(E)-3-(3-Bromo-phen-yl)-1-(4-methyl-phenyl)prop-2-en-1-one.

The title compound, C(16)H(13)BrO, was synthesized from the reaction of 3-bromo-benzaldehyde and 4-methyl-acetophenone in the presence of KOH. The mol-ecule 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 inter-actions [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 = 301.17

Triclinic,

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[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.168

S = 1.00

2312 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H13BrO	Z = 2
Mr = 301.17	F(000) = 304
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.078P)2 + 0.164P] where P = (Fo2 + 2Fc2)/3
2312 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)