(E)-1-(4-Bromo-phen-yl)-3-(2-meth-oxy-phen-yl)prop-2-en-1-one.

In the title compound, C(16)H(13)BrO(2), the dihedral angle between the mean planes of the meth-oxy- and bromo-substituted benzene rings is 24.6 (1)°. The angles between the mean plane of the prop-2-en-1-one group and the 4-bromo-phenyl and 2-meth-oxy-phenyl ring planes are 18.8 (1) and 6.0 (1)°, respectively.

Related literature

For the use of chalcone compounds or chalcone-rich plant extracts as drugs or food preservatives, see: Dhar (1981 ▶). For the anti-inflammatory, anti­microbial, anti­fungal, anti­oxidant, cytotoxic, and anti­cancer activity of chalcones, see: Dimmock et al. (1999 ▶). For their high anti­malarial activity, see: Troeberg et al. (2000 ▶). For SHG conversion efficiencies, see: Sarojini et al. (2006 ▶). For related structures, see: Arai et al. (1994 ▶); Shettigar et al. (2006 ▶); Rosli et al. (2006 ▶); Ng et al. (2006 ▶); Harrison et al. (2006 ▶); Patil et al. (2007 ▶); Li et al. (1992 ▶); Loh et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H13BrO2

M = 317.17

Monoclinic,

a = 17.729 (4) Å

b = 4.3505 (9) Å

c = 19.335 (4) Å

β = 116.93 (3)°

V = 1329.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.09 mm−1

T = 100 K

0.55 × 0.50 × 0.35 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.674, T max = 0.746

19884 measured reflections

4121 independent reflections

3635 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.070

S = 1.32

4121 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810026814/ci5129sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026814/ci5129Isup2.hkl

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

C16H13BrO2	F(000) = 640
Mr = 317.17	Dx = 1.584 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 6810 reflections
a = 17.729 (4) Å	θ = 2.4–31.2°
b = 4.3505 (9) Å	µ = 3.09 mm−1
c = 19.335 (4) Å	T = 100 K
β = 116.93 (3)°	Block, yellow
V = 1329.6 (5) Å3	0.55 × 0.50 × 0.35 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4121 independent reflections
Radiation source: fine-focus sealed tube	3635 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 31.3°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −25→25
Tmin = 0.674, Tmax = 0.746	k = −6→6
19884 measured reflections	l = −27→28

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H-atom parameters constrained
S = 1.32	w = 1/[σ2(Fo2) + (0.0363P)2] where P = (Fo2 + 2Fc2)/3
4121 reflections	(Δ/σ)max = 0.002
173 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.22 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	0.945523 (8)	−0.41655 (3)	0.378517 (7)	0.02597 (6)
O1	0.68442 (7)	0.3686 (3)	0.49024 (6)	0.0336 (2)
O2	0.43404 (7)	0.9395 (2)	0.39362 (6)	0.0264 (2)
C1	0.73529 (8)	0.1076 (3)	0.41311 (7)	0.0189 (2)
C2	0.81716 (8)	0.0874 (3)	0.47366 (7)	0.0220 (2)
H2	0.8298	0.1829	0.5207	0.026*
C3	0.88004 (8)	−0.0719 (3)	0.46513 (7)	0.0231 (3)
H3	0.9346	−0.0823	0.5056	0.028*
C4	0.85962 (8)	−0.2161 (3)	0.39466 (7)	0.0205 (2)
C5	0.77855 (8)	−0.2084 (3)	0.33435 (7)	0.0218 (2)
H5	0.7657	−0.3108	0.2881	0.026*
C6	0.71655 (8)	−0.0455 (3)	0.34384 (7)	0.0208 (2)
H6	0.6618	−0.0383	0.3035	0.025*
C7	0.67125 (8)	0.2954 (3)	0.42458 (7)	0.0217 (2)
C8	0.59523 (8)	0.3990 (3)	0.35504 (7)	0.0220 (2)
H8	0.5869	0.3352	0.3062	0.026*
C9	0.53875 (9)	0.5816 (3)	0.36129 (7)	0.0228 (2)
H9	0.5472	0.6243	0.4114	0.027*
C10	0.46472 (7)	0.7234 (3)	0.29846 (7)	0.0200 (2)
C11	0.44482 (8)	0.6850 (3)	0.22024 (7)	0.0236 (2)
H11	0.4792	0.5618	0.2070	0.028*
C12	0.37500 (9)	0.8268 (3)	0.16228 (7)	0.0261 (3)
H12	0.3627	0.7990	0.1106	0.031*
C13	0.32339 (9)	1.0104 (3)	0.18148 (8)	0.0264 (3)
H13	0.2764	1.1052	0.1424	0.032*
C14	0.34131 (8)	1.0537 (3)	0.25838 (8)	0.0242 (3)
H14	0.3065	1.1775	0.2709	0.029*
C15	0.41145 (8)	0.9114 (3)	0.31666 (7)	0.0204 (2)
C16	0.38472 (10)	1.1365 (3)	0.41671 (9)	0.0305 (3)
H16A	0.3883	1.3440	0.4016	0.046*
H16B	0.4060	1.1269	0.4720	0.046*
H16C	0.3268	1.0706	0.3920	0.046*

	U11	U22	U33	U12	U13	U23
Br1	0.02597 (8)	0.02800 (8)	0.02547 (8)	0.00666 (5)	0.01300 (6)	0.00312 (5)
O1	0.0330 (5)	0.0476 (6)	0.0203 (4)	0.0095 (5)	0.0120 (4)	−0.0023 (4)
O2	0.0279 (5)	0.0312 (5)	0.0211 (4)	0.0059 (4)	0.0120 (4)	−0.0031 (4)
C1	0.0210 (6)	0.0194 (5)	0.0173 (5)	−0.0001 (4)	0.0097 (4)	0.0022 (4)
C2	0.0236 (6)	0.0248 (6)	0.0168 (5)	−0.0009 (5)	0.0086 (5)	0.0000 (4)
C3	0.0215 (6)	0.0266 (6)	0.0189 (5)	0.0007 (5)	0.0071 (5)	0.0027 (4)
C4	0.0236 (6)	0.0185 (5)	0.0217 (5)	0.0022 (4)	0.0122 (4)	0.0037 (4)
C5	0.0262 (6)	0.0204 (6)	0.0187 (5)	0.0006 (5)	0.0101 (5)	−0.0001 (4)
C6	0.0217 (6)	0.0203 (6)	0.0184 (5)	−0.0017 (4)	0.0074 (4)	0.0001 (4)
C7	0.0226 (6)	0.0233 (6)	0.0203 (5)	−0.0004 (5)	0.0108 (4)	0.0001 (4)
C8	0.0222 (6)	0.0245 (6)	0.0193 (5)	−0.0009 (5)	0.0092 (4)	−0.0015 (4)
C9	0.0222 (6)	0.0267 (6)	0.0200 (5)	−0.0026 (5)	0.0100 (5)	−0.0039 (4)
C10	0.0187 (5)	0.0203 (5)	0.0214 (5)	−0.0033 (4)	0.0094 (4)	−0.0028 (4)
C11	0.0253 (6)	0.0236 (6)	0.0234 (6)	−0.0033 (5)	0.0124 (5)	−0.0046 (5)
C12	0.0304 (7)	0.0261 (6)	0.0190 (5)	−0.0047 (5)	0.0089 (5)	−0.0015 (5)
C13	0.0233 (6)	0.0246 (6)	0.0260 (6)	−0.0021 (5)	0.0064 (5)	0.0015 (5)
C14	0.0217 (6)	0.0222 (6)	0.0284 (6)	−0.0010 (5)	0.0110 (5)	−0.0013 (5)
C15	0.0203 (6)	0.0197 (6)	0.0217 (6)	−0.0038 (4)	0.0100 (5)	−0.0031 (4)
C16	0.0345 (7)	0.0325 (7)	0.0310 (7)	0.0052 (6)	0.0206 (6)	−0.0036 (5)

Br1—C4	1.8993 (13)	C8—H8	0.93
O1—C7	1.2243 (16)	C9—C10	1.4611 (18)
O2—C15	1.3600 (15)	C9—H9	0.93
O2—C16	1.4325 (16)	C10—C11	1.3987 (17)
C1—C6	1.3945 (17)	C10—C15	1.4090 (17)
C1—C2	1.3950 (18)	C11—C12	1.383 (2)
C1—C7	1.4946 (17)	C11—H11	0.93
C2—C3	1.3846 (19)	C12—C13	1.386 (2)
C2—H2	0.93	C12—H12	0.93
C3—C4	1.3907 (17)	C13—C14	1.3853 (19)
C3—H3	0.93	C13—H13	0.93
C4—C5	1.3817 (18)	C14—C15	1.3894 (18)
C5—C6	1.3882 (18)	C14—H14	0.93
C5—H5	0.93	C16—H16A	0.96
C6—H6	0.93	C16—H16B	0.96
C7—C8	1.4787 (18)	C16—H16C	0.96
C8—C9	1.3259 (18)
C15—O2—C16	118.42 (11)	C8—C9—H9	116.3
C6—C1—C2	118.74 (12)	C10—C9—H9	116.3
C6—C1—C7	122.47 (11)	C11—C10—C15	118.03 (11)
C2—C1—C7	118.79 (11)	C11—C10—C9	122.71 (12)
C3—C2—C1	121.29 (12)	C15—C10—C9	119.25 (11)
C3—C2—H2	119.4	C12—C11—C10	121.20 (13)
C1—C2—H2	119.4	C12—C11—H11	119.4
C2—C3—C4	118.44 (12)	C10—C11—H11	119.4
C2—C3—H3	120.8	C11—C12—C13	119.82 (12)
C4—C3—H3	120.8	C11—C12—H12	120.1
C5—C4—C3	121.71 (12)	C13—C12—H12	120.1
C5—C4—Br1	118.52 (9)	C12—C13—C14	120.49 (13)
C3—C4—Br1	119.72 (10)	C12—C13—H13	119.8
C4—C5—C6	118.96 (11)	C14—C13—H13	119.8
C4—C5—H5	120.5	C13—C14—C15	119.74 (13)
C6—C5—H5	120.5	C13—C14—H14	120.1
C5—C6—C1	120.82 (12)	C15—C14—H14	120.1
C5—C6—H6	119.6	O2—C15—C14	124.01 (12)
C1—C6—H6	119.6	O2—C15—C10	115.27 (11)
O1—C7—C8	122.06 (12)	C14—C15—C10	120.73 (12)
O1—C7—C1	119.67 (12)	O2—C16—H16A	109.5
C8—C7—C1	118.20 (11)	O2—C16—H16B	109.5
C9—C8—C7	120.98 (12)	H16A—C16—H16B	109.5
C9—C8—H8	119.5	O2—C16—H16C	109.5
C7—C8—H8	119.5	H16A—C16—H16C	109.5
C8—C9—C10	127.46 (12)	H16B—C16—H16C	109.5
C6—C1—C2—C3	2.17 (18)	C7—C8—C9—C10	174.50 (12)
C7—C1—C2—C3	−177.12 (11)	C8—C9—C10—C11	−1.3 (2)
C1—C2—C3—C4	−0.75 (18)	C8—C9—C10—C15	179.82 (12)
C2—C3—C4—C5	−1.24 (18)	C15—C10—C11—C12	0.01 (19)
C2—C3—C4—Br1	176.31 (9)	C9—C10—C11—C12	−178.89 (13)
C3—C4—C5—C6	1.73 (18)	C10—C11—C12—C13	−0.1 (2)
Br1—C4—C5—C6	−175.85 (9)	C11—C12—C13—C14	0.2 (2)
C4—C5—C6—C1	−0.24 (18)	C12—C13—C14—C15	−0.2 (2)
C2—C1—C6—C5	−1.67 (18)	C16—O2—C15—C14	−2.45 (19)
C7—C1—C6—C5	177.60 (11)	C16—O2—C15—C10	177.64 (11)
C6—C1—C7—O1	164.07 (13)	C13—C14—C15—O2	−179.85 (12)
C2—C1—C7—O1	−16.66 (18)	C13—C14—C15—C10	0.06 (19)
C6—C1—C7—C8	−18.73 (18)	C11—C10—C15—O2	179.93 (11)
C2—C1—C7—C8	160.54 (11)	C9—C10—C15—O2	−1.13 (17)
O1—C7—C8—C9	1.3 (2)	C11—C10—C15—C14	0.01 (18)
C1—C7—C8—C9	−175.87 (12)	C9—C10—C15—C14	178.95 (11)