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

The overall shape of the mol-ecule of the title compound, C(17)H(15)BrO(2), can be described by the dihedral angles between three planar fragments: 1-bromo-2-meth-oxy-phenyl ring [maximum deviation = 0.003 (2) Å], the central prop-2-en-1-one chain [maximum deviation = 0.005 (2) Å], and the methyl-phenyl ring [maximum deviation = 0.004 (2) Å]. The terminal planes are twisted by 10.37 (12)°, while the central plane is almost coplanar with the methyl-phenyl ring [3.30 (13)°], but the dihedral angle with the other phenyl ring is significantly larger [8.76 (16)°]. In the crystal, mol-ecules are linked into chains along [001] by three C-H⋯O hydrogen bonds. These chains inter-act with each other by means of weak π-π contacts [centroid-centroid distances = 3.73 (1) and 3.44 (1) Å]. An inter-molecular C-H⋯Br inter-action also occurs.

Related literature

For related structures, see: Butcher et al. (2006 ▶); Ng et al. (2006 ▶); Zhou (2010 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C17H15BrO2

M = 331.19

Monoclinic,

a = 11.680 (2) Å

b = 11.654 (2) Å

c = 10.834 (2) Å

β = 93.07 (2)°

V = 1472.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.79 mm−1

T = 295 K

0.5 × 0.3 × 0.1 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.276, T max = 1.000

6000 measured reflections

3003 independent reflections

1455 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.072

S = 1.00

3003 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011482/rk2271sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011482/rk2271Isup2.hkl

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

C17H15BrO2	F(000) = 672
Mr = 331.19	Dx = 1.494 Mg m−3
Monoclinic, P21/c	Melting point: 393 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.680 (2) Å	Cell parameters from 2134 reflections
b = 11.654 (2) Å	θ = 3.1–27.9°
c = 10.834 (2) Å	µ = 2.79 mm−1
β = 93.07 (2)°	T = 295 K
V = 1472.6 (4) Å3	Plate, colourless
Z = 4	0.5 × 0.3 × 0.1 mm

Agilent Xcalibur Eos diffractometer	3003 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1455 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 16.1544 pixels mm-1	θmax = 28.0°, θmin = 3.1°
ω–scan	h = −9→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→9
Tmin = 0.276, Tmax = 1.000	l = −12→14
6000 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.025P)2] where P = (Fo2 + 2Fc2)/3
3003 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.2928 (3)	0.2026 (2)	−0.0764 (3)	0.0370 (8)
O1	0.27055 (17)	0.18029 (18)	−0.18486 (19)	0.0502 (6)
C2	0.2054 (2)	0.2537 (2)	0.0006 (3)	0.0389 (8)
H2	0.2235	0.2686	0.0837	0.047*
C3	0.1015 (3)	0.2784 (2)	−0.0473 (3)	0.0387 (8)
H3	0.0881	0.2593	−0.1302	0.046*
C4	0.0056 (3)	0.3310 (2)	0.0112 (3)	0.0336 (7)
C5	0.0129 (3)	0.3788 (2)	0.1281 (3)	0.0376 (8)
H5	0.0823	0.3762	0.1744	0.045*
C6	−0.0804 (3)	0.4300 (3)	0.1771 (3)	0.0379 (8)
Br6	−0.06520 (3)	0.50120 (3)	0.33361 (3)	0.06471 (15)
C7	−0.1850 (3)	0.4354 (3)	0.1113 (3)	0.0394 (8)
O7	−0.27311 (18)	0.48560 (18)	0.1679 (2)	0.0561 (6)
C71	−0.3790 (3)	0.4986 (3)	0.0993 (3)	0.0688 (10)
H71A	−0.3664	0.5362	0.0224	0.103*
H71B	−0.4301	0.5440	0.1459	0.103*
H71C	−0.4124	0.4245	0.0833	0.103*
C8	−0.1948 (3)	0.3877 (3)	−0.0058 (3)	0.0477 (9)
H8	−0.2645	0.3897	−0.0515	0.057*
C9	−0.0998 (3)	0.3367 (3)	−0.0546 (3)	0.0462 (9)
H9	−0.1068	0.3054	−0.1336	0.055*
C11	0.4101 (3)	0.1804 (2)	−0.0206 (3)	0.0325 (7)
C12	0.4420 (3)	0.1998 (2)	0.1032 (3)	0.0466 (9)
H12	0.3886	0.2285	0.1560	0.056*
C13	0.5524 (3)	0.1766 (3)	0.1483 (3)	0.0490 (9)
H13	0.5720	0.1893	0.2315	0.059*
C14	0.6338 (3)	0.1350 (2)	0.0731 (3)	0.0404 (9)
C141	0.7531 (3)	0.1098 (3)	0.1243 (3)	0.0591 (10)
H14A	0.7866	0.1784	0.1594	0.089*
H14B	0.7988	0.0828	0.0591	0.089*
H14C	0.7503	0.0519	0.1871	0.089*
C15	0.6026 (3)	0.1157 (2)	−0.0504 (3)	0.0444 (9)
H15	0.6562	0.0877	−0.1032	0.053*
C16	0.4931 (3)	0.1376 (2)	−0.0946 (3)	0.0420 (9)
H16	0.4736	0.1233	−0.1775	0.050*

	U11	U22	U33	U12	U13	U23
C1	0.040 (2)	0.040 (2)	0.0315 (18)	0.0004 (17)	0.0049 (17)	0.0066 (16)
O1	0.0461 (15)	0.0741 (16)	0.0302 (13)	0.0064 (12)	0.0012 (12)	−0.0026 (12)
C2	0.037 (2)	0.048 (2)	0.0318 (18)	0.0017 (17)	−0.0009 (17)	0.0046 (16)
C3	0.044 (2)	0.042 (2)	0.0299 (18)	−0.0017 (17)	0.0015 (17)	0.0036 (15)
C4	0.0311 (18)	0.0391 (18)	0.0304 (17)	0.0046 (18)	−0.0007 (16)	0.0061 (17)
C5	0.0268 (19)	0.049 (2)	0.0369 (19)	−0.0029 (16)	−0.0027 (16)	0.0068 (16)
C6	0.036 (2)	0.044 (2)	0.0337 (18)	−0.0008 (17)	0.0029 (17)	0.0035 (16)
Br6	0.0554 (2)	0.0894 (3)	0.0494 (2)	0.0029 (2)	0.00389 (16)	−0.0202 (2)
C7	0.031 (2)	0.037 (2)	0.050 (2)	0.0009 (17)	0.0068 (18)	0.0070 (17)
O7	0.0331 (13)	0.0724 (17)	0.0630 (14)	0.0089 (14)	0.0056 (12)	0.0020 (14)
C71	0.035 (2)	0.075 (3)	0.097 (3)	0.008 (2)	0.004 (2)	−0.001 (2)
C8	0.030 (2)	0.062 (2)	0.050 (2)	−0.0027 (18)	−0.0070 (18)	0.0002 (19)
C9	0.044 (2)	0.060 (2)	0.0341 (19)	0.0031 (19)	−0.0054 (19)	−0.0016 (18)
C11	0.036 (2)	0.0310 (19)	0.0313 (18)	0.0003 (15)	0.0044 (16)	0.0003 (15)
C12	0.044 (2)	0.054 (2)	0.042 (2)	0.0106 (19)	0.0055 (18)	−0.0118 (17)
C13	0.052 (2)	0.057 (2)	0.038 (2)	0.008 (2)	0.0019 (19)	−0.0094 (18)
C14	0.037 (2)	0.035 (2)	0.049 (2)	−0.0003 (16)	0.0010 (19)	0.0040 (17)
C141	0.048 (2)	0.065 (3)	0.064 (3)	0.0112 (19)	−0.003 (2)	0.001 (2)
C15	0.037 (2)	0.052 (2)	0.045 (2)	0.0082 (18)	0.0116 (18)	0.0060 (17)
C16	0.051 (2)	0.047 (2)	0.0275 (18)	0.0027 (19)	0.0032 (18)	0.0027 (16)

C1—O1	1.218 (3)	C71—H71C	0.9600
C1—C2	1.478 (4)	C8—C9	1.388 (4)
C1—C11	1.491 (4)	C8—H8	0.9300
C2—C3	1.326 (4)	C9—H9	0.9300
C2—H2	0.9300	C11—C16	1.383 (4)
C3—C4	1.452 (4)	C11—C12	1.392 (4)
C3—H3	0.9300	C12—C13	1.381 (4)
C4—C5	1.382 (4)	C12—H12	0.9300
C4—C9	1.391 (4)	C13—C14	1.374 (4)
C5—C6	1.374 (4)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.386 (4)
C6—C7	1.383 (4)	C14—C141	1.501 (4)
C6—Br6	1.888 (3)	C141—H14A	0.9600
C7—O7	1.358 (3)	C141—H14B	0.9600
C7—C8	1.384 (4)	C141—H14C	0.9600
O7—C71	1.417 (3)	C15—C16	1.366 (4)
C71—H71A	0.9600	C15—H15	0.9300
C71—H71B	0.9600	C16—H16	0.9300
O1—C1—C2	120.8 (3)	C7—C8—H8	120.2
O1—C1—C11	119.9 (3)	C9—C8—H8	120.2
C2—C1—C11	119.3 (3)	C8—C9—C4	121.9 (3)
C3—C2—C1	120.8 (3)	C8—C9—H9	119.0
C3—C2—H2	119.6	C4—C9—H9	119.0
C1—C2—H2	119.6	C16—C11—C12	117.3 (3)
C2—C3—C4	129.2 (3)	C16—C11—C1	119.0 (3)
C2—C3—H3	115.4	C12—C11—C1	123.7 (3)
C4—C3—H3	115.4	C13—C12—C11	120.4 (3)
C5—C4—C9	117.4 (3)	C13—C12—H12	119.8
C5—C4—C3	124.0 (3)	C11—C12—H12	119.8
C9—C4—C3	118.6 (3)	C14—C13—C12	121.5 (3)
C6—C5—C4	121.2 (3)	C14—C13—H13	119.2
C6—C5—H5	119.4	C12—C13—H13	119.2
C4—C5—H5	119.4	C13—C14—C15	118.3 (3)
C5—C6—C7	121.2 (3)	C13—C14—C141	120.6 (3)
C5—C6—Br6	120.0 (2)	C15—C14—C141	121.1 (3)
C7—C6—Br6	118.7 (3)	C14—C141—H14A	109.5
O7—C7—C6	117.1 (3)	C14—C141—H14B	109.5
O7—C7—C8	124.1 (3)	H14A—C141—H14B	109.5
C6—C7—C8	118.8 (3)	C14—C141—H14C	109.5
C7—O7—C71	118.0 (3)	H14A—C141—H14C	109.5
O7—C71—H71A	109.5	H14B—C141—H14C	109.5
O7—C71—H71B	109.5	C16—C15—C14	120.1 (3)
H71A—C71—H71B	109.5	C16—C15—H15	119.9
O7—C71—H71C	109.5	C14—C15—H15	119.9
H71A—C71—H71C	109.5	C15—C16—C11	122.4 (3)
H71B—C71—H71C	109.5	C15—C16—H16	118.8
C7—C8—C9	119.5 (3)	C11—C16—H16	118.8

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.61	3.536 (3)	178
C5—H5···O1i	0.93	2.69	3.603 (4)	167
C12—H12···O1i	0.93	2.50	3.424 (4)	171
C141—H14B···Br6ii	0.96	3.14	4.100 (3)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.61	3.536 (3)	178
C5—H5⋯O1i	0.93	2.69	3.603 (4)	167
C12—H12⋯O1i	0.93	2.50	3.424 (4)	171
C141—H14B⋯Br6ii	0.96	3.14	4.100 (3)	176

Symmetry codes: (i) ; (ii) .