(Z)-3-(9-Anthr-yl)-1-(4-methoxy-phen-yl)prop-2-en-1-one.

The title chalcone derivative, C(24)H(18)O(2), which consists of the substituted 4-methoxy-phenyl and anthracene rings bridged by the prop-2-en-1-one unit, exists in a cis configuration. The mol-ecule is twisted, the inter-planar angle between the benzene and anthracene rings being 69.50 (10)°. The meth-oxy group is coplanar with the attached benzene ring [C-O-C-C angle = 2.9 (3)°]. In the crystal structure, mol-ecules are linked into chains along the a axis by a weak C-H⋯O(enone) inter-action. The chains are stacked along the c axis. A C-H⋯π inter-action involving the benzene ring is observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2009 ▶); Suwunwong et al. (2009 ▶). For background to and applications of chalcones, see: Patil & Dharmaprakash (2008 ▶); Saydam et al. (2003 ▶); Svetlichny et al. (2007 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C24H18O2

M = 338.38

Monoclinic,

a = 5.5018 (2) Å

b = 19.9215 (8) Å

c = 16.0500 (7) Å

β = 95.072 (2)°

V = 1752.26 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.54 × 0.27 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.958, T max = 0.993

7966 measured reflections

1721 independent reflections

1545 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.087

S = 1.07

1721 reflections

236 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.14 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/S1600536809038665/sj2659sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038665/sj2659Isup2.hkl

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

C24H18O2	F(000) = 712
Mr = 338.38	Dx = 1.283 Mg m−3
Monoclinic, Cc	Melting point = 440–441 K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 5.5018 (2) Å	Cell parameters from 1721 reflections
b = 19.9215 (8) Å	θ = 2.0–26.0°
c = 16.0500 (7) Å	µ = 0.08 mm−1
β = 95.072 (2)°	T = 293 K
V = 1752.26 (12) Å3	Plate, yellow
Z = 4	0.54 × 0.27 × 0.09 mm

Bruker SMART APEXII CCD area-detector diffractometer	1721 independent reflections
Radiation source: fine-focus sealed tube	1545 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 8.33 pixels mm-1	θmax = 26.0°, θmin = 2.0°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −24→23
Tmin = 0.958, Tmax = 0.993	l = −19→19
7966 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0414P)2 + 0.4575P] where P = (Fo2 + 2Fc2)/3
1721 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.14 e Å−3
2 restraints	Δρmin = −0.14 e Å−3

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
O1	0.7379 (3)	0.26049 (10)	0.44324 (14)	0.0584 (5)
O2	0.5958 (4)	−0.04663 (10)	0.52663 (15)	0.0663 (6)
C1	0.3633 (5)	0.11209 (14)	0.43620 (17)	0.0469 (7)
H1A	0.2261	0.1294	0.4055	0.056*
C2	0.3691 (5)	0.04454 (15)	0.45676 (18)	0.0514 (7)
H2A	0.2382	0.0169	0.4394	0.062*
C3	0.5709 (5)	0.01859 (14)	0.50326 (17)	0.0469 (6)
C4	0.7641 (5)	0.06087 (14)	0.52870 (18)	0.0498 (7)
H4A	0.8992	0.0437	0.5607	0.060*
C5	0.7586 (4)	0.12742 (14)	0.50729 (17)	0.0448 (6)
H5A	0.8907	0.1548	0.5243	0.054*
C6	0.5565 (4)	0.15470 (13)	0.46010 (15)	0.0394 (6)
C7	0.5525 (4)	0.22645 (13)	0.43565 (16)	0.0413 (6)
C8	0.3147 (4)	0.25664 (13)	0.40406 (18)	0.0454 (6)
H8A	0.1795	0.2456	0.4322	0.054*
C9	0.2783 (5)	0.29786 (13)	0.33936 (17)	0.0451 (6)
H9A	0.1214	0.3150	0.3286	0.054*
C10	0.4614 (4)	0.31959 (13)	0.28220 (16)	0.0411 (6)
C11	0.5862 (5)	0.27224 (13)	0.23652 (16)	0.0428 (6)
C12	0.5348 (6)	0.20192 (15)	0.23660 (18)	0.0527 (7)
H12A	0.4126	0.1859	0.2678	0.063*
C13	0.6601 (6)	0.15829 (16)	0.1923 (2)	0.0634 (9)
H13A	0.6205	0.1129	0.1927	0.076*
C14	0.8495 (7)	0.18016 (18)	0.1455 (2)	0.0670 (9)
H14A	0.9371	0.1492	0.1167	0.080*
C15	0.9040 (6)	0.24607 (17)	0.14224 (18)	0.0580 (8)
H15A	1.0296	0.2601	0.1112	0.070*
C16	0.7721 (5)	0.29480 (14)	0.18577 (15)	0.0460 (6)
C17	0.8194 (5)	0.36309 (15)	0.17973 (16)	0.0491 (7)
H17A	0.9427	0.3773	0.1478	0.059*
C18	0.6874 (5)	0.41081 (14)	0.22015 (16)	0.0463 (7)
C19	0.7276 (6)	0.48094 (15)	0.21182 (19)	0.0559 (8)
H19A	0.8496	0.4957	0.1796	0.067*
C20	0.5933 (6)	0.52656 (16)	0.2495 (2)	0.0622 (8)
H20A	0.6211	0.5721	0.2422	0.075*
C21	0.4106 (6)	0.50528 (17)	0.2999 (2)	0.0616 (8)
H21A	0.3169	0.5370	0.3251	0.074*
C22	0.3704 (5)	0.43918 (16)	0.31209 (18)	0.0529 (7)
H22A	0.2533	0.4263	0.3473	0.063*
C23	0.5028 (5)	0.38878 (13)	0.27229 (16)	0.0426 (6)
C24	0.4045 (7)	−0.09228 (16)	0.4985 (3)	0.0761 (10)
H24A	0.4477	−0.1368	0.5173	0.114*
H24B	0.3820	−0.0916	0.4385	0.114*
H24C	0.2557	−0.0790	0.5209	0.114*

	U11	U22	U33	U12	U13	U23
O1	0.0426 (10)	0.0571 (12)	0.0750 (14)	−0.0105 (10)	0.0021 (9)	0.0098 (11)
O2	0.0777 (15)	0.0442 (12)	0.0741 (15)	−0.0021 (11)	−0.0085 (12)	0.0055 (11)
C1	0.0362 (13)	0.0538 (17)	0.0499 (15)	−0.0038 (12)	−0.0007 (11)	0.0081 (13)
C2	0.0466 (15)	0.0532 (17)	0.0532 (16)	−0.0111 (13)	−0.0017 (13)	0.0015 (13)
C3	0.0513 (15)	0.0464 (16)	0.0435 (15)	0.0022 (12)	0.0071 (12)	0.0015 (12)
C4	0.0450 (15)	0.0519 (17)	0.0514 (16)	0.0072 (13)	−0.0026 (12)	0.0011 (13)
C5	0.0340 (13)	0.0535 (16)	0.0471 (15)	−0.0037 (12)	0.0041 (11)	−0.0032 (12)
C6	0.0337 (12)	0.0493 (16)	0.0365 (13)	−0.0027 (11)	0.0101 (10)	0.0015 (11)
C7	0.0372 (13)	0.0498 (15)	0.0387 (13)	−0.0049 (12)	0.0132 (11)	0.0020 (12)
C8	0.0357 (13)	0.0479 (15)	0.0543 (16)	−0.0020 (12)	0.0133 (11)	0.0064 (13)
C9	0.0363 (13)	0.0449 (16)	0.0542 (15)	0.0019 (11)	0.0042 (11)	0.0035 (13)
C10	0.0381 (13)	0.0470 (16)	0.0377 (13)	−0.0006 (11)	−0.0003 (10)	0.0045 (11)
C11	0.0459 (14)	0.0439 (15)	0.0376 (13)	0.0007 (11)	−0.0018 (11)	0.0044 (12)
C12	0.0589 (17)	0.0486 (16)	0.0505 (16)	−0.0023 (14)	0.0040 (14)	0.0033 (14)
C13	0.084 (2)	0.0470 (17)	0.0592 (18)	0.0052 (16)	0.0048 (17)	−0.0025 (15)
C14	0.084 (2)	0.063 (2)	0.0557 (18)	0.0208 (18)	0.0146 (17)	−0.0049 (16)
C15	0.0646 (19)	0.068 (2)	0.0430 (16)	0.0071 (16)	0.0165 (14)	0.0037 (14)
C16	0.0495 (16)	0.0547 (17)	0.0335 (13)	0.0020 (13)	0.0015 (11)	0.0041 (12)
C17	0.0483 (15)	0.0615 (19)	0.0384 (14)	−0.0058 (13)	0.0083 (12)	0.0093 (13)
C18	0.0499 (15)	0.0505 (17)	0.0370 (13)	−0.0056 (13)	−0.0043 (12)	0.0073 (12)
C19	0.0635 (19)	0.0537 (19)	0.0496 (16)	−0.0158 (15)	0.0000 (14)	0.0084 (14)
C20	0.079 (2)	0.0415 (17)	0.063 (2)	−0.0042 (16)	−0.0104 (17)	0.0035 (15)
C21	0.070 (2)	0.0494 (19)	0.0640 (19)	0.0076 (15)	−0.0005 (16)	−0.0029 (15)
C22	0.0531 (16)	0.0531 (19)	0.0520 (17)	0.0021 (14)	0.0027 (13)	0.0015 (14)
C23	0.0438 (14)	0.0436 (15)	0.0390 (13)	−0.0005 (12)	−0.0037 (11)	0.0029 (11)
C24	0.093 (3)	0.052 (2)	0.082 (2)	−0.0170 (18)	−0.003 (2)	0.0025 (18)

O1—C7	1.222 (3)	C12—H12A	0.9300
O2—C3	1.356 (3)	C13—C14	1.407 (5)
O2—C24	1.433 (4)	C13—H13A	0.9300
C1—C2	1.385 (4)	C14—C15	1.349 (5)
C1—C6	1.387 (4)	C14—H14A	0.9300
C1—H1A	0.9300	C15—C16	1.431 (4)
C2—C3	1.382 (4)	C15—H15A	0.9300
C2—H2A	0.9300	C16—C17	1.390 (4)
C3—C4	1.389 (4)	C17—C18	1.391 (4)
C4—C5	1.369 (4)	C17—H17A	0.9300
C4—H4A	0.9300	C18—C19	1.423 (4)
C5—C6	1.399 (4)	C18—C23	1.440 (4)
C5—H5A	0.9300	C19—C20	1.348 (5)
C6—C7	1.482 (4)	C19—H19A	0.9300
C7—C8	1.488 (4)	C20—C21	1.411 (5)
C8—C9	1.325 (4)	C20—H20A	0.9300
C8—H8A	0.9300	C21—C22	1.352 (5)
C9—C10	1.486 (4)	C21—H21A	0.9300
C9—H9A	0.9300	C22—C23	1.425 (4)
C10—C23	1.408 (4)	C22—H22A	0.9300
C10—C11	1.410 (4)	C24—H24A	0.9600
C11—C12	1.429 (4)	C24—H24B	0.9600
C11—C16	1.435 (4)	C24—H24C	0.9600
C12—C13	1.350 (4)
C3—O2—C24	117.9 (2)	C12—C13—H13A	119.4
C2—C1—C6	121.8 (3)	C14—C13—H13A	119.4
C2—C1—H1A	119.1	C15—C14—C13	120.0 (3)
C6—C1—H1A	119.1	C15—C14—H14A	120.0
C3—C2—C1	119.5 (3)	C13—C14—H14A	120.0
C3—C2—H2A	120.2	C14—C15—C16	121.2 (3)
C1—C2—H2A	120.2	C14—C15—H15A	119.4
O2—C3—C2	124.4 (3)	C16—C15—H15A	119.4
O2—C3—C4	116.4 (2)	C17—C16—C15	121.6 (3)
C2—C3—C4	119.3 (3)	C17—C16—C11	119.5 (2)
C5—C4—C3	120.9 (2)	C15—C16—C11	118.9 (3)
C5—C4—H4A	119.5	C16—C17—C18	121.9 (2)
C3—C4—H4A	119.5	C16—C17—H17A	119.1
C4—C5—C6	120.7 (2)	C18—C17—H17A	119.1
C4—C5—H5A	119.6	C17—C18—C19	122.4 (3)
C6—C5—H5A	119.6	C17—C18—C23	119.1 (2)
C1—C6—C5	117.7 (2)	C19—C18—C23	118.5 (3)
C1—C6—C7	121.6 (2)	C20—C19—C18	121.6 (3)
C5—C6—C7	120.7 (2)	C20—C19—H19A	119.2
O1—C7—C6	121.1 (2)	C18—C19—H19A	119.2
O1—C7—C8	120.7 (2)	C19—C20—C21	120.1 (3)
C6—C7—C8	118.2 (2)	C19—C20—H20A	119.9
C9—C8—C7	125.8 (2)	C21—C20—H20A	119.9
C9—C8—H8A	117.1	C22—C21—C20	120.6 (3)
C7—C8—H8A	117.1	C22—C21—H21A	119.7
C8—C9—C10	126.9 (2)	C20—C21—H21A	119.7
C8—C9—H9A	116.5	C21—C22—C23	121.7 (3)
C10—C9—H9A	116.5	C21—C22—H22A	119.2
C23—C10—C11	120.3 (2)	C23—C22—H22A	119.2
C23—C10—C9	118.7 (2)	C10—C23—C22	123.0 (2)
C11—C10—C9	120.9 (2)	C10—C23—C18	119.6 (2)
C10—C11—C12	123.4 (2)	C22—C23—C18	117.4 (2)
C10—C11—C16	119.3 (2)	O2—C24—H24A	109.5
C12—C11—C16	117.3 (2)	O2—C24—H24B	109.5
C13—C12—C11	121.4 (3)	H24A—C24—H24B	109.5
C13—C12—H12A	119.3	O2—C24—H24C	109.5
C11—C12—H12A	119.3	H24A—C24—H24C	109.5
C12—C13—C14	121.2 (3)	H24B—C24—H24C	109.5
C6—C1—C2—C3	0.8 (4)	C12—C13—C14—C15	−2.0 (5)
C24—O2—C3—C2	2.6 (4)	C13—C14—C15—C16	0.0 (5)
C24—O2—C3—C4	−177.4 (3)	C14—C15—C16—C17	−177.0 (3)
C1—C2—C3—O2	−179.8 (3)	C14—C15—C16—C11	2.8 (4)
C1—C2—C3—C4	0.1 (4)	C10—C11—C16—C17	−2.6 (4)
O2—C3—C4—C5	179.0 (3)	C12—C11—C16—C17	176.3 (2)
C2—C3—C4—C5	−1.0 (4)	C10—C11—C16—C15	177.6 (2)
C3—C4—C5—C6	0.8 (4)	C12—C11—C16—C15	−3.4 (3)
C2—C1—C6—C5	−1.0 (4)	C15—C16—C17—C18	178.3 (2)
C2—C1—C6—C7	178.0 (2)	C11—C16—C17—C18	−1.5 (4)
C4—C5—C6—C1	0.1 (4)	C16—C17—C18—C19	−177.5 (3)
C4—C5—C6—C7	−178.9 (2)	C16—C17—C18—C23	2.4 (4)
C1—C6—C7—O1	−166.3 (3)	C17—C18—C19—C20	178.0 (3)
C5—C6—C7—O1	12.6 (4)	C23—C18—C19—C20	−1.8 (4)
C1—C6—C7—C8	15.6 (4)	C18—C19—C20—C21	1.2 (5)
C5—C6—C7—C8	−165.4 (2)	C19—C20—C21—C22	0.9 (5)
O1—C7—C8—C9	44.5 (4)	C20—C21—C22—C23	−2.5 (5)
C6—C7—C8—C9	−137.5 (3)	C11—C10—C23—C22	175.5 (2)
C7—C8—C9—C10	3.6 (5)	C9—C10—C23—C22	−2.5 (4)
C8—C9—C10—C23	−124.0 (3)	C11—C10—C23—C18	−4.8 (3)
C8—C9—C10—C11	58.1 (4)	C9—C10—C23—C18	177.2 (2)
C23—C10—C11—C12	−173.1 (2)	C21—C22—C23—C10	−178.5 (3)
C9—C10—C11—C12	4.8 (4)	C21—C22—C23—C18	1.8 (4)
C23—C10—C11—C16	5.7 (4)	C17—C18—C23—C10	0.8 (3)
C9—C10—C11—C16	−176.3 (2)	C19—C18—C23—C10	−179.3 (2)
C10—C11—C12—C13	−179.6 (3)	C17—C18—C23—C22	−179.5 (2)
C16—C11—C12—C13	1.5 (4)	C19—C18—C23—C22	0.4 (3)
C11—C12—C13—C14	1.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1i	0.93	2.47	3.290 (3)	147
C24—H24A···O1ii	0.96	2.59	3.176 (4)	120
C17—H17A···Cg1iii	0.93	2.89	3.694 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1i	0.93	2.47	3.290 (3)	147
C24—H24A⋯O1ii	0.96	2.59	3.176 (4)	120
C17—H17A⋯Cg1iii	0.93	2.89	3.694 (3)	145

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 ring.