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

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

doi:10.1107/S1600536808020795

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1464

doi:10.1107/S1600536808020795

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

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

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

(Received 3 July 2008; accepted 4 July 2008; online 12 July 2008)

The structure of the title compound, C₁₅H₁₀BrClO, comprises two substituted benzene rings bridged by a prop-2-en-1-one group and exists in an E configuration about the C=N double bond. The dihedral angle formed between the 4-bromophenyl and 2-chlorophenyl rings is 23.77 (18)°. In the crystal structure, the molecules are linked by weak C—H⋯O interactions, forming a supramolecular zigzag chain. Intramolecular C—H⋯Cl and C—H⋯O hydrogen bonds are also present.

Related literature

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Patil et al. (2007 ); Moorthi et al. (2005 ). For applications of chalcones, see: Gu et al. (2008 ); Mishra et al. (2008 ); Nel et al. (1998 ); Patil & Dharmaprakash (2008 ); Wang et al. (2004 ).

Experimental

Crystal data

C₁₅H₁₀BrClO
M_r = 321.59
Orthorhombic, P n a 2₁
a = 27.8720 (6) Å
b = 3.9235 (1) Å
c = 11.6408 (2) Å
V = 1272.99 (5) Å³
Z = 4
Mo Kα radiation
μ = 3.42 mm⁻¹
T = 100.0 (1) K
0.33 × 0.18 × 0.09 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.392, T_max = 0.736
9658 measured reflections
3495 independent reflections
2938 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.086
S = 1.03
3495 reflections
163 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.44 e Å⁻³
Absolute structure: Flack (1983 ), 1545 Friedel pairs
Flack parameter: 0.011 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1ⁱ	0.93	2.53	3.191 (4)	128
C9—H9A⋯Cl1	0.93	2.61	3.064 (4)	111
C9—H9A⋯O1	0.93	2.41	2.765 (5)	102
Symmetry code: (i) $[-x, -y, z-{\script{1\over 2}}]$ .

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/S1600536808020795/tk2281sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020795/tk2281Isup2.hkl

checkCIF report

Comment top

Chalcone and its derivatives have a wide range of applications ranging from bioactivities (Mishra et al., 2008; Nel et al., 1998) to materials with non-linear optical (NLO) properties (Gu et al., 2008 & Moorthi et al., 2005). As part of our continuing interest in the latter application (Patil & Dharmaprakash, 2008), the synthesis and structure of the title compound (I, Fig. 1) is described herein.The non-centrosymmetric crystal of the title compound should exhibit 2nd-order NLO properties.

The structure of (I) comprises two six-membered rings bridged by a pro-2-en-1-one moiety. The molecule exists in the E conformation with respect to the C8=C9 double bond [1.328 (5) Å]. The molecule is not planar as seen in the dihedral angle of 23.77 (18)° formed between the 4-bromophenyl and 2-chlorophenyl rings. Further, the mean plane through the O1, C6, C7 & C8 atoms forms angles, respectively, of 13.2 (2)° and 11.0 (2)° with the planes of 4-bromophenyl and 2-chlorophenyl rings. Weak C9–H9A···O1 and C9—H9A···Cl1 intramolecular interactions (Fig. 1 & Table 1) generate S(5) ring motifs (Bernstein et al., 1995). The derived bond distances and angles are comparable with those determined in the closely related structures (e.g. Patil et al., 2007 & Sathiya Moorthi et al., 2005).

In the crystal packing (Fig. 2), the molecules are linked into a supramolecular chain via C-H···O interactions aligned along the c-direction, Table 1.

Related literature top

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Patil et al. (2007); Moorthi et al. (2005). For applications of chalcones, see: Gu et al. (2008); Mishra et al. (2008); Nel et al. (1998); Patil & Dharmaprakash (2008); Wang et al. (2004).

Experimental top

Compound (I) was synthesized by the condensation of 2-chlorobenzaldehyde (0.01 mol, 1.49 g) with 4-bromoacetophenone (0.01 mol, 1.99 g) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 20%). 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 filtered and dried. Single crystals were obtained by recrystallization from an acetone solution of (I).

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 (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. The dashed lines represent intramolecular C—H···O and C—H···Cl interactions.
	Fig. 2. A view down the b-axis of the crystal packing in (I), highlighting a supramolecular molecular chain aligned along the c axis. The C-H···O interactions are shown as dashed lines.

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

Crystal data top

C₁₅H₁₀BrClO	F(000) = 640
M_r = 321.59	D_x = 1.678 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3495 reflections
a = 27.8720 (6) Å	θ = 1.5–30.0°
b = 3.9235 (1) Å	µ = 3.42 mm⁻¹
c = 11.6408 (2) Å	T = 100 K
V = 1272.99 (5) Å³	Block, colorless
Z = 4	0.33 × 0.18 × 0.09 mm

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	3495 independent reflections
Radiation source: fine-focus sealed tube	2938 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 1.5°
ω scans	h = −36→39
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −5→3
T_min = 0.392, T_max = 0.736	l = −16→16
9658 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.086	w = 1/[σ²(F_o²) + 1.3265P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3495 reflections	Δρ_max = 0.41 e Å⁻³
163 parameters	Δρ_min = −0.44 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1545 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.011 (12)

Crystal data top

C₁₅H₁₀BrClO	V = 1272.99 (5) Å³
M_r = 321.59	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 27.8720 (6) Å	µ = 3.42 mm⁻¹
b = 3.9235 (1) Å	T = 100 K
c = 11.6408 (2) Å	0.33 × 0.18 × 0.09 mm

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	3495 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2938 reflections with I > 2σ(I)
T_min = 0.392, T_max = 0.736	R_int = 0.044
9658 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.086	Δρ_max = 0.41 e Å⁻³
S = 1.03	Δρ_min = −0.44 e Å⁻³
3495 reflections	Absolute structure: Flack (1983), 1545 Friedel pairs
163 parameters	Absolute structure parameter: 0.011 (12)
1 restraint

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
Br1	0.165695 (11)	0.71499 (8)	0.27469 (5)	0.02346 (10)
Cl1	−0.18444 (4)	−0.5643 (3)	0.47411 (9)	0.0264 (2)
O1	−0.03953 (10)	0.0955 (8)	0.5096 (2)	0.0254 (6)
C1	0.03194 (13)	0.2560 (9)	0.2561 (3)	0.0187 (8)
H1A	0.0132	0.1502	0.2004	0.022*
C2	0.07645 (13)	0.3879 (11)	0.2266 (3)	0.0192 (8)
H2A	0.0878	0.3720	0.1517	0.023*
C3	0.10349 (14)	0.5426 (9)	0.3106 (3)	0.0192 (8)
C4	0.08725 (13)	0.5741 (10)	0.4230 (3)	0.0202 (8)
H4A	0.1059	0.6831	0.4782	0.024*
C5	0.04319 (13)	0.4411 (9)	0.4510 (3)	0.0177 (8)
H5A	0.0321	0.4585	0.5261	0.021*
C6	0.01502 (13)	0.2810 (9)	0.3686 (3)	0.0156 (7)
C7	−0.03108 (13)	0.1245 (10)	0.4073 (3)	0.0180 (8)
C8	−0.06613 (13)	0.0089 (10)	0.3202 (3)	0.0185 (8)
H8A	−0.0610	0.0543	0.2428	0.022*
C9	−0.10501 (14)	−0.1603 (10)	0.3534 (3)	0.0192 (8)
H9A	−0.1074	−0.2079	0.4315	0.023*
C10	−0.14477 (11)	−0.2809 (8)	0.2809 (5)	0.0180 (6)
C11	−0.18352 (14)	−0.4627 (10)	0.3288 (3)	0.0206 (8)
C12	−0.22195 (13)	−0.5699 (9)	0.2625 (4)	0.0246 (8)
H12A	−0.2470	−0.6907	0.2960	0.030*
C13	−0.22293 (15)	−0.4970 (11)	0.1464 (4)	0.0276 (9)
H13A	−0.2488	−0.5662	0.1017	0.033*
C14	−0.18509 (15)	−0.3199 (11)	0.0968 (3)	0.0239 (8)
H14A	−0.1856	−0.2719	0.0185	0.029*
C15	−0.14652 (15)	−0.2140 (10)	0.1632 (3)	0.0213 (8)
H15A	−0.1214	−0.0963	0.1287	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01631 (16)	0.02108 (18)	0.03298 (17)	−0.00286 (13)	0.0010 (2)	0.0002 (3)
Cl1	0.0257 (5)	0.0253 (5)	0.0282 (4)	−0.0021 (4)	0.0095 (4)	0.0033 (4)
O1	0.0260 (16)	0.0329 (18)	0.0171 (13)	−0.0047 (13)	0.0038 (11)	0.0008 (11)
C1	0.0159 (16)	0.0214 (19)	0.019 (2)	−0.0002 (13)	−0.0025 (13)	0.0006 (14)
C2	0.0177 (19)	0.021 (2)	0.0187 (16)	−0.0023 (15)	−0.0003 (14)	0.0018 (15)
C3	0.0170 (18)	0.0126 (19)	0.0278 (19)	0.0004 (14)	−0.0001 (14)	0.0023 (14)
C4	0.0186 (19)	0.017 (2)	0.0248 (19)	0.0025 (15)	−0.0068 (15)	−0.0046 (15)
C5	0.0180 (18)	0.017 (2)	0.0180 (17)	0.0023 (14)	0.0011 (13)	−0.0021 (14)
C6	0.0138 (17)	0.0161 (19)	0.0169 (16)	0.0025 (14)	−0.0010 (13)	0.0003 (13)
C7	0.0176 (18)	0.015 (2)	0.0218 (17)	0.0042 (14)	−0.0011 (14)	0.0011 (14)
C8	0.0153 (18)	0.022 (2)	0.0178 (16)	−0.0010 (15)	0.0015 (14)	0.0020 (14)
C9	0.018 (2)	0.020 (2)	0.0195 (16)	0.0021 (15)	−0.0003 (14)	0.0000 (14)
C10	0.0150 (14)	0.0143 (15)	0.0248 (15)	0.0030 (12)	0.001 (2)	0.0027 (19)
C11	0.0184 (19)	0.015 (2)	0.0280 (19)	0.0060 (15)	0.0042 (15)	0.0010 (15)
C12	0.0177 (17)	0.0158 (18)	0.040 (2)	0.0019 (13)	0.0016 (18)	−0.004 (2)
C13	0.020 (2)	0.022 (2)	0.041 (2)	0.0077 (17)	−0.0090 (18)	−0.0105 (18)
C14	0.025 (2)	0.025 (2)	0.0220 (19)	0.0065 (17)	−0.0067 (16)	−0.0013 (16)
C15	0.021 (2)	0.017 (2)	0.0257 (19)	−0.0003 (15)	0.0010 (15)	0.0019 (15)

Geometric parameters (Å, º) top

Br1—C3	1.907 (4)	C8—C9	1.328 (5)
Cl1—C11	1.738 (4)	C8—H8A	0.9300
O1—C7	1.219 (4)	C9—C10	1.472 (6)
C1—C2	1.387 (5)	C9—H9A	0.9300
C1—C6	1.396 (5)	C10—C15	1.395 (7)
C1—H1A	0.9300	C10—C11	1.409 (5)
C2—C3	1.376 (5)	C11—C12	1.386 (6)
C2—H2A	0.9300	C12—C13	1.381 (7)
C3—C4	1.390 (5)	C12—H12A	0.9300
C4—C5	1.373 (5)	C13—C14	1.389 (6)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.389 (5)	C14—C15	1.388 (6)
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.493 (5)	C15—H15A	0.9300
C7—C8	1.479 (5)

C2—C1—C6	120.5 (3)	C7—C8—H8A	120.2
C2—C1—H1A	119.7	C8—C9—C10	127.4 (4)
C6—C1—H1A	119.7	C8—C9—H9A	116.3
C3—C2—C1	118.6 (3)	C10—C9—H9A	116.3
C3—C2—H2A	120.7	C15—C10—C11	117.2 (4)
C1—C2—H2A	120.7	C15—C10—C9	122.0 (3)
C2—C3—C4	122.0 (4)	C11—C10—C9	120.8 (5)
C2—C3—Br1	119.9 (3)	C12—C11—C10	121.7 (4)
C4—C3—Br1	118.1 (3)	C12—C11—Cl1	117.5 (3)
C5—C4—C3	118.7 (3)	C10—C11—Cl1	120.8 (3)
C5—C4—H4A	120.6	C13—C12—C11	119.8 (4)
C3—C4—H4A	120.6	C13—C12—H12A	120.1
C4—C5—C6	120.9 (3)	C11—C12—H12A	120.1
C4—C5—H5A	119.6	C12—C13—C14	119.7 (4)
C6—C5—H5A	119.6	C12—C13—H13A	120.1
C5—C6—C1	119.2 (3)	C14—C13—H13A	120.1
C5—C6—C7	117.7 (3)	C15—C14—C13	120.4 (4)
C1—C6—C7	123.0 (3)	C15—C14—H14A	119.8
O1—C7—C8	120.9 (4)	C13—C14—H14A	119.8
O1—C7—C6	119.9 (3)	C14—C15—C10	121.2 (4)
C8—C7—C6	119.2 (3)	C14—C15—H15A	119.4
C9—C8—C7	119.5 (3)	C10—C15—H15A	119.4
C9—C8—H8A	120.2

C6—C1—C2—C3	0.1 (6)	C6—C7—C8—C9	173.5 (4)
C1—C2—C3—C4	−0.9 (6)	C7—C8—C9—C10	176.9 (3)
C1—C2—C3—Br1	178.1 (3)	C8—C9—C10—C15	−2.7 (6)
C2—C3—C4—C5	1.1 (6)	C8—C9—C10—C11	179.0 (4)
Br1—C3—C4—C5	−177.9 (3)	C15—C10—C11—C12	−0.3 (5)
C3—C4—C5—C6	−0.7 (6)	C9—C10—C11—C12	178.1 (3)
C4—C5—C6—C1	0.0 (6)	C15—C10—C11—Cl1	179.1 (3)
C4—C5—C6—C7	176.4 (3)	C9—C10—C11—Cl1	−2.5 (5)
C2—C1—C6—C5	0.3 (6)	C10—C11—C12—C13	−0.4 (6)
C2—C1—C6—C7	−175.9 (4)	Cl1—C11—C12—C13	−179.8 (3)
C5—C6—C7—O1	−10.8 (5)	C11—C12—C13—C14	0.7 (6)
C1—C6—C7—O1	165.5 (4)	C12—C13—C14—C15	−0.4 (6)
C5—C6—C7—C8	168.8 (3)	C13—C14—C15—C10	−0.2 (6)
C1—C6—C7—C8	−15.0 (5)	C11—C10—C15—C14	0.6 (5)
O1—C7—C8—C9	−7.0 (6)	C9—C10—C15—C14	−177.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1ⁱ	0.93	2.53	3.191 (4)	128
C9—H9A···Cl1	0.93	2.61	3.064 (4)	111
C9—H9A···O1	0.93	2.41	2.765 (5)	102

Symmetry code: (i) −x, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀BrClO
M_r	321.59
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	27.8720 (6), 3.9235 (1), 11.6408 (2)
V (Å³)	1272.99 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.42
Crystal size (mm)	0.33 × 0.18 × 0.09

Data collection
Diffractometer	Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.392, 0.736
No. of measured, independent and observed [I > 2σ(I)] reflections	9658, 3495, 2938
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.086, 1.03
No. of reflections	3495
No. of parameters	163
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.44
Absolute structure	Flack (1983), 1545 Friedel pairs
Absolute structure parameter	0.011 (12)

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
C1—H1A···O1ⁱ	0.93	2.53	3.191 (4)	128
C9—H9A···Cl1	0.93	2.61	3.064 (4)	111
C9—H9A···O1	0.93	2.41	2.765 (5)	102

Symmetry code: (i) −x, −y, z−1/2.

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. SC thanks Prince of Songkla University for generous support. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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