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

In the mol-ecule of the title heteroaryl chalcone derivative, C(21)H(14)O(2), the almost planar prop-2-en-1-one unit [r.m.s. deviation = 0.0087 (1) Å] forms dihedral angles of 5.81 (7) and 49.85 (6)°, respectively, with the furan ring and anthracene ring system. In the crystal structure, the mol-ecules are linked into a two-dimensional network parallel to (100) by C-H⋯O hydrogen bonds and π⋯π inter-actions involving the furan rings [centroid-centroid distance = 3.7205 (6) Å].

Related literature

For background and applications of chalcones, see: Gaber et al. (2008 ▶); Niu et al. (2006 ▶); Xu et al. (2005 ▶). For related structures, see: Chantrapromma et al. (2009 ▶, 2010 ▶); Fun et al. (2009 ▶); Suwunwong et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H14O2

M = 298.32

Monoclinic,

a = 21.5743 (4) Å

b = 5.4571 (1) Å

c = 12.8394 (2) Å

β = 104.099 (1)°

V = 1466.09 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.55 × 0.25 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.955, T max = 0.994

19468 measured reflections

4251 independent reflections

3549 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.118

S = 1.03

4251 reflections

264 parameters

All H-atom parameters refined

Δρmax = 0.37 e Å−3

Δρmin = −0.22 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/S1600536810005982/ci5032sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005982/ci5032Isup2.hkl

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

C21H14O2	F(000) = 624
Mr = 298.32	Dx = 1.352 Mg m−3
Monoclinic, P21/c	Melting point = 423–424 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 21.5743 (4) Å	Cell parameters from 4251 reflections
b = 5.4571 (1) Å	θ = 2.9–30.0°
c = 12.8394 (2) Å	µ = 0.09 mm−1
β = 104.099 (1)°	T = 100 K
V = 1466.09 (4) Å3	Plate, yellow
Z = 4	0.55 × 0.25 × 0.07 mm

Bruker APEXII CCD area-detector diffractometer	4251 independent reflections
Radiation source: sealed tube	3549 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 30.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −26→30
Tmin = 0.955, Tmax = 0.994	k = −7→7
19468 measured reflections	l = −17→18

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0624P)2 + 0.4737P] where P = (Fo2 + 2Fc2)/3
4251 reflections	(Δ/σ)max = 0.001
264 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.22 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 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
O1	0.13071 (4)	0.32065 (14)	0.15881 (6)	0.02003 (17)
O2	0.00592 (3)	0.46137 (14)	0.12589 (6)	0.01846 (17)
C1	−0.04942 (5)	0.5903 (2)	0.11274 (9)	0.0201 (2)
H1	−0.0880 (7)	0.489 (3)	0.1018 (12)	0.030 (4)*
C2	−0.03863 (5)	0.8346 (2)	0.11454 (9)	0.0208 (2)
H2	−0.0701 (8)	0.964 (3)	0.1084 (13)	0.034 (4)*
C3	0.02854 (5)	0.8641 (2)	0.12983 (8)	0.0177 (2)
H3	0.0517 (7)	1.019 (3)	0.1342 (11)	0.027 (4)*
C4	0.05367 (5)	0.63332 (19)	0.13651 (8)	0.0152 (2)
C5	0.11877 (5)	0.54141 (19)	0.15040 (8)	0.0150 (2)
C6	0.16862 (5)	0.72918 (19)	0.15159 (8)	0.0163 (2)
C7	0.22914 (5)	0.66214 (19)	0.15739 (8)	0.0159 (2)
C8	0.28183 (5)	0.83333 (19)	0.15569 (8)	0.01475 (19)
C9	0.34004 (5)	0.80973 (19)	0.23544 (8)	0.0153 (2)
C10	0.34956 (5)	0.6249 (2)	0.31680 (8)	0.0183 (2)
C11	0.40571 (5)	0.6100 (2)	0.39433 (9)	0.0214 (2)
C12	0.45582 (5)	0.7804 (2)	0.39679 (9)	0.0231 (2)
C13	0.44862 (5)	0.9614 (2)	0.32146 (9)	0.0214 (2)
C14	0.39083 (5)	0.9814 (2)	0.23836 (8)	0.0166 (2)
C15	0.38256 (5)	1.1693 (2)	0.16251 (8)	0.0181 (2)
C16	0.32655 (5)	1.19033 (19)	0.08122 (8)	0.0164 (2)
C17	0.31916 (5)	1.3816 (2)	0.00291 (9)	0.0201 (2)
C18	0.26502 (6)	1.3994 (2)	−0.07801 (9)	0.0218 (2)
C19	0.21559 (5)	1.2226 (2)	−0.08673 (8)	0.0209 (2)
C20	0.22049 (5)	1.0396 (2)	−0.01267 (8)	0.0183 (2)
C21	0.27525 (5)	1.01872 (19)	0.07639 (8)	0.0154 (2)
H6	0.1563 (7)	0.895 (3)	0.1471 (11)	0.021 (3)*
H7	0.2399 (6)	0.482 (3)	0.1653 (11)	0.019 (3)*
H10	0.3158 (7)	0.507 (3)	0.3176 (11)	0.024 (4)*
H11	0.4105 (8)	0.479 (3)	0.4498 (13)	0.035 (4)*
H12	0.4960 (7)	0.766 (3)	0.4544 (13)	0.033 (4)*
H13	0.4831 (8)	1.086 (3)	0.3216 (13)	0.032 (4)*
H15	0.4171 (7)	1.291 (3)	0.1670 (11)	0.024 (4)*
H17	0.3534 (7)	1.501 (3)	0.0097 (12)	0.027 (4)*
H18	0.2611 (8)	1.533 (3)	−0.1306 (13)	0.036 (4)*
H19	0.1780 (7)	1.232 (3)	−0.1469 (11)	0.025 (4)*
H20	0.1864 (7)	0.916 (3)	−0.0210 (11)	0.025 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0184 (4)	0.0134 (4)	0.0265 (4)	−0.0007 (3)	0.0020 (3)	0.0008 (3)
O2	0.0144 (3)	0.0166 (4)	0.0236 (4)	−0.0032 (3)	0.0031 (3)	0.0005 (3)
C1	0.0134 (5)	0.0248 (5)	0.0216 (5)	−0.0011 (4)	0.0031 (4)	0.0001 (4)
C2	0.0154 (5)	0.0222 (5)	0.0244 (5)	0.0021 (4)	0.0042 (4)	0.0002 (4)
C3	0.0165 (5)	0.0165 (5)	0.0196 (5)	−0.0007 (4)	0.0034 (4)	−0.0002 (4)
C4	0.0142 (4)	0.0148 (5)	0.0161 (4)	−0.0026 (4)	0.0027 (3)	0.0000 (3)
C5	0.0147 (4)	0.0143 (5)	0.0149 (4)	−0.0017 (3)	0.0016 (3)	−0.0006 (3)
C6	0.0161 (5)	0.0125 (4)	0.0199 (4)	−0.0013 (4)	0.0038 (4)	−0.0004 (4)
C7	0.0163 (5)	0.0139 (5)	0.0170 (4)	−0.0011 (4)	0.0030 (3)	−0.0004 (3)
C8	0.0136 (4)	0.0137 (4)	0.0175 (4)	−0.0003 (3)	0.0047 (3)	−0.0019 (3)
C9	0.0140 (4)	0.0155 (5)	0.0173 (4)	0.0008 (4)	0.0051 (3)	−0.0012 (4)
C10	0.0162 (5)	0.0180 (5)	0.0212 (5)	0.0012 (4)	0.0054 (4)	0.0007 (4)
C11	0.0190 (5)	0.0232 (5)	0.0219 (5)	0.0047 (4)	0.0049 (4)	0.0032 (4)
C12	0.0156 (5)	0.0286 (6)	0.0232 (5)	0.0024 (4)	0.0011 (4)	0.0001 (4)
C13	0.0139 (5)	0.0248 (6)	0.0245 (5)	−0.0009 (4)	0.0027 (4)	−0.0015 (4)
C14	0.0135 (4)	0.0177 (5)	0.0192 (4)	−0.0002 (4)	0.0050 (4)	−0.0026 (4)
C15	0.0157 (5)	0.0184 (5)	0.0213 (5)	−0.0025 (4)	0.0067 (4)	−0.0012 (4)
C16	0.0167 (5)	0.0153 (5)	0.0190 (4)	−0.0003 (4)	0.0075 (4)	−0.0014 (4)
C17	0.0217 (5)	0.0176 (5)	0.0234 (5)	−0.0010 (4)	0.0105 (4)	0.0013 (4)
C18	0.0259 (6)	0.0213 (5)	0.0207 (5)	0.0027 (4)	0.0106 (4)	0.0039 (4)
C19	0.0204 (5)	0.0243 (6)	0.0175 (5)	0.0024 (4)	0.0038 (4)	0.0011 (4)
C20	0.0170 (5)	0.0193 (5)	0.0184 (4)	−0.0003 (4)	0.0037 (4)	−0.0003 (4)
C21	0.0150 (4)	0.0149 (5)	0.0168 (4)	0.0006 (4)	0.0049 (3)	−0.0011 (4)

O1—C5	1.2312 (13)	C10—H10	0.973 (15)
O2—C1	1.3606 (13)	C11—C12	1.4209 (17)
O2—C4	1.3754 (12)	C11—H11	0.997 (17)
C1—C2	1.3526 (16)	C12—C13	1.3642 (17)
C1—H1	0.981 (16)	C12—H12	0.996 (16)
C2—C3	1.4235 (15)	C13—C14	1.4342 (14)
C2—H2	0.968 (17)	C13—H13	1.007 (16)
C3—C4	1.3654 (14)	C14—C15	1.3950 (15)
C3—H3	0.974 (15)	C15—C16	1.3959 (14)
C4—C5	1.4609 (14)	C15—H15	0.988 (15)
C5—C6	1.4827 (14)	C16—C17	1.4310 (15)
C6—C7	1.3406 (14)	C16—C21	1.4396 (14)
C6—H6	0.941 (15)	C17—C18	1.3645 (16)
C7—C8	1.4757 (14)	C17—H17	0.972 (15)
C7—H7	1.009 (14)	C18—C19	1.4225 (17)
C8—C21	1.4176 (14)	C18—H18	0.984 (17)
C8—C9	1.4196 (14)	C19—C20	1.3653 (15)
C9—C10	1.4303 (14)	C19—H19	0.975 (14)
C9—C14	1.4353 (14)	C20—C21	1.4346 (14)
C10—C11	1.3701 (15)	C20—H20	0.984 (15)
C1—O2—C4	105.84 (8)	C10—C11—H11	118.7 (9)
C2—C1—O2	111.43 (10)	C12—C11—H11	120.6 (9)
C2—C1—H1	134.0 (9)	C13—C12—C11	120.23 (10)
O2—C1—H1	114.6 (9)	C13—C12—H12	120.8 (9)
C1—C2—C3	106.20 (10)	C11—C12—H12	119.0 (9)
C1—C2—H2	127.0 (10)	C12—C13—C14	120.72 (10)
C3—C2—H2	126.8 (10)	C12—C13—H13	122.1 (9)
C4—C3—C2	106.24 (9)	C14—C13—H13	117.2 (9)
C4—C3—H3	127.2 (9)	C15—C14—C13	121.04 (10)
C2—C3—H3	126.6 (9)	C15—C14—C9	119.63 (9)
C3—C4—O2	110.29 (9)	C13—C14—C9	119.30 (10)
C3—C4—C5	132.80 (9)	C14—C15—C16	121.51 (10)
O2—C4—C5	116.90 (9)	C14—C15—H15	119.0 (8)
O1—C5—C4	121.40 (9)	C16—C15—H15	119.5 (8)
O1—C5—C6	122.66 (9)	C15—C16—C17	120.89 (10)
C4—C5—C6	115.93 (9)	C15—C16—C21	119.67 (9)
C7—C6—C5	120.41 (10)	C17—C16—C21	119.43 (9)
C7—C6—H6	121.6 (9)	C18—C17—C16	121.01 (10)
C5—C6—H6	118.0 (9)	C18—C17—H17	120.7 (9)
C6—C7—C8	124.74 (10)	C16—C17—H17	118.3 (9)
C6—C7—H7	117.9 (8)	C17—C18—C19	119.86 (10)
C8—C7—H7	117.4 (8)	C17—C18—H18	119.4 (9)
C21—C8—C9	119.94 (9)	C19—C18—H18	120.8 (9)
C21—C8—C7	121.30 (9)	C20—C19—C18	120.81 (10)
C9—C8—C7	118.76 (9)	C20—C19—H19	120.0 (9)
C8—C9—C10	122.36 (9)	C18—C19—H19	119.2 (9)
C8—C9—C14	119.68 (9)	C19—C20—C21	121.48 (10)
C10—C9—C14	117.92 (9)	C19—C20—H20	119.7 (8)
C11—C10—C9	121.13 (10)	C21—C20—H20	118.8 (8)
C11—C10—H10	118.9 (8)	C8—C21—C20	123.23 (9)
C9—C10—H10	119.9 (8)	C8—C21—C16	119.46 (9)
C10—C11—C12	120.68 (10)	C20—C21—C16	117.25 (9)
C4—O2—C1—C2	0.05 (12)	C12—C13—C14—C15	178.54 (10)
O2—C1—C2—C3	0.07 (13)	C12—C13—C14—C9	0.46 (16)
C1—C2—C3—C4	−0.16 (12)	C8—C9—C14—C15	−0.25 (15)
C2—C3—C4—O2	0.20 (11)	C10—C9—C14—C15	−177.91 (9)
C2—C3—C4—C5	179.04 (10)	C8—C9—C14—C13	177.85 (9)
C1—O2—C4—C3	−0.16 (11)	C10—C9—C14—C13	0.20 (15)
C1—O2—C4—C5	−179.20 (8)	C13—C14—C15—C16	179.91 (10)
C3—C4—C5—O1	176.89 (11)	C9—C14—C15—C16	−2.01 (16)
O2—C4—C5—O1	−4.33 (14)	C14—C15—C16—C17	−178.97 (10)
C3—C4—C5—C6	−4.22 (16)	C14—C15—C16—C21	1.51 (15)
O2—C4—C5—C6	174.56 (8)	C15—C16—C17—C18	178.56 (10)
O1—C5—C6—C7	2.92 (15)	C21—C16—C17—C18	−1.92 (16)
C4—C5—C6—C7	−175.95 (9)	C16—C17—C18—C19	−1.51 (17)
C5—C6—C7—C8	178.00 (9)	C17—C18—C19—C20	2.45 (17)
C6—C7—C8—C21	−49.44 (15)	C18—C19—C20—C21	0.14 (17)
C6—C7—C8—C9	130.63 (11)	C9—C8—C21—C20	173.77 (9)
C21—C8—C9—C10	−179.46 (9)	C7—C8—C21—C20	−6.16 (15)
C7—C8—C9—C10	0.48 (15)	C9—C8—C21—C16	−3.49 (15)
C21—C8—C9—C14	2.99 (15)	C7—C8—C21—C16	176.57 (9)
C7—C8—C9—C14	−177.07 (9)	C19—C20—C21—C8	179.21 (10)
C8—C9—C10—C11	−178.45 (10)	C19—C20—C21—C16	−3.47 (15)
C14—C9—C10—C11	−0.86 (15)	C15—C16—C21—C8	1.27 (15)
C9—C10—C11—C12	0.87 (17)	C17—C16—C21—C8	−178.26 (9)
C10—C11—C12—C13	−0.18 (18)	C15—C16—C21—C20	−176.16 (9)
C11—C12—C13—C14	−0.48 (18)	C17—C16—C21—C20	4.31 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.98 (2)	2.34 (2)	3.2871 (14)	165 (1)
C6—H6···O1i	0.94 (2)	2.40 (2)	3.3366 (13)	173 (1)
C19—H19···O1ii	0.98 (1)	2.47 (1)	3.3419 (13)	148 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.98 (2)	2.34 (2)	3.2871 (14)	165 (1)
C6—H6⋯O1i	0.94 (2)	2.40 (2)	3.3366 (13)	173 (1)
C19—H19⋯O1ii	0.98 (1)	2.47 (1)	3.3419 (13)	148 (1)

Symmetry codes: (i) ; (ii) .