(E)-3-(Anthracen-9-yl)-1-(2-bromo-phen-yl)prop-2-en-1-one.

The mol-ecule of the title chalcone, C(23)H(15)BrO, is not planar and exists in the E configuration with respect to the central C=C bond. The dihedral angle between the benzene and anthracene rings is 83.58 (6)°. The prop-2-en-1-one bridge makes dihedral angles of 63.00 (7) and 42.62 (16)° with the benzene and anthracene rings, respectively. In the crystal, mol-ecules are linked into dimers by weak C-H⋯O inter-actions. These dimers are arranged parallel to the bc plane and are further stacked along the a axis by π-π inter-actions with a centroid-centroid distance of 3.7561 (9) Å. The crystal structure is further stabilized by C-H⋯π inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2009 ▶); Joothamongkhon et al. (2010 ▶). For background to and applications of chalcones, see: Cheng et al. (2008 ▶); Gaber et al. (2008 ▶); Joothamongkhon et al. (2010 ▶); Nawakowska et al. (2008) ▶; Patil & Dharmaprakash (2008 ▶); Tewtrakul et al. (2003 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C23H15BrO

M = 387.25

Orthorhombic,

a = 7.8631 (1) Å

b = 20.0583 (3) Å

c = 20.7259 (3) Å

V = 3268.90 (8) Å3

Z = 8

Mo Kα radiation

μ = 2.52 mm−1

T = 100 K

0.34 × 0.28 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.482, T max = 0.629

22332 measured reflections

4766 independent reflections

3717 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.073

S = 1.02

4766 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048476/rz2527sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048476/rz2527Isup2.hkl

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

C23H15BrO	Dx = 1.574 Mg m−3
Mr = 387.25	Melting point = 427–428 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4766 reflections
a = 7.8631 (1) Å	θ = 2.0–30.0°
b = 20.0583 (3) Å	µ = 2.52 mm−1
c = 20.7259 (3) Å	T = 100 K
V = 3268.90 (8) Å3	Block, yellow
Z = 8	0.34 × 0.28 × 0.20 mm
F(000) = 1568

Bruker APEXII CCD area-detector diffractometer	4766 independent reflections
Radiation source: sealed tube	3717 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→9
Tmin = 0.482, Tmax = 0.629	k = −28→21
22332 measured reflections	l = −26→29

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0336P)2 + 1.3057P] where P = (Fo2 + 2Fc2)/3
4766 reflections	(Δ/σ)max = 0.002
226 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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	−0.28035 (2)	0.124729 (8)	0.534873 (8)	0.01848 (6)
O1	−0.02804 (17)	0.24813 (6)	0.51069 (6)	0.0207 (3)
C1	−0.0478 (2)	0.09958 (8)	0.53816 (8)	0.0141 (3)
C2	−0.0051 (2)	0.04186 (8)	0.57118 (8)	0.0182 (3)
H2A	−0.0883	0.0173	0.5925	0.022*
C3	0.1634 (2)	0.02107 (9)	0.57209 (8)	0.0187 (3)
H3A	0.1936	−0.0173	0.5946	0.022*
C4	0.2868 (2)	0.05739 (9)	0.53953 (8)	0.0169 (3)
H4A	0.3991	0.0429	0.5396	0.020*
C5	0.2427 (2)	0.11522 (8)	0.50691 (8)	0.0148 (3)
H5A	0.3260	0.1393	0.4852	0.018*
C6	0.0743 (2)	0.13775 (8)	0.50626 (7)	0.0130 (3)
C7	0.0308 (2)	0.20401 (8)	0.47631 (7)	0.0144 (3)
C8	0.0571 (2)	0.21502 (8)	0.40715 (8)	0.0152 (3)
H8A	0.0380	0.2577	0.3913	0.018*
C9	0.1067 (2)	0.16805 (8)	0.36499 (8)	0.0143 (3)
H9A	0.1357	0.1266	0.3817	0.017*
C10	0.1193 (2)	0.17648 (8)	0.29459 (7)	0.0136 (3)
C11	0.1861 (2)	0.23539 (8)	0.26620 (8)	0.0146 (3)
C12	0.2644 (2)	0.28787 (8)	0.30234 (9)	0.0172 (3)
H12A	0.2765	0.2832	0.3467	0.021*
C13	0.3216 (2)	0.34451 (9)	0.27314 (9)	0.0210 (4)
H13A	0.3715	0.3779	0.2978	0.025*
C14	0.3059 (2)	0.35296 (9)	0.20539 (9)	0.0227 (4)
H14A	0.3417	0.3924	0.1861	0.027*
C15	0.2388 (2)	0.30366 (9)	0.16882 (9)	0.0211 (4)
H15A	0.2303	0.3095	0.1244	0.025*
C16	0.1807 (2)	0.24275 (8)	0.19713 (8)	0.0168 (3)
C17	0.1193 (2)	0.19111 (8)	0.15893 (8)	0.0184 (3)
H17A	0.1169	0.1964	0.1144	0.022*
C18	0.0612 (2)	0.13157 (8)	0.18586 (8)	0.0161 (3)
C19	0.0007 (2)	0.07806 (9)	0.14641 (8)	0.0206 (4)
H19A	0.0033	0.0825	0.1018	0.025*
C20	−0.0605 (2)	0.02092 (9)	0.17272 (9)	0.0213 (4)
H20A	−0.0984	−0.0134	0.1462	0.026*
C21	−0.0666 (2)	0.01375 (9)	0.24085 (9)	0.0208 (4)
H21A	−0.1095	−0.0252	0.2589	0.025*
C22	−0.0101 (2)	0.06361 (8)	0.28000 (8)	0.0178 (3)
H22A	−0.0167	0.0581	0.3245	0.021*
C23	0.0591 (2)	0.12412 (8)	0.25471 (8)	0.0143 (3)

	U11	U22	U33	U12	U13	U23
Br1	0.01349 (9)	0.01896 (9)	0.02300 (10)	0.00166 (6)	0.00026 (7)	0.00057 (7)
O1	0.0275 (7)	0.0153 (6)	0.0193 (6)	0.0025 (5)	0.0052 (5)	−0.0013 (5)
C1	0.0132 (8)	0.0144 (7)	0.0146 (8)	0.0010 (6)	−0.0003 (6)	−0.0014 (6)
C2	0.0190 (9)	0.0186 (8)	0.0168 (8)	−0.0012 (7)	0.0029 (7)	0.0039 (6)
C3	0.0209 (9)	0.0175 (8)	0.0175 (8)	0.0021 (7)	−0.0002 (7)	0.0039 (6)
C4	0.0156 (8)	0.0187 (8)	0.0165 (8)	0.0013 (6)	−0.0001 (7)	−0.0009 (6)
C5	0.0171 (9)	0.0150 (8)	0.0124 (7)	−0.0016 (6)	0.0015 (6)	−0.0012 (6)
C6	0.0166 (8)	0.0130 (7)	0.0094 (7)	−0.0002 (6)	−0.0005 (6)	−0.0015 (5)
C7	0.0149 (8)	0.0136 (7)	0.0147 (8)	−0.0022 (6)	0.0004 (6)	0.0003 (6)
C8	0.0164 (8)	0.0145 (8)	0.0147 (8)	0.0008 (6)	−0.0001 (6)	0.0030 (6)
C9	0.0150 (8)	0.0148 (7)	0.0131 (7)	−0.0006 (6)	−0.0012 (6)	0.0036 (6)
C10	0.0139 (8)	0.0152 (8)	0.0117 (7)	0.0030 (6)	0.0006 (6)	0.0015 (6)
C11	0.0128 (8)	0.0163 (8)	0.0148 (8)	0.0038 (6)	0.0016 (6)	0.0031 (6)
C12	0.0169 (8)	0.0178 (8)	0.0170 (8)	0.0024 (6)	0.0024 (6)	0.0021 (6)
C13	0.0168 (9)	0.0181 (9)	0.0280 (9)	−0.0003 (7)	0.0030 (7)	0.0005 (7)
C14	0.0196 (10)	0.0196 (8)	0.0290 (10)	0.0019 (7)	0.0065 (7)	0.0099 (7)
C15	0.0213 (9)	0.0243 (9)	0.0178 (8)	0.0060 (7)	0.0052 (7)	0.0097 (7)
C16	0.0144 (8)	0.0201 (8)	0.0159 (8)	0.0049 (6)	0.0028 (6)	0.0054 (6)
C17	0.0183 (9)	0.0248 (9)	0.0122 (8)	0.0071 (7)	0.0022 (6)	0.0044 (6)
C18	0.0158 (8)	0.0201 (8)	0.0122 (7)	0.0047 (6)	0.0007 (6)	0.0007 (6)
C19	0.0201 (9)	0.0283 (9)	0.0134 (8)	0.0065 (7)	−0.0030 (7)	−0.0044 (7)
C20	0.0207 (9)	0.0220 (8)	0.0212 (9)	0.0038 (7)	−0.0029 (7)	−0.0074 (7)
C21	0.0179 (9)	0.0191 (8)	0.0254 (9)	−0.0002 (7)	0.0002 (7)	0.0004 (7)
C22	0.0179 (9)	0.0185 (8)	0.0169 (8)	0.0015 (6)	0.0001 (6)	0.0021 (6)
C23	0.0130 (8)	0.0170 (8)	0.0128 (7)	0.0045 (6)	−0.0001 (6)	0.0019 (6)

Br1—C1	1.8983 (17)	C12—C13	1.364 (2)
O1—C7	1.2269 (19)	C12—H12A	0.9300
C1—C2	1.386 (2)	C13—C14	1.420 (3)
C1—C6	1.395 (2)	C13—H13A	0.9300
C2—C3	1.389 (2)	C14—C15	1.353 (3)
C2—H2A	0.9300	C14—H14A	0.9300
C3—C4	1.388 (2)	C15—C16	1.430 (2)
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.387 (2)	C16—C17	1.390 (2)
C4—H4A	0.9300	C17—C18	1.395 (2)
C5—C6	1.399 (2)	C17—H17A	0.9300
C5—H5A	0.9300	C18—C19	1.431 (2)
C6—C7	1.506 (2)	C18—C23	1.435 (2)
C7—C8	1.465 (2)	C19—C20	1.357 (3)
C8—C9	1.343 (2)	C19—H19A	0.9300
C8—H8A	0.9300	C20—C21	1.420 (2)
C9—C10	1.472 (2)	C20—H20A	0.9300
C9—H9A	0.9300	C21—C22	1.362 (2)
C10—C23	1.418 (2)	C21—H21A	0.9300
C10—C11	1.421 (2)	C22—C23	1.430 (2)
C11—C12	1.431 (2)	C22—H22A	0.9300
C11—C16	1.440 (2)
C2—C1—C6	121.74 (16)	C11—C12—H12A	119.3
C2—C1—Br1	118.21 (13)	C12—C13—C14	120.64 (17)
C6—C1—Br1	120.02 (12)	C12—C13—H13A	119.7
C1—C2—C3	119.22 (16)	C14—C13—H13A	119.7
C1—C2—H2A	120.4	C15—C14—C13	120.04 (16)
C3—C2—H2A	120.4	C15—C14—H14A	120.0
C4—C3—C2	120.15 (16)	C13—C14—H14A	120.0
C4—C3—H3A	119.9	C14—C15—C16	121.28 (17)
C2—C3—H3A	119.9	C14—C15—H15A	119.4
C5—C4—C3	120.10 (16)	C16—C15—H15A	119.4
C5—C4—H4A	120.0	C17—C16—C15	120.92 (16)
C3—C4—H4A	120.0	C17—C16—C11	120.00 (15)
C4—C5—C6	120.76 (15)	C15—C16—C11	119.08 (16)
C4—C5—H5A	119.6	C16—C17—C18	121.58 (15)
C6—C5—H5A	119.6	C16—C17—H17A	119.2
C1—C6—C5	118.00 (15)	C18—C17—H17A	119.2
C1—C6—C7	121.57 (15)	C17—C18—C19	121.51 (15)
C5—C6—C7	120.25 (15)	C17—C18—C23	119.39 (15)
O1—C7—C8	120.84 (14)	C19—C18—C23	119.09 (15)
O1—C7—C6	118.86 (14)	C20—C19—C18	121.46 (16)
C8—C7—C6	120.29 (14)	C20—C19—H19A	119.3
C9—C8—C7	124.87 (15)	C18—C19—H19A	119.3
C9—C8—H8A	117.6	C19—C20—C21	119.79 (16)
C7—C8—H8A	117.6	C19—C20—H20A	120.1
C8—C9—C10	125.72 (15)	C21—C20—H20A	120.1
C8—C9—H9A	117.1	C22—C21—C20	120.45 (17)
C10—C9—H9A	117.1	C22—C21—H21A	119.8
C23—C10—C11	119.88 (14)	C20—C21—H21A	119.8
C23—C10—C9	118.06 (14)	C21—C22—C23	121.94 (16)
C11—C10—C9	122.05 (14)	C21—C22—H22A	119.0
C10—C11—C12	123.65 (15)	C23—C22—H22A	119.0
C10—C11—C16	119.09 (15)	C10—C23—C22	122.83 (15)
C12—C11—C16	117.23 (15)	C10—C23—C18	119.92 (14)
C13—C12—C11	121.50 (16)	C22—C23—C18	117.22 (15)
C13—C12—H12A	119.3
C6—C1—C2—C3	−0.6 (3)	C12—C13—C14—C15	−2.3 (3)
Br1—C1—C2—C3	177.50 (13)	C13—C14—C15—C16	0.8 (3)
C1—C2—C3—C4	−0.8 (3)	C14—C15—C16—C17	−176.97 (17)
C2—C3—C4—C5	1.1 (3)	C14—C15—C16—C11	3.2 (3)
C3—C4—C5—C6	0.0 (2)	C10—C11—C16—C17	−3.5 (2)
C2—C1—C6—C5	1.7 (2)	C12—C11—C16—C17	174.62 (15)
Br1—C1—C6—C5	−176.39 (12)	C10—C11—C16—C15	176.38 (15)
C2—C1—C6—C7	−173.58 (15)	C12—C11—C16—C15	−5.5 (2)
Br1—C1—C6—C7	8.4 (2)	C15—C16—C17—C18	−179.59 (16)
C4—C5—C6—C1	−1.4 (2)	C11—C16—C17—C18	0.2 (3)
C4—C5—C6—C7	173.95 (15)	C16—C17—C18—C19	−178.97 (16)
C1—C6—C7—O1	58.3 (2)	C16—C17—C18—C23	2.2 (3)
C5—C6—C7—O1	−116.82 (18)	C17—C18—C19—C20	−178.01 (17)
C1—C6—C7—C8	−121.07 (17)	C23—C18—C19—C20	0.8 (3)
C5—C6—C7—C8	63.8 (2)	C18—C19—C20—C21	0.6 (3)
O1—C7—C8—C9	−173.96 (17)	C19—C20—C21—C22	−0.6 (3)
C6—C7—C8—C9	5.4 (3)	C20—C21—C22—C23	−0.9 (3)
C7—C8—C9—C10	174.24 (16)	C11—C10—C23—C22	−179.81 (15)
C8—C9—C10—C23	−137.39 (17)	C9—C10—C23—C22	−1.0 (2)
C8—C9—C10—C11	41.4 (3)	C11—C10—C23—C18	−1.8 (2)
C23—C10—C11—C12	−173.75 (15)	C9—C10—C23—C18	176.97 (15)
C9—C10—C11—C12	7.5 (2)	C21—C22—C23—C10	−179.72 (16)
C23—C10—C11—C16	4.2 (2)	C21—C22—C23—C18	2.2 (2)
C9—C10—C11—C16	−174.54 (15)	C17—C18—C23—C10	−1.4 (2)
C10—C11—C12—C13	−177.81 (16)	C19—C18—C23—C10	179.73 (15)
C16—C11—C12—C13	4.2 (2)	C17—C18—C23—C22	176.71 (15)
C11—C12—C13—C14	−0.4 (3)	C19—C18—C23—C22	−2.2 (2)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1i	0.93	2.53	3.301 (2)	140
C15—H15A···Cg1ii	0.93	2.99	3.6989 (19)	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O1i	0.93	2.53	3.301 (2)	140
C15—H15A⋯Cg1ii	0.93	2.99	3.6989 (19)	135

Symmetry codes: (i) ; (ii) .