(2E)-1-(3,4-Dichloro­phen­yl)-3-(2-hy­droxy­phen­yl)prop-2-en-1-one

Jasinski, J.P.; Golen, J.A.; Nayak, P.S.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536812000505

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o366

doi:10.1107/S1600536812000505

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(2E)-1-(3,4-Dichlorophenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one

Jerry P. Jasinski,^a ^* James A. Golen,^a Prakash S. Nayak,^b B. Narayana ^b and H. S. Yathirajan ^c

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 28 December 2011; accepted 5 January 2012; online 11 January 2012)

In the title compound, C₁₅H₁₀Cl₂O₂, 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 interactions [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_r = 293.13
Triclinic, $[P \overline 1]$
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 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.115
S = 1.01
3174 reflections
175 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) x, y-1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812000505/vm2148sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812000505/vm2148Isup3.cml

checkCIF report

Comment top

Chalcones are abundant in edible plants and considered as the precursors of flavonoids and isoflavonoids. They have also been shown to display a diverse array of pharmacological activities (Dhar, 1981; Nowakowska, 2007) including anti-infective, anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor, anticancer and mutagenic properties (Dimmock et al., 1999; Cheng et al., 2008; Bandgar et al., 2010). The basic skeleton of chalcones which possess an α,β-unsaturated carbonyl group is a useful synthone for the synthesis of various biodynamic cyclic derivatives such as pyrazoline, isoxazoline, 2,4,6-triaryl pyridine, benzodiazepine and cyclohexenone derivatives (Samshuddin et al., 2010; 2011; Fun et al., 2010; Jasinski et al., 2010; Baktır et al., 2011). The crystal structures of some chalcones, viz., (2E)-3-[3-(benzyloxy)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one (Fun et al., 2011), (2E)-3-(4-chlorophenyl)-1-(4-hydroxyphenyl) prop-2-en-1-one (Jasinski et al., 2011), have been reported. In continuation of our studies on chalcones and their derivatives, the title compound (I) was prepared and its crystal structure is reported.

In the title compound, C₁₅H₁₀Cl₂O₂, the dihedral angle between the mean planes of the two benzene rings is 7.7 (6)° (Fig. 1). O—H···O hydrogen bonds (Table 1) are observed between the hydroxyl hydrogen and propene oxygen atoms forming 1-D polymeric chains along [010]. In addition, weak π–π stacking interactions (Cg1···Cg2 distance of 3.6697 (13) Å; Cg1 and Cg2 are the centroids of the C1–C5 ring and C10–C15 ring, respectively) are observed which may contribute to crystal packing stability.

Related literature top

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 top

To a mixture of 2-hydroxybenzaldehyde (1.22 g, 0.01 mol) and 3,4-dichloroacetophenone (1.89 g, 0.01 mol) in ethanol (40 ml), 10 ml of 10% sodium hydroxide solution was added and stirred at 278–288 K for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from DMF by the slow evaporation method. The yield of the compound was 86%. (M.P.: 392 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed along the a axis. Dashed lines indicate O—H···O hydrogen bonding. The remaining hydrogen atoms have been omitted for clarity.

(2E)-1-(3,4-Dichlorophenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₁₀Cl₂O₂	Z = 2
M_r = 293.13	F(000) = 300
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0532P)² + 0.1793P] where P = (F_o² + 2F_c²)/3
3174 reflections	(Δ/σ)_max < 0.001
175 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₅H₁₀Cl₂O₂	γ = 109.011 (8)°
M_r = 293.13	V = 665.51 (10) Å³
Triclinic, P1	Z = 2
a = 7.2551 (6) Å	Mo Kα radiation
b = 7.8351 (7) Å	µ = 0.48 mm⁻¹
c = 12.8049 (11) Å	T = 173 K
α = 92.367 (7)°	0.34 × 0.15 × 0.06 mm
β = 102.946 (8)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3174 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	2417 reflections with I > 2σ(I)
T_min = 0.854, T_max = 0.972	R_int = 0.018
5430 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.30 e Å⁻³
3174 reflections	Δρ_min = −0.26 e Å⁻³
175 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀Cl₂O₂
M_r	293.13
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.2551 (6), 7.8351 (7), 12.8049 (11)
α, β, γ (°)	92.367 (7), 102.946 (8), 109.011 (8)
V (Å³)	665.51 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.34 × 0.15 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.854, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	5430, 3174, 2417
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.115, 1.01
No. of reflections	3174
No. of parameters	175
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.26

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1ⁱ	0.842 (16)	1.876 (16)	2.7168 (17)	176 (2)

Symmetry code: (i) x, y−1, z.

Acknowledgements

PSN thanks Mangalore University for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

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