(Z)-3-(Anthracen-9-yl)-1-(2-eth-oxy-phen-yl)prop-2-en-1-one.

The mol-ecule of the title chalcone, C(25)H(20)O(2), consisting of 2-eth-oxy-phenyl and anthracene rings bridged by a prop-2-en-1-one unit, is twisted and exists in the Z configuration with respect to the central C=C bond. The dihedral angle between the benzene and anthracene rings is 78.17 (9)°. The propene unit makes dihedral angles of 44.5 (2) and 81.1 (2)° with the benzene and anthracene rings, respectively. The eth-oxy substituent is almost coplanar with the attached benzene ring [C-O-C-C torsion angle = 178.57 (19)°]. In the crystal, mol-ecules are linked into chains along the a axis by weak C-H⋯O inter-actions. 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: Chantrapromma et al. (2009 ▶, 2010 ▶); Suwunwong et al. (2009 ▶). For background to and applications of chalcones, see: Kobkeatthawin et al. (2010 ▶); Nowakowska (2007 ▶); Oliveira et al. (2007 ▶); Patil & Dharmaprakash (2008 ▶); Saydam et al. (2003 ▶); Svetlichny et al. (2007 ▶); Tewtrakul et al. (2003 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C25H20O2

M = 352.41

Orthorhombic,

a = 5.4442 (1) Å

b = 10.7665 (2) Å

c = 32.2160 (7) Å

V = 1888.34 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.47 × 0.16 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.964, T max = 0.995

18936 measured reflections

3190 independent reflections

2632 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.102

S = 1.04

3190 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.19 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/S1600536810038183/rz2490sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038183/rz2490Isup2.hkl

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

C25H20O2	Dx = 1.240 Mg m−3
Mr = 352.41	Melting point = 419–421 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3190 reflections
a = 5.4442 (1) Å	θ = 2.0–30.0°
b = 10.7665 (2) Å	µ = 0.08 mm−1
c = 32.2160 (7) Å	T = 100 K
V = 1888.34 (6) Å3	Plate, yellow
Z = 4	0.47 × 0.16 × 0.07 mm
F(000) = 744

Bruker APEXII CCD area-detector diffractometer	3190 independent reflections
Radiation source: sealed tube	2632 reflections with I > 2σ(I)
graphite	Rint = 0.055
φ and ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
Tmin = 0.964, Tmax = 0.995	k = −13→15
18936 measured reflections	l = −38→45

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.042P)2 + 0.4942P] where P = (Fo2 + 2Fc2)/3
3190 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.19 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
O1	−0.0044 (2)	0.12896 (14)	0.83325 (4)	0.0251 (3)
O2	0.5039 (3)	−0.11326 (13)	0.80475 (4)	0.0281 (3)
C1	0.3555 (4)	−0.08224 (18)	0.77249 (6)	0.0222 (4)
C2	0.3530 (4)	−0.1433 (2)	0.73429 (6)	0.0290 (5)
H2A	0.4665	−0.2057	0.7288	0.035*
C3	0.1806 (4)	−0.1105 (2)	0.70459 (6)	0.0311 (5)
H3A	0.1805	−0.1508	0.6791	0.037*
C4	0.0084 (4)	−0.0187 (2)	0.71237 (6)	0.0290 (4)
H4A	−0.1093	0.0013	0.6925	0.035*
C5	0.0135 (4)	0.04316 (19)	0.75010 (6)	0.0242 (4)
H5A	−0.1019	0.1048	0.7554	0.029*
C6	0.1884 (3)	0.01477 (17)	0.78025 (5)	0.0187 (4)
C7	0.1887 (3)	0.08877 (17)	0.81949 (6)	0.0174 (4)
C8	0.4287 (3)	0.11964 (17)	0.83872 (6)	0.0175 (4)
H8A	0.5698	0.1084	0.8229	0.021*
C9	0.4541 (3)	0.16241 (17)	0.87726 (6)	0.0193 (4)
H9A	0.6114	0.1843	0.8858	0.023*
C10	0.2511 (3)	0.17797 (19)	0.90773 (5)	0.0194 (4)
C11	0.1582 (3)	0.07403 (18)	0.92908 (6)	0.0207 (4)
C12	0.2619 (4)	−0.04731 (19)	0.92423 (6)	0.0261 (4)
H12A	0.3957	−0.0585	0.9067	0.031*
C13	0.1672 (5)	−0.1464 (2)	0.94501 (7)	0.0326 (5)
H13A	0.2386	−0.2243	0.9419	0.039*
C14	−0.0399 (5)	−0.1318 (2)	0.97134 (7)	0.0352 (5)
H14A	−0.1049	−0.2006	0.9849	0.042*
C15	−0.1435 (4)	−0.0192 (2)	0.97689 (6)	0.0317 (5)
H15A	−0.2787	−0.0115	0.9943	0.038*
C16	−0.0488 (4)	0.0885 (2)	0.95640 (6)	0.0244 (4)
C17	−0.1518 (4)	0.2059 (2)	0.96189 (6)	0.0264 (4)
H17A	−0.2869	0.2147	0.9793	0.032*
C18	−0.0574 (3)	0.3102 (2)	0.94196 (6)	0.0239 (4)
C19	−0.1629 (4)	0.4308 (2)	0.94695 (6)	0.0304 (5)
H19A	−0.2990	0.4406	0.9641	0.036*
C20	−0.0687 (4)	0.5313 (2)	0.92721 (7)	0.0337 (5)
H20A	−0.1417	0.6087	0.9306	0.040*
C21	0.1408 (4)	0.5188 (2)	0.90134 (6)	0.0301 (5)
H21A	0.2072	0.5887	0.8886	0.036*
C22	0.2456 (4)	0.40556 (19)	0.89496 (6)	0.0243 (4)
H22A	0.3804	0.3988	0.8774	0.029*
C23	0.1515 (3)	0.29688 (19)	0.91489 (6)	0.0211 (4)
C24	0.6799 (4)	−0.2118 (2)	0.79972 (7)	0.0326 (5)
H24A	0.7919	−0.1932	0.7771	0.039*
H24C	0.5973	−0.2896	0.7937	0.039*
C25	0.8164 (5)	−0.2200 (2)	0.84010 (8)	0.0457 (6)
H25C	0.9491	−0.2782	0.8374	0.069*
H25A	0.7066	−0.2473	0.8616	0.069*
H25B	0.8810	−0.1397	0.8472	0.069*

	U11	U22	U33	U12	U13	U23
O1	0.0146 (5)	0.0381 (8)	0.0226 (7)	0.0038 (6)	−0.0007 (5)	−0.0056 (6)
O2	0.0291 (7)	0.0251 (7)	0.0299 (7)	0.0092 (6)	−0.0045 (6)	−0.0046 (6)
C1	0.0216 (8)	0.0224 (9)	0.0226 (9)	−0.0010 (7)	0.0011 (8)	−0.0015 (8)
C2	0.0299 (10)	0.0262 (10)	0.0310 (11)	−0.0021 (9)	0.0050 (9)	−0.0109 (9)
C3	0.0395 (11)	0.0340 (12)	0.0199 (10)	−0.0130 (10)	0.0033 (9)	−0.0074 (9)
C4	0.0300 (10)	0.0369 (11)	0.0200 (9)	−0.0085 (10)	−0.0058 (8)	0.0006 (9)
C5	0.0207 (8)	0.0299 (10)	0.0221 (9)	−0.0045 (8)	−0.0010 (8)	−0.0010 (8)
C6	0.0161 (8)	0.0231 (9)	0.0170 (8)	−0.0028 (7)	0.0015 (7)	−0.0006 (7)
C7	0.0150 (7)	0.0214 (9)	0.0160 (8)	0.0003 (7)	−0.0002 (7)	0.0013 (7)
C8	0.0119 (7)	0.0207 (9)	0.0198 (9)	0.0012 (6)	0.0013 (6)	0.0015 (8)
C9	0.0127 (7)	0.0260 (9)	0.0190 (9)	−0.0005 (7)	−0.0004 (7)	0.0010 (7)
C10	0.0157 (7)	0.0304 (10)	0.0122 (8)	0.0002 (7)	−0.0028 (6)	−0.0014 (8)
C11	0.0188 (8)	0.0299 (10)	0.0133 (8)	−0.0035 (8)	−0.0024 (7)	−0.0004 (7)
C12	0.0255 (9)	0.0312 (11)	0.0216 (10)	−0.0014 (8)	−0.0018 (8)	0.0027 (8)
C13	0.0406 (12)	0.0299 (11)	0.0272 (11)	−0.0053 (10)	−0.0069 (10)	0.0046 (9)
C14	0.0441 (13)	0.0390 (13)	0.0226 (10)	−0.0184 (11)	0.0001 (10)	0.0055 (9)
C15	0.0301 (10)	0.0476 (13)	0.0173 (9)	−0.0124 (10)	0.0012 (9)	0.0003 (9)
C16	0.0213 (9)	0.0395 (12)	0.0123 (8)	−0.0058 (8)	−0.0012 (7)	−0.0020 (8)
C17	0.0181 (8)	0.0472 (13)	0.0138 (8)	−0.0011 (9)	0.0001 (7)	−0.0051 (9)
C18	0.0199 (8)	0.0377 (11)	0.0141 (8)	0.0039 (8)	−0.0037 (7)	−0.0066 (8)
C19	0.0267 (10)	0.0450 (13)	0.0195 (10)	0.0115 (10)	−0.0039 (8)	−0.0102 (9)
C20	0.0374 (11)	0.0362 (12)	0.0275 (11)	0.0151 (10)	−0.0078 (9)	−0.0084 (10)
C21	0.0365 (11)	0.0303 (11)	0.0234 (10)	0.0042 (10)	−0.0066 (9)	−0.0016 (9)
C22	0.0256 (9)	0.0307 (11)	0.0165 (9)	0.0025 (8)	−0.0031 (7)	0.0003 (8)
C23	0.0186 (8)	0.0304 (10)	0.0143 (8)	0.0012 (8)	−0.0047 (7)	−0.0026 (7)
C24	0.0318 (10)	0.0232 (10)	0.0427 (13)	0.0091 (9)	0.0012 (10)	−0.0019 (9)
C25	0.0477 (14)	0.0398 (14)	0.0496 (15)	0.0210 (12)	−0.0065 (13)	0.0051 (12)

O1—C7	1.220 (2)	C13—C14	1.420 (3)
O2—C1	1.358 (2)	C13—H13A	0.9300
O2—C24	1.438 (2)	C14—C15	1.349 (3)
C1—C2	1.395 (3)	C14—H14A	0.9300
C1—C6	1.407 (3)	C15—C16	1.430 (3)
C2—C3	1.386 (3)	C15—H15A	0.9300
C2—H2A	0.9300	C16—C17	1.394 (3)
C3—C4	1.386 (3)	C17—C18	1.392 (3)
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.386 (3)	C18—C19	1.429 (3)
C4—H4A	0.9300	C18—C23	1.440 (3)
C5—C6	1.394 (3)	C19—C20	1.356 (3)
C5—H5A	0.9300	C19—H19A	0.9300
C6—C7	1.494 (3)	C20—C21	1.419 (3)
C7—C8	1.483 (2)	C20—H20A	0.9300
C8—C9	1.331 (3)	C21—C22	1.362 (3)
C8—H8A	0.9300	C21—H21A	0.9300
C9—C10	1.488 (2)	C22—C23	1.430 (3)
C9—H9A	0.9300	C22—H22A	0.9300
C10—C11	1.408 (3)	C24—C25	1.501 (3)
C10—C23	1.409 (3)	C24—H24A	0.9700
C11—C12	1.432 (3)	C24—H24C	0.9700
C11—C16	1.438 (3)	C25—H25C	0.9600
C12—C13	1.361 (3)	C25—H25A	0.9600
C12—H12A	0.9300	C25—H25B	0.9600
C1—O2—C24	119.44 (16)	C15—C14—H14A	119.6
O2—C1—C2	124.38 (18)	C13—C14—H14A	119.6
O2—C1—C6	115.55 (16)	C14—C15—C16	121.1 (2)
C2—C1—C6	120.01 (18)	C14—C15—H15A	119.4
C3—C2—C1	119.7 (2)	C16—C15—H15A	119.4
C3—C2—H2A	120.2	C17—C16—C15	122.11 (18)
C1—C2—H2A	120.2	C17—C16—C11	119.38 (19)
C4—C3—C2	121.02 (19)	C15—C16—C11	118.5 (2)
C4—C3—H3A	119.5	C18—C17—C16	121.65 (18)
C2—C3—H3A	119.5	C18—C17—H17A	119.2
C5—C4—C3	119.2 (2)	C16—C17—H17A	119.2
C5—C4—H4A	120.4	C17—C18—C19	122.20 (18)
C3—C4—H4A	120.4	C17—C18—C23	119.37 (19)
C4—C5—C6	121.3 (2)	C19—C18—C23	118.42 (19)
C4—C5—H5A	119.3	C20—C19—C18	121.36 (19)
C6—C5—H5A	119.3	C20—C19—H19A	119.3
C5—C6—C1	118.72 (17)	C18—C19—H19A	119.3
C5—C6—C7	118.25 (16)	C19—C20—C21	120.3 (2)
C1—C6—C7	123.03 (16)	C19—C20—H20A	119.9
O1—C7—C8	121.85 (16)	C21—C20—H20A	119.9
O1—C7—C6	119.69 (16)	C22—C21—C20	120.7 (2)
C8—C7—C6	118.27 (15)	C22—C21—H21A	119.7
C9—C8—C7	123.95 (16)	C20—C21—H21A	119.7
C9—C8—H8A	118.0	C21—C22—C23	120.98 (19)
C7—C8—H8A	118.0	C21—C22—H22A	119.5
C8—C9—C10	125.25 (16)	C23—C22—H22A	119.5
C8—C9—H9A	117.4	C10—C23—C22	122.13 (17)
C10—C9—H9A	117.4	C10—C23—C18	119.57 (18)
C11—C10—C23	120.25 (16)	C22—C23—C18	118.26 (18)
C11—C10—C9	119.99 (17)	O2—C24—C25	106.01 (18)
C23—C10—C9	119.76 (17)	O2—C24—H24A	110.5
C10—C11—C12	122.03 (17)	C25—C24—H24A	110.5
C10—C11—C16	119.65 (18)	O2—C24—H24C	110.5
C12—C11—C16	118.32 (18)	C25—C24—H24C	110.5
C13—C12—C11	120.80 (19)	H24A—C24—H24C	108.7
C13—C12—H12A	119.6	C24—C25—H25C	109.5
C11—C12—H12A	119.6	C24—C25—H25A	109.5
C12—C13—C14	120.5 (2)	H25C—C25—H25A	109.5
C12—C13—H13A	119.7	C24—C25—H25B	109.5
C14—C13—H13A	119.7	H25C—C25—H25B	109.5
C15—C14—C13	120.7 (2)	H25A—C25—H25B	109.5
C24—O2—C1—C2	2.8 (3)	C12—C13—C14—C15	−1.3 (3)
C24—O2—C1—C6	179.74 (18)	C13—C14—C15—C16	0.2 (3)
O2—C1—C2—C3	174.88 (19)	C14—C15—C16—C17	−179.5 (2)
C6—C1—C2—C3	−2.0 (3)	C14—C15—C16—C11	0.9 (3)
C1—C2—C3—C4	−0.7 (3)	C10—C11—C16—C17	−1.1 (3)
C2—C3—C4—C5	1.6 (3)	C12—C11—C16—C17	179.48 (18)
C3—C4—C5—C6	0.0 (3)	C10—C11—C16—C15	178.43 (17)
C4—C5—C6—C1	−2.6 (3)	C12—C11—C16—C15	−0.9 (3)
C4—C5—C6—C7	177.64 (18)	C15—C16—C17—C18	179.67 (18)
O2—C1—C6—C5	−173.54 (17)	C11—C16—C17—C18	−0.8 (3)
C2—C1—C6—C5	3.6 (3)	C16—C17—C18—C19	179.27 (18)
O2—C1—C6—C7	6.2 (3)	C16—C17—C18—C23	0.1 (3)
C2—C1—C6—C7	−176.71 (18)	C17—C18—C19—C20	−179.9 (2)
C5—C6—C7—O1	32.2 (3)	C23—C18—C19—C20	−0.7 (3)
C1—C6—C7—O1	−147.54 (19)	C18—C19—C20—C21	−0.8 (3)
C5—C6—C7—C8	−142.93 (18)	C19—C20—C21—C22	2.0 (3)
C1—C6—C7—C8	37.4 (3)	C20—C21—C22—C23	−1.5 (3)
O1—C7—C8—C9	19.0 (3)	C11—C10—C23—C22	177.84 (18)
C6—C7—C8—C9	−166.01 (18)	C9—C10—C23—C22	−2.6 (3)
C7—C8—C9—C10	4.2 (3)	C11—C10—C23—C18	−4.4 (3)
C8—C9—C10—C11	78.2 (2)	C9—C10—C23—C18	175.19 (16)
C8—C9—C10—C23	−101.4 (2)	C21—C22—C23—C10	177.78 (18)
C23—C10—C11—C12	−176.92 (18)	C21—C22—C23—C18	0.0 (3)
C9—C10—C11—C12	3.5 (3)	C17—C18—C23—C10	2.5 (3)
C23—C10—C11—C16	3.7 (3)	C19—C18—C23—C10	−176.73 (17)
C9—C10—C11—C16	−175.84 (16)	C17—C18—C23—C22	−179.67 (18)
C10—C11—C12—C13	−179.47 (19)	C19—C18—C23—C22	1.1 (3)
C16—C11—C12—C13	−0.1 (3)	C1—O2—C24—C25	178.57 (19)
C11—C12—C13—C14	1.2 (3)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C11/C16–C18/C23 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1i	0.93	2.59	3.205 (3)	124
C8—H8A···O1ii	0.93	2.35	3.093 (2)	136
C9—H9A···Cg2ii	0.93	2.88	3.7609 (19)	160
C24—H24A···Cg1ii	0.97	2.86	3.739 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C11/C16–C18/C23 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O1i	0.93	2.59	3.205 (3)	124
C8—H8A⋯O1ii	0.93	2.35	3.093 (2)	136
C9—H9A⋯Cg2ii	0.93	2.88	3.7609 (19)	160
C24—H24A⋯Cg1ii	0.97	2.86	3.739 (2)	151

Symmetry codes: (i) ; (ii) .