(2E)-1-(3,4-Dichloro-phen-yl)-3-(2-hy-droxy-phen-yl)prop-2-en-1-one.

In the title compound, C(15)H(10)Cl(2)O(2), the dihedral angle between the mean planes of the two benzene rings is 7.7 (6)°. The crystal packing is influenced by O-H⋯O hydrogen bonds, which form chains along [010]. Weak π-π stacking inter-actions [centroid-centroid distance = 3.6697 (13) Å] are observed, which may contribute to the crystal packing stability.

Related literature

For the pharmacological activity of chalcones, see: Bandgar et al. (2010 ▶); Cheng et al. (2008 ▶); Dhar (1981 ▶); Dimmock et al. (1999 ▶); Nowakowska (2007 ▶). For the synthesis of chalcone derivatives, see: Samshuddin et al. (2010 ▶; 2011 ▶); Fun et al. (2010 ▶); Jasinski et al. (2010 ▶); Baktır et al. (2011 ▶). For related structures, see: Fun et al. (2011 ▶); Jasinski et al. (2011 ▶).

Experimental

Crystal data

C15H10Cl2O2

M = 293.13

Triclinic,

a = 7.2551 (6) Å

b = 7.8351 (7) Å

c = 12.8049 (11) Å

α = 92.367 (7)°

β = 102.946 (8)°

γ = 109.011 (8)°

V = 665.51 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.48 mm−1

T = 173 K

0.34 × 0.15 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.854, T max = 0.972

5430 measured reflections

3174 independent reflections

2417 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 1.01

3174 reflections

175 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000505/vm2148sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000505/vm2148Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000505/vm2148Isup3.cml

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

C15H10Cl2O2	Z = 2
Mr = 293.13	F(000) = 300
Triclinic, P1	Dx = 1.463 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2551 (6) Å	Cell parameters from 1666 reflections
b = 7.8351 (7) Å	θ = 3.1–30.0°
c = 12.8049 (11) Å	µ = 0.48 mm−1
α = 92.367 (7)°	T = 173 K
β = 102.946 (8)°	Plate, pale yellow
γ = 109.011 (8)°	0.34 × 0.15 × 0.06 mm
V = 665.51 (10) Å3

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3174 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2417 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 16.1500 pixels mm-1	θmax = 27.9°, θmin = 3.3°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −9→10
Tmin = 0.854, Tmax = 0.972	l = −16→16
5430 measured reflections

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 atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0532P)2 + 0.1793P] where P = (Fo2 + 2Fc2)/3
3174 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.30 e Å−3
1 restraint	Δρmin = −0.26 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
Cl1	0.23632 (10)	1.23387 (8)	0.22164 (5)	0.0692 (2)
Cl2	0.34479 (10)	0.94069 (9)	0.09406 (4)	0.0681 (2)
O1	0.2056 (2)	0.98170 (17)	0.58884 (10)	0.0528 (4)
O2	0.2367 (2)	0.33480 (17)	0.62755 (10)	0.0467 (3)
H2O	0.232 (3)	0.227 (2)	0.6153 (17)	0.056*
C1	0.2381 (3)	1.0221 (2)	0.38083 (14)	0.0390 (4)
H1A	0.2107	1.1106	0.4190	0.047*
C2	0.2633 (3)	1.0443 (2)	0.27863 (15)	0.0419 (4)
C3	0.3060 (3)	0.9139 (3)	0.22129 (14)	0.0432 (4)
C4	0.3205 (3)	0.7606 (3)	0.26707 (15)	0.0459 (4)
H4A	0.3489	0.6729	0.2288	0.055*
C5	0.2930 (3)	0.7374 (2)	0.36929 (14)	0.0410 (4)
H5A	0.3012	0.6332	0.3992	0.049*
C6	0.2531 (3)	0.8688 (2)	0.42820 (13)	0.0344 (3)
C7	0.2250 (3)	0.8537 (2)	0.53956 (14)	0.0363 (4)
C8	0.2227 (3)	0.6882 (2)	0.58971 (13)	0.0374 (4)
H8A	0.2293	0.5889	0.5503	0.045*
C9	0.2112 (3)	0.6809 (2)	0.69169 (14)	0.0386 (4)
H9A	0.1997	0.7842	0.7240	0.046*
C10	0.2133 (3)	0.5400 (2)	0.76114 (13)	0.0368 (4)
C11	0.2267 (3)	0.3713 (2)	0.73036 (13)	0.0360 (4)
C12	0.2295 (3)	0.2466 (3)	0.80426 (15)	0.0465 (4)
H12A	0.2381	0.1349	0.7833	0.056*
C13	0.2196 (4)	0.2864 (3)	0.90771 (16)	0.0578 (5)
H13A	0.2220	0.2019	0.9565	0.069*
C14	0.2061 (4)	0.4516 (3)	0.93985 (16)	0.0593 (6)
H14A	0.1996	0.4787	1.0100	0.071*
C15	0.2024 (3)	0.5748 (3)	0.86740 (15)	0.0506 (5)
H15A	0.1923	0.6853	0.8894	0.061*

	U11	U22	U33	U12	U13	U23
Cl1	0.1015 (5)	0.0632 (4)	0.0687 (4)	0.0485 (3)	0.0365 (3)	0.0383 (3)
Cl2	0.0983 (5)	0.0790 (4)	0.0432 (3)	0.0402 (4)	0.0328 (3)	0.0210 (3)
O1	0.0915 (11)	0.0354 (7)	0.0465 (7)	0.0342 (7)	0.0276 (7)	0.0082 (6)
O2	0.0787 (9)	0.0325 (6)	0.0424 (7)	0.0290 (7)	0.0265 (7)	0.0083 (5)
C1	0.0470 (10)	0.0319 (8)	0.0425 (9)	0.0168 (7)	0.0144 (8)	0.0071 (7)
C2	0.0458 (10)	0.0374 (9)	0.0463 (10)	0.0174 (8)	0.0124 (8)	0.0157 (8)
C3	0.0481 (10)	0.0473 (10)	0.0360 (9)	0.0161 (9)	0.0139 (8)	0.0095 (8)
C4	0.0577 (11)	0.0426 (10)	0.0434 (10)	0.0216 (9)	0.0186 (9)	0.0037 (8)
C5	0.0536 (11)	0.0330 (8)	0.0415 (9)	0.0189 (8)	0.0153 (8)	0.0072 (7)
C6	0.0388 (9)	0.0281 (8)	0.0370 (8)	0.0121 (7)	0.0098 (7)	0.0048 (6)
C7	0.0440 (9)	0.0277 (8)	0.0390 (9)	0.0139 (7)	0.0118 (7)	0.0038 (7)
C8	0.0511 (10)	0.0261 (8)	0.0384 (9)	0.0158 (7)	0.0142 (8)	0.0037 (7)
C9	0.0514 (10)	0.0286 (8)	0.0380 (9)	0.0162 (7)	0.0123 (8)	0.0010 (7)
C10	0.0446 (9)	0.0329 (8)	0.0338 (8)	0.0143 (7)	0.0102 (7)	0.0039 (7)
C11	0.0423 (9)	0.0323 (8)	0.0359 (8)	0.0145 (7)	0.0121 (7)	0.0050 (7)
C12	0.0612 (12)	0.0397 (9)	0.0470 (10)	0.0247 (9)	0.0177 (9)	0.0135 (8)
C13	0.0765 (14)	0.0579 (12)	0.0472 (11)	0.0302 (11)	0.0180 (10)	0.0249 (10)
C14	0.0867 (16)	0.0629 (13)	0.0332 (9)	0.0297 (12)	0.0182 (10)	0.0101 (9)
C15	0.0771 (14)	0.0440 (10)	0.0370 (9)	0.0270 (10)	0.0180 (9)	0.0025 (8)

Cl1—C2	1.7294 (17)	C7—C8	1.467 (2)
Cl2—C3	1.7241 (18)	C8—C9	1.330 (2)
O1—C7	1.226 (2)	C8—H8A	0.9300
O2—C11	1.358 (2)	C9—C10	1.448 (2)
O2—H2O	0.842 (16)	C9—H9A	0.9300
C1—C2	1.372 (2)	C10—C15	1.401 (2)
C1—C6	1.392 (2)	C10—C11	1.404 (2)
C1—H1A	0.9300	C11—C12	1.390 (2)
C2—C3	1.388 (3)	C12—C13	1.371 (3)
C3—C4	1.382 (3)	C12—H12A	0.9300
C4—C5	1.378 (2)	C13—C14	1.382 (3)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.393 (2)	C14—C15	1.369 (3)
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.489 (2)	C15—H15A	0.9300
C11—O2—H2O	110.9 (15)	C9—C8—H8A	120.1
C2—C1—C6	120.90 (16)	C7—C8—H8A	120.1
C2—C1—H1A	119.6	C8—C9—C10	131.19 (15)
C6—C1—H1A	119.6	C8—C9—H9A	114.4
C1—C2—C3	120.06 (16)	C10—C9—H9A	114.4
C1—C2—Cl1	119.25 (14)	C15—C10—C11	117.39 (16)
C3—C2—Cl1	120.68 (14)	C15—C10—C9	117.66 (15)
C4—C3—C2	119.71 (16)	C11—C10—C9	124.96 (15)
C4—C3—Cl2	119.09 (14)	O2—C11—C12	121.68 (15)
C2—C3—Cl2	121.19 (14)	O2—C11—C10	118.26 (14)
C5—C4—C3	120.17 (16)	C12—C11—C10	120.06 (15)
C5—C4—H4A	119.9	C13—C12—C11	120.70 (17)
C3—C4—H4A	119.9	C13—C12—H12A	119.7
C4—C5—C6	120.58 (16)	C11—C12—H12A	119.7
C4—C5—H5A	119.7	C12—C13—C14	120.29 (18)
C6—C5—H5A	119.7	C12—C13—H13A	119.9
C1—C6—C5	118.56 (15)	C14—C13—H13A	119.9
C1—C6—C7	118.09 (14)	C15—C14—C13	119.36 (18)
C5—C6—C7	123.35 (14)	C15—C14—H14A	120.3
O1—C7—C8	120.65 (15)	C13—C14—H14A	120.3
O1—C7—C6	119.13 (14)	C14—C15—C10	122.21 (18)
C8—C7—C6	120.22 (14)	C14—C15—H15A	118.9
C9—C8—C7	119.71 (15)	C10—C15—H15A	118.9
C6—C1—C2—C3	−0.6 (3)	O1—C7—C8—C9	−3.9 (3)
C6—C1—C2—Cl1	178.20 (14)	C6—C7—C8—C9	175.47 (17)
C1—C2—C3—C4	0.8 (3)	C7—C8—C9—C10	−177.56 (18)
Cl1—C2—C3—C4	−177.92 (15)	C8—C9—C10—C15	178.7 (2)
C1—C2—C3—Cl2	−178.34 (14)	C8—C9—C10—C11	−0.9 (3)
Cl1—C2—C3—Cl2	2.9 (2)	C15—C10—C11—O2	179.76 (17)
C2—C3—C4—C5	−0.1 (3)	C9—C10—C11—O2	−0.6 (3)
Cl2—C3—C4—C5	179.07 (15)	C15—C10—C11—C12	−0.2 (3)
C3—C4—C5—C6	−0.9 (3)	C9—C10—C11—C12	179.39 (18)
C2—C1—C6—C5	−0.4 (3)	O2—C11—C12—C13	179.89 (18)
C2—C1—C6—C7	179.74 (17)	C10—C11—C12—C13	−0.1 (3)
C4—C5—C6—C1	1.1 (3)	C11—C12—C13—C14	0.2 (3)
C4—C5—C6—C7	−179.04 (17)	C12—C13—C14—C15	0.1 (4)
C1—C6—C7—O1	−5.7 (3)	C13—C14—C15—C10	−0.5 (4)
C5—C6—C7—O1	174.48 (18)	C11—C10—C15—C14	0.5 (3)
C1—C6—C7—C8	174.96 (16)	C9—C10—C15—C14	−179.1 (2)
C5—C6—C7—C8	−4.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1i	0.84 (2)	1.88 (2)	2.7168 (17)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1i	0.84 (2)	1.88 (2)	2.7168 (17)	176 (2)

Symmetry code: (i) .