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

The title compound, C(17)H(15)BrO(2), consists of two substituted benzene rings connected by a prop-2-en-1-one group. The mol-ecule is nearly planar and adopts an E configuration. The dihedral angle between the two benzene rings is 8.51 (19)°. The enone plane makes dihedral angles of 11.06 (19) and 7.69 (19)°, respectively, with the bromo-phenyl and ethoxy-phenyl rings. The mol-ecules are linked by C-H⋯O hydrogen bonds to form a zigzag ribbon-like structure along the b direction. The crystal structure is stabilized by weak intra- and inter-molecular C-H⋯O inter-actions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For similar structures, see: Fun et al. (2008 ▶); Patil, Fun et al. (2007 ▶); Patil, Ng et al. (2007 ▶). For background on chalcones, see: Chopra et al. (2007 ▶); Fichou et al. (1988 ▶); Goto et al. (1991 ▶); Gu, Ji, Patil & Dharmaprakash (2008 ▶); Gu, Ji, Patil, Dharmaprakash & Wang (2008 ▶); Sathiya Moorthi, Chinnakali, Nanjundan, Radhika et al. (2005 ▶); Sathiya Moorthi, Chinnakali, Nanjundan, Selvam et al. (2005 ▶); Schmalle et al. (1990 ▶); Uchida et al. (1998 ▶); Wang et al. (2004 ▶); Zhao et al. (2000 ▶).

Experimental

Crystal data

C17H15BrO2

M = 331.19

Monoclinic,

a = 3.9855 (1) Å

b = 10.0681 (3) Å

c = 17.5270 (4) Å

β = 92.227 (2)°

V = 702.77 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.92 mm−1

T = 100.0 (1) K

0.47 × 0.17 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.340, T max = 0.781

7696 measured reflections

2620 independent reflections

2339 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.095

S = 1.08

2620 reflections

182 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.98 e Å−3

Δρmin = −0.53 e Å−3

Absolute structure: Flack (1983 ▶), 656 Friedel pairs

Flack parameter: 0.013 (13)

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/S1600536808021776/fl2206sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021776/fl2206Isup2.hkl

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

C17H15BrO2	F000 = 336
Mr = 331.19	Dx = 1.565 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2620 reflections
a = 3.9855 (1) Å	θ = 1.2–29.0º
b = 10.0681 (3) Å	µ = 2.92 mm−1
c = 17.5270 (4) Å	T = 100.0 (1) K
β = 92.227 (2)º	Block, colorless
V = 702.77 (3) Å3	0.47 × 0.17 × 0.09 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	2620 independent reflections
Radiation source: fine-focus sealed tube	2339 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
Detector resolution: 8.33 pixels mm-1	θmax = 29.0º
T = 100.0(1) K	θmin = 1.2º
ω scans	h = −5→5
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −13→8
Tmin = 0.340, Tmax = 0.781	l = −23→23
7696 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033	w = 1/[σ2(Fo2) + (0.0562P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.095	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.98 e Å−3
2620 reflections	Δρmin = −0.53 e Å−3
182 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 640 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.013 (13)
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	0.43528 (8)	0.23538 (6)	0.502628 (18)	0.02637 (12)
O1	−0.1514 (7)	0.6546 (3)	0.77360 (17)	0.0282 (7)
O2	0.5201 (7)	0.5258 (3)	1.22900 (16)	0.0234 (6)
C1	0.0563 (11)	0.5256 (4)	0.6436 (3)	0.0234 (9)
H1A	−0.0604	0.6052	0.6379	0.028*
C2	0.1400 (10)	0.4543 (4)	0.5789 (2)	0.0210 (8)
H2A	0.0835	0.4859	0.5302	0.025*
C3	0.3114 (9)	0.3340 (4)	0.5890 (2)	0.0195 (8)
C4	0.3966 (9)	0.2855 (4)	0.6611 (2)	0.0229 (8)
H4A	0.5097	0.2051	0.6669	0.027*
C5	0.3112 (10)	0.3583 (4)	0.7242 (2)	0.0216 (8)
H5A	0.3659	0.3258	0.7728	0.026*
C6	0.1443 (10)	0.4796 (4)	0.7165 (2)	0.0197 (8)
C7	0.0421 (11)	0.5603 (4)	0.7834 (2)	0.0241 (9)
C8	0.1824 (10)	0.5255 (5)	0.8602 (2)	0.0249 (9)
H8A	0.3356	0.4561	0.8655	0.030*
C9	0.0927 (10)	0.5921 (4)	0.9221 (2)	0.0236 (9)
H9A	−0.0626	0.6601	0.9142	0.028*
C10	0.2115 (10)	0.5700 (4)	1.0008 (2)	0.0219 (8)
C11	0.4006 (10)	0.4600 (4)	1.0240 (3)	0.0235 (9)
H11A	0.4597	0.3979	0.9876	0.028*
C12	0.5036 (10)	0.4399 (4)	1.0993 (2)	0.0241 (9)
H12A	0.6252	0.3643	1.1133	0.029*
C13	0.4243 (10)	0.5332 (4)	1.1541 (2)	0.0220 (8)
C14	0.2317 (10)	0.6439 (4)	1.1322 (2)	0.0228 (9)
H14A	0.1741	0.7059	1.1687	0.027*
C15	0.1258 (10)	0.6625 (4)	1.0569 (2)	0.0223 (8)
H15A	−0.0028	0.7365	1.0433	0.027*
C16	0.7128 (11)	0.4120 (4)	1.2541 (3)	0.0247 (9)
H16A	0.9075	0.4014	1.2231	0.030*
H16B	0.5773	0.3322	1.2495	0.030*
C17	0.8217 (13)	0.4350 (5)	1.3364 (3)	0.0328 (12)
H17A	0.9605	0.3625	1.3541	0.049*
H17B	0.6272	0.4407	1.3669	0.049*
H17C	0.9465	0.5163	1.3406	0.049*

	U11	U22	U33	U12	U13	U23
Br1	0.02618 (18)	0.0284 (2)	0.02459 (17)	−0.0013 (3)	0.00238 (12)	−0.0061 (2)
O1	0.0305 (16)	0.0211 (17)	0.0332 (16)	0.0038 (13)	0.0033 (13)	−0.0008 (13)
O2	0.0222 (14)	0.0203 (15)	0.0275 (14)	0.0029 (12)	−0.0015 (12)	−0.0018 (12)
C1	0.026 (2)	0.014 (2)	0.030 (2)	−0.0016 (19)	0.0027 (18)	0.0004 (18)
C2	0.0227 (19)	0.019 (2)	0.0218 (18)	−0.0029 (17)	0.0000 (15)	0.0045 (15)
C3	0.0184 (17)	0.017 (2)	0.0229 (18)	−0.0049 (15)	0.0036 (14)	−0.0029 (15)
C4	0.0199 (17)	0.0192 (18)	0.029 (2)	0.0005 (17)	−0.0002 (15)	0.0007 (17)
C5	0.0247 (19)	0.017 (2)	0.0226 (19)	−0.0001 (16)	−0.0030 (16)	0.0040 (16)
C6	0.021 (2)	0.0155 (18)	0.0222 (18)	−0.0033 (15)	0.0012 (16)	−0.0020 (17)
C7	0.026 (2)	0.020 (2)	0.027 (2)	−0.0048 (17)	0.0057 (17)	0.0006 (17)
C8	0.0225 (19)	0.020 (2)	0.032 (2)	0.0018 (17)	0.0013 (17)	0.0015 (18)
C9	0.0233 (19)	0.018 (2)	0.029 (2)	−0.0030 (17)	0.0013 (16)	−0.0010 (17)
C10	0.0191 (18)	0.018 (2)	0.029 (2)	−0.0054 (16)	0.0046 (15)	−0.0038 (16)
C11	0.023 (2)	0.016 (2)	0.032 (2)	−0.0033 (16)	0.0084 (16)	−0.0057 (16)
C12	0.0209 (19)	0.0152 (19)	0.036 (2)	0.0016 (17)	0.0035 (17)	−0.0028 (18)
C13	0.0178 (18)	0.0172 (19)	0.031 (2)	−0.0035 (16)	0.0026 (16)	−0.0046 (17)
C14	0.0220 (19)	0.0169 (19)	0.030 (2)	−0.0018 (16)	0.0029 (16)	−0.0068 (17)
C15	0.0201 (18)	0.017 (2)	0.030 (2)	−0.0004 (15)	0.0011 (16)	−0.0030 (16)
C16	0.024 (2)	0.013 (2)	0.037 (2)	−0.0003 (16)	−0.0013 (18)	0.0026 (18)
C17	0.032 (3)	0.025 (2)	0.042 (3)	−0.002 (2)	−0.003 (2)	0.008 (2)

Br1—C3	1.892 (4)	C9—C10	1.456 (6)
O1—C7	1.231 (5)	C9—H9A	0.9300
O2—C13	1.354 (5)	C10—C11	1.392 (6)
O2—C16	1.438 (5)	C10—C15	1.406 (6)
C1—C6	1.391 (6)	C11—C12	1.383 (6)
C1—C2	1.393 (6)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.389 (6)
C2—C3	1.399 (6)	C12—H12A	0.9300
C2—H2A	0.9300	C13—C14	1.399 (6)
C3—C4	1.385 (6)	C14—C15	1.383 (6)
C4—C5	1.381 (6)	C14—H14A	0.9300
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.395 (6)	C16—C17	1.508 (6)
C5—H5A	0.9300	C16—H16A	0.9700
C6—C7	1.496 (6)	C16—H16B	0.9700
C7—C8	1.480 (6)	C17—H17A	0.9600
C8—C9	1.336 (6)	C17—H17B	0.9600
C8—H8A	0.9300	C17—H17C	0.9600
C13—O2—C16	117.9 (3)	C11—C10—C9	123.4 (4)
C6—C1—C2	121.1 (4)	C15—C10—C9	118.8 (4)
C6—C1—H1A	119.5	C12—C11—C10	122.2 (4)
C2—C1—H1A	119.5	C12—C11—H11A	118.9
C1—C2—C3	118.3 (4)	C10—C11—H11A	118.9
C1—C2—H2A	120.8	C11—C12—C13	119.6 (4)
C3—C2—H2A	120.8	C11—C12—H12A	120.2
C4—C3—C2	121.5 (4)	C13—C12—H12A	120.2
C4—C3—Br1	118.9 (3)	O2—C13—C12	124.7 (4)
C2—C3—Br1	119.6 (3)	O2—C13—C14	116.2 (4)
C5—C4—C3	119.0 (4)	C12—C13—C14	119.1 (4)
C5—C4—H4A	120.5	C15—C14—C13	121.0 (4)
C3—C4—H4A	120.5	C15—C14—H14A	119.5
C4—C5—C6	121.2 (4)	C13—C14—H14A	119.5
C4—C5—H5A	119.4	C14—C15—C10	120.3 (4)
C6—C5—H5A	119.4	C14—C15—H15A	119.8
C1—C6—C5	118.9 (4)	C10—C15—H15A	119.8
C1—C6—C7	118.2 (4)	O2—C16—C17	107.5 (4)
C5—C6—C7	122.8 (4)	O2—C16—H16A	110.2
O1—C7—C8	121.5 (4)	C17—C16—H16A	110.2
O1—C7—C6	119.8 (4)	O2—C16—H16B	110.2
C8—C7—C6	118.7 (4)	C17—C16—H16B	110.2
C9—C8—C7	121.1 (4)	H16A—C16—H16B	108.5
C9—C8—H8A	119.4	C16—C17—H17A	109.5
C7—C8—H8A	119.4	C16—C17—H17B	109.5
C8—C9—C10	127.2 (4)	H17A—C17—H17B	109.5
C8—C9—H9A	116.4	C16—C17—H17C	109.5
C10—C9—H9A	116.4	H17A—C17—H17C	109.5
C11—C10—C15	117.8 (4)	H17B—C17—H17C	109.5
C6—C1—C2—C3	0.9 (6)	C7—C8—C9—C10	−179.4 (4)
C1—C2—C3—C4	0.2 (6)	C8—C9—C10—C11	−10.6 (7)
C1—C2—C3—Br1	−179.1 (3)	C8—C9—C10—C15	170.8 (4)
C2—C3—C4—C5	−0.3 (6)	C15—C10—C11—C12	0.1 (6)
Br1—C3—C4—C5	179.0 (3)	C9—C10—C11—C12	−178.5 (4)
C3—C4—C5—C6	−0.6 (6)	C10—C11—C12—C13	−1.5 (6)
C2—C1—C6—C5	−1.8 (6)	C16—O2—C13—C12	−1.2 (6)
C2—C1—C6—C7	−179.2 (4)	C16—O2—C13—C14	178.8 (3)
C4—C5—C6—C1	1.6 (6)	C11—C12—C13—O2	−178.0 (4)
C4—C5—C6—C7	178.9 (4)	C11—C12—C13—C14	2.1 (6)
C1—C6—C7—O1	9.3 (6)	O2—C13—C14—C15	178.8 (4)
C5—C6—C7—O1	−168.0 (4)	C12—C13—C14—C15	−1.2 (6)
C1—C6—C7—C8	−169.7 (4)	C13—C14—C15—C10	−0.2 (6)
C5—C6—C7—C8	13.0 (6)	C11—C10—C15—C14	0.8 (6)
O1—C7—C8—C9	2.8 (7)	C9—C10—C15—C14	179.4 (4)
C6—C7—C8—C9	−178.3 (4)	C13—O2—C16—C17	173.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O2i	0.93	2.57	3.257 (5)	131
C9—H9A···O1	0.93	2.48	2.814 (5)	102
C16—H16B···O1ii	0.97	2.49	3.446 (5)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O2i	0.93	2.57	3.257 (5)	131
C9—H9A⋯O1	0.93	2.48	2.814 (5)	102
C16—H16B⋯O1ii	0.97	2.49	3.446 (5)	170

Symmetry codes: (i) ; (ii) .