(2E)-1-(1,3-Benzodioxol-5-yl)-3-(2-bromo-phen-yl)prop-2-en-1-one.

The mol-ecule of the title compound, C(16)H(11)BrO(3), is essentially planar with a maximum deviation of 0.178 (4) Å and the configuration of the keto group with respect to the olefinic double bond is typically s-cis. In the crystal structure, inter-molecular Br⋯O inter-actions [3.187 (3)Å] give rise to chains parallel to the b axis. Adjacent chains are further linked along the a axis by C-H⋯π inter-actions. The crystal studied was a racemic twin with a 0.595 (13):0.405 (13) ratio.

Related literature

For chalcones, see: Di Carlo et al. (1999 ▶); Sarojini et al. (2006 ▶); Yarishkin et al. (2008 ▶). For halogen-bonding inter­actions, see: Thallapally et al. (2002 ▶); Metrangolo et al. (2005 ▶); Riley et al. (2009 ▶). For related structures, see: Harrison et al. (2006 ▶); Rathore et al. (2006 ▶); Li et al. (2008 ▶); Jasinski et al. (2010 ▶). For racemic twinning, see: Flack (1983 ▶); Flack & Bernardinelli (2000 ▶); Gömez et al. (2010 ▶).

Experimental

Crystal data

C16H11BrO3

M = 331.16

Orthorhombic,

a = 5.0434 (2) Å

b = 12.9354 (4) Å

c = 20.8916 (7) Å

V = 1362.93 (8) Å3

Z = 4

Mo Kα radiation

μ = 3.02 mm−1

T = 296 K

0.53 × 0.19 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.576, T max = 0.653

17031 measured reflections

2674 independent reflections

2437 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.086

S = 1.06

2674 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.52 e Å−3

Absolute structure: Flack (1983 ▶), 1086 Bijvoet pairs

Flack parameter: 0.595 (13)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015552/rz2432sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015552/rz2432Isup2.hkl

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

C16H11BrO3	Dx = 1.614 Mg m−3
Mr = 331.16	Melting point = 390–392 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7488 reflections
a = 5.0434 (2) Å	θ = 2.5–25.7°
b = 12.9354 (4) Å	µ = 3.02 mm−1
c = 20.8916 (7) Å	T = 296 K
V = 1362.93 (8) Å3	Block, colorless
Z = 4	0.53 × 0.19 × 0.16 mm
F(000) = 664

Bruker SMART APEXII CCD area-detector diffractometer	2674 independent reflections
Radiation source: fine-focus sealed tube	2437 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −6→6
Tmin = 0.576, Tmax = 0.653	k = −13→15
17031 measured reflections	l = −25→25

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) = 0.086	w = 1/[σ2(Fo2) + (0.0412P)2 + 0.7667P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2674 reflections	Δρmax = 0.64 e Å−3
182 parameters	Δρmin = −0.51 e Å−3
0 restraints	Absolute structure: Flack (1983), 1086 Bijvoet pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.595 (13)

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
Br1	0.74414 (9)	0.52368 (3)	0.425085 (18)	0.07369 (16)
O1	0.0651 (6)	0.5167 (2)	0.25271 (15)	0.0779 (9)
O2	−0.6166 (5)	0.26394 (18)	0.06042 (12)	0.0586 (6)
O3	−0.6165 (5)	0.44083 (18)	0.07678 (11)	0.0554 (5)
C1	0.7744 (7)	0.3802 (2)	0.40661 (13)	0.0493 (7)
C2	0.9616 (7)	0.3239 (3)	0.44092 (16)	0.0610 (9)
H2	1.0660	0.3561	0.4717	0.073*
C3	0.9903 (8)	0.2201 (3)	0.42877 (19)	0.0679 (11)
H3	1.1121	0.1813	0.4520	0.081*
C4	0.8394 (8)	0.1738 (3)	0.3824 (2)	0.0661 (10)
H4	0.8595	0.1036	0.3741	0.079*
C5	0.6594 (7)	0.2304 (3)	0.34812 (17)	0.0576 (9)
H5	0.5603	0.1975	0.3166	0.069*
C6	0.6196 (6)	0.3355 (3)	0.35892 (14)	0.0461 (7)
C7	0.4282 (7)	0.3947 (3)	0.32148 (16)	0.0533 (8)
H7	0.4276	0.4658	0.3280	0.064*
C8	0.2596 (7)	0.3595 (2)	0.28037 (14)	0.0524 (7)
H8	0.2561	0.2885	0.2732	0.063*
C9	0.0717 (6)	0.4246 (3)	0.24404 (15)	0.0461 (7)
C10	−0.1054 (6)	0.3754 (2)	0.19621 (13)	0.0413 (6)
C11	−0.1108 (7)	0.2691 (3)	0.18603 (16)	0.0486 (7)
H11	0.0015	0.2268	0.2097	0.058*
C12	−0.2804 (7)	0.2245 (2)	0.14116 (15)	0.0522 (8)
H12	−0.2842	0.1534	0.1347	0.063*
C13	−0.4395 (6)	0.2889 (2)	0.10737 (14)	0.0436 (7)
C14	−0.4375 (6)	0.3942 (2)	0.11713 (13)	0.0398 (6)
C15	−0.2737 (7)	0.4401 (2)	0.16089 (12)	0.0430 (6)
H15	−0.2739	0.5113	0.1670	0.052*
C16	−0.7382 (8)	0.3593 (2)	0.04180 (13)	0.0498 (7)
H16A	−0.7151	0.3704	−0.0038	0.060*
H16B	−0.9267	0.3572	0.0510	0.060*

	U11	U22	U33	U12	U13	U23
Br1	0.0729 (2)	0.0700 (2)	0.0781 (3)	0.0085 (2)	−0.0259 (2)	−0.02381 (18)
O1	0.096 (2)	0.0487 (15)	0.0889 (19)	0.0021 (15)	−0.0448 (17)	−0.0083 (14)
O2	0.0621 (14)	0.0532 (13)	0.0605 (13)	0.0012 (11)	−0.0161 (12)	−0.0129 (11)
O3	0.0580 (13)	0.0492 (12)	0.0589 (13)	0.0062 (11)	−0.0187 (11)	−0.0013 (11)
C1	0.0454 (16)	0.0575 (17)	0.0449 (14)	−0.0019 (17)	0.0005 (14)	0.0032 (12)
C2	0.0490 (18)	0.088 (3)	0.0466 (17)	0.0060 (18)	−0.0039 (15)	0.0082 (18)
C3	0.057 (2)	0.083 (3)	0.064 (2)	0.0180 (19)	0.0026 (19)	0.027 (2)
C4	0.064 (2)	0.054 (2)	0.081 (2)	0.0069 (16)	0.0111 (19)	0.017 (2)
C5	0.056 (2)	0.056 (2)	0.0608 (19)	−0.0020 (15)	0.0003 (16)	0.0071 (17)
C6	0.0418 (15)	0.0552 (19)	0.0415 (15)	−0.0003 (15)	0.0029 (12)	0.0046 (13)
C7	0.0564 (19)	0.0461 (18)	0.0575 (18)	0.0046 (15)	−0.0111 (16)	−0.0041 (15)
C8	0.0509 (16)	0.0510 (16)	0.0553 (16)	−0.003 (2)	−0.0075 (18)	−0.0004 (13)
C9	0.0473 (17)	0.0479 (19)	0.0432 (15)	−0.0038 (15)	−0.0021 (13)	−0.0006 (13)
C10	0.0411 (15)	0.0450 (16)	0.0378 (13)	−0.0004 (13)	0.0037 (12)	0.0025 (13)
C11	0.0464 (17)	0.0473 (18)	0.0522 (17)	0.0055 (15)	−0.0052 (15)	0.0026 (15)
C12	0.058 (2)	0.0368 (14)	0.0621 (17)	−0.0016 (17)	−0.0073 (18)	−0.0041 (13)
C13	0.0435 (16)	0.0458 (17)	0.0415 (14)	−0.0033 (13)	0.0011 (13)	−0.0046 (13)
C14	0.0371 (14)	0.0441 (16)	0.0383 (13)	0.0011 (12)	0.0031 (12)	0.0026 (12)
C15	0.0463 (16)	0.0397 (13)	0.0429 (13)	−0.0003 (16)	−0.0004 (13)	−0.0022 (11)
C16	0.0492 (16)	0.0540 (17)	0.0463 (14)	−0.005 (2)	−0.0056 (16)	0.0007 (12)

Br1—C1	1.902 (3)	C7—C8	1.292 (5)
O1—C9	1.206 (4)	C7—H7	0.9300
O2—C13	1.365 (4)	C8—C9	1.478 (5)
O2—C16	1.431 (4)	C8—H8	0.9300
O3—C14	1.374 (4)	C9—C10	1.484 (4)
O3—C16	1.423 (4)	C10—C11	1.391 (4)
C1—C2	1.391 (5)	C10—C15	1.402 (4)
C1—C6	1.392 (4)	C11—C12	1.394 (4)
C2—C3	1.374 (6)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.355 (4)
C3—C4	1.371 (6)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.378 (4)
C4—C5	1.368 (5)	C14—C15	1.368 (4)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.393 (5)	C16—H16A	0.9700
C5—H5	0.9300	C16—H16B	0.9700
C6—C7	1.459 (4)
C13—O2—C16	105.8 (2)	O1—C9—C10	120.6 (3)
C14—O3—C16	105.9 (2)	C8—C9—C10	119.1 (3)
C2—C1—C6	122.1 (3)	C11—C10—C15	119.9 (3)
C2—C1—Br1	117.4 (3)	C11—C10—C9	122.6 (3)
C6—C1—Br1	120.4 (2)	C15—C10—C9	117.5 (3)
C3—C2—C1	119.2 (4)	C10—C11—C12	121.6 (3)
C3—C2—H2	120.4	C10—C11—H11	119.2
C1—C2—H2	120.4	C12—C11—H11	119.2
C4—C3—C2	120.0 (3)	C13—C12—C11	117.3 (3)
C4—C3—H3	120.0	C13—C12—H12	121.3
C2—C3—H3	120.0	C11—C12—H12	121.3
C5—C4—C3	120.3 (4)	C12—C13—O2	128.1 (3)
C5—C4—H4	119.9	C12—C13—C14	121.8 (3)
C3—C4—H4	119.9	O2—C13—C14	110.2 (3)
C4—C5—C6	122.2 (4)	C15—C14—O3	128.0 (3)
C4—C5—H5	118.9	C15—C14—C13	122.2 (3)
C6—C5—H5	118.9	O3—C14—C13	109.8 (3)
C1—C6—C5	116.2 (3)	C14—C15—C10	117.3 (3)
C1—C6—C7	122.4 (3)	C14—C15—H15	121.4
C5—C6—C7	121.4 (3)	C10—C15—H15	121.4
C8—C7—C6	127.4 (3)	O3—C16—O2	108.3 (2)
C8—C7—H7	116.3	O3—C16—H16A	110.0
C6—C7—H7	116.3	O2—C16—H16A	110.0
C7—C8—C9	124.3 (3)	O3—C16—H16B	110.0
C7—C8—H8	117.9	O2—C16—H16B	110.0
C9—C8—H8	117.9	H16A—C16—H16B	108.4
O1—C9—C8	120.3 (3)
C6—C1—C2—C3	−1.8 (5)	C15—C10—C11—C12	0.1 (5)
Br1—C1—C2—C3	−179.7 (3)	C9—C10—C11—C12	179.5 (3)
C1—C2—C3—C4	1.4 (5)	C10—C11—C12—C13	0.4 (5)
C2—C3—C4—C5	−0.2 (6)	C11—C12—C13—O2	178.6 (3)
C3—C4—C5—C6	−0.6 (6)	C11—C12—C13—C14	−0.7 (5)
C2—C1—C6—C5	1.0 (5)	C16—O2—C13—C12	178.4 (3)
Br1—C1—C6—C5	178.8 (2)	C16—O2—C13—C14	−2.3 (3)
C2—C1—C6—C7	−178.2 (3)	C16—O3—C14—C15	−179.3 (3)
Br1—C1—C6—C7	−0.4 (4)	C16—O3—C14—C13	1.5 (3)
C4—C5—C6—C1	0.2 (5)	C12—C13—C14—C15	0.6 (5)
C4—C5—C6—C7	179.4 (3)	O2—C13—C14—C15	−178.8 (3)
C1—C6—C7—C8	−173.5 (4)	C12—C13—C14—O3	180.0 (3)
C5—C6—C7—C8	7.4 (6)	O2—C13—C14—O3	0.5 (4)
C6—C7—C8—C9	−179.8 (3)	O3—C14—C15—C10	−179.3 (3)
C7—C8—C9—O1	−1.5 (6)	C13—C14—C15—C10	−0.1 (4)
C7—C8—C9—C10	177.6 (3)	C11—C10—C15—C14	−0.2 (4)
O1—C9—C10—C11	−177.9 (4)	C9—C10—C15—C14	−179.7 (3)
C8—C9—C10—C11	3.0 (4)	C14—O3—C16—O2	−2.8 (3)
O1—C9—C10—C15	1.5 (5)	C13—O2—C16—O3	3.1 (3)
C8—C9—C10—C15	−177.6 (3)

Cg3 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Br1	0.93	2.69	3.164 (4)	113
C7—H7···O1	0.93	2.50	2.812 (6)	100
C16—H16B···Cg3i	0.97	2.76	3.563 (4)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯Cg3i	0.97	2.76	3.563 (4)	141

Symmetry code: (i) .