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

In the title chalcone derivative, C(17)H(15)BrO, the dihedral angle between the two benzene rings is 48.13 (4)°. In the crystal, a short Br⋯Br contact of 3.5052 (10) Å occurs.

Related literature

For a related structure and background to chalcones, see: Fun et al. (2008 ▶).

Experimental

Crystal data

C17H15BrO

M = 315.20

Triclinic,

a = 5.9786 (14) Å

b = 7.8437 (19) Å

c = 15.744 (4) Å

α = 99.054 (4)°

β = 99.602 (4)°

γ = 95.659 (4)°

V = 713.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.87 mm−1

T = 298 K

0.25 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

3911 measured reflections

2620 independent reflections

2198 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.095

S = 1.09

2620 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.60 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536810018106/hb5445sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018106/hb5445Isup2.hkl

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

C17H15BrO	Z = 2
Mr = 315.20	F(000) = 320
Triclinic, P1	Dx = 1.468 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9786 (14) Å	Cell parameters from 2198 reflections
b = 7.8437 (19) Å	θ = 1.3–25.5°
c = 15.744 (4) Å	µ = 2.87 mm−1
α = 99.054 (4)°	T = 298 K
β = 99.602 (4)°	Bar, yellow
γ = 95.659 (4)°	0.25 × 0.22 × 0.20 mm
V = 713.0 (3) Å3

Bruker SMART CCD diffractometer	2198 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
graphite	θmax = 25.5°, θmin = 1.3°
phi and ω scans	h = −7→7
3911 measured reflections	k = −9→6
2620 independent reflections	l = −18→19

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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.048P)2 + 0.2458P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2620 reflections	Δρmax = 0.45 e Å−3
173 parameters	Δρmin = −0.60 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.048 (4)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.57731 (6)	0.43242 (4)	0.100602 (19)	0.06655 (18)
C11	0.5449 (5)	0.3857 (3)	0.21288 (17)	0.0440 (6)
O	0.2750 (3)	0.2761 (3)	0.48223 (13)	0.0628 (6)
C10	0.7328 (5)	0.4220 (4)	0.27985 (18)	0.0482 (6)
H10A	0.8724	0.4717	0.2706	0.058*
C17	0.4645 (5)	0.2760 (4)	0.46327 (17)	0.0455 (6)
C12	0.3349 (5)	0.3142 (4)	0.22550 (18)	0.0506 (7)
H12A	0.2100	0.2898	0.1796	0.061*
C9	0.7107 (4)	0.3834 (3)	0.36099 (17)	0.0448 (6)
H9A	0.8374	0.4048	0.4061	0.054*
C8	0.5010 (4)	0.3129 (3)	0.37593 (16)	0.0395 (5)
C6	1.1464 (4)	0.0981 (3)	0.80706 (18)	0.0453 (6)
C5	0.9589 (4)	0.1781 (4)	0.82839 (17)	0.0448 (6)
C3	0.8289 (4)	0.1904 (3)	0.67426 (17)	0.0408 (6)
C4	0.8024 (4)	0.2208 (3)	0.76150 (17)	0.0437 (6)
H4A	0.6759	0.2714	0.7755	0.052*
C16	0.6528 (5)	0.2356 (3)	0.60745 (17)	0.0437 (6)
H16A	0.5194	0.2656	0.6256	0.052*
C2	1.0206 (5)	0.1157 (3)	0.65442 (18)	0.0459 (6)
H2A	1.0448	0.0967	0.5970	0.055*
C7	0.3131 (5)	0.2796 (4)	0.30725 (17)	0.0464 (6)
H7A	0.1717	0.2335	0.3167	0.056*
C15	0.6631 (5)	0.2384 (4)	0.52402 (18)	0.0477 (6)
H15A	0.7966	0.2164	0.5036	0.057*
C1	1.1749 (5)	0.0697 (3)	0.72054 (19)	0.0474 (6)
H1A	1.3008	0.0184	0.7064	0.057*
C14	0.9249 (6)	0.2180 (5)	0.9221 (2)	0.0674 (9)
H14A	0.7885	0.2726	0.9242	0.101*
H14B	1.0541	0.2950	0.9567	0.101*
H14C	0.9103	0.1119	0.9450	0.101*
C13	1.3147 (6)	0.0413 (4)	0.8765 (2)	0.0635 (8)
H13A	1.4312	−0.0106	0.8501	0.095*
H13B	1.2362	−0.0421	0.9034	0.095*
H13C	1.3838	0.1406	0.9201	0.095*

	U11	U22	U33	U12	U13	U23
Br	0.0949 (3)	0.0686 (3)	0.0421 (2)	0.01006 (17)	0.01910 (16)	0.02128 (15)
C11	0.0583 (16)	0.0408 (13)	0.0358 (13)	0.0098 (12)	0.0132 (12)	0.0091 (11)
O	0.0507 (12)	0.0955 (16)	0.0468 (11)	0.0114 (11)	0.0174 (9)	0.0161 (11)
C10	0.0477 (15)	0.0507 (15)	0.0470 (15)	0.0019 (12)	0.0133 (12)	0.0092 (12)
C17	0.0508 (16)	0.0485 (15)	0.0367 (13)	0.0058 (12)	0.0101 (11)	0.0043 (11)
C12	0.0514 (16)	0.0571 (17)	0.0394 (14)	0.0025 (13)	−0.0017 (12)	0.0104 (12)
C9	0.0420 (14)	0.0502 (15)	0.0387 (14)	0.0038 (11)	0.0027 (11)	0.0042 (11)
C8	0.0449 (14)	0.0387 (13)	0.0361 (13)	0.0085 (10)	0.0108 (10)	0.0052 (10)
C6	0.0446 (14)	0.0401 (13)	0.0501 (15)	0.0030 (11)	0.0045 (12)	0.0112 (12)
C5	0.0434 (14)	0.0507 (15)	0.0403 (14)	0.0011 (11)	0.0081 (11)	0.0106 (12)
C3	0.0434 (14)	0.0406 (13)	0.0395 (13)	0.0027 (10)	0.0096 (11)	0.0104 (11)
C4	0.0417 (14)	0.0500 (15)	0.0421 (14)	0.0088 (11)	0.0120 (11)	0.0098 (12)
C16	0.0459 (14)	0.0452 (14)	0.0413 (14)	0.0061 (11)	0.0113 (11)	0.0086 (11)
C2	0.0528 (15)	0.0460 (14)	0.0401 (14)	0.0052 (12)	0.0147 (12)	0.0052 (11)
C7	0.0423 (14)	0.0534 (16)	0.0428 (15)	0.0010 (12)	0.0067 (11)	0.0107 (12)
C15	0.0525 (16)	0.0562 (16)	0.0389 (14)	0.0138 (13)	0.0139 (12)	0.0120 (12)
C1	0.0432 (14)	0.0430 (14)	0.0580 (17)	0.0092 (11)	0.0149 (12)	0.0071 (12)
C14	0.0606 (19)	0.103 (3)	0.0422 (17)	0.0175 (17)	0.0120 (14)	0.0157 (17)
C13	0.0604 (19)	0.067 (2)	0.064 (2)	0.0181 (15)	0.0032 (15)	0.0181 (16)

Br—C11	1.898 (3)	C3—C2	1.396 (4)
C11—C10	1.379 (4)	C3—C4	1.395 (4)
C11—C12	1.382 (4)	C3—C16	1.470 (4)
O—C17	1.219 (3)	C4—H4A	0.9300
C10—C9	1.382 (4)	C16—C15	1.329 (4)
C10—H10A	0.9300	C16—H16A	0.9300
C17—C15	1.480 (4)	C2—C1	1.389 (4)
C17—C8	1.495 (4)	C2—H2A	0.9300
C12—C7	1.381 (4)	C7—H7A	0.9300
C12—H12A	0.9300	C15—H15A	0.9300
C9—C8	1.391 (4)	C1—H1A	0.9300
C9—H9A	0.9300	C14—H14A	0.9600
C8—C7	1.396 (4)	C14—H14B	0.9600
C6—C1	1.387 (4)	C14—H14C	0.9600
C6—C5	1.400 (4)	C13—H13A	0.9600
C6—C13	1.510 (4)	C13—H13B	0.9600
C5—C4	1.393 (4)	C13—H13C	0.9600
C5—C14	1.512 (4)
C10—C11—C12	121.5 (2)	C3—C4—H4A	118.9
C10—C11—Br	119.1 (2)	C15—C16—C3	127.2 (3)
C12—C11—Br	119.4 (2)	C15—C16—H16A	116.4
C11—C10—C9	119.1 (2)	C3—C16—H16A	116.4
C11—C10—H10A	120.5	C1—C2—C3	119.9 (2)
C9—C10—H10A	120.5	C1—C2—H2A	120.1
O—C17—C15	122.0 (3)	C3—C2—H2A	120.1
O—C17—C8	119.9 (2)	C12—C7—C8	120.7 (2)
C15—C17—C8	118.0 (2)	C12—C7—H7A	119.7
C11—C12—C7	119.1 (2)	C8—C7—H7A	119.7
C11—C12—H12A	120.5	C16—C15—C17	120.7 (3)
C7—C12—H12A	120.5	C16—C15—H15A	119.6
C10—C9—C8	120.8 (2)	C17—C15—H15A	119.6
C10—C9—H9A	119.6	C6—C1—C2	121.8 (2)
C8—C9—H9A	119.6	C6—C1—H1A	119.1
C9—C8—C7	118.9 (2)	C2—C1—H1A	119.1
C9—C8—C17	123.1 (2)	C5—C14—H14A	109.5
C7—C8—C17	117.9 (2)	C5—C14—H14B	109.5
C1—C6—C5	119.0 (2)	H14A—C14—H14B	109.5
C1—C6—C13	120.0 (3)	C5—C14—H14C	109.5
C5—C6—C13	121.0 (3)	H14A—C14—H14C	109.5
C4—C5—C6	118.9 (2)	H14B—C14—H14C	109.5
C4—C5—C14	120.0 (2)	C6—C13—H13A	109.5
C6—C5—C14	121.1 (3)	C6—C13—H13B	109.5
C2—C3—C4	118.2 (2)	H13A—C13—H13B	109.5
C2—C3—C16	123.1 (2)	C6—C13—H13C	109.5
C4—C3—C16	118.8 (2)	H13A—C13—H13C	109.5
C5—C4—C3	122.3 (2)	H13B—C13—H13C	109.5
C5—C4—H4A	118.9