(2E)-1-(3-Chloro­phen­yl)-3-phenyl­prop-2-en-1-one

Jasinski, J.P.; Butcher, R.J.; Narayana, B.; Veena, K.; Yathirajan, H.S.

doi:10.1107/S1600536809053458

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o157

doi:10.1107/S1600536809053458

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(2E)-1-(3-Chlorophenyl)-3-phenylprop-2-en-1-one

Jerry P. Jasinski,^a ^* Ray J. Butcher,^b B. Narayana,^c K. Veena ^c and H. S. Yathirajan ^d

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, ^cDepartment of Studies in Chemistry, Mangalore University, Manalaganotri 574 199, India, and ^dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 5 December 2009; accepted 11 December 2009; online 16 December 2009)

In the title compound, C₁₅H₁₁ClO, the dihedral angle between the mean planes of the benzene ring and the chloro-substituted benzene ring is 48.8 (3)°. The dihedral angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 3-chlorophenyl and benzene rings are 27.0 (4) and 27.9 (3)°, respectively. In the crystal, weak intermolecular C—H⋯π-ring interactions occur.

Related literature

For background to chalcones, see: Chen et al. (1994 ); Marais et al. (2005 ); Poornesh et al. (2009 ); Ram et al. (2000 ); Sarojini et al. (2006 ); Shettigar et al. (2006 , 2008 ); Troeberg et al. (2000 ). For related structures, see: Jasinski et al. (2007 ); Li & Su (1994 ).

Experimental

Crystal data

C₁₅H₁₁ClO
M_r = 242.69
Triclinic, $[P \overline 1]$
a = 5.8388 (7) Å
b = 7.5975 (11) Å
c = 13.1300 (16) Å
α = 83.182 (11)°
β = 89.422 (10)°
γ = 86.662 (11)°
V = 577.35 (13) Å³
Z = 2
Cu Kα radiation
μ = 2.74 mm⁻¹
T = 110 K
0.50 × 0.32 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.541, T_max = 1.000
3661 measured reflections
2243 independent reflections
2148 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.099
S = 1.02
2243 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯Cg2ⁱ	0.95	2.90	3.5541 (16)	127
C5—H5A⋯Cg2ⁱⁱ	0.95	2.90	3.5338 (17)	125
C12—H12A⋯Cg1ⁱⁱⁱ	0.95	2.92	3.6040 (17)	130
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x+2, -y+1, -z+2; (iii) -x+2, -y+2, -z+2. Cg1 is the centroid of the C1–C6 ring and Cg2 is the centroid of the C10–C15 ring.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; 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/S1600536809053458/tk2596sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809053458/tk2596Isup2.hkl

checkCIF report

Comment top

Chalcones are known as the precursors of all flavonoid type natural products in biosynthesis (Marais et al., 2005). Chalcones exhibit various biological activities like insecticidal, antimicrobial, antichinoviral, antipicorniviral and bacteriostatic properties. Azachalcones, the derivatives of chalcones with an annular nitrogen atom in the phenyl ring, were reported to have a wide range of biological activities, such as antibacterial, antituberculostatic and anti-inflammatory. An important feature of chalcones are their ability to act as activated unsaturated systems in conjugated addition of carbanions in presence of suitable basic catalysts. Many chalcones have been described for their high antimalarial activity, probably as a result of Michael addition of nucleophilic species to the double bond of the enone (Troeberg et al., 2000; Ram et al., 2000). Licochalcone A, isolated from Chinese liquorice roots, has been reported as being highly effective in chloroquine resistant Plasmodium falciparum strains in a [3H] hypoxanthine uptake assay (Chen et al., 1994). Chalcones are also finding applications as organic non-linear optical materials (NLO) due to their good SHG conversion efficiencies (Sarojini et al., 2006). Recently, non-linear optical studies on a few chalcones and their derivatives were reported (Poornesh et al., 2009; Shettigar et al., 2006; 2008). In continuation with our studies of chalcones (Jasinski et al., 2007) and their derivatives and owing to the importance of these flavanoid analogs, the title chalcone, (I), was synthesized and its crystal structure reported herein.

The title compound, (I), is a chalcone with 3-chlorophenyl and benzene rings bonded at the opposite ends of a propenone group, the biologically active region (Fig.1). The dihedral angle between mean planes of the benzene and chloro substituted benzene rings is 48.8 (3)° as compared to 14.3 (7)° in the 4-chloro benzene analogue compound (Li & Su, 1994). The angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 3-chlorophenyl and benzene rings are 27.0 (4)° and 27.9 (3)°, respectively, as compared to 19.4 (2)° and 11.9 (9)° in the aforementioned 4-chloro benzene compound. While no classical hydrogen bonds are present, weak intermolecular C–H···π-ring interactions are observed which contribute to the stability of crystal packing (Table 1).

Related literature top

For background to chalcones, see: Chen et al. (1994); Marais et al. (2005); Poornesh et al. (2009); Ram et al. (2000); Sarojini et al. (2006); Shettigar et al. (2006, 2008); Troeberg et al. (2000). For related structures, see: Jasinski et al. (2007); Li & Su (1994).

Experimental top

50% KOH was added to a mixture of 3-chloro acetophenone (0.01 mol) and benzaldehyde (0.01 mol) in 25 ml of ethanol (Scheme 2). The mixture was stirred for an hour at room temperature and the precipitate was collected by filtration and purified by recrystallization from ethanol. The single-crystal was grown from ethyl acetate by slow evaporation method and yield of the compound was 72% (m.p.: 354–356 K). Analytical data for C₁₅H₁₁ClO: Found (Calculated): C%: 74.19 (74.23); H%: 4.55 (4.57).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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 (I), showing the atom labeling scheme and 50% probability displacement ellipsoids.

(2E)-1-(3-Chlorophenyl)-3-phenylprop-2-en-1-one top

Crystal data top

C₁₅H₁₁ClO	Z = 2
M_r = 242.69	F(000) = 252
Triclinic, P1	D_x = 1.396 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 5.8388 (7) Å	Cell parameters from 3077 reflections
b = 7.5975 (11) Å	θ = 5.9–73.8°
c = 13.1300 (16) Å	µ = 2.74 mm⁻¹
α = 83.182 (11)°	T = 110 K
β = 89.422 (10)°	Prism, colorless
γ = 86.662 (11)°	0.50 × 0.32 × 0.28 mm
V = 577.35 (13) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	2243 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2148 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Detector resolution: 10.5081 pixels mm^-1	θ_max = 73.8°, θ_min = 5.9°
ω scans	h = −7→5
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −9→9
T_min = 0.541, T_max = 1.000	l = −16→15
3661 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0647P)² + 0.2987P] where P = (F_o² + 2F_c²)/3
2243 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₅H₁₁ClO	γ = 86.662 (11)°
M_r = 242.69	V = 577.35 (13) Å³
Triclinic, P1	Z = 2
a = 5.8388 (7) Å	Cu Kα radiation
b = 7.5975 (11) Å	µ = 2.74 mm⁻¹
c = 13.1300 (16) Å	T = 110 K
α = 83.182 (11)°	0.50 × 0.32 × 0.28 mm
β = 89.422 (10)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	2243 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2148 reflections with I > 2σ(I)
T_min = 0.541, T_max = 1.000	R_int = 0.017
3661 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.02	Δρ_max = 0.34 e Å⁻³
2243 reflections	Δρ_min = −0.22 e Å⁻³
154 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
Cl	0.32652 (6)	0.68985 (5)	0.56518 (3)	0.02296 (15)
O	0.27901 (18)	0.72419 (15)	0.96930 (8)	0.0224 (3)
C1	0.5736 (2)	0.67070 (18)	0.84979 (11)	0.0160 (3)
C2	0.4270 (2)	0.69988 (18)	0.76536 (11)	0.0162 (3)
H2A	0.2759	0.7510	0.7719	0.019*
C3	0.5060 (3)	0.65289 (19)	0.67198 (11)	0.0165 (3)
C4	0.7258 (3)	0.57602 (19)	0.66031 (12)	0.0189 (3)
H4A	0.7771	0.5448	0.5956	0.023*
C5	0.8677 (3)	0.54612 (19)	0.74507 (12)	0.0193 (3)
H5A	1.0170	0.4916	0.7387	0.023*
C6	0.7950 (2)	0.59463 (19)	0.83940 (12)	0.0177 (3)
H6A	0.8955	0.5762	0.8966	0.021*
C7	0.4848 (3)	0.72066 (19)	0.95085 (11)	0.0175 (3)
C8	0.6548 (3)	0.7663 (2)	1.02521 (12)	0.0192 (3)
H8A	0.8081	0.7850	1.0035	0.023*
C9	0.5952 (2)	0.78129 (19)	1.12239 (11)	0.0170 (3)
H9A	0.4423	0.7560	1.1418	0.020*
C10	0.7434 (2)	0.83314 (19)	1.20198 (11)	0.0161 (3)
C11	0.9534 (3)	0.90987 (19)	1.17865 (11)	0.0180 (3)
H11A	1.0036	0.9293	1.1094	0.022*
C12	1.0875 (3)	0.95730 (19)	1.25607 (12)	0.0194 (3)
H12A	1.2287	1.0103	1.2396	0.023*
C13	1.0172 (3)	0.9280 (2)	1.35792 (12)	0.0217 (3)
H13A	1.1107	0.9600	1.4108	0.026*
C14	0.8103 (3)	0.8519 (2)	1.38218 (12)	0.0221 (3)
H14A	0.7623	0.8313	1.4517	0.026*
C15	0.6734 (3)	0.80576 (19)	1.30478 (12)	0.0185 (3)
H15A	0.5309	0.7552	1.3217	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0222 (2)	0.0308 (2)	0.0164 (2)	0.00195 (15)	−0.00390 (14)	−0.00610 (14)
O	0.0149 (5)	0.0340 (6)	0.0190 (5)	−0.0032 (4)	0.0000 (4)	−0.0044 (4)
C1	0.0171 (7)	0.0139 (6)	0.0173 (7)	−0.0054 (5)	0.0001 (5)	−0.0010 (5)
C2	0.0140 (7)	0.0149 (7)	0.0198 (7)	−0.0028 (5)	0.0000 (5)	−0.0019 (5)
C3	0.0177 (7)	0.0173 (7)	0.0152 (7)	−0.0036 (5)	−0.0023 (5)	−0.0031 (5)
C4	0.0209 (7)	0.0165 (7)	0.0203 (7)	−0.0034 (5)	0.0034 (6)	−0.0050 (6)
C5	0.0145 (7)	0.0156 (7)	0.0277 (8)	−0.0003 (5)	0.0009 (6)	−0.0030 (6)
C6	0.0161 (7)	0.0160 (7)	0.0208 (7)	−0.0032 (5)	−0.0023 (5)	−0.0001 (5)
C7	0.0175 (7)	0.0168 (7)	0.0179 (7)	−0.0030 (5)	−0.0005 (5)	−0.0002 (5)
C8	0.0166 (7)	0.0213 (7)	0.0199 (7)	−0.0033 (6)	−0.0009 (6)	−0.0023 (6)
C9	0.0143 (7)	0.0154 (7)	0.0212 (7)	−0.0003 (5)	−0.0004 (5)	−0.0021 (5)
C10	0.0155 (7)	0.0139 (6)	0.0188 (7)	0.0015 (5)	−0.0010 (5)	−0.0030 (5)
C11	0.0173 (7)	0.0175 (7)	0.0189 (7)	−0.0001 (5)	0.0011 (5)	−0.0024 (5)
C12	0.0161 (7)	0.0156 (7)	0.0264 (8)	−0.0011 (5)	−0.0017 (6)	−0.0020 (6)
C13	0.0228 (8)	0.0201 (7)	0.0227 (8)	0.0003 (6)	−0.0064 (6)	−0.0046 (6)
C14	0.0268 (8)	0.0221 (8)	0.0171 (7)	0.0001 (6)	0.0010 (6)	−0.0027 (6)
C15	0.0172 (7)	0.0166 (7)	0.0220 (8)	−0.0010 (5)	0.0029 (6)	−0.0032 (6)

Geometric parameters (Å, º) top

Cl—C3	1.7452 (15)	C8—H8A	0.9500
O—C7	1.2226 (19)	C9—C10	1.467 (2)
C1—C2	1.396 (2)	C9—H9A	0.9500
C1—C6	1.397 (2)	C10—C15	1.402 (2)
C1—C7	1.502 (2)	C10—C11	1.404 (2)
C2—C3	1.385 (2)	C11—C12	1.383 (2)
C2—H2A	0.9500	C11—H11A	0.9500
C3—C4	1.393 (2)	C12—C13	1.391 (2)
C4—C5	1.383 (2)	C12—H12A	0.9500
C4—H4A	0.9500	C13—C14	1.387 (2)
C5—C6	1.389 (2)	C13—H13A	0.9500
C5—H5A	0.9500	C14—C15	1.389 (2)
C6—H6A	0.9500	C14—H14A	0.9500
C7—C8	1.483 (2)	C15—H15A	0.9500
C8—C9	1.335 (2)

C2—C1—C6	120.12 (14)	C7—C8—H8A	119.6
C2—C1—C7	118.15 (13)	C8—C9—C10	126.15 (14)
C6—C1—C7	121.73 (13)	C8—C9—H9A	116.9
C3—C2—C1	118.72 (13)	C10—C9—H9A	116.9
C3—C2—H2A	120.6	C15—C10—C11	118.75 (13)
C1—C2—H2A	120.6	C15—C10—C9	119.08 (13)
C2—C3—C4	121.96 (13)	C11—C10—C9	122.18 (13)
C2—C3—Cl	119.50 (11)	C12—C11—C10	120.27 (14)
C4—C3—Cl	118.54 (11)	C12—C11—H11A	119.9
C5—C4—C3	118.53 (14)	C10—C11—H11A	119.9
C5—C4—H4A	120.7	C11—C12—C13	120.46 (14)
C3—C4—H4A	120.7	C11—C12—H12A	119.8
C4—C5—C6	120.91 (14)	C13—C12—H12A	119.8
C4—C5—H5A	119.5	C14—C13—C12	119.92 (14)
C6—C5—H5A	119.5	C14—C13—H13A	120.0
C5—C6—C1	119.74 (14)	C12—C13—H13A	120.0
C5—C6—H6A	120.1	C13—C14—C15	119.97 (14)
C1—C6—H6A	120.1	C13—C14—H14A	120.0
O—C7—C8	122.19 (14)	C15—C14—H14A	120.0
O—C7—C1	120.25 (13)	C14—C15—C10	120.63 (14)
C8—C7—C1	117.56 (13)	C14—C15—H15A	119.7
C9—C8—C7	120.80 (14)	C10—C15—H15A	119.7
C9—C8—H8A	119.6

C6—C1—C2—C3	−0.3 (2)	O—C7—C8—C9	12.5 (2)
C7—C1—C2—C3	−179.41 (12)	C1—C7—C8—C9	−168.11 (14)
C1—C2—C3—C4	0.7 (2)	C7—C8—C9—C10	−177.12 (13)
C1—C2—C3—Cl	−179.48 (10)	C8—C9—C10—C15	−166.17 (15)
C2—C3—C4—C5	0.1 (2)	C8—C9—C10—C11	14.0 (2)
Cl—C3—C4—C5	−179.76 (11)	C15—C10—C11—C12	0.0 (2)
C3—C4—C5—C6	−1.2 (2)	C9—C10—C11—C12	179.79 (13)
C4—C5—C6—C1	1.6 (2)	C10—C11—C12—C13	0.6 (2)
C2—C1—C6—C5	−0.8 (2)	C11—C12—C13—C14	−0.5 (2)
C7—C1—C6—C5	178.26 (12)	C12—C13—C14—C15	−0.2 (2)
C2—C1—C7—O	26.0 (2)	C13—C14—C15—C10	0.9 (2)
C6—C1—C7—O	−153.08 (14)	C11—C10—C15—C14	−0.7 (2)
C2—C1—C7—C8	−153.42 (13)	C9—C10—C15—C14	179.46 (13)
C6—C1—C7—C8	27.50 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring and Cg2 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···Cg2ⁱ	0.95	2.90	3.5541 (16)	127
C5—H5A···Cg2ⁱⁱ	0.95	2.90	3.5338 (17)	125
C12—H12A···Cg1ⁱⁱⁱ	0.95	2.92	3.6040 (17)	130

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+2, −y+1, −z+2; (iii) −x+2, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁ClO
M_r	242.69
Crystal system, space group	Triclinic, P1
Temperature (K)	110
a, b, c (Å)	5.8388 (7), 7.5975 (11), 13.1300 (16)
α, β, γ (°)	83.182 (11), 89.422 (10), 86.662 (11)
V (Å³)	577.35 (13)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.74
Crystal size (mm)	0.50 × 0.32 × 0.28

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.541, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3661, 2243, 2148
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.099, 1.02
No. of reflections	2243
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.22

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97) (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring and Cg2 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···Cg2ⁱ	0.95	2.90	3.5541 (16)	127
C5—H5A···Cg2ⁱⁱ	0.95	2.90	3.5338 (17)	125
C12—H12A···Cg1ⁱⁱⁱ	0.95	2.92	3.6040 (17)	130

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+2, −y+1, −z+2; (iii) −x+2, −y+2, −z+2.

Acknowledgements

KV thanks the UGC for the sanction of a Junior Research Fellowship and for a SAP Chemical grant. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

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