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

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

doi:10.1107/S160053680801413X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1086

doi:10.1107/S160053680801413X

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

Hoong-Kun Fun,^a ^* Suchada Chantrapromma,^b ‡ P. S. Patil ^c and S. M. Dharmaprakash ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 6 May 2008; accepted 12 May 2008; online 17 May 2008)

In the title chalcone derivative, C₁₅H₉Cl₃O, the dihedral angle between the 2-chlorophenyl and 2,4-dichlorophenyl rings is 41.79 (14)°. Weak C—H⋯O and C—H⋯Cl intramolecular interactions involving the enone unit generate S(5) ring motifs. In the crystal structure, the molecules are arranged in a head-to-tail manner along the a axis. These chains are stacked along the b axis.

Related literature

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For related structures, see, for example: Fun, Chantrapromma et al. (2007 ); Fun, Patil et al. (2007 ); Patil, Chantrapromma et al. (2007 ; Patil, Fun et al. (2007 ). For background to the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999 ); Gu et al. (2008 ); Patil, Dharmaprakash et al. (2007 ).

Experimental

Crystal data

C₁₅H₉Cl₃O
M_r = 311.57
Monoclinic, C 2/c
a = 50.177 (2) Å
b = 3.8082 (2) Å
c = 13.7297 (7) Å
β = 95.307 (3)°
V = 2612.3 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.69 mm⁻¹
T = 100.0 (1) K
0.39 × 0.20 × 0.14 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.775, T_max = 0.910
13605 measured reflections
2976 independent reflections
2374 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.189
S = 1.13
2976 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯Cl3	0.93	2.66	3.042 (5)	106
C9—H9A⋯O1	0.93	2.53	2.841 (6)	100

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/S160053680801413X/is2291sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801413X/is2291Isup2.hkl

checkCIF report

Comment top

Nonlinear optical properties of chalcone derivatives have been widely investigated recently (Agrinskaya et al., 1999; Fun, Chantrapromma et al., 2007; Fun, Patil et al., 2007; Patil, Dharmaprakash et al., 2007; Patil, Chantrapromma et al., 2007; Patil, Fun et al., 2007). These molecules show potential in optical-limiting applications due to their large excited-state absorption cross sections (Gu et al., 2008). In view of the importance of chalcones and the continuation of our non-linear optic materials research the title chalcone derivative, (I), was synthesized and its crystal structure is reported here.

In the structure of the title chalcone derivative (Fig. 1), the enone unit O1/C6–C8, the 2-chlorophenyl and 2,4-dichlorophenyl rings are individually planar, with the maximum deviations of 0.016 (6), -0.017 (6) and 0.022 (5) Å for atom C7, C11 and C2, respectively. The molecule is slightly twisted about the C6–C7 bond as indicated by the torsion angles C1–C6–C7–C8 = 132.8 (5)°, C6–C7–C8–C9 = 171.6 (5)°, C7–C8–C9–C10 = -179.7 (5)° and C8–C9–C10–C15 = -160.7 (5)°. The dihedral angles between the 2-chlorophenyl and 2,4-dichlorophenyl rings is 41.79 (14)°. The least-squares plane through the enone unit makes dihedral angles of 10.3 (3)° and 46.9 (2)° with the 2-chlorophenyl and 2,4-dichlorophenyl rings, respectively. The orientation of the prop-2-en-1-one unit can be indicated by the torsion angle O1–C7–C8–C9 = -11.5 (8)°. Bond lengths and angles in (I) are in normal ranges (Allen et al., 1987) and comparable to those in related structures (Fun, Chantrapromma et al., 2007; Fun, Patil et al., 2007; Patil, Dharmaprakash et al., 2007; Patil, Chantrapromma et al., 2007; Patil, Fun et al., 2007).

In the molecular structure, both weak C9—H9A···O1 and C9—H9A···Cl1 intramolecular interactions (Table 1) generate S(5) ring motifs (Bernstein et al., 1995). In the crystal structure (Fig. 2), the molecules are arranged in a head-to-tail manner along the a-axis. These chains are stacked along the b axis.

Related literature top

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For related structures, see, for example: Fun, Chantrapromma et al. (2007); Fun, Patil et al. (2007); Patil, Chantrapromma et al. (2007; Patil, Fun et al. (2007). For background to the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999); Gu et al. (2008); Patil, Dharmaprakash et al. (2007).

Experimental top

The title compound was synthesized by the condensation of 2-chlorobenzaldehyde (0.01 mol) with 2,4-dichloroacetophenones (0.01 mol) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring (4 h), the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 6 h. The resulting crude solid was filtered and dried. Colorless block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from acetone by slow evaporation of the solvent 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 asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering. Weak intramolecular C—H···O and C—H···Cl interactions are drawn as dashed lines.
	Fig. 2. The crystal packing of (I), viewed along the c axis showing head-to-tail arrangement along the a axis and stacking of the molecules along the b axis.

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

Crystal data top

C₁₅H₉Cl₃O	F(000) = 1264
M_r = 311.57	D_x = 1.584 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2976 reflections
a = 50.177 (2) Å	θ = 0.8–27.5°
b = 3.8082 (2) Å	µ = 0.69 mm⁻¹
c = 13.7297 (7) Å	T = 100 K
β = 95.307 (3)°	Block, colorless
V = 2612.3 (2) Å³	0.39 × 0.20 × 0.14 mm
Z = 8

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	2976 independent reflections
Radiation source: fine-focus sealed tube	2374 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 8.33 pixels mm^-1	θ_max = 27.5°, θ_min = 0.8°
ω scans	h = −64→64
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −4→4
T_min = 0.775, T_max = 0.911	l = −17→17
13605 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.189	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0626P)² + 28.0963P] where P = (F_o² + 2F_c²)/3
2976 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

C₁₅H₉Cl₃O	V = 2612.3 (2) Å³
M_r = 311.57	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 50.177 (2) Å	µ = 0.69 mm⁻¹
b = 3.8082 (2) Å	T = 100 K
c = 13.7297 (7) Å	0.39 × 0.20 × 0.14 mm
β = 95.307 (3)°

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	2976 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2374 reflections with I > 2σ(I)
T_min = 0.775, T_max = 0.911	R_int = 0.054
13605 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.189	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0626P)² + 28.0963P] where P = (F_o² + 2F_c²)/3
2976 reflections	Δρ_max = 0.52 e Å⁻³
172 parameters	Δρ_min = −0.58 e Å⁻³

Special details top

Experimental. The low-temperature 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	0.24912 (2)	0.3582 (3)	0.13634 (9)	0.0253 (3)
Cl2	0.32818 (2)	0.9466 (3)	−0.04254 (9)	0.0272 (3)
Cl3	0.46557 (2)	0.9477 (4)	0.12885 (9)	0.0320 (3)
O1	0.37362 (7)	0.9696 (11)	0.2294 (3)	0.0353 (9)
C1	0.32520 (9)	0.5622 (13)	0.2282 (4)	0.0240 (10)
H1A	0.3364	0.5366	0.2855	0.029*
C2	0.29887 (9)	0.4535 (13)	0.2272 (4)	0.0247 (10)
H2A	0.2924	0.3562	0.2825	0.030*
C3	0.28239 (8)	0.4941 (13)	0.1413 (4)	0.0232 (10)
C4	0.29124 (9)	0.6481 (12)	0.0592 (3)	0.0225 (10)
H4A	0.2797	0.6825	0.0030	0.027*
C5	0.31790 (9)	0.7503 (13)	0.0626 (4)	0.0237 (10)
C6	0.33539 (9)	0.7072 (13)	0.1473 (3)	0.0226 (10)
C7	0.36458 (9)	0.8125 (15)	0.1559 (4)	0.0292 (11)
C8	0.38100 (10)	0.7060 (15)	0.0778 (4)	0.0312 (11)
H8A	0.3740	0.5518	0.0295	0.037*
C9	0.40609 (9)	0.8285 (15)	0.0751 (4)	0.0310 (11)
H9A	0.4126	0.9814	0.1245	0.037*
C10	0.42374 (10)	0.7390 (14)	0.0006 (4)	0.0298 (11)
C11	0.41423 (10)	0.6012 (15)	−0.0914 (4)	0.0346 (12)
H11A	0.3960	0.5603	−0.1046	0.042*
C12	0.43090 (11)	0.5256 (15)	−0.1619 (4)	0.0357 (12)
H12A	0.4239	0.4393	−0.2224	0.043*
C13	0.45816 (11)	0.5780 (15)	−0.1430 (4)	0.0357 (12)
H13A	0.4695	0.5252	−0.1907	0.043*
C14	0.46862 (9)	0.7084 (14)	−0.0535 (4)	0.0298 (11)
H14A	0.4870	0.7433	−0.0406	0.036*
C15	0.45143 (9)	0.7860 (13)	0.0163 (4)	0.0263 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0192 (5)	0.0235 (6)	0.0333 (6)	−0.0020 (4)	0.0024 (4)	0.0004 (5)
Cl2	0.0291 (6)	0.0242 (6)	0.0288 (6)	−0.0030 (5)	0.0058 (4)	0.0011 (5)
Cl3	0.0250 (6)	0.0343 (7)	0.0363 (7)	−0.0035 (5)	0.0016 (5)	0.0009 (6)
O1	0.0274 (17)	0.042 (2)	0.036 (2)	−0.0053 (16)	−0.0011 (14)	−0.0058 (18)
C1	0.024 (2)	0.021 (2)	0.027 (2)	0.0057 (18)	−0.0006 (17)	−0.004 (2)
C2	0.024 (2)	0.019 (2)	0.032 (3)	0.0036 (18)	0.0049 (18)	0.000 (2)
C3	0.0156 (19)	0.024 (2)	0.031 (2)	−0.0004 (17)	0.0051 (17)	−0.004 (2)
C4	0.024 (2)	0.017 (2)	0.025 (2)	0.0020 (17)	−0.0019 (17)	−0.0009 (19)
C5	0.025 (2)	0.018 (2)	0.028 (2)	0.0008 (18)	0.0052 (18)	0.000 (2)
C6	0.021 (2)	0.021 (2)	0.026 (2)	0.0021 (18)	0.0032 (17)	0.000 (2)
C7	0.026 (2)	0.032 (3)	0.029 (3)	−0.001 (2)	0.0028 (19)	0.002 (2)
C8	0.026 (2)	0.032 (3)	0.035 (3)	0.001 (2)	0.001 (2)	0.000 (2)
C9	0.027 (2)	0.033 (3)	0.033 (3)	0.001 (2)	0.002 (2)	0.002 (2)
C10	0.027 (2)	0.028 (3)	0.035 (3)	−0.001 (2)	0.004 (2)	0.008 (2)
C11	0.032 (3)	0.031 (3)	0.041 (3)	−0.005 (2)	0.000 (2)	0.006 (2)
C12	0.042 (3)	0.026 (3)	0.038 (3)	0.000 (2)	−0.003 (2)	−0.001 (2)
C13	0.034 (3)	0.031 (3)	0.043 (3)	0.006 (2)	0.007 (2)	−0.002 (3)
C14	0.022 (2)	0.028 (3)	0.040 (3)	0.002 (2)	0.0045 (19)	0.002 (2)
C15	0.025 (2)	0.019 (2)	0.035 (3)	−0.0010 (19)	0.0021 (19)	0.006 (2)

Geometric parameters (Å, º) top

Cl1—C3	1.743 (4)	C8—C9	1.347 (7)
Cl2—C5	1.746 (5)	C8—H8A	0.9300
Cl3—C15	1.751 (5)	C9—C10	1.454 (7)
O1—C7	1.224 (6)	C9—H9A	0.9300
C1—C6	1.380 (7)	C10—C15	1.398 (6)
C1—C2	1.383 (6)	C10—C11	1.410 (8)
C1—H1A	0.9300	C11—C12	1.367 (8)
C2—C3	1.385 (7)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.383 (7)
C3—C4	1.380 (7)	C12—H12A	0.9300
C4—C5	1.390 (6)	C13—C14	1.382 (8)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.400 (6)	C14—C15	1.380 (7)
C6—C7	1.512 (6)	C14—H14A	0.9300
C7—C8	1.468 (7)

C6—C1—C2	122.4 (4)	C7—C8—H8A	119.6
C6—C1—H1A	118.8	C8—C9—C10	124.7 (5)
C2—C1—H1A	118.8	C8—C9—H9A	117.6
C1—C2—C3	118.0 (4)	C10—C9—H9A	117.6
C1—C2—H2A	121.0	C15—C10—C11	115.8 (5)
C3—C2—H2A	121.0	C15—C10—C9	121.5 (5)
C4—C3—C2	122.1 (4)	C11—C10—C9	122.7 (5)
C4—C3—Cl1	118.3 (4)	C12—C11—C10	122.3 (5)
C2—C3—Cl1	119.6 (4)	C12—C11—H11A	118.8
C3—C4—C5	118.2 (4)	C10—C11—H11A	118.8
C3—C4—H4A	120.9	C11—C12—C13	119.7 (5)
C5—C4—H4A	120.9	C11—C12—H12A	120.2
C4—C5—C6	121.5 (4)	C13—C12—H12A	120.2
C4—C5—Cl2	116.7 (4)	C14—C13—C12	120.5 (5)
C6—C5—Cl2	121.8 (3)	C14—C13—H13A	119.8
C1—C6—C5	117.7 (4)	C12—C13—H13A	119.8
C1—C6—C7	118.2 (4)	C15—C14—C13	118.9 (5)
C5—C6—C7	124.1 (4)	C15—C14—H14A	120.5
O1—C7—C8	123.2 (4)	C13—C14—H14A	120.5
O1—C7—C6	118.4 (4)	C14—C15—C10	122.8 (5)
C8—C7—C6	118.4 (4)	C14—C15—Cl3	117.4 (4)
C9—C8—C7	120.9 (5)	C10—C15—Cl3	119.8 (4)
C9—C8—H8A	119.6

C6—C1—C2—C3	−0.1 (7)	O1—C7—C8—C9	−11.5 (8)
C1—C2—C3—C4	−2.1 (7)	C6—C7—C8—C9	171.6 (5)
C1—C2—C3—Cl1	179.6 (4)	C7—C8—C9—C10	−179.7 (5)
C2—C3—C4—C5	2.9 (7)	C8—C9—C10—C15	−160.7 (5)
Cl1—C3—C4—C5	−178.8 (4)	C8—C9—C10—C11	19.5 (9)
C3—C4—C5—C6	−1.4 (7)	C15—C10—C11—C12	−1.5 (8)
C3—C4—C5—Cl2	−179.6 (4)	C9—C10—C11—C12	178.4 (5)
C2—C1—C6—C5	1.4 (7)	C10—C11—C12—C13	1.3 (9)
C2—C1—C6—C7	−179.1 (5)	C11—C12—C13—C14	−0.4 (9)
C4—C5—C6—C1	−0.6 (7)	C12—C13—C14—C15	−0.1 (8)
Cl2—C5—C6—C1	177.4 (4)	C13—C14—C15—C10	−0.1 (8)
C4—C5—C6—C7	180.0 (5)	C13—C14—C15—Cl3	179.6 (4)
Cl2—C5—C6—C7	−2.0 (7)	C11—C10—C15—C14	0.9 (8)
C1—C6—C7—O1	−44.2 (7)	C9—C10—C15—C14	−179.0 (5)
C5—C6—C7—O1	135.2 (5)	C11—C10—C15—Cl3	−178.8 (4)
C1—C6—C7—C8	132.8 (5)	C9—C10—C15—Cl3	1.3 (7)
C5—C6—C7—C8	−47.8 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···Cl3	0.93	2.66	3.042 (5)	106
C9—H9A···O1	0.93	2.53	2.841 (6)	100

Experimental details

Crystal data
Chemical formula	C₁₅H₉Cl₃O
M_r	311.57
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	50.177 (2), 3.8082 (2), 13.7297 (7)
β (°)	95.307 (3)
V (Å³)	2612.3 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.39 × 0.20 × 0.14

Data collection
Diffractometer	Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.775, 0.911
No. of measured, independent and observed [I > 2σ(I)] reflections	13605, 2976, 2374
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.189, 1.13
No. of reflections	2976
No. of parameters	172
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0626P)² + 28.0963P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.58

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
C9—H9A···Cl3	0.93	2.66	3.042 (5)	106
C9—H9A···O1	0.93	2.53	2.841 (6)	100

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

This work is supported by the Department of Science and Technology (DST), Government of India, under grant No. SR/S2/LOP-17/2006. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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