(E)-3-(2-Chloro­phen­yl)-1-(4-chloro­phen­yl)prop-2-en-1-one

Fun, H.-K.; Jebas, S.R.; Razak, I.A.; Patil, P.S.; Dharmaprakash, S.M.; Deepak D'Silva, E.

doi:10.1107/S1600536808015420

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1177

doi:10.1107/S1600536808015420

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(E)-3-(2-Chlorophenyl)-1-(4-chlorophenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ‡ Ibrahim Abdul Razak,^a P. S. Patil,^b S. M. Dharmaprakash ^b and E. Deepak D'Silva ^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 6 May 2008; accepted 22 May 2008; online 30 May 2008)

The title compound, C₁₅H₁₀Cl₂O, adopts an E configuration with respect to the C=C bond of the propenone unit. The dihedral angle between the two benzene rings is 32.4 (1)°. Intramolecular C—H⋯O and C—H⋯Cl hydrogen bonds generate an S(5)S(5)S(5) motif. In addition, the crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For related literature on chalcones, see: Fun et al. (2007 ); Patil et al. (2007 ). For bond-length data, see: Allen et al. (1987 ). For graph-set motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₀Cl₂O
M_r = 277.13
Orthorhombic, P b c a
a = 7.2777 (1) Å
b = 11.2686 (2) Å
c = 30.2365 (6) Å
V = 2479.68 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 100.0 (1) K
0.51 × 0.34 × 0.19 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.781, T_max = 0.911
42713 measured reflections
5996 independent reflections
4413 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.127
S = 1.05
5996 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯Cl1	0.93	2.65	3.0484 (12)	107
C7—H7A⋯O1	0.93	2.46	2.7973 (15)	101
C15—H15A⋯O1	0.93	2.46	2.7691 (15)	100
C12—H12A⋯O1ⁱ	0.93	2.59	3.2064 (16)	125
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536808015420/lh2627sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015420/lh2627Isup2.hkl

checkCIF report

Comment top

In continuation of our study on chalcone derivatives (Fun et al., 2007; Patil et al., 2007), the crystal structure of the title compound (I) is reported herein.

In (I), the molecule exhibits an E configuration with respect to the C8═C9 double bond with the C7–C8–C9–C10 torsion angle being 163.0 (2) °. The bond lengths in the title compound (Fig. 1) have normal values (Allen et al., 1987). The dihedral angle between the two benzene rings is 32.7 (1)°.

Intramolecular C—H···O and C-H···Cl hydrogen bonds generate an S(5)S(5)S(5) motif (Bernstein et al., 1995). In addition, the crystal structure is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1).

Related literature top

For related literature on chalcones, see: Fun et al. (2007); Patil et al. (2007). For bond-length data, see: Allen et al. (1987). For graph-set motifs, see: Bernstein et al. (1995); .

Experimental top

The compound (I) was synthesized by the condensation of 2 -chlorobenzaldehyde (0.01 mol) with 4-chloroacetophenones (0.01 mol) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring (6 h), the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 12 h. The resulting crude solid was filtered 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. Intramolecular H-bonds are shown as a dashed lines.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis.

(E)-3-(2-Chlorophenyl)-1-(4-chlorophenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₁₀Cl₂O	F(000) = 1136
M_r = 277.13	D_x = 1.485 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8869 reflections
a = 7.2777 (1) Å	θ = 2.7–36.0°
b = 11.2686 (2) Å	µ = 0.51 mm⁻¹
c = 30.2365 (6) Å	T = 100 K
V = 2479.68 (7) Å³	Block, colourless
Z = 8	0.51 × 0.34 × 0.19 mm

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	5996 independent reflections
Radiation source: fine-focus sealed tube	4413 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 36.4°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→12
T_min = 0.781, T_max = 0.911	k = −17→18
42713 measured reflections	l = −50→48

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) = 0.127	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0601P)² + 0.6003P] where P = (F_o² + 2F_c²)/3
5996 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₅H₁₀Cl₂O	V = 2479.68 (7) Å³
M_r = 277.13	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.2777 (1) Å	µ = 0.51 mm⁻¹
b = 11.2686 (2) Å	T = 100 K
c = 30.2365 (6) Å	0.51 × 0.34 × 0.19 mm

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	5996 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4413 reflections with I > 2σ(I)
T_min = 0.781, T_max = 0.911	R_int = 0.042
42713 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.05	Δρ_max = 0.55 e Å⁻³
5996 reflections	Δρ_min = −0.21 e Å⁻³
163 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	0.92678 (5)	0.49110 (3)	0.058017 (10)	0.02768 (8)
Cl2	1.06791 (4)	0.29033 (3)	0.406266 (11)	0.02816 (8)
O1	1.19326 (15)	0.53008 (8)	0.20697 (3)	0.0293 (2)
C1	0.99869 (17)	0.34415 (10)	0.06050 (4)	0.0217 (2)
C2	0.9725 (2)	0.27399 (11)	0.02335 (4)	0.0261 (2)
H2A	0.9233	0.3066	−0.0023	0.031*
C3	1.0200 (2)	0.15500 (11)	0.02468 (5)	0.0295 (3)
H3A	1.0032	0.1074	−0.0001	0.035*
C4	1.0934 (2)	0.10670 (11)	0.06340 (5)	0.0277 (3)
H4A	1.1250	0.0268	0.0644	0.033*
C5	1.11899 (19)	0.17750 (10)	0.10012 (4)	0.0247 (2)
H5A	1.1682	0.1443	0.1257	0.030*
C6	1.07237 (16)	0.29880 (10)	0.09989 (4)	0.0214 (2)
C7	1.10257 (17)	0.37394 (10)	0.13844 (4)	0.0229 (2)
H7A	1.1007	0.4555	0.1337	0.028*
C8	1.13268 (18)	0.33788 (10)	0.17986 (4)	0.0245 (2)
H8A	1.1364	0.2572	0.1863	0.029*
C9	1.16008 (17)	0.42575 (10)	0.21552 (4)	0.0226 (2)
C10	1.14122 (17)	0.38733 (10)	0.26259 (4)	0.0212 (2)
C11	1.10474 (19)	0.27011 (11)	0.27512 (4)	0.0258 (2)
H11A	1.0948	0.2116	0.2536	0.031*
C12	1.08325 (18)	0.24012 (11)	0.31927 (5)	0.0260 (2)
H12A	1.0583	0.1622	0.3274	0.031*
C13	1.09944 (16)	0.32798 (10)	0.35122 (4)	0.0227 (2)
C14	1.13629 (18)	0.44474 (11)	0.33986 (4)	0.0247 (2)
H14A	1.1471	0.5028	0.3616	0.030*
C15	1.15668 (18)	0.47343 (10)	0.29565 (4)	0.0239 (2)
H15A	1.1812	0.5516	0.2878	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.03936 (18)	0.01927 (12)	0.02440 (15)	0.00338 (11)	0.00267 (12)	0.00341 (9)
Cl2	0.03176 (16)	0.02708 (15)	0.02565 (15)	−0.00451 (12)	0.00190 (11)	−0.00078 (10)
O1	0.0399 (5)	0.0181 (4)	0.0299 (5)	−0.0008 (4)	−0.0062 (4)	0.0006 (3)
C1	0.0255 (5)	0.0174 (4)	0.0223 (5)	−0.0004 (4)	0.0031 (4)	0.0014 (4)
C2	0.0355 (6)	0.0228 (5)	0.0201 (5)	−0.0030 (5)	0.0029 (5)	0.0015 (4)
C3	0.0414 (7)	0.0213 (5)	0.0260 (6)	−0.0050 (5)	0.0034 (5)	−0.0026 (4)
C4	0.0362 (7)	0.0171 (5)	0.0299 (6)	−0.0008 (5)	0.0012 (5)	−0.0016 (4)
C5	0.0283 (6)	0.0187 (5)	0.0272 (6)	0.0014 (5)	−0.0011 (5)	0.0006 (4)
C6	0.0219 (5)	0.0186 (5)	0.0236 (5)	−0.0010 (4)	0.0011 (4)	−0.0007 (4)
C7	0.0243 (5)	0.0181 (4)	0.0263 (6)	0.0003 (4)	−0.0021 (4)	−0.0009 (4)
C8	0.0283 (6)	0.0194 (5)	0.0258 (6)	0.0015 (4)	−0.0022 (5)	−0.0022 (4)
C9	0.0244 (5)	0.0182 (4)	0.0253 (6)	0.0022 (4)	−0.0042 (4)	−0.0015 (4)
C10	0.0217 (5)	0.0158 (4)	0.0262 (6)	0.0014 (4)	−0.0026 (4)	−0.0028 (4)
C11	0.0324 (6)	0.0178 (5)	0.0272 (6)	−0.0002 (5)	−0.0003 (5)	−0.0051 (4)
C12	0.0309 (6)	0.0174 (4)	0.0295 (6)	−0.0016 (4)	0.0018 (5)	−0.0020 (4)
C13	0.0223 (5)	0.0208 (5)	0.0251 (6)	−0.0002 (4)	−0.0007 (4)	−0.0015 (4)
C14	0.0281 (6)	0.0195 (5)	0.0264 (6)	−0.0012 (5)	−0.0032 (5)	−0.0039 (4)
C15	0.0274 (5)	0.0168 (4)	0.0275 (6)	−0.0004 (4)	−0.0045 (5)	−0.0019 (4)

Geometric parameters (Å, º) top

Cl1—C1	1.7383 (12)	C7—H7A	0.9300
Cl2—C13	1.7330 (13)	C8—C9	1.4775 (17)
O1—C9	1.2277 (14)	C8—H8A	0.9300
C1—C2	1.3868 (18)	C9—C10	1.4939 (18)
C1—C6	1.4024 (17)	C10—C15	1.3975 (16)
C2—C3	1.3854 (18)	C10—C11	1.3997 (17)
C2—H2A	0.9300	C11—C12	1.3857 (19)
C3—C4	1.397 (2)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C13	1.3883 (18)
C4—C5	1.3800 (18)	C12—H12A	0.9300
C4—H4A	0.9300	C13—C14	1.3860 (17)
C5—C6	1.4084 (16)	C14—C15	1.3834 (19)
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.4574 (17)	C15—H15A	0.9300
C7—C8	1.3347 (18)

C2—C1—C6	122.19 (11)	C9—C8—H8A	119.9
C2—C1—Cl1	117.81 (10)	O1—C9—C8	120.97 (12)
C6—C1—Cl1	119.93 (9)	O1—C9—C10	119.75 (11)
C3—C2—C1	119.60 (12)	C8—C9—C10	119.25 (10)
C3—C2—H2A	120.2	C15—C10—C11	118.47 (12)
C1—C2—H2A	120.2	C15—C10—C9	118.22 (10)
C2—C3—C4	119.79 (12)	C11—C10—C9	123.29 (11)
C2—C3—H3A	120.1	C12—C11—C10	120.83 (11)
C4—C3—H3A	120.1	C12—C11—H11A	119.6
C5—C4—C3	120.04 (12)	C10—C11—H11A	119.6
C5—C4—H4A	120.0	C11—C12—C13	119.13 (11)
C3—C4—H4A	120.0	C11—C12—H12A	120.4
C4—C5—C6	121.64 (12)	C13—C12—H12A	120.4
C4—C5—H5A	119.2	C14—C13—C12	121.40 (12)
C6—C5—H5A	119.2	C14—C13—Cl2	119.73 (10)
C1—C6—C5	116.74 (11)	C12—C13—Cl2	118.85 (10)
C1—C6—C7	121.68 (10)	C15—C14—C13	118.81 (11)
C5—C6—C7	121.57 (11)	C15—C14—H14A	120.6
C8—C7—C6	126.75 (11)	C13—C14—H14A	120.6
C8—C7—H7A	116.6	C14—C15—C10	121.36 (11)
C6—C7—H7A	116.6	C14—C15—H15A	119.3
C7—C8—C9	120.19 (11)	C10—C15—H15A	119.3
C7—C8—H8A	119.9

C6—C1—C2—C3	0.0 (2)	C7—C8—C9—C10	163.02 (12)
Cl1—C1—C2—C3	−177.01 (11)	O1—C9—C10—C15	1.95 (18)
C1—C2—C3—C4	0.2 (2)	C8—C9—C10—C15	−176.18 (11)
C2—C3—C4—C5	−0.3 (2)	O1—C9—C10—C11	−179.57 (13)
C3—C4—C5—C6	0.2 (2)	C8—C9—C10—C11	2.31 (18)
C2—C1—C6—C5	−0.06 (18)	C15—C10—C11—C12	0.40 (19)
Cl1—C1—C6—C5	176.87 (10)	C9—C10—C11—C12	−178.08 (12)
C2—C1—C6—C7	178.80 (12)	C10—C11—C12—C13	−0.4 (2)
Cl1—C1—C6—C7	−4.27 (16)	C11—C12—C13—C14	0.09 (19)
C4—C5—C6—C1	−0.02 (19)	C11—C12—C13—Cl2	178.74 (10)
C4—C5—C6—C7	−178.88 (12)	C12—C13—C14—C15	0.16 (19)
C1—C6—C7—C8	164.24 (13)	Cl2—C13—C14—C15	−178.48 (10)
C5—C6—C7—C8	−17.0 (2)	C13—C14—C15—C10	−0.13 (19)
C6—C7—C8—C9	−179.71 (12)	C11—C10—C15—C14	−0.15 (19)
C7—C8—C9—O1	−15.08 (19)	C9—C10—C15—C14	178.41 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cl1	0.93	2.65	3.0484 (12)	107
C7—H7A···O1	0.93	2.46	2.7973 (15)	101
C15—H15A···O1	0.93	2.46	2.7691 (15)	100
C12—H12A···O1ⁱ	0.93	2.59	3.2064 (16)	125

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀Cl₂O
M_r	277.13
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	7.2777 (1), 11.2686 (2), 30.2365 (6)
V (Å³)	2479.68 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.51
Crystal size (mm)	0.51 × 0.34 × 0.19

Data collection
Diffractometer	Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.781, 0.911
No. of measured, independent and observed [I > 2σ(I)] reflections	42713, 5996, 4413
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.834

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.127, 1.05
No. of reflections	5996
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.21

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
C7—H7A···Cl1	0.93	2.65	3.0484 (12)	107
C7—H7A···O1	0.93	2.46	2.7973 (15)	101
C15—H15A···O1	0.93	2.46	2.7691 (15)	100
C12—H12A···O1ⁱ	0.93	2.59	3.2064 (16)	125

Symmetry code: (i) −x+2, 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. HKF and IAR also thank the Malaysian Government and Universiti Sains Malaysia for FRGS grant No. 203/PFIZIK/671064. SRJ thanks the Universiti Sains Malaysia for a post-doctoral research fellowship. This work was supported by the Department of Science and Technology (DST), Government of India (grant No. SR/S2/LOP-17/2006).

References

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