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

The title compound, C(17)H(15)BrO(2), adopts an E configuration. The dihedral angle between the two benzene rings is 10.09 (11)°. The enone plane makes dihedral angles of 12.05 (11) and 9.87 (11)°, respectively, with the bromo-phenyl and ethoxy-phenyl rings. The eth-oxy group is nearly coplanar with the attached benzene ring. In the crystal structure, the mol-ecules are linked by C-H⋯O hydrogen bonds, forming a zigzag ribbon-like structure along the b-axis direction.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Patil, Fun et al. (2007 ▶); Patil, Ng et al. (2007 ▶); Sathiya Moorthi et al. (2005a ▶,b ▶). For background to chalcones, see: Chopra et al. (2007 ▶); DiCesare et al. (2000 ▶); Gu et al. (2008a ▶,b ▶); Jiang et al. (1994 ▶); Lokaj et al. (2001 ▶); Low et al. (2002 ▶); Nel et al. (1998 ▶); Patil & Dharmaprakash (2007 ▶); Patil et al. (2006 ▶); Schmalle et al. (1990 ▶); Wang et al. (2004 ▶).

Experimental

Crystal data

C17H15BrO2

M = 331.19

Monoclinic,

a = 4.0516 (1) Å

b = 9.6501 (2) Å

c = 17.9120 (4) Å

β = 92.396 (1)°

V = 699.72 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.94 mm−1

T = 100.0 (1) K

0.53 × 0.31 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.305, T max = 0.641 (expected range = 0.289–0.607)

14837 measured reflections

5989 independent reflections

4682 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.04

5989 reflections

182 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.65 e Å−3

Absolute structure: Flack (1983 ▶), 2764 Friedel pairs

Flack parameter: 0.021 (8)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018850/ci2619sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018850/ci2619Isup2.hkl

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

C17H15BrO2	F000 = 336
Mr = 331.19	Dx = 1.572 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5989 reflections
a = 4.0516 (1) Å	θ = 1.1–35.0º
b = 9.6501 (2) Å	µ = 2.94 mm−1
c = 17.9120 (4) Å	T = 100.0 (1) K
β = 92.396 (1)º	Block, colourless
V = 699.72 (3) Å3	0.53 × 0.31 × 0.17 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	5989 independent reflections
Radiation source: fine-focus sealed tube	4682 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
Detector resolution: 8.33 pixels mm-1	θmax = 35.0º
T = 100.0(1) K	θmin = 1.1º
ω scans	h = −6→6
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.305, Tmax = 0.642	l = −28→23
14837 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0372P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.093	(Δ/σ)max = 0.002
S = 1.04	Δρmax = 0.69 e Å−3
5989 reflections	Δρmin = −0.65 e Å−3
182 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 2764 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.021 (8)
Secondary atom site location: difference Fourier map

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.44099 (5)	0.22151 (3)	0.509606 (11)	0.02359 (7)
O1	0.6257 (5)	0.16393 (19)	0.80200 (10)	0.0229 (4)
O2	0.0554 (4)	0.29630 (17)	1.23694 (9)	0.0191 (3)
C1	0.4078 (6)	0.2599 (2)	0.66571 (13)	0.0179 (4)
H1A	0.5320	0.1789	0.6686	0.021*
C2	0.3124 (6)	0.3148 (2)	0.59698 (13)	0.0174 (4)
C3	0.1291 (6)	0.4369 (2)	0.59085 (14)	0.0194 (4)
H3A	0.0668	0.4731	0.5443	0.023*
C4	0.0418 (6)	0.5031 (2)	0.65597 (14)	0.0194 (4)
H4A	−0.0799	0.5848	0.6528	0.023*
C5	0.1332 (6)	0.4494 (2)	0.72574 (14)	0.0173 (4)
H5A	0.0725	0.4948	0.7689	0.021*
C6	0.3170 (6)	0.3266 (2)	0.73090 (13)	0.0155 (4)
C7	0.4277 (6)	0.2592 (2)	0.80334 (13)	0.0163 (4)
C8	0.2936 (6)	0.3067 (2)	0.87445 (13)	0.0170 (4)
H8A	0.1488	0.3814	0.8756	0.020*
C9	0.3862 (5)	0.2391 (3)	0.93731 (12)	0.0162 (4)
H9A	0.5380	0.1681	0.9313	0.019*
C10	0.2857 (6)	0.2599 (2)	1.01363 (13)	0.0161 (4)
C11	0.0989 (6)	0.3739 (2)	1.03642 (13)	0.0165 (4)
H11A	0.0263	0.4389	1.0011	0.020*
C12	0.0207 (6)	0.3914 (2)	1.11050 (13)	0.0171 (4)
H12A	−0.0990	0.4684	1.1249	0.020*
C13	0.1238 (6)	0.2920 (2)	1.16333 (13)	0.0156 (4)
C14	0.3094 (6)	0.1789 (2)	1.14161 (13)	0.0169 (4)
H14A	0.3792	0.1131	1.1768	0.020*
C15	0.3906 (6)	0.1639 (2)	1.06790 (13)	0.0166 (4)
H15A	0.5173	0.0884	1.0542	0.020*
C16	−0.1265 (6)	0.4130 (3)	1.26362 (14)	0.0194 (5)
H16A	−0.3355	0.4225	1.2356	0.023*
H16B	−0.0010	0.4978	1.2584	0.023*
C17	−0.1832 (9)	0.3845 (3)	1.34460 (16)	0.0323 (7)
H17C	−0.3014	0.4605	1.3654	0.048*
H17A	0.0256	0.3736	1.3713	0.048*
H17B	−0.3101	0.3010	1.3488	0.048*

	U11	U22	U33	U12	U13	U23
Br1	0.02512 (11)	0.03165 (12)	0.01422 (9)	−0.00028 (13)	0.00341 (7)	−0.00396 (12)
O1	0.0289 (10)	0.0226 (8)	0.0170 (8)	0.0094 (7)	0.0001 (7)	0.0002 (7)
O2	0.0236 (9)	0.0196 (8)	0.0144 (8)	0.0049 (7)	0.0052 (6)	0.0037 (6)
C1	0.0184 (10)	0.0188 (10)	0.0165 (10)	−0.0003 (7)	0.0022 (8)	0.0009 (7)
C2	0.0153 (10)	0.0197 (10)	0.0173 (11)	−0.0035 (8)	0.0026 (8)	−0.0029 (8)
C3	0.0210 (11)	0.0199 (10)	0.0175 (11)	−0.0043 (9)	0.0006 (8)	0.0042 (9)
C4	0.0200 (12)	0.0149 (10)	0.0231 (12)	−0.0007 (9)	−0.0016 (9)	0.0017 (9)
C5	0.0201 (11)	0.0150 (10)	0.0166 (11)	−0.0017 (8)	0.0004 (8)	−0.0012 (8)
C6	0.0186 (10)	0.0132 (9)	0.0147 (10)	−0.0024 (8)	0.0011 (8)	−0.0004 (7)
C7	0.0179 (10)	0.0145 (9)	0.0164 (10)	−0.0011 (7)	0.0004 (8)	−0.0020 (7)
C8	0.0190 (11)	0.0168 (10)	0.0151 (10)	0.0003 (8)	0.0006 (8)	−0.0025 (8)
C9	0.0176 (9)	0.0141 (12)	0.0168 (9)	−0.0005 (8)	0.0007 (7)	−0.0023 (8)
C10	0.0172 (10)	0.0142 (9)	0.0170 (10)	−0.0027 (7)	0.0009 (8)	−0.0001 (7)
C11	0.0179 (10)	0.0150 (9)	0.0165 (10)	−0.0013 (8)	−0.0008 (8)	0.0028 (8)
C12	0.0189 (11)	0.0147 (9)	0.0176 (11)	−0.0013 (8)	0.0013 (8)	0.0003 (8)
C13	0.0144 (10)	0.0161 (10)	0.0166 (10)	−0.0015 (8)	0.0036 (8)	0.0004 (8)
C14	0.0184 (11)	0.0136 (8)	0.0186 (11)	0.0009 (7)	0.0005 (8)	0.0043 (7)
C15	0.0161 (10)	0.0150 (9)	0.0188 (11)	0.0007 (8)	0.0011 (8)	0.0004 (8)
C16	0.0232 (12)	0.0161 (10)	0.0194 (11)	−0.0015 (8)	0.0060 (9)	−0.0003 (8)
C17	0.0467 (19)	0.0282 (13)	0.0230 (14)	0.0146 (13)	0.0146 (12)	0.0044 (11)

Br1—C2	1.897 (2)	C9—C10	1.457 (3)
O1—C7	1.221 (3)	C9—H9A	0.93
O2—C13	1.359 (3)	C10—C15	1.397 (3)
O2—C16	1.439 (3)	C10—C11	1.405 (3)
C1—C2	1.381 (3)	C11—C12	1.387 (3)
C1—C6	1.396 (3)	C11—H11A	0.93
C1—H1A	0.93	C12—C13	1.399 (3)
C2—C3	1.394 (3)	C12—H12A	0.93
C3—C4	1.389 (3)	C13—C14	1.390 (3)
C3—H3A	0.93	C14—C15	1.381 (3)
C4—C5	1.389 (4)	C14—H14A	0.93
C4—H4A	0.93	C15—H15A	0.93
C5—C6	1.401 (3)	C16—C17	1.504 (4)
C5—H5A	0.93	C16—H16A	0.97
C6—C7	1.503 (3)	C16—H16B	0.97
C7—C8	1.478 (3)	C17—H17C	0.96
C8—C9	1.341 (3)	C17—H17A	0.96
C8—H8A	0.93	C17—H17B	0.96
C13—O2—C16	118.31 (18)	C15—C10—C9	118.2 (2)
C2—C1—C6	119.7 (2)	C11—C10—C9	123.8 (2)
C2—C1—H1A	120.2	C12—C11—C10	121.4 (2)
C6—C1—H1A	120.2	C12—C11—H11A	119.3
C1—C2—C3	121.5 (2)	C10—C11—H11A	119.3
C1—C2—Br1	118.50 (18)	C11—C12—C13	119.3 (2)
C3—C2—Br1	119.98 (18)	C11—C12—H12A	120.3
C4—C3—C2	118.4 (2)	C13—C12—H12A	120.3
C4—C3—H3A	120.8	O2—C13—C14	115.5 (2)
C2—C3—H3A	120.8	O2—C13—C12	124.6 (2)
C3—C4—C5	121.1 (2)	C14—C13—C12	119.9 (2)
C3—C4—H4A	119.5	C15—C14—C13	120.2 (2)
C5—C4—H4A	119.5	C15—C14—H14A	119.9
C4—C5—C6	119.7 (2)	C13—C14—H14A	119.9
C4—C5—H5A	120.1	C14—C15—C10	121.2 (2)
C6—C5—H5A	120.1	C14—C15—H15A	119.4
C1—C6—C5	119.5 (2)	C10—C15—H15A	119.4
C1—C6—C7	116.3 (2)	O2—C16—C17	106.1 (2)
C5—C6—C7	124.2 (2)	O2—C16—H16A	110.5
O1—C7—C8	121.0 (2)	C17—C16—H16A	110.5
O1—C7—C6	118.8 (2)	O2—C16—H16B	110.5
C8—C7—C6	120.19 (19)	C17—C16—H16B	110.5
C9—C8—C7	118.2 (2)	H16A—C16—H16B	108.7
C9—C8—H8A	120.9	C16—C17—H17C	109.5
C7—C8—H8A	120.9	C16—C17—H17A	109.5
C8—C9—C10	129.9 (2)	H17C—C17—H17A	109.5
C8—C9—H9A	115.0	C16—C17—H17B	109.5
C10—C9—H9A	115.0	H17C—C17—H17B	109.5
C15—C10—C11	118.0 (2)	H17A—C17—H17B	109.5
C6—C1—C2—C3	0.7 (4)	C7—C8—C9—C10	−177.6 (2)
C6—C1—C2—Br1	179.90 (17)	C8—C9—C10—C15	172.5 (3)
C1—C2—C3—C4	−0.2 (4)	C8—C9—C10—C11	−9.9 (4)
Br1—C2—C3—C4	−179.42 (18)	C15—C10—C11—C12	0.2 (3)
C2—C3—C4—C5	−0.2 (4)	C9—C10—C11—C12	−177.5 (2)
C3—C4—C5—C6	0.1 (4)	C10—C11—C12—C13	−1.4 (4)
C2—C1—C6—C5	−0.7 (3)	C16—O2—C13—C14	178.0 (2)
C2—C1—C6—C7	179.4 (2)	C16—O2—C13—C12	−2.1 (3)
C4—C5—C6—C1	0.3 (3)	C11—C12—C13—O2	−178.4 (2)
C4—C5—C6—C7	−179.8 (2)	C11—C12—C13—C14	1.5 (3)
C1—C6—C7—O1	10.3 (3)	O2—C13—C14—C15	179.5 (2)
C5—C6—C7—O1	−169.6 (2)	C12—C13—C14—C15	−0.4 (3)
C1—C6—C7—C8	−168.7 (2)	C13—C14—C15—C10	−0.8 (4)
C5—C6—C7—C8	11.4 (3)	C11—C10—C15—C14	1.0 (3)
O1—C7—C8—C9	−2.3 (3)	C9—C10—C15—C14	178.7 (2)
C6—C7—C8—C9	176.7 (2)	C13—O2—C16—C17	176.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.93	2.36	2.746 (3)	105
C16—H16B···O1i	0.97	2.49	3.400 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1	0.93	2.36	2.746 (3)	105
C16—H16B⋯O1i	0.97	2.49	3.400 (3)	157

Symmetry code: (i) .