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

The mol-ecular structure of the title compound, C(17)H(15)BrO(3), consists of a bromo-phenyl and a 3,4-dimeth-oxy-phenyl group linked through a prop-2-en-1-one spacer. The C=C double bond displays an E conformation, while the carbonyl group shows an S-cis conformation relative to the double bond.

Related literature

For the Suzuki reaction, see: Miyaura & Suzuki (1995 ▶); Bringmann et al. (2005 ▶). For bichalcone derivatives, see: Shetonde et al. (2010 ▶). For related structures, see: Escobar et al. (2008 ▶); Valdebenito et al. (2010 ▶); Chu et al. (2004 ▶); Radha Krishna et al. (2005 ▶); Wu et al. (2005 ▶).

Experimental

Crystal data

C17H15BrO3

M = 347.20

Monoclinic,

a = 12.7946 (5) Å

b = 3.9373 (1) Å

c = 29.8209 (10) Å

β = 109.219 (3)°

V = 1418.54 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.91 mm−1

T = 120 K

0.2 × 0.12 × 0.08 mm

Data collection

Agilent Xcalibur Sapphire3 Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.802, T max = 1.000

12861 measured reflections

3429 independent reflections

2895 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.074

S = 1.10

3429 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006836/fj2515sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006836/fj2515Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006836/fj2515Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812006836/fj2515Isup4.cml

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

C17H15BrO3	F(000) = 704
Mr = 347.20	Dx = 1.626 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
a = 12.7946 (5) Å	Cell parameters from 3587 reflections
b = 3.9373 (1) Å	θ = 2.6–29.0°
c = 29.8209 (10) Å	µ = 2.91 mm−1
β = 109.219 (3)°	T = 120 K
V = 1418.54 (8) Å3	Prism, colourless
Z = 4	0.2 × 0.12 × 0.08 mm

Agilent Xcalibur Sapphire3 Gemini ultra diffractometer	3429 independent reflections
Radiation source: Enhance (Mo) X-ray source	2895 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 16.1511 pixels mm-1	θmax = 29.0°, θmin = 2.6°
ω scans	h = −17→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −5→5
Tmin = 0.802, Tmax = 1.000	l = −40→40
12861 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.019P)2 + 1.5139P] where P = (Fo2 + 2Fc2)/3
3429 reflections	(Δ/σ)max = 0.002
192 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	−0.11568 (2)	0.90741 (7)	0.528213 (9)	0.01853 (9)
O1	−0.25274 (14)	0.3062 (5)	0.31571 (6)	0.0198 (4)
O2	0.40922 (14)	0.3072 (5)	0.32327 (6)	0.0173 (4)
O3	0.37580 (14)	0.5457 (5)	0.39741 (6)	0.0190 (4)
C16	0.4322 (2)	0.1612 (7)	0.28340 (10)	0.0205 (6)
H16A	0.3873	0.2751	0.2542	0.031*
H16B	0.4141	−0.0814	0.2813	0.031*
H16C	0.5109	0.1902	0.2874	0.031*
C9	−0.0247 (2)	0.2800 (7)	0.32953 (9)	0.0143 (5)
H9	−0.0759	0.1507	0.3052	0.017*
C11	0.1119 (2)	0.1273 (6)	0.29162 (9)	0.0143 (5)
H11	0.0535	0.0184	0.2676	0.017*
C12	0.2171 (2)	0.1330 (6)	0.28749 (9)	0.0148 (5)
H12	0.2298	0.0357	0.2606	0.018*
C14	0.2834 (2)	0.4212 (7)	0.36346 (9)	0.0143 (5)
C1	−0.2297 (2)	0.6078 (7)	0.38681 (9)	0.0140 (5)
C15	0.1780 (2)	0.4234 (7)	0.36627 (9)	0.0144 (5)
H15	0.1649	0.5243	0.3928	0.017*
C5	−0.3827 (2)	0.8723 (7)	0.40364 (10)	0.0201 (6)
H5	−0.4579	0.9429	0.3932	0.024*
C10	0.0897 (2)	0.2760 (6)	0.32972 (9)	0.0130 (5)
C3	−0.2072 (2)	0.8273 (6)	0.46427 (9)	0.0142 (5)
C4	−0.3163 (2)	0.9344 (7)	0.45004 (10)	0.0178 (6)
H4	−0.3450	1.0479	0.4716	0.021*
C8	−0.0668 (2)	0.4429 (7)	0.35928 (9)	0.0149 (5)
H8	−0.0187	0.5619	0.3858	0.018*
C2	−0.1622 (2)	0.6663 (6)	0.43363 (9)	0.0135 (5)
H2	−0.0869	0.5968	0.4442	0.016*
C13	0.3031 (2)	0.2829 (6)	0.32325 (9)	0.0138 (5)
C7	−0.1871 (2)	0.4390 (7)	0.35127 (9)	0.0143 (5)
C17	0.3612 (2)	0.6874 (7)	0.43882 (9)	0.0212 (6)
H17A	0.3096	0.8790	0.4298	0.032*
H17B	0.4327	0.7667	0.4604	0.032*
H17C	0.3313	0.5140	0.4548	0.032*
C6	−0.3401 (2)	0.7083 (7)	0.37247 (10)	0.0175 (6)
H6	−0.3866	0.6638	0.3409	0.021*

	U11	U22	U33	U12	U13	U23
Br1	0.02037 (14)	0.02143 (14)	0.01387 (14)	−0.00093 (12)	0.00574 (10)	−0.00270 (12)
O1	0.0164 (9)	0.0267 (11)	0.0153 (10)	−0.0041 (8)	0.0037 (8)	−0.0030 (8)
O2	0.0138 (9)	0.0241 (10)	0.0154 (10)	0.0002 (8)	0.0068 (7)	−0.0033 (8)
O3	0.0141 (9)	0.0302 (11)	0.0126 (10)	−0.0035 (8)	0.0042 (7)	−0.0081 (9)
C16	0.0222 (14)	0.0244 (15)	0.0198 (15)	0.0009 (12)	0.0138 (12)	−0.0032 (12)
C9	0.0151 (13)	0.0143 (12)	0.0115 (13)	−0.0014 (11)	0.0017 (10)	0.0032 (11)
C11	0.0151 (12)	0.0144 (13)	0.0115 (13)	0.0002 (10)	0.0018 (10)	0.0005 (11)
C12	0.0198 (13)	0.0146 (13)	0.0115 (13)	0.0031 (11)	0.0073 (10)	−0.0011 (11)
C14	0.0173 (12)	0.0132 (12)	0.0113 (13)	−0.0004 (11)	0.0030 (10)	−0.0002 (11)
C1	0.0150 (12)	0.0128 (12)	0.0148 (13)	−0.0034 (11)	0.0058 (10)	0.0026 (11)
C15	0.0190 (13)	0.0143 (12)	0.0111 (13)	0.0019 (11)	0.0065 (10)	−0.0001 (11)
C5	0.0137 (13)	0.0235 (15)	0.0237 (15)	0.0011 (11)	0.0071 (11)	0.0050 (13)
C10	0.0150 (12)	0.0115 (12)	0.0126 (13)	0.0025 (10)	0.0048 (10)	0.0031 (10)
C3	0.0156 (12)	0.0133 (13)	0.0131 (14)	−0.0031 (10)	0.0039 (10)	0.0019 (10)
C4	0.0168 (13)	0.0176 (13)	0.0217 (15)	0.0010 (11)	0.0102 (11)	−0.0001 (12)
C8	0.0146 (12)	0.0164 (13)	0.0128 (13)	−0.0009 (11)	0.0033 (10)	0.0017 (11)
C2	0.0104 (12)	0.0140 (13)	0.0174 (14)	−0.0024 (10)	0.0064 (10)	0.0030 (11)
C13	0.0141 (12)	0.0135 (12)	0.0141 (13)	0.0016 (10)	0.0052 (10)	0.0031 (11)
C7	0.0155 (12)	0.0124 (12)	0.0141 (13)	−0.0005 (11)	0.0036 (10)	0.0036 (11)
C17	0.0201 (14)	0.0285 (16)	0.0147 (14)	−0.0036 (12)	0.0054 (11)	−0.0065 (12)
C6	0.0159 (13)	0.0203 (14)	0.0141 (14)	−0.0026 (11)	0.0019 (10)	0.0025 (11)

Br1—C3	1.907 (3)	C1—C2	1.398 (3)
O1—C7	1.232 (3)	C1—C7	1.498 (4)
O2—C16	1.436 (3)	C1—C6	1.391 (4)
O2—C13	1.361 (3)	C15—H15	0.9500
O3—C14	1.369 (3)	C15—C10	1.411 (3)
O3—C17	1.422 (3)	C5—H5	0.9500
C16—H16A	0.9800	C5—C4	1.387 (4)
C16—H16B	0.9800	C5—C6	1.383 (4)
C16—H16C	0.9800	C3—C4	1.384 (4)
C9—H9	0.9500	C3—C2	1.384 (4)
C9—C10	1.462 (3)	C4—H4	0.9500
C9—C8	1.343 (4)	C8—H8	0.9500
C11—H11	0.9500	C8—C7	1.477 (3)
C11—C12	1.391 (3)	C2—H2	0.9500
C11—C10	1.388 (3)	C17—H17A	0.9800
C12—H12	0.9500	C17—H17B	0.9800
C12—C13	1.387 (3)	C17—H17C	0.9800
C14—C15	1.379 (3)	C6—H6	0.9500
C14—C13	1.413 (4)
C13—O2—C16	116.6 (2)	C11—C10—C15	118.5 (2)
C14—O3—C17	117.0 (2)	C15—C10—C9	123.0 (2)
O2—C16—H16A	109.5	C4—C3—Br1	118.8 (2)
O2—C16—H16B	109.5	C2—C3—Br1	118.96 (19)
O2—C16—H16C	109.5	C2—C3—C4	122.3 (2)
H16A—C16—H16B	109.5	C5—C4—H4	120.7
H16A—C16—H16C	109.5	C3—C4—C5	118.5 (2)
H16B—C16—H16C	109.5	C3—C4—H4	120.7
C10—C9—H9	115.8	C9—C8—H8	119.6
C8—C9—H9	115.8	C9—C8—C7	120.8 (2)
C8—C9—C10	128.5 (2)	C7—C8—H8	119.6
C12—C11—H11	119.0	C1—C2—H2	120.7
C10—C11—H11	119.0	C3—C2—C1	118.7 (2)
C10—C11—C12	122.0 (2)	C3—C2—H2	120.7
C11—C12—H12	120.5	O2—C13—C12	124.7 (2)
C13—C12—C11	119.0 (2)	O2—C13—C14	115.4 (2)
C13—C12—H12	120.5	C12—C13—C14	119.9 (2)
O3—C14—C15	125.2 (2)	O1—C7—C1	119.5 (2)
O3—C14—C13	114.5 (2)	O1—C7—C8	121.5 (2)
C15—C14—C13	120.3 (2)	C8—C7—C1	118.9 (2)
C2—C1—C7	122.0 (2)	O3—C17—H17A	109.5
C6—C1—C2	119.4 (2)	O3—C17—H17B	109.5
C6—C1—C7	118.6 (2)	O3—C17—H17C	109.5
C14—C15—H15	119.9	H17A—C17—H17B	109.5
C14—C15—C10	120.1 (2)	H17A—C17—H17C	109.5
C10—C15—H15	119.9	H17B—C17—H17C	109.5
C4—C5—H5	119.8	C1—C6—H6	119.6
C6—C5—H5	119.8	C5—C6—C1	120.7 (2)
C6—C5—C4	120.3 (2)	C5—C6—H6	119.6
C11—C10—C9	118.4 (2)
Br1—C3—C4—C5	−179.3 (2)	C10—C11—C12—C13	2.0 (4)
Br1—C3—C2—C1	179.90 (18)	C4—C5—C6—C1	−1.0 (4)
O3—C14—C15—C10	−177.6 (2)	C4—C3—C2—C1	−0.5 (4)
O3—C14—C13—O2	−2.7 (3)	C8—C9—C10—C11	−171.3 (3)
O3—C14—C13—C12	176.7 (2)	C8—C9—C10—C15	7.1 (4)
C16—O2—C13—C12	−0.9 (4)	C2—C1—C7—O1	159.4 (2)
C16—O2—C13—C14	178.5 (2)	C2—C1—C7—C8	−22.0 (4)
C9—C8—C7—O1	−4.7 (4)	C2—C1—C6—C5	1.6 (4)
C9—C8—C7—C1	176.7 (2)	C2—C3—C4—C5	1.1 (4)
C11—C12—C13—O2	−179.5 (2)	C13—C14—C15—C10	2.3 (4)
C11—C12—C13—C14	1.1 (4)	C7—C1—C2—C3	179.2 (2)
C12—C11—C10—C9	175.6 (2)	C7—C1—C6—C5	−178.5 (2)
C12—C11—C10—C15	−2.9 (4)	C17—O3—C14—C15	0.2 (4)
C14—C15—C10—C9	−177.7 (2)	C17—O3—C14—C13	−179.8 (2)
C14—C15—C10—C11	0.7 (4)	C6—C1—C2—C3	−0.8 (4)
C15—C14—C13—O2	177.3 (2)	C6—C1—C7—O1	−20.6 (4)
C15—C14—C13—C12	−3.3 (4)	C6—C1—C7—C8	158.1 (2)
C10—C9—C8—C7	175.1 (2)	C6—C5—C4—C3	−0.3 (4)