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

In the title compound, C(16)H(13)BrO(2), two benzene rings form a dihedral angle of 44.3 (9)°. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains propagating in [010]. The crystal packing also exhibits short Br⋯Br contacts of 3.4787 (8) Å. A comparison of the DFT-optimized gas-phase mol-ecular geometry with that in the crystal structure revealed only small differences.

Related literature

For the radical quenching properties of included phenol groups, see: Dhar (1981 ▶). For related structures, see: Arai et al. (1994 ▶); Li et al. (1992 ▶); Patil et al. (2007 ▶); Shettigar et al. (2006 ▶). For standard bond lengths, see Allen et al. (1987 ▶). For density functional theory, see: Schmidt & Polik (2007 ▶); Hehre et al. (1986 ▶).

Experimental

Crystal data

C16H13BrO2

M = 317.17

Monoclinic,

a = 12.7300 (8) Å

b = 4.0061 (3) Å

c = 13.0035 (6) Å

β = 100.671 (5)°

V = 651.68 (7) Å3

Z = 2

Cu Kα radiation

μ = 4.25 mm−1

T = 110 K

0.48 × 0.41 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini Cu) detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.423, T max = 1.000

2117 measured reflections

1641 independent reflections

1621 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.091

S = 1.07

1641 reflections

173 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.65 e Å−3

Absolute structure: Flack (1983 ▶), 133 Friedel pairs

Flack parameter: 0.00 (3)

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I. DOI: 10.1107/S160053681002218X/cv2728sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002218X/cv2728Isup2.hkl

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

C16H13BrO2	F(000) = 320
Mr = 317.17	Dx = 1.616 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 1981 reflections
a = 12.7300 (8) Å	θ = 4.5–74.1°
b = 4.0061 (3) Å	µ = 4.25 mm−1
c = 13.0035 (6) Å	T = 110 K
β = 100.671 (5)°	Chunk, colourless
V = 651.68 (7) Å3	0.48 × 0.41 × 0.28 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini Cu) detector	1641 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1621 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 10.5081 pixels mm-1	θmax = 74.1°, θmin = 4.5°
ω scans	h = −9→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −2→4
Tmin = 0.423, Tmax = 1.000	l = −15→16
2117 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0718P)2 + 0.5775P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
1641 reflections	Δρmax = 0.71 e Å−3
173 parameters	Δρmin = −0.65 e Å−3
1 restraint	Absolute structure: Flack (1983), 133 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (3)

Experimental. IR data (KBr) ν cm-1: 2998 cm-1, 2937 cm-1, 2839 cm-1 (C—H al.str), 3058 cm-1 (C—H ar. str) 1646 cm-1 (C=O), 1580 cm-1 (C=C); 1245 cm-1 (C—O—C).

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
Br	0.38764 (3)	0.18817 (18)	0.46303 (2)	0.01538 (15)
O1	0.2178 (2)	0.2427 (10)	0.1406 (2)	0.0211 (8)
O2	0.8860 (2)	0.2977 (9)	0.1659 (2)	0.0209 (7)
C1	0.2190 (3)	0.4727 (13)	0.3077 (3)	0.0149 (9)
C2	0.2577 (3)	0.4233 (12)	0.4142 (3)	0.0119 (8)
C3	0.2022 (3)	0.5312 (12)	0.4896 (3)	0.0166 (9)
H3A	0.2299	0.4917	0.5616	0.020*
C4	0.1060 (3)	0.6971 (19)	0.4599 (3)	0.0223 (8)
H4A	0.0679	0.7740	0.5116	0.027*
C5	0.0651 (3)	0.7513 (12)	0.3545 (3)	0.0211 (11)
H5A	−0.0008	0.8660	0.3342	0.025*
C6	0.1203 (3)	0.6385 (14)	0.2797 (3)	0.0187 (10)
H6A	0.0913	0.6732	0.2078	0.022*
C7	0.2730 (3)	0.3590 (12)	0.2195 (3)	0.0173 (9)
C8	0.3891 (3)	0.4058 (13)	0.2303 (3)	0.0160 (9)
H8A	0.4255	0.5526	0.2824	0.019*
C9	0.4441 (3)	0.2431 (12)	0.1673 (3)	0.0161 (10)
H9A	0.4037	0.1037	0.1154	0.019*
C10	0.5595 (3)	0.2564 (10)	0.1697 (3)	0.0145 (11)
C11	0.5999 (3)	0.1064 (11)	0.0878 (3)	0.0164 (10)
H11A	0.5519	−0.0064	0.0344	0.020*
C12	0.7083 (3)	0.1171 (11)	0.0822 (3)	0.0155 (10)
H12A	0.7334	0.0191	0.0248	0.019*
C13	0.7787 (3)	0.2733 (11)	0.1619 (3)	0.0156 (10)
C14	0.7411 (4)	0.4183 (13)	0.2470 (3)	0.0186 (9)
H14A	0.7897	0.5209	0.3022	0.022*
C15	0.6327 (3)	0.4102 (13)	0.2495 (3)	0.0175 (9)
H15A	0.6075	0.5107	0.3065	0.021*
C16	0.9272 (3)	0.1512 (18)	0.0810 (3)	0.0223 (11)
H16A	0.9121	−0.0888	0.0783	0.033*
H16B	1.0046	0.1870	0.0916	0.033*
H16C	0.8930	0.2553	0.0151	0.033*

	U11	U22	U33	U12	U13	U23
Br	0.0159 (2)	0.0153 (2)	0.0148 (2)	−0.0005 (2)	0.00224 (13)	0.00195 (19)
O1	0.0204 (13)	0.028 (2)	0.0151 (11)	−0.0044 (15)	0.0031 (10)	−0.0034 (14)
O2	0.0169 (14)	0.027 (2)	0.0207 (14)	−0.0012 (13)	0.0070 (12)	−0.0027 (13)
C1	0.0154 (18)	0.016 (2)	0.0154 (17)	−0.0033 (18)	0.0081 (15)	−0.0001 (17)
C2	0.0083 (16)	0.008 (2)	0.0179 (17)	0.0027 (16)	−0.0026 (13)	0.0032 (17)
C3	0.021 (2)	0.014 (2)	0.0160 (18)	−0.0060 (18)	0.0067 (15)	−0.0023 (16)
C4	0.0242 (18)	0.018 (2)	0.0292 (19)	−0.004 (3)	0.0173 (15)	−0.006 (3)
C5	0.0136 (17)	0.016 (3)	0.034 (2)	0.0014 (18)	0.0047 (16)	0.0002 (19)
C6	0.0165 (17)	0.016 (3)	0.0228 (17)	−0.003 (2)	0.0023 (14)	0.0024 (19)
C7	0.023 (2)	0.015 (2)	0.0152 (18)	−0.0028 (19)	0.0061 (16)	0.0040 (17)
C8	0.0176 (19)	0.015 (3)	0.0155 (17)	−0.0006 (18)	0.0036 (14)	0.0011 (17)
C9	0.0189 (17)	0.016 (3)	0.0131 (15)	−0.0011 (18)	0.0025 (13)	0.0027 (18)
C10	0.0197 (18)	0.014 (3)	0.0113 (15)	0.0016 (17)	0.0058 (14)	0.0018 (15)
C11	0.0208 (19)	0.015 (3)	0.0135 (16)	0.0001 (17)	0.0037 (14)	0.0000 (15)
C12	0.0200 (18)	0.015 (3)	0.0124 (15)	0.0016 (17)	0.0062 (14)	−0.0020 (15)
C13	0.0179 (18)	0.014 (3)	0.0159 (17)	0.0019 (16)	0.0068 (14)	0.0034 (16)
C14	0.024 (2)	0.019 (2)	0.0122 (16)	−0.001 (2)	0.0024 (15)	−0.0014 (18)
C15	0.022 (2)	0.020 (3)	0.0116 (16)	0.002 (2)	0.0071 (15)	0.0001 (18)
C16	0.0181 (17)	0.025 (3)	0.0261 (18)	0.000 (2)	0.0101 (14)	−0.004 (2)

Br—C2	1.907 (4)	C8—H8A	0.9500
O1—C7	1.224 (5)	C9—C10	1.464 (5)
O2—C13	1.361 (5)	C9—H9A	0.9500
O2—C16	1.433 (5)	C10—C11	1.401 (6)
C1—C2	1.396 (5)	C10—C15	1.403 (6)
C1—C6	1.408 (6)	C11—C12	1.396 (6)
C1—C7	1.512 (5)	C11—H11A	0.9500
C2—C3	1.380 (6)	C12—C13	1.387 (6)
C3—C4	1.384 (7)	C12—H12A	0.9500
C3—H3A	0.9500	C13—C14	1.410 (6)
C4—C5	1.390 (6)	C14—C15	1.387 (6)
C4—H4A	0.9500	C14—H14A	0.9500
C5—C6	1.379 (6)	C15—H15A	0.9500
C5—H5A	0.9500	C16—H16A	0.9800
C6—H6A	0.9500	C16—H16B	0.9800
C7—C8	1.471 (6)	C16—H16C	0.9800
C8—C9	1.341 (6)
C13—O2—C16	116.7 (3)	C8—C9—H9A	116.4
C2—C1—C6	117.3 (4)	C10—C9—H9A	116.4
C2—C1—C7	125.7 (4)	C11—C10—C15	117.6 (4)
C6—C1—C7	117.1 (4)	C11—C10—C9	118.5 (4)
C3—C2—C1	121.9 (4)	C15—C10—C9	123.9 (4)
C3—C2—Br	116.4 (3)	C12—C11—C10	122.2 (4)
C1—C2—Br	121.7 (3)	C12—C11—H11A	118.9
C2—C3—C4	119.7 (4)	C10—C11—H11A	118.9
C2—C3—H3A	120.2	C13—C12—C11	118.9 (4)
C4—C3—H3A	120.2	C13—C12—H12A	120.6
C3—C4—C5	120.1 (4)	C11—C12—H12A	120.6
C3—C4—H4A	120.0	O2—C13—C12	124.5 (4)
C5—C4—H4A	120.0	O2—C13—C14	115.1 (4)
C6—C5—C4	119.9 (4)	C12—C13—C14	120.4 (4)
C6—C5—H5A	120.1	C15—C14—C13	119.5 (4)
C4—C5—H5A	120.1	C15—C14—H14A	120.2
C5—C6—C1	121.3 (4)	C13—C14—H14A	120.2
C5—C6—H6A	119.4	C14—C15—C10	121.3 (4)
C1—C6—H6A	119.4	C14—C15—H15A	119.3
O1—C7—C8	122.6 (4)	C10—C15—H15A	119.3
O1—C7—C1	118.7 (4)	O2—C16—H16A	109.5
C8—C7—C1	118.6 (4)	O2—C16—H16B	109.5
C9—C8—C7	120.5 (4)	H16A—C16—H16B	109.5
C9—C8—H8A	119.7	O2—C16—H16C	109.5
C7—C8—H8A	119.7	H16A—C16—H16C	109.5
C8—C9—C10	127.2 (4)	H16B—C16—H16C	109.5
C6—C1—C2—C3	0.1 (7)	C1—C7—C8—C9	164.4 (4)
C7—C1—C2—C3	−179.0 (4)	C7—C8—C9—C10	−178.4 (4)
C6—C1—C2—Br	177.7 (4)	C8—C9—C10—C11	−170.9 (4)
C7—C1—C2—Br	−1.3 (7)	C8—C9—C10—C15	9.4 (7)
C1—C2—C3—C4	−0.8 (7)	C15—C10—C11—C12	−2.4 (6)
Br—C2—C3—C4	−178.6 (4)	C9—C10—C11—C12	177.9 (4)
C2—C3—C4—C5	0.7 (8)	C10—C11—C12—C13	1.9 (6)
C3—C4—C5—C6	0.2 (9)	C16—O2—C13—C12	0.2 (7)
C4—C5—C6—C1	−1.1 (8)	C16—O2—C13—C14	179.6 (5)
C2—C1—C6—C5	0.9 (7)	C11—C12—C13—O2	179.4 (4)
C7—C1—C6—C5	180.0 (4)	C11—C12—C13—C14	0.0 (6)
C2—C1—C7—O1	139.4 (5)	O2—C13—C14—C15	179.2 (4)
C6—C1—C7—O1	−39.6 (7)	C12—C13—C14—C15	−1.4 (7)
C2—C1—C7—C8	−43.2 (7)	C13—C14—C15—C10	0.8 (7)
C6—C1—C7—C8	137.8 (5)	C11—C10—C15—C14	1.0 (7)
O1—C7—C8—C9	−18.2 (7)	C9—C10—C15—C14	−179.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1i	0.95	2.59	3.541 (5)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1i	0.95	2.59	3.541 (5)	174

Symmetry code: (i) .