(E)-3-(Anthracen-9-yl)-1-(4-bromo-phen-yl)prop-2-en-1-one.

In the title mol-ecule, C(23)H(15)BrO, the prop-2-en-1-one unit is planar and it makes dihedral angles of 20.9 (1) and 45.8 (1)°, respectively, with the 4-bromo-phenyl ring and the anthracene ring system. The interplanar angle between the 4-bromophenyl ring and the anthracene ring system is 35.52 (7)°. In the crystal structure, mol-ecules are linked into dimers by C-H⋯Br hydrogen bonds, and the dimers are linked into a zigzag network parallel to the bc plane by weak C-H⋯O hydrogen bonds and C-H⋯π inter-actions involving the central benzene ring of the anthracene ring system.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Ng et al. (2006 ▶); Patil et al. (2006 ▶); Patil, Chantrapromma et al. (2007 ▶); Suwunwong et al. (2009 ▶). For background and applications of chalcones, see: Jung et al. (2008 ▶); Patil, Chantrapromma et al. (2007 ▶); Patil, Dharmaprakash et al. (2007 ▶); Patil & Dharmaprakash (2008 ▶); Prasad et al. (2008 ▶).

Experimental

Crystal data

C23H15BrO

M = 387.25

Monoclinic,

a = 5.3792 (1) Å

b = 19.1030 (4) Å

c = 16.3005 (4) Å

β = 95.944 (1)°

V = 1666.02 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.47 mm−1

T = 100.0 (1) K

0.57 × 0.27 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.331, T max = 0.714

29994 measured reflections

4866 independent reflections

3803 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.076

S = 1.02

4866 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.54 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003122/ci2756sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003122/ci2756Isup2.hkl

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

C23H15BrO	F(000) = 784
Mr = 387.25	Dx = 1.544 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4866 reflections
a = 5.3792 (1) Å	θ = 2.1–30.0°
b = 19.1030 (4) Å	µ = 2.47 mm−1
c = 16.3005 (4) Å	T = 100 K
β = 95.944 (1)°	Plate, yellow
V = 1666.02 (6) Å3	0.57 × 0.27 × 0.15 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4866 independent reflections
Radiation source: fine-focus sealed tube	3803 reflections with I > 2σ(I)
graphite	Rint = 0.036
Detector resolution: 8.33 pixels mm-1	θmax = 30.0°, θmin = 2.1°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −26→26
Tmin = 0.331, Tmax = 0.714	l = −22→22
29994 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0322P)2 + 1.1607P] where P = (Fo2 + 2Fc2)/3
4866 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.32584 (4)	0.344013 (10)	0.411244 (11)	0.02530 (7)
O1	0.9073 (2)	0.51056 (7)	0.74450 (8)	0.0213 (3)
C1	0.7274 (4)	0.41439 (9)	0.62533 (11)	0.0201 (4)
H1A	0.8800	0.4043	0.6552	0.024*
C2	0.6526 (4)	0.37631 (10)	0.55484 (12)	0.0219 (4)
H2A	0.7530	0.3408	0.5374	0.026*
C3	0.4261 (4)	0.39203 (9)	0.51095 (10)	0.0180 (4)
C4	0.2711 (4)	0.44314 (10)	0.53719 (11)	0.0206 (4)
H4A	0.1176	0.4523	0.5075	0.025*
C5	0.3464 (3)	0.48075 (10)	0.60836 (10)	0.0184 (4)
H5A	0.2419	0.5149	0.6267	0.022*
C6	0.5781 (3)	0.46766 (9)	0.65244 (10)	0.0152 (3)
C7	0.6813 (3)	0.51052 (9)	0.72478 (10)	0.0159 (3)
C8	0.5083 (3)	0.55087 (9)	0.77158 (10)	0.0159 (3)
H8A	0.3374	0.5499	0.7555	0.019*
C9	0.5978 (3)	0.58858 (9)	0.83690 (10)	0.0161 (3)
H9A	0.7707	0.5920	0.8471	0.019*
C10	0.4492 (3)	0.62533 (9)	0.89440 (10)	0.0158 (3)
C11	0.5151 (3)	0.61533 (9)	0.98020 (10)	0.0157 (3)
C12	0.7151 (4)	0.57046 (10)	1.01164 (11)	0.0195 (4)
H12A	0.8015	0.5452	0.9749	0.023*
C13	0.7822 (4)	0.56385 (10)	1.09428 (11)	0.0219 (4)
H13A	0.9149	0.5349	1.1132	0.026*
C14	0.6506 (4)	0.60082 (10)	1.15145 (11)	0.0220 (4)
H14A	0.7002	0.5970	1.2076	0.026*
C15	0.4527 (4)	0.64183 (10)	1.12478 (11)	0.0224 (4)
H15A	0.3652	0.6648	1.1631	0.027*
C16	0.3767 (3)	0.65030 (9)	1.03860 (10)	0.0169 (3)
C17	0.1715 (4)	0.69108 (9)	1.01020 (10)	0.0187 (4)
H17A	0.0769	0.7118	1.0482	0.022*
C18	0.1036 (3)	0.70178 (9)	0.92633 (10)	0.0167 (3)
C19	−0.1040 (4)	0.74534 (9)	0.89840 (11)	0.0196 (4)
H19A	−0.2054	0.7629	0.9365	0.023*
C20	−0.1560 (4)	0.76158 (9)	0.81740 (11)	0.0211 (4)
H20A	−0.2925	0.7898	0.8002	0.025*
C21	−0.0008 (4)	0.73530 (9)	0.75909 (11)	0.0205 (4)
H21A	−0.0309	0.7487	0.7041	0.025*
C22	0.1913 (3)	0.69077 (9)	0.78224 (10)	0.0184 (4)
H22A	0.2862	0.6730	0.7424	0.022*
C23	0.2504 (3)	0.67066 (9)	0.86689 (10)	0.0153 (3)

	U11	U22	U33	U12	U13	U23
Br1	0.03907 (13)	0.02093 (10)	0.01575 (9)	−0.00663 (8)	0.00217 (7)	−0.00386 (7)
O1	0.0137 (7)	0.0297 (7)	0.0203 (6)	0.0009 (5)	0.0009 (5)	−0.0031 (5)
C1	0.0181 (10)	0.0199 (9)	0.0219 (9)	0.0037 (7)	0.0000 (7)	−0.0002 (7)
C2	0.0238 (10)	0.0180 (9)	0.0239 (9)	0.0060 (7)	0.0029 (7)	−0.0027 (7)
C3	0.0238 (10)	0.0159 (8)	0.0146 (8)	−0.0052 (7)	0.0032 (6)	−0.0018 (6)
C4	0.0170 (10)	0.0258 (9)	0.0182 (8)	−0.0003 (7)	−0.0010 (7)	−0.0016 (7)
C5	0.0158 (9)	0.0228 (9)	0.0168 (8)	0.0022 (7)	0.0020 (6)	−0.0031 (7)
C6	0.0155 (9)	0.0169 (8)	0.0134 (7)	−0.0013 (6)	0.0024 (6)	0.0007 (6)
C7	0.0156 (9)	0.0176 (8)	0.0148 (7)	−0.0011 (7)	0.0027 (6)	0.0005 (6)
C8	0.0119 (9)	0.0206 (8)	0.0155 (7)	−0.0010 (7)	0.0022 (6)	−0.0008 (6)
C9	0.0133 (9)	0.0179 (8)	0.0175 (8)	−0.0016 (7)	0.0032 (6)	0.0007 (6)
C10	0.0157 (9)	0.0163 (8)	0.0155 (8)	−0.0035 (7)	0.0024 (6)	−0.0019 (6)
C11	0.0163 (9)	0.0155 (8)	0.0154 (8)	−0.0034 (7)	0.0018 (6)	−0.0006 (6)
C12	0.0195 (10)	0.0211 (9)	0.0184 (8)	−0.0005 (7)	0.0034 (7)	−0.0008 (7)
C13	0.0209 (10)	0.0240 (9)	0.0202 (8)	−0.0003 (8)	−0.0003 (7)	0.0026 (7)
C14	0.0292 (11)	0.0223 (9)	0.0140 (8)	−0.0036 (8)	−0.0004 (7)	0.0005 (7)
C15	0.0307 (11)	0.0227 (9)	0.0141 (8)	−0.0017 (8)	0.0042 (7)	−0.0017 (7)
C16	0.0210 (9)	0.0144 (8)	0.0156 (8)	−0.0040 (7)	0.0036 (6)	−0.0015 (6)
C17	0.0225 (10)	0.0168 (8)	0.0175 (8)	−0.0003 (7)	0.0054 (7)	−0.0032 (6)
C18	0.0182 (9)	0.0142 (8)	0.0178 (8)	−0.0032 (7)	0.0021 (6)	−0.0015 (6)
C19	0.0193 (10)	0.0156 (8)	0.0244 (9)	−0.0002 (7)	0.0050 (7)	−0.0024 (7)
C20	0.0200 (10)	0.0160 (8)	0.0266 (9)	−0.0010 (7)	−0.0018 (7)	0.0006 (7)
C21	0.0216 (10)	0.0209 (9)	0.0182 (8)	−0.0033 (7)	−0.0016 (7)	0.0014 (7)
C22	0.0192 (10)	0.0191 (9)	0.0168 (8)	−0.0029 (7)	0.0020 (6)	−0.0020 (7)
C23	0.0155 (9)	0.0154 (8)	0.0150 (7)	−0.0048 (6)	0.0013 (6)	−0.0018 (6)

Br1—C3	1.8954 (17)	C12—C13	1.364 (2)
O1—C7	1.225 (2)	C12—H12A	0.93
C1—C2	1.384 (3)	C13—C14	1.416 (3)
C1—C6	1.396 (2)	C13—H13A	0.93
C1—H1A	0.93	C14—C15	1.356 (3)
C2—C3	1.380 (3)	C14—H14A	0.93
C2—H2A	0.93	C15—C16	1.431 (2)
C3—C4	1.380 (3)	C15—H15A	0.93
C4—C5	1.389 (2)	C16—C17	1.391 (3)
C4—H4A	0.93	C17—C18	1.393 (2)
C5—C6	1.395 (2)	C17—H17A	0.93
C5—H5A	0.93	C18—C19	1.429 (3)
C6—C7	1.495 (2)	C18—C23	1.440 (2)
C7—C8	1.480 (2)	C19—C20	1.357 (3)
C8—C9	1.333 (2)	C19—H19A	0.93
C8—H8A	0.93	C20—C21	1.420 (3)
C9—C10	1.472 (2)	C20—H20A	0.93
C9—H9A	0.93	C21—C22	1.361 (3)
C10—C23	1.413 (3)	C21—H21A	0.93
C10—C11	1.420 (2)	C22—C23	1.436 (2)
C11—C12	1.428 (3)	C22—H22A	0.93
C11—C16	1.433 (2)
C2—C1—C6	121.23 (17)	C11—C12—H12A	119.3
C2—C1—H1A	119.4	C12—C13—C14	120.32 (18)
C6—C1—H1A	119.4	C12—C13—H13A	119.8
C3—C2—C1	118.75 (17)	C14—C13—H13A	119.8
C3—C2—H2A	120.6	C15—C14—C13	120.41 (17)
C1—C2—H2A	120.6	C15—C14—H14A	119.8
C4—C3—C2	121.49 (16)	C13—C14—H14A	119.8
C4—C3—Br1	118.73 (14)	C14—C15—C16	121.00 (17)
C2—C3—Br1	119.78 (14)	C14—C15—H15A	119.5
C3—C4—C5	119.44 (17)	C16—C15—H15A	119.5
C3—C4—H4A	120.3	C17—C16—C15	121.78 (16)
C5—C4—H4A	120.3	C17—C16—C11	119.28 (16)
C4—C5—C6	120.34 (17)	C15—C16—C11	118.94 (17)
C4—C5—H5A	119.8	C16—C17—C18	121.81 (16)
C6—C5—H5A	119.8	C16—C17—H17A	119.1
C5—C6—C1	118.69 (16)	C18—C17—H17A	119.1
C5—C6—C7	123.18 (16)	C17—C18—C19	120.98 (16)
C1—C6—C7	118.04 (16)	C17—C18—C23	119.57 (16)
O1—C7—C8	121.62 (16)	C19—C18—C23	119.41 (15)
O1—C7—C6	119.02 (15)	C20—C19—C18	121.24 (17)
C8—C7—C6	119.35 (15)	C20—C19—H19A	119.4
C9—C8—C7	119.93 (16)	C18—C19—H19A	119.4
C9—C8—H8A	120.0	C19—C20—C21	119.62 (18)
C7—C8—H8A	120.0	C19—C20—H20A	120.2
C8—C9—C10	126.25 (17)	C21—C20—H20A	120.2
C8—C9—H9A	116.9	C22—C21—C20	121.16 (16)
C10—C9—H9A	116.9	C22—C21—H21A	119.4
C23—C10—C11	119.94 (15)	C20—C21—H21A	119.4
C23—C10—C9	122.24 (15)	C21—C22—C23	121.31 (17)
C11—C10—C9	117.80 (16)	C21—C22—H22A	119.3
C10—C11—C12	122.43 (16)	C23—C22—H22A	119.3
C10—C11—C16	119.84 (16)	C10—C23—C22	123.65 (16)
C12—C11—C16	117.72 (15)	C10—C23—C18	119.29 (15)
C13—C12—C11	121.49 (17)	C22—C23—C18	116.99 (16)
C13—C12—H12A	119.3
C6—C1—C2—C3	0.3 (3)	C13—C14—C15—C16	−1.8 (3)
C1—C2—C3—C4	−1.9 (3)	C14—C15—C16—C17	178.78 (18)
C1—C2—C3—Br1	176.90 (14)	C14—C15—C16—C11	−0.8 (3)
C2—C3—C4—C5	1.4 (3)	C10—C11—C16—C17	3.0 (3)
Br1—C3—C4—C5	−177.43 (14)	C12—C11—C16—C17	−176.19 (16)
C3—C4—C5—C6	0.8 (3)	C10—C11—C16—C15	−177.41 (16)
C4—C5—C6—C1	−2.4 (3)	C12—C11—C16—C15	3.4 (2)
C4—C5—C6—C7	174.05 (17)	C15—C16—C17—C18	177.22 (17)
C2—C1—C6—C5	1.9 (3)	C11—C16—C17—C18	−3.2 (3)
C2—C1—C6—C7	−174.75 (17)	C16—C17—C18—C19	−178.36 (17)
C5—C6—C7—O1	−158.07 (17)	C16—C17—C18—C23	−0.7 (3)
C1—C6—C7—O1	18.4 (2)	C17—C18—C19—C20	173.37 (17)
C5—C6—C7—C8	22.9 (2)	C23—C18—C19—C20	−4.3 (3)
C1—C6—C7—C8	−160.59 (16)	C18—C19—C20—C21	−0.4 (3)
O1—C7—C8—C9	0.1 (3)	C19—C20—C21—C22	3.8 (3)
C6—C7—C8—C9	179.10 (16)	C20—C21—C22—C23	−2.3 (3)
C7—C8—C9—C10	−173.26 (16)	C11—C10—C23—C22	171.79 (16)
C8—C9—C10—C23	−50.2 (3)	C9—C10—C23—C22	−6.7 (3)
C8—C9—C10—C11	131.30 (19)	C11—C10—C23—C18	−5.1 (3)
C23—C10—C11—C12	−179.68 (17)	C9—C10—C23—C18	176.46 (16)
C9—C10—C11—C12	−1.1 (3)	C21—C22—C23—C10	−179.25 (18)
C23—C10—C11—C16	1.1 (3)	C21—C22—C23—C18	−2.3 (3)
C9—C10—C11—C16	179.69 (16)	C17—C18—C23—C10	4.9 (3)
C10—C11—C12—C13	177.21 (17)	C19—C18—C23—C10	−177.42 (16)
C16—C11—C12—C13	−3.6 (3)	C17—C18—C23—C22	−172.15 (16)
C11—C12—C13—C14	1.1 (3)	C19—C18—C23—C22	5.5 (2)
C12—C13—C14—C15	1.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1i	0.93	2.42	3.308 (2)	159
C13—H13A···O1ii	0.93	2.57	3.288 (2)	135
C21—H21A···Br1iii	0.93	2.93	3.4722 (19)	119
C9—H9A···Cg1iv	0.93	2.83	3.4479 (18)	125

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1i	0.93	2.42	3.308 (2)	159
C13—H13A⋯O1ii	0.93	2.57	3.288 (2)	135
C21—H21A⋯Br1iii	0.93	2.93	3.4722 (19)	119
C9—H9A⋯Cg1iv	0.93	2.83	3.4479 (18)	125

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .