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

Li, H.; Sarojini, B.K.; Raj, C.G.D.; Madhu, L.N.; Yathirajan, H.S.

doi:10.1107/S1600536808034867

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2238

doi:10.1107/S1600536808034867

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

Hongqi Li,^a ^* B. K. Sarojini,^b C. G. D. Raj,^b L. N. Madhu ^b and H. S. Yathirajan ^c

^aKey Laboratory of Science & Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering & Biotechnology, Donghua University, Shanghai 201620, People's Republic of China, ^bDepartment of Chemistry, PA College of Engineering, Nadupadavu, Mangalore 574 153, India, and ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: hongqili@dhu.edu.cn

(Received 15 October 2008; accepted 25 October 2008; online 31 October 2008)

The title compound, C₁₆H₁₃BrO, was synthesized from the reaction of 3-bromobenzaldehyde and 4-methylacetophenone in the presence of KOH. The molecule adopts an E configuration with respect to the C=C double bond of the propenone unit. The dihedral angle formed by the aromatic rings is 46.91 (14)°. The crystal structure is stabilized by Br⋯Br interactions [3.4549 (11) Å].

Related literature

For the properties and applications of chalcones, see: Pandey et al. (2005 ); Conti (2006 ); Lawrence et al. (2001 ); Nielsen et al. (2005 ); Dominguez et al. (2005 ). For related structures, see: Sarojini et al. (2007 ) and references cited therein.

Experimental

Crystal data

C₁₆H₁₃BrO
M_r = 301.17
Triclinic, $[P \overline 1]$
a = 5.8984 (16) Å
b = 7.3015 (19) Å
c = 15.559 (4) Å
α = 83.461 (5)°
β = 87.860 (4)°
γ = 88.446 (5)°
V = 665.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 3.08 mm⁻¹
T = 273 (2) K
0.12 × 0.10 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.709, T_max = 0.837
3407 measured reflections
2312 independent reflections
1457 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.168
S = 1.00
2312 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034867/rz2257sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034867/rz2257Isup2.hkl

checkCIF report

Comment top

Chalcones are a class of naturally occurring compounds with interesting biological properties such as cytotoxicity (Pandey et al., 2005), antiherpes activity and antitumour activity (Conti, 2006) and may be useful for the chemotherapy of leishmaniasis among others (Lawrence et al., 2001). Chalcone derivatives are also used as antibiotics (Nielsen et al., 2005) and as anti malerials (Dominguez et al., 2005). Recently, the crystal structures of some methyl- and bromo-substituted chalcones have been reported by our group (Sarojini et al., 2007 and references cited therein). In a continuation of our studies, the title chalcone derivative was synthesized and its crystal structure is reported here.

The molecule of the title compound (Fig. 1) adopts an E configuration with respect to the C═C double bond of the propenone unit. The two aromatic rings are not coplanar, they dihedral angle they form being 46.91 (14) °. Molecular dimensions are unexceptional. The crystal structure is stabilized by Br···Br interactions occurring between centrosymmetrically-related molecules [Br1···Br1ⁱ = 3.4549 (11) Å; symmetry code: (i) -x, 2-y, -z].

Related literature top

For the properties and applications of chalcones, see: Pandey et al. (2005); Conti (2006); Lawrence et al. (2001); Nielsen et al. (2005); Dominguez et al. (2005). For related structures, see: Sarojini et al. (2007) and references cited therein.

Experimental top

The title compound was prepared by adding 50% KOH (2.5 ml) to a solution of 4-methylacetophenone (1.34 g, 0.01 mol) and 3-bromobenzaldehyde (1.86 g, 0.01 mol) in ethanol (25 ml) at 273 K. The mixture was stirred for an hour and poured into crushed ice. The resulting yellow precipitate was collected by filtration and purified by recrystallization from ethanol. Single crystals suitable for X-ray analysis were grown by slow evaporation of an acetone solution (yield 80%). Analytical data: found (calculated): C %, 63.78 (63.81); H%, 4.30 (4.35).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecule of the title compound. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

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

Crystal data top

C₁₆H₁₃BrO	Z = 2
M_r = 301.17	F(000) = 304
Triclinic, P1	D_x = 1.504 Mg m⁻³
Hall symbol: -P 1	Melting point = 378–380 K
a = 5.8984 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.3015 (19) Å	Cell parameters from 1237 reflections
c = 15.559 (4) Å	θ = 2.6–23.7°
α = 83.461 (5)°	µ = 3.08 mm⁻¹
β = 87.860 (4)°	T = 273 K
γ = 88.446 (5)°	Block, colourless
V = 665.1 (3) Å³	0.12 × 0.10 × 0.06 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2312 independent reflections
Radiation source: fine-focus sealed tube	1457 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −7→6
T_min = 0.709, T_max = 0.837	k = −8→6
3407 measured reflections	l = −18→18

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.078P)² + 0.164P] where P = (F_o² + 2F_c²)/3
2312 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₆H₁₃BrO	γ = 88.446 (5)°
M_r = 301.17	V = 665.1 (3) Å³
Triclinic, P1	Z = 2
a = 5.8984 (16) Å	Mo Kα radiation
b = 7.3015 (19) Å	µ = 3.08 mm⁻¹
c = 15.559 (4) Å	T = 273 K
α = 83.461 (5)°	0.12 × 0.10 × 0.06 mm
β = 87.860 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2312 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1457 reflections with I > 2σ(I)
T_min = 0.709, T_max = 0.837	R_int = 0.049
3407 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.00	Δρ_max = 0.57 e Å⁻³
2312 reflections	Δρ_min = −0.44 e Å⁻³
163 parameters

Special details top

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	0.20271 (11)	0.91736 (11)	0.07283 (4)	0.0905 (4)
O1	−0.2214 (6)	0.7140 (5)	0.5453 (2)	0.0640 (10)
C1	0.3158 (8)	0.9176 (7)	0.1855 (3)	0.0522 (13)
C2	0.1824 (8)	0.8504 (7)	0.2552 (3)	0.0475 (12)
H2	0.0413	0.8024	0.2469	0.057*
C3	0.2584 (7)	0.8541 (6)	0.3379 (3)	0.0436 (11)
C4	0.4711 (8)	0.9273 (6)	0.3481 (3)	0.0474 (12)
H4	0.5246	0.9308	0.4033	0.057*
C5	0.6015 (8)	0.9939 (7)	0.2770 (4)	0.0512 (13)
H5	0.7434	1.0412	0.2844	0.061*
C6	0.5234 (8)	0.9912 (7)	0.1949 (4)	0.0556 (13)
H6	0.6100	1.0385	0.1466	0.067*
C7	0.1059 (7)	0.7893 (6)	0.4108 (3)	0.0458 (12)
H7	−0.0429	0.7673	0.3978	0.055*
C8	0.1579 (8)	0.7590 (7)	0.4923 (3)	0.0519 (13)
H8	0.3069	0.7715	0.5079	0.062*
C9	−0.0197 (8)	0.7046 (6)	0.5605 (3)	0.0476 (12)
C10	0.0571 (7)	0.6411 (6)	0.6491 (3)	0.0433 (11)
C11	0.2715 (8)	0.5634 (7)	0.6637 (4)	0.0502 (12)
H11	0.3718	0.5491	0.6172	0.060*
C12	0.3359 (8)	0.5073 (7)	0.7474 (4)	0.0518 (13)
H12	0.4773	0.4506	0.7567	0.062*
C13	0.1921 (8)	0.5347 (7)	0.8172 (3)	0.0503 (12)
C14	−0.0198 (8)	0.6113 (7)	0.8023 (3)	0.0544 (13)
H14	−0.1188	0.6276	0.8489	0.065*
C15	−0.0881 (8)	0.6646 (6)	0.7191 (3)	0.0468 (12)
H15	−0.2322	0.7164	0.7101	0.056*
C16	0.2693 (12)	0.4783 (10)	0.9080 (4)	0.0823 (19)
H16A	0.1875	0.5502	0.9474	0.123*
H16B	0.4289	0.4988	0.9104	0.123*
H16C	0.2405	0.3499	0.9240	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0839 (5)	0.1354 (8)	0.0529 (5)	−0.0024 (4)	−0.0134 (3)	−0.0102 (4)
O1	0.043 (2)	0.084 (3)	0.064 (2)	−0.0043 (17)	−0.0094 (17)	−0.002 (2)
C1	0.050 (3)	0.063 (3)	0.044 (3)	0.006 (2)	−0.003 (2)	−0.005 (2)
C2	0.038 (2)	0.053 (3)	0.052 (3)	0.001 (2)	−0.007 (2)	−0.009 (2)
C3	0.037 (2)	0.042 (3)	0.052 (3)	0.002 (2)	0.000 (2)	−0.009 (2)
C4	0.039 (3)	0.050 (3)	0.055 (3)	−0.001 (2)	−0.005 (2)	−0.015 (2)
C5	0.039 (3)	0.048 (3)	0.068 (4)	−0.002 (2)	−0.004 (3)	−0.012 (3)
C6	0.048 (3)	0.060 (3)	0.057 (3)	0.001 (2)	0.007 (2)	−0.004 (3)
C7	0.036 (2)	0.045 (3)	0.059 (3)	−0.002 (2)	−0.009 (2)	−0.012 (2)
C8	0.043 (3)	0.058 (3)	0.056 (3)	−0.007 (2)	−0.007 (2)	−0.010 (3)
C9	0.042 (3)	0.039 (3)	0.063 (3)	−0.007 (2)	0.001 (2)	−0.009 (2)
C10	0.037 (2)	0.036 (3)	0.057 (3)	−0.0047 (19)	−0.003 (2)	−0.005 (2)
C11	0.039 (3)	0.049 (3)	0.062 (3)	−0.003 (2)	0.011 (2)	−0.010 (3)
C12	0.039 (3)	0.046 (3)	0.068 (4)	0.000 (2)	−0.004 (3)	0.003 (3)
C13	0.049 (3)	0.047 (3)	0.053 (3)	−0.007 (2)	0.000 (2)	−0.001 (2)
C14	0.047 (3)	0.062 (3)	0.054 (3)	−0.003 (2)	0.011 (2)	−0.008 (3)
C15	0.038 (2)	0.043 (3)	0.058 (3)	−0.002 (2)	0.005 (2)	−0.005 (2)
C16	0.085 (4)	0.091 (5)	0.069 (4)	0.000 (4)	−0.011 (4)	0.002 (4)

Geometric parameters (Å, º) top

Br1—C1	1.899 (5)	C8—H8	0.9300
O1—C9	1.220 (6)	C9—C10	1.486 (7)
C1—C2	1.368 (7)	C10—C15	1.383 (7)
C1—C6	1.370 (7)	C10—C11	1.388 (6)
C2—C3	1.382 (6)	C11—C12	1.384 (7)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.398 (6)	C12—C13	1.382 (7)
C3—C7	1.464 (7)	C12—H12	0.9300
C4—C5	1.374 (7)	C13—C14	1.373 (7)
C4—H4	0.9300	C13—C16	1.510 (8)
C5—C6	1.377 (7)	C14—C15	1.380 (7)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.309 (7)	C16—H16A	0.9600
C7—H7	0.9300	C16—H16B	0.9600
C8—C9	1.491 (7)	C16—H16C	0.9600

C2—C1—C6	122.1 (5)	C10—C9—C8	117.6 (4)
C2—C1—Br1	118.6 (4)	C15—C10—C11	119.2 (5)
C6—C1—Br1	119.3 (4)	C15—C10—C9	118.8 (4)
C1—C2—C3	119.6 (4)	C11—C10—C9	122.0 (4)
C1—C2—H2	120.2	C12—C11—C10	119.9 (5)
C3—C2—H2	120.2	C12—C11—H11	120.0
C2—C3—C4	118.7 (5)	C10—C11—H11	120.0
C2—C3—C7	117.9 (4)	C13—C12—C11	120.7 (4)
C4—C3—C7	123.3 (4)	C13—C12—H12	119.7
C5—C4—C3	120.4 (5)	C11—C12—H12	119.7
C5—C4—H4	119.8	C14—C13—C12	119.1 (5)
C3—C4—H4	119.8	C14—C13—C16	121.2 (5)
C4—C5—C6	120.4 (4)	C12—C13—C16	119.7 (5)
C4—C5—H5	119.8	C13—C14—C15	120.9 (5)
C6—C5—H5	119.8	C13—C14—H14	119.6
C1—C6—C5	118.7 (5)	C15—C14—H14	119.6
C1—C6—H6	120.6	C14—C15—C10	120.2 (4)
C5—C6—H6	120.6	C14—C15—H15	119.9
C8—C7—C3	126.6 (4)	C10—C15—H15	119.9
C8—C7—H7	116.7	C13—C16—H16A	109.5
C3—C7—H7	116.7	C13—C16—H16B	109.5
C7—C8—C9	120.6 (5)	H16A—C16—H16B	109.5
C7—C8—H8	119.7	C13—C16—H16C	109.5
C9—C8—H8	119.7	H16A—C16—H16C	109.5
O1—C9—C10	120.6 (5)	H16B—C16—H16C	109.5
O1—C9—C8	121.8 (5)

C6—C1—C2—C3	−0.7 (7)	O1—C9—C10—C15	−26.2 (7)
Br1—C1—C2—C3	−178.1 (3)	C8—C9—C10—C15	152.7 (4)
C1—C2—C3—C4	0.1 (7)	O1—C9—C10—C11	155.4 (5)
C1—C2—C3—C7	177.1 (4)	C8—C9—C10—C11	−25.7 (6)
C2—C3—C4—C5	0.0 (7)	C15—C10—C11—C12	1.3 (7)
C7—C3—C4—C5	−176.8 (4)	C9—C10—C11—C12	179.6 (4)
C3—C4—C5—C6	0.6 (7)	C10—C11—C12—C13	−2.7 (7)
C2—C1—C6—C5	1.3 (8)	C11—C12—C13—C14	2.8 (7)
Br1—C1—C6—C5	178.7 (4)	C11—C12—C13—C16	−177.9 (5)
C4—C5—C6—C1	−1.3 (7)	C12—C13—C14—C15	−1.5 (7)
C2—C3—C7—C8	170.1 (5)	C16—C13—C14—C15	179.2 (5)
C4—C3—C7—C8	−13.1 (7)	C13—C14—C15—C10	0.1 (7)
C3—C7—C8—C9	176.0 (4)	C11—C10—C15—C14	0.0 (7)
C7—C8—C9—O1	−11.5 (7)	C9—C10—C15—C14	−178.4 (4)
C7—C8—C9—C10	169.6 (4)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃BrO
M_r	301.17
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	5.8984 (16), 7.3015 (19), 15.559 (4)
α, β, γ (°)	83.461 (5), 87.860 (4), 88.446 (5)
V (Å³)	665.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.08
Crystal size (mm)	0.12 × 0.10 × 0.06

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.709, 0.837
No. of measured, independent and observed [I > 2σ(I)] reflections	3407, 2312, 1457
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.168, 1.00
No. of reflections	2312
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.44

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

BKS thanks BRNS, DAE, Government of India (grant No. 2008/34/05-BRNS/457).

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