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

Fun, H.-K.; Jebas, S.R.; Patil, P.S.; Dharmaprakash, S.M.

doi:10.1107/S1600536808011008

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o936

doi:10.1107/S1600536808011008

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

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ‡ P. S. Patil ^b and S. M. Dharmaprakash ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 19 April 2008; accepted 19 April 2008; online 30 April 2008)

The molecule of the title compound, C₁₆H₁₂Cl₂O, adopts an E configuration. The dihedral angle between the two benzene rings is 42.09 (5)°. In the crystal structure, molecules are linked into a three-dimensional framework by weak C—H⋯O interactions and by C—H⋯π interactions involving the methylphenyl ring.

Related literature

For related literature, see: Agrinskaya et al. (1999 ); Gu et al. (2008 ); Patil et al. (2006 ); Patil, Dharmaprakash et al. (2007 ); Patil, Teh et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₂Cl₂O
M_r = 291.16
Orthorhombic, P b c a
a = 12.54850 (1) Å
b = 7.47750 (1) Å
c = 28.7764 (3) Å
V = 2700.13 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 100.0 (1) K
0.47 × 0.39 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.811, T_max = 0.914
50054 measured reflections
7296 independent reflections
4995 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.148
S = 1.07
7296 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.93	2.55	3.4352 (15)	159
C8—H8⋯O1ⁱⁱ	0.93	2.55	3.1995 (14)	127
C11—H11⋯Cg1ⁱⁱⁱ	0.93	2.81	3.5611 (13)	139
C14—H14⋯Cg1^iv	0.93	2.93	3.7066 (13)	142
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C10–C15 benzene ring.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011008/ci2584sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011008/ci2584Isup2.hkl

checkCIF report

Comment top

Chalcone derivatives have been studied extensively owing to their fascinating, technologically relevant nonlinear optical properties (Gu et al., 2008; Agrinskaya et al., 1999; Patil et al., 2006; Patil, Dharmaprakash et al., 2007; Patil, Teh et al., 2007).

The title molecule exhibits an E configuration with respect to the C8═C9 double bond [1.3424 (14) Å]; the C7—C8—-C9—-C10 torsion angle is 179.61 (11)°. The dihedral angle between the two benzene rings is 42.09 (5)°. The bond lengths and angles in the title molecule have normal values.

The crystal structure is stabilized by weak C—H···O intermolecular hydrogen bonding interactions (Table 1), which link the molecules into a three-dimensional framework (Fig. 2). In addition weak C—H..π interactions involving the C10—C15 benzene ring (centroid Cg1) is observed.

Related literature top

For related literature, see: Agrinskaya et al. (1999); Gu et al. (2008); Patil et al. (2006); Patil, Dharmaprakash et al. (2007); Patil, Teh et al. (2007). Cg1 is the centroid of the C10–C15 benzene ring.

Experimental top

The title compound was synthesized by the condensation of p-tolualdehyde (0.01 mol) with 2,4-dichloroacetophenone (0.01 mol) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring for 2 h, the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 5 h. The resulting crude solid was collected by filtration and dried. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of an acetone solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed approximately along the a axis. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₆H₁₂Cl₂O	F(000) = 1200
M_r = 291.16	D_x = 1.432 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9639 reflections
a = 12.54850 (1) Å	θ = 2.8–34.6°
b = 7.47750 (1) Å	µ = 0.47 mm⁻¹
c = 28.7764 (3) Å	T = 100 K
V = 2700.13 (3) Å³	Block, colourless
Z = 8	0.47 × 0.39 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7296 independent reflections
Radiation source: fine-focus sealed tube	4995 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ϕ and ω scans	θ_max = 37.9°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −21→21
T_min = 0.811, T_max = 0.914	k = −12→12
50054 measured reflections	l = −48→49

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.078P)² + 0.0443P] where P = (F_o² + 2F_c²)/3
7296 reflections	(Δ/σ)_max = 0.001
173 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₁₆H₁₂Cl₂O	V = 2700.13 (3) Å³
M_r = 291.16	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.54850 (1) Å	µ = 0.47 mm⁻¹
b = 7.47750 (1) Å	T = 100 K
c = 28.7764 (3) Å	0.47 × 0.39 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7296 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4995 reflections with I > 2σ(I)
T_min = 0.811, T_max = 0.914	R_int = 0.052
50054 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.07	Δρ_max = 0.64 e Å⁻³
7296 reflections	Δρ_min = −0.53 e Å⁻³
173 parameters

Special details top

Experimental. The 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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.46470 (2)	0.76088 (4)	0.057148 (10)	0.02125 (8)
Cl2	0.36980 (3)	0.56187 (5)	−0.116828 (9)	0.02538 (9)
O1	0.13288 (7)	0.72551 (12)	0.08499 (3)	0.02032 (17)
C1	0.37202 (9)	0.67308 (15)	0.01850 (4)	0.0158 (2)
C2	0.40554 (10)	0.64861 (15)	−0.02709 (4)	0.0177 (2)
H2	0.4759	0.6696	−0.0356	0.021*
C3	0.33080 (10)	0.59184 (15)	−0.05947 (4)	0.0177 (2)
C4	0.22518 (9)	0.56292 (16)	−0.04764 (4)	0.0183 (2)
H4	0.1760	0.5265	−0.0699	0.022*
C5	0.19470 (9)	0.58948 (15)	−0.00210 (4)	0.0173 (2)
H5	0.1238	0.5715	0.0060	0.021*
C6	0.26690 (9)	0.64245 (14)	0.03220 (3)	0.01531 (19)
C7	0.22310 (9)	0.66606 (15)	0.08060 (4)	0.0165 (2)
C8	0.28861 (9)	0.60913 (15)	0.12039 (4)	0.0168 (2)
H8	0.3512	0.5458	0.1151	0.020*
C9	0.25956 (10)	0.64712 (15)	0.16419 (4)	0.0168 (2)
H9	0.1962	0.7100	0.1680	0.020*
C10	0.31720 (9)	0.59981 (15)	0.20655 (4)	0.01556 (19)
C11	0.27256 (10)	0.64353 (15)	0.24970 (4)	0.0179 (2)
H11	0.2075	0.7031	0.2508	0.021*
C12	0.32405 (10)	0.59919 (16)	0.29076 (4)	0.0189 (2)
H12	0.2929	0.6294	0.3190	0.023*
C13	0.42150 (10)	0.51030 (16)	0.29039 (4)	0.0182 (2)
C14	0.46702 (9)	0.46835 (16)	0.24731 (4)	0.0185 (2)
H14	0.5325	0.4102	0.2463	0.022*
C15	0.41598 (9)	0.51215 (16)	0.20617 (4)	0.0177 (2)
H15	0.4476	0.4831	0.1779	0.021*
C16	0.47564 (11)	0.45835 (18)	0.33516 (4)	0.0251 (3)
H16A	0.4802	0.5608	0.3552	0.038*
H16B	0.5460	0.4149	0.3286	0.038*
H16C	0.4352	0.3662	0.3503	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01778 (15)	0.02973 (16)	0.01623 (13)	−0.00376 (10)	−0.00292 (9)	−0.00163 (10)
Cl2	0.02586 (17)	0.03750 (18)	0.01277 (12)	0.00235 (12)	0.00091 (10)	−0.00154 (10)
O1	0.0168 (4)	0.0256 (4)	0.0185 (4)	0.0022 (3)	−0.0001 (3)	−0.0017 (3)
C1	0.0158 (5)	0.0171 (5)	0.0145 (4)	0.0009 (4)	−0.0025 (4)	−0.0003 (3)
C2	0.0158 (5)	0.0216 (5)	0.0157 (4)	0.0016 (4)	0.0004 (4)	0.0001 (4)
C3	0.0213 (6)	0.0200 (5)	0.0117 (4)	0.0020 (4)	−0.0010 (4)	0.0007 (3)
C4	0.0183 (5)	0.0210 (5)	0.0156 (4)	−0.0001 (4)	−0.0043 (4)	−0.0007 (4)
C5	0.0166 (5)	0.0198 (5)	0.0154 (4)	−0.0007 (4)	−0.0014 (4)	0.0005 (4)
C6	0.0177 (5)	0.0155 (4)	0.0127 (4)	0.0013 (4)	−0.0010 (4)	0.0012 (3)
C7	0.0191 (5)	0.0152 (4)	0.0153 (4)	−0.0006 (4)	0.0005 (4)	−0.0008 (3)
C8	0.0188 (5)	0.0172 (5)	0.0144 (4)	0.0018 (4)	0.0001 (4)	0.0001 (3)
C9	0.0170 (5)	0.0173 (5)	0.0159 (4)	−0.0006 (4)	0.0003 (4)	−0.0001 (3)
C10	0.0177 (5)	0.0163 (4)	0.0127 (4)	−0.0004 (4)	0.0012 (4)	−0.0001 (3)
C11	0.0180 (5)	0.0200 (5)	0.0156 (4)	0.0021 (4)	0.0006 (4)	−0.0008 (4)
C12	0.0222 (6)	0.0218 (5)	0.0126 (4)	0.0004 (4)	0.0013 (4)	−0.0008 (4)
C13	0.0204 (6)	0.0184 (5)	0.0158 (5)	−0.0024 (4)	−0.0019 (4)	0.0007 (4)
C14	0.0168 (5)	0.0207 (5)	0.0179 (5)	0.0013 (4)	0.0002 (4)	0.0001 (4)
C15	0.0175 (5)	0.0209 (5)	0.0149 (4)	0.0013 (4)	0.0009 (4)	−0.0002 (4)
C16	0.0284 (7)	0.0290 (6)	0.0179 (5)	0.0016 (5)	−0.0058 (5)	0.0011 (4)

Geometric parameters (Å, º) top

Cl1—C1	1.7380 (11)	C9—C10	1.4609 (15)
Cl2—C3	1.7360 (11)	C9—H9	0.93
O1—C7	1.2228 (14)	C10—C11	1.4008 (15)
C1—C2	1.3895 (15)	C10—C15	1.4022 (17)
C1—C6	1.3957 (16)	C11—C12	1.3871 (16)
C2—C3	1.3887 (16)	C11—H11	0.93
C2—H2	0.93	C12—C13	1.3919 (18)
C3—C4	1.3854 (17)	C12—H12	0.93
C4—C5	1.3795 (15)	C13—C14	1.4006 (16)
C4—H4	0.93	C13—C16	1.5072 (16)
C5—C6	1.3971 (15)	C14—C15	1.3855 (16)
C5—H5	0.93	C14—H14	0.93
C6—C7	1.5077 (15)	C15—H15	0.93
C7—C8	1.4725 (15)	C16—H16A	0.96
C8—C9	1.3424 (14)	C16—H16B	0.96
C8—H8	0.93	C16—H16C	0.96

C2—C1—C6	122.08 (10)	C10—C9—H9	116.6
C2—C1—Cl1	116.83 (9)	C11—C10—C15	118.00 (10)
C6—C1—Cl1	120.90 (8)	C11—C10—C9	119.02 (10)
C3—C2—C1	118.00 (11)	C15—C10—C9	122.98 (10)
C3—C2—H2	121.0	C12—C11—C10	120.88 (11)
C1—C2—H2	121.0	C12—C11—H11	119.6
C4—C3—C2	121.92 (10)	C10—C11—H11	119.6
C4—C3—Cl2	118.90 (9)	C11—C12—C13	121.12 (10)
C2—C3—Cl2	119.15 (10)	C11—C12—H12	119.4
C5—C4—C3	118.45 (10)	C13—C12—H12	119.4
C5—C4—H4	120.8	C12—C13—C14	118.17 (10)
C3—C4—H4	120.8	C12—C13—C16	120.83 (10)
C4—C5—C6	122.15 (11)	C14—C13—C16	120.99 (11)
C4—C5—H5	118.9	C15—C14—C13	121.00 (11)
C6—C5—H5	118.9	C15—C14—H14	119.5
C1—C6—C5	117.38 (10)	C13—C14—H14	119.5
C1—C6—C7	125.90 (10)	C14—C15—C10	120.83 (10)
C5—C6—C7	116.70 (10)	C14—C15—H15	119.6
O1—C7—C8	122.79 (10)	C10—C15—H15	119.6
O1—C7—C6	118.40 (10)	C13—C16—H16A	109.5
C8—C7—C6	118.75 (10)	C13—C16—H16B	109.5
C9—C8—C7	121.15 (11)	H16A—C16—H16B	109.5
C9—C8—H8	119.4	C13—C16—H16C	109.5
C7—C8—H8	119.4	H16A—C16—H16C	109.5
C8—C9—C10	126.71 (11)	H16B—C16—H16C	109.5
C8—C9—H9	116.6

C6—C1—C2—C3	0.00 (17)	C5—C6—C7—C8	141.55 (11)
Cl1—C1—C2—C3	−175.09 (9)	O1—C7—C8—C9	−11.25 (18)
C1—C2—C3—C4	1.20 (17)	C6—C7—C8—C9	171.61 (10)
C1—C2—C3—Cl2	179.44 (9)	C7—C8—C9—C10	−179.61 (11)
C2—C3—C4—C5	−0.88 (17)	C8—C9—C10—C11	−177.16 (12)
Cl2—C3—C4—C5	−179.12 (9)	C8—C9—C10—C15	2.91 (19)
C3—C4—C5—C6	−0.67 (17)	C15—C10—C11—C12	−0.83 (17)
C2—C1—C6—C5	−1.44 (17)	C9—C10—C11—C12	179.24 (11)
Cl1—C1—C6—C5	173.45 (9)	C10—C11—C12—C13	0.09 (19)
C2—C1—C6—C7	−179.70 (10)	C11—C12—C13—C14	0.69 (18)
Cl1—C1—C6—C7	−4.80 (16)	C11—C12—C13—C16	−178.42 (11)
C4—C5—C6—C1	1.79 (17)	C12—C13—C14—C15	−0.73 (18)
C4—C5—C6—C7	−179.80 (10)	C16—C13—C14—C15	178.38 (11)
C1—C6—C7—O1	142.55 (12)	C13—C14—C15—C10	−0.01 (18)
C5—C6—C7—O1	−35.72 (15)	C11—C10—C15—C14	0.79 (17)
C1—C6—C7—C8	−40.19 (15)	C9—C10—C15—C14	−179.29 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.55	3.4352 (15)	159
C8—H8···O1ⁱⁱ	0.93	2.55	3.1995 (14)	127
C11—H11···Cg1ⁱⁱⁱ	0.93	2.81	3.5611 (13)	139
C14—H14···Cg1^iv	0.93	2.93	3.7066 (13)	142

Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) −x+1/2, y−1/2, z; (iii) −x+1/2, y+1/2, z; (iv) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂Cl₂O
M_r	291.16
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	12.54850 (1), 7.47750 (1), 28.7764 (3)
V (Å³)	2700.13 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.47 × 0.39 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.811, 0.914
No. of measured, independent and observed [I > 2σ(I)] reflections	50054, 7296, 4995
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.864

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.148, 1.07
No. of reflections	7296
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.53

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.55	3.4352 (15)	159
C8—H8···O1ⁱⁱ	0.93	2.55	3.1995 (14)	127
C11—H11···Cg1ⁱⁱⁱ	0.93	2.81	3.5611 (13)	139
C14—H14···Cg1^iv	0.93	2.93	3.7066 (13)	142

Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) −x+1/2, y−1/2, z; (iii) −x+1/2, y+1/2, z; (iv) −x+1, y−1/2, −z+1/2.

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for the award of a post-doctoral research fellowship. PSP thanks the DRDO, Government of India, for a Senior Research Fellowship (SRF). This work is also supported by the Department of Science and Technology (DST), Government of India, under grant No. SR/S2/LOP-17/2006.

References

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