (8)
C14	0.0462 (12)	0.0397 (12)	0.0483 (12)	0.0046 (10)	0.0075 (10)	0.0203 (10)
C15	0.0469 (12)	0.0286 (10)	0.0388 (10)	−0.0008 (8)	0.0000 (9)	0.0063 (8)

Cl1—C3	1.745 (2)	C6—C7	1.463 (3)
Cl2—C11	1.730 (2)	C7—C8	1.329 (3)
Cl3—C12	1.709 (2)	C7—H7A	0.9300
Cl4—C13	1.718 (2)	C8—C9	1.474 (3)
O1—C9	1.218 (3)	C8—H8A	0.9300
C1—C2	1.383 (3)	C9—C10	1.509 (3)
C1—C6	1.399 (3)	C10—C11	1.392 (3)
C1—H1A	0.9300	C10—C15	1.399 (3)
C2—C3	1.378 (3)	C11—C12	1.400 (3)
C2—H2A	0.9300	C12—C13	1.403 (3)
C3—C4	1.369 (3)	C13—C14	1.370 (4)
C4—C5	1.389 (3)	C14—C15	1.381 (3)
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.398 (3)	C15—H15A	0.9300
C5—H5A	0.9300
C2—C1—C6	121.0 (2)	C9—C8—H8A	118.8
C2—C1—H1A	119.5	O1—C9—C8	123.42 (18)
C6—C1—H1A	119.5	O1—C9—C10	118.57 (18)
C3—C2—C1	118.9 (2)	C8—C9—C10	117.92 (17)
C3—C2—H2A	120.6	C11—C10—C15	118.23 (18)
C1—C2—H2A	120.6	C11—C10—C9	124.79 (18)
C4—C3—C2	122.0 (2)	C15—C10—C9	116.95 (19)
C4—C3—Cl1	119.28 (18)	C10—C11—C12	121.51 (18)
C2—C3—Cl1	118.73 (17)	C10—C11—Cl2	119.60 (14)
C3—C4—C5	119.1 (2)	C12—C11—Cl2	118.87 (16)
C3—C4—H4A	120.5	C11—C12—C13	118.2 (2)
C5—C4—H4A	120.5	C11—C12—Cl3	120.83 (17)
C4—C5—C6	120.77 (19)	C13—C12—Cl3	120.94 (16)
C4—C5—H5A	119.6	C14—C13—C12	120.76 (19)
C6—C5—H5A	119.6	C14—C13—Cl4	118.73 (17)
C5—C6—C1	118.25 (19)	C12—C13—Cl4	120.51 (18)
C5—C6—C7	122.28 (18)	C13—C14—C15	120.4 (2)
C1—C6—C7	119.43 (18)	C13—C14—H14A	119.8
C8—C7—C6	126.72 (19)	C15—C14—H14A	119.8
C8—C7—H7A	116.6	C14—C15—C10	120.9 (2)
C6—C7—H7A	116.6	C14—C15—H15A	119.6
C7—C8—C9	122.32 (19)	C10—C15—H15A	119.6
C7—C8—H8A	118.8
C6—C1—C2—C3	0.4 (4)	C8—C9—C10—C15	127.9 (2)
C1—C2—C3—C4	−0.3 (4)	C15—C10—C11—C12	−0.9 (3)
C1—C2—C3—Cl1	−179.2 (2)	C9—C10—C11—C12	−178.96 (19)
C2—C3—C4—C5	0.5 (4)	C15—C10—C11—Cl2	177.53 (17)
Cl1—C3—C4—C5	179.44 (19)	C9—C10—C11—Cl2	−0.6 (3)
C3—C4—C5—C6	−0.8 (4)	C10—C11—C12—C13	0.1 (3)
C4—C5—C6—C1	0.9 (3)	Cl2—C11—C12—C13	−178.29 (16)
C4—C5—C6—C7	178.7 (2)	C10—C11—C12—Cl3	−179.78 (17)
C2—C1—C6—C5	−0.7 (3)	Cl2—C11—C12—Cl3	1.8 (2)
C2—C1—C6—C7	−178.6 (2)	C11—C12—C13—C14	0.5 (3)
C5—C6—C7—C8	8.2 (4)	Cl3—C12—C13—C14	−179.62 (19)
C1—C6—C7—C8	−174.0 (2)	C11—C12—C13—Cl4	−179.80 (16)
C6—C7—C8—C9	−179.9 (2)	Cl3—C12—C13—Cl4	0.1 (3)
C7—C8—C9—O1	−3.7 (4)	C12—C13—C14—C15	−0.3 (3)
C7—C8—C9—C10	179.8 (2)	Cl4—C13—C14—C15	179.98 (19)
O1—C9—C10—C11	129.4 (2)	C13—C14—C15—C10	−0.5 (4)
C8—C9—C10—C11	−53.9 (3)	C11—C10—C15—C14	1.1 (3)
O1—C9—C10—C15	−48.7 (3)	C9—C10—C15—C14	179.3 (2)