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

Jasinski, J.P.; Butcher, R.J.; Narayana, B.; Veena, K.; Yathirajan, H.S.

doi:10.1107/S1600536809053446

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o158

doi:10.1107/S1600536809053446

Open

access

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

Jerry P. Jasinski,^a ^* Ray J. Butcher,^b B. Narayana,^c K. Veena ^c and H. S. Yathirajan ^d

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, ^cDepartment of Studies in Chemistry, Mangalore University, Manalaganotri, 574 199, India, and ^dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 5 December 2009; accepted 11 December 2009; online 16 December 2009)

In the title compound, C₁₅H₁₀BrClO, the dihedral angle between mean planes of the bromo- and chloro-substituted benzene rings is 46.2 (2)° compared to 45.20 (9)° in the structure with the Cl substituent in the meta position of the aromatic ring. The dihedral angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 4-bromophenyl and 3-chlorophenyl rings are 28.7 (5) and 24.2 (4)°, respectively. In the crystal, weak intermolecular C—H⋯π interactions occur.

Related literature

For a related structure, see: Ng et al. (2006 ).

Experimental

Crystal data

C₁₅H₁₀BrClO
M_r = 321.59
Triclinic, $[P \overline 1]$
a = 5.9197 (8) Å
b = 7.3391 (11) Å
c = 14.8171 (17) Å
α = 101.929 (11)°
β = 94.371 (10)°
γ = 93.299 (11)°
V = 626.22 (15) Å³
Z = 2
Cu Kα radiation
μ = 6.29 mm⁻¹
T = 110 K
0.50 × 0.21 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.041, T_max = 0.344
3868 measured reflections
2432 independent reflections
2312 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.164
S = 1.07
2432 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 1.78 e Å⁻³
Δρ_min = −1.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2A—H2AA⋯Cg2ⁱ	0.95	2.97	3.588 (4)	124
C5A—H5AA⋯Cg2ⁱⁱ	0.95	2.84	3.463 (4)	124
C12A—H12A⋯Cg1ⁱⁱⁱ	0.95	2.83	3.527 (4)	131
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y, -z+1; (iii) -x, -y+1, -z+1. Cg1 is the centroid of the C1A–C6A ring and Cg2 is the centroid of the C10A–C15A ring.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; 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/S1600536809053446/bt5130sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809053446/bt5130Isup2.hkl

checkCIF report

Comment top

In continuation of our interest in the synthesis and crystal structure determination of chalcones, the title chalcone, C₁₅H₁₀BrClO, is synthesized and its crystal structure is reported.

The title compound, (I), is a chalcone derivative with 4-bromophenyl and 3-chlorophenyl rings bonded at the opposite ends of a propenone group, the biologically active region (Fig.1). The dihedral angle between mean planes of the chloro and bromo substituted benzene rings is 46.2 (2)° compared to 45.20 (9)° (Ng et al. (2006)) and 46.70 (5)° for a similar related molecule. The angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 4-bromophenyl and 3-chlorophenyl rings are 28.7 (5)° and 24.2 (4)° and respectively. This compares to 20.66 (1)° and 24.54 (1)° in the similar structure. While no classical hydrogen bonds are present, weak intermolecular C–H···π-ring interactions are observed which contribute to the stability of crystal packing (Fig.2, Table 1).

Related literature top

For a related structure, see: Ng et al. (2006).

Experimental top

50% KOH was added to a mixture of 3-chloroacetophenone (0.01 mol) and p-bromobenzaldehyde (0.01 mol) in 25 ml of ethanol (Scheme 2). The mixture was stirred for an hour at room temperature and the precipitate was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from ethyl acetate by slow evaporation method with the yield of the compound being 70% (m.p.412–414 K). Analytical data for C₁₅H₁₀BrClO: Found (Calculated): C %: 55.97 (56.02); H%: 3.09 (3.13).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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. Molecular structure of the title compound, C₁₅H₁₀BrClO, showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound, (I), viewed down the a axis.
	Fig. 3. The formation of the title compound.

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

Crystal data top

C₁₅H₁₀BrClO	Z = 2
M_r = 321.59	F(000) = 320
Triclinic, P1	D_x = 1.706 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 5.9197 (8) Å	Cell parameters from 3370 reflections
b = 7.3391 (11) Å	θ = 6.1–73.9°
c = 14.8171 (17) Å	µ = 6.29 mm⁻¹
α = 101.929 (11)°	T = 110 K
β = 94.371 (10)°	Plate, colorless
γ = 93.299 (11)°	0.50 × 0.21 × 0.12 mm
V = 626.22 (15) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector	2432 independent reflections
Radiation source: fine-focus sealed tube	2312 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 10.5081 pixels mm^-1	θ_max = 74.0°, θ_min = 6.1°
ω scans	h = −7→6
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007)	k = −9→8
T_min = 0.041, T_max = 0.344	l = −18→18
3868 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1305P)² + 0.5925P] where P = (F_o² + 2F_c²)/3
2432 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 1.78 e Å⁻³
0 restraints	Δρ_min = −1.29 e Å⁻³

Crystal data top

C₁₅H₁₀BrClO	γ = 93.299 (11)°
M_r = 321.59	V = 626.22 (15) Å³
Triclinic, P1	Z = 2
a = 5.9197 (8) Å	Cu Kα radiation
b = 7.3391 (11) Å	µ = 6.29 mm⁻¹
c = 14.8171 (17) Å	T = 110 K
α = 101.929 (11)°	0.50 × 0.21 × 0.12 mm
β = 94.371 (10)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector	2432 independent reflections
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007)	2312 reflections with I > 2σ(I)
T_min = 0.041, T_max = 0.344	R_int = 0.037
3868 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.07	Δρ_max = 1.78 e Å⁻³
2432 reflections	Δρ_min = −1.29 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
Br1A	−0.10431 (6)	0.72017 (5)	0.94001 (2)	0.0266 (2)
Cl1A	0.58277 (16)	−0.04318 (14)	0.11075 (6)	0.0269 (3)
O1A	0.7080 (5)	0.2207 (4)	0.47588 (19)	0.0270 (6)
C12A	−0.0341 (6)	0.5947 (5)	0.7495 (3)	0.0205 (7)
H12A	−0.1777	0.6408	0.7378	0.025*
C1A	0.3919 (6)	0.1019 (5)	0.3683 (3)	0.0195 (7)
C2A	0.5227 (6)	0.0801 (5)	0.2923 (3)	0.0214 (7)
H2AA	0.6756	0.1315	0.2992	0.026*
C11A	0.0849 (6)	0.5125 (5)	0.6764 (3)	0.0215 (7)
H11A	0.0215	0.5019	0.6146	0.026*
C5A	0.0776 (6)	−0.0794 (5)	0.2713 (3)	0.0232 (8)
H5AA	−0.0727	−0.1364	0.2645	0.028*
C10A	0.2967 (6)	0.4452 (5)	0.6929 (3)	0.0207 (7)
C8A	0.3490 (7)	0.2931 (6)	0.5299 (3)	0.0245 (8)
H8AA	0.1944	0.3044	0.5110	0.029*
C14A	0.2701 (6)	0.5451 (5)	0.8595 (3)	0.0229 (7)
H14A	0.3318	0.5556	0.9216	0.027*
C3A	0.4245 (6)	−0.0180 (5)	0.2068 (3)	0.0200 (7)
C15A	0.3894 (6)	0.4648 (5)	0.7854 (2)	0.0210 (7)
H15A	0.5352	0.4227	0.7974	0.025*
C13A	0.0594 (7)	0.6090 (5)	0.8404 (2)	0.0200 (7)
C6A	0.1690 (6)	0.0229 (5)	0.3577 (3)	0.0214 (7)
H6AA	0.0799	0.0386	0.4091	0.026*
C7A	0.5018 (6)	0.2071 (5)	0.4605 (2)	0.0213 (7)
C9A	0.4280 (6)	0.3546 (5)	0.6187 (3)	0.0210 (7)
H9AA	0.5826	0.3381	0.6351	0.025*
C4A	0.2037 (6)	−0.0988 (5)	0.1951 (3)	0.0228 (7)
H4AA	0.1399	−0.1661	0.1360	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1A	0.0240 (3)	0.0339 (3)	0.0202 (3)	0.00673 (19)	0.00381 (18)	0.0001 (2)
Cl1A	0.0292 (5)	0.0316 (5)	0.0200 (5)	0.0051 (4)	0.0061 (3)	0.0036 (4)
O1A	0.0217 (13)	0.0343 (15)	0.0224 (14)	0.0029 (12)	0.0001 (10)	0.0010 (11)
C12A	0.0183 (16)	0.0213 (17)	0.0211 (17)	−0.0020 (13)	−0.0003 (13)	0.0044 (14)
C1A	0.0205 (17)	0.0196 (17)	0.0191 (17)	0.0030 (13)	0.0014 (13)	0.0057 (13)
C2A	0.0207 (17)	0.0211 (17)	0.0213 (17)	0.0032 (14)	−0.0002 (13)	0.0026 (14)
C11A	0.0230 (17)	0.0209 (17)	0.0195 (17)	−0.0015 (14)	−0.0015 (13)	0.0039 (13)
C5A	0.0174 (16)	0.0211 (17)	0.030 (2)	−0.0020 (13)	−0.0039 (14)	0.0061 (15)
C10A	0.0222 (18)	0.0199 (17)	0.0194 (17)	−0.0032 (14)	−0.0003 (14)	0.0050 (13)
C8A	0.0228 (18)	0.0278 (19)	0.0217 (18)	0.0016 (14)	0.0005 (14)	0.0033 (15)
C14A	0.0227 (18)	0.0233 (18)	0.0213 (17)	−0.0006 (14)	−0.0019 (14)	0.0036 (14)
C3A	0.0201 (17)	0.0211 (18)	0.0197 (17)	0.0058 (13)	0.0029 (13)	0.0047 (14)
C15A	0.0179 (16)	0.0258 (18)	0.0192 (17)	0.0022 (13)	0.0018 (13)	0.0045 (14)
C13A	0.0252 (18)	0.0181 (17)	0.0155 (17)	0.0027 (14)	0.0045 (14)	−0.0006 (13)
C6A	0.0208 (17)	0.0239 (18)	0.0208 (18)	0.0013 (14)	0.0034 (13)	0.0075 (14)
C7A	0.0239 (17)	0.0218 (17)	0.0187 (17)	0.0006 (14)	0.0017 (14)	0.0061 (14)
C9A	0.0203 (17)	0.0208 (17)	0.0218 (18)	−0.0003 (14)	0.0008 (14)	0.0055 (14)
C4A	0.0240 (18)	0.0218 (17)	0.0203 (17)	0.0035 (14)	−0.0043 (14)	0.0008 (14)

Geometric parameters (Å, º) top

Br1A—C13A	1.896 (4)	C5A—H5AA	0.9500
Cl1A—C3A	1.747 (4)	C10A—C15A	1.413 (5)
O1A—C7A	1.219 (5)	C10A—C9A	1.463 (5)
C12A—C11A	1.388 (6)	C8A—C9A	1.339 (5)
C12A—C13A	1.398 (5)	C8A—C7A	1.487 (5)
C12A—H12A	0.9500	C8A—H8AA	0.9500
C1A—C6A	1.395 (5)	C14A—C13A	1.387 (5)
C1A—C2A	1.402 (5)	C14A—C15A	1.396 (5)
C1A—C7A	1.503 (5)	C14A—H14A	0.9500
C2A—C3A	1.387 (5)	C3A—C4A	1.387 (5)
C2A—H2AA	0.9500	C15A—H15A	0.9500
C11A—C10A	1.396 (5)	C6A—H6AA	0.9500
C11A—H11A	0.9500	C9A—H9AA	0.9500
C5A—C4A	1.388 (6)	C4A—H4AA	0.9500
C5A—C6A	1.395 (5)

C11A—C12A—C13A	119.4 (3)	C15A—C14A—H14A	120.7
C11A—C12A—H12A	120.3	C2A—C3A—C4A	122.0 (3)
C13A—C12A—H12A	120.3	C2A—C3A—Cl1A	119.4 (3)
C6A—C1A—C2A	120.2 (3)	C4A—C3A—Cl1A	118.6 (3)
C6A—C1A—C7A	121.8 (3)	C14A—C15A—C10A	121.1 (3)
C2A—C1A—C7A	117.9 (3)	C14A—C15A—H15A	119.5
C3A—C2A—C1A	118.7 (3)	C10A—C15A—H15A	119.5
C3A—C2A—H2AA	120.7	C14A—C13A—C12A	121.5 (3)
C1A—C2A—H2AA	120.7	C14A—C13A—Br1A	119.2 (3)
C12A—C11A—C10A	120.8 (3)	C12A—C13A—Br1A	119.3 (3)
C12A—C11A—H11A	119.6	C1A—C6A—C5A	119.6 (3)
C10A—C11A—H11A	119.6	C1A—C6A—H6AA	120.2
C4A—C5A—C6A	120.7 (3)	C5A—C6A—H6AA	120.2
C4A—C5A—H5AA	119.6	O1A—C7A—C8A	122.6 (3)
C6A—C5A—H5AA	119.6	O1A—C7A—C1A	120.2 (3)
C11A—C10A—C15A	118.7 (4)	C8A—C7A—C1A	117.2 (3)
C11A—C10A—C9A	123.1 (3)	C8A—C9A—C10A	125.6 (4)
C15A—C10A—C9A	118.2 (3)	C8A—C9A—H9AA	117.2
C9A—C8A—C7A	120.4 (4)	C10A—C9A—H9AA	117.2
C9A—C8A—H8AA	119.8	C3A—C4A—C5A	118.8 (3)
C7A—C8A—H8AA	119.8	C3A—C4A—H4AA	120.6
C13A—C14A—C15A	118.5 (3)	C5A—C4A—H4AA	120.6
C13A—C14A—H14A	120.7

C6A—C1A—C2A—C3A	1.2 (5)	C7A—C1A—C6A—C5A	−177.6 (3)
C7A—C1A—C2A—C3A	179.4 (3)	C4A—C5A—C6A—C1A	−1.9 (6)
C13A—C12A—C11A—C10A	−0.4 (6)	C9A—C8A—C7A—O1A	−14.5 (6)
C12A—C11A—C10A—C15A	−0.9 (6)	C9A—C8A—C7A—C1A	166.1 (4)
C12A—C11A—C10A—C9A	179.0 (3)	C6A—C1A—C7A—O1A	155.6 (4)
C1A—C2A—C3A—C4A	−1.7 (5)	C2A—C1A—C7A—O1A	−22.6 (5)
C1A—C2A—C3A—Cl1A	178.8 (3)	C6A—C1A—C7A—C8A	−25.0 (5)
C13A—C14A—C15A—C10A	−1.3 (6)	C2A—C1A—C7A—C8A	156.8 (3)
C11A—C10A—C15A—C14A	1.7 (6)	C7A—C8A—C9A—C10A	178.5 (3)
C9A—C10A—C15A—C14A	−178.1 (3)	C11A—C10A—C9A—C8A	−13.4 (6)
C15A—C14A—C13A—C12A	0.0 (6)	C15A—C10A—C9A—C8A	166.4 (4)
C15A—C14A—C13A—Br1A	−179.5 (3)	C2A—C3A—C4A—C5A	0.4 (5)
C11A—C12A—C13A—C14A	0.8 (6)	Cl1A—C3A—C4A—C5A	179.8 (3)
C11A—C12A—C13A—Br1A	−179.7 (3)	C6A—C5A—C4A—C3A	1.4 (6)
C2A—C1A—C6A—C5A	0.6 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1A–C6A ring and Cg2 is the centroid of the C10A–C15A ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2A—H2AA···Cg2ⁱ	0.95	2.97	3.588 (4)	124
C5A—H5AA···Cg2ⁱⁱ	0.95	2.84	3.463 (4)	124
C12A—H12A···Cg1ⁱⁱⁱ	0.95	2.83	3.527 (4)	131

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z+1; (iii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀BrClO
M_r	321.59
Crystal system, space group	Triclinic, P1
Temperature (K)	110
a, b, c (Å)	5.9197 (8), 7.3391 (11), 14.8171 (17)
α, β, γ (°)	101.929 (11), 94.371 (10), 93.299 (11)
V (Å³)	626.22 (15)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	6.29
Crystal size (mm)	0.50 × 0.21 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.041, 0.344
No. of measured, independent and observed [I > 2σ(I)] reflections	3868, 2432, 2312
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.164, 1.07
No. of reflections	2432
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.78, −1.29

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97) (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1A–C6A ring and Cg2 is the centroid of the C10A–C15A ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2A—H2AA···Cg2ⁱ	0.95	2.97	3.588 (4)	124
C5A—H5AA···Cg2ⁱⁱ	0.95	2.84	3.463 (4)	124
C12A—H12A···Cg1ⁱⁱⁱ	0.95	2.83	3.527 (4)	131

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z+1; (iii) −x, −y+1, −z+1.

Acknowledgements

KV thanksthe UGC for the sanction of a Junior Research Fellowship and for a SAP Chemical grant. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

Ng, S.-L., Razak, I. A., Fun, H.-K., Shettigar, V., Patil, P. S. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o2175–o2177. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar