(E)-3-(4-Chloro­phen­yl)-1-(2,4-dichloro-5-fluoro­phen­yl)prop-2-en-1-one

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

doi:10.1107/S1600536808012178

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages o956-o957

doi:10.1107/S1600536808012178

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(E)-3-(4-Chlorophenyl)-1-(2,4-dichloro-5-fluorophenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^* Suchada Chantrapromma,^b ‡ P. S. Patil,^c M. S. Karthikeyan ^d 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, ^cDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and ^dSyngene International Pvt Limited Plot No. 2 & 3 C, Unit-II Bommansandra Industrial Area, Bangalore 99, India
^*Correspondence e-mail: hkfun@usm.my

(Received 23 April 2008; accepted 27 April 2008; online 3 May 2008)

In the title chalcone derivative, C₁₅H₈Cl₃FO, the dihedral angle between the two benzene rings is 43.35 (8)°. Weak C—H⋯O and C—H⋯Cl intramolecular interactions involving the enone group generate S(5) and S(6) ring motifs, respectively. In the crystal structure, molecules are linked into antiparallel chains along the a axis. These chains are stacked along the b axis and short Cl⋯F contacts of 3.100 (1) Å link adjacent molecules of the antiparallel chains into dimers.

Related literature

For hydrogen bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For related structures, see, for example: Fun et al. (2007 ); Patil et al. (2007a ,b). For background to the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999 ); Patil et al. (2006 ); Shivarama Holla et al. (2004 ). For related literature, see: Gu et al. (2008 ).

Experimental

Crystal data

C₁₅H₈Cl₃FO
M_r = 329.56
Monoclinic, P 2₁ /c
a = 6.8271 (1) Å
b = 3.7832 (1) Å
c = 52.0206 (10) Å
β = 96.100 (1)°
V = 1336.00 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.69 mm⁻¹
T = 100.0 (1) K
0.35 × 0.29 × 0.18 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.794, T_max = 0.889
42462 measured reflections
5852 independent reflections
5257 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.113
S = 1.28
5852 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cl2	0.93	2.81	3.1164 (16)	101
C9—H9⋯O1	0.93	2.57	2.878 (2)	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/S1600536808012178/sj2488sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012178/sj2488Isup2.hkl

checkCIF report

Comment top

In recent years extensive research has been carried out on organic nonlinear optical materials particularly chalcone derivatives due to their high nonlinearity, varied synthesis, and better laser damage resistance as compared to their inorganic counterparts (Agrinskaya et al., 1999; Shivarama Holla et al., 2004; Patil et al., 2006). In view of the importance of these organic materials, the title compound (I) was synthesized and its crystal structure is reported here.

The total molecular structure of the title compound (Fig. 1) is not planar, the dihedral angles between the two benzene rings is 43.35 (8)°. Atoms O1, C6, C7 and C8 lie on a plane and the least-squares plane through this moiety makes dihedral angles of 47.45 (10)° and 4.16 (10)° with the C1–C6 and C10–C15 benzene rings, repectively. The orientation of the prop-2-en-1-one unit can be indicated by the torsion angles C7–C8–C9–C10 = 177.37 (16)° and O1–C7–C8–C9 = 7.5 (3)°. Bond lengths and angles in (I) are in normal ranges (Allen et al., 1987) and comparable to those in related structures (Fun et al., 2007; Patil et al., 2007a; 2007b).

In the structure, weak C9—H9···O1 and C8—H8···Cl2 intramolecular interactions generate S(5) and S(6) ring motifs (Bernstein et al., 1995) (Table 1). In the crystal structure (Fig. 2), the molecules are linked into anti-parallel chains along the a axis. These chains are stacked along the b-axis and short Cl···F contacts of 3.100 (1) Å link adjacent molecules of the anti-parallel chains into dimers. The crystal is also stabilized by weak C—H···O and C—H···Cl intramolecular interactions (Table 1).

Related literature top

For hydrogen bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For related structures, see, for example: Fun et al. (2007); Patil et al. (2007a,b,c. For background to the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999); Patil et al. (2006); Shivarama Holla et al. (2004). For related literature, see: Gu et al. (2008).

Experimental top

The title compound was synthesized by the condensation of 4-chlorobenzaldehyde (0.01 mol) with 2,4-dichloro-5-fluoroacetophenone (0.01 mol) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (10 ml, 10%). After stirring for 8 hr, the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 5 hr. 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.

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 b axis showing stacking of anti-parallel chains of molecules approximately along the b axis. Cl···F short contacts and weak C—H···O and C—H···Cl interactions are drawn as dashed lines.

(E)-3-(4-Chlorophenyl)-1-(2,4-dichloro-5-fluorophenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₈Cl₃FO	F(000) = 664
M_r = 329.56	D_x = 1.638 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5852 reflections
a = 6.8271 (1) Å	θ = 0.8–35.0°
b = 3.7832 (1) Å	µ = 0.69 mm⁻¹
c = 52.0206 (10) Å	T = 100 K
β = 96.100 (1)°	Block, colorless
V = 1336.00 (5) Å³	0.35 × 0.29 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	5852 independent reflections
Radiation source: fine-focus sealed tube	5257 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 8.33 pixels mm^-1	θ_max = 35.0°, θ_min = 0.8°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→6
T_min = 0.794, T_max = 0.889	l = −83→72
42462 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.29	w = 1/[σ²(F_o²) + (0.0246P)² + 1.777P] where P = (F_o² + 2F_c²)/3
5852 reflections	(Δ/σ)_max = 0.001
181 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₅H₈Cl₃FO	V = 1336.00 (5) Å³
M_r = 329.56	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.8271 (1) Å	µ = 0.69 mm⁻¹
b = 3.7832 (1) Å	T = 100 K
c = 52.0206 (10) Å	0.35 × 0.29 × 0.18 mm
β = 96.100 (1)°

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	5852 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5257 reflections with I > 2σ(I)
T_min = 0.794, T_max = 0.889	R_int = 0.036
42462 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.29	Δρ_max = 0.47 e Å⁻³
5852 reflections	Δρ_min = −0.31 e Å⁻³
181 parameters

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	0.75834 (7)	0.29526 (14)	0.494133 (8)	0.02272 (10)
Cl2	0.27758 (6)	−0.21297 (12)	0.414214 (9)	0.01926 (9)
Cl3	−0.33602 (6)	0.43796 (13)	0.273464 (9)	0.02136 (9)
F1	1.03386 (16)	0.3790 (4)	0.45548 (2)	0.0240 (2)
O1	0.75361 (19)	−0.1864 (4)	0.37069 (3)	0.0211 (3)
C1	0.8267 (2)	0.1756 (5)	0.41951 (3)	0.0159 (3)
H1	0.9260	0.2170	0.4090	0.019*
C2	0.8591 (2)	0.2477 (5)	0.44562 (3)	0.0164 (3)
C3	0.7139 (3)	0.1882 (5)	0.46193 (3)	0.0163 (3)
C4	0.5343 (2)	0.0489 (5)	0.45181 (3)	0.0169 (3)
H4	0.4363	0.0044	0.4625	0.020*
C5	0.5022 (2)	−0.0237 (4)	0.42545 (3)	0.0147 (3)
C6	0.6458 (2)	0.0408 (4)	0.40887 (3)	0.0144 (3)
C7	0.6216 (2)	−0.0317 (5)	0.38025 (3)	0.0153 (3)
C8	0.4414 (2)	0.0999 (5)	0.36537 (3)	0.0163 (3)
H8	0.3552	0.2390	0.3737	0.020*
C9	0.3966 (2)	0.0265 (5)	0.34022 (3)	0.0160 (3)
H9	0.4878	−0.1048	0.3322	0.019*
C10	0.2173 (2)	0.1348 (4)	0.32437 (3)	0.0142 (3)
C11	0.1999 (2)	0.0697 (5)	0.29770 (3)	0.0160 (3)
H11	0.3036	−0.0370	0.2904	0.019*
C12	0.0306 (3)	0.1616 (5)	0.28197 (3)	0.0163 (3)
H12	0.0205	0.1187	0.2643	0.020*
C13	−0.1239 (2)	0.3191 (5)	0.29314 (3)	0.0161 (3)
C14	−0.1123 (2)	0.3856 (5)	0.31941 (3)	0.0166 (3)
H14	−0.2171	0.4903	0.3266	0.020*
C15	0.0583 (2)	0.2938 (5)	0.33493 (3)	0.0167 (3)
H15	0.0672	0.3383	0.3526	0.020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0267 (2)	0.0276 (2)	0.01395 (17)	−0.00233 (17)	0.00251 (14)	−0.00137 (16)
Cl2	0.01366 (16)	0.02036 (19)	0.02387 (19)	−0.00204 (14)	0.00256 (13)	−0.00089 (15)
Cl3	0.01787 (17)	0.0229 (2)	0.0221 (2)	0.00123 (15)	−0.00347 (14)	0.00159 (16)
F1	0.0177 (5)	0.0353 (7)	0.0186 (5)	−0.0072 (5)	0.0003 (4)	−0.0023 (5)
O1	0.0187 (6)	0.0267 (7)	0.0183 (6)	0.0044 (5)	0.0036 (4)	−0.0029 (5)
C1	0.0135 (6)	0.0179 (7)	0.0163 (7)	0.0005 (5)	0.0023 (5)	0.0005 (6)
C2	0.0139 (6)	0.0184 (7)	0.0167 (7)	−0.0008 (5)	0.0008 (5)	0.0006 (6)
C3	0.0187 (7)	0.0173 (7)	0.0132 (6)	0.0012 (6)	0.0027 (5)	0.0010 (6)
C4	0.0160 (7)	0.0190 (7)	0.0163 (7)	0.0008 (6)	0.0046 (5)	0.0022 (6)
C5	0.0123 (6)	0.0139 (7)	0.0178 (7)	0.0008 (5)	0.0015 (5)	0.0007 (5)
C6	0.0139 (6)	0.0142 (7)	0.0149 (7)	0.0022 (5)	0.0013 (5)	0.0012 (5)
C7	0.0160 (6)	0.0151 (7)	0.0148 (7)	0.0002 (5)	0.0015 (5)	−0.0004 (5)
C8	0.0160 (7)	0.0159 (7)	0.0167 (7)	0.0022 (6)	0.0006 (5)	−0.0008 (6)
C9	0.0156 (6)	0.0156 (7)	0.0166 (7)	−0.0001 (5)	0.0014 (5)	0.0001 (6)
C10	0.0152 (6)	0.0126 (6)	0.0148 (6)	−0.0005 (5)	0.0017 (5)	−0.0001 (5)
C11	0.0177 (7)	0.0158 (7)	0.0148 (7)	0.0004 (6)	0.0036 (5)	−0.0008 (6)
C12	0.0201 (7)	0.0145 (7)	0.0141 (7)	0.0005 (6)	0.0010 (5)	0.0001 (5)
C13	0.0156 (6)	0.0154 (7)	0.0166 (7)	−0.0013 (6)	−0.0009 (5)	0.0016 (6)
C14	0.0157 (6)	0.0168 (7)	0.0175 (7)	0.0017 (6)	0.0028 (5)	−0.0003 (6)
C15	0.0169 (7)	0.0190 (7)	0.0143 (6)	0.0007 (6)	0.0023 (5)	−0.0006 (6)

Geometric parameters (Å, º) top

Cl1—C3	1.7190 (17)	C8—C9	1.341 (2)
Cl2—C5	1.7366 (17)	C8—H8	0.9300
Cl3—C13	1.7412 (17)	C9—C10	1.460 (2)
F1—C2	1.343 (2)	C9—H9	0.9300
O1—C7	1.224 (2)	C10—C11	1.402 (2)
C1—C2	1.380 (2)	C10—C15	1.403 (2)
C1—C6	1.395 (2)	C11—C12	1.388 (2)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.390 (2)	C12—C13	1.391 (2)
C3—C4	1.386 (2)	C12—H12	0.9300
C4—C5	1.392 (2)	C13—C14	1.383 (2)
C4—H4	0.9300	C14—C15	1.389 (2)
C5—C6	1.394 (2)	C14—H14	0.9300
C6—C7	1.505 (2)	C15—H15	0.9300
C7—C8	1.469 (2)

C2—C1—C6	120.37 (15)	C7—C8—H8	118.8
C2—C1—H1	119.8	C8—C9—C10	125.68 (16)
C6—C1—H1	119.8	C8—C9—H9	117.2
F1—C2—C1	119.49 (15)	C10—C9—H9	117.2
F1—C2—C3	119.28 (15)	C11—C10—C15	118.36 (15)
C1—C2—C3	121.23 (16)	C11—C10—C9	119.16 (15)
C4—C3—C2	119.29 (15)	C15—C10—C9	122.45 (15)
C4—C3—Cl1	121.14 (13)	C12—C11—C10	121.15 (16)
C2—C3—Cl1	119.55 (13)	C12—C11—H11	119.4
C3—C4—C5	119.29 (15)	C10—C11—H11	119.4
C3—C4—H4	120.4	C11—C12—C13	118.82 (15)
C5—C4—H4	120.4	C11—C12—H12	120.6
C4—C5—C6	121.82 (15)	C13—C12—H12	120.6
C4—C5—Cl2	116.97 (13)	C14—C13—C12	121.60 (15)
C6—C5—Cl2	121.17 (13)	C14—C13—Cl3	119.38 (13)
C5—C6—C1	117.98 (15)	C12—C13—Cl3	119.02 (13)
C5—C6—C7	124.71 (15)	C13—C14—C15	119.06 (16)
C1—C6—C7	117.29 (15)	C13—C14—H14	120.5
O1—C7—C8	124.03 (16)	C15—C14—H14	120.5
O1—C7—C6	118.75 (15)	C14—C15—C10	121.01 (16)
C8—C7—C6	117.19 (14)	C14—C15—H15	119.5
C9—C8—C7	122.36 (16)	C10—C15—H15	119.5
C9—C8—H8	118.8

C6—C1—C2—F1	−179.66 (16)	C5—C6—C7—C8	49.0 (2)
C6—C1—C2—C3	0.1 (3)	C1—C6—C7—C8	−132.33 (17)
F1—C2—C3—C4	−179.28 (16)	O1—C7—C8—C9	7.5 (3)
C1—C2—C3—C4	0.9 (3)	C6—C7—C8—C9	−174.50 (16)
F1—C2—C3—Cl1	1.8 (2)	C7—C8—C9—C10	177.37 (16)
C1—C2—C3—Cl1	−177.94 (14)	C8—C9—C10—C11	173.51 (18)
C2—C3—C4—C5	−0.9 (3)	C8—C9—C10—C15	−8.3 (3)
Cl1—C3—C4—C5	177.97 (14)	C15—C10—C11—C12	0.4 (3)
C3—C4—C5—C6	−0.2 (3)	C9—C10—C11—C12	178.70 (16)
C3—C4—C5—Cl2	177.69 (14)	C10—C11—C12—C13	−0.4 (3)
C4—C5—C6—C1	1.2 (3)	C11—C12—C13—C14	0.0 (3)
Cl2—C5—C6—C1	−176.57 (13)	C11—C12—C13—Cl3	179.54 (14)
C4—C5—C6—C7	179.86 (16)	C12—C13—C14—C15	0.2 (3)
Cl2—C5—C6—C7	2.1 (2)	Cl3—C13—C14—C15	−179.27 (14)
C2—C1—C6—C5	−1.2 (3)	C13—C14—C15—C10	−0.2 (3)
C2—C1—C6—C7	−179.91 (16)	C11—C10—C15—C14	−0.2 (3)
C5—C6—C7—O1	−132.87 (19)	C9—C10—C15—C14	−178.37 (17)
C1—C6—C7—O1	45.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cl2	0.93	2.81	3.1164 (16)	101
C9—H9···O1	0.93	2.57	2.878 (2)	100

Experimental details

Crystal data
Chemical formula	C₁₅H₈Cl₃FO
M_r	329.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	6.8271 (1), 3.7832 (1), 52.0206 (10)
β (°)	96.100 (1)
V (Å³)	1336.00 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.35 × 0.29 × 0.18

Data collection
Diffractometer	Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.794, 0.889
No. of measured, independent and observed [I > 2σ(I)] reflections	42462, 5852, 5257
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.113, 1.29
No. of reflections	5852
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.31

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
C8—H8···Cl2	0.93	2.81	3.1164 (16)	101
C9—H9···O1	0.93	2.57	2.878 (2)	100

Footnotes

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

Acknowledgements

This work is supported by 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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